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

Abstract

This invention relates to ink compositions, organic material layers comprising the same, and organic light-emitting devices comprising the same.

Description

Technical Field

[0001] This application claims priority and benefit to Korean Patent Application No. 10-2021-0122564, filed with the Korean Intellectual Property Office on September 14, 2021, the entire contents of which are incorporated herein by reference.

[0002] This invention relates to ink compositions, organic material layers comprising the same, and organic light-emitting devices comprising the same. Background Technology

[0003] Organic light emission (OLED) is one example of converting electric current into visible light through internal processes of specific organic molecules. The principle of OLED is as follows: When an organic material layer is placed between an anode and a cathode, and a current is applied between the two electrodes, electrons and holes are injected into the organic material layer from the cathode and anode, respectively. The injected electrons and holes recombine to form excitons, which then fall back to the ground state, emitting light. OLED devices utilizing this principle typically consist of a cathode, an anode, and an organic material layer disposed between them (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.).

[0004] In existing technologies, deposition methods are commonly used to manufacture organic light-emitting devices. However, deposition methods often result in material loss and make it difficult to fabricate devices with large areas. To address these issues, solution-based methods have been developed.

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

[0006] Technical issues

[0007] This invention relates to ink compositions, organic material layers comprising the same, and organic light-emitting devices comprising the same.

[0008] Technical solution

[0009] An exemplary embodiment of the present invention provides an ink composition comprising a compound represented by the following chemical formula 1 and a solvent represented by the following chemical formula A.

[0010] [Chemical Formula 1]

[0011]

[0012] [Chemical Formula A]

[0013]

[0014] In chemical formula 1 and chemical formula A,

[0015] Y can be O, S, CRaRb, or SiRcRd.

[0016] Cy1 and Cy2 may be the same as or different from each other, and each is independently a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring.

[0017] Ra, Rb, Rc, and Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, or bonded to adjacent groups to form substituted or unsubstituted rings.

[0018] L1 to L3 may be identical or different from each other, and each is an independent direct bond; or substituted or unsubstituted aryl groups.

[0019] L11 and L12 may be the same as or different from each other, and each is independently a direct bond; substituted or unsubstituted alkylene groups; or substituted or unsubstituted aryl groups.

[0020] X1 and X2 may be the same as or different from each other, and each is an independent curable group.

[0021] R1 and R2 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0022] R3 and R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0023] a, b, and c are each 0 or 1.

[0024] n1 and n2 are each integers from 0 to 7, and when n1 and n2 are each 2 or greater, the two or more substituents in parentheses are either the same or different from each other.

[0025] m1 and m2 are each integers from 1 to 5, n3 and n4 are each integers from 0 to 4, m1 + n3 is 5 or less, and m2 + n4 is 5 or less.

[0026] Y1 to Y10 may be the same as or different from each other, and each independently represents 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.

[0027] Another exemplary embodiment of the present invention provides a pixel comprising an ink composition or a cured product thereof.

[0028] Another exemplary embodiment of the present invention provides an organic material layer comprising the pixel.

[0029] Another exemplary embodiment of the present invention provides an organic light-emitting device comprising: 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 comprise the above-described ink composition or a cured product thereof.

[0030] Beneficial effects

[0031] The ink composition according to an exemplary embodiment of the present invention can be used as a material for the organic material layer of an organic light-emitting device, and a device with low driving voltage, excellent luminous efficiency and long service life can be obtained, or a solution method can be used to realize a large-area device.

[0032] The organic material layer comprising an ink composition according to an exemplary embodiment of the present invention has excellent flatness properties. Attached Figure Description

[0033] Figure 1 An organic light-emitting device according to an exemplary embodiment of the present invention is shown.

[0034] Figure 2 A line-dike inkjet substrate is shown having an ink composition according to an exemplary embodiment of the present invention applied thereon.

[0035] Figure 3 An ink composition according to an exemplary embodiment of the invention is shown applied to a line-dike inkjet substrate.

[0036] Figure 4 This illustration shows an ink composition according to an exemplary embodiment of this specification being formed as a thin film on a line-dike inkjet substrate.

[0037] Figure 5 The thickness of a pixel according to Embodiment 6 of the present invention is shown.

[0038] Figure 6 The thickness of a pixel according to Embodiment 16 of the present invention is shown.

[0039] Figure 7 The thickness of a pixel according to Comparative Example 5 of the present invention is shown.

[0040] Figure 8 The thickness of a pixel according to Comparative Example 10 of the present invention is shown.

[0041] Figure 9 The thickness of a pixel according to Comparative Example 15 of the present invention is shown.

[0042] Figure 10 The thickness of a pixel according to Comparative Example 27 of the present invention is shown.

[0043] Figure 11 The thickness of a pixel according to embodiment 36 of the present invention is shown.

[0044] Figure 12 The thickness of a pixel is shown in Embodiment 40 of the present invention.

[0045] Figure 13 The thickness of a pixel is shown in Comparative Example 29 according to the present invention.

[0046] Figure 14 The thickness of a pixel according to Comparative Example 30 of the present invention is shown.

[0047] Figure 15 The thickness of a pixel according to Comparative Example 31 of the present invention is shown.

[0048] Figure 16 The thickness of a pixel according to Comparative Example 32 of the present invention is shown.

[0049] 101: Base

[0050] 201: First electrode

[0051] 301: Hole Injection Layer

[0052] 401: Hole Transport Layer

[0053] 501: Emissive layer

[0054] 601: Electron Injection and Transport Layer

[0055] 701: Second electrode Detailed Implementation

[0056] The invention will be described in detail below.

[0057] An exemplary embodiment of the present invention provides an ink composition comprising a compound represented by the following chemical formula 1 and a solvent represented by the following chemical formula A.

[0058] [Chemical Formula 1]

[0059]

[0060] [Chemical Formula A]

[0061]

[0062] In chemical formula 1 and chemical formula A,

[0063] Y can be O, S, CRaRb, or SiRcRd.

[0064] Cy1 and Cy2 may be the same as or different from each other, and each is independently a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring.

[0065] Ra, Rb, Rc, and Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, or bonded to adjacent groups to form substituted or unsubstituted rings.

[0066] L1 to L3 may be identical or different from each other, and each is an independent direct bond; or substituted or unsubstituted aryl groups.

[0067] L11 and L12 may be the same as or different from each other, and each is independently a direct bond; substituted or unsubstituted alkylene groups; or substituted or unsubstituted aryl groups.

[0068] X1 and X2 may be the same as or different from each other, and each is an independent curable group.

[0069] R1 and R2 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0070] R3 and R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0071] a, b, and c are each 0 or 1.

[0072] n1 and n2 are each integers from 0 to 7, and when n1 and n2 are each 2 or greater, the two or more substituents in parentheses are either the same or different from each other.

[0073] m1 and m2 are each integers from 1 to 5, n3 and n4 are each integers from 0 to 4, m1 + n3 is 5 or less, and m2 + n4 is 5 or less.

[0074] Y1 to Y10 may be the same as or different from each other, and each independently represents 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.

[0075] Because the compound represented by Formula 1 according to an exemplary embodiment of the present invention contains two different types of substituents (specifically a halogenated aryl group and a curable group) and an amine group containing a tricyclic or higher-order ring, the formation of free radicals at the corresponding positions is suppressed, thereby enhancing the stability of the compound and resulting in a high highest occupied molecular orbital (HOMO) energy level and excellent hole mobility. For this reason, when the compound represented by Formula 1 is included in the hole injection layer of an organic light-emitting device, the compound promotes hole injection from the hole injection layer to the hole transport layer, enabling the acquisition of organic light-emitting devices with long lifespan characteristics, significantly impacting the improvement of device lifespan.

[0076] Because the solvent represented by chemical formula A according to an exemplary embodiment of the present invention contains biphenyl as a core structure, this solvent has excellent solubility in aromatic solutes contained in the ink composition. Furthermore, it has the advantage that the uniformity of the organic material layer can be improved by reducing thickness deviations according to the position of each pixel due to good leveling effects. Specifically, the ink composition can reduce thickness deviations between pixels that have been coated, dried, and heat-treated. Therefore, excellent luminescence and / or coloring effects can be expected by reducing factors affecting the interference conditions of light emitted from the light-emitting device according to the thickness.

[0077] When one component (layer) is disposed "on" another component (layer) in this invention, this includes not only the case where the one component (layer) is in contact with the other component, but also the case where there is another component (layer) between the two components (layers).

[0078] When a part of this invention "includes" a constituent element, unless otherwise specifically described, this does not mean that other constituent elements are excluded, but rather that other constituent elements may be included.

[0079] In this invention, "layer" has the same meaning as "film" commonly used in the art, and refers to a coating covering a target area. The size of a "layer" is not limited, and the dimensions of individual "layers" can be the same as or different from each other. According to one exemplary embodiment, the size of a "layer" can be the same as the size of the entire device, can correspond to the size of a specific functional area, and can also be as small as a single subpixel.

[0080] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. While similar or equivalent methods and materials to those described herein may be used in practice or in testing of exemplary embodiments of the invention, suitable methods and materials will be described below. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, unless a specific paragraph is cited, the present invention (including definitions) shall prevail. Furthermore, materials, methods, and examples are exemplary only and are not intended to be restrictive.

[0081] In this invention, the term "combination thereof" included in the Markush-type expression means a mixture or combination of one or more of the constituent elements described in the Markush-type expression, and means including one or more of the constituent elements described above.

[0082] Examples of substituents in this invention will be described below, but are not limited thereto.

[0083] In this invention, “------” and Each refers to the part to be connected.

[0084] In this invention, the term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is replaced by another substituent, and there is no limitation on the position of substitution, as long as the position is where the hydrogen atom is substituted (i.e., the position where the substituent can be substituted), and when two or more substituents are substituted, the two or more substituents can be the same as or different from each other.

[0085] In this invention, the term "substituted or unsubstituted" means substituted with one or more substituents selected from: hydrogen; deuterium; halogen group; amino group; alkyl group; aryl group; and heteroaryl group, substituted with two or more substituents linked together by the exemplified substituents, or without substituents.

[0086] In this 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 become substituents.

[0087] In this invention, the fact that three substituents are linked to each other can include not only the case where (substituent 1)-(substituent 2)-(substituent 3) are sequentially linked to each other, but also the case where (substituent 2) and (substituent 3) are linked to (substituent 1). For example, two phenyl groups and an isopropyl group can be linked to each other to become substituents. This also applies to cases where four or more substituents are connected to each other.

[0088] In this invention, the halogen group is a fluorine group (-F), a chlorine group (-Cl), a bromine group (-Br), or an iodine group (-I).

[0089] In this invention, the alkyl group can be straight-chain or branched, and its number of carbon atoms is not particularly limited, but is preferably 1 to 30, 1 to 20, 1 to 10, or 1 to 5. Specific examples include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, 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, etc. Alkyl groups may include haloalkyl groups, wherein the haloalkyl group is an alkyl group substituted with a halogen group. Specific examples include, but are not limited to, methyl groups that have been substituted with three fluorine groups, such as trifluoromethyl groups.

[0090] In this specification, there is no particular limitation on cycloalkyl groups, but they are preferably composed of 3 to 30 carbon atoms, and specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc.

