Amine compound, coating composition comprising same, organic light emitting device comprising same and method of manufacturing same

Abstract

The present invention relates to a compound represented by Chemical Formula 1, a coating composition comprising the aforementioned compound, an organic light-emitting device comprising the same, and a method for manufacturing the same.

Description

Technology Field

[0001] The present invention relates to an amine compound, a coating composition containing the same, an organic light-emitting device containing the same, and a method for manufacturing the same. Background Technology

[0002] Organic light emission is one example in which electric current is converted into visible light through internal processes of specific organic molecules. The principle of organic light emission is as follows: When an organic layer is placed between an anode and a cathode and an electric current is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and anode, respectively. The electrons and holes injected into the organic layer recombine to form excitons, and as these excitons fall back to the ground state, light is emitted. An organic light-emitting device utilizing this principle can generally be composed of a cathode and an anode and an organic layer located between them, such as a hole injection layer, a hole transport layer, an emissive layer, an electron injection layer, and an electron transport layer.

[0003] Conventionally, deposition processes have been primarily used to manufacture organic light-emitting diodes (OLEDs). However, the deposition process presents challenges such as significant material loss and the difficulty of manufacturing large-area devices; to address these issues, devices utilizing solution processes are being developed.

[0004] Therefore, the development of materials for solution processes is required. Prior art literature

[0005] Korean Patent Publication No. 10-2017-089095 The problem to be solved

[0006] The purpose of the present invention is to provide a compound represented by Chemical Formula 1 of Claim 1.

[0007] The purpose of the present invention is to provide a coating composition comprising the aforementioned compound.

[0008] The purpose of the present invention is to provide an organic light-emitting device comprising the aforementioned compound. means of solving the problem

[0009] One embodiment of the present invention provides a compound represented by the following chemical formula 1.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] L is a substituted or unsubstituted divalent aromatic hydrocarbon ring; or a substituted or unsubstituted divalent heterocyclic ring, and

[0014] L1 and L2 are identical or different from each other, and each is independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0015] Ar1 and Ar2 are identical or different from each other, and each is an independently substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0016] L11 to L14 are identical or different from each other and are each independently substituted or unsubstituted arylene groups, and

[0017] Either X1 or X2 is a haloaryl group, and the other is a curing group, and

[0018] One of X3 and X4 is a haloaryl group, and the other is a curing group, and

[0019] R1 and R2 are identical or different from each other, and each independently is 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 heteroaryl group, and

[0020] n1 and n2 are each integers from 0 to 7, and if n1 and n2 are each 2 or more, the substituents within 2 or more parentheses are identical or different from each other, and

[0021] m1 is the number of bonding positions where a substituent can be bonded to 0 to Ar1, and

[0022] m2 is the number of bonding positions where a substituent can be bonded to 0 to Ar2.

[0023] Another embodiment of the present invention provides a coating composition comprising the aforementioned compound.

[0024] Another embodiment of the present invention provides an organic light-emitting device comprising a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the one or more organic layers comprise the aforementioned coating composition or a cured product thereof.

[0025] Another embodiment of the present invention provides a method for manufacturing an organic light-emitting device comprising the steps of: preparing a first electrode; forming one or more organic layers on the first electrode; and forming a second electrode on one or more organic layers, wherein the step of forming the organic layers includes forming one or more organic layers using the coating composition. Effects of the invention

[0026] The compound of Formula 1 of the present invention can be used as a material for the organic layer of an organic light-emitting device, and a device having low driving voltage, excellent current efficiency, or lifespan characteristics can be obtained, or a solution process is possible, making it possible to increase the area of ​​the device.

[0027] In addition, when an organic layer containing the compound of Formula 1 of the present invention is formed and then an upper organic layer is formed through a solution process, the organic layer containing the compound of Formula 1 is not dissolved in the upper solution process solvent, so there is an advantage that the performance of the device is not degraded. Brief explanation of the drawing

[0028] FIG. 1 illustrates an organic light-emitting element according to one embodiment of the present invention. Specific details for implementing the invention

[0029] The present invention will be described in detail below.

[0030] One embodiment of the present invention provides a compound represented by the following chemical formula 1.

[0031] [Chemical Formula 1]

[0032]

[0033] In the above chemical formula 1,

[0034] L is a substituted or unsubstituted divalent aromatic hydrocarbon ring; or a substituted or unsubstituted divalent heterocyclic ring, and

[0035] L1 and L2 are identical or different from each other, and each is independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0036] Ar1 and Ar2 are identical or different from each other, and each is an independently substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0037] L11 to L14 are identical or different from each other and are each independently substituted or unsubstituted arylene groups, and

[0038] Either X1 or X2 is a haloaryl group, and the other is a curing group, and

[0039] One of X3 and X4 is a haloaryl group, and the other is a curing group, and

[0040] R1 and R2 are identical or different from each other, and each independently is 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 heteroaryl group, and

[0041] n1 and n2 are each integers from 0 to 7, and if n1 and n2 are each 2 or more, the substituents within 2 or more parentheses are identical or different from each other, and

[0042] m1 is the number of bonding positions where a substituent can be bonded to 0 to Ar1, and

[0043] m2 is the number of bonding positions where a substituent can be bonded to 0 to Ar2.

[0044] According to one embodiment of the present invention, the compound of Formula 1 includes two types of curable groups (haloaryloxy group and other curable groups) with different structures in fluorene, thereby suppressing radical formation at the corresponding location, which increases the stability of the compound and has a high HOMO (highest occupied molecular orbital) energy level value and excellent hole mobility. As a result, when the compound of Formula 1 is included in the hole injection layer of an organic light-emitting device, it facilitates hole injection from the hole injection layer to the hole transport layer, thereby providing the advantage of obtaining an organic light-emitting device with long lifespan characteristics.

[0045] In the present invention, when it is said that a certain member (layer) is located "on" another member (layer), this includes not only the case where a certain member (layer) is in contact with another member, but also the case where another member (layer) exists between the two members (layers).

[0046] In the present invention, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0047] In the present invention, the term "layer" is used in the sense of a "film" commonly used in the art and refers to a coating that covers a target area. The size of the "layer" is not limited, and each "layer" may have the same or different sizes. According to one embodiment, the size of the "layer" may be equal to the size of the entire device, correspond to the size of a specific functional area, or be as small as a single subpixel.

[0048] Unless otherwise defined in this invention, all technical and scientific terms used in this invention have the same meaning as commonly understood by those skilled in the art to which this invention pertains. Methods and materials similar or equivalent to those described in this invention may be used in the practice or testing of embodiments of this invention, but suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned in this invention are incorporated by reference in their entirety to this invention, and in the event of conflict, this invention, including definitions, shall prevail unless a specific passage is mentioned. Furthermore, materials, methods, and embodiments are merely illustrative and are not intended to be limiting.

[0049] In the present invention, the term "combination thereof" included in a Markush-style expression means one or more mixtures or combinations selected from a group consisting of components described in the Markush-style expression, and means including one or more selected from the group consisting of said components.

[0050] Examples of substituents in the present invention are described below, but are not limited thereto.

[0051] In the present invention, "-----" refers to each connected part.

[0052] In the present invention, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution location is not limited to the location where the hydrogen atom is substituted, that is, any location where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0053] In the present invention, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of hydrogen; deuterium; halogen group; amine group; alkyl group; aryl group; and heteroaryl group, or is substituted with a substituent in which two or more of the exemplified substituents are connected, or has no substituents.

[0054] In the present invention, the connection of two or more substituents means that a hydrogen of one substituent is connected to another substituent. For example, an isopropyl group and a phenyl group are connected or It can be a substituent of.

