Ink composition, organic layer containing the same, and organic light-emitting device containing the same

Abstract

The present invention relates to an ink composition, an organic layer containing the ink composition, and an organic light-emitting device containing the ink composition.

Description

[Technical Field]

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2021-0122564, filed with the Korean Intellectual Property Office on September 14, 2021, the entire contents of which are incorporated herein by reference. The present invention relates to an ink composition, an organic layer containing the ink composition, and an organic light-emitting device containing the ink composition. [Background technology]

[0002] Organic light-emitting devices are an example of a device in which electric current is converted into visible light through internal processes in specific organic molecules. The principle of organic light-emitting devices is as follows: When an organic layer is placed between an anode and a cathode and an electric current is passed between the two electrodes, electrons and holes are injected into the organic layer from the cathode and anode, respectively. The injected electrons and holes recombine to form excitons, which then fall back to the ground state and emit light. Organic light-emitting devices that utilize this principle typically consist of a cathode and an anode and organic layers positioned between them, such as a hole-injection layer, a hole-transport layer, an emitting layer, an electron-injection layer, an electron-transport layer, an electron-blocking layer, and a hole-blocking layer.

[0003] Conventionally, a deposition process has been mainly used to manufacture organic light emitting devices. However, manufacturing organic light emitting devices using a deposition process has problems such as a large amount of material loss and difficulty in manufacturing large-area devices. To solve these problems, devices using a solution process are being developed.

[0004] Therefore, there is a need for development of solution processable materials. Summary of the Invention [Problem to be solved by the invention]

[0005] The present invention relates to an ink composition, an organic layer containing the ink composition, and an organic light-emitting device containing the ink composition. [Means for solving the problem]

[0006] One embodiment of the present invention provides an ink composition comprising a compound represented by the following Chemical Formula 1 and a solvent represented by the following Chemical Formula A: [ka]

[0007] In the above Chemical Formula 1 and A, Y is O, S, CRaRb, or SiRcRd; Cy1 and Cy2 are the same or different and each independently represent a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring; Ra, Rb, Rc and Rd are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or are bonded to adjacent groups to form a substituted or unsubstituted ring; L1 to L3 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted arylene group; L11 and L12 are the same or different and each independently represent a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group; X1 and X2 are the same or different and each independently represents a curable group; R1 and R2 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; R3 and R4 are the same or different and each independently represent hydrogen; deuterium; 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; a, b, and c are each 0 or 1, n1 and n2 are each an integer of 0 to 7, and when n1 and n2 are each 2 or more, the two or more substituents in parentheses are the same or different. m1 and m2 are each an integer of 1 to 5, n3 and n4 are each an integer of 0 to 4, m1+n3 is 5 or less, and m2+n4 is 5 or less; Y1 to Y10 are the same or different and each independently represent hydrogen, deuterium, a hydroxy group, an ether group, a carbonyl group, an ester group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted amine group.

[0008] Another embodiment of the present invention provides a pixel comprising an ink composition or a cured version thereof.

[0009] Another embodiment of the present invention provides an organic layer comprising the pixel.

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

[0011] The ink composition according to an embodiment of the present invention can be used as a material for an organic layer of an organic light-emitting device, and can provide a device having low driving voltage, excellent luminous efficiency, and long life characteristics. The ink composition is solution processable and can be used to increase the area of ​​the device.

[0012] An organic layer including an ink composition according to an embodiment of the present invention has excellent flatness properties. [Brief explanation of the drawings]

[0013] [Figure 1]1 shows an organic light-emitting device according to one embodiment of the present invention. [Figure 2] 1 shows a line bank inkjet substrate onto which an ink composition according to one embodiment of the present invention is applied. [Figure 3] 1 shows an ink composition according to one embodiment of the present invention being applied to a line bank inkjet substrate. [Figure 4] 1 shows an ink composition according to one embodiment herein formed as a thin film on a line bank inkjet substrate. [Figure 5] 10 shows the thickness of a pixel according to Example 6 of the present invention. [Figure 6] 16 shows the thickness of a pixel according to a sixteenth embodiment of the present invention. [Figure 7] 10 shows the pixel thickness according to Comparative Example 5 of the present invention. [Figure 8] 10 shows the pixel thickness according to Comparative Example 10 of the present invention. [Figure 9] 10 shows the pixel thickness according to Comparative Example 15 of the present invention. [Figure 10] 10 shows the pixel thickness according to Comparative Example 27 of the present invention. [Figure 11] 36 shows the pixel thickness according to Example 36 of the present invention. [Figure 12] 40 shows the pixel thickness according to Example 40 of the present invention. [Figure 13] 10 shows the pixel thickness according to Comparative Example 29 of the present invention. [Figure 14] 10 shows the pixel thickness according to Comparative Example 30 of the present invention. [Figure 15] 10 shows the pixel thickness according to Comparative Example 31 of the present invention. [Figure 16] 10 shows the pixel thickness according to Comparative Example 32 of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0014] The present invention will be described in detail below.

[0015] One embodiment of the present invention provides an ink composition comprising a compound represented by the following Chemical Formula 1 and a solvent represented by the following Chemical Formula A: [ka]

[0016] In the above Chemical Formula 1 and A, Y is O, S, CRaRb, or SiRcRd; Cy1 and Cy2 are the same or different and each independently represent a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring; Ra, Rb, Rc and Rd are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or are bonded to adjacent groups to form a substituted or unsubstituted ring; L1 to L3 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted arylene group; L11 and L12 are the same or different and each independently represent a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group; X1 and X2 are the same or different and each independently represents a curable group; R1 and R2 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; R3 and R4 are the same or different and each independently represent hydrogen; deuterium; 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; a, b, and c are each 0 or 1, n1 and n2 are each an integer of 0 to 7, and when n1 and n2 are each 2 or more, the two or more substituents in parentheses are the same or different. m1 and m2 are each an integer of 1 to 5, n3 and n4 are each an integer of 0 to 4, m1+n3 is 5 or less, and m2+n4 is 5 or less; Y1 to Y10 are the same or different and each independently represent hydrogen, deuterium, a hydroxy group, an ether group, a carbonyl group, an ester group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted amine group.

[0017] The compound represented by Chemical Formula 1 according to one embodiment of the present invention contains two different types of substituents, specifically a haloaryl group and a curable group, and an amine group containing three or more rings, thereby suppressing radical formation at the corresponding position, increasing the stability of the compound and providing a high HOMO (highest occupied molecular orbital) energy level and excellent hole mobility. Therefore, when the compound represented by Chemical Formula 1 is contained in a hole injection layer in an organic light emitting device, it facilitates hole injection from the hole injection layer to the hole transport layer, thereby providing an organic light emitting device characterized by a long lifespan, which has a significant impact on improving the lifespan of the device.

[0018] The solvent represented by Formula A according to one embodiment of the present invention contains a biphenyl as a core structure, thereby exhibiting excellent solubility for aromatic solutes contained in the ink composition. Furthermore, the solvent has an excellent leveling effect, which reduces thickness variations between pixels and improves the uniformity of the organic layer. Specifically, the ink composition can reduce thickness variations between pixels after application, drying, and heat treatment. This reduces factors that affect the interference conditions of light emitted by a light-emitting device due to its thickness, thereby enabling the expectation of excellent light emission and / or color development.

[0019] In the present invention, when a member (layer) is said to be located "on" another member (layer), this includes not only the case where a member (layer) is in contact with the other member, but also the case where the other member (layer) exists between two members (layers).

[0020] In the present invention, when a part is said to "comprise" a certain component, this does not mean that it excludes other components, but that it may further include other components, unless otherwise specified.

[0021] In the present invention, the term "layer" is interchangeable with the term "film" commonly used in this technical field and refers to a coating that covers a desired area. The size of the "layer" is not limited, and each "layer" may be the same or different in size. According to one embodiment, the size of the "layer" may be the same as the entire device, may correspond to the size of a specific functional area, or may be smaller by a single sub-pixel.

[0022] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which this invention belongs. Methods and materials similar or equivalent to those described herein may be used to practice or test embodiments of the present invention, and suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, and in the event of a conflict, the present invention, including definitions, will prevail unless a specific passage is mentioned. Furthermore, the materials, methods, and examples are merely illustrative and not intended to be limiting.

[0023] In the present invention, the term "combination thereof" contained in the expression of a chemical formula in Markush format means a mixture or combination of one or more components selected from the group consisting of components described in Markush format, and means containing at least one component selected from the group consisting of the components.

[0024] Examples of the substituents in the present invention are described below, but are not limited thereto.

[0025] In the present invention, [ka] and [ka] means the site to be linked.

[0026] In the present invention, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution position is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different.

[0027] In the present invention, the term "substituted or unsubstituted" means that the group is substituted with at least one substituent selected from the group consisting of hydrogen, deuterium, a halogen group, an amine group, an alkyl group, an aryl group, and a heteroaryl group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked together, or has no substituents.

[0028] In the present invention, the linkage of two or more substituents means that a hydrogen atom of one of the substituents is linked to another substituent. For example, an isopropyl group and a phenyl group are linked to each other. [ka] or [ka] can be a substituent of

[0029] In the present invention, the linking of three substituents includes not only the case where (substituent 1)-(substituent 2)-(substituent 3) are consecutively linked, but also the case where (substituent 1) is linked to (substituent 2) and (substituent 3). For example, two phenyl groups and an isopropyl group are linked to form a [ka] or [ka] The case where four or more substituents are connected also includes the same cases as those described above.

[0030] In the present invention, a halogen group is a fluoro group (-F), a chloro group (-Cl), a bromo group (-Br) or an iodo group (-I).

[0031] In the present invention, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30; 1 to 20; 1 to 10; or 1 to 5. Specific examples include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc. The alkyl group may include a haloalkyl group, which is an alkyl group substituted with a halogen group. A specific example is a methyl group substituted with three fluoro groups, ie, a trifluoromethyl group, but is not limited to this.

[0032] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl, but are not limited to these.

[0033] In the present invention, the term "aryl group" refers to a monovalent group of a monovalent aromatic hydrocarbon or aromatic hydrocarbon derivative. In the present invention, the term "aromatic hydrocarbon" refers to a compound containing a ring in which π electrons are completely conjugated and planar, and the term "group derived from an aromatic hydrocarbon" refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed with an aromatic hydrocarbon. Furthermore, in the present invention, the term "aryl group" refers to a monovalent group in which at least two aromatic hydrocarbons or aromatic hydrocarbon derivatives are linked to each other. The aryl group is not particularly limited, but preferably has 6 to 60, 6 to 50, 6 to 30, 6 to 25, 6 to 20, 6 to 18, 6 to 15, 6 to 13, or 6 to 12 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group.

[0034] The monocyclic aryl group is not particularly limited, but preferably has 6 to 60, 6 to 54, 6 to 48, 6 to 42, 6 to 36, 6 to 30, 6 to 24, 6 to 18, or 6 to 12 carbon atoms, and specifically may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, or the like.

