Ink composition, organic layer containing same, and organic light-emitting device containing 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. 10-2022-0120827, filed with the Korean Intellectual Property Office on September 23, 2022, the entire contents of which are incorporated herein by reference.

[0002] 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]

[0003] The organic light-emitting phenomenon is an example where an electric current is converted into visible light by an internal process of a specific organic molecule. The principle of the organic light-emitting phenomenon is as follows. When an organic layer is 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 electrons and holes injected into the organic layer recombine to form excitons, which fall back to the bottom state and emit light. An organic light-emitting device using this principle can generally be composed of a cathode and an anode and organic layers positioned therebetween, such as an anode injection layer, a hole transport layer, an emission layer, an electron injection layer, an electron transport layer, an electron blocking layer, a hole blocking layer, etc.

[0004] Conventionally, a deposition process has been mainly used to manufacture organic light emitting devices. However, there are problems in that a large amount of material is lost during the deposition process and it is difficult to manufacture a large-area device. To solve these problems, devices using a solution process have been developed.

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

[0006] 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]

[0007] One embodiment of the present invention provides an ink composition comprising a compound represented by the following chemical formula 1, and a first solvent represented by the following chemical formula A:

[0008] [ka]

[0009] In the above Chemical Formula 1 and A, Y1 to Y10 are the same or different and each independently represents 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; Cy1 to Cy4 are the same or different and each independently represents a substituted or unsubstituted hydrocarbon ring group; Z1 and Z2 are the same or different and each independently represents O, S, Se, or NR; L is a substituted or unsubstituted divalent hydrocarbon ring group; or a substituted or unsubstituted divalent heterocyclic group; L1 to L4 are the same or different and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group; L10 and L11 are the same or different and each independently represents a direct bond; or a substituted or unsubstituted arylene group; X1 and X2 are the same or different and each independently represents a curable group; R and R1 to R4 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; r1 and r2 are each an integer of 0 to 4, and when r1 and r2 are each 2 or more, the two or more substituents in the brackets are the same or different from each other, f1 and f2 are each an integer of 1 to 5, r1+f1 is 5 or less, and r2+f2 is 5 or less; Each of r3 and r4 is an integer of 1 to 7, and when each of r3 and r4 is 2 or more, the substituents in the two or more brackets are the same or different.

[0010] Another embodiment of the present invention provides a pixel comprising the ink composition described above or a cured version thereof.

[0011] Another embodiment of the present invention provides an organic layer comprising the above-described pixels.

[0012] Another embodiment of the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode; and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers is an organic layer described above. Effect of the Invention

[0013] The ink composition according to one embodiment of the present invention has the effect of providing a uniform coating thickness between pixels when coated on a plurality of pixels.

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

[0015] In addition, the ink composition according to one embodiment of the present invention exhibits resistance to certain solvents after curing, allowing solution processing during device fabrication, thereby enabling devices with larger area.

[0016] In addition, 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 when applied to an organic light-emitting device, it may be possible to obtain an element having a low driving voltage, excellent efficiency characteristics, and / or excellent life characteristics. [Brief description of the drawings]

[0017] [Figure 1] 1 shows an organic light-emitting device according to one embodiment of the present invention. [Diagram 2] FIG. 1 shows the results of NMR measurement of compound DA. [Diagram 3] FIG. 1 shows the results of NMR measurement of a compound DB. [Figure 4] 1 shows a line bank inkjet substrate onto which the ink composition is applied. [Diagram 5] The ink composition is shown applied to a line bank inkjet substrate. [Figure 6] FIG. 2 shows the ink composition formed as a thin film on a line bank inkjet substrate. [Figure 7] FIG. 2 shows a plan view of an organic layer on which a line bank is formed. [Figure 8] FIG. 2 shows a plan view of an organic layer in which isolated banks are formed. [Figure 9] FIG. 13 is a diagram showing the thickness of a pixel according to Example 1-1. [Figure 10] FIG. 13 is a diagram showing the thickness of a pixel according to Comparative Example 1-1. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0018] The present invention will be described in detail below. One embodiment of the present invention provides an ink composition comprising a compound represented by the following chemical formula 1, and a first solvent represented by the following chemical formula A:

[0019] [ka]

[0020] In the above Chemical Formula 1 and A, Y1 to Y10 are the same or different and each independently represents 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; Cy1 to Cy4 are the same or different and each independently represents a substituted or unsubstituted hydrocarbon ring group; Z1 and Z2 are the same or different and each independently represents O, S, Se, or NR; L is a substituted or unsubstituted divalent hydrocarbon ring group; or a substituted or unsubstituted divalent heterocyclic group; L1 to L4 are the same or different and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group; L10 and L11 are the same or different and each independently represents a direct bond; or a substituted or unsubstituted arylene group; X1 and X2 are the same or different and each independently represents a curable group; R and R1 to R4 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; r1 and r2 are each an integer of 0 to 4, and when r1 and r2 are each 2 or more, the two or more substituents in the brackets are the same or different from each other, f1 and f2 are each an integer of 1 to 5, r1+f1 is 5 or less, and r2+f2 is 5 or less; Each of r3 and r4 is an integer of 1 to 7, and when each of r3 and r4 is 2 or more, the substituents in the two or more brackets are the same or different.

[0021] The compound of formula 1 according to an embodiment of the present invention has a high HOMO (highest occupied molecular orbital) energy level and excellent hole mobility by including both a heterocyclic group and two fluorene derivatives. Specifically, the fluorene derivative is substituted with at least one fluoro group (-F), so that the compound has high stability and a high HOMO energy level. Furthermore, the compound has a high HOMO energy level by introducing a heterocyclic group near N. In addition, the two fluorene derivatives are introduced with a curable group, so that the radical formation at the position is suppressed and the stability of the compound is increased. As a result, when the compound of formula 1 is applied to an organic layer in an organic light emitting device, the interface characteristics with the adjacent layer are improved and the hole movement is facilitated, and the performance of the organic light emitting device is improved. In particular, when the compound of formula 1 is included 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, providing an organic light emitting device having high luminous efficiency and long life.

[0022] The first solvent represented by Chemical Formula A according to an embodiment of the present invention has excellent solubility for the solute (compound represented by Chemical Formula 1) contained in the ink composition by including biphenyl as a mother structure. In addition, it has an advantage that it has a good leveling effect and can improve the uniformity of the organic layer by reducing the thickness deviation between pixels. Specifically, it can reduce the thickness deviation between pixels where the ink composition is applied and dried (or heat treated). As a result, it is possible to reduce factors that affect the interference condition of light emitted according to the thickness in a light emitting device, and to expect excellent light emission and / or color development effects.

[0023] 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 another member (layer) exists between both members (layers).

[0024] In the present invention, when a part is said to "comprise" a certain component, this does not mean that other components are excluded, but that other components may be further included, unless otherwise specified.

[0025] In the present invention, the term "layer" is interchangeable with the term "film" commonly used in the art, 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. In one embodiment, the size of the "layer" may be the same as the whole element, may correspond to the size of a specific functional area, or may be smaller by a single sub-pixel.

[0026] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.

[0027] Methods and materials similar or equivalent to those described in the present invention can be used in the practice or testing of the embodiments of the present invention, and suitable methods and materials are described below. All publications, patent applications, patents and other references mentioned in the present invention are incorporated by reference in their entirety, and in the event of a conflict, the present invention, including definitions, will prevail if no particular passage is mentioned. Furthermore, the materials, methods and embodiments are merely illustrative and are not intended to be limiting.

[0028] In the present invention, [ka] each represent a moiety that is linked to a different substituent or bond.

[0029] In the present invention, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0030] In the present invention, the term "substituted or unsubstituted" means that it 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 heterocyclic group, or that it is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or that it has no substituents.

[0031] In the present invention, the linkage of two or more substituents means that a hydrogen atom of any of the substituents is linked to another substituent. For example, an isopropyl group is linked to a phenyl group, [ka] may be a substituent of the formula:

[0032] In the present invention, there is no restriction on the bonding direction of -COO-. For example, the -COO- is [ka] means all of the above.

[0033] 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).

[0034] 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, and 5-methylhexyl.

[0035] In the present invention, the alkylene group refers to an alkyl group having two bonding positions, i.e., a divalent group. The above description of the alkyl group can be applied to these groups, except that they are both divalent groups.

[0036] In the present invention, the number of carbon atoms in the cycloalkyl group is not particularly limited, but is preferably 3 to 60. In one embodiment, the number of carbon atoms in the cycloalkyl group is 3 to 30. Specific examples of the cycloalkyl group include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0037] In the present invention, the aryl group means a monovalent group of a monovalent aromatic hydrocarbon or an aromatic hydrocarbon derivative. In the present invention, the aromatic hydrocarbon means a compound containing a ring in which π electrons are completely conjugated and planar, and the aromatic hydrocarbon derivative means a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed with an aromatic hydrocarbon. In the present invention, the aryl group includes 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.

[0038] 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.

[0039] 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; 6 to 18; 6 to 16; 6 to 15; 6 to 14; 6 to 13; 6 to 12; or 6 to 10 carbon atoms, and may be, but is not limited to, a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylenyl group, chrysenyl group, fluorenyl group, etc.

[0040] In the present invention, the arylene group refers to an aryl group having two bonding positions, i.e., a divalent group. The above description of the aryl group can be applied to these groups, except that they are both divalent groups.

[0041] In the present invention, the heterocyclic group is an aromatic, aliphatic, or aromatic-aliphatic fused ring group containing at least one heteroatom selected from the group consisting of N, O, P, S, Si, and Se. The number of carbon atoms in the heterocyclic group is not particularly limited, and may be 2 to 60.

[0042] In the present invention, the heteroaryl group means a monovalent aromatic heterocycle. Here, the aromatic heterocycle means a monovalent group of an aromatic ring or a derivative of an aromatic ring, and a group containing at least one heteroatom selected from the group consisting of N, O, P, S, Si and Se. The derivative of the aromatic ring includes all structures in which an aromatic ring or an aliphatic ring is condensed with an aromatic ring. In addition, in the present invention, the heteroaryl group includes 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 number of carbon atoms in the heteroaryl group is preferably 2 to 60; 2 to 50; 2 to 30; 2 to 20; 2 to 18; or 2 to 13. Examples of heteroaryl groups include, but are not limited to, thiophene, furanyl, pyrrole, imidazole, thiazole, oxazole, pyridine, pyrimidine, triazine, triazole, acridine, pyridazine, pyrazine, quinoline, quinazoline, quinoxaline, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuran, phenanthrolinyl, and dibenzofuran groups.

[0043] In the present invention, a divalent heterocyclic group refers to a heterocyclic group having two bonding positions, i.e., a divalent group. The above description of the heterocyclic group can be applied to these groups, except that they are divalent groups.

[0044] In this specification, the term "adjacent" groups may refer to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions on a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

[0045] As used herein, in a ring formed by adjacent groups bonding to each other, the term "ring" refers to a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0046] In the present specification, the hydrocarbon ring may be an aromatic ring, an aliphatic ring, or an aromatic and aliphatic fused ring. Examples of aromatic and aliphatic fused rings include, but are not limited to, 1,2,3,4-tetrahydronaphthalene group, 2,3-dihydro-1H-indene group, etc.

[0047] In the present invention, the aromatic ring can be the same as that described above with respect to the aryl group.

[0048] In the present invention, the aliphatic ring is a non-aromatic hydrocarbon ring, and examples thereof include the above-mentioned examples of the cycloalkyl group and an adamantyl group.