[0091] In this invention, aryl refers to a monovalent aromatic hydrocarbon or a monovalent group of an aromatic hydrocarbon derivative. In this invention, aromatic hydrocarbon refers to a compound in which π electrons are fully conjugated and a planar ring is included, and a group derived from an aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or cyclic aliphatic hydrocarbon is fused with an aromatic hydrocarbon. Furthermore, in this invention, aryl is intended to include a monovalent group in which two or more aromatic hydrocarbons or aromatic hydrocarbon derivatives are linked to each other. There are no particular limitations on the aryl group, but it is preferred to have 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 monocyclic or polycyclic aryl.

[0092] There are no particular restrictions on the monocyclic aryl group, but it is preferred to have 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 phenyl, biphenyl, terphenyl, etc., but is not limited thereto.

[0093] The polycyclic aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, 6 to 45 carbon atoms, 6 to 30 carbon atoms, 6 to 22 carbon atoms, 6 to 20 carbon atoms, 6 to 18 carbon atoms, 6 to 16 carbon atoms, 6 to 15 carbon atoms, 6 to 14 carbon atoms, 6 to 13 carbon atoms, 6 to 12 carbon atoms, or 6 to 10 carbon atoms, and can be naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, triphenylene, etc. It includes, but is not limited to, methyl, fluorene, etc.

[0094] In this invention, the aryl group can include a haloaryl group substituted with a halogen group. A haloaryl group means an aryl group substituted with one or more halogen groups, and a haloaryl group can be an aryl group substituted with one or more substituents selected from fluorine, chloro, bromine, and iodo groups. Furthermore, a haloaryl group can be substituted with two or more identical halogen groups, and can be, for example, not only an aryl group substituted with one fluorine group, but also an aryl group substituted with two or more fluorine groups.

[0095] In this invention, heteroaryl refers to a monovalent aromatic heterocycle. Here, an aromatic heterocycle is a monovalent group of an aromatic ring or a derivative of an aromatic ring, and is defined as a group containing one or more of N, O, P, S, Si, and Se as heteroatoms. Derivatives of aromatic rings all contain a structure in which an aromatic ring or aliphatic ring is fused with an aromatic ring. Furthermore, in this specification, heteroaryl is intended to include a monovalent group in which two or more aromatic rings containing heteroatoms or derivatives of two or more aromatic rings containing heteroatoms are linked together. The number of carbon atoms in a 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 thiophene, furanyl, pyrrole, imidazolyl, thiazolyl, etc. Azolyl, pyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophene, dibenzothiophene, benzofuranyl, phenanthrolinel, dibenzofuranyl, etc., but not limited to these.

[0096] In this invention, the heteroaryl group can be monocyclic or polycyclic, and can be an aromatic ring, an aliphatic ring, or a fused ring of an aromatic ring and an aliphatic ring.

[0097] In this invention, the heterocyclic group is a monovalent group of an aliphatic ring, a derivative of an aliphatic ring, an aromatic ring, or a derivative of an aromatic ring, and means a group that contains one or more of N, O, P, S, Si, and Se as heteroatoms.

[0098] In this invention, the aliphatic ring is not an aromatic ring but a hydrocarbon ring, and examples of such rings include the above-mentioned examples of cycloalkyl groups, adamantyl groups, etc.

[0099] In this invention, the above-mentioned content regarding aryl groups can be applied to aromatic rings.

[0100] In this invention, the hydrocarbon ring can be an aromatic ring, an aliphatic ring, or a fused ring of an aromatic ring and an aliphatic ring. Examples of fused rings of aromatic rings and aliphatic rings include 1,2,3,4-tetrahydronaphthyl, 2,3-dihydro-1H-indenyl, etc., but are not limited thereto.

[0101] In this invention, the description of heterocyclic groups can be applied to divalent heterocycles, except that the heterocycle is a divalent group.

[0102] In this invention, "adjacent" groups can refer to substituents that substitute for an atom directly bonded to the atom substituted by the corresponding substituent, substituents that are spatially closest to the corresponding substituent, or other substituents that substitute for the atom substituted by the corresponding substituent. For example, two substituents that substitute at the ortho position on a benzene ring and two substituents that substitute for the same carbon atom in an aliphatic ring can be interpreted as "adjacent" groups.

[0103] In this invention, the curable group can undergo polymerization or crosslinking reactions, thereby enabling reactions that increase molecular weight. Examples of curable groups include thermosetting groups that cure by heat and photocurable groups that cure by light. The curable group is selected from any of the following structures, but is not limited to them.

[0104]

[0105] In the structure,

[0106] Lc1 is a direct bond; -O-; -S-; substituted or unsubstituted alkylene; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0107] lc is 1 or 2.

[0108] When lc is 2, Lc1 can be the same or different from each other.

[0109] Rc1 is a substituted or unsubstituted alkyl group, and

[0110] This refers to the portion that is bonded to chemical formula 1.

[0111] According to an exemplary embodiment of the present invention, Lc1 is a direct bond; methylene; or ethylene.

[0112] According to another exemplary embodiment of the present invention, Lc1 is a direct key.

[0113] According to an exemplary embodiment of the present invention, Rc1 is methyl; or ethyl.

[0114] According to another exemplary embodiment of the present invention, Rc1 is methyl.

[0115] The compounds represented by chemical formula 1 will be described in detail below.

[0116] According to an exemplary embodiment of the present invention, chemical formula 1 is represented by the following chemical formula 11.

[0117] [Chemical Formula 11]

[0118]

[0119] In chemical formula 11,

[0120] The definitions of L1 to L3, L11, L12, X1, X2, R1 to R4, Y, Cy1, Cy2, a, b, c, n1 to n4, m1 and m2 are the same as those in Formula 1.

[0121] According to an exemplary embodiment of the invention, L1 to L3 may be the same as or different from each other, and each is independently a direct bond; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0122] According to another exemplary embodiment, L1 to L3 may be the same as or different from each other, and each is independently a direct bond; a substituted or unsubstituted phenylene; or a substituted or unsubstituted naphthylene.

[0123] According to yet another exemplary implementation, L1 and L2 are each direct keys.

[0124] According to yet another exemplary embodiment, L3 is a direct bond; a substituted or unsubstituted phenylene; or a substituted or unsubstituted naphthylene.

[0125] According to an exemplary embodiment of the present invention, chemical formula 1 is represented by any one of the following chemical formulas 12 to 14.

[0126] [Chemical Formula 12]

[0127]

[0128] [Chemical Formula 13]

[0129]

[0130] [Chemical Formula 14]

[0131]

[0132] In chemical formulas 12 to 14,

[0133] The definitions of L11, L12, X1, X2, R1 to R4, Cy1, Cy2, Y, n1 to n4, m1, and m2 are the same as those in Formula 1.

[0134] R21 and R22 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0135] m21 is an integer from 0 to 4, m22 is an integer from 0 to 6, and when m21 and m22 are each an integer of 2 or greater, the two or more substituents in parentheses are the same or different from each other.

[0136] According to an exemplary embodiment of the present invention, Y is O, S, CRaRb or SiRcRd.

[0137] According to an exemplary embodiment of the invention, Ra, Rb, Rc and Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, or bonded to an adjacent group to form a substituted or unsubstituted ring.

[0138] According to another exemplary embodiment, Ra, Rb, Rc, and Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or bonded to an adjacent group to form a substituted or unsubstituted ring having 3 to 30 carbon atoms.

[0139] According to yet another exemplary embodiment, Ra, Rb, Rc, and Rd may be the same as or different from each other, and each is independently a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

[0140] According to an exemplary embodiment of the present invention, Cy1 and Cy2 may be the same as or different from each other, and each is independently a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring.

[0141] In one exemplary embodiment of the invention, Cy1 and Cy2 may be the same as or different from each other, and each independently constitutes any of the following structures.

[0142]

[0143] In the structure,

[0144] R11 to R13 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0145] m11 is an integer from 0 to 4, m12 and m13 are each integers from 0 to 6, and when m11 to m13 are each an integer of 2 or greater, the two or more substituents in parentheses are the same or different from each other, and

[0146] In the structure, ------ indicates the location where bonding will take place.

[0147] According to an exemplary embodiment of the invention, R11 to R13 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0148] In another exemplary embodiment, R11 to R13 are each hydrogen.

[0149] According to an exemplary embodiment of the present invention, m11 to m13 are each 0 or 1.

[0150] According to an exemplary embodiment of the invention, R1 and R2 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0151] In yet another exemplary embodiment, R1 and R2 are each hydrogen.

[0152] According to an exemplary embodiment of the invention, R3 and R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0153] In yet another exemplary embodiment, R3 and R4 may be the same as or different from each other, and each is independently hydrogen; an alkyl group having 1 to 20 carbon atoms; or an aryl group having 6 to 30 carbon atoms.

[0154] According to another exemplary embodiment, R3 and R4 may be the same as or different from each other, and each is independently hydrogen; a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

[0155] According to yet another exemplary embodiment, R3 and R4 may be the same as or different from each other, and each is independently hydrogen; methyl; or phenyl.

[0156] According to an exemplary embodiment of the present invention, n1 and n2 are each 0 or 1.

[0157] In one exemplary embodiment of the invention, R21 and R22 may be the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0158] According to another exemplary embodiment, R21 and R22 are each hydrogen.

[0159] According to an exemplary embodiment of the present invention, chemical formula 1 may be represented by any of the following compounds.

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] For a compound of formula 1 according to an exemplary embodiment of the present invention, the core structure can be prepared according to reaction scheme 1 below. Furthermore, the substituents can be bonded by methods known in the art, and the type and position of the substituents or the number of substituents can be changed according to techniques known in the art.

[0174] <Reaction Scheme 1>

[0175]

[0176] Preferably, the reaction is carried out as an amine substitution reaction in the presence of a palladium catalyst and a base, and the reactor used for the amine substitution reaction can be modified as is known in the art.

[0177] The solvent represented by chemical formula A will be described in detail below.

[0178] According to an exemplary embodiment of the invention, Y1 to Y10 may be the same as or different from each other, and each is 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.

[0179] According to an exemplary embodiment of the invention, Y1 to Y10 may be the same as or different from each other, and each is 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 amino.

[0180] According to an exemplary embodiment of the invention, Y1 to Y10 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted alkoxy.

[0181] According to an exemplary embodiment of the invention, Y1 to Y10 may be the same as or different from each other, and each is 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.

[0182] According to an exemplary embodiment of the invention, Y1 to Y10 may be the same as or different from each other, and each is 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.

[0183] According to an exemplary embodiment of the invention, Y1 to Y10 may be the same as or different from each other, and each is 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.

[0184] According to an exemplary embodiment of the invention, Y1 to Y10 may be the same as or different from each other, and each is independently hydrogen; deuterium; alkyl; or alkoxy.

[0185] According to an exemplary embodiment of the invention, Y1 to Y10 may be the same as or different from each other, and each is 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.

[0186] According to an exemplary embodiment of the present invention, Y1 to Y10 may be the same as or different from each other, and each independently is hydrogen; deuterium; methyl; ethyl; propyl; butyl; pentyl; hexyl; isopropyl; isobutyl; tert-butyl; methoxy; ethoxy; propoxy; or butoxy.

