Ink composition, organic material layer comprising same, and organic light-emitting device comprising same

Abstract

The present invention relates to an ink composition, an organic material layer comprising the same, and an organic light emitting device comprising the same.

Description

Technical Field

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2022-0120824 filed in 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 material layer containing the same, and an organic light-emitting device containing the same. Background Art

[0003] The organic light emitting phenomenon is one of the examples of converting electric current into visible light through the internal process of specific organic molecules. The principle of the organic light emitting phenomenon is as follows. When the organic material layer is arranged between the anode and the cathode and a current is applied between the two electrodes, electrons and holes are injected into the organic material layer from the cathode and the anode, respectively. The electrons and holes injected into the organic material layer recombine to form excitons, and the excitons fall to the ground state again to emit light. An organic light emitting device using this principle can generally be composed of a cathode, an anode, and an organic material layer (e.g., a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, an electron transport layer, an electron blocking layer, a hole blocking layer, etc.) arranged therebetween.

[0004] In the prior art, a deposition method is generally used to manufacture an organic light-emitting device. However, there are problems such as material loss often occurs when manufacturing an organic light-emitting device by a deposition method, and it is difficult to manufacture a device with a large area, and in order to solve these problems, a device using a solution method is developed.

[0005] Therefore, there is a need to develop materials for solution methods. Summary of the invention

[0006] Technical issues

[0007] The present invention relates to an ink composition, an organic material layer containing the same, and an organic light-emitting device containing the same.

[0008] Technical Solution

[0009] An exemplary embodiment of the present invention provides an ink composition including a compound represented by the following Chemical Formula 1 and a first solvent represented by the following Chemical Formula A.

[0010] [Chemical formula 1]

[0011]

[0012] [Chemical formula A]

[0013]

[0014] In Chemical Formula 1 and Chemical Formula A,

[0015] Y1 to Y10 are the same as or different from each other and are each independently hydrogen; deuterium; hydroxyl; ether; carbonyl; ester; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted cycloalkenyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryl; or substituted or unsubstituted amino,

[0016] Lc is a substituted or unsubstituted heteroarylene group containing O, S or Si,

[0017] L1 and L2 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group,

[0018] L11 and L12 are the same as or different from each other and are each independently a direct bond; -O-; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group,

[0019] Ar1 to Ar4 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0020] R1 and R2 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group,

[0021] X1 and X2 are the same or different from each other and are each independently a curable group,

[0022] r1 and r2 are each an integer from 0 to 7, and when r1 and r2 are each 2 or more, the two or more substituents in the brackets are the same as or different from each other,

[0023] l11 and l12 are each an integer of 1 to 3, and when l11 and l12 are each 2 or more, two or more substituents in the brackets are the same as or different from each other,

[0024] f1 is 0 to the maximum number of substituents that can be bonded to Ar1,

[0025] f2 is 0 to the maximum number of bonds that the substituent can bond to Ar2,

[0026] f3 is 0 to the maximum bondable number of substituents that can be bonded to Ar3, and

[0027] f4 is 0 to the maximum possible number of bonds that a substituent can bond to Ar4.

[0028] Another exemplary embodiment of the present invention provides a pixel including the above-mentioned ink composition or a cured product thereof.

[0029] Yet another exemplary embodiment of the present invention provides an organic material layer including the above-mentioned pixel.

[0030] Another exemplary embodiment of the present invention provides an organic light-emitting device, which includes: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer are the above-mentioned organic material layer.

[0031] Beneficial Effects

[0032] When a plurality of pixels are coated with the ink composition according to an exemplary embodiment of the present invention, there is an effect that the thickness between pixels is uniformly coated.

[0033] Furthermore, the ink composition according to an exemplary embodiment of the present invention has an advantage of forming a stable thin film that is not damaged by a subsequent solution process by forming a thin film formed through a heat treatment or a light treatment.

[0034] Furthermore, since the ink composition according to an exemplary embodiment of the present invention exhibits resistance to a specific solvent after being cured, a solution process can be performed when manufacturing a device, and thus, the device can be manufactured to have a large area.

[0035] In addition, the ink composition according to an exemplary embodiment of the present invention can be used as a material for an organic material layer of an organic light-emitting device, and when the ink composition is applied to an organic light-emitting device, a device having a low driving voltage, excellent efficiency characteristics and / or excellent service life characteristics can be obtained. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] Figure 1 An organic light emitting device according to an exemplary embodiment of the present invention is shown.

[0037] Figure 2 The results of NMR measurement of Compound DA are shown.

[0038] Figure 3 The NMR measurement results of Compound DB are shown.

[0039] Figure 4 A line bank inkjet substrate is shown to which an ink composition is applied.

[0040] Figure 5 Application of an ink composition to a line bank inkjet substrate is shown.

[0041] Figure 6 The ink composition is shown to be formed as a thin film on a line bank inkjet substrate.

[0042] Figure 7is a diagram showing a plan view of an organic material layer in which a line bank is formed.

[0043] Figure 8 is a diagram showing a plan view of an organic material layer in which separation banks are formed.

[0044] Fig. 9 is a diagram showing the thickness of a pixel according to Example 1-1.

[0045] Fig.10 is a graph showing the thickness of a pixel according to Comparative Example 1-1.

[0046] 1': Pixel

[0047] 101: Base

[0048] 201: First electrode

[0049] 301: Hole injection layer

[0050] 401: Hole transport layer

[0051] 501: Luminous layer

[0052] 601: Electron injection and transport layer

[0053] 701: Second electrode DETAILED DESCRIPTION

[0054] Hereinafter, the present invention will be described in detail.

[0055] An exemplary embodiment of the present invention provides an ink composition including a compound represented by the following Chemical Formula 1 and a first solvent represented by the following Chemical Formula A.

[0056] [Chemical formula 1]

[0057]

[0058] [Chemical formula A]

[0059]

[0060] In Chemical Formula 1 and Chemical Formula A,

[0061] Y1 to Y10 are the same as or different from each other and are each independently hydrogen; deuterium; hydroxyl; ether; carbonyl; ester; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted cycloalkenyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryl; or substituted or unsubstituted amino,

[0062] Lc is a substituted or unsubstituted heteroarylene group containing O, S or Si,

[0063] L1 and L2 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group,

[0064] L11 and L12 are the same as or different from each other and are each independently a direct bond; -O-; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group,

[0065] Ar1 to Ar4 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0066] R1 and R2 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group,

[0067] X1 and X2 are the same or different from each other and are each independently a curable group,

[0068] r1 and r2 are each an integer from 0 to 7, and when r1 and r2 are each 2 or more, the two or more substituents in the brackets are the same as or different from each other,

[0069] l11 and l12 are each an integer of 1 to 3, and when l11 and l12 are each 2 or more, two or more substituents in the brackets are the same as or different from each other,

[0070] f1 is 0 to the maximum number of substituents that can be bonded to Ar1,

[0071] f2 is 0 to the maximum number of bonds that the substituent can bond to Ar2,

[0072] f3 is 0 to the maximum bondable number of substituents that can be bonded to Ar3, and

[0073] f4 is 0 to the maximum possible number of bonds that a substituent can bond to Ar4.

[0074] The compound of Chemical Formula 1 according to an exemplary embodiment of the present invention has a high highest occupied molecular orbital (HOMO) energy level value and excellent hole mobility by including both a sub-heteroaryl group (Lc) containing O, S or Si and two fluorene derivatives. In addition, a curable group is introduced into the two fluorene derivatives to suppress the formation of free radicals at the corresponding positions, thereby enhancing the stability of the compound. For this reason, the case where the compound of Chemical Formula 1 is applied to the organic material layer in the organic light-emitting device shows an effect of improving the performance of the organic light-emitting device. In particular, when the compound of Chemical Formula 1 is applied to the hole injection layer, this promotes the transmission or injection of holes, thereby providing an organic light-emitting device having high luminous efficiency and long service life characteristics.

[0075] Since the solvent represented by Chemical Formula A according to an exemplary embodiment of the present invention contains biphenyl as a core structure, the solvent has excellent solubility for the solute (the compound represented by Chemical Formula 1) contained in the ink composition. In addition, there is an advantage that the uniformity of the organic material layer can be improved by reducing the thickness deviation between pixels due to a good leveling effect. Specifically, the ink composition can reduce the thickness deviation between pixels that have been applied and dried (or heat-treated). Therefore, by reducing the factors that affect the interference conditions of the light emitted from the light-emitting device according to the thickness, excellent light-emitting and / or color-developing effects can be expected.

[0076] In the present invention, when one member (layer) is disposed "on" another member (layer), this includes not only a case where one member (layer) is in contact with another member but also a case where another member (layer) exists between the two members (layers).

[0077] In the present invention, when a portion “includes” a constituent element, unless otherwise specifically described, this does not mean that other constituent elements are excluded but means that other constituent elements may further be included.

[0078] In the present invention, "layer" has the same meaning as "film" commonly used in the art, and means a coating covering a target area. The size of the "layer" is not limited, and the sizes of the various "layers" may be the same as or different from each other. In an exemplary embodiment, the size of the "layer" may be the same as the size of the entire device, may correspond to the size of a specific functional area, and may also be as small as a single sub-pixel.

[0079] Unless otherwise defined in the present invention, all technical and scientific terms used in the present invention have the same meaning as commonly understood by those of ordinary skill in the art to which the present invention belongs. Although methods and materials similar or equivalent to the methods and materials described in the present invention can be used in the practice or testing of exemplary embodiments of the present invention, suitable methods and materials will be described below. All publications, patent applications, patents and other references mentioned in the present invention are hereby incorporated by reference in their entirety, and in the event of a conflict, unless a specific paragraph is mentioned, the present invention (including definitions) shall prevail. In addition, materials, methods and examples are illustrative only and are not intended to be limiting. In the present invention, Each means a moiety bonded to another substituent or bonding moiety.

[0080] In the present invention, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed into another substituent, and the position of substitution is not limited as long as the position is a position where a hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0081] In the present invention, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, halogen groups, amine groups, alkyl groups, aryl groups, and heteroaryl groups, substituted with substituents in which two or more substituents among the exemplified substituents are linked, or having no substituent.

[0082] In the present invention, the fact that two or more substituents are linked means that the hydrogen of any substituent is linked to another substituent. For example, isopropyl and phenyl can be linked to each other to form a substituent.

[0083] In the present invention, there is no limitation on the bonding direction of -COO-. For example, "-COO-" means both.

[0084] In the present invention, the halogen group is a fluoro group (—F), a chloro group (—Cl), a bromo group (—Br) or an iodo group (—I).

[0085] In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30, 1 to 20, 1 to 10, or 1 to 5. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0086] In the present invention, an alkylene group means a group having two bonding positions in an alkyl group, that is, a divalent group. The above description of the alkyl group can be applied to the alkylene group, except that the alkylene group is divalent.

[0087] In the present invention, the number of carbon atoms of the cycloalkyl group is not particularly limited, but is preferably 3 to 60. In an exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. Specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

[0088] In the present invention, aryl means a monovalent aromatic hydrocarbon or a monovalent group of an aromatic hydrocarbon derivative. In the present invention, aromatic hydrocarbon means a compound in which π electrons are completely conjugated and contain a planar ring, and aromatic hydrocarbon derivatives mean a structure in which aromatic hydrocarbons or cyclic aliphatic hydrocarbons are fused with aromatic hydrocarbons. In addition, in the present invention, aryl is intended to include a monovalent group in which two or more aromatic hydrocarbons or aromatic hydrocarbon derivatives are connected to each other. Aryl is not particularly limited, but preferably has 6 to 60 carbon atoms, 6 to 50 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 20 carbon atoms, 6 to 18 carbon atoms, 6 to 15 carbon atoms, 6 to 13 carbon atoms or 6 to 12 carbon atoms, and can be a monocyclic aromatic group or a polycyclic aromatic group.

[0089] The monocyclic aromatic group is not particularly limited, but preferably has 6 to 60 carbon atoms, 6 to 54 carbon atoms, 6 to 48 carbon atoms, 6 to 42 carbon atoms, 6 to 36 carbon atoms, 6 to 30 carbon atoms, 6 to 24 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms, and may specifically be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

[0090] The polycyclic aromatic 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 22 carbon atoms, 6 to 20 carbon atoms, 6 to 18 carbon atoms, 6 to 16 carbon atoms, 6 to 15 carbon atoms, 6 to 14 carbon atoms, 6 to 13 carbon atoms, 6 to 12 carbon atoms, or 6 to 10 carbon atoms, and may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, triphenylene, fluorenyl, etc., but are not limited thereto.

[0091] In the present invention, an arylene group means an aryl group having two bonding sites, that is, a divalent group. The above description of the aryl group can be applied to the arylene group, except that the arylene group is a divalent group.

[0092] In the present invention, the heterocyclic group is an aromatic group, an aliphatic group, or a condensed ring group of an aromatic group and an aliphatic group containing one or more of N, O, P, S, Si and Se as a heteroatom. The number of carbon atoms in the heterocyclic group is not particularly limited, but can be 2 to 60.

[0093] In the present invention, heteroaryl means a monovalent aromatic heterocycle. Here, the aromatic heterocycle is a monovalent group of an aromatic ring or a derivative of an aromatic ring, and means a group containing one or more selected from N, O, P, S, Si and Se as a heteroatom. Derivatives of aromatic rings include all structures in which an aromatic ring or an aliphatic ring is fused with an aromatic ring. In addition, in this specification, heteroaryl is intended to include a monovalent group in which two or more aromatic rings containing heteroatoms or two or more derivatives of aromatic rings containing heteroatoms are connected to each other. The number of carbon atoms of the heteroaryl is preferably 2 to 60, 2 to 50, 2 to 30, 2 to 20, 2 to 18, or 2 to 13. Examples of heteroaryl include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, pyridinyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthrolinyl, dibenzofuranyl and the like, but are not limited thereto.

