Ink compound and organic light emitting device using same

Abstract

The present invention relates to an ink composition and an organic light-emitting device using the same.

Description

Technology Field

[0001] The present invention relates to an ink composition and an organic light-emitting device using the same. Background Technology

[0002] When fabricating organic light-emitting diodes using a solution process, there is an advantage in that it is easier to produce them using a large-area front-emitting method compared to the deposition process.

[0003] However, unlike deposition processes, in solution processes, thin films may not be formed uniformly during the drying process and localized clumping may occur due to differences in solvent solubility and other physical properties between the host and dopant. Specifically, since the host and dopant materials have different physical properties, they exhibit different solubility characteristics in specific solvents. When a specific solvent is selected for ink formation of the two materials, if the solubility of each solute differs, there is a high probability that clumping of the solute with relatively poor solubility will occur during the drying process; consequently, it is difficult to expect normal operation when the actual device is fabricated due to this clumping.

[0004] In addition, when the host, dopant, and solvent are inked, there is a problem in that the solutes in the ink composition harden as the ink turns reddish-brown when exposed to light. Specifically, when the ink composition is exposed to light, radicals of the host and dopant materials are formed following the initiation of cations, and the cations of the dopant interact with the anions of the host and dopant, causing hardening, which makes it unusable for the manufacture of organic light-emitting diodes for solution processes.

[0005] Therefore, there is a need for an ink composition that can uniformly form host and dopant materials within the partition and contains a host and a dopant while having a slow discoloration rate. Prior art literature

[0006] Korean Patent Publication No. 10-2012-0112277 The problem to be solved

[0007] The purpose of the present invention is to provide an ink composition comprising a discoloration control agent and an organic light-emitting device using the same. means of solving the problem

[0008] One embodiment of the present invention is

[0009] An ink composition comprising a compound represented by the following chemical formula 101, a second compound, and a discoloration control agent,

[0010] The above discoloration control agent comprises one or more non-covalent electron pairs, and

[0011] The above-mentioned second compound provides an ink composition represented by the following chemical formula 201 or the following chemical formula 301.

[0012] [Chemical Formula 101]

[0013]

[0014] In the above chemical formula 101,

[0015] L101 is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0016] R101 to R106 are identical or different from one another and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0017] Ar101 and Ar102 are identical or different from each other and are each independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups, and

[0018] X101 and X102 are identical or different from each other, and each is independently a hardening group, and

[0019] n101 and n104 are each independently integers from 0 to 5, and

[0020] n102 and n106 are each independently integers from 0 to 4, and

[0021] n103 and n105 are each independently integers from 0 to 3, and

[0022] If n101 to n106 are each 2 or more, the substituents within the parentheses are identical or different from each other, and

[0023] m101 and m102 are 0 or 1, respectively, and

[0024] [Chemical Formula 201]

[0025]

[0026] In the above chemical formula 201,

[0027] Ar201 to Ar204 are the same or different from each other, at least one of Ar201 to Ar204 is represented by the following chemical formula 202, and the remaining Ar201 to Ar204 are represented by the following chemical formula 203, and

[0028] [Chemical Formula 202]

[0029]

[0030] In the above chemical formula 202,

[0031] At least one of R201 to R205 is F; a cyano group; or a substituted or unsubstituted fluoroalkyl group, and

[0032] At least one of the remaining R201 to R205 is a curable group, and

[0033] The remaining R201 to R205 are the same or different from one another and are each independently hydrogen; deuterium; nitro group; -C(O)R200'; -OR201'; -SR202'; -SO3R203'; -COOR204'; -OC(O)R205'; -C(O)NR206'R207'; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group,

[0034] R200' to R207' are the same or different from one another, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group, and

[0035] [Chemical Formula 203]

[0036]

[0037] In the above chemical formula 203,

[0038] At least one of R206 to R210 is a curable group, and

[0039] The remaining R206 to R210 are the same or different from one another and are each independently hydrogen; deuterium; a nitro group; -C(O)R200'; -OR201'; -SR202'; -SO3R203'; -COOR204'; -OC(O)R205'; -C(O)NR206'R207'; a substituted or unsubstituted alkyl group; a substituted or unsubstituted fluoroalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and R200' to R207' are the same or different from one another and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group, and

[0040] [Chemical Formula 301]

[0041]

[0042] In the above chemical formula 301,

[0043] Ar'201 to Ar'204 are identical or different from each other, and at least one of Ar'201 to Ar'204 is an aryl group having 6 to 30 carbon atoms substituted with a vinyl group, and the remaining Ar'201 to Ar'204 are aryl groups having 6 to 30 carbon atoms substituted with a halogen group.

[0044] Another embodiment of the present invention is a first electrode;

[0045] Second electrode;

[0046] It includes one or more organic layers provided between the first electrode and the second electrode, and

[0047] The present invention provides an organic light-emitting device in which one or more of the above organic layers comprise the aforementioned ink composition or a cured product thereof. Effects of the invention

[0048] An ink composition according to one embodiment of the present invention can be used to manufacture organic light-emitting diodes for solution processes.

[0049] An ink composition according to one embodiment of the present invention has the advantage of preventing the ink composition from discoloring and preventing unnecessary curing action.

