Compounds, coating compositions comprising the same, organic light emitting devices using the same, and methods of making the same

Abstract

The present specification relates to compounds of Chemical Formula 1, coating compositions comprising the compounds, organic light emitting devices using the coating compositions, and methods of manufacturing the same.

Description

Technical Field

[0001] This application claims priority and benefit to Korean Patent Applications No. 10-2021-0121821, No. 10-2022-0096200 and No. 10-2022-0096204, filed with the Korean Intellectual Property Office on September 13, 2021, August 2, 2022 and August 2, 2022, respectively, the entire contents of which are incorporated herein by reference.

[0002] This specification relates to compounds, coating compositions comprising said compounds, organic light-emitting devices formed by using said coating compositions, and methods of manufacturing the same. Background Technology

[0003] Organic light emission (OLED) is one example of converting electric current into visible light through internal processes of specific organic molecules. The principle of OLED is as follows: When an organic material layer is placed between the anode and cathode, and a current is applied between the two electrodes, electrons and holes are injected into the organic material layer from the cathode and anode, respectively. The injected electrons and holes recombine to form excitons, which then return to the ground state and emit light. OLED devices utilizing this principle typically consist of a cathode, an anode, and an organic material layer disposed therebetween (e.g., an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer).

[0004] In existing technologies, deposition methods are commonly used to manufacture organic light-emitting devices. However, when manufacturing organic light-emitting devices by deposition, there is a frequent problem of material loss. Therefore, in order to solve this problem, a solution method has been developed to manufacture devices, which can improve production efficiency due to less material loss. It is also necessary to develop materials that can be used during the solution method.

[0005] Materials used in organic light-emitting devices for solution processing need to have the properties described below.

[0006] First, the materials used in organic light-emitting devices need to be able to form a storable homogeneous solution. Because commercially available materials used in deposition methods have good crystallinity, they cannot dissolve well in solution, or even if they do form a solution, they tend to crystallize, potentially leading to changes in the concentration gradient of the solution over time, or the formation of defective devices.

[0007] Second, the materials used in the solution process need to be excellent in terms of coatability, so that a film with a uniform thickness can be formed during film formation without pores or agglomeration.

[0008] Third, when manufacturing organic light-emitting devices, the solution-processed layers need to be resistant to the solvents and materials used in the formation of other layers, and need to have excellent current efficiency and excellent lifespan characteristics.

[0009] Therefore, there is a need in this field to develop new organic materials. Summary of the Invention

[0010] Technical issues

[0011] This specification provides compounds, coating compositions comprising the compounds, organic light-emitting devices formed by using the coating compositions, and methods for manufacturing the same.

[0012] Technical solution

[0013] An exemplary embodiment of this specification provides a compound of the following chemical formula 1.

[0014] [Chemical Formula 1]

[0015]

[0016] In chemical formula 1,

[0017] La is -Lx-A-Ly-; a substituted or unsubstituted divalent dihydroanthracene group; a substituted or unsubstituted divalent heterocyclic group; a substituted or unsubstituted divalent fluorenyl group; or a substituted or unsubstituted divalent spirodifluorenyl group.

[0018] Lx and Ly may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group.

[0019] A is a substituted or unsubstituted divalent dihydroanthracene group; a substituted or unsubstituted divalent heterocyclic group; a substituted or unsubstituted divalent fluorenyl group; or a substituted or unsubstituted divalent spirodifluorenyl group.

[0020] L1 to L6 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted divalent heterocyclic group.

[0021] L11 to L14 may be the same as or different from each other, and each is independently a direct bond; -O-; substituted or unsubstituted alkylene groups; substituted or unsubstituted arylene groups; or substituted or unsubstituted divalent heterocyclic groups.

[0022] Ar1 to Ar4 may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0023] X1 to X4 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a photocurable group; or a thermosetting group, and two or more of X1 to X4 are photocurable groups or thermosetting groups.

[0024] R1 to R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0025] l1, l3, l4, and l6 are each integers from 0 to 3, and when l1, l3, l4, and l6 are each 2 or greater, the structures within the parentheses are either the same or different from each other.

[0026] l11 to l14 are each integers from 1 to 3, and when l11 to l14 are each 2 or greater, the structures within the parentheses are either the same or different from each other.

[0027] r1 and r4 are each integers from 1 to 4, r2 and r3 are each integers from 1 to 3, and when r1 to r4 are each 2 or greater, the substituents in parentheses are either the same or different from each other.

[0028] m is an integer from 1 to 10, and when m is 2 or greater, the structures in parentheses are either the same or different from each other.

[0029] Another exemplary embodiment of this specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic material layer having one or more layers, including a light-emitting layer, disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer comprise the coating composition described above or a cured product thereof.

[0030] Another exemplary embodiment of this specification provides a method for manufacturing an organic light-emitting device, the method comprising: preparing a substrate; forming a first electrode on the substrate; forming an organic material layer having one or more layers on the first electrode; and forming a second electrode on the organic material layer, wherein forming the organic material layer comprises forming an organic material layer having one or more layers by using the coating composition.

[0031] Beneficial effects

[0032] Because the compound according to one exemplary embodiment of this specification has a suitable viscosity for the solvent, it is easy to perform solution or inkjet processes.

[0033] Furthermore, since the compound according to one exemplary embodiment of this specification has excellent solubility, it has the advantage of being able to select a variety of solvents when preparing the coating composition.

[0034] Furthermore, the compound according to an exemplary embodiment of this specification has the advantage of forming a stable film that is not damaged by subsequent solution processing by forming a fully cured film through heat treatment or light treatment.

[0035] Furthermore, since the compound according to an exemplary embodiment of this specification exhibits resistance to a particular solvent after curing, a solution method can be used when manufacturing the device, and thus the device can be manufactured with a large area.

[0036] Furthermore, the compound according to an exemplary embodiment of this specification can be used as a material for the organic material layer of an organic light-emitting device, and can provide low driving voltage, high luminous efficiency and / or long lifespan characteristics. Attached Figure Description

[0037] Figure 1 A diagram illustrating the structure of an organic light-emitting device according to an exemplary embodiment of this specification.

[0038] 101: Base

[0039] 201: Anode

[0040] 301: Hole Injection Layer

[0041] 401: Hole Transport Layer

[0042] 501: Emissive layer

[0043] 601: Electron Transport and Injection Layer

[0044] 701: Cathode Detailed Implementation

[0045] This instruction manual will be described in detail below.

[0046] An exemplary embodiment of this specification provides a compound of the following chemical formula 1.

[0047] [Chemical Formula 1]

[0048]

[0049] In chemical formula 1,

[0050] La is -Lx-A-Ly-; a substituted or unsubstituted divalent dihydroanthracene group; a substituted or unsubstituted divalent heterocyclic group; a substituted or unsubstituted divalent fluorenyl group; or a substituted or unsubstituted divalent spirodifluorenyl group.

[0051] Lx and Ly may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group.

[0052] A is a substituted or unsubstituted divalent dihydroanthracene group; a substituted or unsubstituted divalent heterocyclic group; a substituted or unsubstituted divalent fluorenyl group; or a substituted or unsubstituted divalent spirodifluorenyl group.

[0053] L1 to L6 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted divalent heterocyclic group.

[0054] L11 to L14 may be the same as or different from each other, and each is independently a direct bond; -O-; substituted or unsubstituted alkylene groups; substituted or unsubstituted arylene groups; or substituted or unsubstituted divalent heterocyclic groups.

[0055] Ar1 to Ar4 may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0056] X1 to X4 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a photocurable group; or a thermosetting group, and two or more of X1 to X4 are photocurable groups or thermosetting groups.

[0057] R1 to R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0058] l1, l3, l4, and l6 are each integers from 0 to 3, and when l1, l3, l4, and l6 are each 2 or greater, the structures within the parentheses are either the same or different from each other.

[0059] l11 to l14 are each integers from 1 to 3, and when l11 to l14 are each 2 or greater, the structures within the parentheses are either the same or different from each other.

[0060] r1 and r4 are each integers from 1 to 4, r2 and r3 are each integers from 1 to 3, and when r1 to r4 are each 2 or greater, the substituents in parentheses are either the same or different from each other.

[0061] m is an integer from 1 to 10, and when m is 2 or greater, the structures in parentheses are either the same or different from each other.

[0062] Typically, in the case of polymers, hole mobility is improved due to the long conjugation length, but there is a problem that the polymer is not easily soluble in solvents, making it difficult to form organic material layers by solution methods. Conversely, in the case of monomolecular compounds, the compounds are easily soluble in solvents, thus favoring solution methods, but due to the short conjugation length, there is little intramolecular hole migration, and intermolecular hole migration is the main factor, resulting in increased driving voltage and reduced efficiency.

[0063] The compound according to an exemplary embodiment of this specification exhibits all the advantages of both polymers and monomolecules. Specifically, the compound is readily soluble in solvents and can therefore be used to form organic material layers via solution processing (or inkjet printing), and due to its excellent hole mobility, it exhibits the effect of reducing drive voltage and improving efficiency when applied to devices. Furthermore, another layer can also be formed via solution processing when another layer is stacked on the surface of an organic material layer formed using this compound. These effects arise from the structural characteristics of the compound of Formula 1.

[0064] Regarding hole mobility, compounds of Formula 1 contain four or more (2m+2) N atoms, but the number of N atoms relative to molecular weight is similar to that of a single molecule. Generally, when the number of N atoms relatively increases in compounds with the same molecular weight, the HOMO level decreases (approaching the vacuum level), thus increasing the difference between the HOMO level and the HTL, which leads to a decrease in hole mobility and an increase in driving voltage.

[0065] Conversely, compounds of Formula 1 exhibit improved hole mobility and good ink properties due to their smaller molecular weight compared to polymers.

[0066] Specifically, when La is a partial bonding position of a divalent heterocyclic group, a divalent fluorene group, or a divalent spirodifluorene group (especially, When La has the above structure, the compounds of Formula 1 contain four or more structures in which N and a linking group are connected, resulting in an increased conjugation length and thus an improved hole mobility. Therefore, compared to the monomolecular form, intermolecular hole migration is reduced and intramolecular hole migration is increased, thereby exhibiting an effect of improved hole mobility. That is, when La has the above structure, the compounds of Formula 1 contain four or more structures in which N and a linking group are connected, resulting in an increased conjugation length and thus exhibiting an effect of improved hole mobility. Therefore, the compounds of Formula 1 exhibit the effect of reducing driving voltage and improving efficiency when applied to devices.

[0067] Furthermore, when La is at a partial bonding position of -Lx-A-Ly-, divalent dihydroanthracene, or divalent spirodifluorene (especially, In the case of La having the above structure, L1 and L6 are bonded to specific positions of fluorene at both ends (specifically, position 9) to interrupt the conjugation between fluorene and the chain, thereby maintaining a conjugation length and HOMO energy level similar to those of a monomolecule. However, because the chains are spatially close to each other, the intermolecular hole mobility increases compared to the monomolecule form, thus exhibiting an effect of improving hole mobility. That is, when La has the above structure, the compound of formula 1 contains four or more structures in which N and a linking group are connected, thereby reducing the intermolecular distance and constantly maintaining the HOMO-LUMO gap, and thus exhibiting an effect of improving hole mobility.

[0068] In this specification, "chain" refers to the -L1-NAr1-L2-NAr2-L3- and -L4-NAr3-L5-NAr4-L6- units of chemical formula 1.

[0069] In this specification, the linking group means one or more of L1 to L6 and La of chemical formula 1.

[0070] In one exemplary embodiment of this specification, N may be N contained in an amine group.

[0071] In one exemplary embodiment of this specification, the molecular weight of the compound of Formula 1 is 1,000 g / mol or greater but less than 10,000 g / mol. Specifically, the molecular weight of the compound of Formula 1 is from 1,000 g / mol to 5,000 g / mol. Therefore, it exhibits an effect similar to the viscosity of a single molecule.

[0072] Regarding the solution method, the compound according to an exemplary embodiment of the specification has a viscosity similar to that of a monomolecule by satisfying the aforementioned molecular weight range, and is therefore readily soluble in solvents, making solution processing (or inkjet printing) possible. Furthermore, since the compound of Formula 1 contains two or more curable groups to form crosslinks through heat treatment or light treatment, an organic material layer comprising a thin film structure can be provided. The organic material layer thus prepared has the advantage of forming a stable film that is not damaged by subsequent solution processing. That is, the compound can undergo solution processing (or inkjet printing) similarly to a monomolecule, and has the advantage of forming a film that is not damaged in the same way as a polymer.

[0073] Furthermore, when another layer is stacked on the surface of the organic material layer formed as described above, the organic material layer can withstand solution processing and can be prevented from dissolving, being morphologically affected, or decomposing due to solvents. Therefore, organic light-emitting devices with long lifespan characteristics can be provided because it is advantageous to maintain the film after film formation during device fabrication.

[0074] Furthermore, in the case of a compound according to an exemplary embodiment of this specification, an organic light-emitting device can be fabricated by solution application, thereby enabling the realization of a large-area device.

[0075] In this specification, "monomer" means a substance consisting of a single structure that does not have repeating units.

[0076] In one exemplary embodiment of this specification, the molecular weight of the monomolecule is less than 10,000 g / mol. Specifically, the molecular weight is from 100 g / mol to 5,000 g / mol.

[0077] In this specification, "polymer" means a polymer in which the same structure is repeated. That is, "polymer" means a polymer in which repeating units are present.

[0078] In one exemplary embodiment of this specification, the polymer has a number-average molecular weight of 10,000 g / mol to 5,000,000 g / mol. Specifically, the number-average molecular weight is 10,000 g / mol to 1,000,000 g / mol.

[0079] When a component (layer) is placed "on" another component (layer) in this specification, this includes not only the case where one component (layer) is in contact with another component, but also the case where there is another component (layer) between the two components (layers).

[0080] When a component “includes” a constituent element in this specification, unless otherwise specifically described, this does not mean that other constituent elements are excluded, but rather that other constituent elements may be included.

[0081] In this specification, "photocurable or thermosetting group" can mean a reactive substituent that crosslinks a compound by exposure to heat and / or light. Photocurable or thermosetting groups can be generated when free radicals arising from the decomposition of carbon-carbon multiple bonds or cyclic structures by light irradiation or heat treatment connect with each other.

[0082] In this specification, "curable group" means "photocurable group or thermosetting group".

[0083] Unless otherwise specified in this specification, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. While methods and materials similar to or equivalent to those described herein may be used in practice or testing of exemplary embodiments of the invention, suitable methods and materials will be described below. All publications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, unless a specific paragraph is cited, the present invention (including definitions) shall prevail. Furthermore, materials, methods, and examples are illustrative only and are not intended to be limiting.

[0084] In this instruction manual, “------” and This refers to the portion that is bonded to another substituent or bonding portion.

[0085] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and there is no restriction on the position of substitution, as long as the position is where the hydrogen atom is substituted (i.e., the position where the substituent can be substituted), and when two or more substituents are substituted, the two or more substituents can be the same as or different from each other.

[0086] In this specification, the term "substituted or unsubstituted" means substituted with one or more of the following substituents selected from: deuterium; halogen group; alkyl; cycloalkyl; alkoxy; aryloxy; amino; aryl; heterocyclic group; and crosslinkable group, substituted with two or more of the exemplified substituents linked together, or without substituents. For example, "substituents linked with two or more substituents" can be biphenyl. That is, biphenyl can also be aryl and can be interpreted as substituents linked with two phenyl groups.

[0087] Examples of substituents will be described below, but are not limited to.

[0088] Examples of halogen groups in this specification include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0089] In this specification, alkyl groups can be straight-chain or branched, and their number of carbon atoms is not particularly limited, but is preferably from 1 to 60. According to one exemplary embodiment, the number of carbon atoms in the alkyl group is from 1 to 30. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, etc.

[0090] In this specification, alkylene refers to a group having two bonding positions in an alkyl group (i.e., a divalent group). The above description of alkyl groups can be applied to alkylene groups, except that alkylene groups are divalent.

[0091] In this specification, the number of carbon atoms in the cycloalkyl group is not particularly limited, but is preferably from 3 to 60. According to one exemplary embodiment, the number of carbon atoms in the cycloalkyl group is from 3 to 30. Specific examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc.