[0094] In the present invention, the heteroarylene group means a group having two bonding positions in a heteroaryl group, that is, a divalent group. The above description of the heteroaryl group can be applied to the heteroarylene group, except that the heteroarylene group is divalent.

[0095] In the present invention, the above description of the aryl group can be applied to the aromatic ring.

[0096] In the present invention, the aliphatic ring is not aromatic but is a hydrocarbon ring, and examples thereof include the above-mentioned examples of the cycloalkyl group, adamantyl group and the like.

[0097] In the present invention, the curable group can undergo polymerization or crosslinking reaction, and through this, a reaction to increase the molecular weight can be performed, and examples of the curable group include a thermosetting group that is cured by heat, a photocurable group that is cured by light, and the like.

[0098] In an exemplary embodiment of the present invention, the curable group is any one of the following structures.

[0099]

[0100] In the structure,

[0101] R32 and R34 are the same as or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group,

[0102] L31 to L38 are the same as or different from each other and are each independently a direct bond; -O-; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group,

[0103] l34 to l38 are each an integer of 1 to 10, and when l34 to l38 are each 2 or more, two or more substituents in the brackets are the same as or different from each other, and

[0104] is a portion bonded to Chemical Formula 1.

[0105] Hereinafter, the compound represented by Chemical Formula 1 will be described in detail.

[0106] The ink composition of the present invention includes a compound represented by Chemical Formula 1.

[0107] In an exemplary embodiment of the present invention, Chemical Formula 1 is represented by the following Chemical Formula 1-A.

[0108] [Chemical Formula 1-A]

[0109]

[0110] In Chemical Formula 1-A,

[0111] Definitions of Lc, L1, L2, L11, L12, Ar1 to Ar4, R1, R2, X1, X2, r1, r2, l11, l12 and f1 to f4 are the same as those in Chemical Formula 1.

[0112] In an exemplary embodiment of the present invention, Chemical Formula 1 is represented by the following Chemical Formula 1-1.

[0113] [Chemical formula 1-1]

[0114]

[0115] In Chemical Formula 1-1,

[0116] Cy1 and Cy2 are the same as or different from each other and are each independently a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms,

[0117] Y is O, S or SiRy1Ry2,

[0118] Ry1 and Ry2 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl, and

[0119] L1, L2, L11, L12, Ar1 to Ar4, R1, R2, X1, X2, r1, r2, l11, l12 and f1 to f4 are the same as those defined in Chemical Formula 1.

[0120] In an exemplary embodiment of the present invention, Cy1 and Cy2 are the same as or different from each other, and are each independently a substituted or unsubstituted aromatic ring having 6 to 18 carbon atoms.

[0121] In an exemplary embodiment of the present invention, Cy1 and Cy2 are the same as or different from each other, and are each independently a substituted or unsubstituted aromatic ring having 6 to 10 carbon atoms.

[0122] In an exemplary embodiment of the present invention, Cy1 and Cy2 are the same as or different from each other, and are each independently a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring.

[0123] In an exemplary embodiment of the present invention, Cy1 and Cy2 are the same as or different from each other, and are each independently a benzene ring; or a naphthalene ring.

[0124] In an exemplary embodiment of the present invention, Lc is a substituted or unsubstituted tricyclic to decacyclic heteroarylene group containing O, S or Si.

[0125] In an exemplary embodiment of the present invention, Lc is a substituted or unsubstituted tricyclic to octacyclic heteroarylene group containing O, S or Si.

[0126] In an exemplary embodiment of the present invention, Lc is a substituted or unsubstituted tricyclic to hexacyclic heteroarylene group containing O, S or Si.

[0127] In an exemplary embodiment of the present invention, Lc is a substituted or unsubstituted divalent dibenzofuranyl group; a substituted or unsubstituted divalent naphthobenzofuranyl group; a substituted or unsubstituted divalent dinaphthofuranyl group; a substituted or unsubstituted divalent dibenzothiophenyl group; a substituted or unsubstituted divalent naphthobenzothiophenyl group; a substituted or unsubstituted divalent dinaphthothiophenyl group; or a substituted or unsubstituted divalent dibenzosilyl group.

[0128] In an exemplary embodiment of the present invention, Lc is a divalent dibenzofuranyl group which is unsubstituted or substituted with a halogen group, an alkyl group or an aryl group; a divalent naphthobenzofuranyl group which is unsubstituted or substituted with a halogen group, an alkyl group or an aryl group; a divalent dinaphthofuranyl group which is unsubstituted or substituted with a halogen group, an alkyl group or an aryl group; a divalent dibenzothiophenyl group which is unsubstituted or substituted with a halogen group, an alkyl group or an aryl group; a divalent naphthobenzothiophenyl group which is unsubstituted or substituted with a halogen group, an alkyl group or an aryl group; a divalent dinaphthothiophenyl group which is unsubstituted or substituted with a halogen group, an alkyl group or an aryl group; or a divalent dibenzosilyl group which is unsubstituted or substituted with a halogen group, an alkyl group or an aryl group.

[0129] In an exemplary embodiment of the present invention, Lc is a divalent dibenzofuranyl group; a divalent naphthobenzofuranyl group; a divalent dinaphthofuranyl group; a divalent dibenzothiophenyl group; a divalent naphthobenzothiophenyl group; a divalent dinaphthothiophenyl group; or a divalent dibenzosilyl group which is unsubstituted or substituted with an alkyl group or an aryl group.

[0130] In an exemplary embodiment of the present invention, Lc is any one of the following structures, and the following structures are unsubstituted or substituted with another substituent.

[0131]

[0132] In the structure described,

[0133] Ry1 and Ry2 are the same as or different from each other and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and

[0134] is a portion connected to Chemical Formula 1.

[0135] In an exemplary embodiment of the present invention, the additional substituents substituting the structure are one or more selected from the group consisting of: deuterium; a halogen group; an alkyl group; an alkoxy group; an aryl group; and a heterocyclic group.

[0136] In an exemplary embodiment of the invention, the structure is unsubstituted or substituted with deuterium, a halogen group, an alkyl group, an alkoxy group, an aryl group, or a heterocyclic group.

[0137] In an exemplary embodiment of the present invention, Lc is any one of the structures, and the structure is unsubstituted.

[0138] In an exemplary embodiment of the present invention, Ry1 and Ry2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0139] In an exemplary embodiment of the present invention, Ry1 and Ry2 are the same as or different from each other, and are each independently an alkyl group; or an aryl group.

[0140] In an exemplary embodiment of the present invention, Ry1 and Ry2 are the same as or different from each other, and are each independently an alkyl group having 1 to 30 carbon atoms; or an aryl group having 6 to 30 carbon atoms.

[0141] In an exemplary embodiment of the present invention, Ry1 and Ry2 are the same as or different from each other, and are each independently a methyl group; an ethyl group; a butyl group; or a phenyl group.

[0142] In an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0143] In an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; or an alkyl group having 1 to 30 carbon atoms.

[0144] In an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0145] In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0146] In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0147] In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0148] In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or an unsubstituted or alkyl-substituted arylene group.

[0149] In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted phenylene group.

[0150] In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or an unsubstituted or alkyl-substituted phenylene group.

[0151] In an exemplary embodiment of the present invention, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or a phenylene group which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

[0152] In an exemplary embodiment of the present invention, L1 and L2 are each a direct bond.

[0153] In an exemplary embodiment of the present invention, L11 and L12 are the same as or different from each other, and are each independently a direct bond; -O-; a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0154] In an exemplary embodiment of the present invention, L11 and L12 are the same as or different from each other, and are each independently a direct bond; -O-; a methylene group; an ethylene group; a propylene group; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0155] In an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0156] In an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0157] In an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and are each independently an unsubstituted or alkyl- or heteroaryl-substituted aryl group having 6 to 30 carbon atoms; or an unsubstituted or alkyl-substituted heteroaryl group having 2 to 30 carbon atoms.

[0158] In an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group.

[0159] In an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group.

[0160] In an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and are each independently an unsubstituted or alkyl- or heteroaryl-substituted phenyl group; an unsubstituted or alkyl- or heteroaryl-substituted biphenyl group; an unsubstituted or alkyl-substituted dibenzofuranyl group; or an unsubstituted or alkyl-substituted dibenzothienyl group.

[0161] In an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and are each independently an unsubstituted or alkyl-substituted phenyl group; an unsubstituted or alkyl-substituted biphenyl group; an unsubstituted or alkyl-substituted dibenzofuranyl group; or an unsubstituted or alkyl-substituted dibenzothienyl group.

[0162] In an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other and are each independently a group to which any one or two or more of the following structures are linked, and the following structures are unsubstituted or substituted with another substituent.

[0163]

[0164] In the structure,

[0165] Z2 to Z14 are the same as or different from each other and are each independently S; O; CRjRk; SiRlRm; or NRn,

[0166] Rj to Rn are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclyl,

[0167] a3 and a4 are each an integer of 1 to 5, and when a3 and a4 are each 2 or more, two or more substituents in the brackets are the same as or different from each other, and

[0168] is a portion bonded to Chemical Formula 1.

[0169] In an exemplary embodiment of the present invention, the additional substituents substituting the structure are one or more selected from the group consisting of: deuterium; a halogen group; an alkyl group; an alkoxy group; an aryl group; and a heterocyclic group.

[0170] In an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other and are each independently a group to which any one or two or more of the following structures are linked, and the following structures are unsubstituted or substituted with another substituent.

[0171]

[0172] In the structure,

[0173] Z2, Z5 to Z7, Z10 to Z12, a3, a4, and Same as those described above.

[0174] In an exemplary embodiment of the present invention, the additional substituent is an alkyl group or a heteroaryl group.

[0175] In an exemplary embodiment of the present invention, Ar1 to Ar4 are any one of the following structures, and the following structure is unsubstituted or substituted with another substituent.

[0176]

[0177] In the structure, Z2 and Same as those described above.

[0178] In an exemplary embodiment of the present invention, the additional substituent is an alkyl group or a heteroaryl group.

[0179] In an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

[0180] In an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and are each independently an unsubstituted or alkyl-substituted aryl group.

[0181] In an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and are each independently an aryl group which is unsubstituted or substituted with an alkyl group having 1 to 30 carbon atoms.

[0182] In an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and are each independently an aryl group which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

[0183] In an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and are each independently an unsubstituted or alkyl-substituted phenyl group; an unsubstituted or alkyl-substituted biphenyl group; an unsubstituted or alkyl-substituted terphenyl group; or an unsubstituted or alkyl-substituted naphthyl group.

[0184] In an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other and are each independently any one of the following structures, and the following structures are unsubstituted or substituted with another substituent.

[0185]

[0186] In the structure, Same as described above.

[0187] In an exemplary embodiment of the present invention, the additional substituent is an alkyl group or a heteroaryl group.

[0188] In an exemplary embodiment of the present invention, the structure is unsubstituted or substituted with an alkyl group.

[0189] In an exemplary embodiment of the present invention, the structure is unsubstituted or substituted with at least one substituent selected from the group consisting of a methyl group, a dimethyl group, and a tert-butyl group.

[0190] In an exemplary embodiment of the present invention, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group which is unsubstituted or substituted with at least one substituent selected from a methyl group, a dimethyl group, and a tert-butyl group; a biphenyl group which is unsubstituted or substituted with at least one substituent selected from a methyl group, a dimethyl group, and a tert-butyl group; or a naphthyl group which is unsubstituted or substituted with at least one substituent selected from a methyl group, a dimethyl group, and a tert-butyl group.

[0191] In an exemplary embodiment of the present invention, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group; a phenyl group substituted with a methyl group; a phenyl group substituted with a dimethyl group; a phenyl group substituted with a tert-butyl group; or a biphenyl group.

[0192] In an exemplary embodiment of the present invention, Ar3 and Ar4 are the same as or different from each other and are each independently a phenyl group which is unsubstituted or substituted with at least one substituent selected from methyl, dimethyl and tert-butyl; a biphenyl group which is unsubstituted or substituted with at least one substituent selected from methyl, dimethyl and tert-butyl; a terphenyl group which is unsubstituted or substituted with at least one substituent selected from methyl, dimethyl and tert-butyl; or a naphthyl group which is unsubstituted or substituted with at least one substituent selected from methyl, dimethyl and tert-butyl.

[0193] In an exemplary embodiment of the present invention, Ar3 and Ar4 are the same as or different from each other and are each independently phenyl; phenyl substituted with methyl; phenyl substituted with dimethyl; phenyl substituted with tert-butyl; biphenyl; biphenyl substituted with methyl; biphenyl substituted with dimethyl; biphenyl substituted with tert-butyl; biphenyl substituted with dimethyl and tert-butyl; or terphenyl.

[0194] In an exemplary embodiment of the present invention, f1 is 0 to the maximum number of bonds that the substituent can bond to Ar1, f2 is 0 to the maximum number of bonds that the substituent can bond to Ar2, f3 is 0 to the maximum number of bonds that the substituent can bond to Ar3, and f4 is 0 to the maximum number of bonds that the substituent can bond to Ar4. In this case, the maximum number of bonds that the substituent can bond to is the number of hydrogens bonded to Ar1 to Ar4. For example, when Ar1 is a phenyl group, f1 is an integer from 0 to 5, and when Ar1 is a biphenyl group, f1 is an integer from 0 to 9.

[0195] In an exemplary embodiment of the present invention, f1 to f4 are each an integer of 0 to 11.

[0196] In an exemplary embodiment of the present invention, f1 to f4 are integers of 0 to 9, respectively.

[0197] In an exemplary embodiment of the present invention, f1 to f4 are integers of 0 to 7, respectively.

[0198] In an exemplary embodiment of the present invention, f1 is an integer from 0 to 5. In another exemplary embodiment of the present invention, f1 is an integer from 0 to 3.