[0187] According to an exemplary embodiment of the present invention, Y1 to Y10 may be the same as or different from each other, and each is independently hydrogen; deuterium; ethyl; propyl; butyl; pentyl; isopropyl; or methoxy.

[0188] In one exemplary embodiment of the present invention, the solvent represented by chemical formula A is any of the following structures.

[0189]

[0190] In the structure, Y1 to Y10 may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

[0191] According to a preferred exemplary embodiment of the present invention, the solvent represented by chemical formula A is a mixture of any one or more of the following compounds.

[0192]

[0193] According to a preferred exemplary embodiment of the present invention, the solvent represented by chemical formula A is selected from any of the compounds.

[0194] According to an exemplary embodiment of the present invention, the solvent represented by chemical formula A is a solution selected from any one or a mixture of two or more of 3-isopropylbiphenyl, 3-methoxybiphenyl, 3-ethylbiphenyl, 4-butylbiphenyl and 4-pentylbiphenyl.

[0195] According to an exemplary embodiment of the present invention, the surface tension of the solvent represented by chemical formula A is 33 mN / m to 37 mN / m; or 33.5 mN / m to 36.5 mN / m.

[0196] Since the surface tension of the solvent represented by chemical formula A according to an exemplary embodiment of the invention is limited, the range of surface tension between materials other than the solvent represented by chemical formula A can be easily adjusted. Specifically, the materials contained in the ink composition for solution processing (e.g., additional solvents, other organic solvents, etc.) generally need to be composed of materials such that the surface tension of the ink composition is in the range of 25 mN / m to 45 mN / m, and furthermore, it is preferred that the surface tension difference between the materials is small. Surface tension in the range of 33 mN / m to 37 mN / m is close to the median of the preferred surface tension range, and therefore, when the surface tension of the solvent represented by chemical formula A is in the range of 33 mN / m to 37 mN / m, the surface tension difference between materials other than the solvent represented by chemical formula A can be adjusted to be small. When the surface tension difference between materials other than the solvent represented by chemical formula A is small, organic light-emitting devices manufactured by solution processing have the advantage of excellent flatness of the organic material layer and uniformity of pixel thickness.

[0197] According to an exemplary embodiment of the present invention, the solvent represented by chemical formula A has a boiling point of 220°C to 350°C; 250°C to 330°C; or 265°C to 315°C.

[0198] Because it contains a solvent represented by chemical formula A with a boiling point within the above range, it is expected that when the organic material layer of an organic light-emitting device is manufactured by solution processing, the flatness of the organic material layer and / or the thickness uniformity of the pixels will be excellent. Specifically, since the solvent represented by chemical formula A has the lowest vapor pressure among the constituent solvents, and therefore is not removed during the initial drying step, it has the advantage that the surface tension difference between the remaining materials can be adjusted even after the initial drying step. Therefore, the flatness of the organic material layer and / or the thickness uniformity of the pixels in the organic light-emitting device are excellent.

[0199] The ink composition according to an exemplary embodiment of the present invention further comprises an ionic compound containing an anionic group represented by the following chemical formula 2.

[0200] The following text will specifically describe ionic compounds containing anionic groups represented by the following chemical formula 2.

[0201] [Chemical Formula 2]

[0202]

[0203] In chemical formula 2,

[0204] At least one of R201 to R220 is F; cyano; or a substituted or unsubstituted fluoroalkyl group.

[0205] At least one of R201 to R220 is a curable group.

[0206] The remaining R201 to R220 may be the same as or different from each other, and each independently represents hydrogen; deuterium; nitro; -C(O)R220'; -OR221; -SR222; -SO3R223; -COOR224; -OC(O)R225; -C(O)NR226R227; substituted or unsubstituted alkyl; substituted or unsubstituted fluoroalkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted alkynyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic groups, and

[0207] R220' and R221 to R227 are the same as or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0208] According to an exemplary embodiment of the present invention, the ink composition further comprises an ionic compound containing an anionic group represented by Formula 2. Hereinafter, a compound of Formula 2 may be referred to as an anionic compound.

[0209] Unlike an ionic compound (hereinafter referred to as an anionic compound) containing an anionic group represented by Formula 2 in which a curable group is introduced according to an exemplary embodiment of the present invention, an ionic compound does not cure when a curable group is not introduced, and therefore the characteristics of the device are reduced due to the migration of the ionic compound between electrodes or layers. Furthermore, as 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.

[0210] In one exemplary embodiment of the present invention, the number of curable groups in the anionic compound represented by chemical formula 2 is one.

[0211] In one exemplary embodiment of the present invention, the number of curable groups in the anionic compound represented by chemical formula 2 is 2.

[0212] In one exemplary embodiment of the present invention, the number of curable groups in the anionic compound represented by chemical formula 2 is four.

[0213] In one exemplary embodiment of the invention, the number of F, cyano, or substituted or unsubstituted fluoroalkyl groups in the anionic group compound represented by Formula 2 is 16 to 19.

[0214] In one exemplary embodiment of the present invention, based on 100 parts by weight of anionic group compound, the part by weight of F in the anionic group compound is 15 to 50 parts by weight.

[0215] In one exemplary embodiment of the present invention, based on 100 parts by weight of anionic group compound, the parts by weight of F in the anionic group compound are 10 to 45 parts by weight.

[0216] In one exemplary embodiment of the present invention, based on 100 parts by weight of anionic group compound, the number of F in the anionic group compound is 8 to 20.

[0217] As mentioned above, the film retention rate during heat treatment is improved when the ratio of F, cyano, or fluoroalkyl groups in the molecule increases.

[0218] According to an exemplary embodiment of the present invention, an ionic compound can be used in the hole injection layer of an organic light-emitting device, and when used in the hole injection layer, it can be used as a dopant. In this case, when the content of F in the ionic compound increases, the force attracting electrons from the other compound (the host compound) increases, and holes are generated more effectively in the host, thereby improving the performance of the hole injection layer.

[0219] According to an exemplary embodiment of the present invention, the content of F can be analyzed using a COSA AQF-100 combustion furnace connected to a Dionex ICS 2000 ion chromatograph, or it can be determined by 19F NMR (which is a method commonly used for F analysis).

[0220] In one exemplary embodiment of the present invention, at least one benzene ring in Formula 2, comprising benzene rings comprising R201 to R205, benzene rings comprising R206 to R210, benzene rings comprising R211 to R215, and benzene rings comprising R216 to R220, is selected from the following structural formulas.

[0221]

[0222] According to an exemplary embodiment of the present invention, chemical formula 2 is selected from any of the following compounds.

[0223]

[0224]

[0225]

[0226] In compounds,

[0227] n is an integer from 1 to 3, m is an integer from 1 to 3, and m + n = 4.

[0228] q is an integer from 0 to 3, r is an integer from 1 to 4, and q + r = 4.

[0229] Z represents deuterium; halogen group; nitro group; cyano group; amino group; -C(O)R220'; -OR221; -SR222; -SO3R223; -COOR224; -OC(O)R225; -C(O)NR226R227; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted amino group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group.

[0230] l is an integer from 1 to 4, and when l is 2 or greater, Z are either the same or different from each other.

[0231] R220' and R221 to R227 are the same as or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0232] The following text will describe ionic compounds containing cationic groups in detail.

[0233] According to an exemplary embodiment of the present invention, the ink composition further comprises a cationic group. Specifically, the ink composition further comprises an ionic compound containing an anionic group and a cationic group represented by the above chemical formula 2. As another example, the ink composition comprises an ionic compound, and the ionic compound contains an anionic group and a cationic group represented by the above chemical formula 2.

[0234] According to an exemplary embodiment of the present invention, the cationic group is a monovalent cationic group; Compound; or selected from any of the following structural formulas.

[0235]

[0236] In the structural formula,

[0237] X1 to X 76 They may be the same as or different from each other, and each independently is hydrogen; deuterium; cyano; nitro; halogen group; -COOR224; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted cycloalkyl; substituted or unsubstituted fluoroalkyl; substituted or unsubstituted aryl; or curable group.

[0238] R224 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0239] p is an integer from 0 to 10, and

[0240] a1 is 1 or 2, b1 is 0 or 1, and a1 + b1 = 2.

[0241] According to an exemplary embodiment of the present invention, the monovalent cation group can be an alkali metal cation, and examples of alkali metal cations include Na. + Li + K + And so on, but not limited to these.

[0242] According to an exemplary embodiment of the present invention, the cationic group is Compounds; or selected from any of the above structural formulas.

[0243] According to an exemplary embodiment of the invention, the cationic group is represented by any one of the following chemical formulas 310 to 315.

[0244] [Chemical Formula 310]

[0245]

[0246] [Chemical Formula 311]

[0247]

[0248] [Chemical Formula 312]

[0249]

[0250] [Chemical Formula 313]

[0251]

[0252] [Chemical Formula 314]

[0253]

[0254] [Chemical Formula 315]

[0255]

[0256] In chemical formulas 310 to 315,

[0257] X 100 To X 142 The same or different from each other, and each independently being hydrogen; deuterium; cyano; nitro; halogen group; -COOR224; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted cycloalkyl; substituted or unsubstituted fluoroalkyl; substituted or unsubstituted aryl; or curable group, and

[0258] R224 is a substituted or unsubstituted alkyl group.

[0259] According to an exemplary embodiment of the present invention, the cationic group is selected from any of the following structural formulas.

[0260]

[0261]

[0262]

[0263] According to an exemplary embodiment of the present invention, the ionic compound is selected from any of the following chemical formulas.

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270] The ink composition will be described in detail below.

[0271] An exemplary embodiment of the present invention provides an ink composition comprising the compound represented by Chemical Formula 1 and the solvent represented by Chemical Formula A.

[0272] According to an exemplary embodiment of the present invention, the ink composition further comprises an ionic compound containing an anionic group represented by the above-described chemical formula 2.

[0273] According to an exemplary embodiment of the present invention, the ionic compound further comprises the aforementioned cationic group compound. That is, the ink composition further comprises an ionic compound containing an anionic group represented by the aforementioned chemical formula 2 and the aforementioned cationic group.

[0274] According to a preferred exemplary embodiment of the present invention, the ink composition further comprises one or more additional solvents selected from the following: tetrahydronaphthalene, 4-methoxytoluene, tetrahydrofuran, dichloro ... tetrahydrotoluene, tetrahydrofuran, dichlorona Alkane, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, solvents represented by the following chemical formula C-1 and solvents represented by the following chemical formula C-2.

[0275] [Chemical formula C-1]

[0276]

[0277] [Chemical formula C-2]

[0278]

[0279] In chemical formulas C-1 and C-2,

[0280] L100 and L101 may be the same as or different from each other, and each is independently a direct bond; or substituted or unsubstituted alkylene groups.

[0281] G1 and G3 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0282] G2 is a straight-chain alkyl group.

[0283] G4 is a substituted or unsubstituted alkyl group, and

[0284] g1 and g3 are each integers from 1 to 5, and when g1 and g3 are each 2 or greater, the two or more substituents in parentheses are the same or different from each other.

