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

Abstract

The present specification relates to a compound of Chemical Formula 1, a coating composition containing the compound, 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. 10-2021-0121820, filed with the Korean Intellectual Property Office on September 13, 2021, and all of its content is incorporated herein by reference.

[0002] This specification relates to a compound, a coating composition containing the compound, an organic light-emitting device formed using the coating composition, and a method for manufacturing the same.

Background Art

[0003] The organic light-emitting phenomenon is an example in which an 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 positioned between an anode and a cathode and a current is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. The electrons and holes injected into the organic layer recombine to form an exciton, and the exciton falls back to the ground state again, resulting in light emission. An organic light-emitting device using such a principle generally can be composed of a cathode, an anode, and an organic layer positioned therebetween, for example, an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer.

[0004] Conventionally, a deposition process has been mainly used to manufacture an organic light-emitting device. However, there is a problem that a large amount of material loss occurs when manufacturing an organic light-emitting device by the deposition process. To solve this problem, a technique for manufacturing an element by a solution process with less material loss and increased production efficiency has been developed, and the development of substances that can be used during the solution process is required.

[0005] The substances used in an organic light-emitting device for a solution process must have the following properties.

[0006] First, a homogeneous solution that can be stored must be formed. In the case of commercially available materials for vapor deposition processes, due to their good crystallinity and poor solubility in solutions or the tendency to form crystals even when a solution is formed, there is a high possibility that the concentration gradient of the solution will vary or defective elements will be formed depending on the storage period.

[0007] Second, the material used in the solution process must be excellent in coating properties so that no holes or aggregation phenomena occur during thin film formation and a thin film with a uniform thickness can be formed.

[0008] Third, the layer on which the solution process is performed must have resistance to the solvents and materials used in the processes for forming other layers, and is required to be excellent in current efficiency and lifetime characteristics during the manufacture of organic light-emitting devices.

[0009] Therefore, the development of new organic substances is required in this technical field.

Summary of the Invention

Problems to be Solved by the Invention

[0010] This specification provides a compound, a coating composition containing the same, an organic light-emitting device using the same, and a method for manufacturing the same.

Means for Solving the Problems

[0011] One embodiment of the present invention provides a compound of the following Chemical Formula 1.

[0012]

Chem.

[0013] In the above Chemical Formula 1, L1 to L3 are the same as or different from each other, and each independently is a direct bond; -O-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group. L11 and L12 are the same as or different from each other, and each independently is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, Ar1 to Ar4 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, X1 to X3 are the same as or different from each other, and each independently is a photocurable group or a thermosetting group, R1 to R3 and R11 to R16 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, a1 to a3 are each an integer from 1 to 3, When a1 to a3 are each 2 or more, the substituents in parentheses are the same as or different from each other, n1 to n3 are each an integer from 1 to 5, n11 and n16 are each an integer from 1 to 4, n12 to n15 are each an integer from 1 to 3, When n1 to n3 and n11 to n16 are each 2 or more, the substituents in parentheses are the same as or different from each other.

[0014] Another embodiment of the present invention provides a coating composition containing the above compound.

[0015] Another embodiment of the present invention provides an organic light-emitting device including a first electrode; a second electrode; and one or more organic layers including a light-emitting layer provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the above coating composition or a cured product thereof.

[0016] Another embodiment of the present invention includes the steps of preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer, wherein the step of forming the organic layer includes forming one or more organic layers using the coating composition, and provides a method for manufacturing an organic light-emitting device.

Effects of the Invention

[0017] Due to the suitable viscosity of the compound according to one embodiment of the present invention with respect to the solvent, the inkjet process is easy.

[0018] In addition, the compound according to one embodiment of the present invention has the advantage that various solvents can be selected during the production of the coating composition because of its excellent solubility.

[0019] In addition, the compound according to one embodiment of the present invention has the advantage of forming a stable thin film that is not damaged by the next solution process by forming a completely cured thin film by heat treatment or light treatment.

[0020] In addition, the compound according to one embodiment of the present invention shows resistance to a specific solvent after curing, so that a solution process is possible during the production of the device, and thereby, the device can be enlarged in area.

[0021] In addition, the compound according to one embodiment of the present invention can be used as a material for the organic layer of an organic light-emitting device, and can provide a low driving voltage, high luminous efficiency, and / or high lifetime characteristics. In particular, the compound according to one embodiment of the present specification has the effect of lowering the driving voltage when applied to an organic light-emitting device because of its long conjugation length.

Brief Description of the Drawings

[0022]

Figure 1

Best Mode for Carrying Out the Invention

[0023] Hereinafter, the present invention will be described in detail.

[0024] One embodiment of the present invention provides a compound of the following Chemical Formula 1.

[0025]

Chemical Formula

[0026] In Chemical Formula 1 above, L1 to L3 are the same as or different from each other, and each independently is a direct bond; -O-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, L11 and L12 are the same as or different from each other, and each independently is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, Ar1 to Ar4 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, X1 to X3 are the same as or different from each other, and each independently is a photocurable group or a thermosetting group, R1 to R3 and R11 to R16 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, a1 to a3 are each an integer of 1 to 3, When a1 to a3 are each 2 or more, the substituents in parentheses are the same as or different from each other, n1 to n3 are each an integer of 1 to 5, n11 and n16 are each an integer of 1 to 4, n12 to n15 are each an integer of 1 to 3, When n1 to n3 and n11 to n16 are each 2 or more, the substituents in parentheses are the same as or different from each other.

[0027] Generally, in the case of polymers, due to the long conjugation length, the hole mobility is improved, but there is a problem that it is difficult to form an organic layer by a solution process because it does not dissolve well in solvents. On the other hand, in the case of single-molecule compounds, since they dissolve well in solvents, they are advantageous for solution processes, but due to the short conjugation length, there is little hole transfer within the molecule, and hole transfer between molecules becomes the main factor, resulting in an increase in driving voltage and a decrease in efficiency.

[0028] The compound according to one embodiment of the present invention has an effect of exhibiting the advantages of both polymers and single molecules. Specifically, since the compound dissolves well in solvents, an organic layer can be formed by a solution process (or an inkjet process), and since it has excellent hole mobility, when applied to an element, the driving voltage decreases and the efficiency increases.

[0029] Generally, in compounds of the same molecular weight, when the number of N relatively increases, the HOMO level decreases (becomes closer to the vacuum level), and the difference from the HOMO level of the HTL becomes larger, which leads to an increase in the driving voltage. However, the compound of Chemical Formula 1 contains 4 Ns, and each chain is linked via a divalent fluorenyl group and has a long conjugation length. Therefore, it shows the effect of improving the hole mobility, has a smaller molecular weight than polymers, and shows good ink properties.

[0030] That is, the compound of Chemical Formula 1 contains -N-linker-N-divalent fluorene-N-linker-N-, thereby increasing the conjugation length and showing the effect of improving the hole mobility, and showing the effect of lowering the driving voltage and increasing the efficiency when applied to an element.