[0199] In an exemplary embodiment of the present invention, f2 is an integer from 0 to 5. In another exemplary embodiment of the present invention, f2 is an integer from 0 to 5.

[0200] In an exemplary embodiment of the present invention, f3 is an integer from 0 to 5. In another exemplary embodiment of the present invention, f3 is an integer from 0 to 3.

[0201] In an exemplary embodiment of the present invention, f4 is an integer from 0 to 5. In another exemplary embodiment of the present invention, f4 is an integer from 0 to 3.

[0202] In an exemplary embodiment of the present invention, f1+f2+f3+f4 is an integer of 1 or more. Specifically, f1+f2+f3+f4 is an integer of 1 to 36. More specifically, f1+f2+f3+f4 is an integer of 1 to 20. That is, one or more of f1 to f4 is 1 or more. That is, the compound represented by Chemical Formula 1 includes one or more F.

[0203] In an exemplary embodiment of the present invention, -Ar1-(F) f1 、-Ar2-(F) f2、 -Ar3-(F) f3 and -Ar4-(F) f4 Each may be represented by any of the following structures, and the following structures are unsubstituted or substituted with another substituent.

[0204]

[0205] In the structure described,

[0206] Z2 is S; O; CRjRk; SiRlRm; or NRn,

[0207] Rj to Rn are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclyl,

[0208] ma, mb and md are integers from 0 to 5, mc, me, mf and mj are integers from 0 to 4, and mg, mh and mi are integers from 0 to 7, and

[0209] is a portion bonded to Chemical Formula 1.

[0210] In an exemplary embodiment of the present invention, Z2 is O or S.

[0211] In an exemplary embodiment of the present invention, -Ar1-(F) f1 、-Ar2-(F) f2、 -Ar3-(F) f3 and -Ar4-(F) f4 is any one of the following structures, and the following structures are unsubstituted or substituted with another substituent.

[0212]

[0213] In the structure described,

[0214] ma to mg and Same as those described above.

[0215] In an exemplary embodiment of the present invention, the additional substituents substituting the structure are one or more substituents selected from the group consisting of: deuterium; a halogen group; an alkyl group; an alkoxy group; an aryl group; and a heteroaryl group.

[0216] In an exemplary embodiment of the invention, the structure is unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; an alkyl group having 1 to 30 carbon atoms; an alkoxy group having 1 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms; and a heteroaryl group having 2 to 30 carbon atoms.

[0217] In an exemplary embodiment of the present invention, the structure is unsubstituted or substituted with an alkyl group.

[0218] In an exemplary embodiment of the present invention, the structure is unsubstituted or substituted with one or more substituents selected from the group consisting of methyl, dimethyl, and tert-butyl.

[0219] In an exemplary embodiment of the present invention, X1 and X2 are the same as or different from each other, and are each independently selected from the above-mentioned curable group structures.

[0220] In an exemplary embodiment of the present invention, X1 and X2 are the same as or different from each other, and are each independently any one of the following structures.

[0221]

[0222] In the structure described,

[0223] L32 and L34 to L38 are a direct bond; -O-; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group,

[0224] l34 to l38 are each an integer of 1 to 10, and when l34 to l38 are each 2 or more, two or more substituents in the brackets are the same as or different from each other, and

[0225] is a portion bonded to Chemical Formula 1.

[0226] In an exemplary embodiment of the present invention, X1 and X2 are the same as or different from each other, and are each independently any one of the following structures.

[0227]

[0228] In an exemplary embodiment of the present invention, the compound represented by Chemical Formula 1 is any one of the following structures.

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249] Hereinafter, the first solvent represented by Chemical Formula A will be described in detail.

[0250] According to an exemplary embodiment of the present invention, Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; deuterium; hydroxyl; ether; carbonyl; ester; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted cycloalkenyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryl; or substituted or unsubstituted amine.

[0251] According to an exemplary embodiment of the present invention, Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; deuterium; hydroxyl; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted cycloalkenyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryl; or substituted or unsubstituted amine.

[0252] According to an exemplary embodiment of the present invention, Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

[0253] According to an exemplary embodiment of the present invention, Y1 to Y10 are the same as or different from each other, and are each independently 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.

[0254] According to an exemplary embodiment of the present invention, Y1 to Y10 are the same as or different from each other, and are each independently 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.

[0255] According to an exemplary embodiment of the present invention, Y1 to Y10 are the same as or different from each other, and are each independently 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.

[0256] According to an exemplary embodiment of the present invention, Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; deuterium; an alkyl group; or an alkoxy group.

[0257] According to an exemplary embodiment of the present invention, Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; deuterium; substituted or unsubstituted methyl; substituted or unsubstituted ethyl; substituted or unsubstituted propyl; substituted or unsubstituted butyl; substituted or unsubstituted pentyl; substituted or unsubstituted hexyl; substituted or unsubstituted isopropyl; substituted or unsubstituted isobutyl; substituted or unsubstituted tert-butyl; substituted or unsubstituted methoxy; substituted or unsubstituted ethoxy; substituted or unsubstituted propoxy; or substituted or unsubstituted butoxy.

[0258] According to an exemplary embodiment of the present invention, Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; deuterium; methyl; ethyl; propyl; butyl; pentyl; hexyl; isopropyl; isobutyl; tert-butyl; methoxy; ethoxy; propoxy; or butoxy.

[0259] According to an exemplary embodiment of the present invention, Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; deuterium; ethyl; propyl; butyl; pentyl; isopropyl; or methoxy.

[0260] In an exemplary embodiment of the present invention, the first solvent represented by Chemical Formula A is any one of the following structures.

[0261]

[0262] In the structure, Y1 to Y10 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

[0263] In an exemplary embodiment of the present invention, the first solvent represented by Chemical Formula A is any one or a mixed solution of two or more selected from the following compounds.

[0264]

[0265] In an exemplary embodiment of the present invention, the first solvent represented by Chemical Formula A is any one of the above structures.

[0266] In an exemplary embodiment of the present invention, the surface tension of the first solvent represented by Chemical Formula A is 32 to 38 mN / m, and specifically, 33 to 37 mN / m, or 33.5 to 36.5 mN / m.

[0267] Since the surface tension of the first solvent represented by Chemical Formula A according to an exemplary embodiment of the present invention satisfies the above range, the range of the surface tension between materials other than the first solvent represented by Chemical Formula A can be easily adjusted. Specifically, the materials (e.g., additional solvents, other organic solvents, etc.) contained in the ink composition for the solution method generally need to be composed of materials that make the surface tension of the ink composition in the range of 25mN / m to 45mN / m, and in addition, it is preferred that the surface tension difference between the materials is small. The surface tension in the range of 32mN / m to 38mN / m is close to the median of the preferred surface tension range, and therefore, when the surface tension of the first solvent represented by Chemical Formula A is in the range of 32mN / m to 38mN / m, the surface tension difference between materials other than the first solvent represented by Chemical Formula A can be adjusted to be small. When the surface tension difference between materials other than the first solvent represented by Chemical Formula A is small, the organic light-emitting device manufactured by the solution method has the advantages that the flatness of the organic material layer and the thickness uniformity of the pixel are excellent.

[0268] In an exemplary embodiment of the present invention, the first solvent represented by Chemical Formula A has a boiling point of 250°C to 350°C, 270°C to 350°C, or 280°C to 330°C.

[0269] Since the first solvent represented by the chemical formula A having a boiling point within the above range is included, it can be expected that when the organic material layer of the organic light-emitting device is manufactured by a solution method, the flatness of the organic material layer and / or the thickness uniformity of the pixels are excellent. Specifically, since the first solvent represented by the chemical formula A has the lowest vapor pressure among the constituent solvents and is therefore not removed in the initial drying step, there is an advantage that the surface tension difference between the remaining materials can be adjusted even after the initial drying step. Therefore, there is an advantage that the flatness of the organic material layer of the organic light-emitting device and / or the thickness uniformity of the pixels are excellent.

[0270] In an exemplary embodiment of the present invention, the ink composition further includes a second solvent, and the second solvent includes one or more of a solvent represented by any one of the following Chemical Formulas B to D, methoxytoluene, and tetralin.

[0271] [Chemical formula B]

[0272]

[0273] [Chemical formula C]

[0274]

[0275] [Chemical formula D]

[0276]

[0277] In Chemical Formulae B to D,

[0278] L50 is a direct bond; or an alkylene group,

[0279] L51 and L53 to L55 are the same as or different from each other, and are each independently a direct bond; -O-; or a substituted or unsubstituted alkylene group,

[0280] L52 is -COO-,

[0281] R50, R51 and R54 to R56 are the same as or different from each other and are each independently a substituted or unsubstituted alkyl group,

[0282] R53 is hydrogen; deuterium; alkoxy; or substituted or unsubstituted alkyl,

[0283] a1 is 0 or 1,

[0284] r53 is an integer of 1 to 5, and when r53 is 2 or more, two or more R53 are the same as or different from each other, and

[0285] l50, l51, and l53 to l55 are each an integer of 1 to 10, and when l50, l51, and l53 to l55 are each 2 or more, two or more structures in the brackets are the same as or different from each other.

[0286] In an exemplary embodiment of the present invention, L50 is a direct bond; or an alkylene group having 1 to 10 carbon atoms.

[0287] In an exemplary embodiment of the present invention, L50 is a direct bond; or an alkylene group having 1 to 6 carbon atoms.

[0288] In an exemplary embodiment of the present invention, L50 is a direct bond; a methylene group; an ethylene group; a propylene group; or a butylene group.

[0289] In an exemplary embodiment of the present invention, l50 is an integer from 1 to 5.

[0290] In an exemplary embodiment of the present invention, L51 and L53 to L55 are the same as or different from each other, and are each independently a direct bond; -O-; or an alkylene group having 1 to 10 carbon atoms.

[0291] In an exemplary embodiment of the present invention, L51 and L53 are the same as or different from each other, and are each independently a direct bond; -O-; or an alkylene group having 1 to 10 carbon atoms.

[0292] In an exemplary embodiment of the present invention, L51 and L53 are the same as or different from each other, and are each independently a direct bond; -O-; or an alkylene group having 1 to 5 carbon atoms.

[0293] In an exemplary embodiment of the present invention, L51 and L53 are the same as or different from each other, and are each independently a direct bond; -O-; a methylene group; an ethylene group; or a propylene group.

[0294] In an exemplary embodiment of the present invention, l51 and l53 are each an integer of 1 to 5.

[0295] In an exemplary embodiment of the present invention, L54 and L55 are the same as or different from each other, and are each independently -O-; or an alkylene group.

[0296] In an exemplary embodiment of the present invention, L54 and L55 are the same as or different from each other, and are each independently -O-; or a linear or branched alkylene group.

[0297] In an exemplary embodiment of the present invention, l54 and l55 are each an integer from 1 to 10.

[0298] In an exemplary embodiment of the present invention, a1 is 0.

[0299] In an exemplary embodiment of the present invention, a1 is 1.

[0300] In an exemplary embodiment of the present invention, R50, R51, and R54 to R56 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0301] In an exemplary embodiment of the present invention, R50, R51, and R54 to R56 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0302] In an exemplary embodiment of the present invention, R50 and R51 are the same as or different from each other, and are each independently an alkyl group having 1 to 10 carbon atoms.

[0303] In an exemplary embodiment of the present invention, R50 to R51 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 10 carbon atoms.

[0304] In an exemplary embodiment of the present invention, R50 and R51 are the same as or different from each other, and are each independently a linear alkyl group having 1 to 10 carbon atoms; or a branched alkyl group having 3 to 10 carbon atoms.

[0305] In an exemplary embodiment of the present invention, R53 is hydrogen; or an alkoxy group.

[0306] In an exemplary embodiment of the present invention, R53 is hydrogen; or an alkoxy group having 1 to 10 carbon atoms.

[0307] In an exemplary embodiment of the present invention, R54 is an alkyl group having 1 to 30 carbon atoms.

[0308] In an exemplary embodiment of the present invention, R54 is a linear or branched alkyl group having 1 to 30 carbon atoms.

[0309] In an exemplary 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.

[0310] In an exemplary 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.

[0311] In an exemplary embodiment of the present invention, R55 and R56 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0312] In an exemplary embodiment of the present invention, R55 and R56 are the same as or different from each other, and are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms.

[0313] In an exemplary embodiment of the present invention, R55 and R56 are the same as or different from each other, and are each independently an alkyl group which is unsubstituted or substituted with a hydroxyl group.

[0314] In an exemplary embodiment of the present invention, R55 and R56 are the same as or different from each other, and are each independently an unsubstituted or hydroxy-substituted alkyl group having 1 to 10 carbon atoms.

[0315] In an exemplary embodiment of the present invention, the second solvent includes one or both of the following: a solvent represented by any one of Chemical Formulas B to D, methoxytoluene, and tetralin.

[0316] In an exemplary embodiment of the present invention, the second solvent is one or more 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.

[0317] In an exemplary embodiment of the present invention, the ink composition includes a second solvent represented by any one of Chemical Formulas B to D, and further includes a third solvent different from the first solvent and the second solvent.

[0318] In an exemplary embodiment of the present invention, the third solvent is any one of the solvent represented by any one of Chemical Formulas B to D, methoxytoluene, and tetralin, and is different from the second solvent.

[0319] In an exemplary embodiment of the present invention, the second solvent has a boiling point of 180°C to 280°C.

[0320] In an exemplary embodiment of the present invention, 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., and the boiling point of the first solvent is higher than that of the second solvent. As described above, since the boiling point of the second solvent is lower than that of the first solvent, when the ink composition is dried, the second solvent evaporates first, and the proportion of the first solvent increases, and therefore, the solvent drying speed and the flatness of the ink can be adjusted.

[0321] In an exemplary embodiment of the present invention, when the first solvent and the second solvent are used simultaneously, the effects of shortening the drying time and improving the uniformity of the thin film are exhibited.

