Compound, coating composition containing same, organic light-emitting device using same, and method for manufacturing same

Abstract

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

Description

[Technical Field]

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0057348, filed with the Korean Intellectual Property Office on May 10, 2022, the entire contents of which are incorporated herein by reference.

[0002] The present specification relates to a compound, a coating composition including the compound, an organic light-emitting device formed using the coating composition, and a method for manufacturing the same. [Background technology]

[0003] Organic light-emitting devices are an example of devices in which electric current is converted into visible light through internal processes within specific organic molecules. The principle of organic light-emitting devices 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 injected electrons and holes recombine to form excitons, which then fall back to the ground state and emit light. Organic light-emitting devices based on this principle typically consist of a cathode, an anode, and organic layers positioned between them, such as a hole injection layer, a hole transport layer, an emitting layer, an electron injection layer, and an electron transport layer.

[0004] Conventionally, a deposition process has been mainly used to manufacture organic light-emitting devices. However, manufacturing organic light-emitting devices using a deposition process has problems such as a large loss of materials and difficulty in manufacturing large-area devices. To solve these problems, devices using a solution process have been developed.

[0005] Therefore, there is a need for development of materials for solution processing. Summary of the Invention [Problem to be solved by the invention]

[0006] An object of the present invention is to provide a novel compound and an organic light-emitting device containing the compound. [Means for solving the problem]

[0007] One embodiment of the present invention provides a compound represented by the following Chemical Formula 1: [ka]

[0008] In the above Chemical Formula 1, Cy1 to Cy4 are the same or different and each independently represent a substituted or unsubstituted hydrocarbon ring group; Y1 and Y2 are the same or different and each independently represents O, S, Se, or NR; L is a substituted or unsubstituted divalent hydrocarbon ring group; or a substituted or unsubstituted divalent heterocyclic group; L1 to L4 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; L10 and L11 are the same or different and each independently represent a substituted or unsubstituted arylene group; X1 and X2 are the same or different and each independently represent a curable group; R and R1 to R4 are the same or different and each independently represent 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; n1 and n2 each represent an integer of 0 to 4, and when n1 and n2 each represent 2 or more, the two or more substituents in parentheses are the same or different from each other, m1 and m2 are each an integer of 1 to 5, n1+m1 is 5 or less, and n2+m2 is 5 or less; n3 and n4 are each an integer of 1 to 7, and when n3 and n4 are each 2 or more, the two or more substituents in parentheses are the same or different.

[0009] Another embodiment of the present invention provides a coating composition comprising the compound.

[0010] Another embodiment of the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the coating composition described above or a cured product thereof.

[0011] Another embodiment of the present invention provides a method for manufacturing an organic light-emitting device, comprising: preparing a first electrode; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layers, wherein the forming of the organic material layers comprises forming one or more organic material layers using the coating composition. [Effects of the Invention]

[0012] In one embodiment of the present invention, a compound has a heteroaryl group introduced near the N atom, which facilitates energy level control. Therefore, when applied to an organic layer, the interfacial properties with other layers are improved and hole mobility is facilitated. Furthermore, the compound has excellent hole mobility due to the inclusion of a fluoro group (-F) at a specific position.

[0013] In addition, the compound according to an embodiment of the present invention can be used as a material for an organic layer of an organic light-emitting device, and when applied to an organic light-emitting device, it can provide a device having low driving voltage, excellent luminous efficiency, and / or long life characteristics.

[0014] Furthermore, the compound according to one embodiment of the present invention has the advantage that it forms a completely hardened thin film by heat treatment or light treatment, thereby forming a stable thin film that is not damaged by the subsequent solution process.

[0015] Furthermore, the compound according to an embodiment of the present invention exhibits resistance to certain solvents after curing, allowing for solution processing during device fabrication, thereby enabling devices with larger area. [Brief explanation of the drawings]

[0016] [Figure 1] 1 is a diagram illustrating the structure of an organic light-emitting device according to an embodiment of the present invention; DETAILED DESCRIPTION OF THE INVENTION

[0017] The present invention will be described in detail below. One embodiment of the present invention provides a compound of Formula 1:

[0018] [ka]

[0019] In the above Chemical Formula 1, Cy1 to Cy4 are the same or different and each independently represent a substituted or unsubstituted hydrocarbon ring group; Y1 and Y2 are the same or different and each independently represents O, S, Se, or NR; L is a substituted or unsubstituted divalent hydrocarbon ring group; or a substituted or unsubstituted divalent heterocyclic group; L1 to L4 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; L10 and L11 are the same or different and each independently represent a substituted or unsubstituted arylene group; X1 and X2 are the same or different and each independently represent a curable group; R and R1 to R4 are the same or different and each independently represent 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; n1 and n2 each represent an integer of 0 to 4, and when n1 and n2 each represent 2 or more, the two or more substituents in parentheses are the same or different from each other, m1 and m2 are each an integer of 1 to 5, n1+m1 is 5 or less, and n2+m2 is 5 or less; n3 and n4 are each an integer of 1 to 7, and when n3 and n4 are each 2 or more, the two or more substituents in parentheses are the same or different.

[0020] The compound of Formula 1 has high stability and a high HOMO (highest occupied molecular orbital) energy level because the fluorenyl group contains at least one fluoro group (-F).

[0021] Furthermore, the compound has a high HOMO (highest occupied molecular orbital) energy level due to the introduction of a heteroaryl group near the N atom.

[0022] Therefore, when the compound is incorporated into a hole injection layer or a hole transport layer in an organic light emitting device, the interfacial properties with the adjacent layer are improved, and hole migration is facilitated. In particular, when the compound of Formula 1 is incorporated into a hole injection layer in an organic light emitting device, it facilitates hole injection from the hole injection layer to the hole transport layer, which has a significant impact on improving the life of the device.

[0023] Furthermore, the compound has excellent solubility, which allows for the selection of various solvents when preparing a coating composition.

[0024] Furthermore, the compound has the advantage that it forms a completely hardened thin film after heat or light treatment, thereby forming a stable thin film that is not damaged by the subsequent solution process.

[0025] Furthermore, the compound exhibits resistance to certain solvents after curing, allowing for solution processing during device fabrication, thereby enabling devices with larger area.

[0026] As used herein, the term "energy level" refers to the magnitude of energy. Therefore, the energy level is interpreted as meaning the absolute value of the energy value. For example, a deep energy level means that the absolute value increases in the negative direction from the vacuum level.

[0027] In this specification, when a member (layer) is said to be "on" another member (layer), this includes not only the case where a member (layer) is in contact with the other member, but also the case where another member (layer) exists between the two members (layers).

[0028] In this specification, when a part is said to "comprise" a certain component, this does not mean that it excludes other components, but that it may further include other components, unless otherwise specified.

[0029] The substituents used in this specification will be described in detail below.

[0030] As used herein, the term "curable group" refers to a reactive substituent that crosslinks compounds upon exposure to heat and / or light. The crosslinking can be achieved by linking radicals generated by decomposition of carbon-carbon multiple bonds or cyclic structures upon heat treatment or light irradiation.

[0031] As used herein, "C x1-x2 " means "number of carbon atoms x1 to x2".

[0032] In this specification, [ka] denotes a site of attachment to another substituent or bond.

[0033] As used herein, the term "adjacent" groups may refer to a substituent substituted on an atom directly linked to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring can be interpreted as groups "adjacent" to each other.

[0034] As used herein, in the ring formed by bonding adjacent groups together, the term "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle.

[0035] As used herein, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different.

[0036] As used herein, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amine, aryl, and heteroaryl groups, or substituted with a substituent in which two or more of the above-listed substituents are linked, or no substituents are present. For example, a "substituent in which two or more substituents are linked" may be a biphenyl group. That is, a biphenyl group may be an aryl group and can be interpreted as a substituent in which two phenyl groups are linked.

[0037] Examples of the substituents are described below, but are not limited to these.

[0038] As used herein, examples of halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0039] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but preferably is 1 to 60. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 30. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0040] In this specification, the term "alkylene group" refers to an alkyl group having two bonding positions, i.e., a divalent group. The same explanation as for the alkyl group above may be applied, except that these are divalent groups.