[0050] An ink composition according to one embodiment of the present invention has excellent stability. Brief explanation of the drawing

[0051] FIG. 1 illustrates an organic light-emitting device using an ink composition according to one embodiment of the present invention. Figures 2 and 3 respectively illustrate the change in redness of the ink composition before and after in Experimental Examples 24 to 31 of the present invention. Figures 4 and 5 respectively illustrate the change in redness of the ink composition before and after in Experimental Examples 32 to 35 of the present invention. Figures 6 and 7 respectively show the change in redness of the ink composition before and after in Experimental Examples 36 to 40 of the present invention. FIGS. 8 and 9 respectively illustrate the change in redness of the ink composition in Experimental Examples 1 to 5 of the present invention. FIGS. 10 and 11 respectively illustrate the change in redness of the ink composition in Experimental Examples 6 to 9 of the present invention. FIGS. 12 and 13 respectively illustrate the change in redness of the ink composition before and after in Experimental Examples 10 to 19 of the present invention. FIGS. 14 and 15 respectively illustrate the change in redness of the ink composition before and after in Experimental Examples 20 to 23 of the present invention. Specific details for implementing the invention

[0052] The present invention will be described in detail below.

[0053] One embodiment of the present invention is

[0054] An ink composition comprising a compound represented by the following chemical formula 101, a second compound, and a discoloration control agent,

[0055] The above discoloration control agent comprises one or more non-covalent electron pairs, and

[0056] The above-mentioned second compound provides an ink composition represented by the following chemical formula 201 or the following chemical formula 301.

[0057] [Chemical Formula 101]

[0058]

[0059] In the above chemical formula 101,

[0060] L101 is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0061] R101 to R106 are identical or different from one another and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0062] Ar101 and Ar102 are identical or different from each other and are each independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups, and

[0063] X101 and X102 are identical or different from each other, and each is independently a hardening group, and

[0064] n101 and n104 are each independently integers from 0 to 5, and

[0065] n102 and n106 are each independently integers from 0 to 4, and

[0066] n103 and n105 are each independently integers from 0 to 3, and

[0067] If n101 to n106 are each 2 or more, the substituents within the parentheses are identical or different from each other, and

[0068] m101 and m102 are 0 or 1, respectively, and

[0069] [Chemical Formula 201]

[0070]

[0071] In the above chemical formula 201,

[0072] Ar201 to Ar204 are the same or different from each other, at least one of Ar201 to Ar204 is represented by the following chemical formula 202, and the remaining Ar201 to Ar204 are represented by the following chemical formula 203, and

[0073] [Chemical Formula 202]

[0074]

[0075] In the above chemical formula 202,

[0076] At least one of R201 to R205 is F; a cyano group; or a substituted or unsubstituted fluoroalkyl group, and

[0077] At least one of the remaining R201 to R205 is a curable group, and

[0078] The remaining R201 to R205 are the same or different from one another and are each independently hydrogen; deuterium; nitro group; -C(O)R200'; -OR201'; -SR202'; -SO3R203'; -COOR204'; -OC(O)R205'; -C(O)NR206'R207'; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group,

[0079] R200' to R207' are the same or different from one another, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group, and

[0080] [Chemical Formula 203]

[0081]

[0082] In the above chemical formula 203,

[0083] At least one of R206 to R210 is a curable group, and

[0084] The remaining R206 to R210 are the same or different from one another and are each independently hydrogen; deuterium; a nitro group; -C(O)R200'; -OR201'; -SR202'; -SO3R203'; -COOR204'; -OC(O)R205'; -C(O)NR206'R207'; a substituted or unsubstituted alkyl group; a substituted or unsubstituted fluoroalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and R200' to R207' are the same or different from one another and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group, and

[0085] [Chemical Formula 301]

[0086]

[0087] In the above chemical formula 301,

[0088] Ar'201 to Ar'204 are identical or different from each other, and at least one of Ar'201 to Ar'204 is an aryl group having 6 to 30 carbon atoms substituted with a vinyl group, and the remaining Ar'201 to Ar'204 are aryl groups having 6 to 30 carbon atoms substituted with a halogen group.

[0089] The above ink composition prevents discoloration and curing of the ink composition by including a discoloration control agent having one or more non-covalent electron pairs. Specifically, the non-covalent electron pairs included in the discoloration control agent can suppress radical formation and mutual bonding reactions by preventing the cations and anions of the dopant from interacting with the host. As a result, the stability of the ink composition can be improved and it can be used in the manufacture of organic light-emitting diodes for solution processes.

[0090] In the present invention, when it is stated that a certain member (layer) is located "on" another member (layer), this includes not only the case where a certain member (layer) is in contact with another member, but also the case where another member (layer) exists between the two members (layers).

[0091] In the present invention, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0092] In the present invention, the term "layer" is used in the sense of a "film" commonly used in the art and refers to a coating that covers a desired area. The size of the "layer" is not limited, and each "layer" may have the same or different size. According to one embodiment, the size of the "layer" may be equal to the size of the entire device, correspond to the size of a specific functional area, or be as small as a single subpixel.

[0093] Unless otherwise defined in this invention, all technical and scientific terms used in this invention have the same meaning as commonly understood by those skilled in the art to which this invention pertains. Methods and materials similar or equivalent to those described in this invention may be used in the practice or testing of embodiments of this invention, but suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned in this invention are incorporated by reference in their entirety to this invention, and in the event of conflict, this invention, including definitions, shall prevail unless a specific passage is mentioned. Furthermore, materials, methods, and embodiments are merely illustrative and are not intended to be limiting.

[0094] In the present invention, the term "combination thereof" included in a Markush-style expression means one or more mixtures or combinations selected from a group consisting of components described in the Markush-style expression, and means including one or more selected from the group consisting of said components.

[0095] Examples of substituents in the present invention are described below, but are not limited thereto.

[0096] In the present invention, " " and "---" each represent the connected parts.