[0049] In the present invention, the curable group can undergo a polymerization or crosslinking reaction, thereby proceeding with a reaction to increase the molecular weight, and includes a thermosetting group that is cured by heat; or a photocurable group that is cured by light.

[0050] In one embodiment of the present invention, the curable group has any of the following structures:

[0051] [ka]

[0052] In the above structure, R102 and R104 are the same or different and each independently represents hydrogen; deuterium; or a substituted or unsubstituted alkyl group; L101 to L108 are the same or different and each independently represents a direct bond; -O-; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group; Each of l104 to l108 is an integer of 1 to 10, and when each of l104 to l108 is 2 or more, the two or more substituents in the parentheses are the same or different from each other, [ka] is the site that is bonded to Chemical Formula 1.

[0053] The compound represented by Chemical Formula 1 will be specifically described below.

[0054] The ink composition of the present invention contains a compound represented by Chemical Formula 1.

[0055] In one embodiment of the present invention, the above-mentioned Chemical Formula 1 is represented by the following Chemical Formula 1-1.

[0056] [ka]

[0057] In the above Chemical Formula 1-1, The definitions of Cy1 to Cy4, Z1, Z2, L, L1 to L4, L10, L11, X1, X2, R1 to R4, r1 to r4, f1 and f2 are the same as those in Chemical Formula 1.

[0058] In one embodiment of the present invention, L10 and L11 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.

[0059] In one embodiment of the present invention, L10 and L11 are the same or different and each independently represent a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group.

[0060] In one embodiment of the present invention, L10 and L11 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted phenylene group.

[0061] In one embodiment of the present invention, L10 and L11 are the same or different and each independently a substituted or unsubstituted phenylene group.

[0062] In one embodiment of the present invention, the above-mentioned Chemical Formula 1 is represented by the following Chemical Formula 1-2.

[0063] [ka]

[0064] In the above Chemical Formula 1-2, The definitions of Cy1 to Cy4, Z1, Z2, L, L1 to L4, X1, X2, R1 to R4, r1 to r4, f1 and f2 are the same as those in Chemical Formula 1. R5 and R6 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; Each of r5 and r6 is an integer of 0 to 4, and when each of r5 and r6 is 2 or more, the two or more substituents in the parentheses are the same or different.

[0065] In one embodiment of the present invention, R5 and R6 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted 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 heterocyclic group having 2 to 30 carbon atoms.

[0066] In one embodiment of the present invention, R5 and R6 are the same or different and each independently represent hydrogen; deuterium; a halogen group; an alkyl group having 1 to 20 carbon atoms; an alkoxy group having 1 to 20 carbon atoms; an aryl group having 6 to 30 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms.

[0067] In one embodiment of the present invention, R5 and R6 are each hydrogen or deuterium.

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

[0069] In one embodiment of the present invention, Cy1 to Cy4 are the same or different and each independently is an aromatic ring.

[0070] In one embodiment of the present invention, Cy1 to Cy4 are the same or different and each independently represent a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring.

[0071] In one embodiment of the present invention, each of Cy1 to Cy4 is a benzene ring.

[0072] In one embodiment of the present invention, the above-mentioned formula 1 is represented by the following formula 1-3.

[0073] [ka]

[0074] In the above Chemical Formula 1-3, The definitions of Z1, Z2, L, L1 to L4, L10, L11, X1, X2, R1 to R4, r1 to r4, f1 and f2 are the same as those in Chemical Formula 1. R60 and R61 are the same or different, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or is combined with an adjacent group to form a substituted or unsubstituted ring; Each of r60 and r61 is an integer of 1 to 7, and when each of r60 and r61 is 2 or more, the two or more substituents in the parentheses are the same or different.

[0075] In one embodiment of the present invention, the above-mentioned Chemical Formula 1 is represented by the following Chemical Formula 1-4 or 1-5.

[0076] [ka]

[0077] In the above Chemical Formulas 1-4 and 1-5, The definitions of Z1, Z2, L, L1 to L4, L10, L11, X1, X2, R1 to R4, r1 to r4, f1 and f2 are the same as those in Chemical Formula 1. R70 to R73 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; Each of r70 and r71 is an integer of 1 to 7, each of r72 and r73 is an integer of 1 to 9, and when each of r70 to r73 is 2 or more, the substituents in the two or more brackets are the same or different from each other.

[0078] In one embodiment of the present invention, R70 to R73 are each hydrogen or deuterium.

[0079] In one embodiment of the present invention, L is a substituted or unsubstituted divalent hydrocarbon ring group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

[0080] According to another embodiment, the L is a substituted or unsubstituted divalent hydrocarbon ring group having 6 to 30 carbon atoms.

[0081] In one embodiment of the present invention, L is a divalent hydrocarbon ring group which is unsubstituted or substituted with an alkyl group or an aryl group.

[0082] In one embodiment of the present invention, L is any of the following structures:

[0083] [ka]

[0084] In the above structure, R10 to R31 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; r10 to r21 each represents an integer of 1 to 4, r22, r23, r28, and r29 each represents an integer of 1 to 3, r24 and r25 each represents an integer of 1 to 7, r26 is an integer of 1 to 8, and r27 is an integer of 1 to 6; when r10 to r29 each represents 2 or more, the two or more substituents in parentheses are the same or different from each other; [ka] is the site of attachment to Chemical Formula 1.

[0085] In one embodiment of the present invention, R10 to R29 are the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0086] In one embodiment of the present invention, R10 to R29 are the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0087] In one embodiment of the present invention, R10 to R29 are the same or different and each independently represents hydrogen; deuterium; or an alkyl group having 1 to 20 carbon atoms.

[0088] In one embodiment of the present invention, L1 to L4 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

[0089] In one embodiment of the present invention, L1 to L4 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0090] In one embodiment of the present invention, L1 to L4 are the same or different and each independently represent a direct bond; a halogen group; or an arylene group having 6 to 30 carbon atoms which is unsubstituted or substituted with an alkyl group.

[0091] In one embodiment of the present invention, L1 to L4 are the same or different and each independently represent a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group.

[0092] In one embodiment of the present invention, L1 to L4 are the same or different and each independently represent a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0093] In one embodiment of the present invention, L1 to L4 are the same or different and each independently represent a direct bond; a phenylene group unsubstituted or substituted with deuterium, a halogen group, or an alkyl group; or a biphenylene group unsubstituted or substituted with deuterium, a halogen group, or an alkyl group.

[0094] In one embodiment of the present invention, L1 to L4 are the same or different and each independently represent a direct bond; a phenylene group unsubstituted or substituted with deuterium, F or an alkyl group having 1 to 30 carbon atoms; or a biphenylene group unsubstituted or substituted with deuterium, F or an alkyl group having 1 to 30 carbon atoms.

[0095] In one embodiment of the present invention, R1 to R4 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0096] In one embodiment of the present invention, R1 to R4 are the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0097] In one embodiment of the present invention, R1 to R4 are the same or different and each independently represents hydrogen; deuterium; or an alkyl group.

[0098] In one embodiment of the present invention, Z1 and Z2 are the same or different and each independently represents O or S.

[0099] In one embodiment of the present invention, f1 and f2 each represent an integer of 1 to 5.

[0100] In one embodiment of the present invention, f1 is 1. In one embodiment of the present invention, f1 is 2. In one embodiment of the present invention, f1 is 3. In one embodiment of the present invention, f1 is 4. In one embodiment of the present invention, f1 is 5.

[0101] In one embodiment of the present invention, f2 is 1. In one embodiment of the present invention, f2 is 2. In one embodiment of the present invention, f2 is 3. In one embodiment of the present invention, f2 is 4. In one embodiment of the present invention, f2 is 5.

[0102] In one embodiment of the present invention, X1 and X2 are the same or different and each independently selected from the aforementioned curable group structures.

[0103] In one embodiment of the present invention, X1 and X2 are the same or different and each independently represent any of the following structures:

[0104] [ka]

[0105] In the above structure, R102 and R104 are the same or different and each independently represents hydrogen; deuterium; or a substituted or unsubstituted alkyl group; L102, L104, L106 and L107 are the same or different and each independently represents a direct bond; -O-; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group; l104, l106 and l107 each represent an integer of 1 to 10, and when l104, l106 and l107 each represent 2 or more, the two or more substituents in parentheses are the same or different from each other, [ka] is the site that is bonded to Chemical Formula 1.

[0106] In one embodiment of the present invention, X1 and X2 are the same or different and each independently represent any of the following structures.

[0107] [ka]

[0108] In one embodiment of the present invention, the compound represented by Chemical Formula 1 has any one of the following structures:

[0109] [ka]

[0110] [ka]

[0111] [ka]

[0112] [ka]

[0113] [ka]

[0114] [ka]

[0115] The first solvent represented by chemical formula A will be specifically described below.

[0116] According to one embodiment of the present invention, Y1 to Y10 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a hydroxyl 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.

[0117] 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.

[0118] According to one embodiment of the present invention, Y1 to Y10 are the same or different and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

[0119] According to one embodiment of the present invention, the Y1 to Y10 are the same or different and each independently represents 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.

[0120] 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.

[0121] 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.

[0122] According to one embodiment of the present invention, Y1 to Y10 are the same or different and each independently represents hydrogen; deuterium; an alkyl group; or an alkoxy group.

[0123] 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.

[0124] 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. According to one embodiment of the present invention, Y1 to Y10 are the same or different and each independently represents hydrogen; deuterium; an ethyl group; a propyl group; a butyl group; a pentyl group; an isopropyl group; or a methoxy group.

[0125] In one embodiment of the present invention, the first solvent represented by the chemical formula A has any one of the following structures:

[0126] [ka]

[0127] In the above structure, Y1 to Y10 are the same or different and each independently represents a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

[0128] In one embodiment of the present invention, the first 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 structures:

[0129] [ka]

[0130] In one embodiment of the present invention, the first solvent represented by formula A has any of the above structures.

[0131] In one embodiment of the present invention, the surface tension of the first solvent represented by the chemical formula A is 32 mN / m to 38 mN / m, specifically, 33 mN / m to 37 mN / m; or 33.5 mN / m to 36.5 mN / m.

[0132] According to one embodiment of the present invention, the surface tension of the first solvent represented by the chemical formula A satisfies the above range, so that the range of surface tension between other substances other than the first solvent represented by the 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 the solution process should generally be composed of substances that allow the ink composition to have a surface tension in the range of 25 mN / m to 45 mN / m, and it is preferable that the difference in surface tension between the substances is small. The surface tension in the range of 32 mN / m to 38 mN / m is close to the intermediate value of the preferred surface tension range, so that when the first solvent represented by the chemical formula A has a surface tension in the range of 32 mN / m to 38 mN / m, the difference in surface tension between other substances other than the first solvent represented by the chemical formula A can be adjusted to be small. When the difference in surface tension between other substances other than the first solvent represented by the chemical formula A is small, there is an advantage that the flatness of the organic layer of the organic light-emitting device manufactured by the solution process and the thickness uniformity of the pixel are excellent.

[0133] In one embodiment of the present invention, the boiling point of the first solvent represented by the chemical formula A is 250°C to 350°C; 270°C to 350°C; or 280°C to 330°C.