[0092] In this specification, alkoxy groups can be straight-chain, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, and n-decoxy.

[0093] In this specification, the amino group may be selected from -NH2; alkylamino; arylalkylamino; arylamino; arylheteroarylamino; alkylheteroarylamino; and heteroarylamino, and is not limited thereto. The number of carbon atoms in the amino group is not particularly limited, but is preferably from 1 to 60.

[0094] In this specification, the number of carbon atoms in the aryl group is not particularly limited, but is preferably 6 to 60. According to one exemplary embodiment, the number of carbon atoms in the aryl group is 6 to 30. In one exemplary embodiment of this specification, the aryl group can be a monocyclic aryl or a polycyclic aryl. Specific examples of monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, etc. Examples of polycyclic aryl groups include naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, triphenylene, etc. It includes, but is not limited to, methyl, fluorene, etc.

[0095] In this specification, arylene refers to a group having two bonding positions in an aryl group (i.e., a divalent group). The above description of aryl can be applied to arylene, except that each arylene is a divalent group.

[0096] In this specification, the fluorene group may be substituted, and two substituents may bond together to form a spirocyclic structure.

[0097] When the fluorene group is substituted, the substituent can be... And the illustrated structures can be substituted with other substituents, however, the structures are not limited thereto.

[0098] In this specification, divalent fluorene refers to a group having two bonding sites (i.e., a divalent group) within the fluorene group. In this case, the bonding sites may be located on the benzene ring of the fluorene group or on a substituent that substituted the fluorene group. For example, the divalent fluorene group can be any of the following structures, but is not limited thereto.

[0099]

[0100] In this specification, divalent spirodifluorene means a group having two bonding sites (i.e., a divalent group). For example, divalent spirodifluorene can be any of the following structures, but is not limited thereto.

[0101]

[0102] In this specification, examples of arylamines include substituted or unsubstituted monoarylamines, substituted or unsubstituted diarylamines, or substituted or unsubstituted triarylamines. The aryl group in an arylamine can be a monocyclic aryl or a polycyclic aryl. An arylamine containing two or more aryl groups can comprise a monocyclic aryl, a polycyclic aryl, or both. For example, the aryl group in an arylamine can be selected from the above-described examples of aryl groups. The number of carbon atoms in an arylamine is not particularly limited, but is preferably 6 to 60.

[0103] In this specification, a heterocyclic group is an aromatic cyclic group, an aliphatic cyclic group, or a fused cyclic group consisting of an aromatic group and an aliphatic group, comprising one or more atoms other than carbon (i.e., one or more heteroatoms). Specifically, the heteroatoms may include one or more atoms selected from N, O, P, S, Si, Se, etc. The number of carbon atoms in the heterocyclic group is not particularly limited, but can be from 2 to 60. Examples of heterocyclic groups include thiophene, furanyl, pyrrole, imidazole, and thiazolyl groups. azole group, Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazenopyrazinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthridine, phenanthrolinyl, iso azole group, thiadiazole group, phenthiazin group, Examples include, but are not limited to, tonyl, thiotonyl, dibenzofuranyl, etc.

[0104] In this specification, the above description of heterocyclic groups can be applied to heteroaryl groups, except that heteroaryl groups are aromatic.

[0105] In this specification, a divalent heterocyclic group refers to a group having two bonding positions within a heterocyclic group. The above description of heterocyclic groups can be applied to divalent heterocyclic groups, the difference being that each divalent heterocyclic group is a divalent group. For example, a divalent heterocyclic group can have the following structures, but is not limited to them.

[0106]

[0107] In the structure, Cy1 and Cy2 are the same or different from each other and are each independently a substituted or unsubstituted aromatic ring; Y3 and Y4 are the same or different from each other and are each independently O; S; or SiRcRd; Y5 is O; S; CRaRb; or SiRcRd; and Ra to Rd are the same or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl.

[0108] In this specification, divalent dihydroanthrayl means a group having two bonding positions in a dihydroanthrayl group. For example, a divalent dihydroanthrayl group can have the following structures, but is not limited to them.

[0109]

[0110] In the structure, Y6 and Y7 are the same or different from each other and are each independently CRaRb, Ra and Rb are the same or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl.

[0111] In this specification, "adjacent" groups may mean a substituent that substitutes for an atom directly bonded to the atom substituted by the corresponding substituent, a substituent that is spatially closest to the corresponding substituent, or another substituent that substitutes for the atom substituted by the corresponding substituent. For example, two substituents that substitute for an ortho position in a benzene ring and two substituents that substitute for the same carbon atom in an aliphatic ring can be interpreted as groups that are "adjacent" to each other.

[0112] In this specification, in a ring formed by bonding adjacent groups, "ring" means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0113] In this specification, the hydrocarbon ring group can be an aromatic ring, an aliphatic ring, or a ring fused with an aromatic ring and an aliphatic ring.

[0114] In this invention, the above description of aryl groups can be applied to aromatic rings.

[0115] In this specification, the above description of cycloalkyl groups can be applied to aliphatic rings.

[0116] In one exemplary embodiment of this specification, chemical formula 1 is the following chemical formula 1-1.

[0117] [Chemical Formula 1-1]

[0118]

[0119] In chemical formula 1-1,

[0120] La, L1 to L6, L11, L14, Ar1 to Ar4, R1 to R4, l1, l3, l4, l6, l11, l14, r1 to r4, and m are the same as those defined in Chemical Formula 1.

[0121] X1 and X4 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group.

[0122] R11 and R12 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0123] r11 and r12 are each integers from 1 to 5, and when r11 and r12 are each 2 or greater, the substituents in parentheses are either the same or different from each other.

[0124] In one exemplary embodiment of this specification, chemical formula 1 is the following chemical formula 1-1-1 or 1-1-2.

[0125] [Chemical Formula 1-1-1]

[0126]

[0127] [Chemical Formula 1-1-2]

[0128]

[0129] In chemical formulas 1-1-1 and 1-1-2,

[0130] La, L1 to L6, Ar1 to Ar4, R1 to R4, l1, l3, l4, l6, r1 to r4, and m are the same as those defined in Chemical Formula 1.

[0131] X1 and X4 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group.

[0132] L11' and L14' may be the same as or different from each other, and each is an independent direct bond; or -O-,

[0133] R11 to R14 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0134] r13 and r14 are each integers from 1 to 4, r11 and r12 are each integers from 1 to 5, and when r11 to r14 are each 2 or greater, the substituents in parentheses are the same or different from each other.

[0135] In one exemplary embodiment of this specification, chemical formula 1 is the following chemical formula 1-A.

[0136] [Chemical Formula 1-A]

[0137]

[0138] In chemical formula 1-A,

[0139] La, L1 to L6, L11 to L14, Ar1 to Ar4, X1 to X4, R1 to R4, l1, l3, l4, l6, l11 to l14, r1 to r4 and m are the same as those defined in Formula 1.

[0140] In one exemplary embodiment of this specification, chemical formula 1 is the following chemical formula 1-A-1.

[0141] [Chemical Formula 1-A-1]

[0142]

[0143] In chemical formula 1-A-1,

[0144] La, L1 to L6, L11, L14, Ar1 to Ar4, R1 to R4, l1, l3, l4, l6, l11, l14, r1 to r4, and m are the same as those defined in Chemical Formula 1.

[0145] X1 and X4 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group.

[0146] R11 and R12 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0147] r11 and r12 are each integers from 1 to 5, and when r11 and r12 are each 2 or greater, the substituents in parentheses are either the same or different from each other.

[0148] In one exemplary embodiment of this specification, chemical formula 1 is either 1-A-11 or 1-A-12.

[0149] [Chemical Formula 1-A-11]

[0150]

[0151] [Chemical Formula 1-A-12]

[0152]

[0153] In chemical formulas 1-A-11 and 1-A-12,

[0154] La, L1 to L6, Ar1 to Ar4, R1 to R4, l1, l3, l4, l6, r1 to r4, and m are the same as those defined in Chemical Formula 1.

[0155] X1 and X4 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group.

[0156] L11' and L14' may be the same as or different from each other, and each is an independent direct bond; or -O-,

[0157] R11 to R14 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0158] r13 and r14 are each integers from 1 to 4, r11 and r12 are each integers from 1 to 5, and when r11 to r14 are each 2 or greater, the substituents in parentheses are the same or different from each other.

[0159] In one exemplary embodiment of this specification, La is -Lx-A-Ly-; a substituted or unsubstituted divalent dihydroanthracene group; a substituted or unsubstituted tricyclic to decacyclic divalent heterocyclic group comprising O, S, or Si; a substituted or unsubstituted divalent fluorene group; or a substituted or unsubstituted divalent spirodifluorene group.

[0160] In one exemplary embodiment of this specification, La is -Lx-A-Ly-; a substituted or unsubstituted divalent dihydroanthracene group; a substituted or unsubstituted tricyclic to octaneous divalent heterocyclic group comprising O, S, or Si; or a substituted or unsubstituted divalent fluorene group; or a substituted or unsubstituted divalent spirodifluorene group.

[0161] In one exemplary embodiment of this specification, La is -Lx-A-Ly-; a substituted or unsubstituted divalent dihydroanthracene group; a substituted or unsubstituted tricyclic to hexacyclic divalent heterocyclic group comprising O, S, or Si; or a substituted or unsubstituted divalent fluorene group; or a substituted or unsubstituted divalent spirodifluorene group.

[0162] In one exemplary embodiment of this specification, La is any of the following structures.

[0163]

[0164] In the structure,

[0165] Cy1 and Cy2 may be the same as or different from each other, and each is independently a substituted or unsubstituted aromatic ring.

[0166] Y1 and Y2 may be the same as or different from each other, and each is independently O; S; CRaRb; or SiRcRd.

[0167] Ra to Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl.

[0168] R21 to R28 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring.

[0169] y2 is 0 or 1.

[0170] r21 to r24 are each integers from 1 to 4, r25 and r26 are each integers from 1 to 3, r27 and r28 are each integers from 1 to 7, and when r21 to r28 are 2 or greater, the substituents in parentheses are either the same or different from each other.

[0171] This refers to the portion that is bonded to chemical formula 1.

[0172] In one exemplary embodiment of this specification, La is not substituted with curable groups.

[0173] In one exemplary embodiment of this specification, La is a substituted or unsubstituted divalent fluorene group; or a substituted or unsubstituted divalent spirodifluorene group.

[0174] In one exemplary embodiment of this specification, La is any of the following structures.

[0175]

[0176] In the structure,

[0177] Ra and Rb may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl.

[0178] R23 to R30 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0179] r25, r26, r29, and r30 are each integers from 1 to 3; r23 and r24 are each integers from 1 to 4; r27 and r28 are each integers from 1 to 7; and when r23 to r30 are 2 or greater, the substituents in parentheses are either the same or different from each other.

[0180] This refers to the portion that is bonded to chemical formula 1.

[0181] In one exemplary embodiment of this specification, La is -Lx-A-Ly-; a substituted or unsubstituted divalent dihydroanthracene group; or a substituted or unsubstituted divalent heterocyclic group.

[0182] In one exemplary embodiment of this specification, La has the following structure.

[0183]

[0184] In the structure,

[0185] Y2 can be O; S; CRaRb; or SiRcRd.

[0186] Ra to Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl.

[0187] R21 and R22 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring.

[0188] y2 is 0 or 1.

[0189] r21 and r22 are each integers from 1 to 4, and when r21 and r22 are each 2 or greater, the substituents in parentheses are either the same or different from each other.

[0190] This refers to the portion that is bonded to chemical formula 1.

[0191] In one exemplary embodiment of this specification, y2 is 0. In this case, the structure can be constructed by... express.

[0192] In one exemplary embodiment of this specification, y2 is 1. In this case, the structure can be constructed by... express.

[0193] In one exemplary embodiment of this specification, La is a substituted or unsubstituted divalent heterocyclic group.

[0194] In one exemplary embodiment of this specification, La has the following structure.

[0195]

[0196] In the structure,

[0197] Cy1 and Cy2 may be the same as or different from each other, and each is independently a substituted or unsubstituted aromatic ring.

[0198] Y3 can be O; S; or SiRcRd.

[0199] Rc and Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl, and

[0200] This refers to the portion that is bonded to chemical formula 1.

[0201] In one exemplary embodiment of this specification, Cy1 and Cy2 may be the same as or different from each other, and each is independently a substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms.

[0202] In one exemplary embodiment of this specification, Cy1 and Cy2 may be the same as or different from each other, and each is independently a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring.

[0203] In one exemplary embodiment of this specification, Cy1 and Cy2 may be the same as or different from each other, and each is independently a benzene ring; or a naphthalene ring.

[0204] In one exemplary embodiment of this specification, La is any of the following structures.

[0205]

[0206] In the structure,

[0207] Y2 can be O; S; CRaRb; or SiRcRd.

[0208] Y3 can be O; S; or SiRcRd.

[0209] Ra to Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl.

[0210] R21 to R32, R21' and R22' may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups bonded to each other to form a substituted or unsubstituted ring.

[0211] r21 to r24, r21' and r22' are each integers from 1 to 4, r25, r26 and r29 to r32 are each integers from 1 to 3, r27 and r28 are each integers from 1 to 7, and when r21 to r32, r21' and r22' are 2 or greater, the substituents in parentheses are either the same or different from each other, and

[0212] This refers to the portion that is bonded to chemical formula 1.

[0213] In one exemplary embodiment of this specification, La is -Lx-A-Ly-, Lx and Ly may be the same as or different from each other, and each is independently a substituted or unsubstituted arylene, and A is a substituted or unsubstituted divalent dihydroanthracene; a substituted or unsubstituted divalent heterocyclic group; a substituted or unsubstituted divalent fluorene group; or a substituted or unsubstituted divalent spirodifluorene group.

[0214] In one exemplary embodiment of this specification, Lx and Ly may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0215] In one exemplary embodiment of this specification, Lx and Ly may be the same as or different from each other, and each is independently an arylene group having 6 to 30 carbon atoms.

[0216] In one exemplary embodiment of this specification, Lx and Ly are each a substituted or unsubstituted phenylene oxide.

[0217] In one exemplary embodiment of this specification, Lx and Ly are each phenylene oxide.

[0218] In one exemplary embodiment of this specification, A is a substituted or unsubstituted divalent heterocyclic group; a substituted or unsubstituted divalent fluorenyl group; or a substituted or unsubstituted divalent dihydroanthracene group.

[0219] In one exemplary embodiment of this specification, -Lx-A-Ly- is Furthermore, Y2, y2, R21, R22, r21, and r22 are the same as those mentioned above.

[0220] In the structure, when y2 is 0, A can be represented by a divalent fluorene group.

[0221] In the structure, when y2 is 1 and Y2 is CRaRb, A can be represented by a divalent dihydroanthracene group.

[0222] In the structure, when y2 is 1 and Y2 is O; S; or SiRcRd, A can be represented by a divalent heterocyclic group.

[0223] Specifically, -Lx-A-Ly- is any of the following structures.

[0224]

[0225] In one exemplary embodiment of this specification, La is a substituted or unsubstituted divalent fluorene group. Specifically, La is...

[0226] In one exemplary embodiment of this specification, La is a substituted or unsubstituted divalent heterocyclic group. Specifically, La is...

[0227] In one exemplary embodiment of this specification, La is a substituted or unsubstituted divalent spirodifluorene group. Specifically, La is...

[0228] In the structure, Y2, Y3, Ra, Rb, R21 to R32, R21', R22', r21 to r32, r21' and r22' are the same as those mentioned above.

[0229] In one exemplary embodiment of this specification, chemical formula 1 is any one of the following chemical formulas 1-11 to 1-16.

[0230] [Chemical Formula 1-11]

[0231]

[0232] [Chemical Formula 1-12]

[0233]

[0234] [Chemical Formula 1-13]

[0235]

[0236] [Chemical Formula 1-14]

[0237]

[0238] [Chemical Formula 1-15]

[0239]

[0240] [Chemical Formula 1-16]

[0241]

[0242] In chemical formulas 1-11 to 1-16,

[0243] L1 to L6, L11 to L14, Ar1 to Ar4, X1 to X4, R1 to R4, l1, l3, l4, l6, l11 to l14, r1 to r4, and m are the same as those defined in Chemical Formula 1.