[0097] In the present invention, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution location is not limited to the location where the hydrogen atom is substituted, that is, any location where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0098] In the present invention, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of hydrogen; deuterium; halogen group; sulfonyl group; ether group; ester group; alkyl group; cycloalkyl group; alkenyl group; alkynyl group; amine group; aryl group; and heteroaryl group, or is substituted with a substituent in which two or more of the exemplified substituents are connected, or has no substituents.

[0099] In the present invention, the connection of two or more substituents means that a hydrogen of one substituent is connected to another substituent. For example, an isopropyl group and a phenyl group are connected or It can be a substituent of.

[0100] In the present invention, the connection of three substituents includes not only the case where (substituent 1)-(substituent 2)-(substituent 3) are connected in succession, but also the case where (substituent 2) and (substituent 3) are connected to (substituent 1). For example, two phenyl groups and isopropyl groups are connected or It can be a substituent. The same applies to the connection of 4 or more substituents as described above.

[0101] In the present invention, the halogen group is a fluoro group (-F), a chloro group (-Cl), a bromo group (-Br), or an iodo group (-I).

[0102] In the present invention, the nitro group is -NO2.

[0103] In the present invention, the nitrile group is -CN, coordinates to a metal, is easily switched between a coordinated state and a free non-coordinated state, and is a non-ionic functional group.

[0104] In the present invention, the sulfonyl group is -SO2R sulfonyl It may be, and the above R sulfonylIt may be selected from the group consisting of hydrogen; deuterium; hydroxyl group; halogen group; nitrile group; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. Additionally, the sulfonyl group may include a sulfonic acid group. For example, R sulfonyl In the case of this hydroxyl group, the sulfonyl group becomes -SO3H, which signifies a sulfonic acid group, and accordingly, the sulfonyl group includes a sulfonic acid group.

[0105] In the present invention, the ether group is -OR ETER It may be, and the above R ETER It may be selected from the group consisting of hydrogen; deuterium; hydroxyl group; halogen group; nitrile group; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0106] In the present invention, the ester group is -COOR ESTER It may be, and the above R ESTER It may be selected from the group consisting of hydrogen; deuterium; hydroxyl group; halogen group; nitrile group; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0107] In the present invention, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30; 1 to 20; 1 to 10; or 1 to 5. Specific examples include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl.

[0108] The above alkyl group may include an alkyl group substituted with a halogen group. Specific examples include a methyl group substituted with three fluoro groups, namely a trifluoromethyl group, but are not limited thereto.

[0109] In the present invention, the cycloalkyl group is not particularly limited, but the number of carbon atoms is not particularly limited, but is preferably 3 to 60; 3 to 30; or 3 to 20. Specific examples of the cycloalkyl group include, but are not limited to, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc.

[0110] In the present invention, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30; 2 to 20; 2 to 10; or 2 to 5. Specific examples include a vinyl group; 1-propenyl group; isopropenyl group; 1-butenyl group; 2-butenyl group; 3-butenyl group; 1-pentenyl group; 2-pentenyl group; 3-pentenyl group; 3-methyl-1-butenyl group; 1,3-butadienyl group; allyl group; 1-phenylvinyl-1-yl group; 2-phenylvinyl-1-yl group; 2,2-diphenylvinyl-1-yl group; 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group; 2,2-bis(diphenyl-1-yl)vinyl-1-yl group; stilbenyl group; Styrenyl groups, etc., are included, but are not limited to these.

[0111] In the present invention, the alkynyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30; 2 to 20; 2 to 10; or 2 to 5.

[0112] In the present invention, an aryl group refers to a monovalent aromatic hydrocarbon or a derivative of an aromatic hydrocarbon. In the present invention, an aromatic hydrocarbon refers to a compound comprising a planar ring in which pi electrons are completely conjugated, and a group derived from an aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed to an aromatic hydrocarbon. Furthermore, in the present invention, the aryl group is intended to include a monovalent group in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are connected to each other. The aryl group is not particularly limited, but it is preferable that it has 6 to 60 carbon atoms; 6 to 50; 6 to 30; 6 to 25; 6 to 20; 6 to 18; 6 to 15; 6 to 13; or 6 to 12 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group.

[0113] The above monocyclic aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms; 6 to 54; 6 to 48; 6 to 42; 6 to 36; 6 to 30; 6 to 24; 6 to 18; or 6 to 12 carbon atoms, and specifically may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

[0114] The above polycyclic aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms; 6 to 45 carbon atoms; 6 to 30 carbon atoms; 6 to 22 carbon atoms; 6 to 22 carbon atoms; 6 to 20 carbon atoms; 6 to 18 carbon atoms; 6 to 16 carbon atoms; 6 to 15 carbon atoms; 6 to 14 carbon atoms; 6 to 13 carbon atoms; 6 to 12 carbon atoms; or 6 to 10 carbon atoms. It may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

[0115] In the present invention, a heteroaryl group refers to a monovalent aromatic heterocyclic group. Here, an aromatic heterocyclic group refers to a monovalent group of an aromatic ring or a derivative of an aromatic ring, comprising one or more heteroatoms selected from the group consisting of N, O, P, S, Si, and Se. The derivative of the aromatic ring includes all structures in which an aromatic ring or an aliphatic ring is condensed to an aromatic ring. Furthermore, in the present invention, the heteroaryl group is intended to include a monovalent group in which two or more aromatic rings containing heteroatoms or derivatives of aromatic rings containing heteroatoms are connected to each other. It is preferable that the number of carbon atoms of the heteroaryl group be 2 to 60; 2 to 50; 2 to 30; 2 to 20; 2 to 18; or 2 to 13. Examples of heteroaryl groups include, but are not limited to, thiophene, furanyl, pyrrole, imidazole, thiazole, oxazole, pyridine, pyrimidine, triazine, triazole, acridine, pyridazine, pyrazine, quinoline, quinazolin, quinoxaline, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophen, dibenzothiophen, benzofuran, phenanthrolinyl, and dibenzofuran groups.

