Compound, coating composition containing same, organic light-emitting device using same, and method for producing 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 compounds, coating compositions including the compounds, organic light-emitting devices formed using the coating compositions, and methods for producing the same. [Background technology]

[0003] The organic light-emitting phenomenon is an example of a phenomenon in which electric current is converted into visible light by an internal process of a specific organic molecule. The principle of the organic light-emitting phenomenon is as follows. When an organic layer is placed between an anode and a cathode, and an electric current is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and anode, respectively. The electrons and holes injected into the organic layer recombine to form excitons, which then fall back to the ground state to emit light. An organic light-emitting device using this principle may generally be composed of a cathode, an anode, and organic layers positioned therebetween, such as a hole injection layer, a hole transport layer, an emission 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, when manufacturing organic light-emitting devices using a deposition process, there are problems such as a large loss of materials and the difficulty of 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 formula 1: [ka]

[0008] In the above Chemical Formula 1, Cy1 to Cy4 are the same or different and each independently represents 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 represents 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 represents a substituted or unsubstituted arylene group; X1 and X2 are the same or different and each independently represents a curable group; R and R1 to R4 are the same or different and each independently represents 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 are each an integer of 0 to 4, and when n1 and n2 are each 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 each represents an integer of 1 to 7, and when n3 and n4 each represents 2 or more, the two or more substituents in the 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 layers disposed between the first electrode and the second electrode, wherein at least one of the organic 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 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 comprises forming one or more organic material layers using the coating composition. Effect of the Invention

[0012] In one embodiment of the compound of the present invention, a heteroaryl group is introduced near N, which makes it easy to adjust the energy level, and therefore when applied to an organic layer, it shows the effect of improving the interface characteristics with other layers and facilitating hole mobility. In addition, the compound has excellent hole mobility by including 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 is possible to obtain an element having low driving voltage, excellent luminous efficiency, and / or long life characteristics.

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

[0015] In addition, the compound according to an embodiment of the present invention is resistant to certain solvents after curing, allowing solution processing during device fabrication, thereby enabling devices to have a large area. [Brief description of the drawings]

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

[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 represents 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 represents 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 represents a substituted or unsubstituted arylene group; X1 and X2 are the same or different and each independently represents a curable group; R and R1 to R4 are the same or different and each independently represents 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 are each an integer of 0 to 4, and when n1 and n2 are each 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 each represents an integer of 1 to 7, and when n3 and n4 each represents 2 or more, the two or more substituents in the parentheses are the same or different.

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

[0021] In addition, the compound has a high HOMO (highest occupied molecular orbital) energy level value by introducing a heteroaryl group close to the N.

[0022] Therefore, when the compound is introduced into a hole injection layer or a hole transport layer in an organic light emitting device, the interface characteristics with the adjacent layer are improved, and hole transport is facilitated. In particular, when the compound of Formula 1 is contained in 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 effect on improving the life of the device.

[0023] In addition, the compound has an advantage that it has excellent solubility and therefore various solvents can be selected when producing a coating composition.

[0024] In addition, the compound has the advantage that it forms a completely cured thin film through heat or light treatment, and thus forms a stable thin film that is not damaged during the subsequent solution process.

[0025] Furthermore, the compounds are resistant to certain solvents after curing, allowing solution processing during device fabrication, which allows devices to be fabricated with larger areas.

[0026] In this specification, 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 is larger in the negative direction from the vacuum level.

[0027] In this specification, when a member (layer) is said to be "located 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 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 specifically stated to the contrary.

[0029] The substituents in this specification are described in detail below.

[0030] As used herein, the term "curable group" may refer to a reactive substituent that crosslinks compounds when exposed to heat and / or light. Crosslinks can be generated by linking radicals generated by decomposition of carbon-carbon multiple bonds or cyclic structures by heat treatment or light irradiation.

[0031] In this specification, "C x1-x2 " means "carbon number x1 to x2."

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

[0033] In this specification, the term "adjacent" groups may refer to a substituent substituted on an atom directly connected 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 the ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring can be interpreted as "adjacent" groups to each other.

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

[0035] In this specification, 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 from each other.