[0285] According to an exemplary embodiment of this specification, the additional solvent is selected from one or more of the following: tetrahydronaphthalene, 4-methoxytoluene, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, solvents represented by chemical formula C-1, and solvents represented by chemical formula C-2.

[0286] According to an exemplary embodiment of the present invention, the viscosity of the additional solvent is 1 cP to 15 cP.

[0287] Because it contains additional solvents with viscosities in the above range, it has the advantage that ink compositions with viscosities suitable for inkjet printing can be prepared.

[0288] According to an exemplary embodiment of the present invention, the boiling point of the additional solvent is lower than that of the solvent represented by chemical formula A.

[0289] According to an exemplary embodiment of the present invention, the boiling point of the additional solvent is 70°C to 280°C; 100°C to 280°C; 180°C to 280°C; 180°C to 265°C; or 190°C to 250°C.

[0290] Because it contains additional solvents with boiling points in the above range, it has the advantage that ink compositions with drying rates suitable for inkjet printing can be prepared.

[0291] According to an exemplary embodiment of the present invention, the solvent represented by the chemical formula C-1 is selected from any of the following structures.

[0292]

[0293] According to an exemplary embodiment of the present invention, the solvent represented by the chemical formula C-2 is benzyl butyrate.

[0294] According to an exemplary embodiment of the present invention, one or both of the solvents described above are used as an additional solvent.

[0295] According to an exemplary embodiment of the present invention, the ink composition comprises a first additional solvent selected from: tetrahydronaphthalene, 4-methoxytoluene, tetrahydrofuran, dichlorodiphenyl ether ... Alkane, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, solvents represented by chemical formula C-1 and solvents represented by chemical formula C-2.

[0296] According to an exemplary embodiment of the present invention, the ink composition comprises a first additional solvent selected from the following and a second additional solvent: tetrahydronaphthalene, 4-methoxytoluene, tetrahydrofuran, dichloro ... tetrahydrotoluene, tetrahydrofuran, dichloro Alkane, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, solvents represented by chemical formula C-1 and solvents represented by chemical formula C-2, wherein the first additional solvent and the second additional solvent are different from each other.

[0297] According to an exemplary embodiment of the invention, the ink composition comprises a first additional solvent selected from the following: a solvent represented by chemical formula C-1 and a solvent represented by chemical formula C-2.

[0298] According to an exemplary embodiment of the present invention, the ink composition comprises a second additional solvent selected from the following: tetrahydronaphthalene, 4-methoxytoluene, tetrahydrofuran, dichloro ... tetrahydrotoluene, tetrahydrofuran, dichloronaphthalene, tetra Alkane, dipropylene glycol monomethyl ether and tripropylene glycol monomethyl ether.

[0299] An exemplary embodiment of the present invention provides an ink composition comprising: a compound represented by chemical formula 1 above; a solvent represented by chemical formula A above; an ionic compound containing an anionic group represented by chemical formula 2 above; and the additional solvent mentioned above.

[0300] An exemplary embodiment of the present invention provides an ink composition comprising: a compound represented by the above chemical formula 1; a solvent represented by the above chemical formula A; the above ionic compound; and the above additional solvent, wherein the ionic compound contains an anionic group represented by the above chemical formula 2 and the above cationic group.

[0301] According to an exemplary embodiment of the invention, based on 100% by weight of the ink composition, the compound represented by chemical formula 1 is included in an amount of 0.1% to 15% by weight, 0.1% to 10% by weight, or 0.1% to 5% by weight.

[0302] According to an exemplary embodiment of the invention, based on 100% by weight of ink composition, a solvent represented by chemical formula A is included in an amount of 1% to 70% by weight, 1% to 50% by weight, or 1% to 30% by weight.

[0303] According to an exemplary embodiment of the present invention, based on 100% by weight of the ink composition, an ionic compound containing an anionic group represented by chemical formula 2 is included in an amount of 0.1% to 15% by weight, 0.1% to 10% by weight, or 0.1% to 5% by weight.

[0304] According to an exemplary embodiment of the invention, based on 100% by weight of the ink composition, additional solvent is included in amounts of 10% to 90% by weight, 10% to 85% by weight, 10% to 80% by weight, or 10% to 70% by weight. However, the amounts are not limited to the above examples, and amounts commonly used by those skilled in the art to which this invention pertains can be used as the content of additional solvent.

[0305] According to an exemplary embodiment of the present invention, based on 100% by weight of the ink composition, a compound represented by chemical formula 1 is included in an amount of 0.1% by weight to 15% by weight; a solvent represented by chemical formula A is included in an amount of 1% by weight to 70% by weight; an ionic compound containing an anionic group represented by chemical formula 2 is included in an amount of 0.1% by weight to 15% by weight; and an additional solvent is included in an amount of 10% by weight to 85% by weight.

[0306] According to an exemplary embodiment of the present invention, the ink composition has a viscosity of 2 cP to 15 cP at room temperature. When this viscosity is met, it facilitates device fabrication. Specifically, when forming the organic material layer in an organic light-emitting device, a uniform film can be formed.

[0307] The above viscosities are measured at room temperature using a viscometer manufactured by Brookfield Engineering Labs Inc., after the object to be measured is dissolved in a solvent at a concentration of 1% to 3% by weight. In this case, the object to be measured is a compound represented by Chemical Formula 1; or a mixture of a compound represented by Chemical Formula 1 and the aforementioned ionic compound. Furthermore, the solvent is a solvent represented by Chemical Formula A; or a mixture of a solvent represented by Chemical Formula A and another solvent.

[0308] According to an exemplary embodiment of the present invention, the ink composition is a liquid phase. "Liquid phase" means that the composition is liquid at room temperature under atmospheric pressure.

[0309] In one exemplary embodiment of this specification, the ink composition can be cured by heat treatment or light treatment. When the ink composition is cured, this can be referred to as a cured product of the ink composition.

[0310] According to an exemplary embodiment of the present invention, the ink composition further comprises: a monomolecule containing photocurable groups and / or thermosetting groups, or a monomolecule containing end groups capable of forming a polymer by heat. As described above, the monomolecule containing photocurable groups and / or thermosetting groups, or the monomolecule containing end groups capable of forming a polymer by heat, can be a compound with a molecular weight of 3,000 g / mol or less, but the molecular weight is not limited to the exemplified molecular weight.

[0311] Monomolecules containing photocurable and / or thermosetting groups, or monomolecules containing end groups capable of forming polymers by heat, may refer to aryl groups, such as phenyl, biphenyl, fluorene, and naphthalene; arylamines; or monomolecules wherein fluorene is substituted by photocurable and / or thermosetting groups or end groups capable of forming polymers by heat.

[0312] According to an exemplary embodiment of the present invention, in addition to the other solvents described above, the ink composition may further contain a third solvent (hereinafter referred to as a third solvent). The third solvent may be selected from one or more of the following: chlorine-based solvents, such as chloroform, dichloromethane, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether-based solvents, such as tetrahydrofuran, dichloromethane, dichlorobenzene ... Alkanes and dipropylene glycol monomethyl ethers; solvents based on aromatic hydrocarbons, such as toluene, xylene, trimethylbenzene, and mesitylene; solvents based on aliphatic hydrocarbons, such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; solvents based on ketones, such as acetone, methyl ethyl ketone, cyclohexanone, isophorone, tetrahydronaphthone, naphthyl ketone, and acetylacetone; solvents based on esters, such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, and benzyl butyrate. Polyols, such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerol, and 1,2-hexanediol, and their derivatives; alcohol-based solvents, such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide-based solvents, such as dimethyl sulfoxide; amide-based solvents, such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; and tetrahydronaphthalene. However, the third solvent is not limited to the examples above, and it is sufficient if the third solvent can dissolve or disperse the compound represented by the above chemical formula 1.

[0313] According to an exemplary embodiment of the present invention, the ink composition is a composition for forming one or more layers selected from hole injection layer, hole transport layer, hole injection and transport layer, and electron blocking layer.

[0314] The following text will specifically describe pixels containing the above-described ink composition or its cured product.

[0315] An exemplary embodiment of the present invention provides a pixel comprising an ink composition or a cured product thereof. The pixel may be contained in an organic material layer, an organic light-emitting diode (OLED), or an organic light-emitting display device. Details of the organic material layer will be described below. Specifically, the organic light-emitting display device comprises a plurality of pixels consisting of red (R) sub-pixels, green (G) sub-pixels, and blue (B) sub-pixels, and an organic light-emitting diode (OLED) and pixel circuitry are positioned for each sub-pixel. The OLED includes two electrodes (anode and cathode) and an organic light-emitting layer positioned therebetween, and the pixel circuitry includes at least two thin-film transistors and at least one capacitor. The organic material layer, OLED, or organic light-emitting display device may include a dike. Preferably, the organic material layer, OLED, or organic light-emitting display device may include a linear dike. The linear dike may define a linear pixel region and / or a sub-pixel region. Normally, 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 the red, green, and blue sub-pixels. In this case, the aforementioned pixel may correspond to a pixel or a sub-pixel. As a preferred exemplary embodiment, a pixel corresponds to a sub-pixel.

[0316] According to an exemplary embodiment of the present invention, the above-mentioned organic material layer, organic light-emitting diode or organic light-emitting display device may include one or more pixels.

[0317] According to an exemplary embodiment of the present invention, the thickness uniformity V of one or more pixels is 0.4 or less, and the thickness uniformity V satisfies the following equation 1.

[0318] According to an exemplary embodiment of the present invention, the thickness uniformity V satisfies the following equation 1.

[0319] [Equation 1]

[0320]

[0321] In equation 1,

[0322] X(i) is the thickness of the i-th pixel.

[0323] Xm' is the average value of X(i) where i is from 2 to n', and

[0324] n' is 2 to 10 4 Integers.

[0325] In this invention, when the thickness uniformity V is 0.4 or less and the thickness uniformity V satisfies Equation 1, it means that the thickness uniformity V calculated using Equation 1 is 0.4 or less.

[0326] According to an exemplary embodiment of the present invention, the thickness uniformity is 0.01 to 0.4, or 0.02 to 0.4.

[0327] In this invention, a low thickness uniformity value means that the thickness of the pixel is uniformly formed. That is, the lower the thickness uniformity value, the more uniform the pixel formation.

[0328] According to an exemplary embodiment of the present invention, the thickness of a pixel may refer to the thickness of the central portion of the pixel, and can be measured by an optical thickness measuring device. As an optical thickness measuring device, an optical profilometer manufactured by Bruker, etc., can be used, but the optical thickness measuring device is not limited thereto.

[0329] An exemplary embodiment of the present invention provides an organic material layer comprising the aforementioned pixels. Specifically, an exemplary embodiment of the present invention provides an organic material layer comprising the aforementioned ink composition or its cured product.

[0330] The organic material layer containing the aforementioned pixels will be described in detail below.

[0331] According to an exemplary embodiment of the present invention, the organic material layer comprises a plurality of pixels. For example, the organic material layer comprises 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, wherein na and nb are each 2 to 10. 4 Integers.

[0332] According to an exemplary embodiment of the present invention, na and nb are each 2 or greater, 5 or greater, 10 or greater, 20 or greater, or 40 or greater, 10 4 or smaller, 10 3 Or smaller, or 10 2 Or smaller.