[0035] The polycyclic aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, 6 to 45 carbon atoms, 6 to 30 carbon atoms, 6 to 22 carbon atoms, 6 to 20 carbon atoms, 6 to 18 carbon atoms, 6 to 16 carbon atoms, 6 to 15 carbon atoms, 6 to 14 carbon atoms, 6 to 13 carbon atoms, 6 to 12 carbon atoms, or 6 to 10 carbon atoms, and may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenylenyl group, a chrysenyl group, a fluorenyl group, or the like.

[0036] In the present invention, the aryl group may include a haloaryl group substituted with a halogen group. The haloaryl group refers to an aryl group substituted with one or more halogen groups, and the haloaryl group may be an aryl group substituted with one or more substituents selected from the group consisting of a fluoro group, a chloro group, a bromo group, and an iodo group. The haloaryl group may also be substituted with two or more of the same halogen groups, for example, an aryl group substituted with one fluoro group or an aryl group substituted with two or more fluoro groups.

[0037] In the present invention, the term "heteroaryl group" refers to a monovalent aromatic heterocycle. Here, the term "aromatic heterocycle" refers to a monovalent group of an aromatic ring or a derivative of an aromatic ring, containing at least one heteroatom selected from the group consisting of N, O, P, S, Si, and Se. The aromatic ring derivative includes all structures in which an aromatic ring or an aliphatic ring is condensed with an aromatic ring. Furthermore, in the present invention, the term "heteroaryl group" refers to a monovalent group in which two or more aromatic rings containing heteroatoms or derivatives of aromatic rings containing heteroatoms are linked to each other. The heteroaryl group preferably has 2 to 60, 2 to 50, 2 to 30, 2 to 20, 2 to 18, or 2 to 13 carbon atoms. Examples of heteroaryl groups include, but are not limited to, thiophene, furanyl, pyrrole, imidazole, thiazole, oxazole, pyridine, pyrimidine, triazine, triazole, acridine, pyridazine, pyrazine, quinoline, quinazoline, quinoxaline, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuran, phenanthrolinyl, and dibenzofuran.

[0038] In the present invention, the heteroaryl group may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a fused aromatic and aliphatic ring.

[0039] In the present invention, the heterocyclic group refers to a monovalent group of an aliphatic ring, an aliphatic ring derivative, an aromatic ring, or an aromatic ring derivative, and includes one or more heteroatoms selected from the group consisting of N, O, P, S, Si, and Se.

[0040] In the present invention, the aliphatic ring is a non-aromatic hydrocarbon ring, examples of which include the above-mentioned cycloalkyl group and adamantyl group.

[0041] In the present invention, the aromatic ring may be the same as that described above for the aryl group.

[0042] In the present invention, the hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a fused ring of an aromatic ring with an aliphatic ring. Examples of the fused ring of an aromatic ring with an aliphatic ring include, but are not limited to, a 1,2,3,4-tetrahydronaphthalene group and a 2,3-dihydro-1H-indene group.

[0043] In the present invention, the above description of the heterocyclic group is applicable, except that the heterocyclic group is a divalent group.

[0044] In the present invention, the term "adjacent groups" refers to a substituent substituted on an atom directly linked to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring can be interpreted as "adjacent groups" to each other.

[0045] In the present invention, the curable group can cause a polymerization or crosslinking reaction, thereby causing a reaction to increase the molecular weight, and includes a thermosetting group that cures with heat, a photocurable group that cures with light, etc. The curable group is any one selected from the group consisting of the following structures, but is not limited to the following structures: [ka]

[0046] In the above structure: Lc1 is a direct bond; —O—; —S—; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; lc is 1 or 2, When the lc is 2, the Lc1 are the same or different from each other; Rc1 is a substituted or unsubstituted alkyl group; [ka] is the site that binds to Chemical Formula 1.

[0047] According to one embodiment of the present invention, Lc1 is a direct bond; a methylene group; or an ethylene group.

[0048] According to another embodiment of the present invention, Lc1 is a direct bond.

[0049] According to one embodiment of the present invention, Rc1 is a methyl group; or an ethyl group.

[0050] According to another embodiment of the present invention, Rc1 is a methyl group.

[0051] The compound represented by Chemical Formula 1 will be specifically described below.

[0052] According to one embodiment of the present invention, the above-mentioned Formula 1 is represented by the following Formula 11: [ka]

[0053] In the above Chemical Formula 11, The definitions of L1 to L3, L11, L12, X1, X2, R1 to R4, Y, Cy1, Cy2, a, b, c, n1 to n4, m1 and m2 are the same as those in Chemical Formula 1.

[0054] According to one embodiment of the present invention, the L1 to L3 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0055] According to another embodiment, L1 to L3 are the same or different and each independently represent a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0056] According to another embodiment, L1 and L2 are each a direct bond.

[0057] In yet another embodiment, L3 is a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0058] According to one embodiment of the present invention, the chemical formula 1 is represented by any one of the following chemical formulas 12 to 14. [ka] [ka]

[0059] In the chemical formulas 12 to 14, L11, L12, X1, X2, R1 to R4, Cy1, Cy2, Y, n1 to n4, m1, and m2 are defined as in Chemical Formula 1. R21 and R22 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; m21 is an integer of 0 to 4, m22 is an integer of 0 to 6, and when m21 and m22 are each an integer of 2 or more, the two or more substituents in parentheses are the same or different.

[0060] According to one embodiment of the present invention, said Y is O, S, CRaRb or SiRcRd.

[0061] According to one embodiment of the present invention, Ra, Rb, Rc, and Rd are the same or different from each other and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or are bonded to adjacent groups to form a substituted or unsubstituted ring.

[0062] According to another embodiment, Ra, Rb, Rc, and Rd are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; 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, or are bonded to adjacent groups to form a substituted or unsubstituted ring having 3 to 30 carbon atoms.

[0063] According to yet another embodiment, Ra, Rb, Rc and Rd are the same or different and each independently represent a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

[0064] According to one embodiment of the present invention, Cy1 and Cy2 are the same or different and each independently represent a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring.

[0065] In one embodiment of the present invention, Cy1 and Cy2 are the same or different and each independently have one of the following structures: [ka]

[0066] In the above structure: R11 to R13 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; m11 is an integer of 0 to 4, m12 and m13 are each an integer of 0 to 6, and when m1 to m3 are each an integer of 2 or more, the two or more substituents in parentheses are the same or different from each other, In the above structure: [ka] indicates the position to be bound.

[0067] According to one embodiment of the present invention, R11 to R13 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; 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.

[0068] In another embodiment, R11 to R13 are each hydrogen.

[0069] According to one embodiment of the present invention, m11 to m13 are each 0 or 1.

[0070] According to one embodiment of the present invention, R1 and R2 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; 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.

[0071] In another embodiment, R1 and R2 are each hydrogen.

[0072] According to one embodiment of the present invention, R3 and R4 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; 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.

[0073] In another embodiment, R3 and R4 are the same or different and each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

[0074] According to another embodiment, R3 and R4 are the same or different and each independently represent hydrogen; a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

[0075] According to another embodiment, R3 and R4 are the same or different and each independently represent a hydrogen atom; a methyl group; or a phenyl group.

[0076] According to one embodiment of the present invention, n1 and n2 are each 0 or 1.

[0077] In one embodiment of the present invention, R21 and R22 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; 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.

[0078] According to another embodiment, R21 and R22 are each hydrogen.

[0079] According to one embodiment of the present invention, the above-mentioned Chemical Formula 1 can be represented by any of the following compounds: [ka]

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

[0080] The compound of Formula 1 according to one embodiment of the present invention may have a core structure prepared according to the following Reaction Scheme 1. Each substituent may be attached by a method known in the art, and the type, position, or number of the substituent may be changed according to a technique known in the art. [ka]

[0081] The reaction is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the amine substitution reaction can be varied as known in the art.

[0082] The solvent represented by chemical formula A will be specifically described below.

[0083] According to one embodiment of the present invention, Y1 to Y10 are the same or different and each independently represent hydrogen; deuterium; a hydroxy group; an ether group; a carbonyl group; an ester group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted cycloalkenyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted amine group.

[0084] According to one embodiment of the present invention, Y1 to Y10 are the same or different and each independently represent hydrogen; deuterium; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted cycloalkenyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted amine group.

[0085] According to one embodiment of the present invention, Y1 to Y10 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

[0086] According to one embodiment of the present invention, Y1 to Y10 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms.

[0087] According to one embodiment of the present invention, Y1 to Y10 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms; or a substituted or unsubstituted alkoxy group having 1 to 8 carbon atoms.

[0088] According to one embodiment of the present invention, Y1 to Y10 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; or a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms.

[0089] According to one embodiment of the present invention, Y1 to Y10 are the same or different and each independently represent hydrogen; deuterium; an alkyl group; or an alkoxy group.

[0090] According to one embodiment of the present invention, Y1 to Y10 are the same or different and each independently represent 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 pentyl group; a substituted or unsubstituted hexyl group; a substituted or unsubstituted isopropyl group; a substituted or unsubstituted isobutyl group; a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted methoxy group; a substituted or unsubstituted ethoxy group; a substituted or unsubstituted propoxy group, or a substituted or unsubstituted butoxy group.

[0091] According to one embodiment of the present invention, Y1 to Y10 are the same or different and each independently represent hydrogen, deuterium, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a methoxy group, an ethoxy group, a propoxy group, or a butoxy group.

[0092] According to one embodiment of the present invention, Y1 to Y10 are the same or different and each independently represent hydrogen, deuterium, an ethyl group, a propyl group, a butyl group, a pentyl group, an isopropyl group, or a methoxy group.

[0093] In one embodiment of the present invention, the solvent represented by the chemical formula A has any of the following structures: [ka]

[0094] In the above structure, Y1 to Y10 are the same or different and each independently represent a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

[0095] According to a preferred embodiment of the present invention, the solvent represented by the chemical formula A is any one or a mixture of two or more selected from the group consisting of the following compounds: [ka]

[0096] According to a preferred embodiment of the present invention, the solvent represented by the chemical formula A is any one selected from the group consisting of the above compounds.

[0097] According to one embodiment of the present invention, the solvent represented by the chemical formula A is any one or a mixture of two or more selected from the group consisting of 3-isopropylbiphenyl, 3-methoxybiphenyl, 3-ethylbiphenyl, 4-butylbiphenyl, and 4-pentylbiphenyl.

[0098] According to one embodiment of the present invention, the surface tension of the solvent represented by the chemical formula A is 33 mN / m to 37 mN / m; or 33.5 mN / m to 36.5 mN / m.