[0055] In the present invention, the connection of three substituents includes not only the case where (substituent 1)-(substituent 2)-(substituent 3) are connected in succession, but also the case where (substituent 2) and (substituent 3) are connected to (substituent 1). For example, two phenyl groups and isopropyl groups are connected or It can be a substituent. The same applies to the connection of 4 or more substituents as described above.

[0056] In the present invention, the halogen group is a fluoro group (-F), a chloro group (-Cl), a bromo group (-Br), or an iodo group (-I).

[0057] In the present invention, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30; 1 to 20; 1 to 10; or 1 to 5. Specific examples include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl. The above alkyl group may include a haloalkyl group, which is an alkyl group substituted with a halogen group. Specific examples include a methyl group substituted with three fluoro groups, namely a trifluoromethyl group, but are not limited thereto.

[0058] In the present invention, an aryl group refers to a monovalent aromatic hydrocarbon or a derivative of an aromatic hydrocarbon. In the present invention, an aromatic hydrocarbon refers to a compound comprising a planar ring in which pi electrons are completely conjugated, and a group derived from an aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed to an aromatic hydrocarbon. Furthermore, in the present invention, the aryl group is intended to include a monovalent group in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are connected to each other. The aryl group is not particularly limited, but it is preferable that it has 6 to 60 carbon atoms; 6 to 50; 6 to 30; 6 to 25; 6 to 20; 6 to 18; 6 to 15; 6 to 13; or 6 to 12 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group.

[0059] The above monocyclic aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms; 6 to 54; 6 to 48; 6 to 42; 6 to 36; 6 to 30; 6 to 24; 6 to 18; or 6 to 12 carbon atoms, and specifically may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

[0060] The above polycyclic aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms; 6 to 45 carbon atoms; 6 to 30 carbon atoms; 6 to 22 carbon atoms; 6 to 22 carbon atoms; 6 to 20 carbon atoms; 6 to 18 carbon atoms; 6 to 16 carbon atoms; 6 to 15 carbon atoms; 6 to 14 carbon atoms; 6 to 13 carbon atoms; 6 to 12 carbon atoms; or 6 to 10 carbon atoms. It may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

[0061] In the present invention, the aryl group may include a haloaryl group substituted with a halogen group. The haloaryl group refers to an aryl group substituted with one or more halogen groups, and the haloaryl group may be an aryl group substituted with one or more substituents selected from the group consisting of a fluoro group, a chloro group, a bromo group, and an iodo group. Additionally, the haloaryl group may be substituted with two or more identical halogen groups, and, for example, may be an aryl group substituted with one fluoro group as well as an aryl group substituted with two or more fluoro groups.

[0062] In the present invention, a heteroaryl group refers to a monovalent aromatic heterocyclic group. Here, an aromatic heterocyclic group refers to a monovalent group of an aromatic ring or a derivative of an aromatic ring, comprising one or more heteroatoms selected from the group consisting of N, O, P, S, Si, and Se. The derivative of the aromatic ring includes all structures in which an aromatic ring or an aliphatic ring is condensed to an aromatic ring. Furthermore, in the present invention, the heteroaryl group is intended to include a monovalent group in which two or more aromatic rings containing heteroatoms or derivatives of aromatic rings containing heteroatoms are connected to each other. It is preferable that the number of carbon atoms of the heteroaryl group be 2 to 60; 2 to 50; 2 to 30; 2 to 20; 2 to 18; or 2 to 13. Examples of heteroaryl groups include, but are not limited to, thiophene, furanyl, pyrrole, imidazole, thiazole, oxazole, pyridine, pyrimidine, triazine, triazole, acridine, pyridazine, pyrazine, quinoline, quinazolin, quinoxaline, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophen, dibenzothiophen, benzofuran, phenanthrolinyl, and dibenzofuran groups.

[0063] In the present invention, the heteroaryl group may be a monocyclic or polycyclic ring and may be an aromatic, aliphatic, or a condensed ring of aromatic and aliphatic.

[0064] In the present invention, a heterocyclic group is a monovalent group of an aliphatic ring, a derivative of an aliphatic ring, an aromatic ring, or a derivative of an aromatic ring, and means a group comprising one or more heteroatoms selected from the group consisting of N, O, P, S, Si, and Se.

[0065] In the present invention, the aliphatic ring is a non-aromatic hydrocarbon ring, and examples include the aforementioned cycloalkyl group, adamantyl group, etc.

[0066] In the present invention, the aromatic ring may be subject to the aforementioned aryl group.

[0067] In the present invention, the hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of aromatic and aliphatic. Examples of condensed rings of aromatic and aliphatic include, but are not limited to, 1,2,3,4-tetrahydronaphthalene groups and 2,3-dihydro-1H-indene groups.

[0068] In the present invention, the description of the heterocyclic group may apply except that the heterocyclic group is divalent.

[0069] In the present invention, the description of the aryl group described above may apply except that the aromatic hydrocarbon ring is a divalent group.

[0070] In the present invention, the description of the cycloalkyl group described above may apply except that the aliphatic hydrocarbon ring is a divalent group.

[0071] In the present invention, "adjacent group" may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the atom in stereostructure, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

[0072] According to one embodiment of the present invention, the above chemical formula 1 is represented by the following chemical formula 2.

[0073] [Chemical Formula 2]

[0074]

[0075] In the above chemical formula 2,

[0076] L, L1, L2, Ar1, Ar2, L11 to L14, X1 to X4, R1, R2, n1, n2, m1 and m2 are as defined in Chemical Formula 1.

[0077] According to one embodiment of the present invention, the above chemical formula 1 is represented by the following chemical formula 3.

[0078] [Chemical Formula 3]

[0079]

[0080] In the above chemical formula 3,

[0081] L, L1, L2, Ar1, Ar2, X1 to X4, R1, R2, n1, n2, m1 and m2 are as defined in Chemical Formula 1.

[0082] According to one embodiment of the present invention, the above chemical formula 1 is represented by the following chemical formula 4.

[0083] [Chemical Formula 4]

[0084]

[0085] In the above chemical formula 4,

[0086] m3 is an integer from 1 to 5, and

[0087] m4 is an integer from 1 to 5, and

[0088] L, L1, L2, Ar1, Ar2, X1, X3, R1, R2, n1, n2, m1 and m2 are as defined in Chemical Formula 1.

[0089] According to one embodiment of the present invention, L is a substituted or unsubstituted divalent aromatic hydrocarbon ring; or a substituted or unsubstituted divalent heterocyclic ring.

[0090] According to one embodiment of the present invention, L is a divalent aromatic hydrocarbon ring group substituted or unsubstituted with an alkyl group; or a divalent heterocyclic ring group substituted or unsubstituted with an alkyl group.

[0091] According to one embodiment of the present invention, L is a divalent aromatic hydrocarbon ring group substituted or unsubstituted with an alkyl group.

[0092] According to one embodiment of the present invention, L is a divalent aromatic hydrocarbon ring group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.

[0093] According to one embodiment of the present invention, L is a divalent aromatic hydrocarbon ring group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

[0094] According to one embodiment of the present invention, L is a divalent aromatic hydrocarbon ring group substituted or unsubstituted with an alkyl group having 1 to 8 carbon atoms.

[0095] According to one embodiment of the present invention, L is a divalent aromatic hydrocarbon ring group having 6 to 30 carbon atoms that is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.

[0096] According to one embodiment of the present invention, L is a divalent aromatic hydrocarbon ring group having 6 to 26 carbon atoms that is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.

[0097] According to one embodiment of the present invention, L is any one selected from the following structures.