[0333] According to 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 One or fewer, 10 6 One or fewer, 10 4 One or fewer, or 10 3 One or fewer pixels.

[0334] According to an exemplary embodiment of the present invention, the pixels contained in the organic material layer are arranged in a linear manner. For example, as... Figure 2 As shown, multiple pixels are arranged in rows to form a line.

[0335] According to 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. For example, such as Figure 2 As shown, multiple lines can be formed at regular intervals. For example, the y-axis with the aforementioned nb pixels can be a single line, and it can contain as many lines as the number of pixels (na) contained in the x-axis.

[0336] According to an exemplary embodiment of the present invention, the organic material layer comprises na×nb pixels.

[0337] According to an exemplary embodiment of the present invention, a plurality of pixels contained in an organic material layer have a uniform thickness.

[0338] According to an exemplary embodiment of the present invention, the organic material layer comprises n' pixels, the thickness uniformity V of the n' pixels is 0.4 or less, and the thickness uniformity V satisfies Equation 1 above.

[0339] According to an exemplary embodiment of the present invention, n' is 2 to 10. 4 .

[0340] According to an exemplary embodiment of the present invention, an organic material layer is included in an organic light-emitting device.

[0341] According to an exemplary embodiment of the present invention, the organic material layer is formed by a solution method.

[0342] According to an exemplary embodiment of the present invention, the organic material layer is selected from one or more layers selected from hole injection layer, hole transport layer, hole injection and transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron injection layer, electron transport layer and electron injection and transport layer.

[0343] According to an exemplary embodiment of the present invention, the organic material layer is one or more layers selected from hole injection layer, hole transport layer, hole injection and transport layer, electron blocking layer and light emitting layer.

[0344] According to an exemplary embodiment of the present invention, the organic material layer is one or more layers selected from hole injection layer, hole transport layer, hole injection and transport layer and electron blocking layer.

[0345] According to an exemplary embodiment of the present invention, the ink composition is a composition for forming one or more layers selected from hole injection layer, hole transport layer, hole injection and transport layer, and electron blocking layer.

[0346] According to 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.

[0347] Organic light-emitting devices will be described in detail below.

[0348] An exemplary embodiment of the present invention provides an organic light-emitting device comprising: 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 comprise the aforementioned ink composition or a cured product thereof.

[0349] According to 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 the layers selected from one or more layers include an ink composition or a cured product thereof.

[0350] According to an exemplary embodiment of the present invention, the organic material layer includes one or more layers selected from hole injection layer, hole transport layer, hole injection and transport layer, and electron blocking layer, and the one or more layers selected from hole injection layer, hole transport layer, hole injection and transport layer, and electron blocking layer contain ink composition or cured product thereof.

[0351] According to a preferred 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, hole transport layer, or electron blocking layer contains an ink composition or a cured product thereof.

[0352] According to an exemplary embodiment of the present invention, the organic material layer included in the organic light-emitting device comprises n' pixels as described above, the thickness uniformity V of the n' pixels is 0.4 or less, and the thickness uniformity V satisfies Equation 1 above.

[0353] The methods used to manufacture organic light-emitting devices will be described in detail below.

[0354] An exemplary embodiment of the present invention provides a method for manufacturing an organic light-emitting device, the method comprising: preparing a first electrode;

[0355] An organic material layer having one or more layers is formed on the first electrode; and

[0356] A second electrode is formed on an organic material layer having one or more layers.

[0357] The formation of the organic material layer includes forming an organic material layer using the above-mentioned ink composition.

[0358] According to an exemplary embodiment of the present invention, the organic material layer can be formed on a substrate including a linear embankment or an organic material layer by using an ink composition to form an organic material layer.

[0359] As an example, the above ink composition is applied ( Figure 3 ) at the base including linear dikes ( Figure 2 Then a thin film in which the ink composition is dried and / or heat-treated can be formed. Figure 4 ).

[0360] According to another exemplary embodiment of the present invention, an organic material layer is formed using a spin coating method with an ink composition.

[0361] According to yet another exemplary embodiment of the present invention, an organic material layer is formed using an ink composition via printing.

[0362] According to an exemplary embodiment of the present invention, examples of printing methods include inkjet printing, nozzle printing, offset printing, transfer printing, screen printing, etc., but are not limited to the printing methods listed above.

[0363] According to an exemplary embodiment of the present invention, an organic material layer is formed using an ink composition via inkjet printing.

[0364] Due to the composition and structural characteristics of the materials contained therein, the solution method is applicable to ink compositions according to an exemplary embodiment of the present invention, such that the organic material layer can be formed by printing, and thus has economic benefits in terms of time and cost when manufacturing devices.

[0365] According to an exemplary embodiment of the present invention, forming an organic material layer on the first electrode may further include drying after one or more depressurization steps. As an example, forming an organic material layer on the first electrode may also include drying after two depressurization steps. In this case, the drying after the first depressurization is performed at atmospheric pressure to 2 × 10⁻⁶. -2 The process was carried out under pressure, and at atmospheric pressure up to 2×10⁻⁶. -2 The decompression time can range from 30 seconds to 600 seconds. Furthermore, the drying time after the second decompression is 2 × 10⁻⁶ seconds. -2 Up to 2×10 -6 The process is carried out under pressure, and in 2×10-2 Up to 2×10 -6 The decompression time under the support can range from 30 seconds to 600 seconds.

[0366] According to an exemplary embodiment of the present invention, forming an organic material layer using an ink composition includes: coating the ink composition; and subjecting the coated ink composition to heat treatment or light treatment.

[0367] According to an exemplary embodiment of the present invention, forming an organic material layer using an ink composition includes: coating a first electrode or an organic material layer having one or more layers with the ink composition; and subjecting the coated ink composition to heat treatment or light treatment.

[0368] According to an exemplary embodiment of the present invention, the heat treatment of the ink composition can be performed by heat treatment, and the heat treatment temperature during the heat treatment of the ink composition can be from 85°C to 250°C, from 100°C to 250°C according to one exemplary embodiment, and from 150°C to 250°C in another exemplary embodiment.

[0369] According to an exemplary embodiment of the present invention, the heat treatment time for heat treating the ink composition can be in the range of 10 minutes to 2 hours, in one exemplary embodiment it can be in the range of 10 minutes to 1 hour, and in another exemplary embodiment it can be in the range of 20 minutes to 1 hour.

[0370] When forming an organic material layer using an ink composition, including heat treatment or light treatment of the ink composition, the multiple compounds contained in the ink composition can form crosslinks, thereby providing an organic material layer comprising a thin film structure. In this case, when additional layers are stacked on the surface of the organic material layer formed using the ink composition, it is possible to prevent the organic material layer from dissolving, being morphologically affected, or decomposing due to solvents.

[0371] Therefore, when the organic material layer formed using the ink composition is formed by methods including heat treatment or light treatment of the organic material layer, the solvent resistance is improved, allowing multiple layers to be formed by repeated solution deposition and cross-linking, and the stability is improved, thereby improving the lifespan characteristics of the device.

[0372] The types of organic material layers included in the above-mentioned organic light-emitting devices will be described in detail below.

[0373] According to an exemplary embodiment of the present invention, the organic light-emitting device includes an organic material layer having one layer, and the organic material layer contains the above-described ink composition or its cured product.

[0374] According to another exemplary embodiment of the present invention, the organic light-emitting device includes an organic material layer having two or more layers, and the organic material layer having two or more layers contains the aforementioned ink composition or its cured product. For example, in an organic material layer having two or more layers, any one of the organic material layers contains the ink composition or its cured product, and further includes an organic material layer having another or more layers. An organic material layer having another or more layers according to one exemplary embodiment does not contain the ink composition or its cured product. An organic material layer having another or more layers according to another exemplary embodiment also contains the ink composition or its cured product. However, the organic material layer having another or more layers is not limited to these examples.

[0375] Organic material layers having two or more layers include two or more layers selected from the group consisting of: for example, hole injection layers, hole transport layers, hole injection and transport layers, electron blocking layers, light-emitting layers, hole blocking layers, electron transport layers, electron injection layers, electron injection and transport layers, etc. In this context, a hole injection and transport layer means a layer that simultaneously injects and transports holes, and an electron injection and transport layer means a layer that simultaneously injects and transports electrons. However, organic material layers forming the group are merely examples and are not limited to the above examples. Furthermore, if necessary, organic material layers having two or more layers may include two or more layers that serve the same function. An organic light-emitting device according to an exemplary embodiment includes a first hole injection layer and a second hole injection layer. However, organic material layers having two or more layers are not limited to these examples.

[0376] According to one exemplary embodiment of the present invention, the organic material layer includes a light-emitting layer. As an example, the light-emitting layer comprises an ink composition or a cured product thereof. As a specific example, the light-emitting layer comprises an ink composition or a cured product thereof as the body of the light-emitting layer. As another specific example, the light-emitting layer comprises an ink composition or a cured product thereof as a dopant of the light-emitting layer.

[0377] According to 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 comprises an ink composition or a cured product thereof.

[0378] According to a preferred exemplary embodiment of the present invention, the organic material layer includes a hole transport layer or an electron blocking layer. As an example, the hole transport layer or electron blocking layer comprises an ink composition or a cured product thereof.

[0379] According to a preferred exemplary embodiment of the present invention, the organic material layer includes a hole injection layer and a hole transport layer.

[0380] According to an exemplary embodiment of the present invention, the organic material layer further includes 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 the hole-blocking layer, electron transport layer, electron injection layer, and electron injection and transport layer comprise an ink composition or a cured product thereof. As another example, one or more layers selected from the hole-blocking layer, electron transport layer, electron injection layer, and electron injection and transport layer do not comprise an ink composition or a cured product thereof.

[0381] An exemplary embodiment of the present invention provides an organic light-emitting device comprising: 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 the organic material layer includes a light-emitting layer and a hole injection layer, and the hole injection layer comprises an ink composition or a cured product thereof.

[0382] The following text will describe in detail the stacked structure of the organic material layers and the organic light-emitting device including the organic material layers.

[0383] An organic material layer of an organic light-emitting device according to an exemplary embodiment of the present invention has a monolayer structure. For example, the organic material layer having a monolayer structure is disposed between a first electrode and a second electrode of the organic light-emitting device and contains an ink composition or a cured product thereof. According to a specific exemplary embodiment, the organic material layer having a monolayer structure is a light-emitting layer, and in this case, the light-emitting layer contains an ink composition or a cured product thereof.

[0384] An organic light-emitting device according to another exemplary embodiment of the present invention has an organic material layer having a multilayer structure in which two or more organic material layers are stacked. For example, the organic material layer having a multilayer structure is disposed between the first electrode and the second electrode of the organic light-emitting device.

[0385] According to an exemplary embodiment of the present invention, an organic material layer having a multilayer structure includes a light-emitting layer and organic material layers other than the light-emitting layer. As an example, the light-emitting layer is disposed between a first electrode and a second electrode, and the organic material layers other than the light-emitting layer are disposed between the first electrode and the light-emitting layer. As another example, the light-emitting layer is disposed between the first electrode and the second electrode, and the organic material layers other than the light-emitting layer are disposed between the light-emitting layer and the second electrode. As yet another example, the light-emitting layer is disposed between the first electrode and the second electrode, any organic material layer other than the light-emitting layer is disposed between the first electrode and the light-emitting layer, and other organic material layers other than the light-emitting layer are disposed between the light-emitting layer and the second electrode. However, the above structures are merely examples, and the structures are not limited to the above structures. Furthermore, the organic material layers other than the light-emitting layer can be one or more layers selected from, 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 are not limited thereto.