[0244] Cy1 and Cy2 may be the same as or different from each other, and each is independently a substituted or unsubstituted aromatic ring.

[0245] Y2 can be O, S, CRaRb, or SiRcRd.

[0246] Y3 can be O, S, or SiRcRd.

[0247] Ra to Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl.

[0248] R21 to R26, R27', R27”, R28', R28”, R29, and R30 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups bonded to each other to form a substituted or unsubstituted ring, and

[0249] r25, r26, r27', r28', r29, and r30 are each integers from 1 to 3, r21 to r24, r27”, and r28” are each integers from 1 to 4, and when r21 to r26, r27', r27”, r28', r28”, r29, and r30 are each 2 or greater, the substituents in parentheses are the same or different from each other.

[0250] In one exemplary embodiment of this specification, chemical formula 1 is any one of the following chemical formulas 1-21 to 1-26.

[0251] [Chemical Formula 1-21]

[0252]

[0253] [Chemical Formula 1-22]

[0254]

[0255] [Chemical Formula 1-23]

[0256]

[0257] [Chemical Formula 1-24]

[0258]

[0259] [Chemical Formula 1-25]

[0260]

[0261] [Chemical Formula 1-26]

[0262]

[0263] In chemical formulas 1-21 to 1-26,

[0264] L1 to L6, L11, L14, Ar1 to Ar4, R1 to R4, l1, l3, l4, l6, l11, l14, r1 to r4, and m are the same as those defined in Chemical Formula 1.

[0265] Cy1 and Cy2 may be the same as or different from each other, and each is independently a substituted or unsubstituted aromatic ring.

[0266] Y2 can be O, S, CRaRb, or SiRcRd.

[0267] Y3 can be O, S, or SiRcRd.

[0268] X1 and X4 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group.

[0269] Ra to Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl.

[0270] R11 and R12 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0271] R21 to R26, R27', R27”, R28', R28”, R29, and R30 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups bonded to each other to form a substituted or unsubstituted ring, and

[0272] r25, r26, r27', r28', r29, and r30 are each integers from 1 to 3, r21 to r24, r27”, and r28” are each integers from 1 to 4, r11 and r12 are each integers from 1 to 5, and when r11, r12, r21 to r26, r27', r27”, r28', r28”, r29, and r30 are each 2 or greater, the substituents in parentheses are the same or different from each other.

[0273] In one exemplary embodiment of this specification, chemical formula 1-21 is any one of the following chemical formulas 1-21-1 to 1-21-5, and the following structures are unsubstituted or substituted with other substituents.

[0274] [Chemical Formula 1-21-1]

[0275]

[0276] [Chemical Formula 1-21-2]

[0277]

[0278] [Chemical Formula 1-21-3]

[0279]

[0280] [Chemical Formula 1-21-4]

[0281]

[0282] [Chemical Formula 1-21-5]

[0283]

[0284] In chemical formulas 1-21-1 to 1-21-5, L1 to L6, L11, L14, X1, X4, Ar1 to Ar4, R1 to R4, R11, R12, l1, l3, l4, l6, l11, l14, r1 to r4, r11, r12 and m are the same as those defined in chemical formula 1-21.

[0285] In one exemplary embodiment of this specification, when any one or more adjacent groups of formulas 1-21 and 22 are bonded to each other to form a ring, formula 1 is represented by any one of formulas 1-21-2 to 1-21-5.

[0286] In one exemplary embodiment of this specification, chemical formula 1-22 is any one of the following chemical formulas 1-22-1 to 1-22-5, and the following structures are unsubstituted or substituted with other substituents.

[0287] [Chemical Formula 1-22-1]

[0288]

[0289] [Chemical Formula 1-22-2]

[0290]

[0291] [Chemical Formula 1-22-3]

[0292]

[0293] [Chemical Formula 1-22-4]

[0294]

[0295] [Chemical Formula 1-22-5]

[0296]

[0297] In chemical formulas 1-22-1 to 1-22-5, Y2, L1 to L6, L11, L14, X1, X4, Ar1 to Ar4, R1 to R4, R11, R12, l1, l3, l4, l6, l11, l14, r1 to r4, r11, r12, and m are the same as those defined in chemical formula 1-22.

[0298] In one exemplary embodiment of this specification, when any one or more adjacent groups of formulas 1-22, R21 and R22, are bonded to each other to form a ring, formula 1 is represented by any one of formulas 1-22-2 to 1-22-5.

[0299] In one exemplary embodiment of this specification, the additional substituents substituted in chemical formulas 1-21-1 to 1-21-5 and 1-22-1 to 1-22-5 are selected from one or more of the following: deuterium; halogen groups; substituted or unsubstituted alkyl groups; substituted or unsubstituted alkoxy groups; substituted or unsubstituted aryl groups; and substituted or unsubstituted heterocyclic groups.

[0300] In one exemplary embodiment of this specification, chemical formula 1 is any one of chemical formulas 1-21-1 to 1-21-5, 1-22-1 to 1-22-5, and 1-23 to 1-26, and said chemical formula is unsubstituted or substituted with other substituents.

[0301] Specifically, the following structures of chemical formulas 1-21-1 to 1-21-5 and 1-22-1 to 1-22-5 are either unsubstituted or substituted with other substituents.

[0302]

[0303] In the structure, Y2 is the same as described above.

[0304] In one exemplary embodiment of this specification, La is any of the following structures, and the following structures are unsubstituted or substituted with other substituents.

[0305]

[0306] In the structure,

[0307] Ra to Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl, and

[0308] ------ is the part connected to chemical formula 1.

[0309] In one exemplary embodiment of this specification, the additional substituent is selected from one or more of the following: deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryl group; and substituted or unsubstituted heterocyclic group.

[0310] In one exemplary embodiment of this specification, the additional substituents are deuterium; halogen groups; substituted or unsubstituted alkyl groups; substituted or unsubstituted alkoxy groups; substituted or unsubstituted aryl groups; or substituted or unsubstituted heterocyclic groups.

[0311] In one exemplary embodiment of this specification, the additional substituents are deuterium; halogen groups; alkyl; alkoxy; aryl; or heterocyclic groups.

[0312] In one exemplary embodiment of this specification, La is any of the structures, and the structure is not replaced.

[0313] In one exemplary embodiment of this specification, Ra to Rd may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0314] In one exemplary embodiment of this specification, Ra to Rd may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0315] In one exemplary embodiment of this specification, Ra to Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; alkyl; or aryl.

[0316] In one exemplary embodiment of this specification, Ra to Rd may be the same as or different from each other, and each is independently an alkyl or aryl group.

[0317] In one exemplary embodiment of this specification, Ra to Rd may be the same as or different from each other, and each is independently an alkyl group having 1 to 30 carbon atoms; or an aryl group having 6 to 30 carbon atoms.

[0318] In one exemplary embodiment of this specification, Ra to Rd may be the same as or different from each other, and each is independently methyl; ethyl; propyl; butyl; pentyl; hexyl; phenyl; biphenyl; or naphthyl.

[0319] In one exemplary embodiment of this specification, Ra to Rd may be the same as or different from each other, and each is independently methyl; ethyl; butyl; hexyl; or phenyl.

[0320] In one exemplary embodiment of this specification, the compound of Formula 1 is either unsubstituted or substituted with F.

[0321] In one exemplary embodiment of this specification, chemical formula 1 is the following chemical formula 1-B.

[0322] [Chemical Formula 1-B]

[0323]

[0324] In chemical formula 1-B,

[0325] La, L1 to L6, L11 to L14, X1 to X4, Ar1 to Ar4, R1 to R4, m, r1 to r4, l1, l3, l4, l6, and l11 to l14 are the same as those defined in Chemical Formula 1.

[0326] m1 is the maximum number of substituents that can bond to Ar1, ranging from 0.

[0327] m2 is the maximum number of substituents that can bond to Ar2, ranging from 0.

[0328] m3 is the maximum number of substituents that can bond to Ar3 from 0, and

[0329] m4 is the maximum number of substituents that can be bonded to Ar4, ranging from 0 to the maximum number of substituents that can be bonded to Ar4.

[0330] In one exemplary embodiment of this specification, chemical formula 1 is the following chemical formula 1-B-1.

[0331] [Chemical Formula 1-B-1]

[0332]

[0333] In chemical formula 1-B-1,

[0334] La, L1 to L6, L11, L14, Ar1 to Ar4, R1 to R4, m, r1 to r4, l1, l3, l4, l6, l11, and l14 are the same as those defined in Formula 1.

[0335] X1 and X4 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group.

[0336] R11 and R12 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0337] m1 is the maximum number of substituents that can bond to Ar1, ranging from 0.

[0338] m2 is the maximum number of substituents that can bond to Ar2, ranging from 0.

[0339] m3 is the maximum number of substituents that can bond to Ar3, ranging from 0.

[0340] m4 is the maximum number of substituents that can bond to Ar4, ranging from 0.

[0341] r11 and r12 are each integers from 1 to 5, and when r11 and r12 are 2 or greater, the substituents in parentheses are either the same or different from each other.

[0342] m5 and m6 are each integers from 0 to 5, r11+m5 is 5 or less, and r12+m6 is 5 or less.

[0343] In this specification, the maximum number of substituents that can be bonded to each of Ar1 to Ar4 is the number of hydrogen atoms that can be bonded to each of Ar1 to Ar4. For example, when Ar1 is phenyl, m1 is an integer from 0 to 5, and when Ar1 is biphenyl, m1 is an integer from 0 to 9.

[0344] In one exemplary embodiment of this specification, the compound of Formula 1 may not be substituted with F. Specifically, m1 to m6 may each be 0.

[0345] In one exemplary embodiment of this specification, m1+m2+m3+m4+m5+m6 is 0 or greater.

[0346] In one exemplary embodiment of this specification, m1+m2+m3+m4+m5+m6 are integers from 0 to 50.

[0347] In one exemplary embodiment of this specification, m1+m2+m3+m4+m5+m6 are integers from 0 to 30.

[0348] In one exemplary embodiment of this specification, m1+m2+m3+m4+m5+m6 are integers from 0 to 10.

[0349] In one exemplary embodiment of this specification, m1 to m4 are each an integer from 0 to 11.

[0350] In one exemplary embodiment of this specification, m1 to m4 are each an integer from 0 to 9.

[0351] In one exemplary embodiment of this specification, m1 to m4 are each an integer from 0 to 7.

[0352] In one exemplary embodiment of this specification, the compound of formula 1 may be substituted with one or more F atoms. Specifically, at least one of m1 to m6 may be 1 or greater.

[0353] In one exemplary embodiment of this specification, r11+m5 is an integer from 1 to 5, and r12+m6 is an integer from 1 to 5.

[0354] In one exemplary embodiment of this specification, one to six of m1 to m6 are 1 or greater.

[0355] In one exemplary embodiment of this specification, both m1 to m6 are 1 or greater.

[0356] In one exemplary embodiment of this specification, four of m1 to m6 are 1 or greater.

[0357] In one exemplary embodiment of this specification, six of m1 to m6 are 1 or greater.

[0358] In one exemplary embodiment of this specification, m1+m2+m3+m4+m5+m6 is 1 or greater.

[0359] In one exemplary embodiment of this specification, m1+m2+m3+m4+m5+m6 are integers from 1 to 50.

[0360] In one exemplary embodiment of this specification, m1+m2+m3+m4+m5+m6 are integers from 1 to 30.

[0361] In one exemplary embodiment of this specification, m1+m2+m3+m4+m5+m6 are integers from 1 to 10.

[0362] In one exemplary embodiment of this specification, m1+m2+m3+m4+m5+m6 are integers from 2 to 10.

[0363] In one exemplary embodiment of this specification, m1 to m4 are each an integer from 1 to 11.

[0364] In one exemplary embodiment of this specification, m1 to m4 are each an integer from 1 to 9.

[0365] In one exemplary embodiment of this specification, m1 to m4 are each an integer from 1 to 7.

[0366] In one exemplary embodiment of this specification, m5 and m6 are each integers from 1 to 5.

[0367] In one exemplary embodiment of this specification, l1, l3, l4 and l6 are 0, and chemical formula 1 is represented by the following chemical formula 1-C.

[0368] [Chemical Formula 1-C]

[0369]

[0370] In chemical formula 1-C,

[0371] La, L2, L5, L11 to L14, R1 to R4, Ar1 to Ar4, X1 to X4, r1 to r4, l11 to l14 and m are those defined in chemical formula 1.

[0372] In one exemplary embodiment of this specification, when La is a divalent fluorenyl or a divalent spirodifluorenyl, chemical formula 1 is represented by chemical formula 1-C.

[0373] In one exemplary embodiment of this specification, when La is a divalent fluorenyl or a divalent spirodifluorenyl, chemical formula 1 is represented by any of the following chemical formulas 1-C-1 to 1-C-6.

[0374] [Chemical formula 1-C-1]

[0375]

[0376] [Chemical formula 1-C-2]

[0377]

[0378] [Chemical formula 1-C-3]

[0379]

[0380] [Chemical formula 1-C-4]

[0381]

[0382] [Chemical Formula 1-C-5]

[0383]

[0384] [Chemical formula 1-C-6]

[0385]

[0386] In chemical formulas 1-C-1 to 1-C-6,

[0387] L2, L5, Ar1 to Ar4, R1 to R4, r1 to r4, and m are the same as those defined in Chemical Formula 1.

[0388] X1 and X4 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group.

[0389] L11' and L14' may be the same as or different from each other, and each is an independent direct bond; or -O-,

[0390] R11, R12, R21 to R26, R27', R27”, R28' and R28” are identical or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0391] r21, r22, r25, r26, r27', and r28' are each integers from 1 to 3, r23, r24, r27', and r28' are each integers from 1 to 4, r11 and r12 are each integers from 1 to 5, and when r11, r12, r21 to r26, r27', r28', r27', and r28' are each 2 or greater, the substituents in parentheses are the same or different from each other.

[0392] In one exemplary embodiment of this specification, when La is When chemical formula 1 is used, it is represented by the following chemical formula 1-D1.

[0393] [Chemical Formula 1-D1]

[0394]

[0395] In chemical formula 1-D1,

[0396] L1 to L6, L11 to L14, X1 to X4, Ar1 to Ar4, R1 to R4, r1 to r4, l11 to l14, m, l1, l3, l4 and l6 are the same as those defined in Chemical Formula 1.

[0397] Y2 can be O; S; CRaRb; or SiRcRd.

[0398] R21 and R22 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0399] y2 is 0 or 1, and

[0400] r21 and r22 are each integers from 1 to 4, and when r21 and r22 are each 2 or greater, the substituents in parentheses are either the same or different from each other.

[0401] In one exemplary embodiment of this specification, chemical formula 1 is the following chemical formula 1-D2.

[0402] [Chemical Formula 1-D2]

[0403]

[0404] In chemical formula 1-D2,

[0405] L1 to L6, L11, L14, Ar1 to Ar4, R1 to R4, r1 to r4, l11, l14, m, l1, l3, l4, and l6 are the same as those defined in Formula 1.

[0406] X1 and X4 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group.

[0407] Y2 can be O; S; CRaRb; or SiRcRd.

[0408] R11, R12, R21, and R22 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0409] r11 and r12 are each integers from 1 to 5, r21 and r22 are each integers from 1 to 4, and when r11, r12, r21 and r22 are each 2 or greater, the substituents in parentheses are the same or different from each other.

[0410] In one exemplary embodiment of this specification, chemical formula 1-D1 is any one of the following chemical formulas 1-D3 to 1-D5.

[0411] [Chemical formula 1-D3]

[0412]

[0413] [Chemical Formula 1-D4]

[0414]

[0415] [Chemical Formula 1-D5]

[0416]

[0417] In chemical formulas 1-D3 to 1-D5

[0418] L1 to L6, L11, L14, Ar1 to Ar4, R1, R4, R21, R22, l1, l3, l4, l6, l11, l14, Y2, y2, r1, r4, r21, r22, and m are the same as those defined in chemical formula 1-D1.

[0419] X1 and X4 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group.

[0420] R11 and R12 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0421] r11 and r12 are each integers from 1 to 5, r21 and r22 are each integers from 1 to 4, and when r11, r12, r21 and r22 are each 2 or greater, the substituents in parentheses are the same or different from each other.