[0116] In the present invention, the heteroaryl group may be a monocyclic or polycyclic ring and may be an aromatic, aliphatic, or a condensed ring of aromatic and aliphatic.

[0117] In the present invention, a 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 comprising one or more heteroatoms selected from the group consisting of N, O, P, S, Si, and Se.

[0118] In the present invention, the aliphatic ring is a non-aromatic hydrocarbon ring, and examples include the aforementioned cycloalkyl group, adamantyl group, etc.

[0119] In the present invention, the aromatic ring may be subject to the aforementioned aryl group.

[0120] In the present invention, "adjacent group" may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the atom in stereostructure, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

[0121] In the present invention, in a substituted or unsubstituted ring formed by joining together, "ring" means a hydrocarbon ring; or a hetero ring.

[0122] In the present invention, the hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of aromatic and aliphatic. Examples of condensed rings of aromatic and aliphatic include, but are not limited to, 1,2,3,4-tetrahydronaphthalene groups and 2,3-dihydro-1H-indene groups.

[0123] In the present invention, the description of the heterocyclic group may apply except that the heterocyclic group is divalent.

[0124] In the present invention, the description of the aryl group described above may apply except that the aromatic hydrocarbon ring is a divalent group.

[0125] In the present invention, the description of the cycloalkyl group described above may apply except that the aliphatic hydrocarbon ring is a divalent group.

[0126] In the present invention, the curable group can carry out polymerization or crosslinking reactions, thereby carrying out large molecular weight reactions, and there are thermosetting groups that are cured by heat or photocurable groups that are cured by light, etc.

[0127] The above-mentioned curable group may be any one selected from the following structures, but is not limited to the following structures.

[0128]

[0129]

[0130] In the above structures,

[0131] Lc is a direct bond; -O-; -S-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0132] lc1 is 1 or 2, and

[0133] When lc1 is 2, the above Lc are the same or different from each other.

[0134] According to one embodiment of the present invention, Lc is a direct bond; a methylene group; or an ethylene group.

[0135] In another embodiment, Lc is a direct connection.

[0136] According to one embodiment of the present invention, Rc1 is a substituted or unsubstituted alkyl group.

[0137] According to one embodiment of the present invention, Rc1 is a methyl group or an ethyl group.

[0138] According to another embodiment, Rc1 is a methyl group.

[0139] In the present invention, the cured product of the composition is in a state where the composition has been heat-treated or photo-treated.

[0140] The following is information regarding discoloration control agents.

[0141] According to one embodiment of the present invention, the discoloration control agent is represented by the following chemical formula 1 or chemical formula 2.

[0142] [Chemical Formula 1]

[0143]

[0144] [Chemical Formula 2]

[0145]

[0146] In the above chemical formula 1,

[0147] L1 is a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms; or a substituted or unsubstituted arylalkylene group having 7 to 11 carbon atoms, and

[0148] X1 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and

[0149] n1 is an integer from 1 to 5, and

[0150] In the above chemical formula 2,

[0151] L2 is a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms, and

[0152] X2 and X3 are identical or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and

[0153] n2 is an integer from 2 to 8.

[0154] According to one embodiment of the present invention, the discoloration control agent is represented by the chemical formula 1.

[0155] The discoloration control agent represented by Chemical Formula 1 contains one or more -OH and one or more -O- groups within the compound, and thus contains at least four non-covalent electron pairs. Accordingly, an ink composition containing the discoloration control agent can suppress radical formation and inter-solute bonding reactions by means of the non-covalent electron pairs. As a result, the stability of the ink composition can be improved, and it can be used in the manufacture of organic light-emitting devices for solution processes. In addition, the discoloration inhibitor represented by Chemical Formula 1 contains a number of non-covalent electron pairs within the compound, and other substituents that do not contain non-covalent electron pairs can be additionally introduced, thereby appropriately controlling the polarity or non-polarity of the discoloration inhibitor.

[0156] According to one embodiment of the present invention, L1 is a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms; or a substituted or unsubstituted arylalkylene group having 7 to 15 carbon atoms.

[0157] According to one embodiment of the present invention, L1 is a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms; or a substituted or unsubstituted arylalkylene group having 7 to 11 carbon atoms.

[0158] According to one embodiment of the present invention, L1 is an alkylene group having 1 to 3 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; or an arylalkylene group having 7 to 11 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

[0159] According to one embodiment of the present invention, L1 is an alkylene group having 1 to 3 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 5 carbon atoms; or an arylalkylene group having 7 to 11 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 5 carbon atoms.

[0160] According to one embodiment of the present invention, L1 is an alkylene group having 1 to 3 carbon atoms substituted or unsubstituted with a methyl group; or an arylalkylene group having 7 to 11 carbon atoms substituted or unsubstituted with a methyl group.

[0161] According to one embodiment of the present invention, L1 is a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms; or -L11-L12-, wherein either L11 and L12 is a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms, and the other is a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.

[0162] According to one embodiment of the present invention, L1 is a substituted or unsubstituted methylene group; a substituted or unsubstituted ethylene group; a substituted or unsubstituted propylene group; or -L11-L12-, and either L11 and L12 is a substituted or unsubstituted methylene group, and the other is a substituted or unsubstituted phenylene group.

[0163] According to one embodiment of the present invention, L1 is a substituted or unsubstituted methylene group; a substituted or unsubstituted ethylene group; a substituted or unsubstituted propylene group; or -L11-L12-, and either one of L11 and L12 is a methylene group, and the other is a phenylene group.