[0099] According to one embodiment of the present invention, by controlling the surface tension of the solvent represented by Chemical Formula A, the surface tension range between other substances other than the solvent represented by Chemical Formula A can be easily adjusted. Specifically, the substances (e.g., additional solvents, other organic solvents, etc.) contained in the ink composition used in solution processing should generally be composed of substances that cause the ink composition to have a surface tension in the range of 25 mN / m to 45 mN / m, and it is desirable that the difference in surface tension between the substances be small. A surface tension in the range of 33 mN / m to 37 mN / m is in the middle of the preferred surface tension range. By having the solvent represented by Chemical Formula A have a surface tension in the range of 33 mN / m to 37 mN / m, the influence of the difference in surface tension between other substances other than the solvent represented by Chemical Formula A can be adjusted to be small. A small influence of the difference in surface tension between other substances other than the solvent represented by Chemical Formula A has the advantage of excellent flatness of the organic layer and uniformity of the pixel thickness of an organic light-emitting device manufactured by solution processing.

[0100] According to one embodiment of the present invention, the boiling point of the solvent represented by the chemical formula A is 220°C to 350°C; 250°C to 330°C; or 265°C to 315°C.

[0101] By including the solvent represented by Chemical Formula A having a boiling point within this range, excellent flatness of the organic material layer and / or pixel thickness uniformity can be expected when fabricating an organic material layer of an organic light-emitting device through solution processing. Specifically, the solvent represented by Chemical Formula A has the lowest vapor pressure of the constituent solvents and is not removed during the initial drying process, which has the advantage of being able to adjust the difference in surface tension between materials remaining after the initial drying process. As a result, excellent flatness of the organic material layer of an organic light-emitting device and / or pixel thickness uniformity can be expected.

[0102] The ink composition according to one embodiment of the present invention further comprises an ionic compound having an anionic group represented by the following Chemical Formula 2.

[0103] The ionic compound containing an anionic group represented by the following chemical formula 2 will be specifically described below. [ka]

[0104] In the above Chemical Formula 2, At least one of R201 to R220 is F; a cyano group; or a substituted or unsubstituted fluoroalkyl group; At least one of the remaining R201 to R220 is a curable group, The remaining R201 to R220 are the same or different and each independently represent hydrogen; deuterium; a nitro group; -C(O)R220'; -OR221; -SR222; -SO3R223; -COOR224; -OC(O)R225; -C(O)NR226R227; a substituted or unsubstituted alkyl group; a substituted or unsubstituted fluoroalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; R220' and R221 to R227 are the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0105] According to one embodiment of the present invention, the ink composition further comprises an ionic compound having an anionic group represented by Chemical Formula 2. Hereinafter, the compound represented by Chemical Formula 2 may be referred to as an anionic group compound.

[0106] Unlike an ionic compound containing an anionic group represented by Chemical Formula 2 (hereinafter referred to as an anionic group compound) having a curable group introduced therein according to one embodiment of the present invention, if no curable group is introduced, the ionic compound will not be cured, resulting in deterioration of device characteristics due to the ionic compound's migration between electrodes or layers. Furthermore, as the number of curable groups increases, the curing rate of the ionic compound or a composition containing it increases, improving film retention.

[0107] In one embodiment of the present invention, the anionic compound represented by Chemical Formula 2 has one curable group.

[0108] In one embodiment of the present invention, the number of curable groups in the anionic compound represented by Chemical Formula 2 is two.

[0109] In one embodiment of the present invention, the anionic compound represented by Chemical Formula 2 has four curable groups.

[0110] In one embodiment of the present invention, the anionic compound represented by Chemical Formula 2 has 16 to 19 F, cyano groups, or substituted or unsubstituted fluoroalkyl groups.

[0111] In one embodiment of the present invention, the amount of F in the anionic group compound is 15 to 50 parts by weight relative to 100 parts by weight of the anionic group compound.

[0112] In one embodiment of the present invention, the amount of F in the anionic group compound is 10 parts by weight to 45 parts by weight or less relative to 100 parts by weight of the anionic group compound.

[0113] In one embodiment of the present invention, the anionic group compound contains 8 to 20 F atoms per 100 parts by weight of the anionic group compound.

[0114] As described above, when the proportion of F, cyano groups, or fluoroalkyl groups in the molecule increases, the film retention rate during heat treatment improves.

[0115] According to one embodiment of the present invention, the ionic compound can be used in a hole injection layer of an organic light emitting device, and when used in the hole injection layer, it can be used as a dopant. In this case, as the F content of the ionic compound increases, the ability to attract electrons from other compounds (host compounds) increases, and holes are more efficiently generated in the host, improving performance in the hole injection layer.

[0116] According to one embodiment of the present invention, the F content can be determined by analysis using a COSA AQF-100 combustion furnace coupled to a Dionex ICS 2000 ion-chromatograph or by F NMR, a method commonly used for F analysis.

[0117] In one embodiment of the present invention, at least one benzene ring among the benzene rings containing R201 to R205, the benzene rings containing R206 to R210, the benzene rings containing R211 to R215, and the benzene rings containing R216 to R220 in Chemical Formula 2 is selected from the following structural formulas. [ka]

[0118] According to one embodiment of the present invention, the anionic group represented by Chemical Formula 2 is represented by any one selected from the group consisting of the following chemical formulas: [ka] [ka] [ka]

[0119] In the above chemical formula: n is an integer from 1 to 3, m is an integer from 1 to 3, and m+n=4; q is an integer of 0 to 3, r is an integer of 1 to 4, and q+r=4; Z is deuterium; a halogen group; a nitro group; a cyano group; an amino group; -C(O)R220'; -OR221; -SR222; -SO3R223; -COOR224; -OC(O)R225; -C(O)NR226R227; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; l is an integer of 1 to 4, and when l is 2 or more, Zs are the same or different; R220' and R221 to R227 are the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0120] The ionic compound containing a cationic group will be specifically described below.

[0121] According to one embodiment of the present invention, the ink composition further comprises a cationic group. Specifically, the ink composition further comprises an ionic compound comprising an anionic group and a cationic group represented by the above-mentioned Chemical Formula 2. As another example, the ink composition comprises an ionic compound, and the ionic compound comprises an anionic group and a cationic group represented by the above-mentioned Chemical Formula 2.

[0122] According to one embodiment of the present invention, the cationic group is any one of a monovalent cationic group; a group consisting of an onium compound; and a cationic group selected from the following structural formulas: [ka]

[0123] In the above structural formula, X1~X 76are the same or different and each independently represent hydrogen; deuterium; a cyano group; a nitro group; a halogen group; -COOR224; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted fluoroalkyl group; a substituted or unsubstituted aryl group; or a curable group; R224 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group; p is an integer from 0 to 10, a1 is 1 or 2, b1 is 0 or 1, and a1+b1=2.

[0124] According to one embodiment of the present invention, the monovalent cationic group may be an alkali metal cation, and the alkali metal cation is Na + , Li + , K. + These include, but are not limited to:

[0125] According to one embodiment of the present invention, the cationic group is a group consisting of an onium compound; or any cationic group selected from the above structural formulas.

[0126] According to one embodiment of the present invention, the cationic group is represented by any one of the following chemical formulas 310 to 315. [ka] [ka]

[0127] In the chemical formulas 310 to 315, X 100 ~X 142 are the same or different and each independently represent hydrogen; deuterium; a cyano group; a nitro group; a halogen group; -COOR224; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted fluoroalkyl group; a substituted or unsubstituted aryl group; or a curable group; R224 is a substituted or unsubstituted alkyl group.

[0128] According to one embodiment of the present invention, the cationic group is represented by any one selected from the following structural formulas: [ka] [ka] [ka]

[0129] According to one embodiment of the present invention, the ionic compound is any one selected from the group consisting of the following chemical formulas: [ka] [ka] [ka] [ka] [ka] [ka]

[0130] The ink composition will be specifically described below.

[0131] One embodiment of the present invention provides an ink composition comprising a compound represented by the above-mentioned Chemical Formula 1 and a solvent represented by the above-mentioned Chemical Formula A.

[0132] According to one embodiment of the present invention, the ink composition further comprises an ionic compound having an anionic group represented by Chemical Formula 2 above.

[0133] According to one embodiment of the present invention, the ionic compound further comprises the cationic group compound described above, i.e., the ink composition further comprises an ionic compound having an anionic group represented by Chemical Formula 2 described above and the cationic group described above.

[0134] According to a preferred embodiment of the present invention, the ink composition further contains at least one additional solvent selected from the group consisting of tetralin, 4-methoxytoluene, tetrahydrofuran, dioxane, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, a solvent represented by the following chemical formula C-1, and a solvent represented by the following chemical formula C-2: [ka]

[0135] In the chemical formulas C-1 and C-2, L100 and L101 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted alkylene group; G1 and G3 are the same or different and each independently represent hydrogen; deuterium; 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; G2 is a straight-chain alkyl group, G4 is a substituted or unsubstituted alkyl group; g1 and g3 each represent an integer of 1 to 5, and when g1 and g3 each represent 2 or more, the two or more substituents in parentheses are the same or different.

[0136] According to one embodiment of the present specification, the additional solvent is one or more selected from the group consisting of tetralin, 4-methoxytoluene, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, the solvent represented by the chemical formula C-1, and the solvent represented by the chemical formula C-2.

[0137] According to one embodiment of the present invention, the viscosity of the additional solvent is 1 cP to 15 cP.

[0138] By including an additional solvent having a viscosity within the above range, it is possible to advantageously prepare an ink composition having a viscosity suitable for the inkjet printing process.

[0139] According to one embodiment of the present invention, the additional solvent has a boiling point lower than that of the solvent represented by formula A.

[0140] According to one embodiment of the present invention, the boiling point of the additional solvent is 70°C to 280°C; 100°C to 280°C; 180°C to 280°C; 180°C to 265°C; or 190°C to 250°C.

[0141] By including the additional solvent having a boiling point within the above range, it is possible to advantageously prepare an ink composition having a drying speed suitable for the inkjet printing process.

[0142] According to one embodiment of the present invention, the solvent represented by the chemical formula C-1 is any one selected from the group consisting of the following structures: [ka]

[0143] According to one embodiment of the present invention, the solvent represented by the formula C-2 is benzyl butyrate.

[0144] According to one embodiment of the present invention, one or two of the above-mentioned exemplary solvents are used as the additional solvent.

[0145] According to one embodiment of the present invention, the ink composition includes a first additional solvent selected from the group consisting of tetralin, 4-methoxytoluene, tetrahydrofuran, dioxane, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, the solvent represented by the chemical formula C-1, and the solvent represented by the chemical formula C-2.

[0146] According to one embodiment of the present invention, the ink composition comprises a first additional solvent and a second additional solvent selected from the group consisting of tetralin, 4-methoxytoluene, tetrahydrofuran, dioxane, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, the solvent represented by the chemical formula C-1, and the solvent represented by the chemical formula C-2, wherein the first additional solvent and the second additional solvent are different from each other.

[0147] According to one embodiment of the present invention, the ink composition includes a first additional solvent selected from the group consisting of the solvent represented by the chemical formula C-1 and the solvent represented by the chemical formula C-2.