[0422] In one exemplary embodiment of this specification, Ar1 to Ar4 may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0423] In one exemplary embodiment of this specification, Ar1 to Ar4 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0424] In one exemplary embodiment of this specification, Ar1 to Ar4 may be the same as or different from each other, and each is independently a group connected to any one or more of the following structures, which are unsubstituted or substituted with other substituents.

[0425]

[0426] In the structure,

[0427] Z2 to Z14 may be the same as or different from each other, and each is independently S; O; CRjRk; SiRlRm; or NRn.

[0428] Rj to Rn may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group.

[0429] a3 and a4 are each integers from 1 to 5, and when a3 and a4 are each 2 or greater, the structures within the parentheses are either the same or different from each other.

[0430] ------ is the part that is bonded to chemical formula 1.

[0431] In one exemplary embodiment of this specification, the additional substituents substituted in the Ar1 to Ar4 structures are selected from one or more of the following: deuterium; halogen groups; substituted or unsubstituted alkyl groups; substituted or unsubstituted alkoxy groups; substituted or unsubstituted aryl groups; and substituted or unsubstituted heterocyclic groups.

[0432] In one exemplary embodiment of this specification, Ar1 to Ar4 may be the same as or different from each other, and each is independently a group connected to any one or more of the following structures, which are unsubstituted or substituted with other substituents.

[0433]

[0434] In the structure,

[0435] Z2, Z5 to Z7, Z10 to Z12, a3, a4, and other substituents are the same as those mentioned above.

[0436] In one exemplary embodiment of this specification, Ar1 to Ar4 may be the same as or different from each other, and each is independently an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a halogen group, alkyl group or heterocyclic group; or an unsubstituted or substituted with a halogen group or alkyl group having 2 to 30 carbon atoms.

[0437] In one exemplary embodiment of this specification, Ar1 to Ar4 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiopheneyl.

[0438] In one exemplary embodiment of this specification, Ar1 to Ar4 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiopheneyl.

[0439] In one exemplary embodiment of this specification, Ar1 to Ar4 may be the same as or different from each other, and each is independently an unsubstituted or substituted phenyl group with deuterium, halogen group, alkyl or heterocyclic group; an unsubstituted or substituted biphenyl group with deuterium, halogen group, alkyl or heterocyclic group; an unsubstituted or substituted naphthyl group with deuterium, halogen group, alkyl or heterocyclic group; an unsubstituted or substituted dibenzofuranyl group with deuterium, halogen group or alkyl group; or an unsubstituted or substituted dibenzothiophenyl group with deuterium, halogen group or alkyl group.

[0440] In one exemplary embodiment of this specification, Ar1 to Ar4 are any of the following structures, and the following structures are unsubstituted or substituted with other substituents.

[0441]

[0442] In the structure, Z2, ------ and other substituents are the same as those mentioned above.

[0443] In one exemplary embodiment of this specification, the additional substituents substituted in the Ar1 to Ar4 structures are selected from one or more of the following: deuterium; halogen groups; substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms; substituted or unsubstituted aryl groups having 6 to 30 carbon atoms; and substituted or unsubstituted heterocyclic groups having 2 to 30 carbon atoms.

[0444] In one exemplary embodiment of this specification, the additional substituents substituted in the Ar1 to Ar4 structures are halogen groups; alkyl groups; or heterocyclic groups.

[0445] In one exemplary embodiment of this specification, the structure is unsubstituted or substituted with halogen groups, alkyl groups, or heterocyclic groups.

[0446] In one exemplary embodiment of this specification, -Ar1-(F) m1 -Ar2-(F) m2 -Ar3-(F) m3 and -Ar4-(F) m4 It can be represented by any of the following structures, and the following structures are either unsubstituted or substituted with other substituents.

[0447]

[0448] In the structure,

[0449] Z2 and ------ are the same as those mentioned above, and

[0450] ma, mb, and md are integers from 0 to 5; mc, me, mf, and mj are integers from 0 to 4; and mg, mh, and mi are integers from 0 to 7.

[0451] In one exemplary embodiment of this specification, -Ar1-(F) m1 -Ar2-(F) m2 -Ar3-(F) m3 and -Ar4-(F) m4 The additional substituents in the structure are selected from one or more of the following: deuterium; halogen group; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryl; and substituted or unsubstituted heterocyclic group.

[0452] In one exemplary embodiment of this specification, the structure is either unsubstituted or alkyl-substituted.

[0453] In one exemplary embodiment of this specification, ma, mb, and md are integers from 1 to 5, mc, me, mf, and mj are integers from 1 to 4, and mg, mh, and mi are integers from 1 to 7.

[0454] In one exemplary embodiment of this specification, Z2 is O or S.

[0455] In one exemplary embodiment of this specification, L1 to L6 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

[0456] In one exemplary embodiment of this specification, L1 to L6 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0457] In one exemplary embodiment of this specification, L1 to L6 may be the same as or different from each other, and each is independently a group connected to any one or more of the following structures, which are unsubstituted or substituted with other substituents.

[0458]

[0459] In the structure,

[0460] Z1 is S; O; CreRf; SiRgRh; or NRi.

[0461] Re to Ri may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group.

[0462] a1 and a2 are each integers from 1 to 5, and when a1 to a2 are each 2 or greater, the structures within the parentheses are either the same or different from each other.

[0463] ------ is the part that is bonded to chemical formula 1.

[0464] In one exemplary embodiment of this specification, the additional substituents substituted in the L1 to L6 structures are selected from one or more of the following: deuterium; halogen groups; substituted or unsubstituted alkyl groups; substituted or unsubstituted alkoxy groups; substituted or unsubstituted aryl groups; and substituted or unsubstituted heterocyclic groups.

[0465] In one exemplary embodiment of this specification, the additional substituents substituted in the L1 to L6 structures are selected from one or more of the following: deuterium; halogen groups; substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms; substituted or unsubstituted aryl groups having 6 to 30 carbon atoms; and substituted or unsubstituted heterocyclic groups having 2 to 30 carbon atoms.

[0466] In one exemplary embodiment of this specification, the additional substituents substituted in the L1 to L6 structures are alkyl or aryl groups.

[0467] In one exemplary embodiment of this specification, the structure is unsubstituted or substituted with alkyl or aryl groups.

[0468] In one exemplary embodiment of this specification, L1 to L6 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; a substituted or unsubstituted terphenylene; a substituted or unsubstituted fluorene; a substituted or unsubstituted divalent spirofluorene; a substituted or unsubstituted phenanthroline; a substituted or unsubstituted naphthylene; or a substituted or unsubstituted binatyl; or a group connected to two or more of the substituents.

[0469] In one exemplary embodiment of this specification, L1 to L6 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; a substituted or unsubstituted terphenylene; or a substituted or unsubstituted divalent spirodifluorene.

[0470] In one exemplary embodiment of this specification, L1 to L6 may be the same as or different from each other, and each is independently an unsubstituted or alkyl- or aryl-substituted phenylene; an unsubstituted or alkyl- or aryl-substituted biphenylene; an unsubstituted or alkyl- or aryl-substituted terphenylene; or an unsubstituted or alkyl- or aryl-substituted divalent spirodifluorene.

[0471] In one exemplary embodiment of this specification, L1, L3, L4 and L6 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenylene.

[0472] In one exemplary embodiment of this specification, L1, L3, L4 and L6 may be the same as or different from each other, and each is independently phenylene.

[0473] In one exemplary embodiment of this specification, l1, l3, l4 and l6 are each 0 or 1.

[0474] In one exemplary embodiment of this specification, when l1, l3, l4, and l6 are 0, L1, L3, L4, and L6 can be represented by direct keys.

[0475] In one exemplary embodiment of this specification, l1, l3, l4 and l6 are each 0.

[0476] In one exemplary embodiment of this specification, l1, l3, l4 and l6 are each 1.

[0477] In one exemplary embodiment of this specification, l1 and l6 are 0, and l3 and l4 are 1.

[0478] In one exemplary embodiment of this specification, l1 and l6 are 1, and l3 and l4 are 0.

[0479] In one exemplary embodiment of this specification, L2 and L5 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; a substituted or unsubstituted terphenylene; a substituted or unsubstituted fluorene; a substituted or unsubstituted phenanthroline; a substituted or unsubstituted naphthylene; or a substituted or unsubstituted binatylene; or a group connected to two or more of the substituents.

[0480] In one exemplary embodiment of this specification, L2 and L5 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; a substituted or unsubstituted terphenylene; or a substituted or unsubstituted divalent spirodifluorene.

[0481] In one exemplary embodiment of this specification, L2 and L5 may be the same as or different from each other, and each is independently phenylene; biphenylene; terphenylene; or divalent spirodifluorene.

[0482] In one exemplary embodiment of this specification, L11 and L14 may be the same as or different from each other, and each is independently a direct bond; -O-; a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0483] In one exemplary embodiment of this specification, L11 and L14 may be the same as or different from each other, and each is independently a direct bond; -O-; methylene; substituted or unsubstituted ethylene; substituted or unsubstituted propylene; or substituted or unsubstituted phenylene.

[0484] In one exemplary embodiment of this specification, L11 and L14 may be the same as or different from each other, and each is independently a direct bond; -O-; methylene; ethylene; propylene; or phenylene.

[0485] In one exemplary embodiment of this specification, the photocurable group or thermosetting group is any of the following structures.

[0486]

[0487] In the structure,

[0488] L50 to L57 may be the same as or different from each other, and each is independently a direct bond; -O-; or a substituted or unsubstituted alkylene group.

[0489] l50 to l57 are each integers from 1 to 5, and when l50 to l57 are each 2 or greater, the structures within the parentheses are either the same or different from each other.

[0490] ------ is the part that is bonded to chemical formula 1.

[0491] In one exemplary embodiment of this specification, the photocurable group or thermosetting group is L54, L56, and L57 may be the same as or different from each other, and each is independently a direct bond; -O-; or a substituted or unsubstituted alkylene group, each of l54, l56, and l57 being an integer from 1 to 5, and when each of l54, l56, and l57 is 2 or greater, the structures in parentheses may be the same as or different from each other.

[0492] In one exemplary embodiment of this specification, the photocurable group or thermosetting group is any of the following structures.

[0493]

[0494] In one exemplary embodiment of this specification, R1 to R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group.

[0495] In one exemplary embodiment of this specification, R1 to R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0496] In one exemplary embodiment of this specification, R1 to R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0497] In one exemplary embodiment of this specification, R1 to R4 are each hydrogen, deuterium, or a halogen group.

[0498] In one exemplary embodiment of this specification, R1 to R4 are each hydrogen; or deuterium.

[0499] In one exemplary embodiment of this specification, R11 and R12 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0500] In one exemplary embodiment of this specification, R11 and R12 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; or an alkyl group having 1 to 10 carbon atoms.

[0501] In one exemplary embodiment of this specification, when m is 1, chemical formula 1 is represented by the following chemical formulas 1-31.

[0502] [Chemical Formula 1-31]

[0503]

[0504] In chemical formula 1-31,

[0505] La, L1 to L6, L11 to L14, X1 to X4, Ar1 to Ar4, R1 to R4, l1, l3, l4, l6, l11 to l14 and r1 to r4 are the same as those defined in Formula 1.

[0506] In one exemplary embodiment of this specification, chemical formula 1-31 is represented by the following chemical formula 1-31-1.

[0507] [Chemical Formula 1-31-1]

[0508]

[0509] In chemical formula 1-31-1,

[0510] La, L1 to L6, L11, L14, Ar1 to Ar4, R1 to R4, l1, l3, l4, l6, l11, l14 and r1 to r4 are the same as those defined in Chemical Formula 1.

[0511] X1 and X4 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group.

[0512] R11 and R12 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0513] r11 and r12 are each integers from 1 to 5, and when r11 and r12 are each 2 or greater, the substituents in parentheses are either the same or different from each other.

[0514] In one exemplary embodiment of this specification, when m is 2 to 10, the following structure is repeated as many times as the number of m.

[0515]

[0516] In this structure, L1 to L3, l1, l3, La, Ar1, and Ar2 are the same as those defined in Formula 1, and * represents the connection point in the compound.

[0517] For example, when m is 2, chemical formula 1 can be represented by the following chemical formula 1-32.

[0518] [Chemical Formula 1-32]

[0519]

[0520] In chemical formula 1-32,

[0521] La, L1 to L6, L11 to L14, X1 to X4, Ar1 to Ar4, R1 to R4, l1, l3, l4, l6, l11 to l14 and r1 to r4 are the same as those defined in Formula 1.

[0522] In one exemplary embodiment of this specification, chemical formula 1-32 is represented by the following chemical formula 1-32-1.

[0523] [Chemical Formula 1-32-1]

[0524]

[0525] In chemical formula 1-32-1,

[0526] La, L1 to L6, L11, L14, Ar1 to Ar4, R1 to R4, l1, l3, l4, l6, l11, l14 and r1 to r4 are the same as those defined in Chemical Formula 1.

[0527] X1 and X4 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group.

[0528] R11 and R12 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0529] r11 and r12 are each integers from 1 to 5, and when r11 and r12 are each 2 or greater, the substituents in parentheses are either the same or different from each other.

[0530] In one exemplary embodiment of this specification, when n is 2 or greater, the structures in parentheses may be the same or different from each other.

[0531] In one exemplary embodiment of this specification, when n is 2 or greater, the structures within the parentheses are identical to each other.

[0532] In one exemplary embodiment of this specification, chemical formula 1 is any of the following structures.

[0533]

[0534]

[0535]

[0536]

[0537]

[0538] In one exemplary embodiment of this specification, chemical formula 1 is any of the following structures.

[0539]

[0540]

[0541]

[0542]

[0543]

[0544] In one exemplary embodiment of this specification, chemical formula 1 is any of the following structures.

[0545]

[0546]

[0547]

[0548]

[0549] In the structure, hydrogen can be replaced by deuterium.

[0550] In one exemplary embodiment of this specification, the compound is deuterated by 10% or more.

[0551] In this specification, "deuteration" means that the available hydrogen in a compound is replaced by deuterium.

[0552] In this specification, N% deuteration means that N% of the available hydrogens in the corresponding structure are replaced by deuterium. For example, 50% deuteration of a phenyl means that three of the six hydrogens of the phenyl are replaced by deuterium.

[0553] In this specification, the degree of deuteration can be determined by known methods such as nuclear magnetic resonance spectroscopy (NMR spectroscopy). 1 Determined by HNMR or GC / MS.

[0554] In one exemplary embodiment of this specification, the compound is deuterated by 10% to 100%.

[0555] In one exemplary embodiment of this specification, the compound is deuterated by 10% to 90%.

[0556] In one exemplary embodiment of this specification, the compound is deuterated by 20% or more.

[0557] In one exemplary embodiment of this specification, the compound is deuterated by 20% to 100%.

[0558] In one exemplary embodiment of this specification, the compound is deuterated by 20% to 80%.

[0559] The compound according to an exemplary embodiment of this specification can be prepared by the preparation method described below.

[0560] For example, compounds of Formula 1 can be prepared as a core structure as shown in the following reaction scheme, and can be prepared by changing the number of linking groups and / or chains in the following reaction scheme. Furthermore, compounds of Formula 1 can be prepared by a Buchwald-Hartwig amination reaction. In the following reaction schemes, substituents can be bonded by methods known in the art, and the type and position of the substituents or the number of substituents can be changed according to techniques known in the art.

[0561] <Reaction Protocol>

[0562]

[0563] In the reaction scheme, La, L1 to L6, L11 to L14, X1 to X4, Ar1 to Ar4, R1, R4, m, l1, l3, l4, l6, l11 to l14, r1 and r4 are the same as those defined in Formula 1.

[0564] This specification provides coating compositions comprising compounds of chemical formula 1 above.

[0565] In one exemplary embodiment of this specification, the coating composition further comprises a solvent. In one exemplary embodiment of this specification, the coating composition comprises a compound of Formula 1 and a solvent.

[0566] In one exemplary embodiment of this specification, the coating composition may be in a liquid phase. "Liquid phase" means that the composition is liquid at room temperature under atmospheric pressure.

[0567] In one exemplary embodiment of this specification, when the coating composition is applied to the organic material layer, a solvent that will not dissolve the material in the underlying layer is used. Therefore, it has the advantage that the organic material layer can be introduced via a solution method.