[0041] In this specification, the number of carbon atoms in the cycloalkyl group is not particularly limited, but is preferably 3 to 60. According to one embodiment, the number of carbon atoms in the cycloalkyl group is 3 to 30. Specific examples of the cycloalkyl group include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0042] In this specification, the alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably 1 to 30. Specific examples of the alkoxy group include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, and n-decyloxy.

[0043] In this specification, the aryl group is not particularly limited, but may have 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. Examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, and a terphenyl group. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenylenyl group, a chrysenyl group, and a fluorenyl group.

[0044] As used herein, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

[0045] When the fluorenyl group is substituted, [ka] The exemplified structures may be substituted with additional substituents, but the structures are not limited to these.

[0046] In this specification, the heterocyclic group is an aromatic, aliphatic, or aromatic-aliphatic fused ring group containing one or more heteroatoms selected from N, O, P, and S. The number of carbon atoms in the heterocyclic group is not particularly limited, and may be 2 to 60 carbon atoms.

[0047] In this specification, a heteroaryl group is an aromatic ring group containing one or more heteroatoms selected from N, O, P, and S, and the number of carbon atoms is not particularly limited, but may be 2 to 60. According to one embodiment, the number of carbon atoms in the heteroaryl group is 2 to 30. Examples of the heteroaryl group include, but are not limited to, a pyridine group, a pyrrole group, a pyrimidine group, a pyridazine group, a furan group, a thiophene group, a benzothiophene group, a benzofuran group, a dibenzothiophene group, a dibenzofuran group, and a carbazole group.

[0048] In this specification, the hydrocarbon ring group may be an aromatic ring, an aliphatic ring, or a ring in which an aromatic ring and an aliphatic ring are fused together.

[0049] In this specification, the aromatic ring may be the same as the above description of the aryl group.

[0050] In this specification, the above description of the cycloalkyl group may be applied to the aliphatic ring.

[0051] In this specification, the term "arylene group" refers to an aryl group having two bonding positions, i.e., a divalent group. The same explanation of the aryl group as described above may be applied, except that these are divalent groups.

[0052] In this specification, the term "heteroarylene group" refers to a heteroaryl group having two bonding positions, i.e., a divalent group. The same explanation of the heteroaryl group as described above may be applied, except that these are divalent groups.

[0053] In one embodiment of the present specification, in the above Chemical Formula 1, F means fluorine.

[0054] In one embodiment of the present specification, X1 and X2 are the same or different and each independently represents a curable group.

[0055] In one embodiment of the present specification, the curable group has any one of the following structures:

[0056] [ka]

[0057] In the above structure: L51 to L56 are the same or different and each independently represent a group formed by linking one or more selected from the group consisting of a direct bond; —O—; a substituted or unsubstituted alkylene group; and a substituted or unsubstituted arylene group; [ka] is the site of attachment to Chemical Formula 1.

[0058] In one embodiment of the present invention, X1 and X2 are the same or different and each independently represent one of the following structures:

[0059] [ka] In the above structure: [ka] and L53 to L55 are as described above.

[0060] In one embodiment of the present invention, X1 and X2 are the same or different and each independently represent one of the following structures: [ka]

[0061] In one embodiment of the present invention, the above-mentioned Chemical Formula 1 is the following Chemical Formula 2: [ka]

[0062] In the above Chemical Formula 2, The definitions of Cy1 to Cy4, Y1, Y2, L, L1 to L4, L10, L11, X1, X2, R1 to R4, n1 to n4, m1, and m2 are as in Chemical Formula 1.

[0063] In one embodiment of the present invention, L10 and L11 are the same or different and each independently represent a substituted or unsubstituted C 6-60 is an arylene group of the formula: In one embodiment of the present invention, L10 and L11 are the same or different and each independently represent a substituted or unsubstituted C 6-30 is an arylene group of the formula: In one embodiment of the present invention, L10 and L11 are the same or different and each independently represent a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group. In one embodiment of the present invention, L10 and L11 are the same or different and each independently represent a substituted or unsubstituted phenylene group.

[0064] In one embodiment of the present invention, the above-mentioned Chemical Formula 1 is the following Chemical Formula 2-1.

[0065] [ka]

[0066] In the above Chemical Formula 2-1, Cy1 to Cy4, Y1, Y2, L, L1 to L4, X1, X2, R1 to R4, n1 to n4, m1, and m2 are defined as in Chemical Formula 1. R5 and R6 are the same or different and each independently represent 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; n5 and n6 each represent an integer of 0 to 4, and when n5 and n6 each represent 2 or more, the two or more substituents in parentheses are the same or different.

[0067] In one embodiment of the present invention, R5 and R6 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted C 1-20 alkyl group; substituted or unsubstituted C 1-20 alkoxy groups of the formula; substituted or unsubstituted C 6-30 or a substituted or unsubstituted C 2-30 is a heteroaryl group of the formula: In one embodiment of the present invention, R5 and R6 are the same or different and each independently represent hydrogen; deuterium; a halogen group; 1-20 Alkyl group of C 1-20 Alkoxy group; C 6-30 an aryl group of C; or C 2-30 is a heteroaryl group of the formula: In one embodiment of the present invention, R5 and R6 are each hydrogen or deuterium.

[0068] In one embodiment of the present invention, Cy1 to Cy4 are the same or different and each independently represent a substituted or unsubstituted aromatic ring. In one embodiment of the present invention, Cy1 to Cy4 are the same or different and each independently represents an aromatic ring. In one embodiment of the present invention, Cy1 to Cy4 are the same or different and each independently represent a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring. In one embodiment of the present invention, each of Cy1 to Cy4 is a benzene ring.

[0069] In one embodiment of the present invention, the above-mentioned Chemical Formula 1 is the following Chemical Formula 3:

[0070] [ka]

[0071] In the above Chemical Formula 3, The definitions of Y1, Y2, L, L1 to L4, L10, L11, X1, X2, R1 to R4, n1 to n4, m1, and m2 are as in Chemical Formula 1. R50 and R51 are the same or different and each independently represent 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, or are bonded to adjacent groups to form a substituted or unsubstituted ring; n50 and n51 each represent an integer of 1 to 7, and when n50 and n51 each represent 2 or more, the two or more substituents in parentheses are the same or different.

[0072] In one embodiment of the present invention, the formula 3 is the following formula 3-1 or 3-2.

[0073] [ka]

[0074] [ka]

[0075] In the above chemical formulas 3-1 and 3-2, The definitions of Y1, Y2, L, L1 to L4, L10, L11, X1, X2, R1 to R4, n1 to n4, m1, and m2 are as in Chemical Formula 1. R60 to R63 are the same or different and each independently represent 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; n60 and n61 are each an integer of 1 to 7, n62 and n63 are each an integer of 1 to 9, and when n60 to n63 are each 2 or more, the substituents in the two or more parentheses are the same or different.

[0076] In one embodiment of the present invention, the above-mentioned Chemical Formula 3 is any one of the following Chemical Formulas 3-11 to 3-18.

[0077] [ka]

[0078] [ka]

[0079] [ka]

[0080] [ka]

[0081] [ka]

[0082] [ka]

[0083] [ka]

[0084] [ka]

[0085] In the chemical formulas 3-11 to 3-18, The definitions of Y1, Y2, L, L1 to L4, L10, L11, X1, X2, R1 to R4, n1 to n4, m1, and m2 are as in Chemical Formula 1. R60 to R63 are the same or different and each independently represent 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; n60 and n61 are each an integer of 1 to 7, n62 and n63 are each an integer of 1 to 9, and when n60 to n63 are each 2 or more, the substituents in the two or more parentheses are the same or different.

[0086] In one embodiment of the present invention, R60 to R63 are each hydrogen or deuterium.

[0087] In one embodiment of the present invention, the L is substituted or unsubstituted C 6-60 a divalent hydrocarbon ring group; or a substituted or unsubstituted C 2-60 is a divalent heterocyclic group of the formula: In one embodiment of the present invention, the L is substituted or unsubstituted C 6-30 a divalent hydrocarbon ring group; or a substituted or unsubstituted C 2-30 is a divalent heterocyclic group of the formula: According to another embodiment, the L is substituted or unsubstituted C 6-30 is a divalent hydrocarbon ring group. In one embodiment of the present invention, L is a divalent hydrocarbon ring group substituted or unsubstituted with an alkyl group or an aryl group. In one embodiment of the present invention, L is any one of the following structures:

[0088] [ka]

[0089] In the above structure: R10 to R31 are the same or different and each independently represent 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; n10 to n21 each represent an integer of 1 to 4, n22, n23, n28, and n29 each represent an integer of 1 to 3, n24 and n25 each represent an integer of 1 to 7, n26 is an integer of 1 to 8, and n27 is an integer of 1 to 6; when n10 to n29 each represent 2 or more, the two or more substituents in parentheses are the same or different from each other; [ka] is the site of attachment to Chemical Formula 1.