[0134] By including the first solvent represented by the formula A having a boiling point in the above range, it is expected that the flatness of the organic layer and / or the thickness uniformity of the pixels will be excellent when manufacturing the organic layer of the organic light emitting device through solution processing. Specifically, the first solvent represented by the formula A has the lowest vapor pressure among the constituent solvents and is not removed in the initial drying step, so that it has the advantage of being able to adjust the difference in surface tension between materials remaining after the initial drying step. As a result, it has the advantage of being excellent in the flatness of the organic layer of the organic light emitting device and / or the thickness uniformity of the pixels.

[0135] In one embodiment of the present invention, the ink composition further contains a second solvent, and the second solvent contains at least one of a solvent represented by any one of the following chemical formulas B to D, methoxytoluene, and tetralin.

[0136] [ka]

[0137] In the above chemical formulas B to D, L50 is a direct bond; or an alkylene group; L51 and L53 to L55 are the same or different and each independently represents a direct bond; -O-; or a substituted or unsubstituted alkylene group; L52 is -COO-, R50, R51, and R54 to R56 are the same or different and each independently represents a substituted or unsubstituted alkyl group; R53 is hydrogen; deuterium; an alkoxy group; or a substituted or unsubstituted alkyl group; a1 is 0 or 1, r53 is an integer of 1 to 5, and when r53 is 2 or more, the two or more R53's are the same or different from each other, Each of l50, l51, and l53 to l55 is an integer of 1 to 10, and when each of l50, l51, and l53 to l55 is 2 or more, the structures in the two or more parentheses are the same or different from each other.

[0138] In one embodiment of the present invention, L50 is a direct bond; or an alkylene group having 1 to 10 carbon atoms. In one embodiment of the present invention, L50 is a direct bond; or an alkylene group having 1 to 6 carbon atoms. In one embodiment of the present invention, L50 is a direct bond; a methylene group; an ethylene group; a propylene group; or a butylene group.

[0139] In one embodiment of the present invention, the l50 is an integer of 1 to 5.

[0140] In one embodiment of the present invention, L51 and L53 to L55 are the same or different and each independently represent a direct bond; --O--; or an alkylene group having 1 to 10 carbon atoms.

[0141] In one embodiment of the present invention, L51 and L53 are the same or different and each independently represents a direct bond; --O--; or an alkylene group having 1 to 10 carbon atoms. In one embodiment of the present invention, L51 and L53 are the same or different and each independently represents a direct bond; --O--; or an alkylene group having 1 to 5 carbon atoms. In one embodiment of the present invention, L51 and L53 are the same or different and each independently represent a direct bond; --O--; a methylene group; an ethylene group; or a propylene group.

[0142] In one embodiment of the present invention, the l51 and l53 are integers of 1 to 5, respectively.

[0143] In one embodiment of the present invention, L54 and L55 are the same or different and each independently represents --O-- or an alkylene group. In one embodiment of the present invention, L54 and L55 are the same or different and each independently represents -O-; or a straight-chain or branched-chain alkylene group.

[0144] In one embodiment of the present invention, l54 and l55 each represent an integer of 1 to 10.

[0145] In one embodiment of the present invention, a1 is 0. In one embodiment of the present invention, a1 is 1.

[0146] In one embodiment of the present invention, R50, R51 and R54 to R56 are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. In one embodiment of the present invention, R50, R51 and R54 to R56 are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0147] In one embodiment of the present invention, R50 and R51 are the same or different and each independently represents an alkyl group having 1 to 10 carbon atoms. In one embodiment of the present invention, R50 and R51 are the same or different and each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms. In one embodiment of the present invention, R50 and R51 are the same or different and each independently represent a linear alkyl group having 1 to 10 carbon atoms; or a branched alkyl group having 3 to 10 carbon atoms.

[0148] In one embodiment of the present invention, R53 is hydrogen; or an alkoxy group. In one embodiment of the present invention, R53 is hydrogen or an alkoxy group having 1 to 10 carbon atoms.

[0149] In one embodiment of the present invention, R54 is an alkyl group having 1 to 30 carbon atoms. In one embodiment of the present invention, R54 is a linear or branched alkyl group having 1 to 30 carbon atoms. In one embodiment of the present invention, R54 is a linear alkyl group having 1 to 30 carbon atoms; or a branched alkyl group having 4 to 30 carbon atoms. In one embodiment of the present invention, R54 is a linear alkyl group having 1 to 10 carbon atoms; or a branched alkyl group having 4 to 10 carbon atoms.

[0150] In one embodiment of the present invention, R55 and R56 are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. In one embodiment of the present invention, R55 and R56 are the same or different and each independently represent a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms. In one embodiment of the present invention, R55 and R56 are the same or different and each independently represent an alkyl group unsubstituted or substituted with a hydroxy group. In one embodiment of the present invention, R55 and R56 are the same or different and each independently represents an alkyl group having 1 to 10 carbon atoms which is unsubstituted or substituted with a hydroxy group.

[0151] In one embodiment of the present invention, the second solvent contains one or two of the solvents represented by any one of the chemical formulae B to D, methoxytoluene, and tetralin.

[0152] In one embodiment of the present invention, the second solvent is at least one selected from the group consisting of dibutyl oxalate, ethyl benzoate, tripropylene glycol methyl ether, diethyl adipate, butyl carbitol acetate, benzyl butyrate, methyl methoxybenzoate, butyl benzoate, dibutyl succinate, isoamyl benzoate, 2-phenoxyethyl isobutyrate, diisopropyl malonate, tetralin, methoxytoluene, and dipropylene glycol monomethyl ether.

[0153] In one embodiment of the present invention, the ink composition contains a second solvent represented by any one of the chemical formulas B to D, and further contains a third solvent different from the first solvent and the second solvent.

[0154] In one embodiment of the present invention, the third solvent is any one of the solvents represented by any one of chemical formulas B to D, methoxytoluene, and tetralin, and is different from the second solvent.

[0155] In one embodiment of the present invention, the boiling point of the second solvent is 180°C to 280°C.

[0156] In one embodiment of the present invention, the boiling point of the first solvent is 250° C. to 350° C., and the boiling point of the second solvent is 180° C. to 280° C., and the boiling point of the first solvent is higher than that of the second solvent. In this way, since the boiling point of the second solvent is lower than that of the first solvent, the second solvent evaporates first when the ink composition is dried, and the proportion of the first solvent increases, so that the solvent drying speed and the evenness of the ink can be adjusted.

[0157] In one embodiment of the present invention, the first and second solvents are used simultaneously, which has the effect of shortening the drying time and improving the uniformity of the thin film.

[0158] In one embodiment of the present invention, the first solvent is contained in an amount of 4 wt% (mass%) to 60 wt% (mass%), and the second solvent is contained in an amount of 40 wt% to 96 wt% based on the total solvent. Specifically, the first solvent is contained in an amount of 5 wt% to 35 wt%, and the second solvent is contained in an amount of 65 wt% to 95 wt%. The ink composition must maintain a liquid state in the pixel after printing until entering the vacuum chamber. If the first solvent is contained in an amount of less than 4 wt%, there is a problem that a large amount or all of the ink composition dries out during the printing process of the ink composition. On the other hand, if the first solvent is contained in the ink composition in an amount of more than 60 wt%, the solvent may remain in the thin film.

[0159] In one embodiment of the invention, total solvent means the first solvent and the second solvent combined.

[0160] The ionic compound containing an anion group represented by Chemical Formula 2 will be specifically described below.

[0161] In one embodiment of the present invention, the ink composition further comprises an ionic compound having an anionic group represented by the following chemical formula 2.

[0162] [ka]

[0163] 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 halogen group; a nitro group; a cyano group; an amino group; -OR221; -SR222; or -SO 3 R223;-COOR224;-OC(O)R225;-C(O)NR226R227;-C(O)R228; 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, R221 to R228 are the same or different and each independently represents a hydrogen atom; a deuterium atom; or a substituted or unsubstituted alkyl group.

[0164] In one embodiment of the present invention, an ionic compound containing an anionic group represented by chemical formula 2 (hereinafter, an anionic group compound) has a curable group introduced therein. In contrast, if a curable group is not introduced, the ionic compound does not cure, and the ionic compound moves between electrodes or layers, resulting in a decrease in the characteristics of the device. On the other hand, as the number of curable groups increases, the curing rate of the ionic compound or a composition containing the same increases, and the film retention rate improves.

[0165] In one embodiment of the present invention, the number of the curable group in the anionic compound represented by Chemical Formula 2 is one. In one embodiment of the present invention, the number of curable groups in the anionic compound represented by Chemical Formula 2 is two. In one embodiment of the present invention, the anionic compound represented by Chemical Formula 2 has four curable groups.

[0166] In one embodiment of the present invention, the anion group compound represented by Chemical Formula 2 has 16 to 19 F, cyano groups, or substituted or unsubstituted fluoroalkyl groups.

[0167] In one embodiment of the present invention, the part by weight of F in the anionic group compound is 15 parts by weight to 50 parts by weight or less relative to 100 parts by weight of the anionic group compound. In one embodiment of the present invention, the part by weight 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.

[0168] In one embodiment of the present invention, the anionic group compound has 8 to 20 F per 100 parts by weight of the anionic group compound.

[0169] As described above, when the proportion of F, cyano groups, or fluoroalkyl groups in the molecule is high, the film retention rate during heat treatment is improved.

[0170] According to one embodiment of the present invention, the ionic compound may be used in a hole injection layer of an organic light emitting device, and when used in a hole injection layer, it may 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 the performance of the hole injection layer.

[0171] In 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 via 19F NMR, a method commonly used for F analysis.

[0172] In one embodiment of the present invention, at least one of the benzene rings containing R201 to R205, the benzene ring containing R206 to R210, the benzene ring containing R211 to R215, and the benzene ring containing R216 to R220 in Chemical Formula 2 is selected from those of the following structural formulas.

[0173] [ka]

[0174] In one embodiment of the present invention, the formula 2 has any one of the following structures:

[0175] [ka]

[0176] [ka]

[0177] In the above structure, n1 is an integer from 1 to 3, m1 is an integer from 1 to 3, and n1+m1=4; n2 is an integer from 0 to 3, m2 is an integer from 1 to 4, and n2+m2=4; M1 is deuterium; halogen group; nitro group; cyano group; amino group; -OR221; -SR222; -SO 3 R223;-COOR224;-OC(O)R225;-C(O)NR226R227;-C(O)R228; 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, R221 to R228 are the same or different and each independently represents a hydrogen atom; a deuterium atom; or a substituted or unsubstituted alkyl group. i is an integer of 1 to 4, and when i is 2 or more, two or more M1's are the same or different.

[0178] In one embodiment of the present invention, the ionic compound further comprises a cationic group. Specifically, the ink composition further comprises an ionic compound having an anionic group and a cationic group represented by the above-mentioned Chemical Formula 2.

[0179] In one embodiment of the present invention, the ionic compound further comprises a cationic group, and the cationic group is a monovalent cationic group, an onium compound, or any of the following structures:

[0180] [ka]

[0181] In the above structure, Q30 to Q105 are the same or different and each independently represents hydrogen; deuterium; a cyano group; a nitro group; a halogen group; a hydroxyl group; -COOR250; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a curable group; R250 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group; x is an integer from 0 to 10; p1 is 1 or 2, q1 is 0 or 1, and p1+q1=2.

[0182] In 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:

[0183] In one embodiment of the present invention, the cationic group is an onium compound; or any one selected from the above structural formulas.