[0322] In an exemplary embodiment of the present invention, the first solvent and the second solvent are contained in an amount of 4% to 60% by weight and 40% to 96% by weight, respectively, based on the total solvent. Specifically, the first solvent and the second solvent are contained in an amount of 5% to 35% by weight and 65% to 95% by weight, respectively. The above-mentioned ink composition needs to remain liquid in the pixel after printing and before entering the vacuum chamber, and when the first solvent is contained in an amount of less than 4% by weight, there is a problem that a large amount or all of the ink composition is dried during the process of printing the ink composition. On the contrary, when the first solvent is contained in an amount exceeding 60% by weight in the ink composition, the solvent may remain in the film.

[0323] In an exemplary embodiment of the present invention, the entire solvent means the first solvent and the second solvent combined.

[0324] Hereinafter, the ionic compound containing the anionic group represented by Chemical Formula 2 will be described in detail.

[0325] In an exemplary embodiment of the present invention, the ink composition further includes an ionic compound including an anionic group represented by Chemical Formula 2 below.

[0326] [Chemical formula 2]

[0327]

[0328] In chemical formula 2,

[0329] At least one of R201 to R220 is F; cyano; or a substituted or unsubstituted fluoroalkyl group,

[0330] At least one of the other R201 to R220 is a curable group,

[0331] The remaining R201 to R220 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitro group; a cyano group; an amino group; -OR221; -SR222; -SO3R223; -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 amino group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0332] R221 to R228 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0333] According to an exemplary embodiment of the present invention, a curable group is introduced into the ionic compound containing an anionic group represented by Chemical Formula 2 (hereinafter referred to as anionic group compound). In contrast, when the curable group is not introduced, the ionic compound will not be cured, so that the characteristics of the device are reduced due to the migration of the ionic compound between electrodes or layers. At the same time, when the number of curable groups increases, the curing rate of the ionic compound or the composition containing it increases, and the film retention rate is improved.

[0334] In an exemplary embodiment of the present invention, the number of curable groups of the anionic group compound represented by Chemical Formula 2 is one.

[0335] In an exemplary embodiment of the present invention, the number of curable groups of the anionic group compound represented by Chemical Formula 2 is two.

[0336] In an exemplary embodiment of the present invention, the number of curable groups of the anionic group compound represented by Chemical Formula 2 is four.

[0337] In an exemplary embodiment of the present invention, the number of F, cyano, or substituted or unsubstituted fluoroalkyl groups in the anionic group compound represented by Chemical Formula 2 is 16 to 19.

[0338] In an exemplary embodiment of the present invention, the weight parts of F in the anion group compound is 15 parts by weight to 50 parts by weight based on 100 parts by weight of the anion group compound.

[0339] In an exemplary embodiment of the present invention, the weight parts of F in the anion group compound is 10 parts by weight to 45 parts by weight based on 100 parts by weight of the anion group compound.

[0340] In an exemplary embodiment of the present invention, the number of F in the anion group compound is 8 to 20 based on 100 parts by weight of the anion group compound.

[0341] As described above, when the ratio of F, cyano group or fluoroalkyl group in the molecule increases, the film retention rate during heat treatment is improved.

[0342] According to an exemplary embodiment of the present invention, the ionic compound can be used in the hole injection layer of the organic light-emitting device, and when used in the hole injection layer, it can be used as a dopant. In this case, when the content of F in the ionic compound increases, the force of attracting electrons from another compound (host compound) increases, and holes are more well generated in the host, so that the performance of the hole injection layer is improved.

[0343] In an exemplary embodiment of the present invention, the content of F may be analyzed using a COSAAQF-100 combustion furnace coupled to a Dionex ICS 2000 ion chromatograph, or may be determined by 19F NMR, which is a method generally used for F analysis.

[0344] In an exemplary embodiment of the present invention, at least one benzene ring among the benzene rings including R201 to R205, the benzene rings including R206 to R210, the benzene rings including R211 to R215, and the benzene rings including R216 to R220 in Chemical Formula 2 is selected from the following structural formulas.

[0345]

[0346] In an exemplary embodiment of the present invention, Chemical Formula 2 is any one of the following structures.

[0347]

[0348]

[0349] In the structure described,

[0350] n1 is an integer from 1 to 3, m1 is an integer from 1 to 3, and n1+m1=4,

[0351] n2 is an integer from 0 to 3, m2 is an integer from 1 to 4, and n2+m2=4,

[0352] M1 is deuterium; a halogen group; a nitro group; a cyano group; an amino group; -OR221; -SR222; -SO3R223; -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 amino group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0353] R221 to R228 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group, and

[0354] i is an integer of 1 to 4, and when i is 2 or more, two or more M1s are the same as or different from each other.

[0355] In an exemplary embodiment of the present invention, the ionic compound further includes a cationic group. Specifically, the above ink composition further includes an ionic compound including an anionic group and a cationic group represented by the above Chemical Formula 2.

[0356] In an exemplary embodiment of the present invention, the ionic compound further comprises a cationic group, and the cationic group is a monovalent cationic group, Compound or any of the following structures.

[0357]

[0358] In the structure described,

[0359] Q30 to Q105 are the same as or different from each other and are each independently hydrogen; deuterium; cyano; nitro; halogen group; hydroxyl group; -COOR250; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryloxy group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or a curable group,

[0360] R250 is hydrogen; deuterium; or substituted or unsubstituted alkyl,

[0361] x is an integer from 0 to 10, and

[0362] p1 is 1 or 2, q1 is 0 or 1, and p1+q1=2.

[0363] In an exemplary embodiment of the present invention, the monovalent cationic group may be an alkali metal cation, and examples of the alkali metal cation include Na + , Li + , K + etc., but not limited to.

[0364] In an exemplary embodiment of the present invention, the cationic group is Compound; or selected from any one of the above structural formulas.

[0365] In an exemplary embodiment of the present invention, the cationic group is any one of the following structures.

[0366]

[0367] In the structure described,

[0368] Q30 to Q34, Q30' to Q34', and Q62 to Q95 are the same as or different from each other, and are each hydrogen; deuterium; cyano; nitro; 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, and

[0369] R250 is hydrogen; deuterium; or substituted or unsubstituted alkyl.

[0370] In an exemplary embodiment of the present invention, the cationic group is any one of the following structures.

[0371]

[0372] In an exemplary embodiment of the present invention, the ionic compound is any one of the following Chemical Formulae D-1 to D-37.

[0373]

[0374]

[0375]

[0376]

[0377]

[0378] In an exemplary embodiment of the present invention, in the ionic compound, the anionic group and the cationic group represented by Chemical Formula 2 are included in an equivalent ratio of 1:5 to 5:1. Specifically, the anionic group and the cationic group represented by Chemical Formula 2 are included in an equivalent ratio of 1:1.

[0379] Hereinafter, the ink composition will be described in detail.

[0380] An exemplary embodiment of the present invention provides an ink composition including a compound represented by the above Chemical Formula 1 and a first solvent represented by the above Chemical Formula A.

[0381] According to an exemplary embodiment of the present invention, the ink composition further includes an ionic compound including an anionic group represented by Chemical Formula 2 above.

[0382] According to an exemplary embodiment of the present invention, the ionic compound further includes the above-mentioned cationic group. That is, the ink composition further includes an ionic compound including the anionic group represented by the above-mentioned Chemical Formula 2 and the above-mentioned cationic group.

[0383] An exemplary embodiment of the present invention provides an ink composition including: a compound represented by the above Chemical Formula 1 and a first solvent represented by the above Chemical Formula A, and further including: one or more of: the above anionic group compound; the above cationic group; and the above second solvent.

[0384] An exemplary embodiment of the present invention provides an ink composition including: a compound represented by the above Chemical Formula 1; a first solvent represented by the above Chemical Formula A; an ionic compound containing an anionic group represented by the above Chemical Formula 2 and the above cationic group; and the above second solvent.

[0385] According to an exemplary embodiment of the present invention, the compound represented by Chemical Formula 1 is included in an amount of 0.1 to 15 wt %, 0.1 to 10 wt %, or 0.1 to 5 wt %, based on 100 wt % of the ink composition.

[0386] According to an exemplary embodiment of the present invention, the first solvent represented by Chemical Formula A is included in an amount of 4 to 70 wt %, 4 to 50 wt %, or 4 to 35 wt % based on 100 wt % of the ink composition.

[0387] According to an exemplary embodiment of the present invention, the second solvent is included in an amount of 20 to 95 wt %, 40 to 95 wt %, or 65 to 95 wt %, based on 100 wt % of the ink composition.

[0388] According to an exemplary embodiment of the present invention, the ionic compound containing the anionic group represented by Chemical Formula 2 is included in an amount of 0.1 to 15 wt %, 0.1 to 10 wt %, or 0.1 to 5 wt % based on 100 wt % of the ink composition.

[0389] According to an exemplary embodiment of the present invention, based on 100 wt % of the ink composition, the compound represented by Chemical Formula 1, the first solvent represented by Chemical Formula A, the second solvent, and the ionic compound containing the anionic group represented by Chemical Formula 2 are included in amounts of 0.1 wt % to 15 wt %, 4 wt % to 50 wt %, 40 wt % to 95 wt %, and 0.1 wt % to 15 wt %, respectively.

[0390] According to an exemplary embodiment of the present invention, the compound represented by Chemical Formula 1, the first solvent represented by Chemical Formula A, the second solvent, and the ionic compound containing the anionic group represented by Chemical Formula 2 are included in amounts of 0.1 wt % to 15 wt %, 4 wt % to 35 wt %, 65 wt % to 95 wt %, and 0.1 wt % to 15 wt %, respectively, based on 100 wt % of the ink composition.

[0391] In an exemplary embodiment of the present invention, the viscosity of the ink composition at room temperature is 2 cP to 15 cP. When the above viscosity is satisfied, it is easy to manufacture a device. Specifically, when forming an organic material layer in an organic light-emitting device, a uniform film can be formed.

[0392] The above viscosity is a value measured at room temperature using a viscometer manufactured by Brookfield Engineering Labs Inc. after dissolving the object to be measured at any concentration of 1 wt % to 3 wt % in the first solvent or in a mixture in which the first solvent and the second solvent are mixed at an arbitrary ratio. 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.

[0393] According to an exemplary embodiment of the present invention, the ink composition is in a liquid phase. "Liquid phase" means that the composition is in a liquid state at room temperature under atmospheric pressure.

[0394] In an exemplary embodiment of the present specification, the ink composition may be cured by heat treatment or light treatment. When the ink composition is cured, this may be expressed as a cured product of the ink composition.

[0395] In an exemplary embodiment of the present invention, the ink composition further includes: a single molecule containing a photocurable group and / or a thermosetting group; or a single molecule containing an end group capable of forming a polymer by heat. As described above, the single molecule containing a photocurable group and / or a thermosetting group, or the single molecule containing an end group capable of forming a polymer by heat may be a compound having a molecular weight of 3,000 g / mol or less, but the molecular weight is not limited to the exemplified molecular weight.

[0396] A single molecule containing a photocurable group and / or a thermosetting group, or a single molecule containing an end group capable of forming a polymer by heat may mean an aromatic group such as phenyl, biphenyl, fluorene and naphthalene; an aromatic amine; or a single molecule in which fluorene is substituted with a photocurable group and / or a thermosetting group, or an end group capable of forming a polymer by heat.

[0397] In an exemplary embodiment of the present invention, the ink composition is a composition for forming one or more layers selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer.

[0398] Hereinafter, a pixel including the above-mentioned ink composition will be described in detail.

[0399] An exemplary embodiment of the present invention provides a pixel including the above-mentioned ink composition or a cured product thereof. The pixel may be included in an organic material layer, an organic light emitting diode, or an organic light emitting display device. The details of the organic material layer will be described below.

[0400] In an exemplary embodiment of the present invention, an organic light emitting display device includes a plurality of pixels consisting of a red (R) sub-pixel, a green (G) sub-pixel, and a blue (B) sub-pixel, and an organic light emitting diode and a pixel circuit are positioned for each sub-pixel. The organic light emitting diode includes two electrodes (an anode and a cathode) and an organic light emitting layer positioned therebetween, and the pixel circuit includes at least two thin film transistors and at least one capacitor.

[0401] In an exemplary embodiment of the present invention, an organic material layer, an organic light emitting diode, and / or an organic light emitting display device includes a bank that can be separated from each sub-pixel to apply ink, or a bank in which ink droplets are connected in two or more sub-pixels.

[0402] In an exemplary embodiment of the present invention, the form of the dam is not limited. As an example, the organic material layer, the organic light emitting diode or the organic light emitting display device may include a linear dam. The linear dam may define a linear pixel area and / or a sub-pixel area. As another example, the organic material layer, the organic light emitting diode or the organic light emitting display device may include a separation dam instead of a linear shape. Under normal circumstances, the light emitting layer in the organic material layer is composed of a red light emitting layer, a green light emitting layer and a blue light emitting layer respectively positioned in a red sub-pixel, a green sub-pixel and a blue sub-pixel. In this case, the above-mentioned pixel may correspond to a pixel or a sub-pixel. As a preferred exemplary embodiment, the pixel corresponds to a sub-pixel.

[0403] In an exemplary embodiment of the present invention, one or more pixels may be included in the above-mentioned organic material layer, organic light emitting diode or organic light emitting display device.

[0404] Hereinafter, an organic material layer including the above-mentioned pixel will be described in detail.

[0405] An exemplary embodiment of the present invention provides an organic material layer including the above-mentioned pixel. Since the pixel includes the above-mentioned ink composition or a cured product thereof, an exemplary embodiment of the present invention can be said to provide an organic material layer including the above-mentioned ink composition or a cured product thereof.

[0406] In an exemplary embodiment of the present invention, the organic material layer includes a plurality of the above-mentioned pixels. For example, the organic material 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 na and nb are each 2 to 10. 4 Integer from 10 to 10 3 Integer from 20 to 10 2 An integer.