[0098]

[0099] In the above structures, ---- represents a position connected to N of the above chemical formula 1, and

[0100] The above structures are substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryl group; and substituted or unsubstituted heteroaryl group. In a specific example, the structures are substituted or unsubstituted with deuterium; halogen group; or substituted or unsubstituted alkyl group. In a more specific example, the structures are substituted or unsubstituted with deuterium; halogen group; or substituted or unsubstituted C1 to C10 alkyl group. In yet another specific example, the structures are substituted or unsubstituted with C1 to C10 alkyl group.

[0101] According to one embodiment of the present invention, L is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylylene group; a substituted or unsubstituted terphenylylene group; or a substituted or unsubstituted divalent spirobifluorene.

[0102] According to one embodiment of the present invention, L is a substituted or unsubstituted biphenylylene group; a substituted or unsubstituted terphenylylene group; or a substituted or unsubstituted divalent spirobifluorene.

[0103] According to one embodiment of the present invention, L is a biphenylylene group substituted or unsubstituted with an alkyl group; a terphenylylene group substituted or unsubstituted with an alkyl group; or a divalent spirobifluorene substituted or unsubstituted with an alkyl group.

[0104] According to one embodiment of the present invention, L is a biphenylylene group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms; a terphenylylene group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms; or a divalent spirobifluorene substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.

[0105] According to one embodiment of the present invention, L is a biphenylylene group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; a terphenylylene group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; or a divalent spirobifluorene substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

[0106] According to one embodiment of the present invention, L is a biphenyllylene group; a terphenyllylene group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; or a divalent spirobifluorene.

[0107] According to one embodiment of the present invention, L is a biphenyllylene group; a terphenyllylene group substituted or unsubstituted with a hexyl group; or a divalent spirobifluorene.

[0108] According to one embodiment of the present invention, L is a biphenyllylene group; a terphenyllylene group substituted or unsubstituted with an n-hexyl group; or a divalent spirobifluorene.

[0109] According to one embodiment of the present invention, L is a biphenyllylene group; a terphenyllylene group substituted or unsubstituted with two n-hexyl groups; or a divalent spirobifluorene.

[0110] According to one embodiment of the present invention, L1 and L2 are identical or different from each other and are each independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

[0111] According to one embodiment of the present invention, L1 and L2 are identical or different from each other and are each independently directly bonded; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0112] According to one embodiment of the present invention, L1 and L2 are identical or different from each other and are each independently directly bonded; a substituted or unsubstituted arylene group having 6 to 26 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 26 carbon atoms.

[0113] According to one embodiment of the present invention, L1 and L2 are identical or different from each other and are each independently directly bonded; an arylene group; or a heteroarylene group.

[0114] According to one embodiment of the present invention, L1 and L2 are identical or different from each other and are each independently directly bonded; or are arylene groups.

[0115] According to one embodiment of the present invention, L1 and L2 are directly coupled.

[0116] According to one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are each independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups.

[0117] According to one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 30 carbon atoms; or substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms.

[0118] According to one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are each independently substituted or unsubstituted aryl groups.

[0119] According to one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0120] According to one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.

[0121] According to one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 18 carbon atoms.

[0122] According to one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted terphenyl group.

[0123] According to one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are each independently a phenyl group substituted or unsubstituted with an alkyl group; a biphenyl group substituted or unsubstituted with an alkyl group; or a terphenyl group substituted or unsubstituted with an alkyl group.

[0124] According to one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are each independently a phenyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; a biphenyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; or a terphenyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

[0125] According to one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are each independently a phenyl group substituted or unsubstituted with an alkyl group; a biphenyl group; or a terphenyl group.

[0126] According to one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are each independently a phenyl group; a biphenyl group; or a terphenyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

[0127] According to one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are each independently a phenyl group substituted or unsubstituted with a methyl group; a biphenyl group; or a terphenyl group.

[0128] According to one embodiment of the present invention, L11 to L14 are identical or different from each other and are each independently substituted or unsubstituted arylene groups.

[0129] According to one embodiment of the present invention, L11 to L14 are identical or different from each other and are each independently substituted or unsubstituted arylene groups having 6 to 30 carbon atoms.

[0130] According to one embodiment of the present invention, L11 to L14 are identical or different from each other and are each independently substituted or unsubstituted arylene groups having 6 to 20 carbon atoms.

[0131] According to one embodiment of the present invention, L11 to L14 are identical or different from each other and are each independently substituted or unsubstituted arylene groups having 6 to 12 carbon atoms.

[0132] According to one embodiment of the present invention, L11 to L14 are identical or different from each other and are each independently substituted or unsubstituted phenylene groups.

[0133] According to one embodiment of the present invention, L11 to L14 are phenylene groups.

[0134] According to one embodiment of the present invention, X1 to X4 are identical or different from each other and are each independently a haloaryl group or a curable group.

[0135] The above-mentioned hardening group is any one selected from the group consisting of the following structures.

[0136]

[0137] In the above structures, --- refers to a position connected to the above chemical formula 1.

[0138] According to another embodiment of the present invention, the curable group is any one selected from the group consisting of the following structures.

[0139]

[0140] In the above structures, --- refers to a position connected to the above chemical formula 1.

[0141] According to a preferred embodiment of the present invention, the curable group has the following structure.

[0142]

[0143] In the above structure, --- refers to a position connected to the above chemical formula 1.

[0144] The description of the curable period described above may be applied when X1 to X4, which will be described later, are curable periods.

[0145] According to one embodiment of the present invention, either X1 or X2 is a haloaryl group, and the other is a curable group.

[0146] According to one embodiment of the present invention, either X1 or X2 is an aryl group substituted with a fluorogroup, and the other is a curable group.

[0147] According to one embodiment of the present invention, either X1 or X2 is an aryl group having 6 to 30 carbon atoms substituted with a fluorogroup, and the other is a curable group.

[0148] According to one embodiment of the present invention, either X1 or X2 is an aryl group having 6 to 20 carbon atoms substituted with a fluorogroup, and the other is a curable group.

[0149] According to one embodiment of the present invention, either X1 or X2 is a phenyl group substituted with a fluoro group, and the other is the following structure.

[0150]

[0151] In the above structure, --- refers to a position connected to the above chemical formula 1.

[0152] According to one embodiment of the present invention, either X3 or X4 is a haloaryl group, and the other is a curable group.

[0153] According to one embodiment of the present invention, either X3 or X4 is an aryl group substituted with a fluorogroup, and the other is a curable group.

[0154] According to one embodiment of the present invention, either X3 or X4 is an aryl group having 6 to 30 carbon atoms substituted with a fluorogroup, and the other is a curable group.

[0155] According to one embodiment of the present invention, either X3 or X4 is an aryl group having 6 to 20 carbon atoms substituted with a fluorogroup, and the other is a curable group.

[0156] According to one embodiment of the present invention, either X3 or X4 is a phenyl group substituted with a fluoro group, and the other is the following structure.

[0157]

[0158] In the above structure, --- refers to a position connected to the above chemical formula 1.

[0159] According to one embodiment of the present invention, either X1 or X2 is a phenyl group substituted with a fluorogroup, and the other is the structure below, and either X3 or X4 is a phenyl group substituted with a fluorogroup, and the other is the structure below.

[0160]

[0161] In the above structure, --- refers to a position connected to the above chemical formula 1.

[0162] As described above, the compound according to the present invention can improve the stability of the compound by including fluorene in which both fluorophenoxy groups and vinylphenoxy groups, which are curable groups of different structures, are introduced into the compound.

[0163] According to one embodiment of the present invention, R1 to R4 are identical or different from each other and are each independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group.

[0164] According to one embodiment of the present invention, R1 to R4 are identical or different from each other and are each independently hydrogen or deuterium.