[0036] In this specification, the term "substituted or unsubstituted" means that it is substituted with one or more substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amine, aryl, and heteroaryl, or that it is substituted with a substituent in which two or more of the above-listed substituents are linked, or that it does not have any substituents. For example, the "substituent in which two or more substituents are linked" may be a biphenyl group. That is, the 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 thereto.

[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 is preferably 1 to 60. According to one embodiment, the number of carbon atoms of 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 alkylene group refers to an alkyl group having two bonding positions, i.e., a divalent group. The above description of the alkyl group 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 it is preferable that the number of carbon atoms is 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 the present specification, the aryl group is not particularly limited, and 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, a fluorenyl group may be optionally substituted, and two substituents may be bonded together to form a spiro structure.

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

[0046] In this specification, the heterocyclic group is an aromatic, aliphatic, or aromatic and 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 the present 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 of 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 condensed.

[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 the present specification, an arylene group refers to an aryl group having two bonding positions, i.e., a divalent group. The above description of the aryl group may be applied, except that these are divalent groups.

[0052] In the present specification, the heteroarylene group refers to a heteroaryl group having two bonding positions, i.e., a divalent group. The above description of the heteroaryl group 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 represents a group to which 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 are linked; [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 any 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 any 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 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, The definitions of Cy1 to Cy4, Y1, Y2, L, L1 to L4, X1, X2, R1 to R4, n1 to n4, m1, and m2 are 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; Each of n5 and n6 is an integer of 0 to 4, and when each of n5 and n6 is 2 or more, the two or more substituents in the 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; 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 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 represents a substituted or unsubstituted aromatic ring. In one embodiment of the present invention, Cy1 to Cy4 are the same or different and each independently is 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 represents 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 combined with adjacent groups to form a substituted or unsubstituted ring; n50 and n51 each represents an integer of 1 to 7, and when n50 and n51 each represents 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 represents 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 each represents an integer of 1 to 7, n62 and n63 each represents an integer of 1 to 9, and when n60 to n63 each represents 2 or more, the substituents in the two or more brackets are the same or different from each other.

[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 above 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 represents 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 each represents an integer of 1 to 7, n62 and n63 each represents an integer of 1 to 9, and when n60 to n63 each represents 2 or more, the substituents in the two or more brackets are the same or different from each other.

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

[0087] In one embodiment of the present invention, L is substituted or unsubstituted C 6-60 or a substituted or unsubstituted C 2-60 is a divalent heterocyclic group. In one embodiment of the present invention, L is substituted or unsubstituted C 6-30 or a substituted or unsubstituted C 2-30 is a divalent heterocyclic group. According to another embodiment, the L is a 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 which is unsubstituted or substituted 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 represents 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 represents an integer of 1 to 4, n22, n23, n28, and n29 each represents an integer of 1 to 3, n24 and n25 each represents 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 represents 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 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, the L1 to L4 are the same or different and each independently represent a direct bond; 6-60 or a substituted or unsubstituted C 2-60 is a heteroarylene 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 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, the L1 to L4 are the same or different and each independently represent a direct bond; deuterium, F, or C. 1-20 or a phenylene group substituted or unsubstituted with an alkyl group of the formula: 1-20 and the biphenylene group is unsubstituted or substituted 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; a substituted or unsubstituted C 1-20alkyl group; substituted or unsubstituted C 1-20 alkoxy groups; 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 represents 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 may be prepared as shown in the following reaction scheme: In this case, the substituents may be bonded by a method known in the art, and the type, position, or number of the substituents may be changed by a technique known in the art.

[0104] <Reaction formula> [ka]

[0105] In the above 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 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 normal temperature and normal pressure.

[0109] In one embodiment of the 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 resistance to a solvent during heat treatment after coating, i.e., the compound is insoluble in a particular solvent due to crosslinking after coating.

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

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

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

[0114] For example, when the coating composition is applied to a hole injection layer, it has the advantage that in manufacturing an overlayer (such as a hole transport layer), the overlayer can be solution processed using a particular solvent that the cured coating composition is resistant to.

[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 that can dissolve or disperse a compound according to an embodiment of the present invention 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. However, the solvent is not limited to these, as long as it is capable of dissolving or dispersing a compound according to an 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 invention, the coating composition further comprises a p-doping material.