[0184] In one embodiment of the invention, the cationic group has any of the following structures:

[0185] [ka]

[0186] In the above structure, Q30 to Q34, Q30' to Q34' and Q62 to Q95 are the same or different and each represents a hydrogen atom; a deuterium atom; a cyano group; a nitro group; a halogen group; a hydroxyl group; -COOR250; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a curable group; R250 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0187] In one embodiment of the invention, the cationic group has any of the following structures:

[0188] [ka]

[0189] In one embodiment of the present invention, the ionic compound is represented by any one of the following chemical formulas D-1 to D-37.

[0190] [ka]

[0191] [ka]

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] In one embodiment of the present invention, the anionic group represented by Chemical Formula 2 and the cationic group in the ionic compound are contained in an equivalent ratio of 1:5 to 5:1. Specifically, the anionic group represented by Chemical Formula 2 and the cationic group are contained in an equivalent ratio of 1:1.

[0196] The ink composition will be specifically described below.

[0197] One embodiment of the present invention provides an ink composition comprising a compound represented by the above-mentioned Chemical Formula 1 and a first solvent represented by the above-mentioned Chemical Formula A.

[0198] 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.

[0199] According to one embodiment of the present invention, the ionic compound further comprises the cationic group described above, i.e., the ink composition further comprises an ionic compound comprising the anionic group represented by the above Chemical Formula 2 and the above cationic group.

[0200] One embodiment of the present invention provides an ink composition comprising a compound represented by the above-mentioned chemical formula 1 and a first solvent represented by the above-mentioned chemical formula A, and further comprising one or more of the above-mentioned anionic group compound; the above-mentioned cationic group; and the above-mentioned second solvent.

[0201] One embodiment of the present invention provides an ink composition comprising a compound represented by the above-mentioned chemical formula 1; a first solvent represented by the above-mentioned chemical formula A; an ionic compound comprising the above-mentioned anionic group represented by the above-mentioned chemical formula 2 and the above-mentioned cationic group; and the above-mentioned second solvent.

[0202] 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.

[0203] According to one embodiment of the present invention, the first solvent represented by the chemical formula A is contained in an amount of 4 wt% to 70 wt%; 4 wt% to 50 wt%; or 4 wt% to 35 wt% relative to 100 wt% of the ink composition.

[0204] According to one embodiment of the present invention, the second solvent is contained in an amount of 20 wt% to 95 wt%; 40 wt% to 95 wt%; or 65 wt% to 95 wt% relative to 100 wt% of the ink composition.

[0205] According to one embodiment of the present invention, the ionic compound containing an 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.

[0206] According to one embodiment of the present invention, the compound represented by the chemical formula 1 is contained at 0.1 wt% to 15 wt%; the first solvent represented by the chemical formula A is contained at 4 wt% to 50 wt%; the second solvent is contained at 40 wt% to 95 wt%; and the ionic compound containing an anionic group represented by the chemical formula 2 is contained at 0.1 wt% to 15 wt% relative to 100 wt% of the ink composition.

[0207] According to one embodiment of the present invention, the compound represented by the chemical formula 1 is contained at 0.1 wt% to 15 wt%; the first solvent represented by the chemical formula A is contained at 4 wt% to 35 wt%; the second solvent is contained at 65 wt% to 95 wt%; and the ionic compound containing an anionic group represented by the chemical formula 2 is contained at 0.1 wt% to 15 wt% relative to 100 wt% of the ink composition.

[0208] In 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 element can be easily manufactured. Specifically, when an organic layer is formed in an organic light-emitting element, a uniform film can be formed.

[0209] The viscosity is a value measured at room temperature using a Brookfield viscometer after dissolving the object to be measured in a first solvent or a mixture of the first and second solvents in any ratio at a concentration of 1 wt% to 3 wt%. In this case, the object to be measured is a compound represented by Chemical Formula 1; or a mixture of the compound represented by Chemical Formula 1 and the above-mentioned ionic compound.

[0210] According to one embodiment of the present invention, the ink composition is in a liquid state. The term "liquid state" means that the ink composition is in a liquid state at normal temperature and normal pressure.

[0211] In one embodiment of the present specification, the ink composition is curable 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.

[0212] In 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 an end 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 an end group capable of forming a polymer by heat, as described above, may be a compound having a molecular weight of 3,000 g / mol or less, but is not limited to the molecular weights exemplified above.

[0213] The monomer having a photocurable group and / or a thermosetting group; or a monomer having 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.

[0214] In 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.

[0215] The pixel containing the ink composition described above will now be described in detail.

[0216] According to an embodiment of the present invention, there is provided a pixel comprising the ink composition or a cured product thereof. The pixel may be included in an organic layer, an organic light emitting diode, or an organic light emitting display device. The organic layer will be described in detail below.

[0217] In one embodiment of the present invention, an organic light-emitting display device includes a plurality of pixels each consisting of red (R), green (G), and blue (B) sub-pixels, and an organic light-emitting diode and a pixel circuit are arranged for each sub-pixel. 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.

[0218] In one embodiment of the present invention, the organic layer, organic light-emitting diode and / or organic light-emitting display device includes a bank that is separated for each sub-pixel and can be ink-applied, or a bank in the form of ink droplets connected within two or more sub-pixels.

[0219] In an embodiment of the present invention, the shape of the bank is not limited. For example, the organic material layer, the organic light emitting diode, or the organic light emitting display device may include a line-shaped bank. The line-shaped bank may define a line-shaped pixel region and / or a sub-pixel region. For another example, the organic material layer, the organic light emitting diode, or the organic light emitting display device may include a separate bank that is not line-shaped. In a typical case, the light emitting layer of 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 sub-pixel, the green sub-pixel, and the blue sub-pixel, respectively. In this case, the pixel may correspond to the pixel or the sub-pixel. As a preferred example, the pixel corresponds to the sub-pixel.

[0220] In 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.

[0221] The organic layer including the above-mentioned pixels will now be described in detail.

[0222] One embodiment of the present invention provides an organic layer including the pixel described above. Since the pixel includes the ink composition or a cured product thereof, it can be said that one embodiment of the present invention provides an organic layer including the ink composition or a cured product thereof.

[0223] In 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 and on which nb pixels are arranged, and the na and nb are each 2 to 10. 4 Integers, 10 to 10 3or an integer between 20 and 10 2 An integer.

[0224] In one embodiment of the present invention, the na and nb are each 2 or more, 5 or more, 10 or more, or 20 or more, and 4 Below, 10 3 Less than or equal to 10 2 The following is the result.

[0225] In 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 10 or less 4 Includes less than 100 pieces.

[0226] In one embodiment of the present invention, the pixels included in the organic layer are arranged in a line, for example, as shown in Figures 4 and 7, a plurality of pixels 1' are arranged in a row to form a line.

[0227] In 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 Figures 4 and 7, 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 organic layer may include as many lines as the number of pixels (n) included in the x-axis.

[0228] In one embodiment of the present invention, the pixels included in the organic layer are arranged in a separated form, not in a line. For example, as shown in FIG. 8, a plurality of pixels may be formed in a separated form.

[0229] In one embodiment of the present invention, the organic layer includes na×nb pixels.

[0230] In one embodiment of the present invention, the organic layer includes a plurality of pixels each having a uniform thickness.

[0231] In one embodiment of the present invention, the organic layer includes an x-axis on which nc pixels are arranged and a y-axis perpendicular to the x-axis and on which nd pixels are arranged, and the nc and nd are each 20 to 10 4 and satisfies the following chemical formula 1. [Formula 1] |X(i')-X(5)|≦5 nm In the above formula 1, X(i') is the average thickness of the [(nd / 2)-4]th to [(nd / 2)+5]th pixels, X(5) is the thickness of the 5th pixel from the edge, If nd is an odd number, (nd / 2) is rounded off to one decimal place.

[0232] In the case where nd is an odd number, for example, if measurements are taken at 25 pixels (that is, nd is 25), X(i') is the average thickness of the 13th to 18th pixels.

[0233] In an embodiment of the present invention, the [(nd / 2)-4]th to [(nd / 2)+5]th pixels refer to pixels located at the center of a plurality of pixels.

[0234] In one embodiment of the present invention, nd is 20 to 10 4 Integer, 20~10 3 or an integer between 20 and 100.

[0235] In one embodiment of the present invention, the thickness of the pixel can be measured by an optical thickness measuring device, such as, but not limited to, an Optical Profiler from Bruker.

[0236] In one embodiment of the present invention, satisfying the formula 1 means that the difference between the average thickness of a pixel located at the center of a plurality of pixels and the thickness of the pixel located 5th from the edge is 5 nm or less. In other words, it means that there is almost no difference in thickness between the center and edge of a pixel. Therefore, satisfying the formula 1 means that the thickness uniformity between pixels is improved.

[0237] In one embodiment of the present invention, the organic layer satisfies the following formula 2. [Formula 2] |X(i')-X(4)|≦5 nm In the formula 2, X(i') is the same as defined in Equation 1, X(4) is the thickness of the fourth pixel from the edge.

[0238] In one embodiment of the present invention, the organic layer satisfies the following formula 3. [Formula 3] |X(i')-X(3)|≦5 nm In the formula 3, X(i') is the same as defined in Equation 1, X(3) is the thickness of the third pixel from the edge.

[0239] In one embodiment of the present invention, the organic layer has a pixel that satisfies the following formula 11 within the second range from the edge. [Formula 11] |Y(20)-Y(80)|≦5 nm In the formula 11, Y(20) is the membrane height in the section that is 20% of the pixel length, and Y(80) is the membrane height in the section that is 80% of the pixel length.

[0240] Satisfying the formula 11 means that the difference between the thin film height of a section (0.2Lx) that is 20% of the length of a pixel having a length Lx and the thin film height of a section (0.8Lx) that is 80% of the length is 5 nm or less. In other words, satisfying the formula 11 means that the thin film in the pixel is formed symmetrically without being tilted to one side.

[0241] If the pixel that satisfies the above formula 11 is within the second pixel from the edge, it means that the shape and thickness of the edge side pixels among the generated pixels are also maintained. Therefore, it can be confirmed that the pixels at the edge and the pixels at the center are generated with little deviation in shape and thickness.

[0242] In one embodiment of the present invention, the pixels included in the organic layer have excellent thickness uniformity both among a plurality of pixels and within one pixel.

[0243] In one embodiment of the present invention, the length (Lx) of the pixel is from 10 μm to 300 μm.

[0244] In the present invention, the edge means both ends on which the ink composition is printed. For example, in Fig. 7 and Fig. 8, when the ink is printed in the direction from (a) to (b) (arrow direction), the portion (a) or (b) is expressed as the edge. Fig. 7 illustrates the ink composition being applied in the vertical direction, but the application direction of the ink composition is not limited thereto. For example, the ink may be applied in the horizontal direction.

[0245] In one embodiment of the present invention, the organic layer is included in an organic light-emitting device.

[0246] In one embodiment of the invention, the organic layer is formed via solution processing.

[0247] In 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, an emitting layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer.

[0248] In 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.

[0249] In 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.

[0250] In a preferred embodiment of the present invention, the organic layer is a hole injection layer, a hole transport layer or an electron blocking layer.

[0251] The organic light-emitting element will be specifically described below.

[0252] One embodiment of the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers is the organic layer described above.

[0253] That is, one embodiment of the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises the ink composition described above or a cured product thereof.

[0254] In 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, a light-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 a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer includes the ink composition or a cured product thereof.

[0255] In 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 a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer includes the ink composition described above or a cured product thereof.

[0256] In one 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 described above or a cured product thereof.

[0257] In one embodiment of the present invention, the organic layer includes na×nb pixels as described above, and the na×nb pixels satisfy formula 1 above.