[0407] In an exemplary embodiment of the present invention, na and nb are each 2 or more, 5 or more, 10 or more, or 20 or more, and 10 4 or less, 10 3 or less, or 10 2 or smaller.

[0408] In an exemplary embodiment of the present invention, the organic material layer comprises 2 or more, 4 or more, 10 or more, 20 or more, 40 or more, 80 or more, or 100 or more and 10 8 or less, 10 6 or less, or 10 4 pixels or less.

[0409] In an exemplary embodiment of the present invention, the pixels contained in the organic material layer are arranged in a line. Figure 4 and 7 As shown, a plurality of pixels 1' are arranged in rows to form a line.

[0410] In an exemplary embodiment of the present invention, the organic material layer comprises a plurality of lines in which a plurality of pixels are arranged in rows. Figure 4 and 7 As shown, a plurality of lines may be formed at regular intervals. For example, the y-axis on which the above-mentioned nb pixels are arranged is one line, and may include as many lines as the number of pixels (na) included in the x-axis.

[0411] In an exemplary embodiment of the present invention, the pixels included in the organic material layer are not arranged in a line form, but are arranged in a separated form. Figure 8 As shown, a plurality of pixels may be formed in a separate form.

[0412] In an exemplary embodiment of the present invention, the organic material layer includes na×nb pixels.

[0413] In an exemplary embodiment of the present invention, a plurality of pixels included in the organic material layer have a uniform thickness.

[0414] In an exemplary embodiment of the present invention, the organic material 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, wherein nc and nd are each 20 to 10 4 and satisfies the following formula 1.

[0415] [Formula 1]

[0416] IX(i′)-X(5)|≤5nm

[0417] In formula 1,

[0418] X(i') is the average thickness from the [(nd / 2)-4]th pixel to the [(nd / 2)+5]th pixel,

[0419] X(5) is the thickness of the 5th pixel from the edge, and

[0420] When nd is an odd number, (nd / 2) is a value obtained by rounding the first digit of the decimal.

[0421] For the case where nd is an odd number, for example, when 25 pixels are used for measurement (ie, when nd is 25), X(i') is the average thickness of the 13th to 18th pixels.

[0422] In an exemplary embodiment of the present invention, the [(nd / 2)-4]th pixel to the [(nd / 2)+5]th pixel mean pixels located at a central portion (center) of a plurality of pixels formed.

[0423] In an exemplary embodiment of the present invention, nd is 20 to 10 4 Integer from 20 to 10 3 or an integer from 20 to 100.

[0424] In an exemplary embodiment of the present invention, the thickness of the pixel may be measured by an optical thickness measuring device. As the optical thickness measuring device, an optical profiler manufactured by Bruker or the like may be used, but the optical thickness measuring device is not limited thereto.

[0425] In an exemplary embodiment of the present invention, satisfying Formula 1 means that the difference between the average thickness of a pixel positioned at the center of a plurality of pixels and the thickness of a pixel positioned at the fifth position from the edge is 5 nm or less. That is, it means that there is almost no difference in thickness between the center and edge portions of the pixel. Therefore, satisfying Formula 1 means that the thickness uniformity between pixels is improved.

[0426] In an exemplary embodiment of the present invention, the organic material layer satisfies Formula 2 below.

[0427] [Formula 2]

[0428] IX(i′)-X(4)|≤5nm

[0429] In formula 2,

[0430] X(i') is the same as defined in Formula 1, and

[0431] X(4) is the thickness of the 4th pixel from the edge.

[0432] In an exemplary embodiment of the present invention, the organic material layer satisfies Formula 3 below.

[0433] [Formula 3]

[0434] IX(i′)-X(3)I≤5nm

[0435] In formula 3,

[0436] X(i') is the same as defined in Formula 1, and

[0437] X(3) is the thickness of the third pixel from the edge.

[0438] In an exemplary embodiment of the present invention, in the organic material layer, a pixel satisfying the following Formula 11 exists in a second position from the edge.

[0439] [Formula 11]

[0440] IY(20)-Y(80)|≤5nm

[0441] In formula 11,

[0442] Y(20) is the height of the thin film in the portion corresponding to 20% of the pixel length, and Y(80) is the height of the thin film in the portion corresponding to 80% of the pixel length.

[0443] Satisfying Formula 11 means that in one pixel having a length Lx, the difference between the film height in a portion (0.2Lx) corresponding to 20% of the length and the film height in a portion (0.8Lx) corresponding to 80% of the length satisfies 5nm or less. That is, satisfying Formula 11 means that the film within the pixel is formed symmetrically without tilting to one side.

[0444] The fact that the pixel satisfying Formula 11 is in the second position from the edge means that among the formed pixels, the pixel on the edge side also maintains its shape and thickness. Therefore, it can be determined that the shape and thickness deviation of the pixel at the edge portion and the pixel at the center is formed into a small number.

[0445] In an exemplary embodiment of the present invention, a pixel included in an organic material layer is excellent in both thickness uniformity among a plurality of pixels and thickness uniformity within one pixel.

[0446] In an exemplary embodiment of the present invention, the length (Lx) of the pixel is 10 μm to 300 μm.

[0447] In the present invention, the edge means both ends on which the ink composition is printed. Figure 7 and Figure 8 In the example, when ink is printed in the direction from (a) to (b) (arrow direction), the (a) or (b) portion is indicated as an edge. Figure 7 The ink composition is shown to be applied in the longitudinal direction, but the direction in which the ink composition is applied is not limited thereto. For example, the ink may be applied in the transverse direction.

[0448] In an exemplary embodiment of the present invention, the organic material layer is included in an organic light emitting device.

[0449] In an exemplary embodiment of the present invention, the organic material layer is formed by a solution process.

[0450] In an exemplary embodiment of the present invention, the organic material layer is one or more layers selected from 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.

[0451] In an exemplary embodiment of the present invention, the organic material layer is one or more layers selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, and a light emitting layer.

[0452] In an exemplary embodiment of the present invention, the organic material layer is one or more layers selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer.

[0453] In a preferred exemplary embodiment of the present invention, the organic material layer is a hole injection layer, a hole transport layer or an electron blocking layer.

[0454] Hereinafter, an organic light emitting device will be described in detail.

[0455] An exemplary embodiment of the present invention provides an organic light-emitting device including: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer are the above-mentioned organic material layer.

[0456] That is, an exemplary embodiment of the present specification provides an organic light-emitting device, which includes: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain the above-mentioned ink composition or a cured product thereof.

[0457] In an exemplary embodiment of the present invention, the organic material layer includes one or more layers selected from 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 one or more layers selected from the hole injection layer, the hole transport layer, the hole injection and transport layer, the electron blocking layer, the light-emitting layer, the hole blocking layer, the electron injection layer, the electron transport layer, and the electron injection and transport layer contain the above-mentioned ink composition or a cured product thereof.

[0458] In an exemplary embodiment of the present invention, the organic material layer includes one or more layers selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer, and one or more layers selected from the hole injection layer, the hole transport layer, the hole injection and transport layer, and the electron blocking layer contain the above-mentioned ink composition or a cured product thereof.

[0459] In an exemplary embodiment of the present invention, the organic material 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 contains the above ink composition or a cured product thereof.

[0460] In an exemplary embodiment of the present invention, the organic material layer includes the above-mentioned na×nb pixels, and the na×nb pixels satisfy Formula 1.

[0461] Hereinafter, a method for manufacturing an organic light emitting device will be described in detail.

[0462] An exemplary embodiment of the present invention provides a method for manufacturing an organic light emitting device, the method comprising: preparing a first electrode;

[0463] forming an organic material layer having one or more layers on the first electrode; and

[0464] forming a second electrode on the organic material layer having one or more layers,

[0465] The forming of the organic material layer includes forming the organic material layer using the ink composition.

[0466] In an exemplary embodiment of the present invention, forming the organic material layer using the ink composition uses a spin coating method.

[0467] In an exemplary embodiment of the present invention, forming the organic material layer using the ink composition uses a printing method.

[0468] In an exemplary embodiment of the present invention, examples of the printing method include inkjet printing, nozzle printing, offset printing, transfer printing, screen printing, etc., but are not limited to the printing methods listed above.

[0469] In an exemplary embodiment of the present invention, forming the organic material layer using the ink composition uses an inkjet printing method.

[0470] In an exemplary embodiment of the present invention, forming one or more organic material layers using the ink composition may be performed by applying the ink composition on a substrate including a bank or an organic material layer, and then drying or heat-treating the ink composition.

[0471] As an example, the above ink composition is applied to a substrate including linear banks (linear bank inkjet substrate, Figure 4 )superior( Figure 5 ), and then a thin film in which the ink composition is dried and / or heat-treated may be formed ( Figure 6 ).

[0472] As another example, the ink composition may be applied to a substrate including banks that are not formed in a line form. In this case, the ink composition is applied to each bank.

[0473] The ink composition according to an exemplary embodiment of the present invention is suitable for a solution method due to its structural characteristics, so that an organic material layer can be formed by a printing method, and thus, has economical effects in terms of time and cost when manufacturing a device.

[0474] In an exemplary embodiment of the present invention, forming the organic material layer on the first electrode may further include drying after one or more decompression steps. As an example, forming the organic material layer having one or more layers on the first electrode may further include drying after two decompression steps. In this case, the drying after the first decompression is performed at a pressure of from normal pressure to 2×10 -2and at atmospheric pressure to 2×10 -2 The decompression time under the support can be 30 seconds to 600 seconds. In addition, the drying after the second decompression is 2×10 -2 Up to 2×10 -6 The support was carried out under 2×10 -2 Up to 2×10 -6 The decompression time under support may also be 30 seconds to 600 seconds.

[0475] In an exemplary embodiment of the present invention, forming the organic material layer using the ink composition includes: coating the ink composition; and heat-treating or light-treating the coated ink composition.

[0476] In an exemplary embodiment of the present invention, forming an organic material layer having one or more layers using an ink composition includes: coating a first electrode or an organic material layer having one or more layers with a coating composition; and heat-treating or light-treating the coated coating composition.

[0477] In an exemplary embodiment of the present invention, heat treatment of the coating composition may be performed by heat treatment, and the heat treatment temperature when heat treating the coating composition may be 85°C to 250°C, 100°C to 250°C in an exemplary embodiment, and 150°C to 250°C in another exemplary embodiment.

[0478] In an exemplary embodiment of the present invention, the heat treatment time in the heat treatment step may be 10 minutes to 2 hours, 10 minutes to 1 hour in an exemplary embodiment, and 20 minutes to 1 hour in another exemplary embodiment.

[0479] When forming the organic material layer using the ink composition includes heat-treating or light-treating the ink composition, the plurality of compounds contained in the ink composition may form crosslinks, thereby providing an organic material layer including a thin film structure. In this case, when another layer is stacked 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.

[0480] Therefore, when the organic material layer is formed by heat-treating or light-treating the ink composition, resistance to solvents is improved. Therefore, solution deposition and cross-linking methods can be repeated to form multiple layers, and stability can be improved to improve the life characteristics of the device.

[0481] Hereinafter, types of organic material layers included in the above-mentioned organic light emitting device will be described in detail.

[0482] In an exemplary embodiment of the present invention, the organic light emitting device includes an organic material layer having one layer, and one or more layers in the organic material layer include an 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.

[0483] In an exemplary embodiment of the present invention, an organic light-emitting device includes an organic material layer having two or more layers, and one or more layers of the organic material layer having two or more layers contain an ink composition or a cured product thereof. For example, in an organic material layer having two or more layers, an organic material layer having any one layer contains an ink composition or a cured product thereof, and further includes an additional organic material layer. The additional organic material layer according to an exemplary embodiment does not contain an ink composition or a cured product thereof. The additional organic material layer according to another exemplary embodiment also contains an ink composition or a cured product thereof. However, the organic light-emitting device is not limited to the example.

[0484] The organic material layer having two or more layers includes two or more layers selected from the group consisting of: for example, 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, an electron injection and transport layer, etc. In this case, the hole injection and transport layer means a layer that simultaneously injects and transports holes, and the electron injection and transport layer means a layer that simultaneously injects and transports electrons. However, the organic material layer forming the group is only an example and is not limited to the above examples. In addition, if necessary, the organic material layer having two or more layers may include two or more layers that play the same role. The organic light-emitting device according to an exemplary embodiment includes a first hole injection layer and a second hole injection layer. However, the organic material layer having two or more layers is not limited to these examples.

[0485] In an exemplary embodiment of the present invention, the organic material layer includes a light-emitting layer. As an example, the light-emitting layer includes an ink composition or a cured product thereof. As a specific example, the light-emitting layer includes an ink composition or a cured product thereof as a main body of the light-emitting layer. As another specific example, the light-emitting layer includes an ink composition or a cured product thereof as a dopant for the light-emitting layer.

[0486] In an exemplary embodiment of the present invention, the organic material layer includes a hole injection and transport layer, a hole injection layer, a hole transport layer, and an electron blocking layer. As an example, the hole injection and transport layer, the hole injection layer, the hole transport layer, or the electron blocking layer contains an ink composition or a cured product thereof.

[0487] In an exemplary embodiment of the present invention, the organic material layer is a hole injection layer, a hole transport layer and / or an electron blocking layer. As an example, the hole injection layer, the hole transport layer and / or the electron blocking layer comprises an ink composition or a cured product thereof.

[0488] In an exemplary embodiment of the present invention, the organic material layer further comprises one or more layers selected from a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer. As an example, one or more layers selected from a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer contain an ink composition or a cured product thereof. As another example, one or more layers selected from a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer do not contain an ink composition or a cured product thereof.

[0489] In an exemplary embodiment of the present invention, an organic light-emitting device includes: a first electrode; a second electrode; and an organic material layer having one or more layers arranged between the first electrode and the second electrode, wherein the organic material layer includes a light-emitting layer, a hole injection layer and an electron blocking layer, and the hole injection layer or the electron blocking layer contains an ink composition or a cured product thereof.