[0031] In addition, when laminating another layer on the surface of the organic layer formed using the compound, it is also possible to form another layer by a solution process. Such an effect is due to the structural characteristics of the compound of Chemical Formula 1. Specifically, the compound of Chemical Formula 1 contains three or more curable groups, so it has even higher resistance to solvents, and by forming a thin film that is completely cured by heat treatment or light treatment, it has the advantage of forming a stable thin film that is not damaged by the subsequent solution process. Thereby, since it is advantageous for maintaining the film after film formation during the manufacture of the device, there is an advantage that it is applicable to the solution process.

[0032] For example, in the step of forming an organic layer using the compound, crosslinking can be formed by heat treatment or light treatment, so that an organic layer containing a thinned structure can be provided. Further, when laminating another layer on the surface of the organic layer formed as described above, it is possible to prevent dissolution, morphological influence, or decomposition by a solvent. Therefore, when forming another organic layer on the organic layer formed using the compound, the selection range of solvents that can be used becomes wider.

[0033] In addition, in the case of the compound according to an embodiment of the present invention, since an organic light-emitting device can be manufactured by a solution coating method, it is possible to increase the area of the device.

[0034] In this specification, the chain means -N-linker-N of Chemical Formula 1.

[0035] In this specification, the linker means L11 and L12.

[0036] In one embodiment of the present invention, the N may be the N contained in an amine group.

[0037] In one embodiment of the present invention, the molecular weight of the compound of Chemical Formula 1 is 1,000 g / mol to 5,000 g / mol. Thereby, it shows an effect that the viscosity is similar to that of a single molecule and the resistance to a solvent is similar to that of a polymer.

[0038] Therefore, since the viscosity with respect to the solvent is not high, the inkjet process is easier than that of polymers, and there is an advantage of forming a stable thin film that is not damaged by the next solution process after curing.

[0039] In this specification, "single molecule" means a substance consisting of one structure without repeating units.

[0040] In one embodiment of the present invention, the molecular weight of the single molecule is less than 10,000 g / mol. Specifically, it is 100 g / mol to 5,000 g / mol.

[0041] In this specification, "polymer" means a polymer in which the same structure is repeated. That is, it means a polymer having repeating units.

[0042] In one embodiment of the present invention, the number average molecular weight of the polymer is 10,000 g / mol to 5,000,000 g / mol. Specifically, it is 10,000 g / mol to 1,000,000 g / mol.

[0043] In this specification, when a member is located "on" another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.

[0044] In this specification, when a part "includes" a certain component, this means that, unless otherwise stated to the contrary, it does not exclude other components and may further include other components.

[0045] In this specification, "photocurable group or thermosetting group" can mean a reactive substituent that crosslinks between compounds by exposure to light and / or heat. The photocurable group or thermosetting property can be generated by the linking of radicals generated by the decomposition of carbon-carbon multiple bonds or cyclic structures by light irradiation or heat treatment.

[0046] In this specification, the "curable group" is a "photo-curable group or thermo-curable group". Hereinafter, the substituents in this specification will be described in detail.

[0047] In this specification,

Chemical formula

[0048] In this specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and the position where substitution occurs is not limited as long as it is the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted. When two or more substitutions occur, the two or more substituents may be the same or different from each other.

[0049] In this specification, the term "substituted or unsubstituted" means being substituted with one or more substituents selected from the group consisting of deuterium; halogen group; alkyl group; cycloalkyl group; alkoxy group; aryloxy group; amine group; aryl group; and heterocyclic group, or being substituted with a substituent in which two or more of the exemplified substituents are linked, or having no substituent at all. 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.

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

[0051] In this specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0052] In this specification, the alkyl group may be linear or branched, and its carbon number is not particularly limited, but is preferably 1 to 60. According to one embodiment, the carbon number of the alkyl group is 1 to 30. Specific examples of the alkyl group include, but are not limited to, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, etc.

[0053] In this specification, the alkylene group means a group having two bonding positions on the alkyl group, that is, a divalent group. Except that these are divalent groups, the description of the above-mentioned alkyl group may be applicable.

[0054] In this specification, the carbon number of the cycloalkyl group is not particularly limited, but is preferably 3 to 60. According to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. Specific examples of the cycloalkyl group include, but are not limited to, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc.

[0055] In this specification, the alkoxy group may be linear, branched, or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples of the alkoxy group include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc.

[0056] In this specification, the amine group is a group represented by -NR 100 R 101 wherein R 100 and R 101are the same as or different from each other, and each independently is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. Specifically, the amine group may be, but is not limited to, -NH2; an alkylamine group; an arylalkylamine group; an arylamine group; an arylheteroarylamine group; an alkylheteroarylamine group, and a heteroarylamine group. The number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 60.

[0057] In the present specification, the aryl group is not particularly limited, but may have 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. Examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, and a terphenyl group. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, and a fluorenyl group.

[0058] In the present specification, the fluorenyl group may be substituted, or two substituents may be bonded to each other to form a spiro structure.

[0059] When the fluorenyl group is substituted,

Chemical formula

[0060] In the present specification, an arylene group means a group having two bonding positions on an aryl group, that is, a divalent group. The description of the aryl group described above may be applied except that these are each a divalent group.

[0061] In this specification, the heterocyclic group is a heterocyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms, 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 heterocyclic group is 2 to 30. According to another embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of the heterocyclic group include, but are not limited to, pyridyl group, pyrrole group, pyrimidyl group, pyridazinyl group, furanyl group, thiophene group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, etc.

[0062] In this specification, the heteroaryl group may be applicable to the description of the above-mentioned heterocyclic group, except that it is aromatic.

[0063] In this specification, the heteroarylene group means a group having two bonding positions in the heteroaryl group, that is, a divalent group. The description of the above-mentioned heteroaryl group may be applicable, except that these are each a divalent group.

[0064] In one embodiment of the present invention, L1 to L3 are the same as or different from each other, and each independently is a direct bond; -O-; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0065] In one embodiment of the present invention, L1 to L3 are the same as or different from each other, and each independently is a direct bond; -O-; or a substituted or unsubstituted arylene group.

[0066] In one embodiment of the present invention, L1 to L3 are the same as or different from each other, and each independently is a direct bond; -O-; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0067] In one embodiment of the present invention, L1 to L3 are the same as or different from each other, and each independently is a direct bond; -O-; a substituted or unsubstituted phenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted terphenylene group.

[0068] In one embodiment of the present invention, L1 to L3 are the same as or different from each other, and each independently is a direct bond; -O-; or a substituted or unsubstituted phenylene group.

[0069] In one embodiment of the present invention, Chemical Formula 1 is the following Chemical Formula 1-1 or 1-2.

[0070]

Chemical formula

[0071] In Chemical Formulas 1-1 and 1-2, R1 to R3, R11 to R16, L11, L12, Ar1 to Ar4, n1 to n3, and n11 to n16 are the same as the definitions in Chemical Formula 1, L1' to L3' are the same as or different from each other, and each independently is a direct bond; or -O-, X1 to X3 are the same as or different from each other, and each independently is a photocurable group or a thermosetting group.

[0072] In one embodiment of the present invention, R11 to R16 are each hydrogen.

[0073] In one embodiment of the present invention, R1 to R3 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group.