[0090] In one embodiment of the present invention, R10 to R29 are the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group. In one embodiment of the present invention, R10 to R29 are the same or different and each independently represent hydrogen; deuterium; or substituted or unsubstituted C 1-20 is an alkyl group. In one embodiment of the present invention, R10 to R29 are the same or different and each independently represent hydrogen; deuterium; or C 1-20 is an alkyl group.

[0091] In one embodiment of the present invention, R30 and R31 are the same or different and each independently represent a substituted or unsubstituted alkyl group. In one embodiment of the present invention, R30 and R31 are the same or different and each independently represent a substituted or unsubstituted C 1-20 is an alkyl group. In one embodiment of the present invention, R30 and R31 are the same or different and each independently represent C 1-20 is an alkyl group.

[0092] In one embodiment of the present invention, L1 to L4 are the same or different from each other and each independently represent a direct bond; a substituted or unsubstituted C 6-60 an arylene group of the formula: 2-60 is a heteroarylene group of the formula: In one embodiment of the present invention, L1 to L4 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted C 6-30 is an arylene group of the formula: In one embodiment of the present invention, the L1 to L4 are the same or different and each independently represent a direct bond; or a C 6-30 is an arylene group of the formula: In one embodiment of the present invention, L1 to L4 are the same or different and each independently represent a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group. In one embodiment of the present invention, L1 to L4 are the same or different and each independently represent a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group. In one embodiment of the present invention, L1 to L4 are the same or different and each independently represent a direct bond; a phenylene group unsubstituted or substituted with deuterium, a halogen group, or an alkyl group; or a biphenylene group unsubstituted or substituted with deuterium, a halogen group, or an alkyl group. In one embodiment of the present invention, L1 to L4 are the same or different and each independently represent a direct bond; deuterium, F, or C. 1-20 a phenylene group substituted or unsubstituted with an alkyl group of the formula: 1-20 and a biphenylene group substituted or unsubstituted with an alkyl group of the formula:

[0093] In one embodiment of the present invention, R1 to R4 are the same or different and each independently represent hydrogen; deuterium; a halogen group; or a substituted or unsubstituted C 1-20alkyl group; substituted or unsubstituted C 1-20 alkoxy groups of the formula; substituted or unsubstituted C 6-30 or a substituted or unsubstituted C 2-30 is a heteroaryl group of the formula: In one embodiment of the present invention, R1 to R4 are the same or different and each independently represent hydrogen; deuterium; or substituted or unsubstituted C 1-30 is an alkyl group. In one embodiment of the present invention, R1 to R4 are the same or different and each independently represent hydrogen; deuterium; or an alkyl group.

[0094] In one embodiment of the present invention, Y1 and Y2 are the same or different and each independently represents O or S.

[0095] In one embodiment of the present invention, m1 and m2 each represent an integer of 1 to 5. In one embodiment of the present invention, m1 is 1. In one embodiment of the present invention, m1 is 2. In one embodiment of the present invention, m1 is 3. In one embodiment of the present invention, m1 is 4. In one embodiment of the present invention, m1 is 5. In one embodiment of the present invention, m2 is 1. In one embodiment of the present invention, m2 is 2. In one embodiment of the present invention, m2 is 3. In one embodiment of the present invention, m2 is 4. In one embodiment of the present invention, m2 is 5.

[0096] In one embodiment of the present invention, the compound of Formula 1 has any one of the following structures:

[0097] [ka]

[0098] [ka]

[0099] [ka]

[0100] [ka]

[0101] [ka]

[0102] [ka]

[0103] In one embodiment of the present invention, the core structure of the compound of Formula 1 can be prepared as shown in the following reaction scheme: In this case, substituents may be attached by methods well known in the art, and the type, position, or number of substituents may be changed by techniques well known in the art.

[0104] <Reaction formula> [ka]

[0105] In the reaction formula, Cy1 to Cy4, Y1, Y2, L, L1 to L4, L10, L11, X1, X2, R1 to R4, n1 to n4, m1, and m2 are defined as in Chemical Formula 1.

[0106] One embodiment of the present invention provides a coating composition comprising a compound of Formula 1 above.

[0107] In one embodiment of the present invention, the coating composition further comprises a solvent. In one embodiment of the present invention, the coating composition comprises the compound of Chemical Formula 1 and a solvent.

[0108] In one embodiment of the present invention, the coating composition may be in a liquid state. The term "liquid" means that the coating composition is in a liquid state at room temperature and normal pressure.

[0109] In one embodiment of the present invention, when the coating composition is applied to an organic layer, a solvent that does not dissolve the material of the underlying layer is used, which has the advantage that the organic layer can be applied by solution processing.

[0110] In one embodiment of the present invention, the compound contains a curable group, which improves the resistance to solvents during heat treatment after coating, i.e., the compound is insoluble in certain solvents due to crosslinking after coating.

[0111] For example, if a coating composition is prepared using a solvent that dissolves the compound and a layer is prepared by a solution process, the layer can be resistant to the same solvent when cured by heat treatment.

[0112] Therefore, if an organic material layer is formed using the coating composition and then cured, a solution process is possible when applying another organic material layer.

[0113] In one embodiment of the present invention, the curing process may be photocuring or thermal curing. For example, after forming an organic layer using the coating composition, the coating composition is cured by a heat treatment or a light treatment process, so that an upper layer can be applied by a solution process.

[0114] For example, when the coating composition is applied to a hole injection layer, it is advantageous to use a particular solvent to which the cured coating composition is resistant in fabricating an overlying layer (such as a hole transport layer), thereby enabling the overlying layer to be applied by solution processing.

[0115] In one embodiment of the present invention, the solvent contained in the coating composition is a solvent that dissolves the compound. Examples of the solvent include chlorine-based solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether-based solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon-based solvents such as toluene, xylene, trimethylbenzene, and mesitylene; ketone-based solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester-based solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, and propylene glycol. Examples of solvents include polyhydric alcohols and derivatives thereof such as glycerol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol; alcohol-based solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide-based solvents such as dimethyl sulfoxide; amide-based solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate-based solvents such as methyl benzoate, butyl benzoate, and 3-phenoxybenzoate; and tetralin, but are not limited to these as long as they are capable of dissolving or dispersing a compound according to one embodiment of the present invention.

[0116] In one embodiment of the present invention, the solvent may be used alone or in combination of two or more kinds.

[0117] In one embodiment of the invention, the coating composition does not further comprise a p-doping material.

[0118] In one embodiment of the present invention, the coating composition further comprises a p-dopant.

[0119] In this specification, the p-doping material refers to a material that causes a host material to have p-semiconductor properties, which means the property of receiving or transporting holes at the highest occupied molecular orbital (HOMO) energy level, i.e., the property of a material having high hole conductivity.

[0120] The p-doping material may have any one of the following structures, but is not limited thereto:

[0121] [ka]

[0122] In the present invention, the p-doping material may be any material that can provide p-semiconductor characteristics, and one or more types may be used, with no particular limitation on the type.

[0123] In one embodiment of the present invention, the content of the p-doping material is 0 wt % to 500 wt % based on the compound of Formula 1. Specifically, the content of the p-doping material is 100 wt % to 400 wt % based on the compound of Formula 1.

[0124] In one embodiment of the present invention, the p-doping material is contained in an amount of 0 to 50 wt % based on the total solid content of the coating composition, preferably 1 to 50 wt % based on the total solid content of the coating composition, and more preferably 10 to 30 wt % based on the total solid content of the coating composition.

[0125] In other embodiments, the coating composition further comprises a monomer containing a functional group that is crosslinkable by heat or light; or a monomer containing a terminal group that is capable of forming a polymer by heat.