[0568] In one exemplary embodiment of this specification, solvent resistance is improved during heat treatment after coating because the compound contains photocurable or thermosetting groups. That is, the compound crosslinks and / or cures after coating and therefore does not dissolve in a particular solvent.

[0569] For example, even if a coating composition is prepared by using a solvent to dissolve the compound and the layer is manufactured by a solution method, the layer can be resistant to the same solvent when cured by heat treatment.

[0570] Therefore, when an organic material layer is formed by using the compound and then a heat treatment process is performed, a solution method can be used when applying another organic material layer.

[0571] For example, when the coating composition is applied to a hole injection layer, it has the advantage that, during the manufacture of the upper layer (hole transport layer, etc.), the upper layer can be introduced by a solution method using a specific solvent to which the cured coating composition exhibits resistance.

[0572] In one exemplary embodiment of this specification, the solvent included in the coating composition is a solvent for dissolving the compound. Examples of solvents include: chlorine-based solvents, such as chloroform, dichloromethane, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether-based solvents, such as tetrahydrofuran and dichlorobenzene. Alkanes; aromatic hydrocarbon-based solvents, such as toluene, xylene, trimethylbenzene, and mesitylene; ketone-based solvents, such as acetone, methyl ethyl ketone, and cyclohexanone; ester-based solvents, such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; polyols, such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerol, and 1,2-hexanediol, and their derivatives; alcohol-based solvents, such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide-based solvents, such as dimethyl sulfoxide; amide-based solvents, such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate-based solvents, such as methyl benzoate, butyl benzoate, and 3-phenoxybenzoate; and solvents such as tetrahydronaphthalene, but any solvent may be used as long as it can dissolve or disperse the compound according to an exemplary embodiment of this specification, and is not limited thereto.

[0573] In one exemplary embodiment of this specification, the solvent may be used alone or in a mixture of two or more solvents.

[0574] In one exemplary embodiment of this specification, the coating composition does not further contain p-type doped material.

[0575] In one exemplary embodiment of this specification, the coating composition further comprises a p-type doped material.

[0576] In this specification, p-type doped material means a material that allows the host material to have p-type semiconductor properties. p-type semiconductor properties refer to the properties of injecting or transporting holes at the highest occupied molecular orbital (HOMO) level, i.e., the properties of a material with high hole conductivity.

[0577] In one exemplary embodiment of this specification, the p-type doped material may be any of the following structures, but is not limited thereto.

[0578]

[0579] In this specification, any p-type doped material that allows the material to have p-type semiconductor properties is sufficient, and one, two or more of them can be used, and there is no limitation on their type.

[0580] In one exemplary embodiment of this specification, the p-type dopant content, based on the compound of Formula 1, is from 0 wt% to 500 wt%. Specifically, the p-type dopant content, based on the compound of Formula 1, is from 100 wt% to 400 wt%.

[0581] In one exemplary embodiment of this specification, the p-type dopant is included in an amount from 0% to 50% by weight, based on the total solids content of the coating composition. In one exemplary embodiment of this specification, it is preferred that the p-type dopant is included in an amount from 1% to 50% by weight, based on the total solids content of the coating composition, and more preferably, it is included in an amount from 10% to 30% by weight, based on the total solids content of the coating composition.

[0582] In another exemplary embodiment, the coating composition further comprises: a monomolecule containing functional groups that can be crosslinked by heat or light; or a monomolecule containing end groups capable of forming a polymer by heat.

[0583] In one exemplary embodiment of this specification, a monomolecule containing functional groups that can be crosslinked by heat or light, or a monomolecule containing end groups that can form a polymer by heat, may be a compound with a molecular weight of 3,000 g / mol or less.

[0584] In one exemplary embodiment of this specification, a monomolecule containing a functional group that can be crosslinked by heat or light, or a monomolecule containing an end group that can form a polymer by heat, may mean a monomolecule in which the functional group that can be crosslinked by heat or light or the end group that can form a polymer by heat replaces the monomolecule in aryl (e.g., phenyl, biphenyl, fluorene, and naphthalene), arylamine, or fluorene.

[0585] In one exemplary embodiment of this specification, the viscosity of the coating composition at room temperature is 2 cP to 15 cP. Specifically, the viscosity of the coating composition is 2 cP to 10 cP. When the above viscosity is met, the device is easy to manufacture.

[0586] Viscosity is measured at 25°C using an Ubbelohde viscometer after the polymer to be measured is dissolved in chloroform at a concentration of 0.5 g / dl.

[0587] An exemplary embodiment of this specification provides an organic light-emitting device formed by using the coating composition.

[0588] An exemplary embodiment of this specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic material layer having one or more layers, including a light-emitting layer, disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain the coating composition or a cured product thereof. In this case, the cured product of the coating composition is in a state in which the coating composition is cured by heat treatment or light treatment.

[0589] In one exemplary embodiment of this specification, the organic material layer comprising the coating composition or its cured product is a hole transport layer or a hole injection layer.

[0590] In one exemplary embodiment of this specification, the organic material layer comprising the coating composition or its cured product is an electron transport layer or an electron injection layer.

[0591] In one exemplary embodiment of this specification, the organic material layer comprising the coating composition or its cured product is a light-emitting layer.

[0592] In one exemplary embodiment of this specification, the organic material layer comprising the coating composition or its cured product is a light-emitting layer, and the light-emitting layer comprises a compound of formula 1 as the body of the light-emitting layer.

[0593] In one exemplary embodiment of this specification, the organic material layer comprising the coating composition or its cured product is a light-emitting layer, and the light-emitting layer comprises a compound of Formula 1 as a dopant for the light-emitting layer.

[0594] In one exemplary embodiment of this specification, the organic light-emitting device includes one or more layers selected from the following: a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, a layer that simultaneously transports and injects holes, and a layer that simultaneously transports and injects electrons.

[0595] In one exemplary embodiment of this specification, the first electrode is an anode and the second electrode is a cathode.

[0596] According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

[0597] In another exemplary embodiment, the organic light-emitting device can be a normal type of organic light-emitting device in which an anode, an organic material layer having one or more layers, and a cathode are sequentially stacked on a substrate.

[0598] In yet another exemplary embodiment, the organic light-emitting device may be an inverted organic light-emitting device in which a cathode, an organic material layer having one or more layers, and an anode are sequentially stacked on a substrate.

[0599] The organic material layer of the organic light-emitting device described in this specification can be a single-layer structure, or it can be a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention can have a structure comprising a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects holes, and a layer that simultaneously transports and injects electrons as organic material layers. However, the structure of the organic light-emitting device is not limited to this, and it can include fewer organic material layers.

[0600] For example, Figure 1 The structure of an organic light-emitting device according to an exemplary embodiment of this specification is illustrated below.

[0601] Figure 1 An example is shown of an organic light-emitting device in which an anode 201, a hole injection layer 301, a hole transport layer 401, a light-emitting layer 501, an electron transport and injection layer 601, and a cathode 701 are sequentially stacked on a substrate 101.

[0602] Figure 1 Organic light-emitting devices are illustrated, but the structure of the organic light-emitting devices of the present invention is not limited thereto.

[0603] When an organic light-emitting device comprises multiple layers of organic materials, the organic material layers can be formed from the same material or different materials.

[0604] The organic light-emitting devices of the present invention can be stacked as the structures shown in the following examples.

[0605] (1) Anode / hole transport layer / light-emitting layer / cathode

[0606] (2) Anode / hole injection layer / hole transport layer / light emission layer / cathode

[0607] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0608] (4) Anode / Hole transport layer / Light emission layer / Electron transport layer / Cathode

[0609] (5) Anode / Hole transport layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0610] (6) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0611] (7) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0612] (8) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0613] (9) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0614] (10) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0615] (11) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0616] (12) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0617] (13) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0618] (14) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Cathode

[0619] (15) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0620] (16) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Cathode

[0621] (17) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0622] (18) Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron injection layer and transport layer / Cathode

[0623] In the structure, the “electron transport layer / electron injection layer” can be replaced by “electron transport and injection layer” or “layer that simultaneously transports and injects electrons”.

[0624] For example, the organic light-emitting device of the present invention can be stacked as a structure such as “anode / hole injection layer / hole transport layer / light-emitting layer / electron transport and injection layer / cathode”, wherein the electron transport layer / electron injection layer of (7) is replaced by an electron transport and injection layer.

[0625] Furthermore, in the structure, "hole injection layer / hole transport layer" can be replaced by "hole injection and transport layer" or "layer that simultaneously injects and transports holes".

[0626] The organic light-emitting devices described herein can be manufactured using materials and methods known in the art, except that one or more layers of organic material are formed using a coating composition comprising a compound of formula 1.

[0627] For example, the organic light-emitting device of this specification can be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. In this case, the organic light-emitting device can be manufactured by depositing a metal, or a conductive metal oxide, or an alloy thereof, on a substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation to form the anode; forming an organic material layer on the anode by a solution method, deposition method, etc., including a hole injection layer, a hole transport layer, a light-emitting layer, and a layer that simultaneously transports and injects electrons; and then depositing a material that can be used as a cathode on the organic material layer. In addition to the above method, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0628] This specification also provides a method for manufacturing an organic light-emitting device formed by using the coating composition described above.

[0629] Specifically, an exemplary embodiment of this specification includes: preparing a substrate; forming a first electrode on the substrate; forming an organic material layer having one or more layers on the first electrode; and forming a second electrode on the organic material layer, wherein forming the organic material layer includes forming an organic material layer having one or more layers by using the coating composition.

[0630] In one exemplary embodiment of this specification, spin coating is used to form an organic material layer having one or more layers by using the coating composition.

[0631] In another exemplary embodiment, a printing method is used to form an organic material layer having one or more layers by using the coating composition.

[0632] In one exemplary embodiment of this specification, examples of printing methods include, but are not limited to, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing.

[0633] Due to the structural characteristics of the coating composition according to an exemplary embodiment of this specification, the solution method is suitable for the coating composition, allowing the organic material layer to be formed by printing, and thus providing economic benefits in terms of time and cost when manufacturing devices.

[0634] In one exemplary embodiment of this specification, forming an organic material layer having one or more layers by using the coating composition includes: coating the coating composition onto a first electrode; and subjecting the coated composition to heat treatment or light treatment.

[0635] In one exemplary embodiment of this specification, heat treatment of the coated composition can be performed by heat treatment. The heat treatment temperature for heat treating the coated composition is from 85°C to 250°C. Specifically, the heat treatment temperature can be from 100°C to 250°C, and more specifically from 150°C to 250°C.

[0636] In one exemplary embodiment of this specification, the heat treatment time for heat-treating the coated composition can be from 1 minute to 2 hours, in one exemplary embodiment it can be from 1 minute to 1 hour, and in another exemplary embodiment it can be from 30 minutes to 1 hour.

[0637] In one exemplary embodiment of this specification, the coating composition can be light-treated by UV irradiation. The light treatment of the coating composition can be performed for 30 minutes to 5 hours.

[0638] In one exemplary embodiment of this specification, coating the first electrode with the coating composition includes coating the first electrode with the coating composition and coating an additional organic material layer disposed on the first electrode with the coating composition.

[0639] In one exemplary embodiment of this specification, the additional organic material layer means an organic material layer formed of an additional material that does not contain the coating composition or its cured product.

[0640] When coating the first electrode with the coating composition, a solvent that will not dissolve the material in the underlying layer is used. For example, when the coating composition is applied to the hole transport layer, the coating composition contains a solvent that will not dissolve the material in the underlying layer (first electrode, hole injection layer, etc.). Therefore, it has the advantage that the hole transport layer can be introduced by a solution method.

[0641] By subjecting the coating composition to heat treatment or light treatment, the plurality of compounds contained in the coating composition can form crosslinks, thereby providing an organic material layer comprising a thin film structure. In this case, when additional layers are stacked on the surface of the organic material layer formed by using the coating composition, it is possible to prevent the organic material layer from dissolving in solvents, being morphologically affected, or decomposing.

[0642] Therefore, when the organic material layer formed by using the coating composition is formed by a method including heat treatment or light treatment of the coated composition, the solvent resistance is improved, allowing multiple layers to be formed by repeated solution deposition and crosslinking, and the stability is improved, thereby improving the lifespan characteristics of the device.

[0643] In one exemplary embodiment of this specification, a material with a high work function is generally preferred as the anode material to facilitate hole injection into the organic material layer. Specific examples of anode materials include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline; and so on, but are not limited thereto.

[0644] In one exemplary embodiment of this specification, a material with a low work function is generally preferred as the cathode material to facilitate electron injection into the organic material layer. Specific examples of cathode materials include: metals, such as barium, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials, such as LiF / Al or LiO2 / Al; and so on, but are not limited thereto.

[0645] In one exemplary embodiment of this specification, the hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes and thus has the effect of injecting holes at the anode and the excellent effect of injecting holes into the light-emitting layer or light-emitting material, preventing excitons generated by the light-emitting layer from moving to the electron injection layer or electron injection material, and also has excellent thin film formation ability. Furthermore, the highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. Specific examples of hole injection materials include compounds of the above-described chemical formula 1, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, and so on. Organic materials, anthraquinones, conductive polymers based on polyaniline and polythiophene, etc., but not limited to these.

[0646] In one exemplary embodiment of this specification, the hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is suitably a material with high hole mobility capable of receiving holes from the anode or hole injection layer and transferring the holes to the light-emitting layer. Specific examples of hole transport materials include arylamine-based organic materials, conductive polymers, block copolymers having both conjugated and non-conjugated portions, etc., but the hole transport material is not limited to these. More specifically, compounds containing arylamine groups can be used in the hole transport layer.

[0647] In one exemplary embodiment of this specification, the hole transport layer comprises a compound with the following chemical formula HT-1.

[0648] [Chemical formula HT-1]

[0649]

[0650] In the chemical formula HT-1,

[0651] L201 is a substituted or unsubstituted aryl group, and

[0652] R201 to R204 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic.

[0653] In one exemplary embodiment of this specification, L201 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0654] In one exemplary embodiment of this specification, L201 is an aryl group.

[0655] In one embodiment of this specification, L201 is a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted naphthylene.

[0656] In one exemplary embodiment of this specification, L201 is phenylene, biphenylene, or naphthylene.

[0657] In one exemplary embodiment of this specification, L201 is a biphenylene oxide.

[0658] In one exemplary embodiment of this specification, R201 to R204 may be the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0659] In one exemplary embodiment of this specification, R201 to R204 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0660] In one exemplary embodiment of this specification, R201 to R204 may be the same as or different from each other, and each is independently aryl.

[0661] In one exemplary embodiment of this specification, R201 to R204 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; or a substituted or unsubstituted naphthyl.

[0662] In one exemplary embodiment of this specification, R201 to R204 may be the same as or different from each other, and each is independently phenyl, biphenyl or naphthyl.

[0663] In one exemplary embodiment of this specification, the chemical formula HT-1 has the following structure.

[0664]

[0665] In one exemplary embodiment of this specification, the luminescent material included in the luminescent layer is a material capable of receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, to emit light in the visible light region, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include: 8-hydroxyquinoline aluminum complexes (Alq3); carbazole-based compounds; dipolystyrene-based compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Zyrazoles, benzothiazole-based and benzimidazole-based compounds; polymers based on poly(p-phenylenevinylene) (PPV); spirocyclic compounds; polyfluorene; red fluorene; etc., but not limited to these.

[0666] In one exemplary embodiment of this specification, the light-emitting layer may comprise a host material and a dopant material. Examples of host materials include fused aromatic ring derivatives, heterocyclic compounds, etc. Specifically, examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited to these examples. More specifically, anthracene derivatives may be used as the host.

[0667] In one exemplary embodiment of this specification, the body of the light-emitting layer comprises a compound with the following chemical formula EH-1.

[0668] [Chemical formula EH-1]

[0669]

[0670] In chemical formula EH-1,

[0671] L301 and L302 may be identical or different from each other, and each is independently a direct bond; a substituted or unsubstituted aryl group; or a substituted or unsubstituted divalent heterocyclic group.

[0672] Ar301 and Ar302 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group.

[0673] R301 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0674] r301 is an integer from 1 to 7, and when r301 is 2 or greater, two or more R301s are the same or different from each other.