[0148] According to one embodiment of the present invention, the ink composition comprises a second additional solvent selected from the group consisting of tetralin, 4-methoxytoluene, tetrahydrofuran, dioxane, dipropylene glycol monomethyl ether, and tripropylene glycol monomethyl ether.

[0149] One embodiment of the present invention provides an ink composition comprising a compound represented by the aforementioned Chemical Formula 1; a solvent represented by the aforementioned Chemical Formula A; an ionic compound containing an anionic group represented by the aforementioned Chemical Formula 2; and an additional solvent.

[0150] One embodiment of the present invention provides an ink composition comprising a compound represented by the aforementioned chemical formula 1; a solvent represented by the aforementioned chemical formula A; an ionic compound; and an additional solvent, wherein the ionic compound comprises an anionic group represented by the aforementioned chemical formula 2 and the aforementioned cationic group.

[0151] According to one embodiment of the present invention, the compound represented by Chemical Formula 1 is contained in an amount of 0.1 wt% to 15 wt%, 0.1 wt% to 10 wt%, or 0.1 wt% to 5 wt%, relative to 100 wt% of the ink composition.

[0152] According to one embodiment of the present invention, the solvent represented by chemical formula A is contained in an amount of 1 wt% to 70 wt%, 1 wt% to 50 wt%, or 1 wt% to 30 wt%, relative to 100 wt% of the ink composition.

[0153] According to one embodiment of the present invention, the ionic compound containing the anionic group represented by Chemical Formula 2 is contained in an amount of 0.1 wt% to 15 wt%, 0.1 wt% to 10 wt%, or 0.1 wt% to 5 wt%, relative to 100 wt% of the ink composition.

[0154] According to one embodiment of the present invention, the additional solvent is contained in an amount of 10 wt% to 90 wt%, 10 wt% to 85 wt%, 10 wt% to 80 wt%, or 10 wt% to 70 wt%, relative to 100 wt% of the ink composition. However, the present invention is not limited to these examples, and the content of the additional solvent may be any amount commonly used by those skilled in the art to which the present invention pertains.

[0155] According to one embodiment of the present invention, the ink composition contains, relative to 100 wt%, the compound represented by Chemical Formula 1 at 0.1 wt% to 15 wt%; the solvent represented by Chemical Formula A at 1 wt% to 70 wt%; the ionic compound containing an anionic group represented by Chemical Formula 2 at 0.1 wt% to 15 wt%; and the additional solvent at 10 wt% to 85 wt%.

[0156] According to one embodiment of the present invention, the viscosity of the ink composition is 2 cP to 15 cP at room temperature. When the viscosity satisfies the above range, the device can be easily manufactured. Specifically, a uniform film can be formed when forming an organic layer in an organic light-emitting device.

[0157] The viscosity is measured at room temperature using a Brookfield viscometer after dissolving the target substance in a solvent at a concentration of 1 wt% to 3 wt%. The target substance is a compound represented by Chemical Formula 1, or a mixture of the compound represented by Chemical Formula 1 and the ionic compound. The solvent is a solvent represented by Chemical Formula A, or a mixed solvent of the solvent represented by Chemical Formula A and an additional solvent.

[0158] According to one embodiment of the present invention, the ink composition is in a liquid phase. The term "liquid phase" means that the ink composition is in a liquid state at room temperature and normal pressure.

[0159] In one embodiment of the present specification, the ink composition can be cured by a heat treatment or a light treatment. When the ink composition is cured, it can be expressed as a cured product of the ink composition.

[0160] According to one embodiment of the present invention, the ink composition further comprises a monomer containing a photocurable group and / or a thermosetting group, or a monomer containing a terminal group capable of forming a polymer by heat. The molecular weight of the monomer containing a photocurable group and / or a thermosetting group, or the monomer containing a terminal group capable of forming a polymer by heat, may be 3,000 g / mol or less, but is not limited to the molecular weights exemplified above.

[0161] The monomer containing a photocurable group and / or a thermosetting group, or a monomer containing an end group capable of forming a polymer by heat, may refer to an aryl such as phenyl, biphenyl, fluorene, or naphthalene; an arylamine; or a monomer in which a photocurable group and / or a thermosetting group or an end group capable of forming a polymer by heat is substituted on fluorene.

[0162] According to one embodiment of the present invention, the ink composition may further contain another additional solvent (hereinafter referred to as a third solvent) in addition to the aforementioned additional solvents. Examples of the third solvent include chlorine-based solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether-based solvents such as tetrahydrofuran, dioxane, and dipropylene glycol monomethyl ether; aromatic hydrocarbon-based solvents such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon-based solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; ketone-based solvents such as acetone, methyl ethyl ketone, cyclohexanone, isophorone, tetralone, decalone, and acetylacetone; and acetic acid esters. The solvent may be at least one selected from the group consisting of ester solvents such as butyl, butyl acetate, ethyl cellosolve acetate, and benzyl butyrate; polyhydric alcohols and derivatives thereof such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol; alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; and tetralin. However, the solvent is not limited to the above examples, and any solvent capable of dissolving or dispersing the compound represented by Chemical Formula 1 may be used.

[0163] According to one embodiment of the present invention, the ink composition is for forming at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer.

[0164] The pixel containing the ink composition or the cured product thereof will be specifically described below.

[0165] One embodiment of the present invention provides a pixel including an ink composition or a cured product thereof. The pixel may be included in an organic material layer, an organic light-emitting diode, or an organic light-emitting display device. Details regarding the organic material layer will be described later. Specifically, the organic light-emitting display device includes a plurality of pixels each consisting of red (R), green (G), and blue (B) subpixels, with an organic light-emitting diode (OLED) and a pixel circuit located in each subpixel. The organic light-emitting diode includes two electrodes (anode and cathode) and an organic light-emitting layer located therebetween, and the pixel circuit includes at least two thin film transistors and at least one capacitor. The organic material layer, organic light-emitting diode, or organic light-emitting display device may include a bank. Preferably, the organic material layer, organic light-emitting diode, or organic light-emitting display device may include a linear bank. The linear bank can define a linear pixel region and / or subpixel region. Typically, the light-emitting layer in the organic material layer includes a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer located in the red subpixel, the green subpixel, and the blue subpixel, respectively. In this case, the above-mentioned pixel may correspond to the pixel or subpixel. As a preferred example, the pixel corresponds to the sub-pixel.

[0166] According to one embodiment of the present invention, at least one of the pixels may be included in the organic layer, organic light emitting diode or organic light emitting display device described above.

[0167] According to one embodiment of the present invention, the thickness uniformity V of the one or more pixels is 0.4 or less, and the thickness uniformity V satisfies the following formula 1:

[0168] According to one embodiment of the present invention, the thickness uniformity V satisfies the following formula 1:

[0169]

number

[0170] In the present invention, the thickness uniformity V being 0.4 or less and satisfying the formula 1 means that the thickness uniformity V calculated through the formula 1 is 0.4 or less.

[0171] According to one embodiment of the present invention, the thickness uniformity is 0.01 to 0.4, or 0.02 to 0.4.

[0172] In the present invention, a low thickness uniformity value means that the thickness of the pixels is uniformly formed. That is, the lower the thickness uniformity value, the more uniformly formed the pixels are.

[0173] According to one embodiment of the present invention, the pixel thickness may refer to the thickness of the central portion of the pixel and may be measured by an optical thickness measuring device, such as, but not limited to, a Bruker Optical Profiler.

[0174] One embodiment of the present invention provides an organic layer comprising the above-described pixel, that is, one embodiment of the present invention provides an organic layer comprising the above-described ink composition or a cured product thereof.

[0175] The organic layer including the above-mentioned pixels will be specifically described below.

[0176] According to one embodiment of the present invention, the organic layer includes a plurality of the pixels. For example, the organic layer includes an x-axis on which na pixels are arranged, and a y-axis perpendicular to the x-axis on which nb pixels are arranged, and the na and nb are each 2 to 10. 4 is an integer.

[0177] According to one embodiment of the present invention, the na and nb are each 2 or more; 5 or more; 10 or more; 20 or more; or 40 or more, and 10 4 Below 10 3 or less; or 10 2 The following is the result.

[0178] According to one embodiment of the present invention, the organic layer includes 2 or more, 4 or more, 10 or more, 20 or more, 40 or more, 80 or more, or 100 or more of the pixels. 8 Less than or equal to 10 6 Less than or equal to 10 4 or 10 3 Includes less than 100 pieces.

[0179] According to one embodiment of the present invention, the pixels included in the organic layer are arranged in a line, for example, as shown in FIG.

[0180] According to one embodiment of the present invention, the organic layer includes a plurality of lines in which a plurality of the pixels are arranged in a row. For example, as shown in Figure 2, a plurality of lines may be formed at regular intervals. For example, the y-axis may be one line in which the above-mentioned nb pixels are arranged, and the x-axis may include as many lines as the number of pixels (na).

[0181] According to one embodiment of the present invention, the organic layer includes na×nb pixels.

[0182] According to one embodiment of the present invention, the plurality of pixels included in the organic layer have a uniform thickness.

[0183] According to one embodiment of the present invention, the organic layer includes n' pixels, and the thickness uniformity V of the n' pixels is 0.4 or less, and the thickness uniformity V satisfies the above-mentioned formula 1.

[0184] According to one embodiment of the present invention, n' is 2 to 10 4 is.

[0185] According to one embodiment of the present invention, the organic material layer is included in an organic light emitting device.

[0186] According to one embodiment of the present invention, the organic layer is formed by a solution process.

[0187] According to one embodiment of the present invention, the organic layer includes at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer.

[0188] According to one embodiment of the present invention, the organic layer is at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, and a light-emitting layer.

[0189] According to one embodiment of the present invention, the organic layer is at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer.

[0190] According to one embodiment of the present invention, the ink composition is for forming at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer.

[0191] According to a preferred embodiment of the present invention, the organic layer is a hole injection layer, a hole transport layer or an electron blocking layer.

[0192] The organic light-emitting element will be specifically described below.

[0193] One embodiment of the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the ink composition described above or a cured product thereof.

[0194] According to one embodiment of the present invention, the organic layer includes at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer, and the at least one layer selected from the group consisting of the hole injection layer, the hole transport layer, the hole injection and transport layer, the electron blocking layer, the emitting layer, the hole blocking layer, the electron injection layer, the electron transport layer, and the electron injection and transport layer comprises the ink composition or a cured product thereof.

[0195] According to one embodiment of the present invention, the organic layer includes at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer, and the at least one layer selected from the group consisting of the hole injection layer, the hole transport layer, the hole injection and transport layer, and the electron blocking layer includes the ink composition or a cured product thereof.

[0196] According to a preferred embodiment of the present invention, the organic layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer includes the ink composition or a cured product thereof.

[0197] According to one embodiment of the present invention, the organic material layer included in the organic light-emitting device includes n' pixels as described above, and the thickness uniformity V of the n' pixels is 0.4 or less, and the thickness uniformity V satisfies the above-mentioned formula 1.