[0258] A method for manufacturing an organic light-emitting device will be specifically described below.

[0259] One embodiment of the present invention includes the steps of providing a first electrode; forming at least one organic layer on the first electrode; and forming a second electrode on the at least one organic layer; The forming of the organic material layer may include forming the organic material layer using the ink composition described above.

[0260] In one embodiment of the present invention, the step of forming the organic layer using the ink composition is performed using a spin coating method.

[0261] In one embodiment of the present invention, the step of forming an organic layer using the ink composition is performed using a printing method.

[0262] In 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 above-mentioned printing methods.

[0263] In one embodiment of the present invention, the step of forming an organic layer using the ink composition is performed using an ink-jet printing method.

[0264] In one embodiment of the present invention, the step of forming at least one organic layer using the ink composition may be performed by applying the ink composition onto a substrate including a bank or an organic layer, followed by drying or heat treatment.

[0265] As an example, the above-mentioned ink composition may be applied to a substrate including line-shaped banks (line bank inkjet substrate, FIG. 4) (FIG. 5), and then the ink composition may be dried or heat-treated to form a thin film (FIG. 6).

[0266] As another example, the ink composition may be applied to a substrate including banks that do not form lines, with the ink composition being applied to each bank.

[0267] The ink composition according to an embodiment of the present invention is suitable for solution processing due to its structural characteristics, and an organic layer can be formed by a printing method, which is economical in terms of time and cost when manufacturing a device.

[0268] In one embodiment of the present invention, the step of forming an organic material layer on the first electrode may further include one or more depressurization and drying steps. For example, the step of forming at least one organic material layer on the first electrode further includes two depressurization and drying steps. In this case, the first depressurization and drying step is performed at normal pressure to 2×10 -2 Torr, and atmospheric pressures up to 2×10 -2 The time for decompression to torr may be 30 seconds to 600 seconds. Furthermore, the drying stage after the second decompression may be 2×10 -2 torr~2×10 -6 Torr, 2×10 -2 Torr to 2×10 -6 The time required for reducing the pressure to torr may be 30 seconds to 600 seconds.

[0269] In 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 light treatment.

[0270] In one embodiment of the present invention, the step of forming at least one organic layer using the ink composition includes the steps of coating the ink composition on the first electrode or the at least one organic layer; and subjecting the coated ink composition to a heat treatment or a light treatment.

[0271] In one embodiment of the present invention, the heat treatment step may be performed via heat treatment, and the heat treatment temperature in the heat treatment step may be 85°C to 250°C, in one embodiment, 100°C to 250°C, and in another embodiment, 150°C to 250°C.

[0272] In one embodiment of the present invention, the heat treatment time in the heat treatment step may be 10 minutes to 2 hours, in one embodiment, 10 minutes to 1 hour, and in another embodiment, 20 minutes to 1 hour.

[0273] When the step of forming an organic material layer using the ink composition includes the heat treatment or light treatment step, a plurality of the compounds contained in the ink composition may be crosslinked to provide an organic material layer having a thin film structure. In this case, when another layer is laminated on the surface of the organic material layer formed using the ink composition, the organic material layer may be prevented from being dissolved, morphologically affected, or decomposed by a solvent.

[0274] Therefore, when the organic layer is formed by heat-treating or phototreating the ink composition, the resistance to the solvent is increased, and thus, the solution deposition and crosslinking method can be repeatedly performed to form multiple layers, which increases the stability and improves the life characteristics of the device.

[0275] The types of organic layers included in the above-mentioned organic light-emitting element will be specifically described below.

[0276] In one embodiment of the present invention, the organic light-emitting device includes one organic material layer, and at least one of the organic material layers includes the ink composition or a cured product thereof. As an example, the organic material layer including the ink composition or a cured product thereof is a hole injection layer.

[0277] In one embodiment of the present invention, the organic light-emitting device includes two or more organic layers, and at least one of the two or more organic layers includes the ink composition or a cured product thereof. For example, any one of the two or more organic layers includes the ink composition or a cured product thereof, and further includes another organic layer. The other organic layer according to one embodiment does not include the ink composition or a cured product thereof. The other organic layer according to another embodiment further includes the ink composition or a cured product thereof. However, the present invention is not limited to the above examples.

[0278] The two or more organic layers 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, a light 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 means a layer that simultaneously performs hole injection and hole transport, and the electron injection and transport layer means a layer that simultaneously performs electron injection and electron transport. However, the organic layers constituting the group are merely examples and are not limited to the above examples. In addition, the two or more organic layers may include two or more layers that perform the same role as necessary. An organic light emitting device according to an example includes a first hole injection layer and a second hole injection layer. However, the above examples are not limited to the above examples.

[0279] In one embodiment of the present invention, the organic material layer includes a light-emitting layer. As one example, the light-emitting layer includes the ink composition or a cured product thereof. As a specific example, the light-emitting layer includes the ink composition or a cured product thereof as a light-emitting layer host. As another specific example, the light-emitting layer includes the ink composition or a cured product thereof as a light-emitting layer dopant.

[0280] In one embodiment of the present invention, the organic layer includes a hole injection and transport layer, a hole injection layer, a hole transport layer, or 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.

[0281] In one embodiment of the present invention, the organic layer includes a hole injection layer, a hole transport layer, and / or an electron blocking layer. For example, the hole injection layer, the hole transport layer, and / or the electron blocking layer includes the ink composition or a cured product thereof.

[0282] In 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. As an example, the 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. As another example, the 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.

[0283] In one embodiment of the present invention, the organic light-emitting element includes a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, the organic layer including a light-emitting layer, a hole injection layer, and an electron blocking layer, and the hole injection layer or the electron blocking layer includes the ink composition or a cured product thereof.

[0284] The organic layer and the laminated structure of the organic light-emitting device including the organic layer will be specifically described below.

[0285] In one embodiment of the present invention, the organic material layer of the organic light-emitting element has a single-layer structure. For example, the organic material layer of the single-layer structure is provided between a first electrode and a second electrode of the organic light-emitting element, and the organic material layer includes the ink composition or a cured product thereof. In a specific embodiment, the organic material layer of the single-layer structure is a light-emitting layer, and in this case, the light-emitting layer includes the ink composition or a cured product thereof.

[0286] In one embodiment of the present invention, the organic layer of the organic light-emitting element has a multilayer structure in which two or more organic layers are laminated. For example, the organic layer of the multilayer structure is provided between a first electrode and a second electrode of the organic light-emitting element.

[0287] In one embodiment of the present invention, the organic layer of the multilayer structure includes an organic layer other than the light-emitting layer and the light-emitting layer. As an example, the light-emitting layer is provided between the first electrode and the second electrode, and the organic layer other than the light-emitting layer is provided between the first electrode and the light-emitting layer. As another example, the light-emitting layer is provided between the first electrode and the second electrode, and the organic layer other than the light-emitting layer is provided between the light-emitting layer and the second electrode. As another example, the light-emitting layer is provided between the first electrode and the second electrode, any organic layer other than the light-emitting layer is provided between the first electrode and the light-emitting layer, and any organic layer other than the light-emitting layer is provided between the light-emitting layer and the second electrode. However, the structure is merely an example and is not limited to the structure. In addition, the organic layer other than the light-emitting layer may be at least one layer selected from the group consisting of, for example, a hole injection and transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer, but is not limited thereto.

[0288] 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.

[0289] In addition, in general, an electron injection layer, an electron transport layer, or a hole blocking layer in an organic light emitting device is provided between a cathode and a 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.

[0290] In one embodiment of the present invention, the multi-layered organic layer included in the organic light-emitting device includes at least one layer 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 emission layer, the emission layer is provided between a first electrode and a second electrode, the at least one layer is provided between the first electrode and the emission layer, and the at least one layer contains the compound represented by Chemical Formula 1 and / or the first solvent represented by Chemical Formula A.

[0291] The structure of an organic light emitting device according to an embodiment of the present invention is shown in Figure 1. Figure 1 illustrates a 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 Figure 1 may include the ink composition or a cured product thereof, or may be formed using the ink composition.

[0292] FIG. 1 illustrates an organic light emitting device according to one embodiment of the present invention, and the structure of the organic light emitting device according to the present invention is not limited thereto.

[0293] As described above, the organic light-emitting element having a single-layer or multi-layer organic material layer may have, for example, the following laminated 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

[0294] In the above structure, the "electron transport layer / electron injection layer" can be replaced with an "electron injection and transport layer" or a "layer that simultaneously performs electron injection and electron transport."

[0295] In addition, 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."

[0296] In one embodiment of the invention, the first electrode is an anode and the second electrode is a cathode.

[0297] In one embodiment of the invention, the first electrode is a cathode and the second electrode is an anode.

[0298] In one embodiment of the present invention, the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially laminated on a substrate.

[0299] In one embodiment of the present invention, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic layer, and an anode are sequentially laminated on a substrate.

[0300] In one embodiment of the present invention, the organic light-emitting device may be manufactured using materials and methods known in the art, except that at least one of the organic layers is formed using the ink composition described above.

[0301] For example, the organic light emitting device of the present invention can be fabricated by sequentially stacking an anode, an organic layer, and a cathode on a substrate. In this case, a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form an anode, and an organic layer including at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, an electron transport layer, a hole transport and injection layer, and an electron transport and injection layer is formed thereon through a solution process, a deposition process, etc., and then a material usable as a cathode is deposited thereon. In addition to this method, an organic light emitting device can be fabricated by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0302] The anode material is preferably a material having a large work function so that holes can be easily injected into the organic layer, such as metals or alloys thereof, such as vanadium, chromium, copper, zinc, and gold; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO. 2 These include, but are not limited to: combinations of metals such as Sb and oxides; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0303] The cathode material is preferably a material with a small work function so that electrons can be easily injected into the organic layer, such as metals or alloys thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; LiF / Al, or LiO 2 / Al, but is not limited thereto.

[0304] The light-emitting layer may include a host material and / or a dopant material.

[0305] 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.

[0306] The dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and periflanthene, which have arylamine groups. Styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. Metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0307] The hole injection layer is a layer that receives holes from the electrode. The hole injection material preferably has the ability to transport holes, and has an excellent effect of receiving holes from the anode and injecting holes into the light emitting layer or light emitting material. In addition, a material that is excellent in the ability to prevent the movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material is preferable. In addition, a material that is excellent in the ability to form a thin film is preferable. In addition, it is preferable that the HOMO of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrin, oligothiophene, and arylamine-based organic materials; hexanitrile hexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; polythiophene-based conductive polymers such as anthraquinone and polyaniline; and the compound of the above-mentioned Chemical Formula 1.

[0308] In one embodiment of the present invention, the hole injection layer is formed from the ink composition described above or a cured product thereof.

[0309] In one embodiment of the present invention, the compound of Formula 1 is included as a host in the hole injection layer.

[0310] In one embodiment of the invention, the ionic compound is included as a dopant in the hole injection layer.

[0311] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and may be a single layer 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 the hole injection layer and transfer them to the light emitting layer, and is preferably a material with high mobility for holes. Specific examples of the hole transport material include, but are not limited to, arylamine organic compounds, carbazole compounds, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0312] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. As the electron transport material, a material that can effectively inject electrons from the cathode and transfer them to the light emitting layer and has high mobility for electrons is preferable. Specific examples include Al complex of 8-hydroxyquinoline; Alq 3 The electron transport layer may be used with any desired cathode material, as used according to the prior art. In particular, suitable cathode materials are those that have a low work function and are usually followed by an aluminum or silver layer. In particular, they include cesium, barium, calcium, ytterbium, samarium, etc., each followed by an aluminum or silver layer.