[0074] In one embodiment of the present invention, R1 to R3 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0075] In one embodiment of the present invention, R1 to R3 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; or an alkyl group.

[0076] In one embodiment of the present invention, R1 to R3 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; or a linear or branched alkyl group.

[0077] In one embodiment of the present invention, R1 to R3 are the same as or different from each other, and each independently is hydrogen; F; a methyl group; or a tert-butyl group.

[0078] In another embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0079] In one embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and each independently is any one of the following structures. In this case, the following structures may be further substituted with additional substituents.

[0080]

Chemical formula

[0081] In the above structure, W1 and W2 are the same as or different from each other, and each independently is O, S, NRa, CRbRc, or SiRdRe, R101 to R111, Ra, Rb, Rc, Rd, and Re are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, p1 is an integer from 1 to 7, p2, p4, and p5 are each an integer from 1 to 4, p3 and p6 are each an integer from 1 to 5, when p1 to p6 are each 2 or more, the substituents in parentheses are the same as or different from each other,

Chemical formula

[0082] In one embodiment of the present invention, the R101 to R111 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0083] In one embodiment of the present invention, the R101 to R111 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0084] In another embodiment, the R101 to R111 are the same as or different from each other, and each independently is hydrogen; deuterium; or a halogen group.

[0085] In another embodiment, the R101 to R111 are the same as or different from each other, and each independently is hydrogen; deuterium; or F.

[0086] In one embodiment of the present invention, the W1 and W2 are each O.

[0087] In one embodiment of the present invention, the W1 and W2 are each S.

[0088] In one embodiment of the present invention, the W1 and W2 are each CRbRc.

[0089] In one embodiment of the present invention, Rb and Rc are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0090] In one embodiment of the present invention, Rb and Rc are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0091] According to another embodiment, Rb and Rc are the same as or different from each other, and each independently is hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; or a substituted or unsubstituted phenyl group.

[0092] In one embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0093] In one embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and each independently is a phenyl group substituted or unsubstituted with deuterium, a halogen group, or an alkyl group; a biphenyl group substituted or unsubstituted with deuterium, a halogen group, or an alkyl group; a naphthyl group substituted or unsubstituted with deuterium, a halogen group, or an alkyl group; a fluorenyl group substituted or unsubstituted with deuterium, a halogen group, or an alkyl group; a dibenzofuran group substituted or unsubstituted with deuterium, a halogen group, or an alkyl group; or a dibenzothiophene group substituted or unsubstituted with deuterium, a halogen group, or an alkyl group.

[0094] In another embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently is a phenyl group which may or may not be substituted with a halogen group; a biphenyl group which may or may not be substituted with a halogen group; a naphthyl group which may or may not be substituted with a halogen group; a fluorenyl group which may or may not be substituted with a halogen group; a dibenzofuran group which may or may not be substituted with a halogen group; or a dibenzothiophene group which may or may not be substituted with a halogen group.

[0095] In another embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently is a phenyl group which may or may not be substituted with F; a biphenyl group which may or may not be substituted with F; a naphthyl group which may or may not be substituted with F; a fluorenyl group which may or may not be substituted with F; a dibenzofuran group which may or may not be substituted with F; or a dibenzothiophene group which may or may not be substituted with F.

[0096] In another embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently is a phenyl group which may or may not be substituted with F; or a dibenzofuran group which may or may not be substituted with F.

[0097] In one embodiment of the present invention, L11 and L12 are the same as or different from each other, and each independently is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0098] In one embodiment of the present invention, L11 and L12 are the same as or different from each other, and each independently is any one of the following structures. At this time, the following structures may be further substituted with additional substituents.

[0099]

Chemical formula

[0100] In the above structure, W11 to W22 are the same as or different from each other, and each independently is O, S, CRuRv, SiRwRx, or NRy. R201 to R207, Ru, Rv, Rw, Rx, Ry, Rs, and Rt are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. q1 to q5 are each an integer from 1 to 4. When q1 to q5 are 2 or more, the substituents in parentheses are the same as or different from each other.

Chemical formula

[0101] In one embodiment of the present invention, R201 to R207, Ru, Rv, Rw, Rx, Ry, Rs, and Rt are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0102] In another embodiment, R201 to R207, Ru, Rv, Rw, Rx, Ry, Rs, and Rt are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0103] In one embodiment of the present invention, L11 and L12 are the same as or different from each other, and each independently is any one of the following structures. At this time, the following structures may be further substituted with a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0104]

Chemical formula

[0105] In the above structure, R201 to R205 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, q1 to q5 are each an integer from 1 to 4, When q1 to q5 are 2 or more, the substituents in parentheses are the same as or different from each other,

Chemical formula

[0106] Also, according to one embodiment, L11 and L12 are the same as or different from each other, and each independently is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted fluorenylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted binaphthylene group; or a substituted or unsubstituted naphthylene group, or a group in which two or more of the above substituents are linked.

[0107] In one embodiment of the present invention, L11 and L12 are the same as or different from each other, and each independently is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted terphenylene group.

[0108] In one embodiment of the present invention, L11 and L12 are the same as or different from each other, and each independently is a substituted or unsubstituted biphenylene group.

[0109] In one embodiment of the present invention, the photocurable group or thermosetting group is any one of the following structures.

[0110]

Chemical formula

[0111] In the above structure, L50 to L55 are the same as or different from each other and are each independently a direct bond, -O-, or a substituted or unsubstituted alkylene group,

Chemical formula

[0112] In one embodiment of the present invention, the photocurable group or thermosetting group is any one of the following structures.

[0113]

Chemical formula

[0114] In the above structure, L54 is a direct bond or -O-,

Chemical formula

[0115] In one embodiment of the present invention, the photocurable group or thermosetting group is

Chemical formula

[0116] In one embodiment of the present invention, the photocurable group or thermosetting group is any one of the following structures.

[0117]

Chemical formula

[0118] In one embodiment of the present invention, the compound of Chemical formula 1 is any one of the following structures.

[0119]

Chemical formula

[0120]

Chem.

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Chem.

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Chem.

[0124]

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Chem.

[0126]

Chem.

[0127]

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[0128]

Chem.

[0129]

Chem.

[0130]

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[0131]

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[0132]

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[0133]

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[0134]

Chem.

[0135]

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[0136]

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[0137]

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[0138]

Chem.

[0139]

Chem.

[0140]

Chem.

[0141]

Chem.

[0142]

Chem.

[0143]

Chem.

[0144]

Chem.

[0145]

Chem.

[0146] In the above structure, hydrogen can be replaced by deuterium.

[0147] In one embodiment of the present invention, the compound is deuterated by 10% or more.

[0148] As used herein, "deuteration" means that the available hydrogen of a compound is replaced by deuterium.

[0149] As used herein, when deuterium is substituted at N%, it means that N% of the available hydrogen in the structure is replaced by deuterium. For example, when a phenyl group is 50% substituted by deuterium, it means that 3 out of 6 hydrogens of the phenyl group are replaced by deuterium.

[0150] As used herein, the degree of deuteration can be confirmed by known methods such as nuclear magnetic resonance spectroscopy ( 1 1H NMR) and GC / MS.