[0198] A method for manufacturing an organic light-emitting element will be specifically described below.

[0199] One embodiment of the present invention includes the steps of providing a first electrode;

[0200] forming one or more organic layers on the first electrode; and

[0201] forming a second electrode on the one or more organic layers;

[0202] The forming of the organic material layer may include forming the organic material layer using the ink composition described above.

[0203] According to one embodiment of the present invention, the step of forming an organic layer using the ink composition may be a step of forming the organic layer on a substrate or an organic layer including line-shaped banks.

[0204] As an example, the above-described ink composition can be applied (Figure 3) to a substrate including linear banks (Figure 2), and then the ink composition can be dried and / or heat-treated to form a thin film (Figure 4).

[0205] According to another embodiment of the present invention, the step of forming the organic layer using the ink composition is performed using a spin coating method.

[0206] According to another embodiment of the present invention, the step of forming the organic layer using the ink composition is performed using a printing method.

[0207] According to one embodiment of the present invention, the printing method may be, for example, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing, but is not limited to the juxtaposed printing methods.

[0208] According to one embodiment of the present invention, the step of forming the organic layer using the ink composition is performed by an inkjet printing method.

[0209] The ink composition according to one embodiment of the present invention is suitable for solution processing due to the composition and structural properties of the substances contained therein, and can be formed by a printing method, which is economical in terms of time and cost when manufacturing elements.

[0210] According to one embodiment of the present invention, the step of forming the organic material layer on the first electrode may further include a drying step after one or more reduced pressure steps. For example, the step of forming the organic material layer on the first electrode may further include a drying step after two reduced pressure steps. In this case, the drying step after the first reduced pressure step may be performed at atmospheric pressure to 2×10 -2 Torr, and atmospheric pressure to 2×10 -2 The pressure reduction to torr can be performed over a period of 30 to 600 seconds. Furthermore, the drying stage after the second pressure reduction is 2×10 -2 ~2×10 -6 Torr, 2 x 10 -2 torr to 2×10 -6 The pressure can also be reduced to torr for 30 to 600 seconds.

[0211] According to one embodiment of the present invention, the step of forming an organic layer using the ink composition includes the steps of coating the ink composition; and subjecting the coated ink composition to a heat treatment or a light treatment.

[0212] According to one embodiment of the present invention, the step of forming an organic layer using the ink composition includes the steps of coating the ink composition on the first electrode or at least one organic layer; and subjecting the coated ink composition to a heat treatment or a light treatment.

[0213] According to one embodiment of the present invention, the heat treatment step can be carried out via heat treatment, and the heat treatment temperature in the heat treatment step may be 85°C to 250°C, 100°C to 250°C in one embodiment, and 150°C to 250°C in another embodiment.

[0214] According to one embodiment of the present invention, the heat treatment time in the heat treatment step is in the range of 10 minutes to 2 hours, and in another embodiment, it may be in the range of 10 minutes to 1 hour, and in another embodiment, it may be in the range of 20 minutes to 1 hour.

[0215] When the step of forming an organic material layer using the ink composition includes the heat treatment or light treatment, a plurality of compounds contained in the ink composition may be crosslinked to provide an organic material layer having a thin film structure, thereby preventing the organic material layer formed using the ink composition from being dissolved by a solvent or being morphologically affected or decomposed when another layer is laminated on the surface of the organic material layer.

[0216] Therefore, when an organic layer formed using the ink composition is formed by a heat treatment or light treatment step, the resistance to solvents is increased, and multiple layers can be formed by repeatedly performing solution coating and crosslinking methods, which increases stability and improves the lifespan of the device.

[0217] The types of organic layers included in the organic light-emitting device will be specifically described below.

[0218] According to one embodiment of the present invention, the organic light-emitting device includes one organic material layer, and the organic material layer includes the ink composition or a cured product thereof.

[0219] According to another embodiment of the present invention, the organic light-emitting device includes two or more organic material layers, and the two or more organic material layers include the ink composition or a cured product thereof. For example, any one of the two or more organic material layers includes the ink composition or a cured product thereof, and the organic light-emitting device further includes one or more remaining organic material layers. According to one embodiment, the remaining one or more organic material layers do not include the ink composition or a cured product thereof. According to another embodiment, the remaining one or more organic material layers further include the ink composition or a cured product thereof. However, the organic light-emitting device is not limited to the above examples.

[0220] The two or more organic material layers may include, for example, two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer. Here, the hole injection and transport layer refers to a layer that simultaneously injects holes and transports holes, and the electron injection and transport layer refers to a layer that simultaneously injects electrons and transports electrons. However, the organic material layers in the above group are merely examples and are not limited to these examples. Furthermore, the two or more organic material layers may include two or more layers that perform the same function, as necessary. An example organic light-emitting device includes a first hole injection layer and a second hole injection layer, but is not limited to these examples.

[0221] According to one embodiment of the present invention, the organic material layer includes an emitting layer. For example, the emitting layer includes the ink composition or a cured product thereof. For a specific example, the emitting layer includes the ink composition or a cured product thereof as an emitting layer host. For another specific example, the emitting layer includes the ink composition or a cured product thereof as an emitting layer dopant.

[0222] According to one embodiment of the present invention, the organic layer includes a hole injection and transport layer, a hole injection layer, a hole transport layer, and an electron blocking layer. For example, the hole injection and transport layer, the hole injection layer, the hole transport layer, or the electron blocking layer includes the ink composition or a cured product thereof.

[0223] According to a preferred embodiment of the present invention, the organic layer includes a hole transport layer or an electron blocking layer. For example, the hole transport layer or the electron blocking layer includes the ink composition or a cured product thereof.

[0224] According to a preferred embodiment of the present invention, the organic layer includes a hole injection layer and a hole transport layer.

[0225] According to one embodiment of the present invention, the organic layer further includes at least one layer selected from the group consisting of a hole-blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer. For example, at least one layer selected from the group consisting of the hole-blocking layer, the electron transport layer, the electron injection layer, and the electron injection and transport layer includes the ink composition or a cured product thereof. For another example, at least one layer selected from the group consisting of the hole-blocking layer, the electron transport layer, the electron injection layer, and the electron injection and transport layer does not include the ink composition or a cured product thereof.

[0226] One embodiment of the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, the organic material layers comprising an emitting layer and a hole injection layer, and the hole injection layer comprising the ink composition or a cured product thereof.

[0227] The organic material layers and the laminated structure of the organic light-emitting device including the organic material layers will be specifically described below.

[0228] According to one embodiment of the present invention, the organic material layer of the organic light-emitting device has a single layer structure. For example, the single layer organic material layer is provided between a first electrode and a second electrode of the organic light-emitting device and includes the ink composition or a cured product thereof. According to a specific embodiment, the single layer organic material layer is an emitting layer, and the emitting layer includes the ink composition or a cured product thereof.

[0229] According to another embodiment of the present invention, the organic material layer of the organic light-emitting device has a multilayer structure in which two or more organic material layers are stacked, for example, the multilayer structure organic material layer is provided between the first electrode and the second electrode of the organic light-emitting device.

[0230] According to one embodiment of the present invention, the organic layer of the multilayer structure includes an emitting layer and an organic layer other than the emitting layer. For example, the emitting layer is disposed between a first electrode and a second electrode, and the organic layer other than the emitting layer is disposed between the first electrode and the emitting layer. For another example, the emitting layer is disposed between the first electrode and the second electrode, and the organic layer other than the emitting layer is disposed between the emitting layer and the second electrode. For another example, the emitting layer is disposed between the first electrode and the second electrode, and any organic layer other than the emitting layer is disposed between the first electrode and the emitting layer, and another organic layer other than the emitting layer is disposed between the emitting layer and the second electrode. However, the above structure is merely illustrative and is not intended to be limiting. Furthermore, the organic layer other than the emitting layer may be, for example, one or more layers selected from the group consisting of a hole injection and transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, etc., but is not limited thereto.

[0231] In general, in an organic light emitting device, a hole injection layer, a hole transport layer, or an electron blocking layer is provided between an anode and an emitting layer. Specific examples include, but are not limited to, a hole injection layer provided on the anode, a hole transport layer provided on the hole injection layer, and an electron blocking layer provided on the hole injection layer.

[0232] In addition, in general, in an organic light-emitting device, an electron injection layer, an electron transport layer, or a hole blocking layer is provided between the cathode and the light-emitting layer. Specific examples include, but are not limited to, a hole blocking layer provided on the light-emitting layer, an electron transport layer provided on the hole blocking layer, and an electron injection layer provided on the electron transport layer.

[0233] The organic material layer of the multilayer structure included in the organic light-emitting device according to one embodiment of the present invention includes one or more layers selected from the group consisting of a hole injection and transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer; and an emitting layer, wherein the emitting layer is provided between a first electrode and a second electrode, and the one or more layers are provided between the first electrode and the emitting layer or between the second electrode and the emitting layer, and the one or more layers include an ink composition or a cured product thereof.

[0234] The structure of an organic light-emitting device according to one embodiment of the present invention is shown in FIG. 1. FIG. 1 illustrates an example of the structure of an organic light-emitting device in which a first electrode 201, a hole injection layer 301, a hole transport layer 401, an emitting layer 501, an electron injection and transport layer 601, and a second electrode 701 are sequentially stacked on a substrate 101. The hole injection layer 301 and / or the hole transport layer 401 in FIG. 1 may contain the ink composition or a cured product thereof, or may be formed using the ink composition. In this case, the specific organic layers that can form the hole injection layer 301 and / or the hole transport layer 401 in FIG. 1 using the ink composition, their materials, and manufacturing methods will be described later. Note that FIG. 1 illustrates an organic light-emitting device according to one embodiment of the present invention, but is not limited thereto.

[0235] As described above, the organic light emitting device having a single-layer or multi-layer organic material layer may have, for example, the following stacked structure, but is not limited thereto. (1) Anode / hole transport layer / light-emitting layer / cathode (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode (7) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode (10) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode (11) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode (14) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode (15) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode (17) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode (18) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capsule (19) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capsule

[0236] In the above structure, the "electron transport layer / electron injection layer" can be replaced with "electron injection and transport layer" or "layer that simultaneously performs electron injection and electron transport."

[0237] In the above structure, the "hole injection layer / hole transport layer" can be replaced with a "hole injection and transport layer" or a "layer that simultaneously performs hole injection and hole transport."

[0238] According to one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.

[0239] According to another embodiment of the present invention, the first electrode is a cathode and the second electrode is an anode.

[0240] According to one embodiment of the present invention, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

[0241] According to another embodiment of the present invention, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

[0242] The specific details of the organic layer, its materials, and manufacturing methods are described below. However, the organic light-emitting device of the present invention may be manufactured using materials and methods known in the art, except that the organic layer contains the above-mentioned compound.