[0164] According to one embodiment of the present invention, L1 is a methylene group; an ethylene group substituted or unsubstituted with a methyl group; a propylene group; or -L11-L12-, and either of L11 and L12 is a methylene group, and the other is a phenylene group.

[0165] According to one embodiment of the present invention, L1 is a methylene group; an ethylene group; a propylene group; an isopropylene group; or -L11-L12-, and either of L11 and L12 is a methylene group, and the other is a phenylene group.

[0166] According to one embodiment of the present invention, L1 is a methylene group; an ethylene group; a propylene group; an isopropylene group; or -L11-L12-, wherein L11 is a methylene group and L12 is a phenylene group.

[0167] According to one embodiment of the present invention, X1 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

[0168] According to one embodiment of the present invention, X1 is a carbon-1 to carbon-4 alkyl group substituted or unsubstituted with a substituted or unsubstituted aryl group.

[0169] According to one embodiment of the present invention, X1 is an alkyl group having 1 to 4 carbon atoms that is substituted or unsubstituted with an aryl group.

[0170] According to one embodiment of the present invention, X1 is an alkyl group having 1 to 4 carbon atoms that is substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.

[0171] According to one embodiment of the present invention, X1 is an alkyl group having 1 to 4 carbon atoms that is substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

[0172] According to one embodiment of the present invention, X1 is an alkyl group having 1 to 4 carbon atoms that is substituted or unsubstituted with an aryl group having 6 to 10 carbon atoms.

[0173] According to one embodiment of the present invention, X1 is an alkyl group having 1 to 4 carbon atoms that is substituted or unsubstituted with a phenyl group.

[0174] According to one embodiment of the present invention, X1 is a methyl group substituted or unsubstituted with a phenyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; or a substituted or unsubstituted butyl group.

[0175] According to one embodiment of the present invention, X1 is a methyl group substituted or unsubstituted with a phenyl group; a substituted or unsubstituted ethyl group; or a substituted or unsubstituted butyl group.

[0176] According to one embodiment of the present invention, X1 is a methyl group substituted or unsubstituted with a phenyl group; an ethyl group; or a butyl group.

[0177] According to one embodiment of the present invention, the chemical formula 1 is any one selected from the group of compounds 1 consisting of the following compounds.

[0178] [Compound Group 1]

[0179] .

[0180] According to one embodiment of the present invention, the discoloration control agent is any one selected from the group of compounds 1 consisting of the above compounds.

[0181] According to one embodiment of the present invention, the discoloration control agent is a mixture of two or more compounds selected from the group of compounds 1 consisting of the above compounds.

[0182] According to one embodiment of the present invention, the discoloration control agent is represented by the chemical formula 2.

[0183] The discoloration control agent represented by Chemical Formula 2 above contains two or more -O- groups within the compound, and thus contains at least four non-covalent electron pairs. Accordingly, like the discoloration control agent represented by Chemical Formula 1 above, it can be included in an ink composition to suppress radical formation and mutual bonding reactions between solutes, and consequently improve the stability of the ink composition, so that it can be used in the manufacture of organic light-emitting diodes for solution processes.

[0184] According to one embodiment of the present invention, L2 is a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms.

[0185] According to one embodiment of the present invention, L2 is an alkylene group having 1 to 3 carbon atoms that is substituted or unsubstituted with a methyl group.

[0186] According to one embodiment of the present invention, L2 is an alkylene group having 1 to 3 carbon atoms.

[0187] According to one embodiment of the present invention, L2 is a substituted or unsubstituted methylene group; a substituted or unsubstituted ethylene group; or a substituted or unsubstituted propylene group.

[0188] According to one embodiment of the present invention, L2 is a methylene group; an ethylene group; or a propylene group.

[0189] According to one embodiment of the present invention, L2 is an ethylene group; or a propylene group.

[0190] According to one embodiment of the present invention, X2 and X3 are identical or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

[0191] According to one embodiment of the present invention, X2 and X3 are identical or different from each other and are each independently substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms.

[0192] According to one embodiment of the present invention, X2 and X3 are identical or different from each other and are each independently alkyl groups having 1 to 4 carbon atoms.

[0193] According to one embodiment of the present invention, X2 and X3 are identical or different from each other and are each independently a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; or a substituted or unsubstituted butyl group.

[0194] According to one embodiment of the present invention, X2 and X3 are identical or different from each other and are each independently a methyl group; an ethyl group; a propyl group; or a butyl group.

[0195] According to one embodiment of the present invention, X2 and X3 are identical or different from each other and are each independently a methyl group or a butyl group.

[0196] According to one embodiment of the present invention, if the number of carbon atoms in either X2 or X3 is 2 or more, the number of carbon atoms in the other is 1. For example, if the number of carbon atoms in X2 is 2 or more, the number of carbon atoms in X3 is 1. For another example, if the number of carbon atoms in X3 is 2 or more, the number of carbon atoms in X2 is 1.

[0197] According to one embodiment of the present invention, the formula 2 is any one selected from the group of compounds 2 consisting of the following compounds.

[0198] [Compound Group 2]

[0199] .

[0200] According to one embodiment of the present invention, the discoloration control agent is any one selected from group 2 of compounds consisting of the above compounds.

[0201] According to one embodiment of the present invention, the discoloration control agent is a mixture of two or more compounds selected from the group of compounds 2 consisting of the above compounds.