[0386] Typically, in organic light-emitting devices, a hole injection layer, a hole transport layer, or an electron blocking layer 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.

[0387] Furthermore, typically, the electron injection layer, electron transport layer, or hole blocking layer in an organic light-emitting device is disposed between the cathode and the light-emitting layer. As a specific example, the hole blocking layer is disposed on the light-emitting layer, the electron transport layer is disposed on the hole blocking layer, and the electron injection layer is disposed on the electron transport layer, but the present invention is not limited to the above examples.

[0388] An organic light-emitting device according to an exemplary embodiment of the present invention includes an organic material layer having a multilayer structure, comprising: one or more layers selected from hole injection and transport layer, hole injection layer, hole transport layer, electron blocking layer, hole blocking layer, electron transport layer, electron injection layer, and electron injection and transport layer; and a light-emitting layer disposed between a first electrode and a second electrode, wherein the one or more layers are disposed between the first electrode and the light-emitting layer or between the second electrode and the light-emitting layer, and the one or more layers comprise an ink composition or a cured product thereof.

[0389] Figure 1 The structure of an organic light-emitting device according to an exemplary embodiment of the present invention is shown. Figure 1 An example is shown 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. Figure 1 The hole injection layer 301 and / or hole transport layer 401 contain the above-described ink composition or its cured product, or can be formed using the ink composition. In this case, for Figure 1 The hole injection layer 301 and / or hole transport layer 401, the organic material layer that can be formed using the ink composition, its material and manufacturing method will be described below. Furthermore, Figure 1 An organic light-emitting device according to an exemplary embodiment of the present invention is illustrated, but the organic light-emitting device is not limited thereto.

[0390] As described above, organic light-emitting devices having organic material layers with single or multiple layers can have, for example, the following stacked structures, but the stacked structures are not limited to these.

[0391] (1) Anode / hole transport layer / light-emitting layer / cathode

[0392] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0393] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0394] (4) Anode / Hole transport layer / Light emission layer / Electron transport layer / Cathode

[0395] (5) Anode / Hole transport layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0396] (6) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0397] (7) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0398] (8) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0399] (9) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0400] (10) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0401] (11) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0402] (12) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0403] (13) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0404] (14) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Cathode

[0405] (15) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0406] (16) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Cathode

[0407] (17) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0408] (18) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode / Encapsulation

[0409] (19) Anode / Hole injection layer / First hole transport layer / Second hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode / Encapsulation

[0410] In the structure, the “electron transport layer / electron injection layer” can be replaced by “electron injection and transport layer” or “layer that simultaneously injects and transports electrons”.

[0411] Furthermore, in the structure, "hole injection layer / hole transport layer" can be replaced by "hole injection and transport layer" or "layer that simultaneously injects and transports holes".

[0412] According to an exemplary embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.

[0413] According to another exemplary embodiment of the present invention, the first electrode is a cathode and the second electrode is an anode.

[0414] According to an exemplary embodiment of the present invention, the organic light-emitting device can 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.

[0415] According to another exemplary embodiment of the present invention, the organic light-emitting device can 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.

[0416] The organic material layer, its materials, and its manufacturing method will be described in detail below. However, the organic light-emitting device of the present invention can be manufactured using materials and methods known in the art, the difference being that the organic material layer contains the aforementioned compound.

[0417] In an organic light-emitting device according to an exemplary embodiment of the present invention, one or more layers of organic material are formed using an ink composition or its cured product. Alternatively, the organic light-emitting device can be manufactured using materials and methods known in the art.

[0418] 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 using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation to form an anode; forming an organic material layer on the anode by a solution method, deposition method, etc., including one or more layers such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, an electron transport layer, a hole transport and injection layer, and an electron injection and transport layer; and then depositing a material that can be used as a cathode on the organic material layer. In addition to the above methods, the 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.

[0419] As an anode material, materials with high work functions are generally preferred to facilitate hole injection into the organic material layer. Examples 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-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline; and so on, but are not limited thereto.

[0420] As cathode materials, materials with low work functions are generally preferred to facilitate electron injection into the organic material layer. Examples include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al; and so on, but are not limited to these.

[0421] The light-emitting layer may contain a host material and / or a dopant material.

[0422] Examples of host materials include fused aromatic ring derivatives and heterocyclic compounds. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, and fluoranthene compounds, while specific examples of heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but are not limited to these.

[0423] Examples of dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are fused aromatic ring derivatives having substituted or unsubstituted arylamine groups, and examples include pyrene, anthracene, etc., having arylamine groups. Diindrone pyrene, etc. Furthermore, styrylamine compounds are compounds in which at least one aryl vinyl group is substituted with a substituted or unsubstituted arylamine, and one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups are substituted or unsubstituted. Specific examples include, but are not limited to, styrylamines, styryldiamines, styryltriamines, styryltetraamines, etc. Furthermore, examples of metal complexes include, but are not limited to, iridium complexes, platinum complexes, etc.

[0424] 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 excellent hole injection effect on the light-emitting layer or light-emitting material. Furthermore, the hole injection material is preferably a material that excels in preventing excitons generated by the light-emitting layer from migrating to the electron injection layer or electron injection material. Furthermore, the hole injection material is preferably a material that excels in the ability to form thin films. Furthermore, 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: metalloporphyrins, oligothiophenes, and arylamine-based organic materials; organic materials based on hexanitrile hexaazabenzophenanthrene; organic materials based on quinacridones; organic materials based on perylene; conductive polymers based on polythiophene, such as anthraquinone and polyaniline; and so on, but are not limited thereto.

[0425] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer, and may have a single-layer structure or a multilayer structure with two or more layers. The hole transport material is preferably a material with high hole mobility that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer. In this invention, compounds represented by the above-described chemical formula 1 may be included as hole transport materials. Furthermore, if necessary, other hole transport materials may be included in addition to the compounds represented by chemical formula 1. Specific examples include, but are not limited to, arylamine-based organic materials, carbazole-based compounds, conductive polymers, block copolymers having both conjugated and non-conjugated portions. According to an exemplary embodiment of the invention, the hole transport material is an ink composition or its cured product.

[0426] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is preferably a material with high electron mobility that can effectively receive electrons from the cathode and transfer them to the light-emitting layer. Specific examples include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavonoid-metal complexes; and so on, but are not limited to these. The electron transport layer can be used with any desired cathode material as used according to the relevant art. In particular, suitable cathode materials are typically materials with low work functions, followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0427] The electron injection layer is a layer that receives electrons from the electrodes. Preferably, the electron injection material is excellent in its ability to transport electrons and has the effect of receiving electrons from the cathode and excellent electron injection effect on the light-emitting layer or light-emitting material. Furthermore, the electron injection material is preferably a material that prevents excitons generated by the light-emitting layer from migrating to the hole injection layer and has excellent ability to form a thin film. Specific examples include fluorenone, anthraquinone dimethane, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenemethane, anthrones, and their derivatives; metal complex compounds; nitrogen-containing 5-membered ring derivatives; and so on, but not limited to these. Examples of metal complex compounds include lithium 8-hydroxyquinoline, 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 to these.

[0428] An electron blocking layer is a layer that improves the lifespan and efficiency of a device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. An electron blocking layer can be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes, using a compound of the aforementioned chemical formula 2.

[0429] A hole blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed under the same conditions as the electron injection layer. Specific examples of hole blocking layer materials include... Diazole or triazole derivatives, phenanthrene-rhein derivatives, aluminum complexes, etc., but not limited to these.

[0430] The hole injection and transport layer may contain materials used for the aforementioned hole injection layer and hole transport layer.

[0431] The electron injection and transport layer may contain materials for the aforementioned electron injection layer and electron transport layer.

[0432] When an organic light-emitting device comprises multiple layers of organic materials, the organic material layers can be formed from the same material or different materials.

[0433] Depending on the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a dual-emitting type.

[0434] An exemplary embodiment of the present invention provides an electronic device comprising an organic light-emitting device comprising the above-described ink composition or a cured product thereof, or comprising an organic material layer formed using the ink composition.

[0435] Electronic devices may include all of the following: interlayer insulating films, color filters, black matrices, outer coatings, columnar spacers, passivation films, buffer coatings, insulating films of multilayer printed circuit boards, cover coatings of flexible copper-clad laminates, solder resist films, insulating films of OLEDs, protective films of thin-film transistors of liquid crystal display devices, electrode protective films and semiconductor protective films of organic EL devices, OLED insulating films, LCD insulating films, semiconductor insulating films, solar photovoltaic modules, touch panels, display devices such as display panels, etc., but are not limited to these.

[0436] Invention Embodiments

[0437] In the following description, the invention will be described in detail with reference to embodiments used to specifically describe the invention. However, embodiments of the invention can be modified in various different forms and should not be construed as limiting the scope of the invention to the embodiments described below. Embodiments of the invention are provided to provide a more complete explanation of the invention to those skilled in the art.

[0438] <Examples of compound preparation>

[0439] Synthesis Example A-1. Preparation of Compound 1

[0440] (1) Preparation of intermediate 1-1

[0441]

[0442] 1-Bromo-4-fluorobenzene (27.9 mL, 255 mmol) was added to tetrahydrofuran (THF) (500 mL). After purging with nitrogen, the mixture was cooled to -78 °C. n-BuLi (2.5 M Hex) (96 mL, 240 mmol) was placed in a dropping funnel and slowly introduced into the reaction mixture. The resulting mixture was stirred at -78 °C for 30 minutes. 2-Bromofluorenone (38.9 g, 150 mmol) was added. The mixture was stirred overnight while slowly warming to room temperature. After terminating the reaction by adding distilled water, it was extracted with ethyl acetate and water. After collecting the organic layer, the organic layer was dried over MgSO4 and filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent, giving intermediate 1-1, which was used in the next reaction.

[0443] (2) Preparation of intermediate 1-2

[0444]

[0445] Intermediate 1-1 (53 g, 150 mmol) and phenol (70.6 g, 750 mmol) were placed in a round-bottom flask (RBF). After adding CH3SO3H (214 mL), the resulting mixture was stirred at 60 °C for 4 hours. After adding ice water, the mixture was extracted with ethyl acetate and water. After collecting the organic layer, the organic layer was dried over MgSO4 and filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, the mixture was crystallized under dichloromethane (DCM) / heptane conditions to give 40.6 g of intermediate 1-2.

[0446] (3) Preparation of intermediates 1-3

[0447]

[0448] Intermediates 1-2 (45 g, 104 mmol), N-phenylbis(trifluoromethanesulfonylimide) (PhNTf2) (81.8 g, 229 mmol), and 4-dimethylaminopyridine (DMAP) (2.54 g, 21 mmol) were placed in a round-bottom flask. Dichloromethane (416 mL) and triethylamine (TEA) (37.7 mL, 270 mmol) were added, and the resulting mixture was stirred at room temperature (RT) for 1 hour. Extraction was performed with dichloromethane and 3% HCl aqueous solution, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. Crystallization was carried out under dichloromethane / heptane conditions to prepare intermediate 1-3 (52.5 g).