[0165] According to one embodiment of the present invention, R1 to R4 are hydrogen.

[0166] According to one embodiment of the present invention, n1 and n2 are each integers from 0 to 7.

[0167] According to one embodiment of the present invention, n1 is an integer of 0. According to another embodiment of the present invention, n1 is an integer of 1. According to yet another embodiment of the present invention, n1 is an integer of 2. According to yet another embodiment of the present invention, n1 is an integer of 3. According to yet another embodiment of the present invention, n1 is an integer of 4. According to yet another embodiment of the present invention, n1 is an integer of 5. According to yet another embodiment of the present invention, n1 is an integer of 6. According to yet another embodiment of the present invention, n1 is an integer of 7.

[0168] According to one embodiment of the present invention, n2 is an integer of 0. According to another embodiment of the present invention, n2 is an integer of 1. According to yet another embodiment of the present invention, n2 is an integer of 2. According to yet another embodiment of the present invention, n2 is an integer of 3. According to yet another embodiment of the present invention, n2 is an integer of 4. According to yet another embodiment of the present invention, n2 is an integer of 5. According to yet another embodiment of the present invention, n2 is an integer of 6. According to yet another embodiment of the present invention, n2 is an integer of 7.

[0169] According to one embodiment of the present invention, when n1 and n2 are each 2 or more, the substituents within the 2 or more parentheses are identical or different from each other.

[0170] According to one embodiment of the present invention, m1 is the number of bonding positions to which a substituent can be attached to Ar1 from 0 to Ar2, and m2 is the number of bonding positions to which a substituent can be attached to Ar2 from 0 to Ar2. In this case, the number of bonding positions to which a substituent can be attached to Ar1 or Ar2 refers to the number of hydrogens attached to Ar1 or Ar2. For example, if Ar1 or Ar2 is a phenyl group, since 5 hydrogens are attached to the phenyl group, the number of bonding positions to which a substituent can be attached to Ar1 or Ar2 is 5. As another example, if Ar1 or Ar2 is a biphenyl group, since 9 hydrogens are attached to the biphenyl group, the number of bonding positions to which a substituent can be attached to Ar1 or Ar2 is 9.

[0171] According to one embodiment of the present invention, m1 and m2 are each integers from 0 to 13.

[0172] According to one embodiment of the present invention, m1 is an integer of 0. According to another embodiment of the present invention, m1 is an integer of 1. According to yet another embodiment of the present invention, m1 is an integer of 2. According to yet another embodiment of the present invention, m1 is an integer of 3. According to yet another embodiment of the present invention, m1 is an integer of 4. According to yet another embodiment of the present invention, m1 is an integer of 5. According to yet another embodiment of the present invention, m1 is an integer of 6. According to yet another embodiment of the present invention, m1 is an integer of 7. According to yet another embodiment of the present invention, m1 is an integer of 8. According to yet another embodiment of the present invention, m1 is an integer of 9. According to yet another embodiment of the present invention, m1 is an integer of 10. According to yet another embodiment of the present invention, m1 is an integer of 11. According to another embodiment of the present invention, m1 is an integer of 12. According to another embodiment of the present invention, m1 is an integer of 13. According to a preferred embodiment of the present invention, m1 is an integer of 1 to 5. According to another preferred embodiment of the present invention, m1 is an integer of 1, 2, 3, or 5.

[0173] According to one embodiment of the present invention, m2 is an integer of 0. According to another embodiment of the present invention, m2 is an integer of 1. According to yet another embodiment of the present invention, m2 is an integer of 2. According to yet another embodiment of the present invention, m2 is an integer of 3. According to yet another embodiment of the present invention, m2 is an integer of 4. According to yet another embodiment of the present invention, m2 is an integer of 5. According to yet another embodiment of the present invention, m2 is an integer of 6. According to yet another embodiment of the present invention, m2 is an integer of 7. According to yet another embodiment of the present invention, m2 is an integer of 8. According to yet another embodiment of the present invention, m2 is an integer of 9. According to yet another embodiment of the present invention, m2 is an integer of 10. According to yet another embodiment of the present invention, m2 is an integer of 11. According to another embodiment of the present invention, m2 is an integer of 12. According to another embodiment of the present invention, m2 is an integer of 13. According to a preferred embodiment of the present invention, m2 is an integer of 1 to 5. According to another preferred embodiment of the present invention, m2 is an integer of 1, 2, 3, or 5.

[0174] According to one embodiment of the present invention, m3 is an integer of 1. According to another embodiment of the present invention, m3 is an integer of 2. According to yet another embodiment of the present invention, m3 is an integer of 3. According to yet another embodiment of the present invention, m3 is an integer of 4. According to yet another embodiment of the present invention, m3 is an integer of 5. According to a preferred embodiment of the present invention, m3 is an integer of 1 or 2.

[0175] According to one embodiment of the present invention, m4 is an integer of 1. According to another embodiment of the present invention, m4 is an integer of 2. According to yet another embodiment of the present invention, m4 is an integer of 3. According to yet another embodiment of the present invention, m4 is an integer of 4. According to yet another embodiment of the present invention, m4 is an integer of 5. According to a preferred embodiment of the present invention, m4 is an integer of 1 or 2.

[0176] According to one embodiment of the present invention, the compound represented by the chemical formula 1 is any one selected from the group consisting of the following compounds.

[0177] .

[0178] One embodiment of the present invention provides a coating composition comprising a compound of the aforementioned chemical formula 1.

[0179] According to one embodiment of the present invention, the coating composition comprises a compound of Formula 1 and a solvent.

[0180] According to one embodiment of the present invention, the coating composition may be in a liquid state.

[0181] According to one embodiment of the present invention, the solvent is, for example, a chlorine-based solvent such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene; an ether-based solvent such as tetrahydrofuran, dioxane; an aromatic hydrocarbon-based solvent such as toluene, xylene, trimethylbenzene, mesitylene; an aliphatic hydrocarbon-based solvent such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane; a ketone-based solvent such as acetone, methyl ethyl ketone, cyclohexanone, isophorone, tetralon, decalone, acetylacetone; an ester-based solvent such as ethyl acetate, butyl acetate, ethyl cellosolve acetate; Polyhydric alcohols and derivatives thereof such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol; alcohol-based solvents such as methanol, ethanol, propanol, isopropanol, cyclohexanol; sulfoxide-based solvents such as dimethyl sulfoxide; and amide-based solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide; and solvents such as tetralin are exemplified, but any solvent capable of dissolving or dispersing the compound of Formula 1 according to one embodiment of the present invention is sufficient and is not limited thereto.

[0182] According to one embodiment of the present invention, the solvent may be used alone or a mixture of two or more solvents.

[0183] According to one embodiment of the present invention, the coating composition does not further include a p-doping material.

[0184] According to one embodiment of the present invention, the coating composition further comprises a p-doping material.

[0185] In the present invention, the p-doping material refers to a material that causes a host material to have p-semiconductor characteristics. The p-semiconductor characteristic refers to a characteristic of receiving or transporting holes to the HOMO (highest occupied molecular orbital) energy level, that is, a characteristic of a material with high hole conductivity.

[0186] The above p-doping material may be any one of the following structures, but is not limited thereto.

[0187]

[0188]

[0189] According to one embodiment of the present invention, the content of the p-doping material is 0% to 50% by weight based on the compound of Formula 1; or 10% to 30% by weight.

[0190] According to one embodiment of the present invention, the weight ratio of the compound of Formula 1 and the p-doping material is 9:1 to 1:9. As a preferred embodiment, the weight ratio of the compound of Formula 1 and the p-doping material is 9:1 to 7:3. As a specific example, the weight ratio of the compound of Formula 1 and the p-doping material is 8:2.