[0313] The electron injection layer is a layer that receives electrons from the electrode. As the electron injection material, those that have excellent electron transporting ability, electron receiving effect from the cathode, and excellent electron injection effect to the light emitting layer or light emitting material are preferable. In addition, those that prevent excitons generated in the light emitting layer from moving to the hole injection layer and have excellent thin film forming ability are preferable. Specifically, there are fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but are not limited thereto. Examples of the metal complex compound include, but are not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h]quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato) chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolate) gallium, bis(2-methyl-8-quinolinato) (1-naphtholato) aluminum, and bis(2-methyl-8-quinolinato) (2-naphtholato) gallium.

[0314] The electron blocking layer is a layer that can improve the life and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer via the light emitting layer. The electron blocking layer can be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and a layer that simultaneously injects and transports holes, using the compound of Chemical Formula 2.

[0315] The hole blocking layer is a layer that blocks holes from reaching the cathode and can be generally formed under the same conditions as the electron injection layer. Specific examples of the hole blocking layer material include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0316] The hole injection and transport layers may include the hole injection layer and hole transport layer materials described above.

[0317] The electron injection and transport layer may comprise the electron injection layer and hole transport layer materials described above.

[0318] When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0319] The organic light emitting device according to the present invention may be front-emitting, back-emitting or double-sided emitting, depending on the materials used.

[0320] 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.

[0321] 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 coat 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. EXAMPLES

[0322] Hereinafter, the present invention will be described in detail with reference to examples in order to specifically explain the present invention. However, the examples of the present invention can be modified in various different forms, and the scope of the present invention is not to 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 having average knowledge in the art.

[0323] <Synthesis Example A. Preparation of Compound> [Synthesis Example A-1. Synthesis of Compound H-1] (1) Synthesis of intermediate 1-1 [ka]

[0324] 1-Bromo-4-fluorobenzene (27.9 mL, 255 mmol, 1.7 eq) was added to tetrahydrofuran (THF) (500 mL). After replacing with nitrogen, the mixture was cooled to -78 °C. n-Butyl lithium (n-BuLi) (2.5 M in hexane) (96 mL, 240 mmol, 1.6 eq) was added to a dropping funnel and slowly added to the reaction mixture, which was then stirred at -78 °C for 30 minutes. 2-Bromofluorenone (38.9 g, 150 mmol) was added. The mixture was slowly raised to room temperature (RT) and stirred overnight. Distilled water was added to terminate the reaction, and the mixture was extracted with ethyl acetate and water. The organic layer was collected and then magnesium sulfate (MgSO 4 The organic layer was dried using hexanes) and filtered. The filtrate was dried on a vacuum rotary evaporator to remove the organic solvent, yielding intermediate 1-1.

[0325] (2) Synthesis of intermediate 1-2 [ka]

[0326] Intermediate 1-1 (53 g, 150 mmol) and phenol (70.6 g, 750 mmol, 5 eq) were placed in a round-bottom flask (RBF). 3 SO 3 H) (214 mL, 0.7 M) was added, and the mixture was stirred at 60 °C for 4 hours. Ice water was added, and the mixture was extracted with ethyl acetate and water. The organic layer was collected, and then MgSO 4 The organic layer was dried using hexane and filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, the mixture was crystallized under dichloromethane / heptane conditions to obtain 40.6 g of intermediate 1-2.

[0327] (3) Synthesis of intermediate 1-3 [ka]

[0328] Intermediate 1-2 (40 g, 92.7 mmol), 4-nitrobenzaldehyde (21.2 g, 139 mmol, 1.5 eq), copper(II) acetate (Cu(OAc) 2 ) (842 mg, 4.64 mmol, 5 mol%), Cs carbonate (Cs 2 CO 3 ) (45.3 g, 139 mmol, 1.5 eq) was placed in a RBF. Dimethylformamide (DMF) (310 mL) was added and stirred at 100 °C for 4 hours. Extraction was performed with ethyl acetate and water, and the organic layer was collected, followed by addition of MgSO 4 The organic layer was dried using hexane and then filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, the mixture was crystallized under dichloromethane / heptane (DCM / Heptane) conditions to obtain 38.7 g of intermediate 1-3.

[0329] (4) Synthesis of intermediate 1-4 [ka]

[0330] Methyltriphenylphosphonium bromide (CH 3 PPh 3 Br) (51.6 g, 144.6 mmol, 2 eq), potassium tertiary-butoxide (KOtBu) (16.2 g, 144.6 mmol, 2 eq), and THF (217 mL) were added to a RBF, and then cooled to 0 °C. A solution of intermediate 1-3 (38.7 g, 72.3 mmol) dissolved in tetrahydrofuran (THF) (144 mL) was added to the reaction mixture. The 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, followed by addition of MgSO 4 The organic layer was dried using a vacuum rotary evaporator and then filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, the mixture was crystallized under dichloromethane / ethanol (DCM / EtOH) conditions to obtain 33.7 g of intermediate 1-4.

[0331] (5) Synthesis of compound H-1 [ka]

[0332] Compound I1 (1.29 g, 2.5 mmol), intermediate 1-4 (2.93 g, 5.5 mmol), bis(tri-tert-butylphosphine)palladium(0) (Pd(PtBu 3 ) 2 ) (64 mg, 0.125 mmol, 5 mol%) and sodium tert-butoxide (NaOtBu) (961 mg, 10 mmol, 4 eq) were placed in a RBF. After replacing with nitrogen, toluene (12.5 mL) was added and stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, and the organic layer was collected, followed by addition of MgSO 4 The organic layer was dried using a vacuum rotary evaporator and then filtered. The filtrate was dried using a vacuum rotary evaporator to remove the organic solvent. After column purification, the mixture was crystallized under DCM / EtOH conditions to obtain 2.8 g of compound H-1. The synthesis of compound H-1 was confirmed by LC-MS and NMR. MS: [M+H] + =1584 NMR measurement value of compound H-1: 1H NMR(500MHz,DMSO-d6)δ8.02(m,2H), 7.86-7.69(m,10H), 7.44-7.33(m,8H), 7.31-7.15(m,12H), 7.01-6.91(m, 8H), 6.87-6.81(m,12H), 6.78-6.65(m,8H), 6.55(d,4H), 6.50(m,2H), 6.35(m,2H), 5.71(dd,2H), 5.18(dd,2H)

[0333] <Synthesis Example A-2. Synthesis of Compound H-2> [ka]

[0334] In (5) of Synthesis Example A-1, except that compound I2 was used instead of compound I1, the same method as Synthesis Example A-1 was used to obtain 2.9 g of compound H-2. The synthesis of compound H-2 was confirmed by LC-MS and NMR. MS: [M+H] + =1736 NMR measurement value of compound H-2: 1 H NMR(500MHz,DMSO-d6)δ8.07(m,2H), 7.98(m,2H), 7.82-7.67(m,12H), 7.47(m,2H), 7.39-7.22(m,20H) ), 7.09-6.93(m,24H), 6.89-6.84(m,6H), 6.79(m,2H), 6.64-6.50(m,6H), 5.62(dd,2H), 5.12(dd,2H)

[0335] <Synthesis Example A-3. Synthesis of Compound H-3> [ka]

[0336] In (5) of Synthesis Example A-1, except that compound I3 was used instead of compound I1, the same method as Synthesis Example A-1 was used to obtain 2.6 g of compound H-3. LC-MS and NMR confirmed that compound H-3 was synthesized. MS: [M+H] + =1422 NMR measurement value of compound H-3: 1 H NMR(500MHz,DMSO-d6)δ8.02(m,2H), 7.87-7.70(m,8H), 7.47-7.32(m,8H), 7.31-7.15(m,10H), 7.05-6.90(m, 8H), 6.90-6.85(m,12H), 6.77-6.65(m,8H), 6.53(d,4H), 6.51(m,2H), 6.36(m,2H), 5.71(dd,2H), 5.18(dd,2H)

[0337] <Synthesis Example A-4. Synthesis of Compound H-4> (1) Synthesis of intermediate 2-1 [ka]

[0338] Intermediate 2-1 was produced in the same manner as in Synthesis Example A-1(1), except that 1-bromo-2,6-difluorobenzene (29.4 mL, 255 mmol, 1.7 eq) was used instead of 1-bromo-4-fluorobenzene in Synthesis Example A-1(1).

[0339] (2) Synthesis of intermediate 2-2 [ka]

[0340] The same procedure as in Synthesis Example A-1(2) was repeated except that Intermediate 2-1 (56 g, 150 mmol) was used instead of Intermediate 1-1, to obtain 45.2 g of Intermediate 2-2.

[0341] (3) Synthesis of intermediate 2-3 [ka]

[0342] The same procedure as in Synthesis Example A-1(3) was repeated except that Intermediate 2-2 (45.2 g, 100 mmol) was used instead of Intermediate 1-2, to obtain 39.8 g of Intermediate 2-3.

[0343] (4) Synthesis of intermediate 2-4 [ka]

[0344] The same procedure as in Synthesis Example A-1(4) was repeated except that Intermediate 2-3 (39.8 g, 72 mmol) was used instead of Intermediate 1-3 in Synthesis Example A-1(4), to obtain 34.8 g of Intermediate 2-4.

[0345] (5) Synthesis of compound H-4 [ka]

[0346] In the above Synthesis Example A-1 (5), compound I4 (1.85 g, 2.5 mmol) and intermediate 2-4 (2.93 g, 5.5 mmol) were used instead of compound I1 and intermediate 1-4, and the same procedure as in Synthesis Example A-1 (5) was followed to obtain 3.5 g of compound H-4. LC-MS and NMR confirmed that compound H-4 had been synthesized. MS: [M+H] + =1873 NMR measurement value of compound H-4: 1 H NMR(500MHz,DMSO-d6)δ8.28(d,2H), 8.10(m,2H), 7.90-7.67(m,14H), 7.46(m,2H), 7.38-7.20(m,20H) ), 7.09-6.93(m,24H), 6.89-6.84(m,6H), 6.76(m,2H), 6.62-6.73(m,6H), 5.62(dd,2H), 5.12(dd,2H)

[0347] <Synthesis Example A-5. Synthesis of Compound H-5> [ka]

[0348] In the above Synthesis Example A-1 (5), compound I5 (1.85 g, 2.5 mmol) and intermediate 2-4 (2.93 g, 5.5 mmol) were used instead of compound I1 and intermediate 1-4, and the same procedure as in Synthesis Example A-1 (5) was used to obtain 2.6 g of compound H-5. LC-MS and NMR confirmed that compound H-5 was synthesized. MS: [M+H] + =1682 NMR measurement value of compound H-5: 1 H NMR(500MHz,DMSO-d6)δ8.04(m,2H), 7.87-7.70(m,8H), 7.47-7.32(m,10H), 7.31-7.15(m,8H), 7.05-6.90(m, 8H), 6.90-6.85(m,12H), 6.77-6.65(m,8H), 6.53(d,4H), 6.51(m,2H), 6.36(m,2H), 5.71(dd,2H), 5.18(dd,2H)

[0349] <Synthesis Example A-6. Synthesis of Compound H-6> [ka]

[0350] In (5) of Synthesis Example A-1, except that compound I6 was used instead of compound I1, the same method as Synthesis Example A-1 was used to obtain 2.6 g of compound H-6. The synthesis of compound H-6 was confirmed by LC-MS and NMR. MS: [M+H] + =1584 NMR measurement value of compound H-6: 1 H NMR(500MHz,DMSO-d6)δ7.93(m,2H), 7.80-7.73(m,10H), 7.41-7.25(m,18H), 7 .09-6.80(m,32H), 6.70-6.61(m,4H), 6.45(m,2H), 5.68(dd,2H), 5.18(dd,2H)

[0351] <Synthesis Example A-7. Synthesis of Compound H-7> (1) Synthesis of intermediate 3-1 [ka]

[0352] Intermediate 3-1 was produced in the same manner as in Synthesis Example A-1(1), except that 1-bromo-2,3,4,5,6-pentafluorobenzene (31.8 mL, 255 mmol) was used instead of 1-bromo-4-fluorobenzene in Synthesis Example A-1(1).