[0151] In one embodiment of the present invention, the compound is 10% to 100% deuterated.

[0152] In one embodiment of the present invention, the compound is 10% to 90% deuterated.

[0153] In one embodiment of the present invention, the compound is 20% or more deuterated.

[0154] In one embodiment of the present invention, the compound is 20% to 100% deuterated.

[0155] In one embodiment of the present invention, the compound is 20% to 80% deuterated.

[0156] The compound according to one embodiment of the present invention may be produced by the production method described below.

[0157] For example, the compound of Chemical Formula 1 may be produced with a core structure as shown in the following reaction formula. The substituents may be bonded by methods well known in the art, and the type, position, or number of the substituents may be changed by techniques well known in the art.

[0158]

Chemical formula

[0159] In the above reaction formula, L1 to L3, L11, L12, Ar1 to Ar4, X1 to X3, R1 to R3, R11 to R16, a1 to a3, n1 to n3, and n11 to n16 are the same as defined in Chemical Formula 1.

[0160] One embodiment of the present invention provides a coating composition containing the compound of Chemical Formula 1 described above.

[0161] In one embodiment of the present invention, the coating composition further comprises a solvent. In one embodiment of the present specification, the coating composition comprises the compound of Chemical Formula 1 and a solvent.

[0162] In one embodiment of the present invention, the coating composition may be liquid. The term "liquid" means being in a liquid state at normal temperature and normal pressure.

[0163] In one embodiment of the present invention, when the coating composition is applied to an organic layer, a solvent that does not dissolve the substance of the lower layer is used. Thereby, there is an advantage that the organic layer can be introduced by a solution process.

[0164] In one embodiment of the present invention, since the compound contains a photocurable group or a thermosettable group, the resistance to the solvent is improved during the heat treatment after coating. That is, since the compound cross-links after coating, it does not dissolve in a specific solvent.

[0165] For example, even if a coating composition is manufactured using a solvent that dissolves the compound and a layer is manufactured by a solution process, it can have resistance to the same solvent when cured by heat treatment.

[0166] Therefore, when a heat treatment process is performed after forming an organic layer using the compound, a solution process is possible when applying another organic layer.

[0167] For example, when the coating composition is applied to a hole injection layer, when manufacturing an upper layer (such as a hole transport layer), by using a specific solvent in which the cured coating composition shows resistance, there is an advantage that the upper layer can be introduced by a solution process.

[0168] 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 chlorinated solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; polyhydric alcohols and their derivatives such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol; alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents such as methyl benzoate, butyl benzoate, and 3-phenoxybenzoate; and solvents such as tetralin. However, any solvent that can dissolve or disperse the compound according to one embodiment of the present invention may be used, and the present invention is not limited thereto.

[0169] In one embodiment of the present invention, the solvent may be used alone or in combination of two or more solvents.

[0170] In one embodiment of the present invention, the coating composition further does not contain a p-doping substance.

[0171] In one embodiment of the present invention, the coating composition further contains a p-doping substance.

[0172] In this specification, the p-doping substance means a substance that makes the host substance have p-semiconductor characteristics. The p-semiconductor characteristics mean the characteristics of receiving or transporting holes at the HOMO (highest occupied molecular orbital) energy level, that is, the characteristics of a substance with high hole conductivity.

[0173] In one embodiment of the present invention, the p-doping substance may be represented by any one of the following chemical formulas A to H, but is not limited thereto.

[0174]

Chemical formula

[0175]

Chemical formula

[0176]

Chemical formula

[0177] In the present invention, the p-doping substance may be any substance that has p-semiconductor characteristics, and one kind or two or more kinds may be used, and the type thereof is not limited.

[0178] In one embodiment of the present invention, the content of the p-doping substance is 0 wt% to 500 wt% based on the compound of Chemical formula 1. Specifically, the content of the p-doping substance is 100 wt% to 400 wt% based on the compound of Chemical formula 1.

[0179] In one embodiment of the present invention, the p-doping substance is contained in an amount of 0 to 50% by weight based on the total solid content of the coating composition. In one embodiment of the present specification, the p-doping substance preferably contains 1 to 50% by weight based on the total solid content of the coating composition, and more preferably contains 10 to 30% by weight based on the total solid content of the coating composition.

[0180] In other embodiments, the coating composition further contains a single molecule containing a functional group crosslinkable by heat or light; or a single molecule containing a terminal group capable of forming a polymer by heat.

[0181] In one embodiment of the present invention, the single molecule containing a functional group crosslinkable by heat or light; or the single molecule containing a terminal group capable of forming a polymer by heat may be a compound having a molecular weight of 3,000 g / mol or less.

[0182] In one embodiment of the present invention, the single molecule containing a functional group crosslinkable by heat or light; or the single molecule containing a terminal group capable of forming a polymer by heat may be an aryl such as phenyl, biphenyl, fluorene, naphthalene; arylamine; or a single molecule substituted with a functional group crosslinkable by heat or light or a terminal group capable of forming a polymer by heat on fluorene.

[0183] In one embodiment of the present invention, the viscosity of the coating composition is 2 cP to 15 cP at room temperature. Specifically, the viscosity of the coating composition is 2 cP to 10 cP. When the above-described viscosity is satisfied, the manufacturing of the device is easy.

[0184] One embodiment of the present invention provides an organic light-emitting device formed using the coating composition.

[0185] One embodiment of the present invention provides an organic light-emitting device including a first electrode, a second electrode, and one or more organic layers including a light-emitting layer provided between the first electrode and the second electrode, wherein one or more of the organic layers include the coating composition or a cured product thereof. At this time, the cured product of the coating composition is a state in which the coating composition is cured by heat treatment or light treatment.

[0186] In one embodiment of the present invention, the organic layer including the coating composition or a cured product thereof is a hole transport layer or a hole injection layer.

[0187] In one embodiment of the present invention, the organic layer including the coating composition or a cured product thereof is an electron transport layer or an electron injection layer.

[0188] In one embodiment of the present invention, the organic layer including the coating composition or a cured product thereof is a light-emitting layer.

[0189] In one embodiment of the present invention, the organic layer including the coating composition or a cured product thereof is a light-emitting layer, and the light-emitting layer includes the compound of Chemical Formula 1 as a host of the light-emitting layer.

[0190] In one embodiment of the present invention, the organic layer including the coating composition or a cured product thereof is a light-emitting layer, and the light-emitting layer includes the compound of Chemical Formula 1 as a dopant of the light-emitting layer.

[0191] 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 performs hole transport and hole injection, and a layer that simultaneously performs electron transport and electron injection.

[0192] In one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.

[0193] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0194] In another embodiment, the organic light-emitting device may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0195] In another embodiment, the organic light-emitting device may be an organic light-emitting device having an inverted structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0196] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including, as the organic layer, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously performs hole transport and hole injection, a layer that simultaneously performs electron transport and electron injection, and the like. However, the structure of the organic light-emitting device is not limited thereto, and may further include a smaller number of organic layers.

[0197] For example, the structure of the organic light-emitting device according to an embodiment of the present invention is illustrated in FIG. 1.