[0191] According to one embodiment of the present invention, the content of the p-doping material comprises 0 to 30 weight% based on the total solid content of the coating composition.

[0192] According to one embodiment of the present invention, the content of the p-doping material preferably comprises 1 to 30 weight percent based on the total solid content of the coating composition.

[0193] According to another embodiment of the present invention, the coating composition further comprises a monomer comprising a photocurable group and / or a thermosetting group; or a monomer comprising a terminal group capable of forming a polymer by heat. As described above, the molecular weight of the monomer comprising a photocurable group and / or a thermosetting group; or the monomer comprising a terminal group capable of forming a polymer by heat may be a compound having a molecular weight of 3,000 g / mol or less, but is not limited to the molecular weight exemplified above.

[0194] A monomer comprising the above-mentioned photocurable group and / or thermocurable group; or a monomer comprising a terminal group capable of forming a polymer by heat may mean an aryl such as phenyl, biphenyl, fluorene, naphthalene; an arylamine; or a monomer in which a photocurable group and / or thermocurable group or a terminal group capable of forming a polymer by heat is substituted on fluorene.

[0195] According to one embodiment of the present invention, the viscosity of the coating composition is 2 cP to 15 cP at room temperature. When the above viscosity is satisfied, it is easy to manufacture the device. Specifically, a uniform film can be formed when forming an organic layer in an organic light-emitting device.

[0196] According to one embodiment of the present invention, the coating composition is in a state cured by heat treatment or phototreatment, and is referred to as a cured product of the coating composition.

[0197] One embodiment of the present invention provides an organic light-emitting device comprising: a compound of Formula 1; or a coating composition comprising a compound of Formula 1 or a cured product thereof.

[0198] One embodiment of the present invention provides an organic light-emitting device formed using the coating composition or a cured product thereof.

[0199] One embodiment of the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the one or more organic layers comprises the aforementioned coating composition or a cured product thereof. In this case, the cured product of the coating composition refers to a state in which the coating composition is cured by heat treatment or phototreatment.

[0200] Below, the types of organic layers included in the aforementioned organic light-emitting device are specifically described.

[0201] According to one embodiment of the present invention, the organic light-emitting element comprises one organic layer, and the organic layer comprises a compound of Formula 1; or a coating composition or a cured product thereof comprising a compound of Formula 1. As an example, the organic layer comprising a compound of Formula 1; or a coating composition or a cured product thereof comprising a compound of Formula 1 is a light-emitting layer.

[0202] According to another embodiment of the present invention, the organic light-emitting element comprises two or more organic layers, and the two or more organic layers comprise a compound of Formula 1; or a coating composition or a cured product thereof comprising a compound of Formula 1. For example, any one of the two or more organic layers comprises a compound of Formula 1; or a coating composition or a cured product thereof comprising a compound of Formula 1, and further comprises one or more remaining organic layers. According to one embodiment, the remaining one or more organic layers do not comprise a compound of Formula 1; or a coating composition or a cured product thereof comprising a compound of Formula 1. According to another embodiment, the remaining one or more organic layers further comprise a compound of Formula 1; or a coating composition or a cured product thereof comprising a compound of Formula 1. However, the invention is not limited to the above examples.

[0203] The above two or more organic layers comprise, for example, two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, etc. In this case, the hole injection and transport layer refers to a layer that performs hole injection and hole transport simultaneously, and the electron injection and transport layer refers to a layer that performs electron injection and electron transport simultaneously. However, the organic layers forming the above group are merely examples and are not limited to the above examples. Additionally, the above two or more organic layers may include two or more layers that perform the same function as needed. An organic light-emitting device according to one example includes a first hole injection layer and a second hole injection layer. However, it is not limited to the above examples.

[0204] According to one embodiment of the present invention, the organic layer comprises a light-emitting layer. As an example, the light-emitting layer comprises a compound of Formula 1; or a coating composition or a cured product thereof comprising a compound of Formula 1. As a specific example, the light-emitting layer comprises a compound of Formula 1 as a host of the light-emitting layer. As another specific example, the light-emitting layer comprises a compound of Formula 1 as a dopant of the light-emitting layer.

[0205] According to one embodiment of the present invention, the organic layer comprises a hole injection and transport layer, a hole injection layer, or a hole transport layer. As an example, the hole injection and transport layer, the hole injection layer, or the hole transport layer comprises a compound of Formula 1; or a coating composition or a cured product thereof comprising a compound of Formula 1.

[0206] According to one embodiment of the present invention, the organic layer comprises a hole injection layer. As an example, the hole injection layer comprises a compound of Formula 1; or a coating composition or a cured product thereof comprising a compound of Formula 1.

[0207] According to one embodiment of the present invention, the organic layer further comprises one or more layers selected from the group consisting of an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer. As an example, one or more layers selected from the group consisting of the electron blocking layer, the hole blocking layer, the electron transport layer, the electron injection layer, and the electron injection and transport layer comprise a compound of Formula 1; or a coating composition or a cured product thereof comprising a compound of Formula 1. As another example, one or more layers selected from the group consisting of the electron blocking layer, the hole blocking layer, the electron transport layer, the electron injection layer, and the electron injection and transport layer do not comprise a compound of Formula 1; or a coating composition or a cured product thereof comprising a compound of Formula 1.

[0208] One embodiment of the present invention comprises a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, and

[0209] The above organic layer includes a light-emitting layer and a hole injection layer, and

[0210] The present invention provides an organic light-emitting device comprising a hole injection layer comprising a compound of Formula 1; or a coating composition comprising a compound of Formula 1 or a cured product thereof.

[0211] Below, the stacked structure of the organic layer and the organic light-emitting device containing it is specifically described.

[0212] According to one embodiment of the present invention, the organic layer of an organic light-emitting device has a single-layer structure. For example, the single-layer organic layer is provided between a first electrode and a second electrode of the organic light-emitting device, and the organic layer comprises a compound of Formula 1; or a coating composition or a cured product thereof comprising a compound of Formula 1. According to a specific embodiment, the organic layer formed by the single-layer structure is a light-emitting layer, wherein the light-emitting layer comprises a compound of Formula 1.

[0213] According to another embodiment of the present invention, the organic layer of the organic light-emitting device is a multilayer structure in which two or more organic layers are stacked. For example, the organic layer of the multilayer structure is provided between the first electrode and the second electrode of the organic light-emitting device.

[0214] According to one embodiment of the present invention, the organic layer of the multilayer structure comprises a light-emitting layer and an organic layer other than the light-emitting layer. In one example, the light-emitting layer is provided between a first electrode and a second electrode, and the organic layer other than the light-emitting layer is provided between the first electrode and the light-emitting layer. In another example, the light-emitting layer is provided between the first electrode and the second electrode, and the organic layer other than the light-emitting layer is provided between the light-emitting layer and the second electrode. In yet another example, the light-emitting layer is provided between the first electrode and the second electrode, any one organic layer other than the light-emitting layer is provided between the first electrode and the light-emitting layer, and any other organic layer other than the light-emitting layer is provided between the light-emitting layer and the second electrode. However, the above structure is merely an example and is not limited to the above structure. In addition, the organic layer other than the above-mentioned light-emitting layer may be one or more layers selected from the group consisting of, for example, a hole injection and transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, but is not limited thereto.

[0215] Generally, in organic light-emitting diodes, a hole injection layer, a hole transport layer, or an electron blocking layer is provided between the anode and the light-emitting layer. As a specific example, the hole injection layer is provided above the anode, the hole transport layer is provided above the hole injection layer, and the electron blocking layer is provided above the hole injection layer, but is not limited to the above example.