[0243] In an organic light emitting device according to an embodiment of the present invention, at least one of the organic layers is formed using the ink composition or a cured product thereof, but other than this, the device may be manufactured using materials and methods known in the art.

[0244] For example, the organic light-emitting device of the present invention can be fabricated by sequentially stacking an anode, organic material layer, and cathode on a substrate. In this case, a metal, conductive metal oxide, or alloy thereof is deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form an anode. Organic material layers, including one or more of a hole injection layer, hole transport layer, light-emitting layer, electron injection layer, electron transport layer, hole transport and injection layer, and electron injection and transport layer, are then formed on the anode using a solution process, deposition process, or the like, and a material usable as a cathode is then deposited on the anode. In addition to this method, an organic light-emitting device can also be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0245] The anode material is preferably a material with a high work function to facilitate hole injection into the organic layer. Examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0246] The cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer, such as, but not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO / Al.

[0247] The light-emitting layer may include a host material and / or a dopant material.

[0248] The host material may be a fused aromatic ring derivative or a heterocyclic ring-containing compound, etc. Specifically, the fused aromatic ring derivative may be an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, etc., and the heterocyclic ring-containing compound may be a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, etc., but is not limited thereto.

[0249] Examples of the dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include fused aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and periflanthene. Styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and the substituted or unsubstituted group is one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamine groups. Specific examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. Metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0250] The hole injection layer is a layer that receives holes from the electrode. The hole injection material preferably has the ability to transport holes, accepts holes from the anode, and injects holes into the light-emitting layer or light-emitting material. Furthermore, a material that is excellent in preventing excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material is preferred. Furthermore, a material that is excellent in thin-film formation is preferred. The HOMO of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, and arylamine-based organic materials; hexanitrile hexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; and polythiophene-based conductive polymers such as anthraquinone and polyaniline.

[0251] The hole transport layer receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport layer may have a single layer structure or a multi-layer structure of two or more layers. The hole transport material is a material that can receive holes from the anode or hole injection layer and transport them to the light-emitting layer, and is preferably a material with high hole mobility. In the present invention, the hole transport material may include the compound represented by Chemical Formula 1. If necessary, other hole transport materials may be included in addition to the compound represented by Chemical Formula 1. Specific examples of such materials include, but are not limited to, arylamine-based organic compounds, carbazole-based compounds, conductive polymers, and block copolymers having both conjugated and non-conjugated portions. According to one embodiment of the present invention, the hole transport material is the ink composition or a cured product thereof.

[0252] The electron transport layer receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material that allows electrons to be efficiently injected from the cathode and transferred to the light-emitting layer, and is preferably a material with high electron mobility. Specific examples include, but are not limited to, 8-hydroxyquinoline aluminum complexes; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material, as used in the prior art. In particular, suitable cathode materials have a low work function and are typically followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0253] The electron injection layer is a layer that accepts electrons from the electrode. The electron injection material preferably has excellent electron transport ability, accepts electrons from the cathode, and injects electrons into the light-emitting layer or light-emitting material. Furthermore, a material that prevents excitons generated in the light-emitting layer from migrating to the hole injection layer and has excellent thin-film forming ability is preferred. Specific examples include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preolenylidenemethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives. Examples of the metal complex compounds include, but are not limited to, 8-hydroxyquinolinatolithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtholato)gallium.

[0254] The electron blocking layer is a layer that can prevent electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer, thereby improving the life and efficiency of the device. The electron blocking layer may be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and a layer that simultaneously performs hole injection and hole transport, using the compound of Chemical Formula 2.

[0255] The hole blocking layer is a layer that blocks holes from reaching the cathode and may be formed under the same conditions as the electron injection layer. Specific examples of materials for the hole blocking layer include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0256] The hole injection and transport layer may comprise the hole injection layer and hole transport layer materials described above.

[0257] The electron injection and transport layer may comprise the electron injection layer and electron transport layer materials described above.

[0258] When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0259] The organic light emitting device according to the present invention may be a top-emitting, a back-emitting or a double-sided emitting device depending on the materials used.

[0260] One embodiment of the present invention provides an electronic device including an organic light-emitting device comprising the ink composition described above or a cured product thereof, or comprising an organic material layer formed using the ink composition.

[0261] The electronic device may include, but is not limited to, an interlayer insulating film of a semiconductor element, a color filter, a black matrix, an overcoat, a column spacer, a passivation film, a buffer coating film, an insulating film for a multilayer printed circuit board, a cover coating of a flexible copper-clad plate, a buffer coating film, an insulating film solder resist film for a multilayer printed circuit board, an insulating film for an OLED, a protective film for a thin film transistor of a liquid crystal display element, an electrode protective film and a semiconductor protective film for an organic EL element, an OLED insulating film, an LCD insulating film, a semiconductor insulating film, a solar module, a touch panel, a display panel, and other display devices. [Example]

[0262] Hereinafter, the present invention will be described in detail with reference to examples. However, the examples of the present invention can be modified in various different forms, and the scope of the present invention should not be construed as being limited to the examples described below. The examples of the present invention are provided to more completely explain the present invention to those skilled in the art.

[0263] <Example of compound production> Synthesis Example A-1. Preparation of Compound 1

[0264] (1) Preparation of Intermediate 1-1 [ka] 1-Bromo-4-fluorobenzene (27.9 mL, 255 mmol) was added to tetrahydrofuran (THF) (500 mL). After purging with nitrogen, the mixture was cooled to -78 °C. n-BuLi (2.5 M Hex) (96 mL, 240 mmol) was added to a dropping funnel and slowly added to the reaction mixture. The mixture was stirred at -78 °C for 30 minutes. 2-Bromofluorenone (38.9 g, 150 mmol) was added. The mixture was slowly warmed to room temperature and stirred overnight. Distilled water was added to terminate the reaction, followed by extraction with ethyl acetate and water. The organic layer was collected, dried over MgSO4, and filtered. The filtrate was dried on a vacuum rotary evaporator to remove the organic solvent, obtaining intermediate 1-1, which was used in the next reaction.

[0265] (2) Preparation of Intermediate 1-2 [ka] Intermediate 1-1 (53 g, 150 mmol) and phenol (70.6 g, 750 mmol) were placed in a round-bottom flask (RBF). CH3SO3H (214 mL) was added and the mixture was stirred at 60 °C for 4 hours. After adding ice water, the mixture was extracted with ethyl acetate and water. The organic layer was collected, dried over MgSO4, and filtered. The filtrate was dried in a vacuum rotary evaporator to remove the organic solvent. After column purification, the mixture was crystallized in dichloromethane (DCM) / heptane to obtain 40.6 g of intermediate 1-2.

[0266] (3) Preparation of Intermediate 1-3 [ka] Intermediate 1-2 (45 g, 104 mmol), phenyltriflimide (PhNTf2) (81.8 g, 229 mmol), and 4-dimethylamylopyridine (DMAP) (2.54 g, 21 mmol) were placed in a round-bottom flask. Dichloromethane (416 mL) and triethylamine (TEA) (37.7 mL, 270 mmol) were added and stirred at room temperature (RT) for 1 h. The mixture was extracted with dichloromethane and 3% aqueous HCl. The organic layer was collected, dried over MgSO4, and filtered. The filtrate was dried on a vacuum rotary evaporator to remove the organic solvent. Intermediate 1-3 (52.5 g) was obtained by crystallization from dichloromethane / heptane.

[0267] (4) Preparation of Intermediate 1-4 [ka] Intermediate 1-3 (52.2 g, 92.7 mmol), potassium vinyltrifluoroborate (27.3 g, 204 mmol), Pd(dppf)Cl2 (3.4 g, 4.6 mmol), and K2CO3 (51.2 g, 971 mmol) were placed in a round-bottom flask. After purging with nitrogen, THF (371 mL) and HO (93 mL) were added and the mixture was stirred at 90 °C for 4 h. The mixture was extracted with ethyl acetate and water, and the organic layer was collected. The organic layer was dried over MgSO4 and filtered. The filtrate was dried on a vacuum rotary evaporator to remove the organic solvent. After column purification, the mixture was crystallized in DCM / EtOH to produce intermediate 1-4 (34 g).

[0268] (5) Preparation of Compound 1 [ka] 4-Aminodibenzofuran (513 mg, 2.8 mmol), intermediate 1-4 (2.53 g, 5.74 mmol), Pd(PtBu3)2 (72 mg, 0.14 mmol), and NaOtBu (1.08 g, 11.2 mmol) were placed in a RBF. After purging with nitrogen, toluene (14 mL) was added and the mixture was stirred at 90 °C for 1 h. The mixture was extracted with ethyl acetate and water, and the organic layer was collected. The organic layer was dried over MgSO4 and filtered. The filtrate was dried on a vacuum rotary evaporator to remove the organic solvent. After column purification, the mixture was crystallized in DCM / EtOH to obtain 2.0 g of compound 1. The synthesis of the compound was confirmed by LC-MS and NMR. MS: [M+H] + =904 NMR measurement of compound 1: 1 H NMR (500MHz, DMSO-d6) δ8.07(dd,1H), 7.92(d,1H), 7.63(dd,4H), 7.39-7.24(m,10H), 7.21(dd,1H), 7.10(m,2H), 6.97-6.83(m,18H), 6.72(dd,2H), 5.75(d,2H), 5.21(d,2H)

[0269] Synthesis Example A-2. Preparation of Compound 2

[0270] (1) Preparation of Intermediate 2-3 [ka] Intermediate 1-2 (40 g, 92.7 mmol), 4-nitrobenzaldehyde (21.2 g, 139 mmol), Cu(OAc) (842 mg, 4.64 mmol), and CsCO (45.3 g, 139 mmol) were placed in a RBF. DMF (310 mL) was added and the mixture was stirred at 100 °C for 4 h. The mixture was extracted with ethyl acetate and water, and the organic layer was collected. The organic layer was dried over MgSO and filtered. The filtrate was dried in a vacuum rotary evaporator to remove the organic solvent. After column purification, the mixture was crystallized in DCM / heptane to obtain 38.7 g of intermediate 2-3.

[0271] (2) Preparation of Intermediate 2-4 [ka] CH3PPh3Br (51.6 g, 144.6 mmol), KOtBu (16.2 g, 144.6 mmol), and THF (217 mL) were added to an RBF and cooled to 0 °C. A solution of intermediate 2-3 (38.7 g, 72.3 mmol) dissolved in THF (144 mL) was added to the reaction mixture. The temperature was raised to room temperature and stirred for 1 hour. Extraction was performed with ethyl acetate and water, and the organic layer was collected. After drying with MgSO4, the organic layer was filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, the mixture was crystallized using DCM / EtOH to obtain 33.7 g of intermediate 2-4.