[0202] According to one embodiment of the present invention, the discoloration control agent is 2-(2-methoxyethoxy)ethanol, 2-2-(2-methoxyethoxy)ethoxyethanol, diethyleneglycol monobutylether, 2-2-(2-ethoxyethoxy)ethoxyethanol, dipropyleneglycol n-butylether, tetraethyleneglycol monomethylether, tripropylene glycol monomethyl ether, dipropylene glycol monomethyl ether, diethyleneglycol monobenzyl ether, It includes one or more compounds selected from the group consisting of triethyleneglycol monobenzyl ether, 2-(benzyloxy)ethanol, 3-methoxybenzyl alcohol, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, triethylene glycol butyl methyl ether, and diethylene glycol butyl methyl ether.

[0203] According to another embodiment of the present invention, the discoloration control agent comprises a compound represented by Formula 1 and a compound represented by Formula 2. In this case, the compound represented by Formula 1 and the compound represented by Formula 2 may be included in a weight ratio of 1:9 to 9:1, but are not limited thereto.

[0204] According to one embodiment of the present invention, the boiling point of the discoloration control agent is 150 ℃ to 300 ℃; 160 ℃ to 300 ℃ or 170 ℃ to 290 ℃.

[0205] According to one embodiment of the present invention, under conditions of 25°C and 1 atmosphere, the solubility of the discoloration control agent in water is 10 g / L to 20 g / L; 12 g / L to 18 g / L; or 12.5 g / L to 17.5 g / L.

[0206] The following is information regarding hole injection materials.

[0207] The above hole injection material includes a hole injection layer host and / or a hole injection layer dopant.

[0208] The following is information regarding the hole injection layer host.

[0209] According to one embodiment of the present invention, the compound represented by the aforementioned chemical formula 101 is a hole injection layer host.

[0210] Generally, arylamine monomers used as hole injection layer hosts in solution-processed organic light-emitting diodes do not inherently possess resistance to the solvent of the subsequent process; therefore, arylamine monomer compounds that can be used as hole injection layer hosts in solution-processed organic light-emitting diodes must have a curable group introduced. A thin film fabricated by heat treatment or phototreatment of a composition of a fluorene compound with an amine group, a curing initiator, and a p-doping material according to the present invention provides an organic light-emitting diode with excellent resistance to solvents and excellent current efficiency and device characteristics.

[0211] In addition, when a styrene group or an ethenyl group is bonded to the curable group in the compound of Formula 101 according to one embodiment of the present invention, by introducing a curable group at the 9th carbon position of fluorene where the conjugation with the core structure of fluorene is broken, interference with the thin film interaction between the fluorene bonded to the curable body and the arylamine-based monomer core framework can be reduced, and undesirable effects on the molecular orbitals of this core framework can be minimized, thereby enabling the manufacture of an organic light-emitting device with a longer lifespan.

[0212] In an ink composition according to one embodiment of the present invention, since the thermosetting or photocuring groups included in the compound of Formula 101 form crosslinks by heat or light, the compound of Formula 101 is prevented from being washed away by a solvent when an additional layer is laminated on top of a layer treated with the ink composition, thereby allowing the formed layer to be maintained while simultaneously allowing an additional layer to be laminated on top. Additionally, the chemical resistance of the layer treated with the ink composition to the solvent is increased, and the film retention rate is high. Furthermore, since the compound of Formula 101 is crosslinked between the curing groups within the manufactured layer and is provided in the form of a thin film within an organic light-emitting diode, it has the effect of excellent thermal stability.

[0213] In addition, since the compound of Formula 101 according to one embodiment of the present invention includes an amine structure in its core structure, it can have an energy level and band gap suitable for hole injection, hole transport material, or light-emitting material in an organic light-emitting device. In addition, by controlling the substituent of Formula 1, the energy level and band gap can be finely controlled, and the interfacial characteristics between organic layers can be improved, thereby providing an organic light-emitting device having a low driving voltage and / or high luminous efficiency.

[0214] According to one embodiment of the present invention, R101 to R106 are identical or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0215] According to one embodiment of the present invention, R101 to R106 are identical or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0216] According to one embodiment of the present invention, R101 to R106 are identical or different from each other and are each independently hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0217] According to one embodiment of the present invention, R101 to R106 are identical or different from one another and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted isobutyl group; a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted pentyl group; or a substituted or unsubstituted hexyl group.

[0218] According to one embodiment of the present invention, R101 to R106 are identical or different from one another and are each independently hydrogen; deuterium; a halogen group; a methyl group substituted or unsubstituted with a halogen group; an ethyl group substituted or unsubstituted with a halogen group; a propyl group substituted or unsubstituted with a halogen group; a butyl group substituted or unsubstituted with a halogen group; an isobutyl group substituted or unsubstituted with a halogen group; a tert-butyl group substituted or unsubstituted with a halogen group; a pentyl group substituted or unsubstituted with a halogen group; or a hexyl group substituted or unsubstituted with a halogen group.

[0219] According to one embodiment of the present invention, R101 to R106 are identical or different from one another and are each independently hydrogen; deuterium; fluorine; a methyl group substituted or unsubstituted with fluorine; an ethyl group; a propyl group; a butyl group; an isobutyl group; a tert-butyl group; a pentyl group; or a hexyl group.

[0220] According to one embodiment of the present invention, R101 and R104 are identical or different from each other and are each independently hydrogen; deuterium; fluorine; a methyl group substituted or unsubstituted with fluorine; an ethyl group; a propyl group; a butyl group; an isobutyl group; a tert-butyl group; a pentyl group; or a hexyl group.

[0221] According to one embodiment of the present invention, R102, R103, R105 and R106 are hydrogen.

[0222] According to one embodiment of the present invention, n102, n103, n105, and n106 are each integers from 0 to 2.