[0198] FIG. 1 illustrates a structure of an organic light-emitting device in which an anode 201, a hole injection layer 301, a hole transport layer 401, a light-emitting layer 501, a layer 601 that simultaneously performs electron transport and electron injection, and a cathode 701 are sequentially stacked on a substrate 101.

[0199] FIG. 1 illustrates an organic light-emitting device, and the structure of the organic light-emitting device of the present invention is not limited thereto.

[0200] 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.

[0201] The organic light-emitting device of the present invention may be stacked in a structure as exemplified below. (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 / 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 / light-emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0202] In the above structure, the "electron transport layer / electron injection layer" may be replaced by an "electron transport and injection layer" or a "layer that simultaneously transports and injects electrons".

[0203] Also, in the above structure, the "hole injection layer / hole transport layer" may be replaced by a "hole injection and transport layer" or a "layer that simultaneously injects and transports holes".

[0204] The organic light-emitting device of the present invention may be manufactured by materials and methods well-known in the art, except that one or more of the organic layers are formed using the coating composition containing the compound of Chemical Formula 1.

[0205] For example, the organic light-emitting device of the present invention can be manufactured by sequentially depositing an anode, an organic layer, and a cathode on a substrate. At this time, a metal, a conductive metal oxide, or an alloy thereof is deposited on the substrate using a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation to form an anode, and then a hole injection layer, a hole transport layer, a light-emitting layer, and an organic layer including a layer that simultaneously transports and injects electrons are formed by a solution process, a deposition process, etc., and then a substance that can be used as a cathode is deposited thereon to manufacture the device. In addition to such a method, an organic light-emitting device can be manufactured by sequentially depositing an organic layer and an anode substance from a cathode substance on a substrate.

[0206] Also, this specification provides a method for manufacturing an organic light-emitting device formed using the coating composition.

[0207] Specifically, one embodiment of the present invention includes the steps of preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer, and the step of forming the organic layer includes the step of forming one or more organic layers using the coating composition.

[0208] In one embodiment of the present invention, the step of forming one or more organic layers using the coating composition employs a spin coating method.

[0209] In other embodiments, the step of forming one or more organic layers using the coating composition employs a printing method.

[0210] In one embodiment of the present invention, examples of the printing method include, but are not limited to, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing.

[0211] Due to its structural characteristics, the coating composition according to one embodiment of the present invention is suitable for solution processes and can be formed by a printing method, thus having the effect of being economical in terms of time and cost during the manufacture of elements.

[0212] In one embodiment of the present invention, the step of forming one or more organic layers using the coating composition includes the step of coating the coating composition on the first electrode; and the step of heat-treating or light-treating the coated coating composition.

[0213] 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.

[0214] In one embodiment of the present invention, the heat treatment time in the heat treatment step is 1 minute to 2 hours. According to one embodiment, it may be 1 minute to 1 hour, and according to another embodiment, it may be 30 minutes to 1 hour.

[0215] 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.

[0216] 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.

[0217] In one embodiment of the present invention, the other organic layer means an organic layer formed from other substances and does not contain the coating composition or a cured product thereof.

[0218] The step of coating the coating composition on the first electrode uses a solvent that does not dissolve the substance of the lower layer. For example, when the coating composition is applied to the hole transport layer, the coating composition contains a solvent that does not dissolve the substance of the lower layer (such as the first electrode, hole injection layer, etc.). Thereby, there is an advantage that the hole transport layer can be introduced by a solution process.

[0219] By the step of heat-treating or light-treating the coated coating composition, an organic layer including a structure in which a plurality of the compounds contained in the coating composition form crosslinks and are thinned can be provided. 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 dissolution, morphological influence, or decomposition by a solvent.

[0220] Therefore, when the organic layer formed using the coating composition is formed including a heat treatment or light treatment step, the resistance to a solvent increases, and solution vapor deposition and crosslinking methods can be repeatedly performed to form multiple layers, the stability increases, and the lifetime characteristics of the device can be increased.

[0221] In one embodiment of the present invention, as the anode material, a material having a large work function is generally preferred so that hole injection into the organic layer becomes smooth. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0222] In one embodiment of the present invention, as the cathode material, a material having a small work function is generally preferred so that electron injection into the organic layer becomes easy. Specific examples of the cathode material include metals such as barium, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; materials having a multilayer structure such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0223] In one embodiment of the present invention, the hole injection layer is a layer that injects holes from an electrode. As the hole injection material, a compound having the ability to transport holes, having an excellent hole injection effect at the anode, an excellent hole injection effect on the light-emitting layer or the light-emitting material, preventing the transfer of excitons generated from the light-emitting layer to the electron injection layer or the electron injection material, and having excellent thin film forming ability is preferable. Further, 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 the compound of Chemical Formula 1 described above, metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, and conductive polymers such as polyaniline and polythiophene, but are not limited thereto.

[0224] In one embodiment of the present invention, the hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport material is a material that can receive the transport of holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and a material having a high mobility with respect to holes is preferable. As specific examples of the hole transport material, arylamine-based organic substances, conductive polymers, and block copolymers in which both a conjugated part and a non-conjugated part are present may be used, but are not limited thereto. More specifically, a compound containing an arylamine group may be used for the hole transport layer.

[0225] In one embodiment of the present invention, the hole transport layer contains the compound of the following Chemical Formula HT-1.

Chemical formula

[0226] In the Chemical Formula HT-1, L201 is a substituted or unsubstituted arylene group, R201 to R204 are the same as or different from each other and are each independently hydrogen; deuterium; 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.

[0227] In one embodiment of the present invention, L201 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0228] In one embodiment of the present invention, L201 is an arylene group.

[0229] 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.

[0230] In one embodiment of the present invention, L201 is a phenylene group; a biphenylene group; or a naphthylene group.

[0231] In one embodiment of the present invention, L201 is a biphenylene group.

[0232] In one embodiment of the present invention, R201 to R204 are the same as or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0233] In one embodiment of the present invention, R201 to R204 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0234] In one embodiment of the present invention, R201 to R204 are the same as or different from each other and are each independently an aryl group.

[0235] In one embodiment of the present invention, R201 to R204 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0236] In one embodiment of the present invention, R201 to R204 are the same as or different from each other, and each independently is a phenyl group; a biphenyl group; or a naphthyl group.

[0237] In one embodiment of the present invention, the chemical formula HT-1 has the following structure. [Chemical Formula]

[0238] In one embodiment of the present invention, the light-emitting substance contained in the light-emitting layer is a substance that can emit light in the visible light region by receiving the transport of holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining them, and a substance with good quantum efficiency for fluorescence and phosphorescence is preferred. Specific examples include, but are not limited to, 8-hydroxyquinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole, and benzimidazole-based compounds; poly(p-phenylene vinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, etc.

[0239] In one embodiment of the present invention, the light-emitting layer may include a host material and a dopant material. Examples of the host material include condensed aromatic ring derivatives or heterocyclic ring-containing compounds. Specifically, examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto. More specifically, an anthracene derivative may be used as the host.

[0240] In one embodiment of the present invention, the host of the light-emitting layer contains a compound of the following chemical formula EH-1.