[0126] In one embodiment of the present invention, the monomolecule containing a functional group that can be crosslinked by heat or light; or the monomolecule containing a terminal group that can form a polymer by heat, may be a compound having a molecular weight of 3,000 g / mol or less.

[0127] In one embodiment of the present invention, the monomer containing a functional group crosslinkable by heat or light; or the monomer containing an end group capable of forming a polymer by heat may be an aryl such as phenyl, biphenyl, fluorene, or naphthalene; an arylamine; or a monomer in which a functional group crosslinkable by heat or light or an end group capable of forming a polymer by heat is substituted on fluorene.

[0128] In one embodiment of the present invention, the viscosity of the coating composition at room temperature is 2 cP to 15 cP. Specifically, the viscosity of the coating composition is 2 cP to 10 cP. When the above viscosity is satisfied, it is easy to manufacture a device.

[0129] One embodiment of the present invention provides an organic light-emitting device formed using the coating composition.

[0130] One embodiment of the present invention provides an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the coating composition or a cured product thereof. In this case, the cured product of the coating composition is in a state where the coating composition is cured by a heat treatment or a light treatment.

[0131] In one embodiment of the present invention, the organic layer containing the coating composition or a cured product thereof is a hole transport layer, a hole injection layer, or a layer that simultaneously transports and injects holes.

[0132] In one embodiment of the present invention, the organic layer containing the coating composition or a cured product thereof is an electron transport layer, an electron injection layer, or a layer that simultaneously transports and injects electrons.

[0133] In one embodiment of the present invention, the organic layer containing the coating composition or a cured product thereof is a light-emitting layer.

[0134] In one embodiment of the present invention, the organic layer containing the coating composition or a cured product thereof is a light-emitting layer, and the light-emitting layer contains the compound of the present invention as a host of the light-emitting layer.

[0135] In one embodiment of the present invention, the organic layer containing the coating composition or a cured product thereof is a light-emitting layer, and the light-emitting layer contains the compound of the present invention as a dopant for the light-emitting layer.

[0136] In one embodiment of the present invention, the organic light-emitting device includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, a layer that simultaneously injects holes and transports holes, and a layer that simultaneously injects electrons and transports electrons.

[0137] In one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.

[0138] According to one embodiment, the first electrode is a cathode and the second electrode is an anode.

[0139] In another embodiment, the organic light-emitting device may be a normal type organic light-emitting device having a structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0140] In another embodiment, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0141] The organic material layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including two or more organic material layers selected from the group consisting of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously injects holes and transports holes, and a layer that simultaneously injects electrons and transports electrons. However, the structure of the organic light-emitting device is not limited thereto, and the device may include a smaller number of organic material layers.

[0142] For example, the structure of an organic light-emitting device according to one embodiment of the present invention is illustrated in FIG.

[0143] FIG. 1 illustrates the structure of an organic light-emitting element in which a first electrode 201, a hole injection layer 301, a hole transport layer 401, an emitting layer 501, an electron transport and injection layer 601, and a second electrode 701 are sequentially stacked on a substrate 101.

[0144] FIG. 1 illustrates an example of an organic light-emitting device, but the structure of the organic light-emitting device of the present invention is not limited to this.

[0145] When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0146] The organic light-emitting device of the present invention may be laminated in the following exemplary structure. (1) Anode / hole transport layer / light-emitting layer / cathode (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode (7) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode (10) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode (11) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode (14) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode (15) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode (17) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode (18) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Emitting Layer / Hole Blocking Layer / Electron Injection and Transport Layer / Cathode

[0147] In the above structure, the "electron transport layer / electron injection layer" may be substituted with "electron transport and injection layer" or "layer that simultaneously transports and injects electrons."

[0148] Also, in the above structure, the "hole injection layer / hole transport layer" may be replaced with a "hole injection and transport layer" or a "layer that simultaneously transports and injects holes."

[0149] The organic light-emitting device of the present invention may be manufactured using materials and methods well known in the art, except that at least one of the organic layers is formed using a coating composition containing the compound of Formula 1.

[0150] For example, the organic light-emitting device of the present invention can be fabricated by sequentially stacking an anode, organic material layer, and cathode on a substrate. In this case, a metal, conductive metal oxide, or alloy thereof is deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form an anode. Organic material layers, including a hole injection layer, a hole transport layer, an emitting layer, and a layer that simultaneously transports and injects electrons, are then formed on the anode using a solution process or evaporation process, and a material usable as a cathode is then deposited on the anode. In addition to this method, an organic light-emitting device can also be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0151] The present invention also provides a method for manufacturing an organic light emitting device formed using the coating composition.

[0152] Specifically, one embodiment of the present invention includes the steps of: preparing a first electrode; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layers, wherein the step of forming the organic material layers includes forming one or more organic material layers using the coating composition.

[0153] In one embodiment of the present invention, the step of forming one or more organic layers using the coating composition is performed using a spin coating method.

[0154] In another embodiment, the step of forming one or more organic layers using the coating composition utilizes a printing method.

[0155] In one embodiment of the present invention, the printing method includes, but is not limited to, inkjet printing, nozzle printing, offset printing, transfer printing, screen printing, and the like.

[0156] The coating composition according to one embodiment of the present invention has structural properties that make it suitable for solution processing and can be formed by a printing method, which is advantageous in that it is time- and cost-effective when manufacturing devices.

[0157] In one embodiment of the present invention, the step of forming one or more organic layers using the coating composition includes the steps of coating the coating composition on the first electrode; and subjecting the coated coating composition to a heat treatment or a light treatment.

[0158] In one embodiment of the present invention, the heat treatment may be performed by heat treatment. The heat treatment temperature in the heat treatment is 85°C to 250°C. Specifically, it may be 100°C to 250°C, and more specifically, it may be 150°C to 250°C.

[0159] In one embodiment of the present invention, the heat treatment time in the heat treatment step is 1 minute to 2 hours, and according to another embodiment, it may be 1 minute to 1 hour, and according to another embodiment, it may be 30 minutes to 1 hour.

[0160] In one embodiment of the present invention, the light treatment step may be performed by UV irradiation, and the light treatment step may be performed for 30 minutes to 5 hours.

[0161] In one embodiment of the present invention, the step of coating the coating composition on the first electrode includes a step of coating the coating composition on the first electrode and a step of coating the coating composition on another organic layer provided on the first electrode.

[0162] In one embodiment of the present invention, the other organic layer means an organic layer formed from another material, without including a coating composition or a cured product thereof.

[0163] When coating the coating composition on the first electrode, a solvent that does not dissolve the material of the underlying layer is used. For example, when the coating composition is applied to a hole transport layer, the coating composition contains a solvent that does not dissolve the material of the underlying layer (first electrode, hole injection layer, etc.).

[0164] By subjecting the coated coating composition to a heat treatment or light treatment, the compounds contained in the coating composition can be crosslinked to provide an organic material layer having a thin film structure. In this case, when another layer is laminated on the surface of the organic material layer formed using the coating composition, the organic material layer can be prevented from being dissolved, morphologically affected, or decomposed by a solvent.

[0165] Therefore, when an organic layer formed using the coating composition is subjected to a heat treatment or light treatment step, the resistance to solvents is increased, and multiple layers can be formed by repeatedly performing solution deposition and crosslinking methods, which increases stability and improves the lifespan of the device.

[0166] In one embodiment of the present invention, the anode material is preferably a material with a high work function to facilitate hole injection into the organic layer. Specific examples of the anode material include, but are not limited to, 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 SnO:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0167] In one embodiment of the present invention, the cathode material is preferably a material with a low work function so as to facilitate electron injection into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as barium, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO / Al.

[0168] In one embodiment of the present invention, the hole injection layer is a layer that injects holes from the electrode. The hole injection material preferably has hole transport capability, excellent hole injection effect at the anode, excellent hole injection effect in the light-emitting layer or light-emitting material, prevents excitons generated from the light-emitting layer from migrating to the electron injection layer or electron injection material, and excellent thin-film formation ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably 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, the compound of Formula 1, metal porphyrin, oligothiophene, arylamine-based organic compounds, hexanitrile hexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinone, and polyaniline and polythiophene-based conductive polymers.

[0169] In one embodiment of the present invention, the hole injection layer comprises the compound of the present invention described above. Also, in another embodiment of the present invention, the hole injection layer further comprises a p-doping material. The p-doping material contained in the hole injection layer is the same as that described above in the coating composition.