[0272] (3) Preparation of Compound 2 [ka] 3-Aminodibenzofuran (513 mg, 2.8 mmol), intermediate 2-4 (3.1 g, 5.74 mmol), Pd(PtBu3)2 (72 mg, 0.14 mmol), and NaOtBu (1.08 g, 11.2 mmol) were placed in a RBF. After purging with nitrogen, toluene (14 mL) was added and the mixture was stirred at 90 °C for 1 h. The mixture was extracted with ethyl acetate and water, and the organic layer was collected. The organic layer was dried over MgSO4 and filtered. The filtrate was dried on a vacuum rotary evaporator to remove the organic solvent. After column purification, 2.9 g of compound 2 was obtained by crystallization in DCM / EtOH. The synthesis of the compound was confirmed by LC-MS and NMR. MS: [M+H] + =1088 NMR data of compound 2: 1 H NMR (500MHz, DMSO-d6) δ8.11(s,1H), 8.07(dd,1H), 7.85(d,1H), 7.82(dd,4H), 7.46(dd,4H), 7.39- 7.20(m,10H), 7.08(m,2H), 6.97-6.83(m,18H), 6.72(dd,2H), 6.65(d,4H), 5.75(d,2H), 5.21(d,2H)

[0273] Synthesis Example A-3. Preparation of Compound 3 [ka] Compound 3 was prepared in the same manner as in Synthesis Example A-1, except that 2-aminodibenzofuran was used instead of 4-aminodibenzofuran in (5) of Synthesis Example A-1. The synthesis of the compound was confirmed by LC-MS and NMR. MS: [M+H] + =904 NMR data of compound 3: 1 H NMR (500MHz, DMSO-d6) δ8.08(dd,1H), 7.92(d,1H), 7.63(dd,4H), 7.39-7.24(m,10H), 7.21(dd,1H), 7.10(m,2H), 6.97-6.83(m,18H), 6.72(dd,2H), 5.75(d,2H), 5.21(d,2H)

[0274] Synthesis Example A-4. Preparation of Compound 4 [ka] 2-amino-9,9-dimethylfluorene (586 mg, 2.8 mmol), intermediate 2-4 (3.1 g, 5.74 mmol), Pd(PtBu3)2 (72 mg, 0.14 mmol), and NaOtBu (1.08 g, 11.2 mmol) were placed in a RBF. After purging with nitrogen, toluene (14 mL) was added and the mixture was stirred at 90 °C for 1 h. The mixture was extracted with ethyl acetate and water, and the organic layer was collected. The organic layer was dried over MgSO4 and filtered. The filtrate was dried on a vacuum rotary evaporator to remove the organic solvent. After column purification, the mixture was crystallized in DCM / EtOH to obtain 2.6 g of compound 4. The synthesis of the compound was confirmed by LC-MS and NMR. MS: [M+H] + =1114 NMR data of compound 4: 1 H NMR (500MHz, DMSO-d6) δ7.95(dd,1H), 7.90(dd,1H), 7.84(dd,4H), 7.46(dd,4H), 7.39-7.20(m,11H) , 7.08(m,2H), 6.97-6.83(m,18H), 6.72(dd,2H), 6.65(d,4H), 5.75(d,2H), 5.21(d,2H), 1.68(s,6H)

[0275] Synthesis Example A-5. Preparation of Compound 5 [ka] Compound 5 was prepared in the same manner as in Synthesis Example A-2, except that 4-aminodibenzofuran was used instead of 3-aminodibenzofuran in (3) of Synthesis Example A-2. The synthesis of the compound was confirmed by LC-MS and NMR. MS: [M+H] + =1088 NMR data of compound 5: 1H NMR (500MHz, DMSO-d6) δ8.07(dd,1H), 7.92(d,1H), 7.82(dd,4H), 7.46(dd,4H), 7.39-7.24(m,10H), 7.21(dd,1H), 7.10(m,2H), 6.97-6.83(m,18H), 6.72(dd,2H), 6.65(d,4H), 5.75(d,2H), 5.21(d,2H)

[0276] <Example of ionic compound production> Production example of ionic compounds 1. Production example of compound D-1

[0277] (1) Preparation of Intermediate D-1-1 [ka] 1-Bromo-2,3,5,6-tetrafluoro-4-vinylbenzene (2 g, 7.84 mmol) was placed in THF (20 mL) in a 50 mL round-bottom flask and stirred at -78 °C for 30 minutes. n-BuLi in hexane (3.45 mL, 8.63 mmol, 2.5 M) was slowly added to the solution and stirred at -78 °C for 30 minutes. BCl3 (2.6 mL, 2.61 mmol, 1 M in heptane) was added to the reaction solution over 15 minutes at -78 °C. The temperature was slowly raised to room temperature, and the reaction solution was stirred for 1 day. Water (30 mL) was then added. The synthesized product was extracted with ethyl acetate (3 x 10 mL), and the solvent was then completely removed. The water was completely removed using a Dean-Stark column with benzene, and the solid was filtered to produce intermediate D-1-1 (800 mg, 43% yield).

[0278] (2) Preparation of Compound D-1 [ka] Intermediate D-1-1 (400 mg, 0.56 mmol), diphenyliodonium chloride (176 mg, 0.56 mmol), water (10 mL), and acetone (10 mL) were placed in a 25 mL round-bottom flask and stirred vigorously for 30 minutes. The mixture was extracted with dichloromethane (3 x 10 mL) to remove the solvent, and the mixture was dried to give compound D-1 (dopant 1) (552 mg, 100% yield). MS: [MH] - =711(negative mode) MS: [M+H] + =281(positive mode)

[0279] Ionic Compound Production Example 2. Production Example of Compound D-2

[0280] (1) Preparation of Intermediate D-2-1 [ka] A 100 mL round-bottom flask was charged with Mg (193 mg, 7.92 mmol), I2 (4 mg), and THF (10 mL) under a nitrogen atmosphere and stirred for 30 minutes. 4-Bromostyrene (1.04 mL, 7.92 mmol) was added, and a 30 °C water bath was placed under the round-bottom flask and stirred for 1 day. The reaction solution turned black, indicating that the Mg had dissolved. Ether (5 mL) was added to dilute the reaction solution. Tris(pentafluorophenyl)borane (1 g, 3.96 mmol) was dissolved in ether (5 mL) and slowly added to the reaction solution for 30 minutes. The solution was stirred for 1 day. Na2CO3 (0.1 M, 80 mL, 8.0 mmol) was slowly added to the reaction solution. The organic solvent was extracted with ethyl acetate (3 x 20 mL), and residual water was removed with MgSO4. To remove residual water and impurities, the mixture was distilled with benzene using a Dean-Stark column. When approximately 10 mL of solvent remained, the solution was cooled and filtered to produce intermediate D-2-1 (1.6 g, 64% yield).

[0281] (2) Preparation of Compound D-2 [ka] Intermediate D-2-1 (100 mg, 0.16 mmol), distilled water (10 mL), and PhICl (60 mg, 0.19 mmol) were added to a 25 mL round-bottom flask and stirred for 1 hour. Acetone (15 mL) was added to the reaction solution to form a precipitate, which was filtered and dried to produce compound D-2 (dopant 2) (140 mg, 100% yield). MS: [MH] - =615(negative mode) MS: [M+H] + =281(positive mode)

[0282] <Production example of ink composition>

[0283] Ink composition production example 1. HIL Host 1 and HIL Dopant 1 were mixed at a weight ratio of 8:2. Then, the mixture of HIL Host 1 and HIL Dopant 1 was added at a concentration of 2.0 wt% to a mixture of 10 wt%, 15 wt%, and 75 wt% of 3-isopropylbiphenyl (a solvent represented by Chemical Formula A), benzyl butyrate (a first additional solvent), and dipropylene glycol monomethyl ether (a second additional solvent). The mixed solution was stirred for 24 hours to completely dissolve the solution, thereby preparing Ink Composition 1.

[0284] Ink Composition Preparation Examples 2 to 63 Ink compositions 2 to 63 were prepared in the same manner as in Ink composition preparation example 1, except that the hole injection layer host 1, the hole injection layer dopant 1, the solvent represented by chemical formula A, the first additional solvent, and the second additional solvent were used as the substances shown in Table 1 below.

[0285] Ink composition preparation example 64. HIL Host 1 and HIL Dopant 1 were mixed at a weight ratio of 8:2. Then, the mixture of HIL Host 1 and HIL Dopant 1 was added at a concentration of 2.0 wt% to a mixture of 20 wt% and 80 wt% of 3-isopropylbiphenyl (a solvent represented by Chemical Formula A) and a first additional solvent, benzyl butyrate. The mixed solution was stirred for 24 hours to completely dissolve the solution, thereby preparing ink composition 64.

[0286] Ink composition preparation examples 65 to 75. Ink compositions 65 to 75 were prepared in the same manner as in Ink composition preparation example 64, except that the substances shown in Table 1 below were used as hole injection layer host 1, hole injection layer dopant 1, solvent, and first additional solvent.

[0287] [ka] [ka] [ka]

[0288] [Table 1A]

[0289] [Table 1B]

[0290] [Table 1C]

[0291] [Table 1D]

[0292] The solvents used in ink compositions 29 to 56 were tastromine (CAS#91-46-3), delta-tridecanolactone (CAS#7370-92-5), 1-nonylimidazole (CAS#53657-08-2), and N-isopentyl-N-phenylpropionamide (CAS#63916-02-9), respectively.

[0293] <Experimental Example A>

[0294] Example 1 The ink composition 1 was printed on the ITO substrate on which the bank was formed by an inkjet method, and then the printed substrate was placed in a vacuum chamber and the pressure was increased from normal pressure to 2×10 -2 The decompression time to torr was 60 seconds, 2 × 10 -2 torr to 2×10 -6 The pressure was reduced to 1000 torr for 180 seconds, and the thin film was dried at room temperature. After drying, the thin film was cured by heat treatment in a N2 atmosphere at 230°C on a hot plate for 1 hour. The thickness of each pixel in the cured thin film was measured using a Bruker Optical Profiler (Model: ContourGT-I), an optical thickness measurement device, and the inter-pixel thickness uniformity V was calculated based on the measured pixel thickness using Equation 1' below. The calculated values ​​are shown in Table 2 below.

[0295]

number

[0296] In Example 1, the ITO substrate with the banks formed thereon corresponds to FIG. 2, the printing on the ITO substrate with the banks formed thereon corresponds to FIG. 3, and the cured thin film corresponds to FIG. 4.

[0297] Examples 2 to 43 and Comparative Examples 1 to 32. The ink composition was produced in the same manner as in Example 1, except that the ink composition shown in Table 2 below was used instead of ink composition 1, and the thickness uniformity V was calculated and shown in Table 2 below.

[0298] [Table 2A]

[0299] [Table 2B]

[0300] As is clear from Table 2, the examples using an ink composition according to one embodiment of the present invention have a small thickness uniformity V of 0.4 or less. In particular, the examples using two additional solvents and using the solvent of formula C-1 (specifically, butyl benzoate) as the first additional solvent have a very small thickness uniformity V of 0.2 or less. On the other hand, the comparative examples using ink compositions not corresponding to the present invention have a large thickness uniformity V of more than 0.4.