Chemical formula

[0241] In the chemical formula EH-1, L301 and L302 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heterocyclic group. Ar301 and Ar302 are the same as or different from each other, and each independently is 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 from 1 to 7, and when r301 is 2 or more, two or more R301s are the same as or different from each other.

[0242] In one embodiment of the present invention, L301 and L302 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted monocyclic arylene group; or a substituted or unsubstituted polycyclic arylene group.

[0243] In one embodiment of the present invention, L301 and L302 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0244] In one embodiment of the present invention, L301 and L302 are each a direct bond.

[0245] In one embodiment of the present invention, Ar301 and Ar302 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group.

[0246] In one embodiment of the present invention, Ar301 and Ar302 are the same as or different from each other, and each independently is a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

[0247] In one embodiment of the present invention, Ar301 and Ar302 are the same as or different from each other, and each independently is 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 triphenylene group; a substituted or unsubstituted pyrene group; or a substituted or unsubstituted fluorenyl group.

[0248] In one embodiment of the present invention, Ar301 and Ar302 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.

[0249] In one embodiment of the present invention, Ar301 and Ar302 are each a naphthyl group.

[0250] In one embodiment of the present invention, R301 is hydrogen.

[0251] In one embodiment of the present invention, the chemical formula EH-1 is any one of the following structures.

Chemical formula

[0252] In one embodiment of the present invention, examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and examples include pyrene, anthracene, chrysene, periflanthene having an arylamino group. The styrylamine compound is a compound in which at least one arylvinyl group is substituted for a substituted or unsubstituted arylamine, and 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, but not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include, but are not limited to, iridium complexes and platinum complexes. More specifically, a compound containing an arylamine group may be used as the dopant.

[0253] In one embodiment of the present invention, the dopant of the light-emitting layer contains a compound of the following chemical formula ED-1.

Chemical formula

[0254] In the chemical formula ED-1, L401 is a substituted or unsubstituted arylene group; or a substituted or unsubstituted alkenylene group, R401 to R404 are the same as or different from each other, and each independently is hydrogen; deuterium; 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, r401 is an integer from 1 to 10, When r401 is 2 or more, the structures in parentheses are the same as or different from each other.

[0255] In one embodiment of the present invention, the L401 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted alkenylene group having 2 to 30 carbon atoms.

[0256] In one embodiment of the present invention, the L401 is an arylene group; or an alkenylene group.

[0257] In one embodiment of the present invention, the L401 is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted vinylene group.

[0258] In one embodiment of the present invention, the L401 is a phenylene group; a biphenylene group; a naphthylene group; or a vinylene group.

[0259] In one embodiment of the present invention, R401 to R404 are the same as or different from each other, and each independently is 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.

[0260] In one embodiment of the present invention, R401 to R404 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0261] In one embodiment of the present invention, R401 to R404 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0262] In one embodiment of the present invention, R401 to R404 are the same as or different from each other, and each independently is a phenyl group substituted or unsubstituted with an alkyl group; a biphenyl group substituted or unsubstituted with an alkyl group; or a naphthyl group substituted or unsubstituted with an alkyl group.

[0263] In one embodiment of the present invention, R401 to R404 are the same as or different from each other, and each independently is a phenyl group substituted or unsubstituted with an alkyl group.

[0264] In one embodiment of the present invention, the chemical formula ED-1 has the following structure.

Chemical formula

[0265] In one embodiment of the present invention, the electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. The electron transport material is a material that can smoothly receive electron injection from the cathode and transfer it to the light-emitting layer, and a material with high mobility for electrons is preferable. Specific examples include, but are not limited to, an Al complex of 8-hydroxyquinoline; a complex containing Alq3; an organic radical compound; a hydroxyflavone-metal complex, etc. The electron transport layer may be used together with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are ordinary materials having a low work function and followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.

[0266] In one embodiment of the present invention, the electron injection layer is a layer that injects electrons from an electrode. As the electron injection material, a compound having the ability to transport electrons, excellent electron injection effects on the electron injection effect from the cathode and the light-emitting layer or light-emitting material, preventing the transfer of excitons generated from the light-emitting layer to the hole injection layer, and excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, benzimidazole, perylenetetracarboxylic acid, phenanthroline, fluorenylidenemethane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, etc. can be mentioned, but are not limited thereto.

[0267] In one embodiment of the present invention, examples of the metal complex compound include lithium 8-hydroxyquinolinate, zinc bis(8-hydroxyquinolinate), copper bis(8-hydroxyquinolinate), manganese bis(8-hydroxyquinolinate), aluminum tris(8-hydroxyquinolinate), aluminum tris(2-methyl-8-hydroxyquinolinate), gallium tris(8-hydroxyquinolinate), beryllium bis(10-hydroxybenzo[h]quinolinate), zinc bis(10-hydroxybenzo[h]quinolinate), gallium bis(2-methyl-8-quinolinato)chloride, gallium bis(2-methyl-8-quinolinato)(o-cresolato), aluminum bis(2-methyl-8-quinolinato)(1-naphtholato), gallium bis(2-methyl-8-quinolinato)(2-naphtholato), etc., but are not limited thereto.

[0268] In one embodiment of the present invention, the electron transport layer and the electron injection layer may be formed as a layer that simultaneously transports and injects electrons. At this time, any of the above-described electron transport materials and electron injection materials can be used as the material applied to the layer that simultaneously transports and injects electrons. For example, a phenanthroline-based compound may be used for the layer that simultaneously transports and injects electrons.

[0269] In one embodiment of the present invention, the layer that simultaneously performs electron transport and electron injection contains a compound of the following chemical formula ET-1. [Chemical formula]

[0270] In the chemical formula ET-1, R501 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, r501 is an integer from 1 to 8, When r501 is 2 or more, the substituents in parentheses are the same as or different from each other.

[0271] In one embodiment of the present invention, the R501 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0272] In one embodiment of the present invention, the R501 is hydrogen; deuterium; an alkyl group; or an aryl group.

[0273] In one embodiment of the present invention, the R501 is hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted biphenyl group.

[0274] In one embodiment of the present invention, the R501 is hydrogen; deuterium; a methyl group; an ethyl group; a propyl group; a butyl group; a phenyl group; a naphthyl group; or a biphenyl group.

[0275] In one embodiment of the present invention, the R501 is hydrogen; a methyl group; or a phenyl group.

[0276] In one embodiment of the present invention, the chemical formula ET-1 has the following structure. [Chemical formula]

[0277] In one embodiment of the present invention, the hole blocking layer is a layer that prevents holes from reaching the cathode, and may generally be formed under the same conditions as the hole injection layer. Specific examples of hole blocking substances include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like.

[0278] In one embodiment of the present invention, the electron blocking layer is a layer that prevents electrons from reaching the anode, and substances well-known in the art may be used.

[0279] The organic light-emitting device according to the present invention may be a top emission type, a bottom emission type, or a double-sided emission type depending on the materials used.

Examples

[0280] Hereinafter, examples will be given to specifically explain the present invention in detail. However, the examples according to the present invention may be modified into various different forms, and it should not be construed that the scope of the present invention is limited to the examples described below. The examples of the present invention are provided to more fully explain the present invention to those with average knowledge in the art.