[0490] Hereinafter, a stack structure of an organic material layer and an organic light emitting device including the organic material layer will be described in detail.

[0491] In an exemplary embodiment of the present invention, the organic material layer of the organic light-emitting device has a single-layer structure. For example, the organic material layer having a single-layer structure is disposed between the first electrode and the second electrode of the organic light-emitting device, and the organic material layer contains an ink composition or a cured product thereof. In a specific exemplary embodiment, the organic material layer having a single-layer structure is a light-emitting layer, and in this case, the light-emitting layer contains an ink composition or a cured product thereof.

[0492] In an exemplary embodiment of the present invention, the organic material layer of the organic light emitting device has a multilayer structure in which an organic material layer having two or more layers is stacked. For example, the organic material layer having the multilayer structure is disposed between the first electrode and the second electrode of the organic light emitting device.

[0493] In an exemplary embodiment of the present invention, the organic material layer having a multilayer structure includes a light-emitting layer and an organic material layer other than the light-emitting layer. As an example, the light-emitting layer is arranged between the first electrode and the second electrode, and the organic material layer other than the light-emitting layer is arranged between the first electrode and the light-emitting layer. As another example, the light-emitting layer is arranged between the first electrode and the second electrode, and the organic material layer other than the light-emitting layer is arranged between the light-emitting layer and the second electrode. As another example, the light-emitting layer is arranged between the first electrode and the second electrode, any organic material layer other than the light-emitting layer is arranged between the first electrode and the light-emitting layer, and any other organic material layer other than the light-emitting layer is arranged between the light-emitting layer and the second electrode. However, the above structure is only an example, and the structure is not limited to the above structure. In addition, the organic material layer other than the light-emitting layer can be one or more layers selected from the following: 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, an electron injection and transport layer, etc., but not limited thereto.

[0494] Typically, a hole injection layer, a hole transport layer or an electron blocking layer in an organic light-emitting device is disposed between the anode and the light-emitting layer. As a specific example, the hole injection layer is disposed on the anode, the hole transport layer is disposed on the hole injection layer, and the electron blocking layer is disposed on the hole injection layer, but the present invention is not limited to the above examples.

[0495] In addition, generally, an electron injection layer, an electron transport layer or a hole blocking layer in an organic light-emitting device is disposed between a cathode and a light-emitting layer. As a specific example, a hole blocking layer is disposed on the light-emitting layer, an electron transport layer is disposed on the hole blocking layer, and an electron injection layer is disposed on the electron transport layer, but the present invention is not limited to the above examples.

[0496] In an exemplary embodiment of the present invention, an organic material layer having a multilayer structure included in an organic light-emitting device includes: one or more layers selected from 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 a light-emitting layer, the light-emitting layer being disposed between a first electrode and a second electrode, the one or more layers being disposed between the first electrode and the light-emitting layer, and the one or more layers containing a compound represented by Chemical Formula 1 and / or a first solvent represented by Chemical Formula A.

[0497] Figure 1 The structure of an organic light emitting device according to an exemplary embodiment of the present invention is shown. Figure 1The structure of an organic light emitting device in which a first electrode 201 , a hole injection layer 301 , a hole transport layer 401 , a light emitting layer 501 , an electron injection and transport layer 601 , and a second electrode 701 are sequentially stacked on a substrate 101 is illustrated. Figure 1 The hole injection layer 301 and / or the hole transport layer 401 include the above-mentioned ink composition or a cured product thereof, or may be formed using the ink composition.

[0498] Figure 1 The organic light emitting device according to an exemplary embodiment of the present specification is illustrated, but the structure of the organic light emitting device of the present invention is not limited thereto.

[0499] As described above, the organic light emitting device having an organic material layer having a single-layer or multi-layer structure may have, for example, the following stack structure, but the stack structure is not limited thereto.

[0500] (1) Anode / hole transport layer / light-emitting layer / cathode

[0501] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0502] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0503] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0504] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0505] (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0506] (7) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0507] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0508] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0509] (10) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0510] (11) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0511] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0512] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0513] (14) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0514] (15) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0515] (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0516] (17) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0517] (18) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode / encapsulation

[0518] (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 / encapsulation body

[0519] In the structure, "electron transport layer / electron injection layer" may be replaced with "electron injection and transport layer" or "layer that simultaneously injects and transports electrons".

[0520] Furthermore, in the structure, “hole injection layer / hole transport layer” may be replaced with “hole injection and transport layer” or “layer that simultaneously injects and transports holes”.

[0521] In an exemplary embodiment of the present invention, the first electrode is an anode, and the second electrode is a cathode.

[0522] In an exemplary embodiment of the present invention, the first electrode is a cathode, and the second electrode is an anode.

[0523] In an exemplary embodiment of the present invention, the organic light emitting device may be a normal type organic light emitting device in which an anode, an organic material layer having one or more layers, and a cathode are sequentially stacked on a substrate.

[0524] In an exemplary embodiment of the present invention, the organic light emitting device may be an inverted organic light emitting device in which a cathode, an organic material layer having one or more layers, and an anode are sequentially stacked on a substrate.

[0525] In an exemplary embodiment of the present invention, in an organic light emitting device, one or more layers of an organic material layer are formed using the above-mentioned ink composition. In addition, the organic light emitting device can be manufactured by materials and methods known in the art.

[0526] For example, the organic light-emitting device of the present invention can be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. In this case, the organic light-emitting device can be manufactured by depositing a metal, or a conductive metal oxide, or an alloy thereof on a substrate to form an anode by using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation, and forming an organic material layer including 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 one or more layers of the electron transport and injection layer on the anode by a solution method, a deposition method, etc., and then depositing a material that can be used as a cathode on the organic material layer. In addition to such a method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0527] As the anode material, a material having a high work function is generally preferred to facilitate hole injection into the organic material layer. Examples thereof include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline; etc., but are not limited thereto.

[0528] As the cathode material, a material with a low work function is generally preferred to facilitate electron injection into the organic material layer. Examples thereof include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; etc., but are not limited thereto.

[0529] The light-emitting layer may include a host material and / or a dopant material.

[0530] Examples of host materials include fused aromatic ring derivatives, heterocyclic compounds, etc. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and specific examples of heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but examples are not limited thereto.

[0531] Examples of dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and examples thereof include pyrene, anthracene, In addition, the styrylamine compound is a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamine groups are substituted or unsubstituted. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but are not limited thereto. In addition, examples of metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0532] The hole injection layer is a layer that receives holes from the electrode. Preferably, the hole injection material has the ability to transport holes, and has the effect of receiving holes from the anode and an excellent hole injection effect on the light-emitting layer or the light-emitting material. In addition, the hole injection material is preferably a material that is excellent in the ability to prevent the excitons generated by the light-emitting layer from moving to the electron injection layer or the electron injection material. In addition, the hole injection material is preferably a material that is excellent in the ability to form a thin film. In addition, the HOMO of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. Specific examples of hole injection materials include: metal porphyrins, oligothiophenes, and organic materials based on arylamines; organic materials based on hexanitrile hexaazatriphenylene; organic materials based on quinacridone; organic materials based on perylene; conductive polymers based on polythiophene, such as anthraquinone and polyaniline; compounds of the above chemical formula 1; etc., but are not limited thereto.

[0533] In an exemplary embodiment of the present invention, the hole injection layer is formed of the above-mentioned ink composition or a cured product thereof.

[0534] In an exemplary embodiment of the present invention, the compound of Chemical Formula 1 is included as a host of a hole injection layer.

[0535] In an exemplary embodiment of the present invention, an ionic compound is included as a dopant of the hole injection layer.

[0536] The hole transport layer is a layer that receives holes from the hole injection layer and transfers the holes to the light-emitting layer, and may have a single-layer structure or a multilayer structure having two or more layers. The hole transport material is preferably a material having a high hole mobility that can receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples of hole transport materials include organic materials based on arylamine, compounds based on carbazole, conductive polymers, block copolymers having both conjugated and non-conjugated parts, etc., but are not limited thereto.

[0537] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. The electron transport material is preferably a material with high electron mobility that can well receive electrons from the cathode and transfer the electrons to the light-emitting layer. Specific examples thereof include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavone-metal complexes; and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the relevant technology. In particular, suitable cathode materials are typical materials with low work functions, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

[0538] The electron injection layer is a layer that receives electrons from the electrode. Preferably, the electron injection material is excellent in the ability to transport electrons and has an effect of receiving electrons from the cathode and an excellent electron injection effect to the light-emitting layer or the light-emitting material. In addition, the electron injection material is preferably a material that prevents the excitons generated by the light-emitting layer from moving to the hole injection layer and is excellent in the ability to form a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylmethane, anthrone, etc., and derivatives thereof; metal complex compounds; nitrogen-containing 5-membered ring derivatives; etc., but not limited thereto. Examples of metal complex compounds include 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) chlorogallium, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, bis(2-methyl-8-quinoline)(2-naphthol) gallium, etc., but not limited thereto.

[0539] The electron blocking layer is a layer that can improve the service life and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection 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 the layer that simultaneously injects and transports holes, using the compound of the above chemical formula 2.

[0540] The hole blocking layer is a layer that blocks holes from reaching the cathode and can generally be formed under the same conditions as those of the electron injection layer. Specific examples of hole blocking layer materials include Oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, aluminum complexes, etc., but not limited thereto.

[0541] The hole injection and transport layer may contain the materials used for the hole injection layer and the hole transport layer described above.

[0542] The electron injection and transport layer may contain the materials used for the electron injection layer and the hole transport layer described above.

[0543] When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0544] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a dual emission type according to the materials used.

[0545] An exemplary embodiment of the present invention provides an electronic device including an organic light emitting device including the above-mentioned ink composition or a cured product thereof, or including an organic material layer formed using the ink composition.

[0546] The electronic device may include all of the following: interlayer insulating film of a semiconductor device, a color filter, a black matrix, an outer coating, a columnar spacer, a passivation film, a buffer coating film, a multilayer printed board insulating film, a covering coating of a flexible copper clad laminate, a buffer coating film, a multilayer printed board insulating film, a solder resist film, an insulating film of an OLED, a protective film of a thin film transistor of a liquid crystal display device, an electrode protective film and a semiconductor protective film of an organic EL device, an OLED insulating film, an LCD insulating film, a semiconductor insulating film, a solar light module, a touch panel, a display device such as a display panel, etc., but is not limited thereto.

[0547] Embodiments of the invention

[0548] Hereinafter, the present invention will be described in detail with reference to the embodiments for specifically describing the present invention. However, embodiments according to the present invention may be modified into various forms, and should not be interpreted as limiting the scope of the present invention to the embodiments to be described below. Embodiments of the present invention are provided to more fully illustrate the present invention to those of ordinary skill in the art.

[0549] <Synthesis Example A. Preparation of Compounds>

[0550] Synthesis Example A-1. Synthesis of Compound H-1

[0551] (1) Synthesis of intermediate 1-1

[0552]

[0553] Compound a-1 (1.0 equivalent), compound a-2 (2.1 equivalent), sodium tert-butoxide (NaOtBu) (4.0 equivalent) and toluene (0.1M) are placed in a flask, and the resulting mixture is stirred at 40°C to 50°C. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (Pd(PtBu3)2) (0.08 equivalent) is added thereto, and the resulting mixture is stirred at 95°C. After determining whether the reaction is completely carried out, water is added to terminate the reaction. After layering by adding ethyl acetate (EA) thereto, the aqueous layer is separated into layers using ethyl acetate again. Magnesium sulfate (MgSO4) is added to the organic layer, and the resulting mixture is stirred and then filtered. The filtered mixture is purified by column chromatography to obtain intermediate 1-1. The intermediate is determined by LC-MS.

[0554] MS: [M+H]+=438.4

[0555] (2) Synthesis of Compound H-1

[0556]

[0557] Intermediate 1-1 (1.0 equivalent), compound a-3 (2.1 equivalent), NaOtBu (4.0 equivalent) and toluene (0.1M) were placed in a flask, and the resulting mixture was stirred at 40°C to 50°C. Thereafter, Pd(PtBu3)2 (0.08 equivalent) was added thereto, and the resulting mixture was stirred at 95°C. After determining whether the reaction was completely carried out, water was added to terminate the reaction. After stratification by adding ethyl acetate thereto, the aqueous layer was separated into layers using ethyl acetate again. Magnesium sulfate was added to the organic layer, and the resulting mixture was stirred and then filtered. The filtered mixture was purified by column chromatography to obtain compound H-1. The compound was purified by LC-MS, 1 Confirmed by H-NMR.

[0558] MS:[M + H] + =1179.4

[0559] 1H NMR (500MHz): δ=8.2-6.85(m,64H),6.8-6.7(m,2H),5.8-5.7(d,2H),

[0560] 5.3-5.2(d,2H),2.4-2.2(d,12H)

[0561] Synthesis Example A-2. Synthesis of Compound H-2

[0562] (1) Synthesis of intermediate 1-2

[0563]

[0564] Compound b-1 (1.0 equivalent), compound b-2 (2.1 equivalent), NaOtBu (4.0 equivalent) and toluene (0.1M) were placed in a flask, and the resulting mixture was stirred at 40°C to 50°C. Thereafter, Pd(PtBu3)2 (0.08 equivalent) was added thereto, and the resulting mixture was stirred at 95°C. After determining whether the reaction was completely carried out, water was added to terminate the reaction. After layering by adding ethyl acetate thereto, the aqueous layer was separated into layers using ethyl acetate again. Magnesium sulfate was added to the organic layer, and the resulting mixture was stirred and then filtered. The filtered mixture was purified by column chromatography to obtain intermediate 1-2. The intermediate was determined by LC-MS.