[0223] According to one embodiment of the present invention, n102, n103, n105 and n106 are each 0 or 1.

[0224] According to one embodiment of the present invention, n101 and n104 are each integers from 0 to 5.

[0225] According to one embodiment of the present invention, n101 and n104 are each 0, 1, 2 or 5.

[0226] According to one embodiment of the present invention, L101 is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

[0227] According to one embodiment of the present invention, L101 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0228] According to one embodiment of the present invention, L101 may be a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylylene group; a substituted or unsubstituted terphenylylene group; a substituted or unsubstituted fluorenylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted binaphtylene group; or a substituted or unsubstituted naphtylene group, or a group in which two or more of the substituents are connected.

[0229] According to one embodiment of the present invention, the formula 101 is any one of the following formulas 102 to 108.

[0230] [Chemical Formula 102]

[0231]

[0232] [Chemical Formula 103]

[0233]

[0234] [Chemical Formula 104]

[0235]

[0236] [Chemical Formula 105]

[0237]

[0238] [Chemical Formula 106]

[0239]

[0240] [Chemical Formula 107]

[0241]

[0242] [Chemical Formula 108]

[0243]

[0244] In the above chemical formulas 102 to 108,

[0245] The definitions of R101 to R106, n101 to n106, m101, m102, Ar101, Ar102, X101, and X102 are as in Chemical Formula 1 above, and

[0246] R101' to R121' are identical or different from one another, and each independently is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and

[0247] s1' to s5', s8', s16' and s19' are each integers from 0 to 4, and

[0248] s6', s7', and s9' are each integers from 0 to 6, and

[0249] s12', s13', s17', and s18' are each integers from 0 to 3, and

[0250] s20' and s21' are integers from 0 to 7, respectively, and

[0251] If s1' to s9', s12', s13' and s16' to s21' are each 2 or more, the substituents in parentheses are identical or different from each other.

[0252] According to one embodiment of the present invention, R101' to R121' are identical or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0253] According to one embodiment of the present invention, R101' to R121' are identical or different from each other and are each independently hydrogen; deuterium; a halogen group; an alkyl group having 1 to 20 carbon atoms; or an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.

[0254] According to one embodiment of the present invention, R101' to R121' are identical or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted t-butyl group; a substituted or unsubstituted pentyl group; a substituted or unsubstituted hexyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0255] According to one embodiment of the present invention, R101' to R121' are identical or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted t-butyl group; a substituted or unsubstituted pentyl group; a substituted or unsubstituted hexyl group; one or more substituted or unsubstituted phenyl groups selected from the group consisting of methyl group, ethyl group, propyl group, butyl group, t-butyl group, pentyl group, and hexyl group; one or more substituted or unsubstituted biphenyl groups selected from the group consisting of methyl group, ethyl group, propyl group, butyl group, t-butyl group, pentyl group, and hexyl group; or one or more substituted or unsubstituted naphthyl groups selected from the group consisting of methyl group, ethyl group, propyl group, butyl group, t-butyl group, pentyl group, and hexyl group.

[0256] According to one embodiment of the present invention, R101' to R121' are identical or different from one another and are each independently hydrogen; deuterium; methyl group; ethyl group; propyl group; butyl group; t-butyl group; pentyl group; hexyl group; or a phenyl group substituted or unsubstituted with a methyl group, a butyl group, or a hexyl group.

[0257] According to one embodiment of the present invention, s1' to s9', s12', s13' and s16' to s21' are each 0 or 1.

[0258] According to one embodiment of the present invention, Ar101 and Ar102 are identical or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms.

[0259] According to one embodiment of the present invention, Ar101 and Ar102 are identical or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 40 carbon atoms; or substituted or unsubstituted heteroaryl groups having 2 to 40 carbon atoms.

[0260] According to one embodiment of the present invention, Ar101 and Ar102 are identical or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 30 carbon atoms; or substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms.

[0261] According to one embodiment of the present invention, Ar101 and Ar102 may be any one of the following structures, but are not limited thereto, and the following structures may be further substituted.

[0262]

[0263] In the above structures,

[0264] W is O, S, NRa, CRbRc, or SiRdRe, and

[0265] R31 to R41, Ra, Rb, Rc, Rd, and Re are identical or different from one another, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and

[0266] p1 is an integer from 0 to 7, and

[0267] p2, p4, and p5 are each integers from 0 to 4, and

[0268] p3 and p6 are integers from 0 to 5, respectively, and

[0269] If p1 to p6 are each 2 or more, the substituents in parentheses are identical or different from each other.

[0270] According to one embodiment of the present invention, R39 to R41 are identical or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0271] According to one embodiment of the present invention, R39 to R41 are identical or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0272] According to one embodiment of the present invention, R39 to R41 are identical or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0273] According to one embodiment of the present invention, R39 to R41 are identical or different from each other and are each independently hydrogen.

[0274] According to one embodiment of the present invention, R31 to R38 are identical or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0275] According to one embodiment of the present invention, R31 to R38 are identical or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0276] According to one embodiment of the present invention, R31 to R38 are identical or different from one another and are each independently hydrogen; deuterium; fluorine; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted biphenyl group.

[0277] According to one embodiment of the present invention, R31 to R38 are identical or different from each other and are each independently hydrogen; deuterium; fluorine; methyl group; ethyl group; propyl group; phenyl group; naphthyl group; or biphenyl group.

[0278] According to one embodiment of the present invention, W is O.

[0279] According to one embodiment of the present invention, W is S.

[0280] According to one embodiment of the present invention, W is CRbRc.

[0281] According to one embodiment of the present invention, W is SiRdRe.