[0675] In one exemplary embodiment of this specification, L301 and L302 may be the same as or different from each other, and each is independently a direct bond; a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

[0676] In one exemplary embodiment of this specification, L301 and L302 may be the same as or different from each other, and each is independently a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted naphthylene.

[0677] In one exemplary embodiment of this specification, L301 and L302 are each direct keys.

[0678] In one exemplary embodiment of this specification, Ar301 and Ar302 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group.

[0679] In one exemplary embodiment of this specification, Ar301 and Ar302 may be the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic aryl; or a substituted or unsubstituted polycyclic aryl.

[0680] In one exemplary embodiment of this specification, Ar301 and Ar302 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted anthraceneyl; a substituted or unsubstituted phenanthryl; a substituted or unsubstituted triphenylene; a substituted or unsubstituted pyrene; or a substituted or unsubstituted fluoreneyl.

[0681] In one exemplary embodiment of this specification, Ar301 and Ar302 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl or a substituted or unsubstituted naphthyl group.

[0682] In one exemplary embodiment of this specification, Ar301 and Ar302 are each naphthyl.

[0683] In one exemplary embodiment of this specification, R301 is hydrogen.

[0684] In one exemplary embodiment of this specification, the chemical formula EH-1 is any of the following structures.

[0685]

[0686] In one exemplary embodiment of this specification, aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, metal complexes, etc., may be used as dopants. Specifically, aromatic amine derivatives are fused aromatic ring derivatives having substituted or unsubstituted aryl amino groups, and examples include pyrene, anthracene, etc., having aryl amino groups. Diindrone pyrene, etc., and styrylamine compounds are compounds in which at least one aryl vinyl group is substituted with a substituted or unsubstituted arylamine, and one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups are substituted or unsubstituted. Specific examples include, but are not limited to, styrylamines, styryldiamines, styryltriamines, styryltetraamines, etc. In addition, examples of metal complexes include iridium complexes, platinum complexes, etc., but are not limited to. More specifically, compounds containing arylamine groups can be used as dopants.

[0687] In one exemplary embodiment of this specification, the dopant of the light-emitting layer comprises a compound with the following chemical formula: ED-1 or ED-2.

[0688] [Chemical Formula ED-1]

[0689]

[0690] [Chemical formula ED-2]

[0691]

[0692] In chemical formulas ED-1 and ED-2,

[0693] L401 is a substituted or unsubstituted arylene group; or a substituted or unsubstituted alkenyl group.

[0694] R401 to R404 and R501 to R504 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0695] r401 is an integer from 1 to 10, and

[0696] When r401 is 2 or greater, the structures within the parentheses may be the same or different from each other.

[0697] In one exemplary embodiment of this specification, the chemical formula ED-2 is the following chemical formula ED-2-1.

[0698] [Chemical formula ED-2-1]

[0699]

[0700] In the chemical formula ED-2-1,

[0701] R501 to R504 are the same as those defined in chemical formula ED-2.

[0702] In one exemplary embodiment of this specification, L401 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms.

[0703] In one exemplary embodiment of this specification, L401 is arylene or alkenyl.

[0704] In one exemplary embodiment of this specification, L401 is a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted vinylene.

[0705] In one exemplary embodiment of this specification, L401 is phenylene, biphenylene, naphthylene, or vinylene.

[0706] In one exemplary embodiment of this specification, R401 to R404 and R501 to R504 may be the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0707] In one exemplary embodiment of this specification, R401 to R404 and R501 to R504 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0708] In one exemplary embodiment of this specification, R401 to R404 and R501 to R504 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, or a substituted or unsubstituted naphthyl.

[0709] In one exemplary embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently an unsubstituted or alkyl-substituted phenyl, an unsubstituted or alkyl-substituted biphenyl, or an unsubstituted or alkyl-substituted naphthyl.

[0710] In one exemplary embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently an unsubstituted or alkyl-substituted phenyl.

[0711] In one exemplary embodiment of this specification, R501 to R504 may be the same as or different from each other, and each is independently an unsubstituted or silyl-substituted phenyl.

[0712] In this specification, silyl group is a group represented by -SiRxRyRz, where Rx, Ry, and Rz may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group. The number of carbon atoms in the silyl group is not particularly limited, but is preferably from 1 to 60.

[0713] In one exemplary embodiment of this specification, the chemical formula ED-1 has the following structure.

[0714]

[0715] In one exemplary embodiment of this specification, the chemical formula ED-2 has the following structure.

[0716]

[0717] In one exemplary embodiment of this specification, the electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is suitably a material with high electron mobility that can effectively receive electrons from the cathode and transfer them to the light-emitting layer. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavonoid-metal complexes, etc. The electron transport layer can be used with any desired cathode material as used according to the related art. In particular, suitable examples of cathode materials are typical materials with low work functions followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0718] In one exemplary embodiment of this specification, the electron injection layer is a layer that injects electrons from the electrode. The electron injection material is preferably a compound that possesses the ability to transport electrons, the effect of injecting electrons from the cathode, and an excellent effect of injecting electrons into the light-emitting layer or light-emitting material, preventing excitons generated by the light-emitting layer from migrating to the hole injection layer, and also exhibits excellent ability to form thin films. Specific examples include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, benzimidazoles, perylenetetracarboxylic acid, phenanthroline, fluorenemethane, anthrones, and their derivatives; metal complex compounds; nitrogen-containing 5-membered ring derivatives; and so on, but not limited to these.

[0719] In one exemplary embodiment of this specification, examples of metal complex compounds include, but are not limited to, lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)chlorogallium, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc.

[0720] In one exemplary embodiment of this specification, the electron transport layer and the electron injection layer can be formed as layers that simultaneously transport and inject electrons, and can be represented as an electron transport and injection layer. In this case, the material applied to the electron transport and injection layer can be both the aforementioned electron transport material and electron injection material. For example, a benzimidazole-based compound can be used in the electron transport and injection layer.

[0721] In one exemplary embodiment of this specification, the electron transport and injection layer comprises a compound with the chemical formula ET-1 or ET-2.

[0722] [Chemical formula ET-1]

[0723]

[0724] [Chemical formula ET-2]

[0725]

[0726] In chemical formulas ET-1 and ET-2,

[0727] L601 and L602 may be the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0728] Ar601 and Ar602 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0729] R601 and R701 may be the same as or different from each other, and each is independently a hydrogen, deuterium, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, and

[0730] r701 is an integer from 1 to 8, and when r701 is 2 or greater, two or more R701s are the same or different from each other.

[0731] In one exemplary embodiment of this specification, L601 and L602 may be the same as or different from each other, and each is independently a direct-linked, substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

[0732] In one exemplary embodiment of this specification, L601 and L602 may be the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted naphthylene.

[0733] In one exemplary embodiment of this specification, L601 and L602 are each direct keys.

[0734] In one exemplary embodiment of this specification, Ar601 and Ar602 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group.

[0735] In one exemplary embodiment of this specification, Ar601 and Ar602 may be the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic aryl or a substituted or unsubstituted polycyclic aryl.

[0736] In one exemplary embodiment of this specification, Ar601 and Ar602 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraceneyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyrene, or a substituted or unsubstituted fluorene.

[0737] In one exemplary embodiment of this specification, Ar601 and Ar602 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl or a substituted or unsubstituted naphthyl group.

[0738] In one exemplary embodiment of this specification, Ar601 and Ar602 are each naphthyl.

[0739] In one exemplary embodiment of this specification, R601 and R701 may be the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0740] In one exemplary embodiment of this specification, R601 is a substituted or unsubstituted aryl group.

[0741] In one exemplary embodiment of this specification, R601 is a substituted or unsubstituted phenyl group.

[0742] In one exemplary embodiment of this specification, R601 is phenyl.

[0743] In one exemplary embodiment of this specification, R701 is hydrogen, deuterium, alkyl, or aryl.

[0744] In one exemplary embodiment of this specification, R701 is hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted biphenyl.

[0745] In one exemplary embodiment of this specification, R701 is hydrogen, deuterium, methyl, ethyl, propyl, butyl, phenyl, naphthyl, or biphenyl.

[0746] In one exemplary embodiment of this specification, R701 is hydrogen, methyl, or phenyl.

[0747] In one exemplary embodiment of this specification, the chemical formula ET-1 has the following structure.

[0748]

[0749] In one exemplary embodiment of this specification, the chemical formula ET-2 has the following structure.

[0750]

[0751] In one exemplary embodiment of this specification, the hole blocking layer is a layer that blocks holes from reaching the cathode, and can typically be formed under the same conditions as the hole injection layer. Specific examples of hole blocking materials include... Diazole or triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc., but not limited to these.

[0752] In one exemplary embodiment of this specification, the electron blocking layer is a layer that blocks electrons from reaching the anode, and materials known in the art can be used.

[0753] Depending on the materials used, the organic light-emitting device according to this specification can be a top-emitting, bottom-emitting, or dual-emitting type.

[0754] Invention Embodiments

[0755] In the following description, this specification will be described in detail with reference to embodiments used to specifically describe this specification. However, various modifications may be made to the embodiments described herein, and the scope of this specification should not be construed as limited to the embodiments described below. The embodiments of this specification are provided to provide a more complete explanation of this specification to those skilled in the art.

[0756] <Synthesis example>

[0757] Synthesis Example 1. Synthesis of Compound 1

[0758]

[0759] Compound 1a (1.0 equivalent), compound 1b (2.2 equivalent), and sodium tert-butoxide (NaO) were mixed. t Bu (3.0 equivalent) was placed in a round-bottom flask (RBF), and then toluene (Tol) (0.1 M) was added. After raising the temperature to 90 °C, bis(tri-tert-butylphosphine)palladium (0)(Pd) was added. tBu3P)2)(0.05 equivalents), and the resulting mixture was stirred for 3 hours. Water was added, and the organic layer was extracted with dichloromethane (DCM), dried over magnesium sulfate (MgSO4), and purified by column chromatography with dichloromethane / hexane to obtain compound 1. [M+H] + =1584

[0760] Synthesis Example 2. Synthesis of Compound 2

[0761]

[0762] Compound 2 was synthesized in the same manner as in Synthesis Example 1, except that in Synthesis Example 1, compounds 2a and 2b were used instead of compounds 1a and 1b, respectively.

[0763] [M+H] + =2002

[0764] Synthesis Example 3. Synthesis of Compound 3

[0765]

[0766] Compound 3 was synthesized in the same manner as in Synthesis Example 1, except that in Synthesis Example 1, compounds 2a and 3b were used instead of compounds 1a and 1b, respectively.

[0767] [M+H] + =2038

[0768] Synthesis Example 4. Synthesis of Compound 4

[0769]

[0770] Compound 4 was synthesized in the same manner as in Synthesis Example 1, except that in Synthesis Example 1, compounds 2a and 4b were used instead of compounds 1a and 1b, respectively.

[0771] [M+H] + =1962

[0772] Synthesis Example 5. Synthesis of Compound 5

[0773]

[0774] Compound 5 was synthesized in the same manner as in Synthesis Example 1, except that in Synthesis Example 1, compounds 5a and 5b were used instead of compounds 1a and 1b, respectively.

[0775] [M+H] + =1964

[0776] Synthesis Example 6. Synthesis of Compound 6

[0777]

[0778] Compound 6 was synthesized in the same manner as in Synthesis Example 1, except that in Synthesis Example 1, compounds 2a and 6b were used instead of compounds 1a and 1b, respectively.

[0779] [M+H] + =3330

[0780] Synthesis Example 7. Synthesis of Compound 7

[0781]

[0782] Compound 7 was synthesized in the same manner as in Synthesis Example 1, except that in Synthesis Example 1, compounds 2a and 7b were used instead of compounds 1a and 1b, respectively.

[0783] [M+H] + =1798

[0784] Synthesis Example 8. Synthesis of Compound 8

[0785] (1) Synthesis of intermediate 8-1

[0786]

[0787] 1-Bromo-4-fluorobenzene (27.9 mL, 255 mmol, 1.7 equivalents) was added to tetrahydrofuran (THF) (500 mL). After purging with nitrogen, the mixture was cooled to -78 °C. n-Butyllithium (n-BuLi) (2.5 M in hexane) (96 mL, 240 mmol, 1.6 equivalents) was added to the reaction mixture in a dropping funnel, and the resulting mixture was stirred at -78 °C for 30 minutes. 2-Bromofluorenone (38.9 g, 150 mmol) was added. The mixture was stirred overnight while slowly heating to room temperature (RT). After terminating the reaction by adding distilled water, extraction was performed with ethyl acetate and water. The organic layer was collected, dried with magnesium sulfate (MgSO4), and filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent, yielding intermediate 8-1.

[0788] (2) Synthesis of intermediate 8-2

[0789]

[0790] Intermediate 8-1 (53 g, 150 mmol) and phenol (70.6 g, 750 mmol, 5 equivalents) were placed in a round-bottom flask (RBF). After adding methanesulfonic acid (CH3SO3H) (214 mL, 0.7 M), the mixture was stirred at 60 °C for 4 hours. After adding ice water, extraction was performed with ethyl acetate and water. The organic layer was collected, dried over MgSO4, and filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. Following column purification, crystallization was carried out under dichloromethane / heptane conditions to obtain 40.6 g of intermediate 8-2.

[0791] (3) Synthesis of intermediate 8-3

[0792]

[0793] Intermediate 8-2 (40 g, 92.7 mmol), 4-nitrobenzaldehyde (21.2 g, 139 mmol, 1.5 equivalents), copper(II) acetate (Cu(OAc)2) (842 mg, 4.64 mmol, 5 mol%), and cesium carbonate (CS2CO3) (45.3 g, 139 mmol, 1.5 equivalents) were placed in an RBF container. Dimethylformamide (DMF) (310 mL) was added, and the resulting mixture was stirred at 100 °C for 4 hours. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / heptane conditions to obtain 38.7 g of intermediate 8-3.

[0794] (4) Synthesis of intermediate 8-4

[0795]

[0796] methyltriphenylbromide (CH3PPh3Br) (51.6 g, 144.6 mmol, 2 equivalents), potassium tert-butoxide (KOtBu) (16.2 g, 144.6 mmol, 2 equivalents), and THF (217 mL) were added to the RBF, and the resulting mixture was cooled to 0 °C. A solution of intermediate 8-3 (38.7 g, 72.3 mmol) in tetrahydrofuran (THF) (144 mL) was added to the reaction mixture. The resulting mixture was stirred for 1 hour while being heated to room temperature. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried over a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under dichloromethane / ethanol (DCM / EtOH) conditions to obtain 33.7 g of intermediate 8-4.

[0797] (5) Synthesis of intermediate 8-5

[0798]

[0799] Intermediate 8-4 (10.7 g, 20 mmol), compound I1 (14.9 g, 40 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (511 mg, 1 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (3.84 g, 40 mmol, 2 equivalents) were placed in an RBF. After purging with nitrogen, toluene (100 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 8.3 g of intermediate 8-5.