[0216] In addition, generally, in organic light-emitting diodes, an electron injection layer, an electron transport layer, or a hole blocking layer is provided between the cathode and the light-emitting layer. As a specific example, the hole blocking layer is provided on top of the light-emitting layer, the electron transport layer is provided on top of the hole blocking layer, and the electron injection layer is provided on top of the electron transport layer, but is not limited to the above example.

[0217] An organic material layer having a multilayer structure included in an organic light-emitting device according to one embodiment of the present invention comprises: one or more layers selected from the group consisting of a hole injection and transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer; and a light-emitting layer, wherein the light-emitting layer is provided between a first electrode and a second electrode, and the first electrode is provided between the first electrode and the light-emitting layer, and the one or more layers comprise a compound of Formula 1; or a coating composition or a cured product thereof comprising a compound of Formula 1.

[0218] According to one embodiment of the present invention, the one or more organic layers comprise one or more layers selected from the group consisting of a hole injection layer; a hole transport layer; and a hole injection and transport layer, and the one or more layers selected from the group consisting of a hole injection layer; a hole transport layer; and a hole injection and transport layer comprise a compound of Formula 1; or a coating composition or a cured product thereof comprising a compound of Formula 1.

[0219] The structure of an organic light-emitting device according to one embodiment of the present invention is illustrated in FIG. 1. FIG. 1 illustrates the structure of an organic light-emitting device in which a first electrode (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 second electrode (701) are sequentially stacked on a substrate (101). The hole injection layer (301) and / or the hole transport layer (401) of FIG. 1 may comprise a compound of Formula 1; or a coating composition containing a compound of Formula 1 or a cured product thereof, or may be formed using the coating composition. In this case, the fact that the hole injection layer (301) and / or the hole transport layer (401) of FIG. 1 may be formed using the coating composition will be described later in the specific details of the organic layer, its materials, and manufacturing method. In addition, Figure 1 above illustrates an organic light-emitting element according to one embodiment of the present invention, but is not limited thereto.

[0220] As described above, an organic light-emitting device having a single-layer or multi-layer organic layer structure may have a stacked structure such as the following, but is not limited thereto.

[0221] (1) Anode / hole transport layer / emissive layer / cathode

[0222] (2) Anode / hole injection layer / hole transport layer / emissive layer / cathode

[0223] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / cathode

[0224] (4) Anode / hole transport layer / emissive layer / electron transport layer / cathode

[0225] (5) Anode / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0226] (6) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / cathode

[0227] (7) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0228] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / cathode

[0229] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0230] (10) Anode / hole transport layer / electron blocking layer / emissive layer / electron transport layer / cathode

[0231] (11) Anode / hole transport layer / electron blocking layer / emissive layer / electron transport layer / electron injection layer / cathode

[0232] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / emissive layer / electron transport layer / cathode

[0233] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / emissive layer / electron transport layer / electron injection layer / cathode

[0234] (14) Anode / hole transport layer / emissive layer / hole blocking layer / electron transport layer / cathode

[0235] (15) Anode / hole transport layer / emissive layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0236] (16) Anode / hole injection layer / hole transport layer / emissive layer / hole blocking layer / electron transport layer / cathode

[0237] (17) Anode / hole injection layer / hole transport layer / emissive layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0238] (18) Anode / hole injection layer / hole transport layer / emissive layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capsule

[0239] (19) Anode / hole injection layer / first hole transport layer / second hole transport layer / emissive layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capsule

[0240] According to one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.

[0241] According to another embodiment of the present invention, the first electrode is a cathode and the second electrode is an anode.

[0242] According to one embodiment of the present invention, the organic light-emitting device may be an organic light-emitting device of a normal type structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0243] According to another embodiment of the present invention, the organic light-emitting device may be an inverted type organic light-emitting device in which a canode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0244] The specific details of the aforementioned organic layer, its materials, and manufacturing methods are described below. However, the organic light-emitting device of the present invention may be manufactured using materials and methods known in the art, except that the organic layer comprises the aforementioned compound.

[0245] An organic light-emitting device according to one embodiment of the present invention is formed by using a coating composition comprising one or more layers of the organic material layer, wherein the organic material layer comprises a compound of Formula 1. Except for this, it can be manufactured using materials and methods known in the art.

[0246] For example, the organic light-emitting device of the present invention can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. In this case, the device can be manufactured by forming an anode 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, and then forming an organic layer comprising one or more layers among a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, an electron transport layer, a hole transport and injection layer, and an electron transport and injection layer through a solution process or a deposition process, and then depositing a material that can be used as a cathode on top of it. In addition to this method, an organic light-emitting device can be made by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0247] One embodiment of the present invention also provides a method for manufacturing an organic light-emitting device formed using the coating composition.

[0248] Specifically, according to one embodiment of the present invention, the method comprises the steps of: preparing a first electrode; forming one or more organic layers on the first electrode; and forming a second electrode on the one or more organic layers, wherein the step of forming one or more organic layers includes forming an organic layer using the coating composition.

[0249] According to one embodiment of the present invention, the step of forming one or more organic layers using the coating composition utilizes a spin coating method.

[0250] According to another embodiment of the present invention, the step of forming one or more organic layers using the coating composition utilizes a printing method.

[0251] According to one embodiment of the present invention, the printing method may be, for example, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing, but is not limited to the printing methods listed above.

[0252] The coating composition according to one embodiment of the present invention is suitable for a solution process due to its structural characteristics and can be formed by a printing method, thus providing economic benefits in terms of time and cost during the manufacture of the device.

[0253] According to one embodiment of the present invention, the step of forming one or more organic layers using the coating composition comprises: a step of coating the coating composition; and a step of heat-treating or photo-treating the coated coating composition. Alternatively, the step of forming an organic layer using the coating composition comprises: a step of coating the coating composition; and a step of heat-treating or photo-treating the coated coating composition.

[0254] According to one embodiment of the present invention, the step of forming one or more organic layers using the coating composition comprises: a step of coating the coating composition on the first electrode or one or more organic layers; and a step of heat treating or phototreating the coated coating composition.

[0255] According to one embodiment of the present invention, the heat treatment step may be performed through heat treatment, and the heat treatment temperature in the heat treatment step may be 85 ℃ to 250 ℃, according to one embodiment may be 100 ℃ to 250 ℃, and in another embodiment may be 150 ℃ to 250 ℃.

[0256] According to one embodiment of the present invention, the heat treatment time in the heat treatment step is 1 minute to 2 hours, according to one embodiment it may be 1 minute to 1 hour, and in another embodiment it may be 10 minutes to 1 hour. As a preferred example, the heat treatment time in the heat treatment step is 20 minutes to 40 minutes.

[0257] In the step of forming one or more organic layers using the above coating composition, if the heat treatment or phototreatment step is included, a plurality of the compounds included in the coating composition may form crosslinks to provide an organic layer having a thin film structure. At this time, when another layer is laminated on the surface of the organic layer formed using the above coating composition, it is possible to prevent dissolution by a solvent, morphological influence, or decomposition.

[0258] Accordingly, when an organic layer formed using the above coating composition is formed including a heat treatment or phototreatment step, its resistance to solvents increases, allowing for the formation of multiple layers by repeatedly performing solution deposition and crosslinking methods, and increasing stability, thereby increasing the lifespan characteristics of the device.

[0259] The materials of the aforementioned anode, cathode, and specific organic layer are described in detail below.

[0260] As for the anode material, a material with a high work function is generally preferred to facilitate hole injection into the organic layer. Examples 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-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0261] The above cathode material is preferably a material with a small work function to facilitate electron injection into an organic layer. Examples include metals such as 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, but are not limited thereto.

[0262] The light-emitting layer may include a host material and / or a dopant material.