[0449] (4) Preparation of intermediates 1-4

[0450]

[0451] Intermediates 1-3 (52.2 g, 92.7 mmol), potassium vinyltrifluoroborate (27.3 g, 204 mmol), Pd(dppf)Cl2 (3.4 g, 4.6 mmol), and K2CO3 (51.2 g, 971 mmol) were placed in a round-bottom flask. After purging with nitrogen, THF (371 mL) and H2O (93 mL) were added, and the resulting mixture was stirred at 90 °C for 4 hours. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to prepare intermediate 1-4 (34 g).

[0452] (5) Preparation of compound 1

[0453]

[0454] 4-Aminodibenzofuran (513 mg, 2.8 mmol), intermediate 1-4 (2.53 g, 5.74 mmol), Pd(PtBu3)2 (72 mg, 0.14 mmol), and NaOtBu (1.08 g, 11.2 mmol) were placed in an RBF. After purging with nitrogen, toluene (14 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to obtain 2.0 g of compound 1. The synthesis of this compound was confirmed by LC-MS and NMR. MS: [M+H]+=904

[0455]

[0456] Synthesis Example A-2. Preparation of Compound 2

[0457] (1) Preparation of intermediate 2-3

[0458]

[0459] Intermediate 1-2 (40 g, 92.7 mmol), 4-nitrobenzaldehyde (21.2 g, 139 mmol), Cu(OAc)₂ (842 mg, 4.64 mmol), and Cs₂CO₃ (45.3 g, 139 mmol) were placed in an RBF container. DMF (310 mL) was added, and the resulting mixture was stirred at 100 °C for 4 hours. Extraction was performed with ethyl acetate and water, and the organic layer was collected. The organic layer was then dried over MgSO₄ and filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was carried out under DCM / heptane conditions to give 38.7 g of intermediate 2-3.

[0460] (2) Preparation of intermediate 2-4

[0461]

[0462] After adding CH3PPh3Br (51.6 g, 144.6 mmol), KOtBu (16.2 g, 144.6 mmol), and THF (217 mL) to an RBF container, the resulting mixture was cooled to 0 °C. A solution of intermediate 2-3 (38.7 g, 72.3 mmol) dissolved in THF (144 mL) was added to the reaction mixture. The resulting mixture was stirred for 1 hour while being heated to room temperature. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried using a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to give 33.7 g of intermediate 2-4.

[0463] (3) Preparation of compound 2

[0464]

[0465] 3-Aminodibenzofuran (513 mg, 2.8 mmol), intermediate 2-4 (3.1 g, 5.74 mmol), Pd(PtBu3)2 (72 mg, 0.14 mmol), and NaOtBu (1.08 g, 11.2 mmol) were placed in an RBF. After purging with nitrogen, toluene (14 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried over a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to give 2.9 g of compound 2. The synthesis of this compound was confirmed by LC-MS and NMR. MS: [M+H]+=1088

[0466]

[0467] Synthesis Example A-3. Preparation of Compound 3

[0468]

[0469] Compound 3 was prepared in the same manner as in Synthesis Example A-1, except that 2-aminodibenzofuran was used instead of 4-aminodibenzofuran in (5) of Synthesis Example A-1. The synthesis of the compound was confirmed by LC-MS and NMR. MS: [M+H]+=904

[0470]

[0471] Synthesis Example A-4. Preparation of Compound 4

[0472]

[0473] 2-Amino-9,9-dimethylfluorene (586 mg, 2.8 mmol), intermediate 2-4 (3.1 g, 5.74 mmol), Pd(PtBu3)2 (72 mg, 0.14 mmol), and NaOtBu (1.08 g, 11.2 mmol) were placed in an RBF. After purging with nitrogen, toluene (14 mL) was added, and the resulting mixture was stirred at 90 °C for 1 hour. Extraction was performed with ethyl acetate and water, the organic layer was collected, dried over MgSO4, and then filtered. The filtrate was dried over a vacuum rotary condenser to remove the organic solvent. After column purification, crystallization was performed under DCM / EtOH conditions to give 2.6 g of compound 4. The synthesis of this compound was confirmed by LC-MS and NMR. MS: [M+H]+=1114

[0474]

[0475] Synthesis Example A-5. Preparation of Compound 5

[0476]

[0477] Compound 5 was prepared in the same manner as in Synthesis Example A-2, except that 4-aminodibenzofuran was used instead of 3-aminodibenzofuran in (3) of Synthesis Example A-2. The synthesis of this compound was confirmed by LC-MS and NMR. MS: [M+H]+=1088

[0478]

[0479] <Examples of the preparation of ionic compounds>

[0480] Example 1: Preparation of compound D-1

[0481] (1) Preparation of intermediate D-1-1

[0482]

[0483] 1-Bromo-2,3,5,6-tetrafluoro-4-vinylbenzene (2 g, 7.84 mmol) was placed in a 50 mL round-bottom flask containing 20 mL of THF, and the resulting solution was stirred at -78 °C for 30 min. n-BuLi (3.45 mL, 8.63 mmol, 2.5 M) in hexane was slowly added to this solution, and the resulting mixture was stirred at -78 °C for 30 min. After 15 min, BCl3 (2.6 mL, 2.61 mmol, 1 M in heptane solution) was added to the reaction solution at -78 °C. The resulting solution was slowly heated to room temperature, and the reaction solution was stirred overnight, then water (30 mL) was added. The solvent was completely removed after extraction of the synthesized material with ethyl acetate (three times, 10 mL). Water was completely removed by Dean-Stark extraction with benzene, and the solid was filtered to prepare intermediate D-1-1 (800 mg, 43% yield).

[0484] (2) Preparation of compound D-1

[0485]

[0486] Intermediate D-1-1 (400 mg, 0.56 mmol), diphenyl iodine chloride (176 mg, 0.56 mmol), water (10 mL), and acetone (10 mL) were placed in a 25 mL round-bottom flask and stirred vigorously for 30 minutes. Extraction was performed using dichloromethane (three times, 10 mL) to remove the solvent, and the residue was dried to prepare compound D-1 (dopane 1) (552 mg, 100% yield).

[0487] MS:[MH] - =711 (Negative Mode)

[0488] MS:[M+H] + =281 (positive pattern)

[0489] Example 2: Preparation of ionic compounds. Example of preparation of compound D-2.

[0490] (1) Preparation of intermediate D-2-1

[0491]

[0492] Under a nitrogen atmosphere, Mg (193 mg, 7.92 mmol), I₂ (4 mg), and THF (10 mL) were placed in a 100 mL round-bottom flask and stirred for 30 minutes. 4-Bromostyrene (1.04 mL, 7.92 mmol) was added, and the flask was placed in a 30°C water bath under the round-bottom flask, with the mixture stirred overnight. The reaction solution was checked to ensure it had turned black and that Mg had dissolved. The reaction solution was diluted by adding ether (5 mL). Tris(pentafluorophenyl)borane (1 g, 3.96 mmol) was dissolved in ether (5 mL), and the resulting solution was slowly added to the reaction solution over 30 minutes. The solution was stirred overnight. Na₂CO₃ (0.1 M, 80 mL, 8.0 mmol) was slowly added to the reaction solution. The organic solvent was extracted with ethyl acetate (three times, 20 mL each time), and residual water was removed with MgSO₄. Furthermore, residual water and impurities were removed by distillation with benzene using Dean-Stark. With approximately 10 mL of solvent remaining, the solution was cooled and filtered to prepare intermediate D-2-1 (1.6 g, yield 64%).

[0493] (2) Preparation of compound D-2

[0494]

[0495] Intermediate D-2-1 (100 mg, 0.16 mmol), distilled water (10 mL), and Ph2ICl (60 mg, 0.19 mmol) were placed in a 25 mL round-bottom flask and stirred for 1 hour. A precipitate was generated by adding acetone (15 mL) to the reaction solution, and the precipitate was filtered and dried to prepare compound D-2 (dopant 2) (140 mg, 100% yield).

[0496] MS:[MH] - =615 (negative mode)

[0497] MS:[M+H] + =281 (positive pattern)

[0498] <Example of Ink Composition Preparation>

[0499] Example 1: Preparation of ink composition.

[0500] Hole injection layer substrate 1 and hole injection layer dopant 1 were mixed at a weight ratio of 8:2. Subsequently, the mixture of hole injection layer substrate 1 and hole injection layer dopant 1 was added at a concentration of 2.0 wt% to a solvent containing, respectively, 10 wt%, 15 wt%, and 75 wt% of 3-isopropylbiphenyl (represented by chemical formula A), benzyl butyrate (as a first additional solvent), and dipropylene glycol monomethyl ether (as a second additional solvent). The prepared solution was stirred for 24 hours until completely dissolved to prepare ink composition 1.

[0501] Examples of ink composition preparation 2 to 63.

[0502] Ink compositions 2 to 63 were prepared in the same manner as in ink composition preparation example 1, except that the materials shown in Table 1 below were used as the hole injection layer host 1, the hole injection layer dopant 1, the solvent represented by chemical formula A, the first additional solvent, and the second additional solvent.

[0503] Example 64: Preparation of ink composition.

[0504] Hole injection layer substrate 1 and hole injection layer dopant 1 were mixed at a weight ratio of 8:2. Subsequently, the mixture of hole injection layer substrate 1 and hole injection layer dopant 1 was added at a concentration of 2.0 wt% to a solvent containing, in amounts of 20 wt% and 80 wt% respectively, 3-isopropylbiphenyl (represented by chemical formula A) and benzyl butyrate (represented as a first additional solvent). The prepared solution was stirred for 24 hours and completely dissolved to prepare ink composition 64.

[0505] Examples of ink composition preparation 65 to 75.

[0506] Ink compositions 65 to 75 were prepared in the same manner as in ink composition preparation example 64, except that the materials shown in Table 1 below were used as hole injection layer host 1, hole injection layer dopant 1, solvent and first additional solvent.

[0507] HIL Main Body (Hole Injection Layer Main Body)

[0508]

[0509] Main Body 1

[0510]

[0511] Main Body 2

[0512]

[0513] Main Body 3

[0514]

[0515] Main Body 4

[0516]

[0517] Main body 5

[0518] HIL dopant (hole injection layer dopant)

[0519]

[0520] Dopant 1

[0521]

[0522] Dopant 2

[0523] [Table 1]

[0524]

[0525]

[0526]

[0527]

[0528] As solvents used in ink compositions 29 to 56, tastromine (CAS#91-46-3), δ-triadecanoic acid lactone (CAS#7370-92-5), 1-nonylimidazole (CAS#53657-08-2) and N-isopentyl-N-phenylpropionamide (CAS#63916-02-9) are used respectively.

[0529] <Experimental Example A>

[0530] Example 1.