[0565] MS:[M + H] + =386.4

[0566] (2) Synthesis of Compound H-2

[0567]

[0568] Intermediate 1-2 (1.0 equivalent), compound b-3 (2.1 equivalent), NaOtBu (4.0 equivalent) and toluene (0.1M) were placed in a flask, and the resulting mixture was stirred at 40°C to 50°C. Thereafter, Pd(PtBu3)2 (0.08 equivalent) was added thereto, and the resulting mixture was stirred at 95°C. After determining whether the reaction was completely carried out, water was added to terminate the reaction. After stratification by adding ethyl acetate thereto, the aqueous layer was separated into layers using ethyl acetate again. Magnesium sulfate was added to the organic layer, and the resulting mixture was stirred and then filtered. The filtered mixture was purified by column chromatography to obtain compound H-2. The compound was purified by LC-MS, 1 Confirmed by H-NMR.

[0569] MS:[M + H] + =1291.4

[0570] 1H NMR (500MHz): δ=8.3-6.9 (m, 84H), 6.8-6.7 (m, 2H), 5.8-5.7 (d, 2H), 5.3-5.2

[0571] (d,,22H)

[0572] Synthesis Example A-3. Synthesis of Compound H-3

[0573] (1) Synthesis of intermediate 1-3

[0574]

[0575] Compound c-1 (1.0 equivalent), compound c-2 (2.1 equivalent), NaOtBu (4.0 equivalent) and toluene (0.1M) were placed in a flask, and the resulting mixture was stirred at 40°C to 50°C. Thereafter, Pd(PtBu3)2 (0.08 equivalent) was added thereto, and the resulting mixture was stirred at 95°C. After determining whether the reaction was completely carried out, water was added to terminate the reaction. After layering by adding ethyl acetate thereto, the aqueous layer was separated into layers using ethyl acetate again. Magnesium sulfate was added to the organic layer, and the resulting mixture was stirred and then filtered. The filtered mixture was purified by column chromatography to obtain intermediate 1-3. The intermediate was determined by LC-MS.

[0576] MS:[M + H] + =690.7

[0577] (2) Synthesis of Compound H-3

[0578]

[0579] Intermediate 1-3 (1.0 equivalent), compound c-3 (2.1 equivalent), NaOtBu (4.0 equivalent) and toluene (0.1M) were placed in a flask, and the resulting mixture was stirred at 40°C to 50°C. Thereafter, Pd(PtBu3)2 (0.08 equivalent) was added thereto, and the resulting mixture was stirred at 95°C. After determining whether the reaction was completely carried out, water was added to terminate the reaction. After stratification by adding ethyl acetate thereto, the aqueous layer was separated into layers using ethyl acetate again. Magnesium sulfate was added to the organic layer, and the resulting mixture was stirred and then filtered. The filtered mixture was purified by column chromatography to obtain compound H-3. The compound was purified by LC-MS, 1 Confirmed by H-NMR.

[0580] MS:[M + H] + =1559.8

[0581] 1H NMR (500MHz): δ=8.1-6.9(m,108H), 6.8-6.7(m2H),5.8-5.7(d,2H)

[0582] 5.3-5.2(d,2H)

[0583] Synthesis Example 4. Synthesis of Compound H-4

[0584] (1) Synthesis of intermediates 1-4

[0585]

[0586] Compound d-1 (1.0 equivalent), compound d-2 (2.1 equivalent), NaOtBu (4.0 equivalent) and toluene (0.1M) were placed in a flask, and the resulting mixture was stirred at 40°C to 50°C. Thereafter, Pd(PtBu3)2 (0.08 equivalent) was added thereto, and the resulting mixture was stirred at 95°C. After determining whether the reaction was completely carried out, water was added to terminate the reaction. After layering by adding ethyl acetate thereto, the aqueous layer was separated into layers using ethyl acetate again. Magnesium sulfate was added to the organic layer, and the resulting mixture was stirred and then filtered. The filtered mixture was purified by column chromatography to obtain intermediate 1-4. The intermediate was determined by LC-MS.

[0587] MS:[M + H] + =562.7

[0588] (2) Synthesis of Compound H-4

[0589]

[0590] Intermediate 1-4 (1.0 equivalent), compound d-3 (2.1 equivalent), NaOtBu (4.0 equivalent) and toluene (0.1M) were placed in a flask, and the resulting mixture was stirred at 40°C to 50°C. Thereafter, Pd(PtBu3)2 (0.08 equivalent) was added thereto, and the resulting mixture was stirred at 95°C. After determining whether the reaction was completely carried out, water was added to terminate the reaction. After stratification by adding ethyl acetate (EA) thereto, the aqueous layer was separated into layers using ethyl acetate [EA]. Magnesium sulfate was added to the organic layer, and the resulting mixture was stirred and then filtered. The filtered mixture was purified by column chromatography to obtain compound H-4. The compound was purified by LC-MS, 1 Confirmed by H-NMR.

[0591] MS:[M + H] + =1435.8

[0592] 1HNMR (500MHz): δ=8.0-7.8(m,4H),7.7-6.9(m,52H),6.8-6.7(m,2H),5.8-5.7

[0593] (d,2H),5.3-5.2(d,2H),1.4-1.3(s,18H)

[0594] Synthesis Example 5. Synthesis of Compound H-5

[0595] (1) Synthesis of intermediate 1-5

[0596]

[0597] Compound e-1 (1.0 equivalent), compound e-2 (2.1 equivalent), NaOtBu (4.0 equivalent) and toluene (0.1M) were placed in a flask, and the resulting mixture was stirred at 40°C to 50°C. Thereafter, Pd(PtBu3)2 (0.08 equivalent) was added thereto, and the resulting mixture was stirred at 95°C. After determining whether the reaction was completely carried out, water was added to terminate the reaction. After layering by adding ethyl acetate thereto, the aqueous layer was separated into layers using ethyl acetate again. Magnesium sulfate was added to the organic layer, and the resulting mixture was stirred and then filtered. The filtered mixture was purified by column chromatography to obtain intermediate 1-5. The intermediate was determined by LC-MS.

[0598] MS:[M + H] + =532.8

[0599] (2) Synthesis of Compound H-5

[0600]

[0601] Intermediate 1-5 (1.0 equivalent), compound e-3 (2.1 equivalent), NaOtBu (4.0 equivalent) and toluene (0.1M) were placed in a flask, and the resulting mixture was stirred at 40°C to 50°C. Thereafter, Pd(PtBu3)2 (0.08 equivalent) was added thereto, and the resulting mixture was stirred at 95°C. After determining whether the reaction was completely carried out, water was added to terminate the reaction. After stratification by adding ethyl acetate thereto, the aqueous layer was separated into layers using ethyl acetate again. Magnesium sulfate was added to the organic layer, and the resulting mixture was stirred and then filtered. The filtered mixture was purified by column chromatography to obtain compound H-5. The compound was purified by LC-MS, 1 Confirmed by H-NMR.

[0602] MS:[M + H] +=1253.7

[0603] 1HNMR (500MHz): δ=8.0-6.9(m,40H),6.8-6.7(m,4H),5.8-5.7(d,2H),5.3-5.2

[0604] (d,2H),2.3(s,6H),2.0(s,6H),1.5-1.3(m,12H),0.9(t,6H)

[0605] <Synthesis Example B. Preparation of Ionic Compounds>

[0606] Synthesis Example B-1. Preparation of Compound DA

[0607] (1) Preparation of Compound F-1

[0608]

[0609] 1-Bromo-2,3,5,6-tetrafluoro-4-vinylbenzene (2g, 7.8428mmol) was placed in 20mLTHF in a 50mL round-bottom flask, and the resulting solution was stirred at -78°C for 30 minutes. n-BuLi (3.45mL, 8.6271mmol, 2.5M in hexane solution) was slowly added to the solution, and the resulting mixture was stirred at -78°C for 30 minutes. BCl3 (2.6mL, 2.6142mmol, 1M in heptane solution) was added to the reaction solution at -78°C over 15 minutes. The resulting solution was slowly warmed to room temperature, the reaction solution was stirred overnight, and then 30mL of water was added thereto. The synthesized substance was extracted with EA (3×10mL), and the solvent was completely removed. Water was completely removed using benzene by Dean-stock, and the solid was filtered to prepare 800mg of compound F-1. (yield: 43%).

[0610] (2) Preparation of compound DA

[0611]

[0612] Compound F-1 (400 mg, 0.5569 mmol), diphenyl iodonium chloride (176 mg, 0.5569 mmol), 10 mL of H2O and 10 mL of acetone were placed in a 25 mL round-bottom flask and stirred vigorously for 30 minutes. Extraction was performed using dichloromethane to remove and dry the solvent. After the solvent was completely removed, water was completely removed using benzene by Dean-stock, and the solid was filtered to prepare 340 mg of the target compound DA. (Yield: 28%) The synthesis of the compound was confirmed by LC-MS and NMR.

[0613] MS: [MH]-=711 (negative mode)

[0614] MS: [M+H]+=281 (positive mode)

[0615] Figure 2 The results of NMR measurement of Compound DA are shown.

[0616] Synthesis Example B-2. Preparation of Compound DB

[0617] (1) Preparation of Compound F-2

[0618]

[0619] Under nitrogen atmosphere, Mg (193mg, 7.9208mmol), I2 (4mg) and tetrahydrofuran (THF) (10mL) are put into 100mL round-bottom flask, and the resulting mixture is stirred for 30 minutes. 4-bromostyrene (1.04mL, 7.9208mmol) is put thereinto, a water bath of 30°C is placed under the round-bottom flask, and the resulting mixture is stirred overnight. It is determined that the reaction solution has turned black and Mg has dissolved therein. The reaction solution is diluted by adding 5mL ether thereto. Tris (pentafluorophenyl) borane (1g, 3.9604mmol) is dissolved in 5mL ether, and the resulting solution is slowly added to the reaction solution over 30 minutes. The solution is stirred overnight. Na2CO3 (0.1M, 80mL, 8.0mmol) is slowly added to the reaction solution. EA is used to extract the organic solvent, and MgSO4 is used to remove residual water. In addition, benzene is distilled by using Dean-stock to remove residual water and impurities. When about 10 mL of the solvent remained, the solution was cooled and filtered to prepare 1.6 g of compound F-2. (Yield: 64%).

[0620] (2) Preparation of compound DB

[0621]

[0622] Compound F-2 (100 mg, 0.1567 mmol), 10 mL of distilled water and PhICl (60 mg, 0.1881 mmol) were placed in a 25 mL round bottom flask and stirred for 1 hour. When 15 mL of acetone was added to the reaction solution, a precipitate was produced, and the precipitate was filtered and dried to prepare 140 mg of compound DB. (Yield: 100%) The synthesis of the compound was determined by LC-MS and NMR.

[0623] MS: [MH]-=615 (negative mode)

[0624] MS: [M+H]+=281 (positive mode)

[0625] Figure 3 The NMR measurement results of Compound DB are shown.

[0626] <Preparation of ink composition>

[0627] Preparation Example 1. Preparation of Ink Composition 1

[0628] Compound H-1 prepared in Synthesis Example A-1 and Compound DA prepared in Synthesis Example B-1 were mixed at a weight ratio of 8:2 to prepare Mixture 1. Thereafter, Mixture 1 was added to a solvent in which 3-isopropylbiphenyl (a first solvent represented by Chemical Formula A) and dibutyl oxalate (another solvent) were mixed at 20 wt % and 80 wt %, respectively, so that the concentration was 2 wt %, and then the resulting mixture was stirred for 24 hours to prepare Ink Composition 1.

[0629] Preparation Examples 2 to 71. Preparation of Ink Compositions 2 to 71

[0630] Ink compositions 2 to 71 were prepared in the same manner as in Preparation Example 1, except that the materials shown in the following Table 1 were each used instead of Compound H-1, Compound DA, the first solvent, and the additional solvent.

[0631] In this case, when two types are used as the additional solvent, the solvent of Chemical Formula A, the first additional solvent, and the second additional solvent are mixed at 20 wt %, 50 wt %, and 30 wt %, respectively.

[0632] *Host compound of hole injection layer (HIL host)

[0633]

[0634] *Hole injection layer dopant compound (HIL dopant)

[0635]

[0636] [Table 1]

[0637]

[0638]

[0639]

[0640]

[0641] <Experimental Example A>

[0642] Example 1-1.

[0643] The ink composition 1 was printed on a substrate on which a plurality of pixels were formed in the form of lines. The printed substrate was placed in a vacuum chamber, and a high vacuum (1×10 -6 The film was cured by heat treatment in a glove box (N2 atmosphere, 230°C hot plate condition) for 30 minutes.

[0644] Figure 4 A line bank inkjet substrate is shown to which an ink composition is applied.

[0645] Figure 5 Application of an ink composition to a line bank inkjet substrate is shown.

[0646] Figure 6 The ink composition is shown to be formed as a thin film on a line bank inkjet substrate.

[0647] Figure 7 is a diagram showing a plan view of an organic material layer in which a line bank is formed. Figure 7 In FIG. 1 , the ink composition is printed in the direction from (a) to (b) (arrow direction), and in this case, the (a) or (b) portion is indicated as an edge.

[0648] Examples 1-2 to 1-45 and Comparative Examples 1-1 to 1-24

[0649] An organic material 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 Ink Composition 1 in Example 1-1, and the thickness of the pixel was measured.

[0650] The following Table 2 shows that, by selecting a line among a plurality of pixels in which the ink compositions prepared in Examples 1-1 to 1-45 and Comparative Examples 1-1 to 1-24 are formed into thin films to compare the average thickness of 10 pixels positioned at the center of the line with the thickness of pixels positioned at the edge portion of the line, a thin film having a thickness deviation of 5 nm or less is positioned at the nth pixel from the edge.

[0651] In this case, the thickness of the pixel included in the cured thin film was measured using an optical profiler (model name: Contour GT-I) manufactured by Bruker, which is an optical thickness measuring device.