[0119] In the present specification, the p-doping material refers to a material that causes a host material to have p-semiconductor properties. The p-semiconductor properties refer to the properties of a material that receives or transports holes at the highest occupied molecular orbital (HOMO) energy level, i.e., has 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 kinds of p-doping materials 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 included in an amount of 0 to 50 wt % based on the total solid content of the coating composition. In one embodiment of the present invention, the p-doping material is included in an amount of 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 that contains functional groups that are crosslinkable by heat or light; or a monomer that contains end groups that are capable of forming a polymer by heat.

[0126] In one embodiment of the present invention, the monomer containing a functional group capable of being crosslinked by heat or light; or the monomer containing an end group capable of forming 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 a monomer containing an end group capable of forming a polymer by heat may be a monomer in which an aryl such as phenyl, biphenyl, fluorene, or naphthalene is substituted with a functional group crosslinkable by heat or light or an end group capable of forming a polymer by heat.

[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 the element.

[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 layers disposed between the first electrode and the second electrode, at least one of the organic layers comprising the coating composition or a cured product thereof, wherein 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 comprising the coating composition or a cured product thereof is a hole transport layer, a hole injection layer, or a layer which 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 which 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 transports electrons and injects electrons.

[0137] In one embodiment of the 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 one 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 laminated in this order on a substrate.

[0140] In one 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 laminated on a substrate.

[0141] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are laminated.For example, the organic light-emitting device of the present invention may have a structure including two or more layers selected from 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 transports electrons and injects electrons.However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic 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 thereto.

[0145] When the organic light emitting device includes a plurality of organic layers, the organic 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 a structure such as the following examples. (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 replaced with an "electron transport and injection layer" or a "simultaneous electron transport and electron injection layer".

[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 by 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, an organic layer, and a cathode on a substrate. In this case, a metal or a conductive metal oxide or an 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, and an organic layer including a hole injection layer, a hole transport layer, an emitting layer, and a layer that simultaneously transports and injects electrons is formed thereon by a solution process, deposition process, etc., and then a material that can be used as a cathode is deposited thereon. In addition to this method, an organic light emitting device can be fabricated by sequentially depositing a cathode material, an organic 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 layers on the first electrode; and forming a second electrode on the organic layers, wherein the step of forming the organic layers includes forming one or more organic 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 has the effect of being time- and cost-effective in the manufacture of 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 step may be performed by heat treatment. The heat treatment temperature in the heat treatment step 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. 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] In the step of 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 includes 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, a plurality of compounds contained in the coating composition can be crosslinked to provide an organic layer having a thin film structure. In this case, when another layer is laminated on the surface of the organic layer formed using the coating composition, it is possible to prevent the organic layer from being dissolved, morphologically affected, or decomposed by a solvent.

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

[0166] In one embodiment of the present invention, the anode material is preferably a material having a large work function so that hole injection into the organic layer can be facilitated.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 SnO2:Sb; 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 having a small 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 materials with a multilayer structure such as LiF / Al or LiO2 / Al.

[0168] In one embodiment of the present invention, the hole injection layer is a layer that injects holes from an electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has a hole injection effect at the anode, has an excellent hole injection effect for the light emitting layer or light emitting material, prevents the movement of excitons generated from the light emitting layer to the electron injection layer or electron injection material, and has excellent thin film forming ability. In addition, 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 the hole injection material include, but are not limited to, the compound of Chemical Formula 1, metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, and polyaniline and polythiophene-based conductive polymers.

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

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

[0171] In one embodiment of the present invention, the hole transport layer comprises a compound of 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 represents 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 luminescent material contained in the luminescent layer is a material that can emit light in the visible light region by receiving and combining holes and electrons transported from the hole transport layer and the 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-hydroxy-quinoline 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, rubrene, etc.

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

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

[0181] [ka]

[0182] In the above chemical formula EH-1, L301 and L302 are the same or different and each independently represents 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 represents 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 are 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 represents 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 a substituted or unsubstituted aryl group. In one embodiment of the present invention, Ar301 and Ar302 are the same or different and each independently 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 represents 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 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 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, periflanthene, or the like having an arylamino group, and the styrylamine compound may be a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, such that 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 are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, or the like may be mentioned, but are not limited thereto. In addition, the metal complex may be an iridium complex, a platinum complex, or the like, but are not limited thereto. More specifically, the dopant may be a compound containing an arylamine group.