[0263] The above host materials include condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0264] According to one embodiment of the present invention, the host material may be used by mixing two or more host materials selected from the aforementioned host materials. For example, an anthracene derivative and a pyrene derivative may be mixed and used in a weight ratio of 1:99 to 99:1. As a more specific example, an anthracene derivative and a pyrene derivative may be mixed and used in a weight ratio of 92:8.

[0265] The above dopant materials include aromatic amine derivatives, styramine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and periplantene having arylamine groups. In addition, styramine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, wherein one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamine groups are substituted or unsubstituted. Specifically, styramine, styryldiamine, styryltriamine, styryltetraamine, etc. are examples, but are not limited thereto. In addition, metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0266] The hole injection layer described above is a layer that receives holes from an electrode. It is desirable for the hole injection material to have the ability to transport holes, thereby having an excellent hole receiving effect from the anode and an excellent hole injection effect on the emitting layer or emitting material. In addition, it is desirable for the material to have an excellent ability to prevent the movement of excitons generated in the emitting layer to the electron injection layer or electron injection material. In addition, it is desirable for the material to have an excellent thin film formation ability. Furthermore, it is desirable for the HOMO of the hole injection material to be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic materials; hexanitrile-hexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; and polythiophene-based conductive polymers such as anthraquinone and polyaniline. According to one embodiment of the present invention, the hole injection material is a compound of Formula 1; or a coating composition comprising a compound of Formula 1 or a cured product thereof.

[0267] The hole transport layer described above is a layer that receives holes from the hole injection layer and transports them to the emissive layer, and may have a single layer or a multilayer structure of two or more layers. As a hole transport material, a material capable of receiving holes from an anode or the hole injection layer and transferring them to the emissive layer is preferably a material with high mobility for holes. In the present invention, the compound of Formula 1 described above may be included as a hole transport material. In addition, other hole transport materials may be included in addition to the compound of Formula 1 as needed. Specific examples thereof include, but are not limited to, arylamine-based organic materials, carbazole-based compounds, conductive polymers, and block copolymers having both conjugated and non-conjugated portions. According to one embodiment of the present invention, the hole transport material is the compound of Formula 1; or a coating composition or a cured product thereof comprising the compound of Formula 1.

[0268] The electron transport layer described above is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. As for the electron transport material, it is a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, and a material with high electron mobility is preferred. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material as in the prior art. In particular, a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically, examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum layer or a silver layer.

[0269] The electron injection layer is a layer that receives electrons from an electrode. As for the electron injection material, it is desirable to have excellent electron transport ability and to have an electron receiving effect from the cathode, and an excellent electron injection effect on the emitting layer or emitting material. In addition, it is desirable to have a material that prevents excitons generated in the emitting layer from moving to the hole injection layer and has excellent thin film formation ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, etc., derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but are not limited thereto. The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, Bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc., are included but are not limited thereto.

[0270] The electron blocking layer is a layer capable of improving the lifespan or efficiency of a device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. The electron blocking layer may be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that performs hole injection and hole transport simultaneously, using the compound of Formula 2 described above. Additionally, other known electron blocking materials may be included in addition to the compound of Formula 2 as needed.

[0271] The hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, the hole blocking layer material includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc., but is not limited thereto.

[0272] The above hole injection and transport layers may include the materials of the hole injection layer and hole transport layer described above.

[0273] The above electron injection and transport layers may include the materials of the aforementioned electron injection layer and hole transport layer.

[0274] When the above organic light-emitting element includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0275] The organic light-emitting device according to the present invention may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0276] One embodiment of the present invention provides an electronic device comprising an organic light-emitting element comprising a compound of Formula 1; or a coating composition or a cured product thereof comprising the compound of Formula 1, or an organic layer formed using the coating composition.

[0277] The above electronic device may include, but is not limited to, all of the interlayer insulating film of a semiconductor device, a color filter, a black matrix, an overcoat, a column spacer, a passivation film, a buffer coat film, an insulating film for a multilayer printed circuit board, a cover coat of a flexible copper coating plate, a buffer coat film, an insulating film solder resist film for a multilayer printed circuit board, an insulating film of an OLED, a protective film of a thin-film transistor of a liquid crystal display device, an electrode protective film and a semiconductor protective film of an organic EL device, an insulating film of an OLED, an insulating film of an LCD, a insulating film of a semiconductor, a solar module, a touch panel, a display panel, etc.

[0278] Hereinafter, the present invention will be described in detail with reference to examples to specifically explain the invention. However, the embodiments according to the present invention may be modified in various different forms, and the scope of the present invention is not to be interpreted as being limited to the embodiments described below. The embodiments of the present invention are provided to more completely explain the invention to those with average knowledge in the art.

[0280] <Synthetic Example>

[0281] Synthesis Example 1. Synthesis of Compound 1

[0282]

[0283] 1) Synthesis of Intermediate 1-1

[0284]

[0285] 1-bromo-4-fluorophenoxybenzene was added to tetrahydrofuran (THF) (500 mL). After nitrogen substitution, magnesium was added to the reaction mixture, a small amount of iodine (I2) was added, and the mixture was stirred. Once the Grignard reagent was generated, 2-bromofluorenone was added at -78 °C, and the mixture was stirred overnight while slowly raising the temperature to room temperature. The reaction was terminated by adding distilled water, and the mixture was extracted with ethyl acetate and water. The organic layer was collected, dried using MgSO4, and filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent and used for the next reaction.

[0286] 2) Synthesis of Intermediate 1-2

[0287]

[0288] Intermediate 1-1 and 5 equivalents of phenol were placed in a round-bottom flask (RBF). CH3SO3H (0.7 M) was added, and the mixture was stirred at 60 °C for 4 hours. After adding ice water, the mixture was extracted with ethyl acetate and water. The organic layer was collected, dried using MgSO4, and filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, intermediate 1-2 was obtained by crystallization under dichloromethane / hexane conditions.

[0289] 3) Synthesis of Intermediates 1-3

[0290]

[0291] Intermediate 1-2,4-nitrobenaldehyde (1.5 equivalents), Cu(OAc)2 (5 mol%), and Cs2CO3 (1.5 equivalents) were placed in a round-bottom flask (RBF). Dimethylformamide (0.3 M) was added, and the mixture was stirred at 100 °C for 4 hours. The mixture was extracted with ethyl acetate and water, and the organic layer was collected. The organic layer was then dried using MgSO4 and filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, intermediate 1-3 was obtained by crystallization under dichloromethane / heptane [DCM / Heptane] conditions.

[0292] 4) Synthesis of intermediates 1-4

[0293]

[0294] CH3PPh3Br (2 equivalents), KOtBu (2 equivalents), and THF (0.2M) were placed in a round-bottom flask (RBF) and cooled to 0°C. A solution of intermediate 1-3 dissolved in tetrahydrofuran was added to the reaction mixture. The mixture was stirred for 1 hour while increasing the temperature to room temperature. The mixture was extracted with ethyl acetate and water, the organic layer was collected, dried using MgSO4, and then filtered.

[0295] The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, intermediates 1-4 were obtained by crystallization under dichloromethane / ethanol [DCM / EtOH] conditions.