[0170] In one embodiment of the present invention, the hole transport layer receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and is preferably a material with high hole mobility. Specific examples of hole transport materials include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions. More specifically, the hole transport layer may be formed using a compound containing an arylamine group.

[0171] In one embodiment of the present invention, the hole transport layer comprises a compound of the following formula HT-1:

[0172] [ka]

[0173] In the formula HT-1, L201 is a substituted or unsubstituted arylene group; R201 to R204 are the same or different and each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0174] In one embodiment of the present invention, L201 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms. In one embodiment of the present invention, L201 is an arylene group. In one embodiment of the present invention, L201 is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group. In one embodiment of the present invention, L201 is a phenylene group; a biphenylene group; or a naphthylene group. In one embodiment of the present invention, L201 is a biphenylene group.

[0175] In one embodiment of the present invention, R201 to R204 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms. In one embodiment of the present invention, R201 to R204 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. In one embodiment of the present invention, R201 to R204 are the same or different and each independently represents an aryl group. In one embodiment of the present invention, R201 to R204 are the same or different and each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group. In one embodiment of the present invention, R201 to R204 are the same or different and each independently represent a phenyl group; a biphenyl group; or a naphthyl group.

[0176] In one embodiment of the present invention, the formula HT-1 has the following structure:

[0177] [ka]

[0178] In one embodiment of the present invention, the light-emitting material contained in the light-emitting layer is a material that can emit light in the visible light range by receiving and combining holes and electrons transported from the hole-transport layer and electron-transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include, but are not limited to, 8-hydroxyquinoline aluminum complex (Alq3), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzothiazole, and benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, and rubrene.

[0179] In one embodiment of the present invention, the light-emitting layer may include a host and a dopant. The host may be a fused aromatic ring derivative or a heterocycle-containing compound. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Specific examples of the heterocycle-containing compound include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives. More specifically, the host may be an anthracene derivative.

[0180] In one embodiment of the present invention, the host of the emitting layer comprises a compound of the following chemical formula EH-1:

[0181] [ka]

[0182] In the above chemical formula EH-1, L301 and L302 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heterocyclic group; Ar301 and Ar302 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; R301 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; r301 is an integer of 1 to 8, and when r301 is 2 or more, the two or more R301's may be the same or different from each other.

[0183] In one embodiment of the present invention, L301 and L302 are the same or different and each independently represent a direct bond; a substituted or unsubstituted monocyclic arylene group; or a substituted or unsubstituted polycyclic arylene group. In one embodiment of the present invention, L301 and L302 are the same or different and each independently represent a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group. In one embodiment of the present invention, said L301 and L302 are each a direct bond.

[0184] In one embodiment of the present invention, Ar301 and Ar302 are the same or different and each independently represent a substituted or unsubstituted aryl group. In one embodiment of the present invention, Ar301 and Ar302 are the same or different and each independently represent a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group. In one embodiment of the present invention, Ar301 and Ar302 are the same or different and each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted pyrene group; or a substituted or unsubstituted fluorenyl group. In one embodiment of the present invention, Ar301 and Ar302 are the same or different and each independently represent a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group. In one embodiment of the present invention, Ar301 and Ar302 are each a naphthyl group.

[0185] In one embodiment of the present invention, R301 is hydrogen; or deuterium.

[0186] In one embodiment of the present invention, the chemical formula EH-1 has any one of the following structures:

[0187] [ka]

[0188] In one embodiment of the present invention, the dopant may be an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, or the like. Specifically, the aromatic amine derivative may be a fused aromatic ring derivative having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, or periflanthene, which has an arylamino group. The styrylamine compound may be a substituted or unsubstituted arylamine compound having at least one arylvinyl group substituted thereon, which may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group. Specific examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. Furthermore, examples of metal complexes include, but are not limited to, iridium complexes and platinum complexes. More specifically, the dopant may be a compound containing an arylamine group.

[0189] In one embodiment of the present invention, the dopant of the light-emitting layer comprises a compound of the following formula ED-1:

[0190] [ka]

[0191] In the above chemical formula ED-1, Ar501 to Ar504 are the same or different and each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0192] In one embodiment of the present invention, the formula ED-1 is the following formula ED-2:

[0193] [ka]

[0194] In the formula ED-2, Ar501 to Ar504 are defined as in the above chemical formula ED-1.

[0195] In one embodiment of the present invention, Ar501 to Ar504 are the same or different and each independently represents a substituted or unsubstituted aryl group. In one embodiment of the present invention, Ar501 to Ar504 are the same or different and each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; or a substituted or unsubstituted naphthyl group. In one embodiment of the present invention, Ar501 to Ar504 are the same or different and each independently represent a phenyl group substituted or unsubstituted with a silyl group; a biphenyl group substituted or unsubstituted with a silyl group; a terphenyl group substituted or unsubstituted with a silyl group; or a naphthyl group substituted or unsubstituted with a silyl group. In one embodiment of the present invention, Ar501 to Ar504 are the same or different and each independently represent a phenyl group unsubstituted or substituted with a silyl group.

[0196] In the present invention, the silyl group is a group represented by -SiRcRd, where Rc and Rd may be the same or different and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. The number of carbon atoms in the silyl group is not particularly limited, but is preferably 1 to 60.

[0197] In one embodiment of the present invention, the formula ED-1 has the following structure:

[0198] [ka]

[0199] In one embodiment of the present invention, the electron transport layer receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material that can smoothly receive electrons injected from the cathode and transfer them to the light-emitting layer, and is preferably a material with high electron mobility. Specific examples include, but are not limited to, 8-hydroxyquinoline aluminum complexes; complexes containing Alq; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer may be used with any desired cathode material, as used in the prior art. Particularly suitable cathode materials are conventional materials with low work functions followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0200] In one embodiment of the present invention, the electron injection layer is a layer that injects electrons from the electrode, and the electron injection substance is preferably a compound that has the ability to transport electrons, has an excellent electron injection effect from the cathode, has an excellent electron injection effect on the light-emitting layer or light-emitting material, prevents excitons generated from the light-emitting layer from migrating to the hole injection layer, and has excellent thin-film forming ability. Specific examples of the electron injection substance include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, benzimidazole, perylene tetracarboxylic acid, phenanthroline, fluorenylidenemethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0201] In one embodiment of the present invention, examples of the metal complex compound include, but are not limited to, 8-hydroxyquinolinatolithium, 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-cresolate)gallium, bis(2-methyl-8-quinolinato)(1-naphtholate)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtholate)gallium.

[0202] In one embodiment of the present invention, the electron transport layer and the electron injection layer may be formed as layers that simultaneously transport and inject electrons, and may be referred to as electron transport and injection layers. In this case, materials used in the electron transport and injection layers may be any of the electron transport materials and electron injection materials described above. For example, the electron transport and injection layers may include a benzimidazole-based compound.

[0203] In one embodiment of the invention, the electron transporting and injecting layer comprises a compound of formula ET-1:

[0204] [ka]

[0205] In the formula ET-1, L601 and L602 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heterocyclic group; Ar601 and Ar602 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; R601 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0206] In one embodiment of the present invention, L601 and L602 are the same or different and each independently represent a direct bond; a substituted or unsubstituted monocyclic arylene group; or a substituted or unsubstituted polycyclic arylene group. In one embodiment of the present invention, L601 and L602 are the same or different and each independently represent a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylylene group; or a substituted or unsubstituted naphthylene group. In one embodiment of the present invention, said L601 and L602 are each a direct bond.

[0207] In one embodiment of the present invention, Ar601 and Ar602 are the same or different and each independently represent a substituted or unsubstituted aryl group. In one embodiment of the present invention, Ar601 and Ar602 are the same or different and each independently represent a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group. In one embodiment of the present invention, Ar601 and Ar602 are the same or different and each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted pyrenyl group; or a substituted or unsubstituted fluorenyl group. In one embodiment of the present invention, Ar601 and Ar602 are the same or different and each independently represent a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group. In one embodiment of the present invention, Ar601 and Ar602 are each a naphthyl group.

[0208] In one embodiment of the present invention, R601 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R601 is a substituted or unsubstituted phenyl group.