[0301] In this regard, Figures 5 to 16 show pixel thickness uniformity characteristics according to experimental examples of the present invention. Specifically, Figures 5, 6, 11, and 12 show pixel thickness uniformity according to Examples 6, 16, 36, and 40, respectively. Figures 7 to 10 and 13 to 16 show pixel thickness uniformity according to Comparative Examples 5, 10, 15, 27, and 29 to 32, respectively. The horizontal axis represents pixel spacing (μm) and the vertical axis represents pixel thickness (nm). As is clear from Figures 5, 6, 11, and 12, Examples 6, 16, 36, and 40, which used ink compositions according to an embodiment of the present invention, had pixel thickness uniformity V of 0.13, 0.21, 0.26, and 0.07, respectively, which was small and less than 0.4, demonstrating a high degree of uniformity. As a result, when used in an organic layer in an organic light-emitting element, factors that affect the interference conditions of emitted light depending on the thickness are reduced, and excellent light emission and / or color development effects are expected.On the other hand, in Comparative Examples 5, 10, 15, 27, and 29 to 32, which used ink compositions that do not correspond to the present invention, the pixel thickness uniformity V was 0.84, 0.67, 0.70, 0.62, 0.57, 0.71, 0.89, and 0.48, respectively, all of which were values ​​greater than 0.4, confirming that the thickness difference between pixels was large and the thickness uniformity was uneven.

[0302] <Experimental Example B>

[0303] Example B-1. A glass substrate with a 700 Å thick indium tin oxide (ITO) thin film coating and a hydrophobic bank pattern on top was washed with distilled water for 30 minutes and then dried on a hot plate at 230°C for 10 minutes. Ink Composition 1 (Table 1) was inkjet-printed onto the cleaned substrate with the bank pattern and then heat-treated at 230°C for 30 minutes to form a 30 nm thick hole injection layer. A 40 nm thick hole transport layer was formed on the hole injection layer by inkjet-printing an ink prepared by dissolving the α-NPD compound (shown below) in cyclohexylbenzene at a concentration of 2 wt%. The substrate was then transferred to a vacuum evaporator and vacuum-deposited the following ADN compound and the following DPAVBi compound (shown below) at a weight ratio of 20:1 (ADN:DPAVBi) onto the hole transport layer to a thickness of 20 nm to form an emissive layer. The following BCP compound (shown below) was vacuum-deposited onto the emissive layer to a thickness of 35 nm to form an electron injection and transport layer. LiF was deposited to a thickness of 1 nm and aluminum to a thickness of 100 nm on the electron injection and transport layer to form a cathode, thereby completing an organic light emitting device.

[0304] [ka]

[0305] Examples B-2 to B-43. In Example B-1, the ink compositions shown in Table 3 below were used instead of the ink composition 1 to manufacture an organic light emitting device.

[0306] [Table 3A]

[0307] [Table 3B]

[0308] It was confirmed that the organic light emitting devices manufactured in Examples B-1 to B-43 were operable, and therefore it was confirmed that the ink composition according to the embodiment of the present invention can be applied to organic light emitting devices. [Explanation of symbols]

[0309] 101 Circuit board 201...1st electrode 301: Hole injection layer 401 Hole transport layer 501 Light-emitting layer 601 Electron injection and transport layer 701...Second electrode

Claims

1. An ink composition comprising a compound represented by the following chemical formula 1 and a solvent represented by the following chemical formula A: 【Chemistry 1】 In the above Chemical Formula 1 and A, Y is O, S, CRaRb or SiRcRd; Cy1 and Cy2 are the same or different and each independently represent a benzene ring or a naphthalene ring; Ra, Rb, Rc and Rd are the same or different and each independently represent an alkyl group or an aryl group, or are bonded to adjacent groups to form a ring; L1 and L2 are direct bonds; L3 is a direct bond; a phenylene group; or a naphthalene group; L11 and L12 are the same or different and each independently represent a direct bond; an alkylene group; or a phenylene group; X1 and X2 are the same or different and each independently represents a curable group; R1 and R2 are hydrogen; R3 and R4 are the same or different and each independently represent a hydrogen atom, an alkyl group, or an aryl group; a, b, and c are each 0 or 1; n1 and n2 each represent an integer of 0 to 7, and when n1 and n2 each represent 2 or more, the two or more substituents in parentheses are the same or different. m1 and m2 are each an integer of 1 to 5, n3 and n4 are each an integer of 0 to 4, m1+n3 is 5 or less, and m2+n4 is 5 or less; Y1 to Y10 are the same or different and each independently represent hydrogen; deuterium; an alkyl group; or an alkoxy group; The curable group is any one selected from the group consisting of the following structures: 【Chemistry 2】 In the above structure: Lc1 is a direct bond; —O—; —S—; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; lc is 1 or 2, When the lc is 2, the Lc1 are the same or different; When Lc1 is —O— or —S—, then lc is 1; Rc1 is a substituted or unsubstituted alkyl group; 【Transformation 3】 is the site that binds to Formula 1.

2. 2. The ink composition according to claim 1, wherein Y1 to Y10 are the same or different and each independently represents hydrogen; deuterium; an alkyl group having 1 to 8 carbon atoms; or an alkoxy group having 1 to 8 carbon atoms.

3. 2. The ink composition according to claim 1, wherein the solvent represented by chemical formula A is any one selected from the group consisting of the following compounds: 【Chemistry 4】 。

4. 2. The ink composition according to claim 1, wherein the solvent represented by chemical formula A has a surface tension of 33 mN / m to 37 mN / m.

5. 2. The ink composition according to claim 1, wherein the boiling point of the solvent represented by chemical formula A is 220°C to 350°C.

6. The ink composition according to claim 1 , wherein the chemical formula 1 is represented by the following chemical formula 11: 【Transformation 5】 In the above Chemical Formula 11, The definitions of L1 to L3, L11, L12, X1, X2, R1 to R4, Y, Cy1, Cy2, a, b, c, n1 to n4, m1 and m2 are the same as those in Chemical Formula 1.

7. An ink composition comprising any compound selected from the group consisting of the following compounds (excluding the compound represented by the following chemical formula A), and a solvent represented by the following chemical formula A: 【Chemical Engineering 6A】 【Chemistry 6B】 【Chemical 6C】 【6D Transformation】 [Transformation 6E] 【Chemical 6F】 [6G] 【Chemical Formula 6H】 【Chemical 6I】 【Chemical Formula 6J】 [Chemical formula 6K] [6L] 【6M】 【Chemical 6N】 [Chemical Formula 6O] [6P] 【Chemical Formula 6Q】 【Chemical Formula 6R】 【Transformation 7】 In the above chemical formula A, Y1 to Y10 are the same or different and each independently represents hydrogen, deuterium, an alkyl group, or an alkoxy group.

8. The ink composition according to claim 1, further comprising an ionic compound having an anionic group represented by the following chemical formula 2: 【Transformation 8】 In the above Chemical Formula 2, At least one of R201 to R220 is F; a cyano group; or a substituted or unsubstituted fluoroalkyl group; At least one of the remaining R201 to R220 is a curable group, and the curable group is as defined in claim 1; The remaining R201 to R220 are the same or different and each independently represent hydrogen; deuterium; a nitro group; —C(O)R220′; —OR221; —SR222; or —SO ３ R223; -COOR224; -OC(O)R225; -C(O)NR226R227; a substituted or unsubstituted alkyl group; a substituted or unsubstituted fluoroalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, R220' and R221 to R227 are the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

9. 9. The ink composition according to claim 8, wherein the anionic group represented by Chemical Formula 2 is represented by any one selected from the group consisting of the following chemical formulas: 【Chemical Engineering 9A】 【Chemical 9B】 【Chemical 9C】 In the above chemical formula: n is an integer from 1 to 3, m is an integer from 1 to 3, and m+n=4; q is an integer from 0 to 3, r is an integer from 1 to 4, and q+r=4; Z is deuterium; a halogen group; a nitro group; a cyano group; an amino group; —C(O)R220′; —OR221; —SR222; or —SO ３ R223; -COOR224; -OC(O)R225; -C(O)NR226R227; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, l is an integer of 1 to 4, and when l is 2 or more, Zs are the same or different; R220' and R221 to R227 are the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

10. the ionic compound further comprises a cationic group; 9. The ink composition according to claim 8, wherein the cationic group is a monovalent cationic group; a group consisting of an onium compound; or any cationic group selected from the group consisting of the following structural formulas: 【Chemistry 10】 In the structural formula: X １ ~X ７６ are the same or different and each independently represent hydrogen; deuterium; a cyano group; a nitro group; a halogen group; -COOR; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted fluoroalkyl group; a substituted or unsubstituted aryl group; or a curable group, wherein the curable group is as defined in claim 1; R224 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group; p is an integer from 0 to 10; a1 is 1 or 2, b1 is 0 or 1, and a1+b1=2.

11. The ink composition according to claim 10, further comprising at least one additional solvent selected from the group consisting of tetralin, 4-methoxytoluene, tetrahydrofuran, dioxane, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, a solvent represented by the following chemical formula C-1, and a solvent represented by the following chemical formula C-2: 【Chemistry 11】 In the chemical formulas C-1 and C-2, L100 and L101 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted alkylene group; G1 and G3 are the same or different and each independently represent hydrogen; deuterium; 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; G2 is a straight-chain alkyl group, G4 is a substituted or unsubstituted alkyl group; g1 and g3 each represent an integer of 1 to 5, and when g1 and g3 each represent 2 or more, the two or more parenthesized substituents may be the same or different.

12. With respect to 100 wt % of the ink composition, the compound represented by Chemical Formula 1 is present in an amount of 0.1 wt % to 15 wt %; the solvent represented by the chemical formula A is 1 wt % to 70 wt %; 0.1 wt % to 15 wt % of the ionic compound containing the anion group represented by Chemical Formula 2; and The ink composition according to claim 11, wherein the additional solvent is present in an amount of 10 wt % to 85 wt %.

13. 2. The ink composition according to claim 1, wherein the ink composition is for forming at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer.

14. A pixel comprising the ink composition according to any one of claims 1 to 13 or a cured product thereof.

15. An organic layer comprising the pixel of claim 14 .

16. n' of said pixels, The thickness uniformity V of the n' pixels is 0.4 or less, The organic layer according to claim 15, wherein the thickness uniformity V satisfies the following formula 1: [Equation 1] In the formula 1, X(i) is the thickness of the i-th pixel, Xm' is the average value of X(i) for i from 2 to n', n' is 2 to 10 ４ is an integer.

17. first electrode; a second electrode; and At least one organic layer provided between the first electrode and the second electrode An organic light-emitting device comprising: An organic light-emitting device, wherein at least one of the organic layers is the organic layer according to claim 15 .

18. the organic layer includes at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer; The organic light-emitting device according to claim 17 , wherein at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer comprises the ink composition or a cured product thereof.

Images