[0353] (2) Synthesis of intermediate 3-2 [ka]

[0354] Intermediate 3-2 (52.8 g) was obtained by the same method as in Synthesis Example A-1(2), except that Intermediate 3-1 (64.1 g, 150 mmol) was used instead of Intermediate 1-1 in Synthesis Example A-1(2).

[0355] (3) Synthesis of intermediate 3-3 [ka]

[0356] The same procedure as in Synthesis Example A-1(3) was repeated except that Intermediate 3-2 (50.3 g, 100 mmol) was used instead of Intermediate 1-2, to obtain 48.6 g of Intermediate 3-3.

[0357] (4) Synthesis of intermediate 3-4 [ka]

[0358] Intermediate 3-4 (31 g) was obtained by the same method as in Synthesis Example A-1(4), except that Intermediate 3-3 (43.7 g, 72 mmol) was used instead of Intermediate 1-3 in Synthesis Example A-1(4).

[0359] (5) Synthesis of compound H-7 [ka]

[0360] In the above Synthesis Example A-1 (5), compound I7 (1.67 g, 2.5 mmol) and intermediate 3-4 (3.3 g, 5.5 mmol) were used instead of compound I1 and intermediate 1-4, and the same procedure as in Synthesis Example A-1 (5) was used to obtain 2.8 g of compound H-7. LC-MS and NMR confirmed that compound H-7 had been synthesized. MS: [M+H] + =1717 NMR measurement value of compound H-7: 1 H NMR(500MHz,DMSO-d6)δ8.08(m,2H), 8.02(m,2H), 7.87-7.70(m,10H), 7.47-7.32(m,10H), 7.15(m,2H), 7.05-6.90 (m,8H), 6.90-6.85(m,12H), 6.77-6.65(m,8H), 6.53(d,4H), 6.51(m,2H), 6.36(m,2H), 5.71(dd,2H), 5.18(dd,2H)

[0361] <Synthesis Example B. Production of Ionic Compounds> [Synthesis Example B-1. Preparation of Compound DA] (1) Preparation of Compound F-1 [ka]

[0362] 1-Bromo-2,3,5,6-tetrafluoro-4-vinylbenzene (2 g, 7.8428 mmol) and 20 mL of THF were placed in a 50 mL round-bottom flask and stirred at -78 °C for 30 minutes. n-BuLi (3.45 mL, 8.6271 mmol, 2.5 M in hexane) was slowly added to the solution and stirred at -78 °C for 30 minutes. BCl 3 (2.6mL, 2.6142mmol, 1M in heptane solution) was added at -78℃ over 15 minutes. The temperature was slowly raised to room temperature, and the reaction solution was stirred for 1 day, after which 30mL of water was added. The synthesized material was extracted with ethyl acetate (EA) (3×10mL), and the solvent was completely removed. Water was completely removed using a Dean-Stark column using benzene, and the solid was filtered to produce 800mg of compound F-1. (Yield: 43%)

[0363] (2) Preparation of compound DA [ka]

[0364] In a 25 mL round-bottom flask, compound F-1 (400 mg, 0.5569 mmol), diphenyliodonium chloride (176 mg, 0.5569 mmol), and H 2 10 mL of O2 and 10 mL of acetone were added and stirred vigorously for 30 minutes. The mixture was extracted with dichloromethane to remove the solvent and dried. After removing all the solvent, water was completely removed using a Dean-Stark column with benzene, and the solid was filtered to produce 340 mg of the target compound DA (yield: 28%). The synthesis of the compound was confirmed by LC-MS and NMR. MS:[MH]-=711(negative mode) MS: [M+H] + = 281 (positive mode) FIG. 2 shows the NMR measurement results of compound DA.

[0365] [Synthesis Example B-2. Preparation of Compound DB] (1) Preparation of Compound F-2 [ka]

[0366] In a 100 mL round-bottom flask, add Mg (193 mg, 7.9208 mmol), I 2 (4 mg) and tetrahydrofuran (THF) (10 mL) were added and stirred for 30 minutes. 4-Bromostyrene (1.04 mL, 7.9208 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, confirming that Mg had dissolved. 5 mL of ether was added to dilute the reaction solution. Tris(pentafluorophenyl)borane (1 g, 3.9604 mmol) was dissolved in 5 mL of ether and slowly added to the reaction solution over 30 minutes. The solution was stirred for 1 day. Na 2 CO 3 (0.1M, 80mL, 8.0mmol) was slowly added to the reaction solution. The organic matter was extracted with ethyl acetate (EA) and MgSO 4 The residue was removed by ethanol. To further remove the remaining water and impurities, the mixture was distilled with benzene using a Dean-Stark column. When about 10 mL of solvent remained, the solution was cooled and filtered to produce 1.6 g of compound F-2 (yield: 64%).

[0367] (2) Creation of a compound database [ka]

[0368] In a 25 mL round-bottom flask, compound F-2 (100 mg, 0.1567 mmol), 10 mL of distilled water, and pH 2 ICl (60 mg, 0.1881 mmol) was added and stirred for 1 hour. 15 mL of acetone was added to the reaction solution to produce a precipitate, which was filtered and dried to produce 140 mg of compound DB (yield: 100%). The synthesis of the compound was confirmed by LC-MS and NMR. MS:[MH]-=615(negative mode) MS: [M+H] + = 281 (positive mode) FIG. 3 shows the NMR measurement results of compound DB.

[0369] <Production of Ink Composition> [Production Example 1. Production of Ink Composition 1] Compound H-3 prepared in Synthesis Example A-3 and compound DA prepared in Synthesis Example B-1 were mixed in a weight ratio of 8:2 to prepare mixture 1. Then, mixture 1 was added to a solvent in which 3-isopropylbiphenyl (first solvent represented by chemical formula A) and dibutyl oxalate (additional solvent) were mixed at 20 wt % and 80 wt %, respectively, to a concentration of 2 wt %, and the mixture was stirred for 24 hours to prepare ink composition 1.

[0370] [Production Examples 2 to 71. Production of Ink Compositions 2 to 71] Ink compositions 2 to 71 were prepared in the same manner as in Preparation Example 1, except that the compounds H-3, DA, the first solvent, and the additional solvent were each the substances shown in Table 1 below. In this case, when two types of additional solvents were used, the solvent of formula A, the first additional solvent, and the second additional solvent were mixed at 20 wt %, 50 wt %, and 30 wt %, respectively.

[0371] *Hole injection layer host compound (HIL host) [ka]

[0372] *Hole injection layer dopant compound (HIL dopant) [ka]

[0373] [Table 1]

[0374] [Table 2]

[0375] [Table 3]

[0376] [Table 4]

[0377] [Table 5]

[0378] [Table 6]

[0379] <Experimental Example A> Example 1-1 The ink composition 1 was printed on a substrate on which a plurality of pixels were formed in lines. The printed substrate was placed in a vacuum chamber and subjected to high vacuum (1×10 -6 Torr or less. 2 The thin film was cured by heat treatment for 30 minutes under conditions of 230° C. hot plate and 100% aqueous solution of 100% ethanol. FIG. 4 shows a line bank inkjet substrate onto which the ink composition was applied. FIG. 5 shows that the ink composition was applied to a line bank inkjet substrate. FIG. 6 shows that the ink composition was formed into a thin film on a line bank inkjet substrate. Fig. 7 shows a plan view of an organic layer on which a line bank is formed. In Fig. 7, an ink composition is printed from (a) to (b) (arrow direction), and at this time, the (a) or (b) portion is expressed as an edge.

[0380] [Examples 1-2 to 1-45 and Comparative Examples 1-1 to 1-24] An organic layer was prepared in the same manner as in Example 1-1, except that the ink composition shown in Table 2 below was used instead of the ink composition 1 in Example 1-1, and the thickness of the pixel was measured.

[0381] In Table 2 below, one line was selected from a plurality of pixels formed as a thin film using the ink compositions prepared in Examples 1-1 to 1-45 and Comparative Examples 1-1 to 1-24, and the average thickness of 10 pixels located at the center of the line was compared with the thickness of a pixel located at the edge of the line, and the number of pixels from the edge where the thin film had a thickness deviation of 5 nm or less was shown.

[0382] At this time, the thickness of the pixels contained in the cured thin film was measured using an optical thickness measuring device, an optical profiler (model name: ContourGT-I) manufactured by Bruker.

[0383] Specifically, in a line bank in which 70 pixels are formed in a row, the average thickness of the 31st to 40th pixels was compared with the thickness of the i-th pixel from the edge, and the minimum value of i within ±5 nm is shown in Table 2. In this case, the smaller the i number, the more uniform the thickness of the thin film is formed up to the edge (i.e., the thickness uniformity is improved).

[0384] [Table 7]

[0385] [Table 8]

[0386] [Table 9]

[0387] [Table 10]

[0388] From Table 2, it can be seen that in Examples 1-1 to 1-45, the pixels showing the center average thickness ±5 nm are located 5th or less from the edge, whereas in Comparative Examples 1-1 to 1-24, they are located 6th or more.

[0389] In this regard, Fig. 9 and Fig. 10 show the thickness uniformity characteristics of pixels according to the embodiment of the present invention. Specifically, Fig. 9 shows the thickness uniformity of pixels measured in Example 1-1, and Fig. 10 shows the thickness uniformity of pixels measured in Comparative Example 1-1. In Fig. 9 and Fig. 10, the horizontal axis indicates the distance between pixels (μm), and the vertical axis indicates the thickness of pixels (nm). As can be seen from Fig. 9 and Fig. 10, in Example 1-1 (Fig. 9) using the ink composition according to one embodiment of the present invention, the number of pixels with a thick thin film formed is small even at the edge portion, whereas in Comparative Example 1-1 (Fig. 10) not using the ink composition according to one embodiment of the present invention, the number of pixels with a thick thin film formed increases toward the edge portion, and the thickness of the thin film also increases.

[0390] As a result, when an ink composition according to an embodiment of the present invention is used, the thickness uniformity is improved, and therefore, when used in an organic layer in an organic light-emitting device, factors that affect the interference conditions of light emitted according to the thickness are reduced, and excellent light emission and / or color development effects can be expected. On the other hand, when an ink composition not corresponding to the present invention is used, the thickness difference between pixels is large and the thickness uniformity is uneven, so that it is expected that the performance of the device will be deteriorated when applied to an organic layer in an organic light-emitting device.