[0209] In one embodiment of the present invention, the formula ET-1 has the following structure:

[0210] [ka]

[0211] In one embodiment of the present invention, the hole-blocking layer is a layer that blocks holes from reaching the cathode and may be generally formed under the same conditions as the hole-injection layer. Specific examples of hole-blocking materials include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0212] In one embodiment of the present invention, the electron blocking layer is a layer that blocks electrons from reaching the anode, and any material known in the art may be used.

[0213] The organic light emitting device according to the present invention may be top-emitting, bottom-emitting or double-sided emitting, depending on the materials used. [Example]

[0214] Hereinafter, the present invention will be described in detail with reference to examples. However, the examples according to the present invention may be modified in various different forms, and the scope of the present invention should not be construed as being limited to the examples described below. The examples of the present invention are provided to more completely explain the present invention to those skilled in the art.

[0215] <Production example> Preparation Example 1. Preparation of Compound 1 (1) Synthesis of Intermediate 1-1 [ka]

[0216] 1-Bromo-4-fluorobenzene (27.9 mL, 255 mmol, 1.7 eq) was added to tetrahydrofuran (THF) (500 mL). After purging with nitrogen, the mixture was cooled to -78°C. n-Butyllithium (n-BuLi) (2.5 M in Hex) (96 mL, 240 mmol, 1.6 eq) was added to a dropping funnel and slowly added to the reaction mixture. The mixture was stirred at -78°C for 30 minutes. 2-Bromofluorenone (38.9 g, 150 mmol) was then added. The mixture was gradually warmed to room temperature and stirred overnight. Distilled water was added to terminate the reaction, followed by extraction with ethyl acetate and water. The organic layer was collected, dried over magnesium sulfate (MgSO4), and filtered. The filtrate was dried on a vacuum rotary evaporator, and the organic solvent was removed to obtain Intermediate 1-1.

[0217] (2) Synthesis of Intermediate 1-2 [ka]

[0218] Intermediate 1-1 (53 g, 150 mmol) and phenol (70.6 g, 750 mmol, 5 eq) were placed in a round-bottom flask (RBF). Methanesulfonic acid (CHSOH) (214 mL, 0.7 M) was added and the mixture was stirred at 60°C for 4 hours. Ice water was added and the mixture was extracted with ethyl acetate and water. The organic layer was collected, dried over MgSO, and filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, the mixture was crystallized from dichloromethane / heptane, yielding 40.6 g of intermediate 1-2.

[0219] (3) Synthesis of intermediate 1-3 [ka]

[0220] Intermediate 1-2 (40 g, 92.7 mmol), 4-nitrobenzaldehyde (21.2 g, 139 mmol, 1.5 eq), copper(II) acetate (Cu(OAc)2) (842 mg, 4.64 mmol, 5 mol%), and cesium carbonate (Cs2CO3) (45.3 g, 139 mmol, 1.5 eq) were placed in a RBF. Dimethylformamide (DMF) (310 mL) was added and the mixture was stirred at 100 °C for 4 h. The mixture was extracted with ethyl acetate and water, and the organic layer was collected. The organic layer was dried over MgSO4 and then filtered. The filtrate was dried on a vacuum rotary evaporator to remove the organic solvent. After column purification, the mixture was crystallized from dichloromethane / heptane (DCM / heptane) to obtain 38.7 g of intermediate 1-3.

[0221] (4) Synthesis of intermediate 1-4 [ka]

[0222] Methyltriphenylphosphonium bromide (CH3PPh3Br) (51.6 g, 144.6 mmol, 2 eq), potassium tert-butoxide (KOtBu) (16.2 g, 144.6 mmol, 2 eq), and THF (217 mL) were added to an RBF and cooled to 0 °C. A solution of intermediate 1-3 (38.7 g, 72.3 mmol) dissolved in tetrahydrofuran (THF) (144 mL) was added to the reaction mixture. The mixture was stirred for 1 hour while warming to room temperature. Extraction was performed with ethyl acetate and water, and the organic layer was collected. The organic layer was dried over MgSO4 and then filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, the product was crystallized from dichloromethane / ethanol (DCM / EtOH) to obtain 33.7 g of intermediate 1-4.

[0223] (5) Synthesis of Compound 1 [ka]

[0224] Compound I1 (1.29 g, 2.5 mmol), intermediate 1-4 (2.93 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(0) (Pd(PtBu3)2) (64 mg, 0.125 mmol, 5 mol%), and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 eq) were placed in a RBF. After purging with nitrogen, toluene (12.5 mL) was added and the mixture was stirred at 90 °C for 1 h. Extraction was performed with ethyl acetate and water, and the organic layer was collected. The organic layer was dried over MgSO4 and then filtered. The filtrate was dried on a vacuum rotary evaporator to remove the organic solvent. After column purification, the mixture was crystallized from DCM / EtOH to obtain 2.6 g of compound 1. LC-MS and NMR confirmed the synthesis of compound 1. MS: [M+H] + =1422 NMR measurement of compound 1: 1H NMR(500 MHz,DMSO-d6) δ 8.02(m,2H),7.87-7.70(m,8H),7.47-7.32(m,8H),7.31-7.15(m,10H),7.05-6.90(m,8H),6.90-6 .85(m,12H),6.77-6.65(m,8H),6.53(d,4H),6.51(m,2H),6.36(m,2H),5.71(dd,2H),5.18(dd,2H)

[0225] Preparation Example 2: Preparation of Compound 2 [ka]

[0226] 2.8 g of Compound 2 was obtained in the same manner as in Preparation Example 1, except that Compound I2 was used instead of Compound I1 in (5) of Preparation Example 1. LC-MS and NMR confirmed that Compound 2 had been synthesized. MS: [M+H] + =1584 NMR data of compound 2: 1 H NMR(500 MHz,DMSO-d6) δ 8.02(m,2H),7.86-7.69(m,10H),7.44-7.33(m,8H),7.31-7.15(m,12H),7.01-6.91(m,8H),6.87-6 .81(m,12H),6.78-6.65(m,8H),6.55(d,4H),6.50(m,2H),6.35(m,2H),5.71(dd,2H),5.18(dd,2H)

[0227] Preparation Example 3: Preparation of Compound 3 [ka]

[0228] 2.6 g of Compound 3 was obtained in the same manner as in Preparation Example 1, except that Compound I3 was used instead of Compound I1 in (5) of Preparation Example 1. LC-MS and NMR confirmed that Compound 3 had been synthesized. MS: [M+H] + =1584 NMR data of compound 3: 1 H NMR(500 MHz,DMSO-d6) δ 7.93(m,2H),7.80-7.73(m,10H),7.41-7.25(m,18H),7.09-6.80(m,32H),6.70-6.61(m,4H),6.45(m,2H),5.68(dd,2H),5.18(dd,2H)

[0229] Preparation Example 4: Preparation of Compound 4 [ka]

[0230] 2.9 g of compound 4 was obtained in the same manner as in Preparation Example 1, except that compound I4 was used instead of compound I1 in (5) of Preparation Example 1. LC-MS and NMR confirmed that compound 4 had been synthesized. MS: [M+H] + =1736 NMR data of compound 4: 1 H NMR(500 MHz,DMSO-d6) δ 8.07(m,2H),7.98(m,2H),7.82-7.67(m,12H),7.47(m,2H),7.39-7.22(m,20H),7.09-6.9 3(m,24H),6.89-6.84(m,6H),6.79(m,2H),6.64-6.50(m,6H),5.62(dd,2H),5.12(dd,2H)

[0231] Preparation Example 5. Preparation of Compound 5 (1) Synthesis of intermediate 5-1 [ka]

[0232] Intermediate 5-1 was produced in the same manner as in Production Example 1(1), except that 1-bromo-2,6-difluorobenzene (29.4 mL, 255 mmol, 1.7 eq) was used instead of 1-bromo-4-fluorobenzene.

[0233] (2) Synthesis of intermediate 5-2 [ka]

[0234] Intermediate 5-2 (45.2 g) was obtained by the same method as in Preparation Example 1 (2), except that Intermediate 5-1 (56 g, 150 mmol) was used instead of Intermediate 1-1.

[0235] (3) Synthesis of intermediate 5-3 [ka]

[0236] 39.8 g of Intermediate 5-3 was obtained by the same method as in (3) of Preparation Example 1, except that Intermediate 5-2 (45.2 g, 100 mmol) was used instead of Intermediate 1-2.