[0281] <Synthesis Example> Synthesis Example 1

Chemical formula

[0282] Compound 1a (1.0 equiv.), Compound 1b (2.2 equiv.), sodium tert-butoxide (NaO t Bu) (3.0 equiv.) in toluene (Toluene) (NaO tThis was dissolved in a concentration of 0.2 M with respect to Compound 1a, then heated to 80 °C, replaced with a nitrogen atmosphere, and stirred for 30 minutes. Then, bis(tri-tert-butylphosphine)palladium(0), Pd(P t Bu3)2) (0.05 equiv.) was added and stirred for 3 hours. After evaporating toluene, crude was obtained by CH2Cl2 / H2O extraction, and Compound 1 was obtained by column purification with CH2Cl2. MS: [M+H] + =1783.3

[0283] Synthesis Example 2

Chemical Structure

[0284] Compound 2 was produced in the same manner as the production method of Synthesis Example 1, except that Compound 2a was used instead of Compound 1a and Compound 2b was used instead of Compound 1b. MS: [M+H] + =1799.2

[0285] Synthesis Example 3

Chemical Structure

[0286] Compound 3 was produced in the same manner as the production method of Synthesis Example 1, except that Compound 2a was used instead of Compound 1a and Compound 3b was used instead of Compound 1b. MS: [M+H] + =2095.6

[0287] Synthesis Example 4

Chemical Structure

[0288] Compound 4 was produced in the same manner as the production method of Synthesis Example 1, except that compound 2a was used instead of compound 1a and compound 4b was used instead of compound 1b in Synthesis Example 1. MS: [M+H] + =2019.3

[0289] Synthesis Example 5

Chemical Structure

[0290] Compound 5 was produced in the same manner as the production method of Synthesis Example 1, except that compound 5a was used instead of compound 1a and compound 5b was used instead of compound 1b in Synthesis Example 1. MS: [M+H] + =2037.7

[0291] Synthesis Example 6

Chemical Structure

[0292] Compound 6 was produced in the same manner as the production method of Synthesis Example 1, except that compound 6a was used instead of compound 1a and compound 5b was used instead of compound 1b in Synthesis Example 1. MS: [M+H] + =2389.7

[0293] Comparative Synthesis Example 1

Chemical Structure

[0294] Compound Z-1 was produced in the same manner as the production method of Synthesis Example 1, except that compound 7a was used instead of compound 1a in Synthesis Example 1. MS: [M+H] + =1565.0

[0295] Comparative Synthesis Example 2

Chemical Structure

[0296] In Synthesis Example 1, Compound Z-2 was produced in the same manner as the production method of Synthesis Example 1, except that Compound 8a was used instead of Compound 1a and Compound 5b was used instead of Compound 1b. MS: [M+H] + =2103.4

[0297] Comparative Synthesis Example 3

Chemical Structure

[0298] In Synthesis Example 1, Compound Z-3 was produced in the same manner as the production method of Synthesis Example 1, except that Compound 9a was used instead of Compound 1a and Compound 9b was used instead of Compound 1b. MS: [M+H] + =2081.8

[0299] Comparative Synthesis Example 4

Chemical Structure

[0300] In Synthesis Example 1, Compound Z-4 was produced in the same manner as the production method of Synthesis Example 1, except that Compound 10a was used instead of Compound 1a and Compound 9b was used instead of Compound 1b. MS: [M+H] + =1600.3

[0301] <Experimental Example 1. Measurement of Viscosity> Experimental Example 1-1 10 mg of Compound 1 produced in Synthesis Example 1 was dissolved in 0.32 g of purified toluene to have a concentration of 3 wt%, and then the viscosity was measured using a viscometer. As a result, a viscosity value of 4.8 cP was shown.

[0302] Experimental Example 1-2 In Experimental Example 1-1, the viscosity of Compound 2 was measured in the same manner as the method of Experimental Example 1-1, except that Compound 2 was used instead of Compound 1. As a result, a viscosity value of 3.7 cP was shown.

[0303] Experimental Example 1-3 In Experimental Example 1-1, except that Compound 3 was used instead of Compound 1, the viscosity of Compound 3 was measured in the same manner as in Experimental Example 1-1, and as a result, a viscosity value of 4.4 cP was shown.

[0304] Experimental Example 1-4 In Experimental Example 1-1, except that Compound 4 was used instead of Compound 1, the viscosity of Compound 4 was measured in the same manner as in Experimental Example 1-1, and as a result, a viscosity value of 6.2 cP was shown.

[0305] Experimental Example 1-5 In Experimental Example 1-1, except that Compound 5 was used instead of Compound 1, the viscosity of Compound 5 was measured in the same manner as in Experimental Example 1-1, and as a result, a viscosity value of 7.8 cP was shown.

[0306] Experimental Example 1-6 In Experimental Example 1-1, except that Compound 6 was used instead of Compound 1, the viscosity of Compound 6 was measured in the same manner as in Experimental Example 1-1, and as a result, a viscosity value of 5.1 cP was shown.

[0307] Comparative Example 1-1 In Experimental Example 1-1, except that the following Compound A was used instead of Compound 1, the viscosity of Compound A was measured in the same manner as in Experimental Example 1-1, and as a result, a viscosity value of 3.4 cP was shown.

[0308]

Chemical formula

[0309] Comparative Example 1-2 In Experimental Example 1-1, except that the following Compound B was used instead of Compound 1, the viscosity of Compound B was measured in the same manner as in Experimental Example 1-1, and as a result, a viscosity value of 14.2 cP was shown.

[0310]

Chemical formula

[0311] As a result of comparing the above Experimental Examples 1-1 to 1-6, Comparative Examples 1-1 and 1-2, it was confirmed that Compounds 1 to 6 synthesized in the above Synthesis Examples have a tendency similar to the viscosity of a single-molecular-weight compound as in Comparative Example 1-1.

[0312] <Experimental Example 2. Fabrication of Organic Light-Emitting Device> Experimental Example 2-1 A glass substrate with a thin film coating of ITO (indium tin oxide) having a thickness of 1,500 Å was placed in distilled water in which a detergent was dissolved and washed with ultrasonic waves. At this time, a detergent manufactured by Fischer Co. was used, and as the distilled water, distilled water secondarily filtered with a filter manufactured by Millipore Co. was used. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed with solvents of isopropyl alcohol and acetone, and after drying, the substrate was washed for 5 minutes, and then the substrate was transported to a glove box.

[0313] On the ITO transparent electrode prepared as described above, a 1.5 wt% cyclohexanone ink containing Compound 1 produced in Synthesis Example 1 described above and the following Compound P in a weight ratio of 8:2 (Compound 1:Compound P) was spin-coated on the ITO surface and heat-treated (cured) at 230 °C for 30 minutes to form a hole injection layer with a thickness of 30 nm. On the hole injection layer, a 2 wt% toluene ink of the following α-NPD compound was spin-coated to form a hole transport layer with a thickness of 40 nm. Then, after transferring to a vacuum evaporator, on the hole transport layer, the following ADN compound and the following DPAVBi compound were vacuum-evaporated to a thickness of 20 nm with a weight ratio (ADN:DPAVBi) of 20:1 to form a light-emitting layer. On the light-emitting layer, the following BCP compound was vacuum-evaporated to a thickness of 35 nm to form a layer that simultaneously performs electron transport and electron injection. On the layer that simultaneously performs electron transport and electron injection, LiF was sequentially evaporated to a thickness of 1 nm and aluminum was evaporated to a thickness of 100 nm to form a cathode.