[0296] 5) Synthesis of Compound 1

[0297]

[0298] N , N' -Bis(4-fluorophenyl)benzidine [ N , N' -Bis(4-fluorophenyl)benzidine] (2.5 mmol), intermediate 1-4 (5.13 mmol), Pd(PtBu3)2 (64 mg, 0.125 mmol), and NaOtBu (961 mg, 10 mmol) were added to a round-bottom flask (RBF). After nitrogen purging, 12.5 mL of toluene was added, and the mixture was stirred at 90 °C for 1 hour. The mixture was extracted with ethyl acetate and water, and the organic layer was collected. The organic layer was dried using MgSO4 and then filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, Compound 1 was obtained by crystallization under dichloromethane / ethanol [DCM / EtOH] conditions. The synthesis of the compound was confirmed by LC-MS. MS: [M+H] + = 1461.5

[0300] Synthesis Example 2. Synthesis of Compound 2

[0301]

[0302] 2,2'-Bis(4-fluorophenylamino-9,9'-spirobi[9H-fluorene]) [2,2'-Bis(4-fluorophenylamino)-9,9'-spirobi[9 HPd(PtBu3)2 (2.5 mmol), intermediate 1-4 (5.13 mmol), Pd(PtBu3)2 (64 mg, 0.125 mmol), and NaOtBu2 (961 mg, 10 mmol) were added to a round-bottom flask (RBF). After nitrogen purging, 12.5 mL of toluene was added, and the mixture was stirred at 90 °C for 1 hour. The mixture was extracted with ethyl acetate and water, and the organic layer was collected. The organic layer was dried using MgSO4 and then filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, 2.5 g of Compound 2 was obtained by crystallization under dichloromethane / ethanol [DCM / EtOH] conditions. The synthesis of the compound was confirmed by LC-MS. MS: [M+H] + = 1623.6

[0304] Sojaye

[0305] Experimental Example 1.

[0306] A glass substrate coated with an indium tin oxide (ITO) thin film to a thickness of 1,500 Å was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. products were used as the detergent, and distilled water that had been filtered twice using a Millipore Co. filter was used. After washing the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water washing was completed, the substrate was ultrasonically cleaned with an isopropyl and acetone solvent and dried. Subsequently, the substrate was cleaned for 5 minutes and then transported to a glove box.

[0307] A 2 wt% cyclohexanone ink containing Compound 1 prepared in Preparation Example 1 and Compound G below in a weight ratio of 8:2 was spin-coated onto the surface of an ITO transparent electrode and heat-treated at 220 °C for 30 minutes to form a hole injection layer with a thickness of 400 Å.

[0308] A hole transport layer with a thickness of 200 Å was formed by spin-coating a 2 wt% toluene ink of the following compound A onto the hole injection layer and heat-treating at 120 °C for 10 minutes. A emitting layer with a thickness of 200 Å was formed by vacuum-depositing the following compounds B and C in a weight ratio of 92:8 onto the hole transport layer. An electron transport and injection layer with a thickness of 350 Å was formed by vacuum-depositing the following compound D onto the emitting layer. A cathode was formed by sequentially depositing LiF with a thickness of 10 Å and aluminum with a thickness of 1000 Å onto the electron transport and injection layer.

[0309]

[0311] In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, while the deposition rates for the cathode lithium fluoride and aluminum were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 2 x 10⁻⁶ -7 ~ 5 x 10 -8 maintained torr.

[0313] 10 mA / cm of the organic light-emitting diode manufactured above 2 The results of measuring the driving voltage, current efficiency, and lifespan at the current density are shown in Table 1 below. T90 refers to the time (hr) required for the brightness to decrease to 90% from the initial brightness (500 nit).

[0315] Example 2 and Comparative Examples 1 to 2.

[0316] An organic light-emitting diode was prepared in the same manner as in Example 1, except that a compound listed in Table 1 below was used instead of Compound 1 as the host material when preparing the hole injection layer, and each organic light-emitting diode had a 10 mA / cm² 2 The results of measuring the driving voltage, current efficiency, and lifespan at the current density are shown in Table 1 below.

[0318] HIL host Driving voltage (V) Current efficiency (cd / A) T90 (hr) @500 nit Example 1 Compound 1 4.6 4.12 173 Example 2 Compound 2 4.55 4.23 168 Comparative Example 1 Comparative Compound 1 5.5 3.82 79 Comparative Example 2 Comparative Compound 2 5.4 3.77 85

[0320] Comparative Compound 1

[0321]

[0322] Comparative Compound 2

[0323]

[0325] Examples 1 and 2 used a compound represented by Formula 1 according to the present invention as the host of the hole injection layer, and Comparative Examples 1 and 2 used a compound not included in the range of Formula 1 of the present invention as the host of the hole injection layer.

[0326] As shown in Table 1 above, the compound represented by Formula 1 according to the present invention includes an ether group (specifically a vinylphenoxy group) and a haloaryloxy group (specifically a fluorophenoxy group) into which a curable group is introduced within the compound, and it can be confirmed that an organic light-emitting device using the present compound as a host for a hole injection layer has a significantly reduced driving voltage or a significantly improved current efficiency or lifespan compared to an organic light-emitting device of a comparative example and a curable group within the compound. Explanation of the symbols

[0328] 101: Board 201: First electrode 301: Hole injection layer 401: Precision Transport Layer 501: Emissive layer 601: Electron injection and transport layer 701: Second electrode

Claims

Claim 1 Compound represented by the following chemical formula 4: [Chemical Formula 4] In the above Chemical Formula 4, L is a substituted or unsubstituted divalent aromatic hydrocarbon ring; or a substituted or unsubstituted divalent heterocyclic ring; L1 and L2 are identical or different from each other and are each independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; Ar1 ​​and Ar2 are identical or different from each other and are each independently substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; X1 is a curable group; X3 is a curable group; R1 and R2 are identical or different from each other and are each independently hydrogen; deuterium; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or is a substituted or unsubstituted heteroaryl group, n1 and n2 are each integers from 0 to 7, and when n1 and n2 are each 2 or more, the substituents in the 2 or more parentheses are identical or different from each other, m1 is the number of bonding positions where a substituent can be attached to Ar1 from 0 to 7, m2 is the number of bonding positions where a substituent can be attached to Ar2 from 0 to 5, m3 is an integer from 1 to 5, and m4 is an integer from 1 to 5. Claim 2 delete Claim 3 delete Claim 4 delete Claim 5 A compound according to claim 1, wherein L is a divalent aromatic hydrocarbon ring group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms. Claim 6 delete Claim 7 A compound according to claim 1, wherein Ar1 and Ar2 are identical or different from each other and each is independently a phenyl group substituted or unsubstituted with an alkyl group; a biphenyl group; or a terphenyl group. Claim 8 A compound according to claim 1, wherein m1 and m2 are each integers from 0 to 13. Claim 9 A compound according to claim 1, wherein the curable group is selected from the group consisting of the following structures: In the above structures, --- refers to a position connected to the above chemical formula 4. Claim 10 A compound according to claim 1, wherein the compound represented by the chemical formula 4 is any one selected from the group consisting of the following compounds: . Claim 11 A coating composition comprising a compound according to any one of claims 1, 5 and 7 to 10. Claim 12 An organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the one or more organic layers comprise a coating composition according to claim 11 or a cured product thereof. Claim 13 An organic light-emitting device according to claim 12, wherein the one or more organic layers comprise one or more layers selected from the group consisting of a hole injection layer; a hole transport layer; and a hole injection and transport layer, and the one or more layers selected from the group consisting of a hole injection layer; a hole transport layer; and a hole injection and transport layer comprise the coating composition or a cured product thereof. Claim 14 A method for manufacturing an organic light-emitting device comprising: a step of preparing a first electrode; a step of forming one or more organic layers on the first electrode; and a step of forming a second electrode on the one or more organic layers, wherein the step of forming one or more organic layers includes a step of forming an organic layer using a coating composition according to claim 11. Claim 15 A method for manufacturing an organic light-emitting device according to claim 14, wherein the step of forming an organic layer using the coating composition comprises: a step of coating the coating composition; and a step of heat-treating or photo-treating the coated coating composition.

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