[0237] (4) Synthesis of intermediate 5-4 [ka]

[0238] 34.8 g of Intermediate 5-4 was obtained in the same manner as in (4) of Preparation Example 1, except that Intermediate 5-3 (39.8 g, 72 mmol) was used instead of Intermediate 1-3.

[0239] (5) Synthesis of Compound 5 [ka]

[0240] 2.6 g of compound 5 was obtained by the same method as in Preparation Example 1(5), except that compound I5 (1.85 g, 2.5 mmol) and intermediate 5-4 (2.93 g, 5.5 mmol) were used instead of compound I1 and intermediate 1-4 in Preparation Example 1(5). LC-MS and NMR confirmed the synthesis of compound 5. MS: [M+H] + =1682 NMR data of compound 5: 1 H NMR(500 MHz,DMSO-d6) δ 8.04(m,2H),7.87-7.70(m,8H),7.47-7.32(m,10H),7.31-7.15(m,8H),7.05-6.90(m,8H),6.90-6 .85(m,12H),6.77-6.65(m,8H),6.53(d,4H),6.51(m,2H),6.36(m,2H),5.71(dd,2H),5.18(dd,2H)

[0241] Preparation Example 6: Preparation of Compound 6 [ka]

[0242] 3.5 g of compound 6 was obtained in the same manner as in Preparation Example 1 (5), except that compound I6 (1.85 g, 2.5 mmol) and intermediate 5-4 (2.93 g, 5.5 mmol) were used instead of compound I1 and intermediate 1-4 in Preparation Example 1 (5). LC-MS and NMR confirmed the synthesis of compound 6. MS: [M+H] + =1873 NMR data of compound 6: 1 H NMR(500 MHz,DMSO-d6) δ 8.28(d,2H),8.10(m,2H),7.90-7.67(m,14H),7.46(m,2H),7.38-7.20(m,20H),7.09-6.9 3(m,24H),6.89-6.84(m,6H),6.76(m,2H),6.62-6.73(m,6H),5.62(dd,2H),5.12(dd,2H)

[0243] Preparation Example 7: Preparation of Compound 7 (1) Synthesis of intermediate 7-1 [ka]

[0244] Intermediate 1-2 (8.63 g, 20 mmol) and Cs2CO3 (8.47 g, 26 mmol, 1.3 eq) were placed in a RBF. DMF (100 mL) and 3-ethyl-3-iodomethyloxetane (4 mL, 26 mmol) were added and stirred at 60 °C for 4 h. Extraction was performed with ethyl acetate and water, and the organic layer was collected. After drying with MgSO4, the organic layer was filtered. The filtrate was dried on a vacuum rotary evaporator to remove the organic solvent. After column purification, the product was crystallized in DCM / heptane to obtain 12.3 g of intermediate 7-1.

[0245] (2) Synthesis of Compound 7 [ka]

[0246] 2.6 g of compound 7 was obtained by the same method as in Preparation Example 1 (5), except that compound I7 (1.7 g, 2.5 mmol) and intermediate 7-1 (2.91 g, 5.5 mmol) were used instead of compound I1 and intermediate 1-4 in Preparation Example 1 (5). LC-MS and NMR confirmed the synthesis of compound 7. MS: [M+H] + =1576 NMR data of compound 7: 1 H NMR(500 MHz,DMSO-d6) δ 7.77-7.73(m,4H),7.68-7.55(m,4H),7.52-7.46(m,4H),7.41-7.32(m,10H),7.24-7.13(m ,4H),7.10-6.38(m,30H),4.39(m,4H),4.30(m,4H),3.99(m,4H),1.75(m,4H),0.84(m,6H)

[0247] Preparation Example 8: Preparation of Compound 8 (1) Synthesis of intermediate 8-1 [ka]

[0248] Intermediate 1-2 (39 g, 90 mmol), benzocyclobutane-4-boronic acid (20 g, 135 mmol), Cu(OAc)2 (16.4 g, 90 mmol, 1 eq), and 4 Å molecular sieves (90 g) were placed in a RBF. DCM (900 mL) and triethylamine (TEA) (63 mL, 450 mmol, 5 eq) were added and stirred overnight at room temperature. The mixture was extracted with ethyl acetate and water, and the organic layer was collected. The organic layer was dried over MgSO4 and then filtered. The filtrate was dried on a vacuum rotary evaporator to remove the organic solvent. After column purification, the mixture was crystallized from DCM / EtOH to yield 15 g of intermediate 8-1.

[0249] (2) Synthesis of Compound 8 [ka]

[0250] 3 g of compound 8 was obtained in the same manner as in Preparation Example 1 (5), except that compound I8 (1.7 g, 2.5 mmol) and intermediate 8-1 (2.93 g, 5.5 mmol) were used instead of compound I1 and intermediate 1-4 in Preparation Example 1 (5). LC-MS and NMR confirmed the synthesis of compound 8. MS: [M+H] + =1584 NMR data of compound 8: 1 H NMR(500 MHz,DMSO-d6) δ 7.93(m,2H),7.78-7.72(m,10H),7.39-7.24(m,14H),7.09-6.93(m,24H),6 .85(m,2H),6.78-6.65(m,8H),6.61(d,2H),6.44(m,2H),3.04-2.97(m,8H)

[0251] Preparation Example 9: Preparation of Compound 9 (1) Synthesis of intermediate 9-1 [ka]

[0252] Intermediate 9-1 was produced in the same manner as in Production Example 1(1), except that 1-bromo-2,3,4,5,6-pentafluorobenzene (1-bromo-2,3,4,5,6-pentafluorobenzene) (31.8 mL, 255 mmol) was used instead of 1-bromo-4-fluorobenzene.

[0253] (2) Synthesis of intermediate 9-2 [ka]

[0254] 52.8 g of Intermediate 9-2 was obtained by the same method as in (2) of Preparation Example 1, except that Intermediate 9-1 (64.1 g, 150 mmol) was used instead of Intermediate 1-1.

[0255] (3) Synthesis of intermediate 9-3 [ka]

[0256] 48.6 g of Intermediate 9-3 was obtained in the same manner as in (3) of Preparation Example 1, except that Intermediate 9-2 (50.3 g, 100 mmol) was used instead of Intermediate 1-2.

[0257] (4) Synthesis of intermediate 9-4 [ka]

[0258] Intermediate 9-4 (31 g) was obtained by the same method as in (4) of Preparation Example 1, except that Intermediate 9-3 (43.7 g, 72 mmol) was used instead of Intermediate 1-3.

[0259] (5) Synthesis of Compound 9 [ka]

[0260] 2.8 g of compound 9 was obtained by the same method as in Preparation Example 1 (5), except that compound I9 (1.67 g, 2.5 mmol) and intermediate 9-4 (3.3 g, 5.5 mmol) were used instead of compound I1 and intermediate 1-4 in Preparation Example 1 (5). LC-MS and NMR confirmed the synthesis of compound 9. MS: [M+H] + =1717 NMR data of compound 9: 1 H NMR(500 MHz,DMSO-d6) δ 8.08(m,2H),8.02(m,2H),7.87-7.70(m,10H),7.47-7.32(m,10H),7.15(m,2H),7.05-6.90(m,8H),6.9 0-6.85(m,12H),6.77-6.65(m,8H),6.53(d,4H),6.51(m,2H),6.36(m,2H),5.71(dd,2H),5.18(dd,2H)

[0261] <Element example> Experimental Example 1 A glass substrate coated with a 1,500 Å thick thin film of ITO (indium tin oxide) was placed in distilled water with dissolved detergent and ultrasonically cleaned. The detergent used was from Fischer Co., and the distilled water was filtered through a Millipore Co. filter. After cleaning the ITO for 30 minutes, it was ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning, the substrate was ultrasonically cleaned with isopropyl and acetone solvents, dried, and then washed for 5 minutes before being transported to a glove box.

[0262] 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 on the ITO transparent electrode, and the ink was heat-treated at 220°C for 30 minutes to form a hole injection layer with a thickness of 400 Å.