[0652] Specifically, in the line bank in which 70 pixels are formed as a row, the average thickness of the 31st to 40th pixels is compared with the thickness of the i-th pixel at the edge, and the minimum value of i of ±5 nm is shown in the following Table 2. In this case, a small number of i means that the thickness is uniformly formed to a position close to the edge (that is, the thickness uniformity is improved).

[0653] [Table 2]

[0654]

[0655]

[0656]

[0657] From Table 2 above, it can be determined that in the case of Examples 1-1 to 1-45, the pixels showing ±5nm from the center average thickness are positioned at the 5th or less position from the edge, while in the case of Comparative Examples 1-1 to 1-24, the pixels are positioned at the 6th or more position from the edge.

[0658] In this regard, Fig. 9 and Fig.10 1 shows the thickness uniformity characteristics of a pixel according to an embodiment of the present invention. Specifically, Fig. 9 shows the thickness uniformity of the pixels measured in Example 1-1, and Fig.10 Graph 1-1 shows the thickness uniformity of the pixels measured in Comparative Example 1-1. Fig. 9 and Fig.10 In FIG. 1 , the horizontal axis means the pitch between pixels (μm), and the vertical axis means the thickness of the pixel (nm). Fig. 9 and Fig.10 , it can be determined that in Example 1-1 ( Figure 8 ), the number of pixels in which the thin film is formed thick even at the edge portion is small, whereas in Comparative Example 1-1 ( Fig.10 ), the number of pixels in which the film is formed thick increases toward the edge portion, and the thickness of the film also becomes larger.

[0659] Thus, it can be seen that when the ink composition according to an exemplary embodiment of the present invention is used, the thickness uniformity is improved. Therefore, when the ink composition is used in an organic material layer in an organic light-emitting device, etc., by reducing the factors that affect the interference conditions of the emitted light according to the thickness, excellent luminescence and / or color rendering effects can be expected. In contrast, when an ink composition that does not conform to the present invention is used, the thickness difference between pixels is large, and the thickness uniformity is uneven, so that when the ink composition is applied to an organic material layer in an organic light-emitting device, etc., it can be expected that the performance of the device will deteriorate.

[0660] Example 2-1.

[0661] 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 a high vacuum (1×10 -6The film was cured by heat treatment in a glove box (N2 atmosphere, 230°C hot plate condition) for 30 minutes.

[0662] Figure 8 is a diagram showing a plan view of an organic material layer in which a separation bank is formed. Figure 8 In FIG. 1 , the ink composition is printed in the direction from (a) to (b) (arrow direction), and in this case, the (a) or (b) portion is indicated as an edge.

[0663] Examples 2-2 to 2-27 and Comparative Examples 2-1 to 2-14

[0664] An organic material 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 Ink Composition 1 in Example 2-1, and the film height step in the pixel was measured.

[0665] In this case, the thin film height step in the pixel was measured using an optical profiler manufactured by Bruker (model name: Contour GT-I), which is a thin film thickness measuring device.

[0666] The film height step between the portion corresponding to 20% of the pixel length and the portion corresponding to 80% of the pixel length in one pixel was measured, and the minimum value of i of ±5 nm is shown in the following Table 3. In this case, i means the i-th pixel from the edge. In addition, a small value of i means that the thickness of the film in the pixel is uniformly formed to a position close to the edge (that is, the thickness uniformity is improved).

[0667] [Table 3]

[0668]

[0669]

[0670] The fact that the height step between the portion corresponding to 20% of the pixel length and the portion corresponding to 80% of the pixel length is ±5 nm (ie, the absolute value of the height difference is 5 nm or less) means that the thickness of the thin film is formed uniform in the pixel.

[0671] From Table 3, it can be confirmed that in Examples 2-1 to 2-27, the thin film in the pixel is symmetrically formed without being inclined to one side even at the pixel closer to the edge portion, compared with Comparative Examples 2-1 to 2-14. That is, it can be confirmed that when the ink composition according to an exemplary embodiment of the present invention is applied, the thickness of the thin film is formed to be uniform even at the pixel closer to the edge, compared with when other ink compositions are applied.

[0672] Thus, in the ink composition of the present invention, since the ink composition is used in an organic material layer in an organic light-emitting device, etc., excellent light emission and / or color development effects can be expected by reducing factors that affect interference conditions of emitted light according to thickness. In contrast, when an ink composition not conforming to the present invention is used, a thin film on the edge side is not formed uniformly, so that when the ink composition is applied to an organic material layer in an organic light-emitting device, etc., it can be expected that the performance of the device will deteriorate.

[0673] <Experimental Example B>

[0674] Example 3-1.

[0675] The film is coated with A glass substrate with a thickness of ITO (indium tin oxide) and patterned with a hydrophobic embankment was washed with distilled water for 30 minutes and then dried on a hot plate at 230°C for 10 minutes. The ink composition 1 in Table 1 was inkjet printed on the washed substrate with a patterned embankment and heat treated at 230°C for 30 minutes to form a hole injection layer with a thickness of 30nm. A hole transport layer with a thickness of 40nm was formed on the hole injection layer by inkjet printing of an ink prepared by dissolving the following α-NPD compound in cyclohexylbenzene at a concentration of 2% by weight. Thereafter, the glass substrate was transferred to a vacuum deposition machine, and the following ADN compound and the following DPAVBi compound were vacuum deposited on the hole transport layer at a weight ratio of 20:1 (ADN:DPAVBi) to have a thickness of 20nm, thereby forming a light-emitting layer. The following BCP compound was vacuum deposited on the light-emitting layer to have a thickness of 35nm, thereby forming an electron injection and transport layer. A cathode was formed on the electron injection and transport layer by sequentially depositing LiF and aluminum to have thicknesses of 1 nm and 100 nm, respectively, thereby manufacturing an organic light emitting device.

[0676]

[0677] Examples 3-2 to 3-46.

[0678] 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 Ink Composition 1 in Example 3-1.

[0679] [Table 4]

[0680]

[0681]

[0682] It was confirmed that the organic light emitting devices manufactured in Examples 3-1 to 3-46 were driven. Thus, it was confirmed that the ink composition according to the exemplary embodiment of the present invention can be applied to the organic light emitting device.

[0683] Comparative Examples 3-1 to 3-4.

[0684] Ink compositions 72 to 75 were prepared in the same manner as in Preparation Example 1, except that the materials shown in the following Table 5 were each used instead of Compound H-1, Compound DA, the first solvent, and the additional solvent.

[0685] Thereafter, an organic light-emitting device was manufactured in the same manner as in Example 3-1, except that the ink composition in the following Table 6 was used instead of the ink composition 1 in Example 3-1.

[0686] The structures of compounds X-1 to X-4 used in the following Table 5 are as follows.

[0687]

[0688] [Table 5]

[0689]

[0690] The efficiency and lifespan values ​​of the organic light emitting devices manufactured in Examples 3-1, 3-17, 3-29 and 3-31 and the organic light emitting devices manufactured in Comparative Examples 3-1 to 3-4 were compared and shown in Table 6 below.

[0691] The relative efficiency values ​​and relative service life values ​​in Table 6 below were obtained as follows.

[0692] *Relative efficiency value: Efficiency of Example X / Efficiency of Examples 3-29

[0693] *T95 relative value: T95 of Example X / T95 of Examples 3-29

[0694] (Example X: Examples 3-1, 3-17, 3-29 and 3-31, and Comparative Examples 3-1, 3-2, 3-3 or 3-4)

[0695] In this case, T95 means lifetime, and is a value measured as the time taken to reach 95% of the initial brightness under a constant current condition of 1000 nits.

[0696] [Table 6]

[0697] Ink composition Relative efficiency value T95 relative value Example 3-1 1 1.05 1.01 Example 3-17 17 1.02 0.95 Example 3-29 29 1 1 Example 3-31 31 1.01 0.98 Comparative Example 3-1 72 0.9 0.80 Comparative Example 3-2 73 0.89 0.81 Comparative Example 3-3 74 0.92 0.87 Comparative Examples 3-4 75 0.91 0.85

[0698] As can be seen from Tables 5 and 6, when the host is changed in the ink composition of the present specification, the efficiency and lifespan of the organic light emitting device are deteriorated.

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: [Chemical formula 1] [Chemical formula A] in, In Chemical Formula 1 and Chemical Formula A, Y1 to Y10 are the same as or different from each other and are each independently hydrogen; deuterium; hydroxyl; ether; carbonyl; ester; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted cycloalkenyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryl; or substituted or unsubstituted amino, Lc is a substituted or unsubstituted heteroarylene group containing O, S or Si, L1 and L2 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group, L11 and L12 are the same as or different from each other and are each independently a direct bond; -O-; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group, Ar1 to Ar4 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, R1 and R2 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group, X1 and X2 are the same or different from each other and are each independently a curable group, r1 and r2 are each an integer from 0 to 7, and when r1 and r2 are each 2 or more, the two or more substituents in the brackets are the same as or different from each other, l11 and l12 are each an integer of 1 to 3, and when l11 and l12 are each 2 or more, two or more substituents in the brackets are the same as or different from each other, f1 is 0 to the maximum number of substituents that can be bonded to Ar1, f2 is 0 to the maximum number of bonds that the substituent can bond to Ar2, f3 is 0 to the maximum bondable number of substituents that can be bonded to Ar3, and f4 is 0 to the maximum possible number of bonds that a substituent can bond to Ar4.

2. The ink composition according to claim 1, wherein the curable group is any one of the following structures: In the structure described, R32 and R34 are the same as or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group, L31 to L38 are the same as or different from each other and are each independently a direct bond; -O-; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group, l34 to l38 are each an integer of 1 to 10, and when l34 to l38 are each 2 or more, two or more substituents in the brackets are the same as or different from each other, and is a portion bonded to Chemical Formula 1.

3. The ink composition according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 1-1: [Chemical formula 1-1] In Chemical Formula 1-1, Cy1 and Cy2 are the same as or different from each other and are each independently a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms, Y is O, S or SiRy1Ry2, Ry1 and Ry2 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl, and L1, L2, L11, L12, Ar1 to Ar4, R1, R2, X1, X2, r1, r2, l11, l12 and f1 to f4 are the same as those defined in Chemical Formula 1.

4. The ink composition according to claim 1, wherein Lc is any one of the following structures, and the following structures are unsubstituted or substituted with another substituent: In the structure described, Ry1 and Ry2 are the same as or different from each other and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and is a portion connected to Chemical Formula 1. The ink composition according to claim 1 , wherein f1 to f4 are each an integer of 0 to 9. 6 . The ink composition according to claim 1 , wherein f1+f2+f3+f4 is an integer of 1 or more.

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

8. The ink composition according to claim 1, wherein the solvent represented by Chemical Formula A is any one of the following structures:

9. The ink composition according to claim 1, wherein the compound represented by Chemical Formula 1 is any one of the following structures:

10. The ink composition according to claim 1, further comprising a second solvent, wherein the second solvent comprises one or more of the following: a solvent represented by any one of the following Chemical Formulas B to D, methoxytoluene, and tetralin: [Chemical formula B] [Chemical formula C] [Chemical formula D] In Chemical Formulae B to D, L50 is a direct bond; or an alkylene group, L51 and L53 to L55 are the same as or different from each other, and are each independently a direct bond; -O-; or a substituted or unsubstituted alkylene group, L52 is -COO-, R50, R51 and R54 to R56 are the same as or different from each other and are each independently a substituted or unsubstituted alkyl group, R53 is hydrogen; deuterium; alkoxy; or substituted or unsubstituted alkyl, a1 is 0 or 1, r53 is an integer of 1 to 5, and when r53 is 2 or more, two or more R53 are the same as or different from each other, and l50, l51, and l53 to l55 are each an integer of 1 to 10, and when l50, l51, and l53 to l55 are each 2 or more, two or more structures in the brackets are the same as or different from each other.

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

12. The ink composition according to claim 1, further comprising an ionic compound containing an anionic group represented by the following Chemical Formula 2: [Chemical formula 2] in, In chemical formula 2, At least one of R201 to R220 is F; cyano; or a substituted or unsubstituted fluoroalkyl group, At least one of the other R201 to R220 is a curable group, The remaining R201 to R220 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitro group; a cyano group; an amino group; -OR221; -SR222; -SO3R223; -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 amino group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and R221 to R228 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

13. The ink composition according to claim 12, wherein Chemical Formula 2 is any one of the following structures: In the structure described, 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; a halogen group; a nitro group; a cyano group; an amino group; -OR221; -SR222; -SO3R223; -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 amino group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, R221 to R228 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group, and i is an integer of 1 to 4, and when i is 2 or more, two or more M1s are the same as or different from each other.

14. The ink composition according to claim 12, wherein the ionic compound further comprises a cationic group, and the cationic group is a monovalent cationic group, A compound or any of the following structures: In the structure described, Q30 to Q105 are the same as or different from each other and are each independently hydrogen; deuterium; cyano; nitro; halogen group; hydroxyl group; -COOR250; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryloxy group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or a curable group, R250 is hydrogen; deuterium; or substituted or unsubstituted alkyl, x is an integer from 0 to 10, and p1 is 1 or 2, q1 is 0 or 1, and p1+q1=2.

15. The ink composition according to claim 12, wherein the ionic compound is any one of the following chemical formulas D-1 to D-37: [Chemical formula D-37] 16 . The ink composition according to claim 1 , wherein the ink composition is a composition for forming one or more layers 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. 17 . A pixel comprising the ink composition according to claim 1 , or a cured product thereof.

18. An organic material layer comprising the pixel according to claim 17.

19. An organic light emitting device, comprising: a first electrode; a second electrode; as well as an organic material layer having one or more layers disposed between the first electrode and the second electrode, One or more of the organic material layers is the organic material layer according to claim 18.

20. The organic light emitting device according to claim 19, wherein the organic material layer comprises one or more layers 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 one or more layers 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 contain the ink composition or a cured product thereof.

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