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

[0190] [ka]

[0191] In the above chemical formula ED-1, Ar501 to Ar504 are the same or different and each independently represents 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 above formula ED-2, Ar501 to Ar504 are the same as those 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 represents 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 represents 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 are the same or different and each independently represents 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 is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer, and 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 mobility for electrons. Specific examples include, but are not limited to, Al complex of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes, etc. The electron transport layer may be used with any desired cathode material, as used in the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium, each of which is 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 an electrode, and the electron injection material 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 the movement of excitons generated from the light-emitting layer to the hole injection layer, and has excellent thin-film forming ability.Specific examples of the electron injection material include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, benzimidazole, perylene tetracarboxylic acid, phenanthroline, fluorenylidene methane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0201] In one embodiment of the present invention, the metal complex compound may be, but is not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h]quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato) chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolate) gallium, bis(2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis(2-methyl-8-quinolinato) (2-naphtholato) gallium, etc.

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

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

[0204] [ka]

[0205] In the above formula ET-1, L601 and L602 are the same or different and each independently represents 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 represents 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 represents 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 a substituted or unsubstituted aryl group. In one embodiment of the present invention, Ar601 and Ar602 are the same or different and each independently 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 represents 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 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. EXAMPLES

[0214] Hereinafter, the present invention will be described in detail with reference to examples in order to specifically explain the present invention. However, the examples according to the present invention may be modified in various different forms, and the scope of the present invention is not to be construed as being limited to the following examples. The examples of the present invention are provided to more completely explain the present invention to those having ordinary skill 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 (27.9mL, 255mmol, 1.7eq) was added to tetrahydrofuran (THF) (500mL). After replacing with nitrogen, it was cooled to -78℃. n-Butyllithium (n-BuLi) (2.5M in Hex) (96mL, 240mmol, 1.6eq) was added to a dropping funnel and gradually added to the reaction mixture, and then stirred at -78℃ for 30 minutes. 2-Bromofluorenone (38.9g, 150mmol) was added. The temperature was gradually raised to room temperature and stirred overnight. Distilled water was added to terminate the reaction, and then extraction was performed with ethyl acetate and water. The organic layer was collected, dried using magnesium sulfate (MgSO4), and filtered. The filtrate was dried using 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 (53g, 150mmol) and phenol (70.6g, 750mmol, 5eq) were placed in a round bottom flask (RBF). Methanesulfonic acid (CH3SO3H) (214mL, 0.7M) was added and stirred at 60℃ for 4 hours. Ice water was added and then extracted with ethyl acetate and water. The organic layer was collected, dried using MgSO4 and filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, the product was crystallized under dichloromethane / heptane conditions to obtain 40.6g of intermediate 1-2.

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

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

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

[0222] Methyltriphenylphosphonium bromide (CH3PPh3Br) (51.6g, 144.6mmol, 2eq), potassium tert-butoxide (KOtBu) (16.2g, 144.6mmol, 2eq), and THF (217mL) were added to a RBF and cooled to 0°C. A solution of intermediate 1-3 (38.7g, 72.3mmol) dissolved in tetrahydrofuran (THF) (144mL) 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 using MgSO4 and then filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, the intermediate 1-4 was crystallized under the condition of dichloromethane / ethanol (DCM / EtOH) to obtain 33.7g.

[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 nitrogen replacement, toluene (12.5 mL) was added and stirred at 90°C for 1 hour. Extraction was performed with ethyl acetate and water, and the organic layer was collected. The organic layer was dried using MgSO4 and then filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, the mixture was crystallized under DCM / EtOH conditions to obtain 2.6 g of compound 1. The synthesis of compound 1 was confirmed by LC-MS and NMR. 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] In (5) of Preparation Example 1, except that compound I2 was used instead of compound I1, 2.8 g of compound 2 was obtained by the same method as Preparation Example 1. The synthesis of compound 2 was confirmed by LC-MS and NMR. 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] In (5) of Preparation Example 1, except that compound I3 was used instead of compound I1, 2.6 g of compound 3 was obtained by the same method as Preparation Example 1. The synthesis of compound 3 was confirmed by LC-MS and NMR. 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] In (5) of Preparation Example 1, except that compound I4 was used instead of compound I1, 2.9 g of compound 4 was obtained by the same method as Preparation Example 1. The synthesis of compound 4 was confirmed by LC-MS and NMR. 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 in Production Example 1(1).