[0263] A 2 wt % toluene ink containing the following compound A was spin-coated onto the hole injection layer and heat-treated at 120°C for 10 minutes to form a hole transport layer with a thickness of 200 Å. A 92:8 weight ratio of compound B and compound C was vacuum-deposited onto the hole transport layer to form a 200 Å emissive layer. A 350 Å thick electron transport and injection layer was formed on the emissive layer by vacuum-depositing the following compound D. A 10 Å thick LiF layer and a 1000 Å thick aluminum layer were sequentially vapor-deposited onto the electron transport and injection layer to form a cathode.

[0264] [ka]

[0265] During the above process, the deposition rate of the organic material was maintained at 0.4 Å / sec to 0.7 Å / sec, the deposition rate of the cathode lithium fluoride was maintained at 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. The vacuum level during deposition was 2×10 -7 torr~5×10 -8 torr was maintained.

[0266] Experimental Examples 2-9 An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 below was used instead of Compound 1 when manufacturing the hole injection layer (HIL).

[0267] Comparative Examples 1 to 15 An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 below was used instead of Compound 1 when manufacturing the hole injection layer.

[0268] Compounds CE1 to CE15 used in Comparative Examples 1 to 15 are as follows.

[0269] [ka]

[0270] [ka]

[0271] The organic light emitting devices manufactured in the above experimental examples and comparative examples were subjected to a current of 10 mA / cm 2 The driving voltage, external quantum efficiency, luminance, and lifetime were measured at a current density of 100 mA, and the results are shown in Table 1 below. The external quantum efficiency was calculated by dividing the number of emitted photons by the number of injected charge carriers. T95 refers to the time (hr) required for the luminance to decrease to 95% from the initial luminance (500 nit).

[0272] [Table 1]

[0273] Experimental Examples 1 to 9 used the compound represented by Chemical Formula 1 according to the present invention as a host for the hole injection layer, and Comparative Examples 1 to 15 used compounds CE1, CE2, CE11 to CE15 (Comparative Examples 1, 2, 11 to 15) to which no fluoro group (-F) is bonded, compound CE3 (Comparative Example 3) containing four or more curing groups, compound CE4 (Comparative Example 4) containing no curing group, or compounds CE5 to CE10 (Comparative Examples 5 to 10) containing an aryl group instead of a heteroaryl group.

[0274] As shown in Table 1, the organic light-emitting devices (Experimental Examples 1 to 9) using the compound represented by Chemical Formula 1 according to the present invention as a host for the hole injection layer exhibited significantly reduced driving voltage and significantly improved lifetime compared to the organic light-emitting devices of Comparative Examples 1 to 15. Furthermore, the organic light-emitting devices of Experimental Examples 1 to 9 exhibited increased efficiency and brightness compared to the organic light-emitting devices of Comparative Examples 1 to 15. This confirms that the heteroaryl group (e.g., dibenzofuran group) and fluoro group (-F) introduced into the molecule improved film and interface properties, and the change in HOMO level improved hole mobility and hole / electron balance, thereby improving the performance of the organic light-emitting device. On the other hand, the compound of Comparative Example 3, which used a compound having four or more curing groups, did not cure even after heat treatment, and the remaining curing groups likely increased the driving voltage and reduced lifetime. The compound of Comparative Example 4, which used a compound without curing groups, lacked solvent resistance even after heat treatment. Therefore, most of the materials were washed away during the formation of the hole transport layer (HTL), resulting in the device not functioning properly. [Explanation of symbols]

[0275] 101 Circuit board 201...1st electrode 301 Hole injection layer 401 Hole transport layer 501 Light-emitting layer 601 Electron transport and injection layer 701...Second electrode

Claims

1. A compound represented by the following chemical formula 1: 【Chemistry 1】 In the above Chemical Formula 1, Cy1 to Cy4 are the same or different and each independently represent a substituted or unsubstituted hydrocarbon ring group having 6 to 30 carbon atoms; Y and Y are the same or different and each independently represents O or S; L is a substituted or unsubstituted divalent hydrocarbon ring group having 6 to 30 carbon atoms, L1 to L4 are the same or different and each independently represent a direct bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; L10 and L11 are the same or different and each independently represent a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; X1 and X2 are the same or different and each independently represents a curable group; R1 to R4 are the same or different and each independently represent hydrogen; deuterium; or an alkyl group having 1 to 30 carbon atoms; n1 and n2 each represent an integer of 0 to 4, and when n1 and n2 each represent an integer of 2 or more, the two or more parenthesized substituents may be the same or different. m1 and m2 are each an integer of 1 to 5, n1+m1 is 5 or less, and n2+m2 is 5 or less; n3 and n4 each represent an integer of 1 to 7, and when n3 and n4 each represent 2 or more, the two or more parenthesized substituents are the same or different from each other; A compound wherein the curable group has one of the following structures: 【Chemistry 2】 In the above structure: L51 to L56 are the same or different and each independently represent a group formed by linking one or more members selected from the group consisting of a direct bond; —O—; a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; and a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; 【Transformation 3】 is the site of attachment to Chemical Formula 1, and The term "substituted or unsubstituted" in the above description means that the group is substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; an alkyl group having 1 to 30 carbon atoms; and an aryl group having 6 to 30 carbon atoms, or is substituted with a substituent in which two or more of the substituents listed above are linked together, or has no substituents at all.

2. The compound of claim 1, wherein the formula 1 is the following formula 2: 【Chemistry 4】 In the above Chemical Formula 2, The definitions of Cy1 to Cy4, Y1, Y2, L, L1 to L4, L10, L11, X1, X2, R1 to R4, n1 to n4, m1, and m2 are as in Chemical Formula 1.

3. The compound of claim 1 , wherein the formula 1 is the following formula 3: 【Transformation 5】 In the above Chemical Formula 3, Y1, Y2, L, L1 to L4, L10, L11, X1, X2, R1 to R4, n1 to n4, m1, and m2 are defined as in Chemical Formula 1; R50 and R51 are the same or different and each independently represent hydrogen or deuterium, or combine with the adjacent group to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms; n50 and n51 each represent an integer of 1 to 7, and when n50 and n51 each represent 2 or more, the two or more parenthesized substituents are the same or different from each other, and The term "substituted or unsubstituted" in the above description means that the group is substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; an alkyl group having 1 to 30 carbon atoms; and an aryl group having 6 to 30 carbon atoms, or is substituted with a substituent in which two or more of the substituents listed above are linked together, or has no substituents at all.

4. 2. The compound of claim 1, wherein L is one of the following structures: 【Transformation 6】 In the above structure: R10 to R31 are the same or different and each independently represent hydrogen; deuterium; a halogen group; an alkyl group having 1 to 30 carbon atoms; or an aryl group having 6 to 30 carbon atoms; n10 to n21 each represent an integer of 1 to 4, n22, n23, n28, and n29 each represent an integer of 1 to 3, n24 and n25 each represent an integer of 1 to 7, n26 is an integer of 1 to 8, and n27 is an integer of 1 to 6; when n10 to n29 each represent 2 or more, the two or more parenthesized substituents are the same or different from each other; 【Transformation 7】 is the site of attachment to Chemical Formula 1.

5. L10 and L11 are the same or different and each independently represent a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group; The term "substituted or unsubstituted" in the above description means that the group is substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; an alkyl group having 1 to 30 carbon atoms; and an aryl group having 6 to 30 carbon atoms, or is substituted with a substituent in which two or more of the substituents listed above are linked, or has no substituents. The compound of claim 1.

6. The compound of claim 1 , wherein the compound of Formula 1 has one of the following structures: 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 。

7. A coating composition comprising the compound according to any one of claims 1 to 6.

8. first electrode; a second electrode; and One or more organic layers provided between the first electrode and the second electrode Including, The organic light-emitting device, wherein at least one of the organic material layers comprises the coating composition according to claim 7 or a cured product thereof.

9. The organic light-emitting device according to claim 8 , wherein the organic material layer comprising the coating composition or the cured product thereof is a hole transport layer, a hole injection layer, or a layer that simultaneously transports and injects holes.

10. providing a first electrode; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer; Including, The method for manufacturing an organic light emitting device, wherein the forming of the organic material layer comprises forming one or more organic material layers using the coating composition according to claim 7 .

11. The step of forming an organic layer using the coating composition includes: coating the coating composition; and and subjecting the coated coating composition to a heat treatment or light treatment. The method for producing an organic light-emitting device according to claim 10 , comprising:

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