[0391] Example 2-1 The ink composition 1 was printed on a substrate on which 30×60 pixels were formed. The printed substrate was placed in a vacuum chamber and subjected to high vacuum (1×10 -6 Torr or less. 2The thin film was cured by heat treatment for 30 minutes under conditions of 230°C hot plate and 100°C ambient atmosphere. Fig. 8 is a plan view of an organic layer in which separated banks are formed. In Fig. 8, the ink composition is printed from (a) to (b) (arrow direction), and at this time, the (a) or (b) portion is expressed as an edge.

[0392] [Examples 2-2 to 2-31 and Comparative Examples 2-1 to 2-14] An organic layer was prepared in the same manner as in Example 2-1, except that the ink composition shown in Table 3 below was used instead of the ink composition 1 in Example 2-1, and the difference in the height of the thin film in the pixel was measured. At this time, the step height of the thin film within the pixel was measured using a thin film thickness measuring device, an optical profiler (model name: ContourGT-I) manufactured by Bruker. The difference in the height of the thin film between the section that is 20% and the section that is 80% of the pixel length within one pixel was measured, and the minimum value of i where the value was ±5 nm is shown in Table 3 below. In this case, i means the i-th pixel from the edge. Also, the smaller the number of i, the more uniform the thickness of the thin film within the pixel is formed up to the area closer to the edge (i.e., the thickness uniformity is improved).

[0393] [Table 11]

[0394] [Table 12]

[0395] The difference in height between the section that is 20% of the pixel length and the section that is 80% of the pixel length (i.e., the absolute value of the height difference is 5 nm or less) means that the thickness of the thin film is formed uniformly in the pixel.

[0396] It can be seen from Table 3 that in Examples 2-1 to 2-31, the thin film in the pixel was formed symmetrically without tilting to one side even in the pixel closer to the edge portion, compared to Comparative Examples 2-1 to 2-14. That is, it can be seen that when the ink composition according to one embodiment of the present invention was applied, the thin film was formed with a uniform thickness even in the pixel closer to the edge than when the other ink compositions were applied.

[0397] As a result, the ink composition of the present invention is used in an organic layer in an organic light-emitting device, and is expected to reduce factors that affect the interference conditions of light emitted depending on the thickness, thereby providing excellent light emission and / or color development effects. On the other hand, when an ink composition not corresponding to the present invention is used, the thin film on the edge side is not formed uniformly, and therefore it is expected that the performance of the device will decrease when the ink composition is applied to an organic layer in an organic light-emitting device.

[0398] <Experimental Example B> Example 3-1 A glass substrate on which a 700 Å-thick ITO (indium tin oxide) thin film was coated and a hydrophobic bank patterned thereon was washed with distilled water for 30 minutes and then dried on a hot plate at 230° C. for 10 minutes. Ink composition 1 in Table 1 was inkjet printed on the washed substrate on which the bank pattern was formed, and then heat-treated at 230° C. for 30 minutes to form a hole injection layer with a thickness of 30 nm. An ink in which an α-NPD compound was dissolved in cyclohexylbenzene at a concentration of 2 wt% was inkjet printed on the hole injection layer to form a hole transport layer with a thickness of 40 nm. After that, the substrate was transferred to a vacuum evaporator, and a 20 nm-thickness light-emitting layer was formed by vacuum-depositing the following ADN compound and the following DPAVBi compound on the hole transport layer at a weight ratio of 20:1 (ADN:DPAVBi). The following BCP compound was vacuum-deposited on the light-emitting 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 was deposited to a thickness of 100 nm on the electron injecting and transporting layer to form a cathode, thereby completing an organic light-emitting device.

[0399] [ka]

[0400] [Examples 3-2 to 3-46] An organic light emitting device was manufactured in the same manner as in Example 3-1, except that the ink composition in Table 4 below was used instead of the ink composition 1 in Example 3-1.

[0401] [Table 13]

[0402] [Table 14]

[0403] It was confirmed that the organic light-emitting devices prepared in Examples 3-1 to 3-46 were driven, which confirmed that the ink composition according to the embodiment of the present invention is applicable to the organic light-emitting devices.

[0404] [Comparative Examples 3-1 to 3-4] Ink compositions 72 to 75 were prepared in the same manner as in Preparation Example 1, except that the compounds H-3, DA, the first solvent and the additional solvent were each the substances shown in Table 5 below. Thereafter, an organic light emitting device was manufactured in the same manner as in Example 3-1, except that the ink composition in Table 6 below was used instead of the ink composition 1 in Example 3-1.

[0405] The structures of compounds X-1 to X-4 used in Table 5 below are as follows. [ka]

[0406] [Table 15]

[0407] The efficiency and lifetime of the organic light emitting devices prepared in Examples 3-1, 3-17, 3-29, and 3-31 and the organic light emitting devices prepared in Comparative Examples 3-1 to 3-4 are compared and shown in Table 6 below.

[0408] The efficiency relative values ​​and life relative values ​​in Table 6 below were determined as follows. *Efficiency relative value: Efficiency of Example X / Efficiency of Examples 3-29 *T95 relative value: T95 of Example X / T95 of Examples 3-29 (Example X: Examples 3-1, 3-17, 3-29, 3-31, Comparative Examples 3-1, 3-2, 3-3, or 3-4) In this case, T95 indicates the life span, and is the time it takes for the brightness to decrease to 95% of the initial brightness under a constant current condition of 1000 nit.

[0409] [Table 16]

[0410] From Tables 5 and 6, it can be seen that when the host is changed in the ink composition of the present invention, the efficiency and lifespan of the organic light emitting device are reduced. [Explanation of symbols]

[0411] 1'...pixel 101... Substrate 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 first solvent represented by the following chemical formula A: 【Chemistry 1】 In the above Chemical Formula 1 and A, Y1 to Y10 are the same or different and each independently represents 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; Cy1 to Cy4 are the same or different and each independently represents a substituted or unsubstituted hydrocarbon ring group; Z1 and Z2 are the same or different and each independently represents O, S, Se or NR; L is a substituted or unsubstituted divalent hydrocarbon ring group; or a substituted or unsubstituted divalent heterocyclic group; L1 to L4 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group; L10 and L11 are the same or different and each independently represents a direct bond; or a substituted or unsubstituted arylene group; X1 and X2 are the same or different and each independently represents a curable group; R and R1 to R4 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; [0046] r1 and r2 each represent an integer of 0 to 4. When r1 and r2 each represent an integer of 2 or more, the two or more substituents in the brackets are the same or different from each other. f1 and f2 are each an integer from 1 to 5, r1+f1 is 5 or less, and r2+f2 is 5 or less; Each of r3 and r4 is an integer of 1 to 7, and when each of r3 and r4 is 2 or more, the two or more substituents in the brackets are the same or different.

2. The ink composition according to claim 1 , wherein the curable group has any one of the following structures: 【Chemistry 2】 In the above structure, R102 and R104 are the same or different and each independently represents hydrogen; deuterium; or a substituted or unsubstituted alkyl group; L101 to L108 are the same or different and each independently represents a direct bond; —O—; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group; Each of l104 to l108 is an integer of 1 to 10, and when each of l104 to l108 is 2 or more, the substituents in the two or more brackets are the same or different from each other, 【Chemistry 3】 is a site that is bonded to Chemical Formula 1.

3. The ink composition according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1: 【Chemistry 4】 In the above Chemical Formula 1-1, The definitions of Cy1 to Cy4, Z1, Z2, L, L1 to L4, L10, L11, X1, X2, R1 to R4, r1 to r4, f1 and f2 are the same as those in Chemical Formula 1.

4. The ink composition according to claim 1 , wherein L is any one of the following structures: 【Chemistry 5】 In the above structure, R10 to R31 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; r10 to r21 each represents an integer of 1 to 4; r22, r23, r28, and r29 each represents an integer of 1 to 3; r24 and r25 each represents an integer of 1 to 7; r26 is an integer of 1 to 8; and r27 is an integer of 1 to 6; when r10 to r29 each represents 2 or more, the two or more substituents in parentheses are the same or different from each other; 【Chemistry 6】 is the site of attachment to Chemical Formula 1.

5. 2. The ink composition according to claim 1, wherein Cy1 to Cy4 are the same or different and each independently represents a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring.

6. 2. The ink composition according to claim 1, wherein Y1 to Y10 are the same or different and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

7. The ink composition according to claim 1 , wherein the first solvent represented by the chemical formula A has any one of the following structures: 【Chemistry 7】

8. The ink composition according to claim 1 , wherein the compound represented by Chemical Formula 1 has any one of the following structures: 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 。

9. The ink composition further comprises a second solvent, The ink composition according to claim 1, wherein the second solvent includes at least one of a solvent represented by any one of the following chemical formulas B to D, methoxytoluene, and tetralin: 【Chemistry 14】 In the above chemical formulas B to D, L50 is a direct bond; or an alkylene group; L51 and L53 to L55 are the same or different and each independently represents a direct bond; —O—; or a substituted or unsubstituted alkylene group; L52 is -COO-, R50, R51, and R54 to R56 are the same or different and each independently represents a substituted or unsubstituted alkyl group; R53 is hydrogen; deuterium; an alkoxy group; or a substituted or unsubstituted alkyl group; a1 is 0 or 1; r53 is an integer of 1 to 5, and when r53 is 2 or more, the two or more R53's are the same or different from each other, Each of l50, l51, and l53 to l55 is an integer of 1 to 10, and when each of l50, l51, and l53 to l55 is 2 or more, the structures in the two or more brackets are the same or different from each other.

10. The boiling point of the first solvent is 250° C. to 350° C. The boiling point of the second solvent is 180° C. to 280° C. The ink composition of claim 9 , wherein the boiling point of the first solvent is higher than the boiling point of the second solvent.

11. The ink composition according to claim 1 , further comprising an ionic compound having an anionic group represented by the following chemical formula 2: 【Chemistry 15】 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 a hydrogen atom; a deuterium atom; a halogen group; a nitro group; a cyano group; an amino group; -OR221; -SR222; or -SO ３ R223; -COOR224; -OC(O)R225; -C(O)NR226R227; -C(O)R228; 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, R221 to R228 are the same or different and each independently represents hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

12. The ink composition according to claim 11, wherein the chemical formula 2 is any one of the following structures: 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 In the above structure, n1 is an integer from 1 to 3, m1 is an integer from 1 to 3, and n1+m1=4; n2 is an integer from 0 to 3, m2 is an integer from 1 to 4, and n2+m2=4; M1 is a deuterium atom; a halogen group; a nitro group; a cyano group; an amino group; -OR221; -SR222; ３ R223; -COOR224; -OC(O)R225; -C(O)NR226R227; -C(O)R228; 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, R221 to R228 are the same or different and each independently represents hydrogen; deuterium; or a substituted or unsubstituted alkyl group; i is an integer of 1 to 4, and when i is 2 or more, two or more M1's are the same or different.

13. The ink composition according to claim 11, wherein the ionic compound further comprises a cationic group, and the cationic group is any one of a monovalent cationic group, an onium compound, or the following structure: 【Chemistry 19】 In the above structure, Q30 to Q105 are the same or different and each independently represents hydrogen; deuterium; a cyano group; a nitro group; a halogen group; a hydroxyl group; -COOR250; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a curable group; R250 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group; x is an integer from 0 to 10; p1 is 1 or 2, q1 is 0 or 1, and p1+q1=2.

14. The ink composition according to claim 11, wherein the ionic compound is represented by any one of the following chemical formulas D-1 to D-37: 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 。

15. 2. The ink composition of 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.

16. A pixel comprising the ink composition according to any one of claims 1 to 15 or a cured product thereof.

17. An organic layer comprising the pixel of claim 16.

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

19. 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 18 , 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.

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