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

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

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

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

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

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

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

[0240] In the above 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, 2.6 g of compound 5 was obtained by the same method as Preparation Example 1 (5). LC-MS and NMR confirmed that compound 5 was synthesized. 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] In the above 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, 3.5 g of compound 6 was obtained by the same method as Preparation Example 1 (5). LC-MS and NMR confirmed that compound 6 was synthesized. 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 hours. Extraction was performed with ethyl acetate and water, and the organic layer was collected. After drying the organic layer with MgSO4, the organic layer was filtered. The filtrate was dried in a vacuum rotary evaporator to remove the organic solvent. After column purification, the intermediate 7-1 was crystallized under DCM / heptane conditions to obtain 12.3 g.

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

[0246] In the above 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, 2.6 g of compound 7 was obtained by the same method as Preparation Example 1 (5). LC-MS and NMR confirmed that compound 7 was synthesized. 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 (39g, 90mmol), benzocyclobutane-4-boronic acid (20g, 135mmol), Cu(OAc)2 (16.4g, 90mmol, 1eq), and 4Å molecular sieve (90g) were placed in a RBF. DCM (900mL) and triethylamine (TEA) (63mL, 450mmol, 5eq) were added and stirred at room temperature overnight. Extraction was performed with ethyl acetate and water, and the organic layer was collected. After drying the organic layer using MgSO4, the organic solvent was filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, the intermediate 8-1 was crystallized under the condition of DCM / EtOH to obtain 15g.

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

[0250] In the above 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, 3 g of compound 8 was obtained by the same method as Preparation Example 1 (5). It was confirmed by LC-MS and NMR that compound 8 was synthesized. 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 (31.8 mL, 255 mmol) was used instead of 1-bromo-4-fluorobenzene in Production Example 1(1).

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

[0254] Intermediate 9-2 (52.8 g) was obtained by the same method as in Preparation Example 1(2), 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] Intermediate 9-3 (48.6 g) was obtained by the same method as in Preparation Example 1(3), except that Intermediate 9-2 (50.3 g, 100 mmol) was used instead of Intermediate 1-2 in Preparation Example 1(3).

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

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

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

[0260] In the above 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, 2.8 g of compound 9 was obtained by the same method as Preparation Example 1 (5). The synthesis of compound 9 was confirmed by LC-MS and NMR. 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 detergent dissolved therein and ultrasonically cleaned. The detergent used was from Fischer Co., and the distilled water used was distilled water that had been filtered a second time with a Millipore Co. filter. The ITO was washed for 30 minutes, and then ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning was complete, the substrate was ultrasonically cleaned with a solvent of isopropyl and acetone, dried, and then cleaned 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 shown below in a weight ratio of 8:2 was spin-coated on the ITO surface of a transparent electrode, and heat-treated at 220° C. for 30 minutes to form a hole injection layer having a thickness of 400 Å.

[0263] On the hole injection layer, a toluene ink containing 2 wt% of the following compound A was spin-coated and heat-treated at 120°C for 10 minutes to form a hole transport layer having a thickness of 200 Å. On the hole transport layer, the following compounds B and C were vacuum-deposited in a weight ratio of 92:8 to form a light-emitting layer having a thickness of 200 Å. On the light-emitting layer, the following compound D was vacuum-deposited to form an electron transport and injection layer having a thickness of 350 Å. On the electron transport and injection layer, LiF was sequentially deposited to a thickness of 10 Å and aluminum was deposited to a thickness of 1000 Å 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 degree of vacuum 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 the hole injection layer was manufactured.