[0314] [Chemical formula]

[0315] In the above process, the deposition rate of the organic matter was maintained at 0.4 Å / sec to 0.7 Å / sec, the deposition rate of lithium fluoride for the cathode was 0.3 Å / sec, and the deposition rate of aluminum was 2 Å / sec. The degree of vacuum during deposition was maintained at 2×10 -7 torr to 5×10 -6 torr.

[0316] Experimental Example 2-2 An organic light-emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 2 was used instead of Compound 1.

[0317] Experimental Example 2-3 An organic light-emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 3 was used instead of Compound 1.

[0318] Experimental Example 2-4 An organic light-emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 4 was used instead of Compound 1.

[0319] Experimental Example 2-5 An organic light-emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 5 was used instead of Compound 1.

[0320] Experimental Example 2-6 An organic light-emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 6 was used instead of Compound 1.

[0321] Comparative Example 2-1 An organic light-emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound Z-1 was used instead of Compound 1.

[0322] Comparative Example 2-2 An organic light-emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound Z-2 was used instead of Compound 1. Comparative Example 2-3 An organic light-emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound Z-3 was used instead of Compound 1.

[0323] Comparative Example 2-4 An organic light-emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound Z-4 was used instead of Compound 1.

[0324] The driving voltage, current efficiency, power efficiency, and luminance value of the organic light-emitting devices fabricated in Experimental Examples 2-1 to 2-6 and Comparative Examples 2-1 to 2-4 were measured at a current density of 10 mA / cm 2 , and the time (T95) at which the luminance reached 95% of the initial luminance (1000 nit) was measured. The results are shown in Table 1 below.

[0325]

Table 1

[0326] From Table 1, it can be confirmed that the organic light-emitting devices (Experimental Examples 2-1 to 2-6) to which the compounds according to the present invention are applied have a lower driving voltage, higher power efficiency, and excellent lifespan compared to the organic light-emitting devices (Comparative Examples 2-1 to 2-4) to which other compounds are applied. As described above, the preferred embodiment (hole injection layer) of the present invention has been explained. However, the present invention is not limited thereto and can be variously modified and implemented within the scope of the claims and the detailed description of the invention, and this also belongs to the scope of the invention.

Explanation of Reference Numerals

[0327] 101 ··· Substrate 201 ··· Anode 301 ··· Hole injection layer 401 ··· Hole transport layer 501 ··· Light-emitting layer 601 ··· Layer that simultaneously performs electron transport and electron injection 701 ··· Cathode

Claims

1. A compound of the following Chemical Formula 1: 【Chemical 1】 In the above Chemical Formula 1, L11 and L12 are the same as or different from each other and are each independently a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, Ar1 to Ar4 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, X1 to X3 are the same as or different from each other and are each independently a photocurable group or a thermosetting group, R1 to R3 and R11 to R16 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, a1 to a3 are each an integer of 1 to 3, When a1 to a3 are each 2 or more, the substituents in parentheses are the same as or different from each other, n1 to n3 are each an integer of 1 to 5, n11 and n16 are each an integer of 1 to 4, n12 to n15 are each an integer of 1 to 3, When n1 to n3 and n11 to n16 are each 2 or more, the substituents in parentheses are the same as or different from each other, The photocurable group or thermosetting group is any one of the following structures: 【Chemical 2】 In the above structure, L50 to L55 are the same as or different from each other and are each independently a direct bond; -O-; or a substituted or unsubstituted alkylene group, 【Chemical Formula 3】 is the bonding site to the above Chemical Formula 1; L1 to L3 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted phenylene group, However, when the photocurable group or thermosetting group is selected from the following structures of the above structures: 【Chemical 4】 (In the formula, L50 to L53 are as described above, and L54 and L55 are independently of each other -O- or a substituted or unsubstituted alkylene) L1 to L3 are independently a substituted or unsubstituted phenylene group, and also, When the photocurable group or thermosetting group is the following structure: 【Chemical Formula 5】 (In the formula, L54 and L55 are direct bonds) When selected from the groups having, L1 to L3 each represent a direct bond, Here, the term "substituted or unsubstituted" means being substituted with one or more substituents selected from the group consisting of deuterium; halogen groups; alkyl groups; cycloalkyl groups; alkoxy groups; aryloxy groups; amine groups; aryl groups; and heterocyclic groups, being substituted with a substituent in which two or more of the exemplified substituents are linked, or having no substituents.

2. The L11 and L12 are the same as or different from each other, and each independently is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, the compound according to Claim 1.

3. The Ar1 to Ar4 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, the compound according to Claim 1.

4. The chemical formula 1 is the following chemical formula 1-1 or 1-2, the compound according to Claim 1: 【Chemical Formula 6】 In the chemical formulas 1-1 and 1-2, R1 to R3, R11 to R16, L11, L12, Ar1 to Ar4, n1 to n3, and n11 to n16 are the same as the definitions in the chemical formula 1, L1' to L3' are the same as or different from each other, and each independently is a direct bond; or -O-, X1 to X3 are the same as or different from each other, and each independently is a photocurable group or a thermosetting group.

5. The chemical formula 1 is any one of the following structures, the compound according to Claim 1: 【Chemical Formula 7】 【Chemical Formula 8】 【Chemical Formula 9】 【Chemical Formula 10】 【Chemical 11】 【Chemical Formula 12】 【Chemical 13】 【Chemical Formula 14】 【Chemical Formula 15】 【Chemical 16】 【Chemical 17】 【Chemical Formula 18】 【Chemical Formula 19】 【Chemical 20】 【Chemical Formula 21】 【Chemical 22】 【Chemical 23】 【Chemical 24】 【Chemical 25】 【Chemical 26】 【Chemical 27】 【Chemical 28】 【Chemical Formula 29】 ​ 【Chemical 31】 【Chemical 32】 【Chemical 33】

6. A coating composition containing the compound according to any one of Claims 1 to 5.

7. A first electrode; A second electrode; and One or more organic layers including a light-emitting layer provided between the first electrode and the second electrode including, One or more of the organic layers contain the coating composition according to Claim 6 or a cured product thereof, an organic light-emitting device.

8. The organic layer containing the coating composition or a cured product thereof is a hole transport layer or a hole injection layer, the organic light-emitting device according to Claim 7.

9. The step of preparing a substrate; The step of forming a first electrode on the substrate; The step of forming one or more organic layers on the first electrode; and The step of forming a second electrode on the organic layer including, The step of forming the organic layer includes the step of forming one or more organic layers using the coating composition according to claim 6, a method for manufacturing an organic light-emitting device.

10. The step of forming one or more organic layers using the coating composition includes coating the coating composition on the first electrode; and heat-treating or light-treating the coated coating composition The method for manufacturing an organic light-emitting device according to claim 9, including.

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