[0531] After printing ink composition 1 onto an ITO substrate with a ridge formed thereon using an inkjet printing method, the printed substrate is placed in a vacuum chamber, and the pressure is reduced from atmospheric pressure to 2 × 10⁻⁶ over 60 seconds. -2 Toss, and after 180 seconds from 2×10 -2 The tonnage was reduced to 2×10 -6 The film was then dried at room temperature. After drying, it was cured by heat treatment at 230°C on a hot plate under N2 atmosphere for 1 hour. The thickness of each pixel contained in the cured film was measured using an optical thickness measuring device, namely an optical profilometer (model name: ContourGT-I) manufactured by Bruker, and the thickness uniformity V between pixels was obtained based on the measured pixel thickness using the following equation 1'. The obtained values ​​are shown in Table 2 below.

[0532] [Equation 1']

[0533]

[0534] In equation 1',

[0535] X(i) is the thickness of the i-th pixel.

[0536] Xm' is the average value of X(i) from 2 to 8, and

[0537] n' is an integer from 2 to 8.

[0538] The ITO substrate on which the embankment is formed in Example 1 corresponds to Figure 2 Printing corresponding to the ITO substrate on which the dike is formed Figure 3 , and the cured film corresponds to Figure 4 .

[0539] Examples 2 to 43 and Comparative Examples 1 to 32.

[0540] The preparation was carried out in the same manner as in Example 1, except that the ink composition shown in Table 2 below was used instead of ink composition 1, and the thickness uniformity V was obtained and shown in Table 2 below.

[0541] [Table 2]

[0542]

[0543]

[0544] As shown in Table 2, it can be determined that the examples using an ink composition according to an exemplary embodiment of the present invention have a small thickness uniformity V value of 0.4 or less, particularly the examples using a solvent of chemical formula C-1 (specifically, butyl benzoate) as a first additional solvent while using two other solvents have a very small thickness uniformity V value of 0.2 or less, and the comparative examples using an ink composition not corresponding to the present invention have a large thickness uniformity V value of greater than 0.4.

[0545] In this regard, Figures 5 to 16 The thickness uniformity characteristics of pixels according to experimental examples of this application are shown. Specifically, Figure 5 , Figure 6 , Figure 11 and Figure 12 The thickness uniformity of pixels according to embodiments 6, 16, 36 and 40 of this application are shown respectively. Figures 7 to 10 and Figures 13 to 16The thickness uniformity of pixels in Comparative Examples 5, 10, 15, 27, and 29 to 32 according to this application is shown respectively, with the horizontal axis representing the distance between pixels (μm) and the vertical axis representing the pixel thickness (nm). Figure 5 , Figure 6 , Figure 11 and Figure 12 As shown in the content, it can be determined that Examples 6, 16, 36, and 40, using an ink composition according to an exemplary embodiment of the present invention, have pixel thickness uniformity V of 0.13, 0.21, 0.26, and 0.07 (these are small values ​​of 0.4 or less), respectively, and therefore have uniform thickness uniformity. Therefore, since the ink composition is used in organic material layers, etc., in organic light-emitting devices, excellent luminescence and / or coloring effects can be expected by reducing the factors affecting the interference conditions of light emitted from the light-emitting device according to the influence of thickness. Conversely, it can be determined that Comparative Examples 5, 10, 15, 27, and 29 to 32, using ink compositions not corresponding to the present invention, have pixel thickness uniformity V of 0.84, 0.67, 0.70, 0.62, 0.57, 0.71, 0.89, and 0.48 (these are values ​​greater than 0.4), respectively, with large thickness differences between pixels and unbalanced thickness uniformity.

[0546] <Experimental Example B>

[0547] Example B-1.

[0548] The thin film is coated with a material that has A glass substrate with a thickness of ITO (indium tin oxide) and patterned with hydrophobic banks was washed with distilled water for 30 minutes and then dried on a hot plate at 230°C for 10 minutes. Ink composition 1 from Table 1 was inkjet printed onto the washed, patterned, banked substrate and heat-treated at 230°C for 30 minutes to form a hole injection layer with a thickness of 30 nm. A hole transport layer with a thickness of 40 nm was formed on the hole injection layer by inkjet printing with an ink prepared by dissolving the following α-NPD compound in cyclohexylbenzene at a concentration of 2% by weight. Subsequently, 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 a thickness of 20 nm to form a light-emitting layer. The following BCP compound was vacuum deposited on the light-emitting layer to a thickness of 35 nm to form an electron injection and transport layer. Organic light-emitting devices are fabricated by depositing LiF and aluminum on the electron injection and transport layers to form cathodes with thicknesses of 1 nm and 100 nm, respectively.

[0549]

[0550] Examples B-2 to B-43.

[0551] Organic light-emitting devices were manufactured using ink compositions from Table 3 below instead of ink composition 1 in Example B-1.

[0552] [Table 3]

[0553]

[0554]

[0555] It was determined that the organic light-emitting devices manufactured in Examples B-1 to B-43 were driven. Therefore, it was determined that the ink composition according to an exemplary embodiment of the present invention can be applied to organic light-emitting devices.

Claims

1. An ink composition comprising a compound represented by chemical formula 1, a solvent represented by chemical formula A, and a first additional solvent represented by chemical formula C-1 or chemical formula C-2: [Chemical Formula 1] ， [Chemical Formula A] ， [Chemical formula C-1] ， [Chemical formula C-2] ， in, Among chemical formulas 1, A, C-1, and C-2, Y can be O, S, CRaRb, or SiRcRd. Cy1 and Cy2 may be the same as or different from each other, and each is independently a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring. Ra, Rb, Rc, and Rd may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, or bonded to adjacent groups to form substituted or unsubstituted rings. L1 to L3 may be identical or different from each other, and each is an independent direct bond; or substituted or unsubstituted aryl groups. L11 and L12 may be the same as or different from each other, and each is independently a direct bond; substituted or unsubstituted alkylene groups; or substituted or unsubstituted aryl groups. X1 and X2 may be the same as or different from each other, and each is an independent curable group. R1 and R2 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. R3 and R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl. a, b, and c are each 0 or 1. n1 and n2 are each integers from 0 to 7, and when n1 and n2 are each 2 or greater, the two or more substituents in parentheses are either the same or different from each other. m1 and m2 are each integers from 1 to 5, n3 and n4 are each integers from 0 to 4, m1 + n3 is 5 or less, and m2 + n4 is 5 or less. Y1 to Y10 may be the same as or different from each other, and each is 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. L100 and L101 may be the same as or different from each other, and each is independently a direct bond; or substituted or unsubstituted alkylene groups. G1 and G3 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl. G2 is a straight-chain alkyl group. G4 is a substituted or unsubstituted alkyl group, and g1 and g3 are each integers from 1 to 5, and when g1 and g3 are each 2 or greater, the two or more substituents in parentheses are the same or different from each other.

2. The ink composition according to claim 1, wherein the curable group is selected from any of the following structures: ， In the structure, Lc1 is a direct bond; -O-; -S-; substituted or unsubstituted alkylene; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl. lc is 1 or 2. When lc is 2, Lc1 can be the same or different from each other. Rc1 is a substituted or unsubstituted alkyl group, and This refers to the portion that is bonded to chemical formula 1.

3. The ink composition according to claim 1, wherein the curable group is selected from any of the following structures: 。 4. The ink composition according to claim 1, wherein Y1 to Y10 are the same 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.

5. The ink composition according to claim 1, wherein the solvent represented by chemical formula A is selected from any of the following compounds: 。 6. The ink composition according to claim 1, wherein the surface tension of the solvent represented by chemical formula A is from 33 mN / m to 37 mN / m.

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

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

9. The ink composition according to claim 1, wherein chemical formula 1 is selected from any of the following compounds: ， ， ， ， ， ， ， ， ， ， ， ， 。 10. 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 chemical formula 2, At least one of R201 to R220 is F; cyano; or a substituted or unsubstituted fluoroalkyl group. At least one of R201 to R220 is a curable group. The remaining R201 to R220 may be the same as or different from each other, and each independently represents hydrogen; deuterium; nitro; -C(O)R220'; -OR221; -SR222; -SO3R223; -COOR224; -OC(O)R225; -C(O)NR226R227; substituted or unsubstituted alkyl; substituted or unsubstituted fluoroalkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted alkynyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic groups, and R220' and R221 to R227 are the same as or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

11. The ink composition according to claim 10, wherein chemical formula 2 is selected from any of the following compounds: ， ， ， In the compound, n is an integer from 1 to 3, m is an integer from 1 to 3, and m + n = 4. q is an integer from 0 to 3, r is an integer from 1 to 4, and q + r = 4. Z represents deuterium; halogen group; nitro group; cyano group; amino group; -C(O)R220'; -OR221; -SR222; -SO3R223; -COOR224; -OC(O)R225; -C(O)NR226R227; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted amino group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group. l is an integer from 1 to 4, and when l is 2 or greater, Z are either the same or different from each other. R220' and R221 to R227 are the same as or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

12. The ink composition according to claim 10, wherein the ionic compound further comprises a cationic group. The cationic group is a monovalent cationic group; Compound; or selected from any of the following structural formulas: ， In the aforementioned structural formula, X1 to X 76 They may be the same as or different from each other, and each independently is hydrogen; deuterium; cyano; nitro; halogen group; -COOR224; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted cycloalkyl; substituted or unsubstituted fluoroalkyl; substituted or unsubstituted aryl; or curable group. R224 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group. p is an integer from 0 to 10, and a1 is 1 or 2, b1 is 0 or 1, and a1 + b1 = 2.

13. The ink composition of claim 12, wherein the ink composition further comprises one or more second additional solvents selected from: tetrahydronaphthalene, 4-methoxytoluene, tetrahydrofuran, dichloronaphthalene, 4-methoxytoluene, tetrahydrofuran, dichloronaphthalene, 4-methoxytoluene, tetrahydrofuran, dichloronaphthalene, tetrahydro ... Alkane, dipropylene glycol monomethyl ether and tripropylene glycol monomethyl ether.

14. The ink composition according to claim 13, wherein, based on 100% by weight of the ink composition, The compound represented by chemical formula 1 is included in an amount of 0.1% to 15% by weight; The solvent represented by chemical formula A is included in an amount of 1% to 70% by weight; The ionic compound containing an anionic group represented by chemical formula 2 is included in an amount of 0.1% to 15% by weight; and The additional solvent is included in an amount of 10% to 85% by weight.

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

16. An organic material layer comprising the pixel according to claim 15.

17. The organic material layer of claim 16, wherein the organic material layer comprises n' pixels. The n' pixels have a thickness uniformity V of 0.4 or less, and The thickness uniformity V satisfies the following equation 1: [Equation 1] ， In equation 1, X(i) is the thickness of the i-th pixel. Xm' is the average value of X(i) where i is from 2 to n', and n' is 2 to 10 4 Integers.

18. An organic light-emitting device, comprising: First electrode; Second electrode; as well as An organic material layer having one or more layers is disposed between the first electrode and the second electrode. One or more of the organic material layers are organic material layers according to claim 16.

19. The organic light-emitting device of claim 18, wherein the organic material layer comprises 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 The layer selected from one or more of the hole injection layer, hole transport layer, hole injection and transport layer, and electron blocking layer comprises the ink composition or a cured product thereof.

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