[0800] (6) Synthesis of compound 8

[0801]

[0802] Compound I2 (1.19 g, 2.5 mmol), intermediate 8-5 (4.54 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried over a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 2.9 g of compound 8. The synthesis of compound 8 was confirmed by LC-MS and NMR. MS: [M+H] + =1964

[0803] NMR measurements of compound 8:

[0804] 1 H NMR (500MHz, DMSO-d6) δ7.90 (d, 2H), 7.80 (d, 4H), 7.46-7.30 (m, 20H), 7.30-7.22 (m , 4H), 7.13-7.01(m, 34H), 6.97-6.83(m, 22H), 6.61(m, 2H), 5.65(d, 2H), 5.11(d, 2H)

[0805] Synthesis Example 9. Synthesis of Compound 9

[0806]

[0807] Compound I3 (1.23 g, 2.5 mmol), intermediate 8-5 (4.54 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 3.21 g of compound 9. The synthesis of compound 9 was confirmed by LC-MS and NMR. MS: [M+H] + =1981

[0808] NMR measurements of compound 9:

[0809] 1 H NMR (500MHz, DMSO-d6) δ7.80 (d, 4H), 7.46-7.30 (m, 20H), 7.30-7.17 (m, 6H), 7 .13-7.01(m, 34H), 6.97-6.83(m, 22H), 6.61(m, 2H), 5.65(d, 2H), 5.11(d, 2H)

[0810] Synthesis Example 10. Synthesis of Compound 10

[0811]

[0812] Compound I4 (1.32 g, 2.5 mmol), intermediate 8-5 (4.54 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 3.3 g of compound 10. The synthesis of compound 10 was confirmed by LC-MS and NMR. MS: [M+H] + =2015

[0813] NMR measurements of compound 10:

[0814] 1 H NMR (500MHz, DMSO-d6) δ8.90 (d, 1H), 8.25 (d, 1H), 8.09 (d, 1H), 7.90-7.80 (m, 5H), 7.46-7.30 (m, 20H ), 7.30-7.22(m, 4H), 7.13-7.01(m, 34H), 6.97-6.83(m, 22H), 6.61(m, 2H), 5.65(d, 2H), 5.11(d, 2H)

[0815] Synthesis Example 11. Synthesis of Compound 11

[0816]

[0817] Compound I5 (1.19 g, 2.5 mmol), intermediate 8-5 (4.54 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 3.0 g of compound 11. The synthesis of compound 11 was confirmed by LC-MS and NMR. MS: [M+H] + =1964

[0818] NMR measurements of compound 11:

[0819] 1 H NMR (500MHz, DMSO-d6) δ7.90 (d, 2H), 7.80 (d, 4H), 7.46-7.30 (m, 20H), 7.30-7.22 (m , 4H), 7.19-7.01(m, 34H), 6.97-6.83(m, 22H), 6.61(m, 2H), 5.65(d, 2H), 5.11(d, 2H)

[0820] Synthesis Example 12. Synthesis of Compound 12

[0821] (1) Synthesis of intermediate 12-1

[0822]

[0823] Intermediate 8-4 (10.7 g, 20 mmol), compound I6 (21.4 g, 40 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (511 mg, 1 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (3.84 g, 40 mmol, 2 equivalents) were placed in an RBF. After purging with nitrogen, toluene (100 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 10.4 g of intermediate 12-1.

[0824] (2) Synthesis of compound 12

[0825]

[0826] Compound I2 (1.19 g, 2.5 mmol), intermediate 12-1 (5.43 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 3.7 g of compound 12. The synthesis of compound 12 was confirmed by LC-MS and NMR. MS: [M+H] + =2288

[0827] NMR measurements of compound 12:

[0828] 1 H NMR (500MHz, DMSO-d6) δ7.90-7.80(m, 14H), 7.60-7.52(m, 8H), 7.48-7.22(m, 30H), 7.18-6.95(m, 42H), 6.86(d, 4H), 6.63(m, 2H), 5.65(d, 2H), 5.11(d, 2H)

[0829] Synthesis Example 13. Synthesis of Compound 13

[0830] (1) Synthesis of intermediate 13-1

[0831]

[0832] Intermediate 8-4 (10.7 g, 20 mmol), compound I7 (27.2 g, 40 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (511 mg, 1 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (3.84 g, 40 mmol, 2 equivalents) were placed in an RBF. After purging with nitrogen, toluene (100 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 11 g of intermediate 13-1.

[0833] (2) Synthesis of compound 13

[0834]

[0835] Compound I2 (1.19 g, 2.5 mmol), intermediate 13-1 (6.22 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 4.0 g of compound 13. The synthesis of compound 13 was confirmed by LC-MS and NMR. MS: [M+H] + =2578

[0836] NMR measurements of compound 13:

[0837] 1 H NMR (500MHz, DMSO-d6) δ7.93 (s, 4H), 7.90-7.80 (m, 18H), 7.72 (d, 4H), 7.60-7.52 (m, 8H), 7.4 8-7.22(m, 42H), 7.18-6.95(m, 26H), 6.86-6.80(m, 8H), 6.63(m, 2H), 5.65(d, 2H), 5.11(d, 2H)

[0838] Synthesis Example 14. Synthesis of Compound 14

[0839] (1) Synthesis of intermediate 14-1

[0840]

[0841] Intermediate 14-1 was prepared in the same manner as in (1) of Synthesis Example 8, except that 1-bromo-2,6-difluorobenzene (29.4 mL, 255 mmol, 1.7 equivalents) was used instead of 1-bromo-4-fluorobenzene in (1) of Synthesis Example 8.

[0842] (2) Synthesis of intermediate 14-2

[0843]

[0844] 45.2 g of intermediate 14-2 was obtained by preparing it in the same manner as in (2) of synthesis example 8, except that intermediate 14-1 (56 g, 150 mmol) was used instead of intermediate 8-1 in (2) of synthesis example 8.

[0845] (3) Synthesis of intermediate 14-3

[0846]

[0847] 39.8 g of intermediate 14-3 was obtained by preparing it in the same manner as in (3) of synthesis example 8, except that intermediate 14-2 (45.2 g, 100 mmol) was used instead of intermediate 8-2 in (3) of synthesis example 8.

[0848] (4) Synthesis of intermediate 14-4

[0849]

[0850] 34.8 g of intermediate 14-4 was obtained by preparing it in the same manner as in (4) of synthesis example 8, except that intermediate 14-3 (39.8 g, 72 mmol) was used instead of intermediate 8-3 in (4) of synthesis example 8.

[0851] (5) Synthesis of intermediate 14-5

[0852]

[0853] Intermediate 14-4 (11.0 g, 20 mmol), compound I1 (14.9 g, 40 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (511 mg, 1 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (3.84 g, 40 mmol, 2 equivalents) were placed in an RBF. After purging with nitrogen, toluene (100 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 8.6 g of compound 14-5.

[0854] (6) Synthesis of compound 14

[0855]

[0856] Compound I2 (1.19 g, 2.5 mmol), intermediate 14-5 (4.64 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 3.6 g of compound 14. The synthesis of compound 14 was confirmed by LC-MS and NMR. MS: [M+H] + =2001

[0857] NMR measurements of compound 14:

[0858] 1 H NMR (500MHz, DMSO-d6) δ7.90 (d, 2H), 7.80 (d, 4H), 7.67 (t, 2H), 7.46-7.31 (m, 24H), 7.30-7 .22(m, 4H), 7.13-7.01(m, 26H), 6.97-6.83(m, 22H), 6.61(m, 2H), 5.65(d, 2H), 5.11(d, 2H)

[0859] Synthesis Example 15. Synthesis of Compound 15

[0860] (1) Synthesis of intermediate 15-1

[0861]

[0862] Intermediate 8-2 (8.63 g, 20 mmol) and CS2CO3 (8.47 g, 26 mmol, 1.3 equivalents) were placed in an RBF container. DMF (100 mL) and 3-ethyl-3-iodomethyloxetane (4 mL, 26 mmol) were added, and the resulting mixture was stirred at 60 °C for 4 hours. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. Following column purification, crystallization was carried out under DCM / heptane conditions to obtain 12.3 g of intermediate 15-1.

[0863] (2) Synthesis of intermediate 15-2

[0864]

[0865] Intermediate 15-1 (10.6 g, 20 mmol), compound I1 (14.9 g, 40 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (511 mg, 1 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (3.84 g, 40 mmol, 2 equivalents) were placed in an RBF. After purging with nitrogen, toluene (100 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 11.2 g of intermediate 15-2.

[0866] (3) Synthesis of compound 15

[0867]

[0868] Compound I2 (1.19 g, 2.5 mmol), intermediate 15-2 (4.52 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 3.6 g of compound 15. The synthesis of compound 15 was confirmed by LC-MS and NMR. MS: [M+H] + =1957

[0869] NMR measurements of compound 15:

[0870] 1 H NMR (500MHz, DMSO-d6) δ7.90 (d, 2H), 7.80 (d, 4H), 7.46-7.31 (m, 20H), 7.29-7.22 (m, 4H), 7.13-7 .01(m, 34H), 6.97-6.83(m, 22H), 4.37(d, 4H), 4.28(d, 4H), 4.00(s, 4H), 1.71(q, 4H), 0.82(t, 6H)

[0871] Synthesis Example 16. Synthesis of Compound 16

[0872] (1) Synthesis of intermediate 16-1

[0873]

[0874] Intermediate 8-2 (39 g, 90 mmol), benzocyclobutane-4-boronic acid (20 g, 135 mmol), Cu(OAc)2 (16.4 g, 90 mmol, 1 equivalent) and Molecular sieve (90 g) was placed in an RBF. DCM (900 mL) and triethylamine (TEA) (63 mL, 450 mmol, 5 equivalents) were added, and the resulting mixture was stirred overnight at room temperature. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. Following column purification, crystallization was carried out under DCM / EtOH conditions to obtain 15 g of intermediate 16-1.

[0875] (2) Synthesis of intermediate 16-2

[0876]

[0877] Intermediate 16-1 (10.7 g, 20 mmol), compound I1 (14.9 g, 40 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (511 mg, 1 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (3.84 g, 40 mmol, 2 equivalents) were placed in an RBF. After purging with nitrogen, toluene (100 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 8.7 g of intermediate 16-2.

[0878] (3) Synthesis of compound 16

[0879]

[0880] Compound I2 (1.19 g, 2.5 mmol), intermediate 16-2 (4.54 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried over a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 2.9 g of compound 16. The synthesis of compound 16 was confirmed by LC-MS and NMR. MS: [M+H] + =1964

[0881] NMR measurements of compound 16:

[0882] 1 H NMR (500MHz, DMSO-d6) δ7.90 (d, 2H), 7.80 (d, 4H), 7.46-7.31 (m, 18H), 7.30-7.22 (m, 4H), 7.13-7.01 (m, 32H), 6.97-6.83 (m, 24H), 3.00 (m, 8H)

[0883] Synthesis Example 17. Synthesis of Compound 17

[0884] (1) Synthesis of intermediate 17-1

[0885]

[0886] Intermediate 8-5 (8.25 g, 10 mmol), compound I2 (9.52 g, 20 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (256 mg, 0.5 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (3.84 g, 40 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (50 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 7.2 g of intermediate 17-1.

[0887] (2) Synthesis of compound 17

[0888]

[0889] Compound I1 (931 mg, 2.5 mmol), intermediate 17-1 (6.71 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 5 g of compound 17. The synthesis of compound 17 was confirmed by LC-MS and NMR. MS: [M+H] + =2650

[0890] NMR measurements of compound 17:

[0891] 1 H NMR (500MHz, DMSO-d6) δ7.90 (d, 4H), 7.80 (d, 4H), 7.46-7.18 (m, 52H), 7.13-6.98 (m, 50H), 6.75 (d, 8H), 6.61 (m, 2H), 5.65 (d, 2H), 5.11 (d, 2H)

[0892] Synthesis Example 18. Synthesis of Compound 18

[0893]

[0894] Compound I8 (815 mg, 2.5 mmol), intermediate 8-5 (4.54 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 2.7 g of compound 18. The synthesis of compound 18 was confirmed by LC-MS and NMR. MS: [M+H] + =1814

[0895] NMR measurements of compound 18:

[0896] 1 H NMR (500MHz, DMSO-d6) δ7.93 (d, 2H), 7.80-7.72 (m, 4H), 7.69 (d, 2H), 7.60-7.48 (m, 14H), 7 .44-7.25(m,18H),7.10-6.96(m,34H),6.82(m,2H),6.64(m,2H),5.66(d,2H),5.14(d,2H)

[0897] Synthesis Example 19. Synthesis of Compound 19

[0898]

[0899] Compound I9 (815 mg, 2.5 mmol), intermediate 8-5 (4.54 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 2.8 g of compound 19. The synthesis of compound 19 was confirmed by LC-MS and NMR. MS: [M+H] + =1814

[0900] NMR measurements of compound 19:

[0901] 1 H NMR (500MHz, DMSO-d6) δ8.10 (d, 2H), 7.80-7.72 (m, 4H), 7.60-7.43 (m, 16H), 7 .43-7.25(m,18H),7.10-6.87(m,36H),6.64(m,2H),5.66(d,2H),5.14(d,2H)

[0902] Synthesis Example 20. Synthesis of Compound 20

[0903]

[0904] Compound I8 (815 mg, 2.5 mmol), intermediate 12-1 (5.43 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 3.4 g of compound 20. The synthesis of compound 20 was confirmed by LC-MS and NMR. MS: [M+H] + =2138

[0905] NMR measurements of compound 20:

[0906] 1 H NMR (500MHz, DMSO-d6) δ7.94 (d, 2H), 7.80-7.70 (m, 14H), 7.52-7.43 (m, 8H ), 7.38-6.96(m, 62H), 6.82(m, 2H), 6.63(m, 2H), 5.66(d, 2H), 5.14(d, 2H)

[0907] Synthesis Example 21. Synthesis of Compound 21

[0908] (1) Synthesis of intermediate 21-1

[0909]

[0910] Intermediate 8-4 (10.7 g, 20 mmol), compound I10 (27.2 g, 40 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (511 mg, 1 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (3.84 g, 40 mmol, 2 equivalents) were placed in an RBF. After purging with nitrogen, toluene (100 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried with MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 11 g of intermediate 21-1.

[0911] (2) Synthesis of compound 21

[0912]

[0913] Compound I8 (815 mg, 2.5 mmol), intermediate 21-1 (6.22 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 3.7 g of compound 21. The synthesis of compound 21 was confirmed by LC-MS and NMR. MS: [M+H] + =2426

[0914] NMR measurements of compound 21:

[0915] 1 H NMR (500MHz, DMSO-d6) δ7.93-7.85(m, 6H), 7.80-7.70(m, 14H), 7.54-7.43(m, 16H ), 7.38-7.06(m, 52H), 6.94-6.82(m, 12H), 6.62(m, 2H), 5.66(d, 2H), 5.14(d, 2H)

[0916] Synthesis Example 22. Synthesis of Compound 22

[0917] (1) Synthesis of intermediate 22-1

[0918]

[0919] Intermediate 14-4 (11.0 g, 20 mmol), compound I11 (13.5 g, 40 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (511 mg, 1 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (3.84 g, 40 mmol, 2 equivalents) were placed in an RBF. After purging with nitrogen, toluene (100 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 9.2 g of intermediate 22-1.

[0920] (2) Synthesis of compound 22

[0921]

[0922] Compound I12 (940 mg, 2.5 mmol), intermediate 22-1 (4.44 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 2.6 g of compound 22. The synthesis of compound 22 was confirmed by LC-MS and NMR. MS: [M+H] + =1828

[0923] NMR measurements of compound 22:

[0924] 1 H NMR (500MHz, DMSO-d6) δ8.85 (d, 1H), 8.02 (d, 1H), 7.95 (m, 2H), 7.80-7.70 (m, 5H), 7.58 -7.43(m,18H),7.32-6.98(m,52H),6.83(s,1H),6.62(m,2H),5.66(d,2H),5.15(d,2H)

[0925] Synthesis Example 23. Synthesis of Compound 23

[0926]

[0927] Compound I8 (815 mg, 2.5 mmol), intermediate 14-5 (4.64 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 3.0 g of compound 23. The synthesis of compound 23 was confirmed by LC-MS and NMR. MS: [M+H] + =1850

[0928] NMR measurements of compound 23:

[0929] 1 H NMR (500MHz, DMSO-d6) δ7.93 (d, 2H), 7.80-7.72 (m, 4H), 7.69 (d, 2H), 7.58-7.48 (m, 16H), 7 .30-7.19(m,22H),7.10-6.96(m,26H),6.82(m,2H),6.64(m,2H),5.66(d,2H),5.14(d,2H)

[0930] Synthesis Example 24. Synthesis of Compound 24

[0931] (1) Synthesis of intermediate 24-1

[0932]

[0933] Intermediate 15-1 (10.6 g, 20 mmol), compound I11 (13.5 g, 40 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (511 mg, 1 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (3.84 g, 40 mmol, 2 equivalents) were placed in an RBF. After purging with nitrogen, toluene (100 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 10.7 g of intermediate 24-1.