[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 experimental examples and comparative examples were subjected to a current flow rate of 10 mA / cm 2 The driving voltage, external quantum efficiency, luminance, and lifetime were measured at a current density of 1000 nits, and the results are shown in Table 1 below. The external quantum efficiency was calculated by (number of emitted photons) / (number of injected charge carriers). T95 means the time (hr) required for the luminance to decrease to 95% from the initial luminance (500 nits).

[0272] [Table 1]

[0273] Experimental Examples 1 to 9 use 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 use compounds CE1, CE2, CE11 to CE15 (Comparative Examples 1, 2, 11 to 15) having no fluoro group (-F) bonded thereto, compound CE3 (Comparative Example 3) having four or more curing groups, compound CE4 (Comparative Example 4) having no curing group, or compounds CE5 to CE10 (Comparative Examples 5 to 10) having an aryl group instead of a heteroaryl group.

[0274] As shown in Table 1, it can be confirmed that 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 have a significantly reduced driving voltage and a significantly improved lifespan, compared to the organic light-emitting devices of Comparative Examples 1 to 15. In addition, it can be confirmed that the organic light-emitting devices of Experimental Examples 1 to 9 have increased efficiency and luminance, compared to the organic light-emitting devices of Comparative Examples 1 to 15. As a result, it was confirmed that the heteroaryl group (dibenzofuran group, etc.) and the fluoro group (-F) introduced into the molecule improve the film and interface properties, and the hole mobility and hole / electron balance are improved by the change in the HOMO level, thereby improving the performance of the organic light-emitting device. On the other hand, in the case of Comparative Example 3 using a compound having four or more curing groups, it is considered that the compound does not cure even after heat treatment, and the driving voltage increases and the lifespan decreases due to the remaining curing groups. In the case of Comparative Example 4 using a compound without a curing group, it is found that the compound does not have resistance to the solvent even after heat treatment, so that most of the substances are washed away during the formation of the hole transport layer (HTL), and the device does not operate normally. [Explanation of symbols]

[0275] 101... Substrate 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 represents 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 represents a substituted or unsubstituted arylene group; X1 and X2 are the same or different and each independently represents a curable group; R and R1 to R4 are the same or different and each independently represents 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 an integer of 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; Each of n3 and n4 is an integer of 1 to 7, and when each of n3 and n4 is 2 or more, the two or more substituents in the brackets are the same or different.

2. The compound of claim 1 , wherein the curable group is one of the following structures: 【Chemistry 2】 In the above structure, L51 to L56 are the same or different and each independently represents 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, 【Chemistry 3】 is the site of attachment to Chemical Formula 1.

3. The compound according to 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.

4. The compound according to claim 1 , wherein the formula 1 is the following formula 3: 【Chemistry 5】 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 represents 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; Each of n50 and n51 is an integer of 1 to 7, and when each of n50 and n51 is 2 or more, the two or more substituents in parentheses are the same or different.

5. The compound of claim 1, wherein L is one of the following structures: 【Chemistry 6】 In the above structure, R10 to R31 are the same or different and each independently represents 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 represents an integer of 1 to 4, n22, n23, n28, and n29 each represents an integer of 1 to 3, n24 and n25 each represents 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 represents 2 or more, the two or more substituents in parentheses are the same or different from each other; 【Chemistry 7】 is the site of attachment to Chemical Formula 1.

6. The L1 to L4 are the same or different, and each independently represents a direct bond; or a substituted or unsubstituted C ６－３０ The compound according to claim 1 , wherein the arylene group is

7. R1 to R4 are the same or different and each independently represent hydrogen; deuterium; or substituted or unsubstituted C １－３０ The compound according to claim 1 , wherein the alkyl group is

8. The compound according to claim 1, wherein 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.

9. The compound of formula 1 is the compound of claim 1 having any one of the following structures: 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 。

10. A coating composition comprising a compound according to any one of claims 1 to 9.

11. 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 layers comprises the coating composition according to claim 10 or a cured product thereof.

12. The organic light-emitting device according to claim 11, wherein the organic layer comprising 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.

13. 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 10.

14. The step of forming an organic layer using the coating composition includes: coating the coating composition; and 2. subjecting the coated coating composition to a heat treatment or light treatment. The method for producing an organic light-emitting device according to claim 13, comprising:

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