[0934] (2) Synthesis of compound 24

[0935]

[0936] Compound I8 (815 mg, 2.5 mmol), intermediate 24-1 (4.32 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried over a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 2.8 g of compound 24. The synthesis of compound 24 was confirmed by LC-MS and NMR. MS: [M+H] + =1734

[0937] NMR measurements of compound 24:

[0938] 1 H NMR (500MHz, DMSO-d6) δ7.93 (d, 2H), 7.80-7.72 (m, 4H), 7.69 (d, 2H), 7.49-7.40 (m, 10H), 7.31-6 .90(m, 48H), 6.83-6.74(m, 6H), 4.37(d, 4H), 4.28(d, 4H), 4.00(s, 4H), 1.71(q, 4H), 0.82(t, 6H)

[0939] Synthesis Example 25. Synthesis of Compound 25

[0940]

[0941] Compound I8 (815 mg, 2.5 mmol), intermediate 16-2 (4.54 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 2.6 g of compound 25. The synthesis of compound 25 was confirmed by LC-MS and NMR. MS: [M+H] + =1814

[0942] NMR measurements of compound 25:

[0943] 1 H NMR (500MHz, DMSO-d6) δ7.93 (d, 2H), 7.80-7.72 (m, 4H), 7.69 (d, 2H), 7.49-7.40 (m, 10H), 7.32-6.87 (m, 52H), 6.86-6.79 (m, 4H), 3.00 (m, 8H)

[0944] Synthesis Example 26. Synthesis of Compound 26

[0945] (1) Synthesis of intermediate 26-1

[0946]

[0947] Intermediate 8-5 (8.25 g, 10 mmol), compound I9 (6.52 g, 20 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (256 mg, 0.5 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (1.92 g, 20 mmol, 2 equivalents) were placed in an RBF. After purging with nitrogen, toluene (50 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was carried out under DCM / EtOH conditions to obtain 6 g of intermediate 26-1.

[0948] (2) Synthesis of compound 26

[0949]

[0950] Compound I1 (931 mg, 2.5 mmol), intermediate 26-1 (5.9 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(O)(Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 equivalents) were placed in an RBF. After purging with nitrogen, toluene (12.5 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 3.7 g of compound 26. The synthesis of compound 26 was confirmed by LC-MS and NMR. MS: [M+H] + =2350

[0951] NMR measurements of compound 26:

[0952] 1 H NMR (500MHz, DMSO-d6) δ8.11 (d, 4H), 7.80-7.72 (m, 4H), 7.55-7.43 (m, 22H), 7 .35-7.21(m,22H),7.11-6.88(m,46H),6.64(m,2H),5.66(d,2H),5.14(d,2H)

[0953] <Example>

[0954] Example 1

[0955] A thin coating with a thickness of An indium tin oxide (ITO) glass substrate was immersed in distilled water containing a cleaning agent and ultrasonically washed. In this case, a product manufactured by Fischer Co. was used as the cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice for 10 minutes each time with distilled water. After washing with distilled water, the substrate was ultrasonically washed with isopropanol and acetone solvents, dried, then cleaned for 5 minutes, and transferred to a glove box.

[0956] On the ITO transparent electrode prepared above, 1.5 wt% cyclohexanone ink comprising Compound 1 and Compound P prepared in Synthesis Example 1 (8:2 weight ratio, compound 1: compound P) was spin-coated onto the ITO surface and heat-treated (cured) at 230°C for 30 minutes to form a hole injection layer with a thickness of 30 nm. 2 wt% toluene ink of the following α-NPD compound was spin-coated onto the hole injection layer to form a hole transport layer with a thickness of 40 nm. Subsequently, the ITO transparent electrode was transferred to a vacuum deposition machine, and the following ADN compound and the following DPAVBi compound were vacuum-deposited onto the hole transport layer at a weight ratio of 20:1 (AND:DPAVBi) to a thickness of 20 nm to form a light-emitting layer. The following BCP compound was vacuum-deposited onto the light-emitting layer to a thickness of 35 nm to form an electron transport and injection layer. Lithium fluoride (LiF) and aluminum are sequentially deposited on layers that simultaneously transport and inject electrons to thicknesses of 1 nm and 100 nm, respectively, to form a cathode.

[0957]

[0958] In the above process, the deposition rate of organic materials is maintained at to The deposition rates of lithium fluoride and aluminum at the cathode were maintained at... and And maintain the vacuum level at 2×10 during deposition. -7 Up to 5×10 -6 Entrust.

[0959] Example 2

[0960] The organic light-emitting device was manufactured in the same manner as in Example 1, except that compound 2 was used instead of compound 1.

[0961] Example 3

[0962] The organic light-emitting device was manufactured in the same manner as in Example 1, except that compound 3 was used instead of compound 1.

[0963] Example 4

[0964] The organic light-emitting device was manufactured in the same manner as in Example 1, except that compound 4 was used instead of compound 1.

[0965] Example 5

[0966] The organic light-emitting device was manufactured in the same manner as in Example 1, except that compound 5 was used instead of compound 1.

[0967] Example 6

[0968] The organic light-emitting device was manufactured in the same manner as in Example 1, except that compound 6 was used instead of compound 1.

[0969] Example 7

[0970] The organic light-emitting device was manufactured in the same manner as in Example 1, except that compound 7 was used instead of compound 1.

[0971] Comparative Example 1

[0972] The organic light-emitting device was manufactured in the same manner as in Example 1, except that compound A-1 was used instead of compound 1.

[0973] Comparative Example 2

[0974] The organic light-emitting device was manufactured in the same manner as in Example 1, except that compound A-2 was used instead of compound 1.

[0975] Comparative Example 3

[0976] The organic light-emitting device was manufactured in the same manner as in Example 1, except that compound A-3 was used instead of compound 1.

[0977]

[0978] For the organic light-emitting devices manufactured in Examples 1 to 7 and Comparative Examples 1 to 3, at 10 mA / cm 2 The driving voltage, current efficiency, quantum efficiency (QE), and luminance value were measured under the given current, and the time (T95) required for the luminance to return to 95% of the initial luminance (1000 nits) was measured. The results are shown in Table 1 below.

[0979] [Table 1]

[0980]

[0981] Table 1 shows that, compared with organic light-emitting devices using compounds containing only two amine groups (Comparative Examples 1 and 2) and organic light-emitting devices using compounds containing a core structure (La) different from that of the present invention and not containing curable groups (Comparative Example 3), organic light-emitting devices containing compounds according to the present invention (Examples 1 to 7) have lower driving voltage, higher efficiency and brightness, and longer lifespan.

[0982] Example 8

[0983] A thin coating with a thickness of An indium tin oxide (ITO) glass substrate was immersed in distilled water containing a cleaning agent and ultrasonically washed. In this case, a product manufactured by Fischer Co. was used as the cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice for 10 minutes each time with distilled water. After washing with distilled water, the substrate was ultrasonically washed with isopropanol and acetone solvents, dried, then cleaned for 5 minutes, and transferred to a glove box.

[0984] Two wt% cyclohexanone inks, comprising compound 8 and compound G prepared in Synthesis Example 8 at a weight ratio of 8:2, were spin-coated onto an ITO surface and heat-treated at 220°C for 30 minutes to form a thickness of [missing information]. Hole injection layer.

[0985] 2% by weight of toluene ink from compound A was spin-coated onto the hole injection layer, and the coated material was heat-treated at 120°C for 10 minutes to form a layer with a thickness of [missing information]. A hole transport layer. Compounds B and C were vacuum-deposited onto the hole transport layer at a weight ratio of 92:8, thereby forming a layer with a thickness of [missing information]. The luminescent layer is formed by vacuum deposition of compound D onto the luminescent layer, thereby creating a layer with a thickness of [missing information]. The electron transport and injection layer. LiF and aluminum are sequentially deposited on the electron transport and injection layer to respectively have electron transport and injection layers. and The thickness of the cathode is thus formed.

[0986]

[0987] In the above process, the deposition rate of organic materials is maintained at to The deposition rates of lithium fluoride and aluminum at the cathode were maintained at... and And maintain the vacuum level at 2×10 during deposition. -7 Up to 5×10 -8 Entrust.

[0988] Examples 9 to 26

[0989] The organic light-emitting device was fabricated in the same manner as in Example 8, except that the compound described in Table 2 below was used instead of compound 8 during the fabrication of the hole injection layer (HIL).

[0990] Comparative Examples 4 to 8

[0991] The organic light-emitting device was fabricated in the same manner as in Example 8, except that the compounds described in Table 2 below were used instead of compound 8 during the fabrication of the hole injection layer.

[0992] The compounds CE1 to CE5 used in Comparative Examples 4 to 8 are as follows.

[0993]

[0994] Table 2 below shows the results at 10 mA / cm 2 The results of measuring the driving voltage, external quantum efficiency, brightness and lifetime of each organic light-emitting device manufactured in Examples 8 to 26 and Comparative Examples 4 to 8 at a current density.

[0995] External quantum efficiency is obtained by dividing the number of emitted photons by the number of injected charge carriers. T95 refers to the time (in hours) required for the brightness to decrease to 95% of its initial brightness (500 nits).

[0996] [Table 2]

[0997]

[0998] The compounds of Formula 1 according to the present invention were used as the main body of the hole injection layer in Examples 8 to 26, and in Comparative Examples 4 to 8, compounds CE1 and CE2 containing only two amine groups, compounds CE3 and CE5 without curable groups, or compound CE4 with a core structure (La) of biphenylene were used.

[0999] As shown in Table 2, it can be determined that, compared with the organic light-emitting devices of Comparative Examples 4 to 8, the driving voltage is reduced and the lifetime is improved in the organic light-emitting devices (Examples 8 to 26) in which a compound of Chemical Formula 1 according to the present invention is used as the host of the hole injection layer. Furthermore, it can be determined that the efficiency and brightness of the organic light-emitting devices of Examples 8 to 26 are improved compared with the organic light-emitting devices of Comparative Examples 4 to 8. It can be thus determined that by including four or more N atoms in the molecule to improve hole mobility, the movement of holes in the molecule is promoted, thereby improving the performance of the organic light-emitting device. Furthermore, since Comparative Examples 6 and 8 (in which compounds without curable groups are used) do not exhibit solvent resistance even after heat treatment, it can be seen that the devices cannot function properly because most of the material is washed away during the film formation of the hole transport layer (HTL). In addition, Comparative Example 7 (in which a compound having a biphenylene oxide as the core structure is used) exhibits characteristics of reduced compound solubility, which affects film properties and thus exhibits low device performance.

[1000] While the preferred exemplary embodiments of the present invention (hole injection layer) have been described above, the present invention is not limited thereto, and various modifications can be made and implemented within the scope of the claims and detailed description of the present invention, and such modifications also fall within the scope of the present invention.

Claims

1. A compound with the following chemical formula 1-1: [Chemical Formula 1-1] wherein In chemical formula 1-1, L1 to L6 may be the same as or different from each other, and each is independently an alkyl-substituted or unsubstituted aryl group; or a divalent spirodifluorene group. L11 and L14 may be the same as or different from each other, and each is independently a direct bond; -O-; alkylene; or arylene. R11 and R12 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; or an alkyl group. Ar1 to Ar4 may be identical or different from each other, and each is independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group. X1 and X4 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group. R1 to R4 may be the same as or different from each other, and each is independently hydrogen; or deuterium. l1, l3, l4, and l6 are each integers from 0 to 3, and when l1, l3, l4, and l6 are each 2 or greater, the structures within the parentheses are either the same or different from each other. l11 and l14 are each integers from 1 to 3, and when l11 and l14 are each 2 or greater, the structures within the parentheses are either the same or different from each other. r1 and r4 are each integers from 1 to 4, r2 and r3 are each integers from 1 to 3, and when r1 to r4 are each 2 or greater, the substituents in parentheses are either the same or different from each other. r11 and r12 are each integers from 1 to 5, and when r11 and r12 are each 2 or greater, the substituents in parentheses are either the same or different from each other. m is an integer from 1 to 10, and when m is 2 or greater, the structures within the parentheses are either the same or different from each other. La can be any of the following structures: In the structure, Cy1 and Cy2 may be the same as or different from each other, and each is independently a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring; Y1 and Y2 may be the same as or different from each other, and each is independently O; S; CRaRb; or SiRcRd. Ra to Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; alkyl; or aryl. R21 to R28 may be the same as or different from each other, and each is independently hydrogen; deuterium; or alkyl. y2 is 0 or 1. r21 to r24 are each integers from 1 to 4, r25 and r26 are each integers from 1 to 3, r27 and r28 are each integers from 1 to 7, and when r21 to r28 are 2 or greater, the substituents in parentheses are either the same or different from each other. as a moiety to be bonded to Chemical Formula 1-1, The photocurable group or the thermosetting group is any one of the following structures: In the structure, L50, L54, L56, and L57 may be the same as or different from each other, and each is an independent direct key; -O-; Or alkylene l50, l54, l56, and l57 are each integers from 1 to 5, and when l50, l54, l56, and l57 are each 2 or greater, the structures within the parentheses are either the same or different from each other. as a moiety to be bonded to Chemical Formula 1-1, The term "substituted or unsubstituted" means substituted with one or more of the following substituents selected from: deuterium; halogen groups; alkyl groups; and heterocyclic groups, substituted with substituents connected to two or more of the said substituents, or without substituents.

2. The compound according to claim 1, wherein La is any of the following structures: In the structure, Ra and Rb may be the same as or different from each other, and each is independently hydrogen; deuterium; alkyl; or aryl. R23 to R30 may be the same as or different from each other, and each is independently hydrogen; deuterium; or alkyl. r25, r26, r29, and r30 are each integers from 1 to 3; r23 and r24 are each integers from 1 to 4; r27 and r28 are each integers from 1 to 7; and when r23 to r30 are 2 or greater, the substituents in parentheses are either the same or different from each other. is a moiety bonded to Chemical Formula 1-1.

3. The compound according to claim 1, wherein La has the following structure: In the structure, Y2 can be O; S; CRaRb; or SiRcRd. Ra to Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; alkyl; or aryl. R21 and R22 may be the same as or different from each other, and each is independently hydrogen; deuterium; or alkyl. y2 is 0 or 1. r21 and r22 are each integers from 1 to 4, and when r21 and r22 are each 2 or greater, the substituents in parentheses are either the same or different from each other. is a moiety bonded to Chemical Formula 1-1.

4. The compound according to claim 1, wherein La has the following structure: In the structure, Cy1 and Cy2 may be the same as or different from each other, and each is independently a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring; Y3 can be O; S; or SiRcRd. Rc and Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; alkyl; or aryl, and as a moiety to be bonded to Chemical Formula 1-1, The term "substituted or unsubstituted" means substituted with one or more of the following substituents selected from: deuterium; halogen groups; alkyl groups; and heterocyclic groups, substituted with substituents connected to two or more of the said substituents, or without substituents.

5. The compound according to claim 1, wherein La is any of the following structures, and the following structures are unsubstituted or substituted with other substituents: In the structure, Ra to Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; alkyl; or aryl, and is a moiety linked to Chemical Formula 1-1.

6. The compound according to claim 1, wherein Ar1 to Ar4 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms. The term "substituted or unsubstituted" means substituted with one or more of the following substituents selected from: deuterium; halogen groups; alkyl groups; and heterocyclic groups, substituted with substituents connected to two or more of the said substituents, or without substituents.

7. The compound according to claim 1, wherein chemical formula 1-1 is any of the following structures: 。 8. The compound according to claim 1, wherein chemical formula 1-1 is any of the following structures: 。 9. The compound according to claim 1, wherein chemical formula 1-1 is any of the following structures: 。 10. A coating composition comprising the compound according to any one of claims 1 to 9.

11. An organic light-emitting device, comprising: First electrode; Second electrode; as well as An organic material layer comprising one or more layers, including a light-emitting layer, disposed between the first electrode and the second electrode. One or more of the organic material layers comprise the coating composition according to claim 10 or its cured product.

12. The organic light-emitting device according to claim 11, wherein the organic material layer comprising the coating composition or its cured product is a hole transport layer or a hole injection layer.

13. A method for manufacturing an organic light-emitting device, the method comprising: Prepare the base; A first electrode is formed on the substrate; An organic material layer having one or more layers is formed on the first electrode; as well as A second electrode is formed on the organic material layer. The formation of the organic material layer includes forming an organic material layer having one or more layers by using the coating composition according to claim 10.

14. The method of claim 13, wherein forming the organic material layer having one or more layers by using the coating composition comprises: The coating composition is coated onto the first electrode, and The coated composition is subjected to heat treatment or light treatment.

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