[0282] According to one embodiment of the present invention, Rb, Rc, Rd, and Re are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0283] According to one embodiment of the present invention, Rb, Rc, Rd, and Re are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0284] According to one embodiment of the present invention, Rb, Rc, Rd, and Re are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0285] According to one embodiment of the present invention, Rb, Rc, Rd and Re are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; or a substituted or unsubstituted phenyl group.

[0286] According to one embodiment of the present invention, Rb, Rc, Rd, and Re are the same or different from each other and are each independently hydrogen; deuterium; methyl group; ethyl group; or phenyl group.

[0287] According to one embodiment of the present invention, Ar101 and Ar102 are identical or different from each other and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; and a substituted or unsubstituted fluorenyl group.

[0288] According to one embodiment of the present invention, Ar101 and Ar102 are identical or different from each other and are each independently a phenyl group substituted or unsubstituted with a deuterium or alkyl group; a biphenyl group substituted or unsubstituted with a deuterium or alkyl group; a naphthyl group substituted or unsubstituted with a deuterium or alkyl group; and a fluorenyl group substituted or unsubstituted with a deuterium or alkyl group.

[0289] According to one embodiment of the present invention, Ar101 and Ar102 are identical or different from each other and are each independently a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group; and a fluorenyl group substituted with a methyl group.

[0290] According to one embodiment of the present invention, m1 and m2 are 0 or 1.

[0291] When the above m1 is 0, the 9th carbon of fluorene and X101 are directly bonded, and the specific structure is as follows.

[0292]

[0293] When the above m2 is 0, the 9th carbon of fluorene and X102 are directly bonded, and the specific structure is as follows.

[0294]

[0295] According to one embodiment of the present invention, L101 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and Ar101 and Ar102 are identical or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0296] According to one embodiment of the present invention, the chemical formula 101 is any one selected from the group of compounds 101 consisting of the following compounds.

[0297] [Compound Group 101]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309] .

[0310] The following is information regarding hole injection layer dopants.

[0311] According to one embodiment of the present invention, the aforementioned second compound is a hole injection layer dopant.

[0312] According to one embodiment of the present invention, the second compound is represented by the following chemical formula 201 or the following chemical formula 301.

[0313] [Chemical Formula 201]

[0314]

[0315] In the above chemical formula 201,

[0316] Ar201 to Ar204 are the same or different from each other, at least one of Ar201 to Ar204 is represented by the following chemical formula 202, and the remaining Ar201 to Ar204 are represented by the following chemical formula 203, and

[0317] [Chemical Formula 202]

[0318]

[0319] In the above chemical formula 202,

[0320] At least one of R201 to R205 is F; a cyano group; or a substituted or unsubstituted fluoroalkyl group, and

[0321] At least one of the remaining R201 to R205 is a curable group, and

[0322] The remaining R201 to R205 are the same or different from one another and are each independently hydrogen; deuterium; nitro group; -C(O)R200'; -OR201'; -SR202'; -SO3R203'; -COOR204'; -OC(O)R205'; -C(O)NR206'R207'; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group,

[0323] R200' to R207' are the same or different from one another, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group, and

[0324] [Chemical Formula 203]

[0325]

[0326] In the above chemical formula 203,

[0327] At least one of R206 to R210 is a curable group, and

[0328] The remaining R206 to R210 are the same or different from one another and are each independently hydrogen; deuterium; a nitro group; -C(O)R200'; -OR201'; -SR202'; -SO3R203'; -COOR204'; -OC(O)R205'; -C(O)NR206'R207'; a substituted or unsubstituted alkyl group; a substituted or unsubstituted fluoroalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and R200' to R207' are the same or different from one another and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group, and

[0329] [Chemical Formula 301]

[0330]

[0331] In the above chemical formula 301,

[0332] Ar'201 to Ar'204 are identical or different from each other, and at least one of Ar'201 to Ar'204 is an aryl group having 6 to 30 carbon atoms substituted with a vinyl group, and the remaining Ar'201 to Ar'204 are aryl groups having 6 to 30 carbon atoms substituted with a halogen group.

[0333] According to one embodiment of the present invention, if the second compound, i.e., the ionic compound, specifically the anionic compound, does not have a curable group, curing does not occur, and thus the characteristics of the device are reduced due to the movement of the cation and anion groups of the present invention between the electrode layers.

[0334] According to one embodiment of the present invention, Ar201 is represented by the formula 202, and Ar202 to Ar204 are represented by the formula 203.

[0335] According to one embodiment of the present invention, Ar201 and Ar202 are represented by the formula 202, and Ar203 and Ar204 are represented by the formula 203.

[0336] According to one embodiment of the present invention, Ar201 to Ar203 are represented by the chemical formula 202, and Ar204 is represented by the chemical formula 203.

[0337] According to one embodiment of the present invention, Ar201 to Ar204 are represented by the chemical formula 202. In particular, when Ar201 to Ar204 are all of chemical formula 202, if the proportion of F, cyano groups, or fluoroalkyl groups in the molecule increases, the film retention rate is improved during heat treatment.

[0338] According to one embodiment of the present invention, the ionic compound containing the anionic group can be used in the hole injection layer of an organic light-emitting diode, and when used in the hole injection layer, it can be used as a dopant. At this time, if the content of F of the anionic group increases, the force of attracting electrons from other compounds (host compounds) increases, and holes are generated more easily in the host, thereby improving the performance of the hole injection layer.

[0339] According to one embodiment of the present invention, the content of F can be analyzed using a COSA AQF-100 combustion furnace coupled to a Dionex ICS 2000 ion-chromatograph or confirmed through 19F NMR, which is a method generally used for F analysis.

[0340] According to one embodiment of the present invention, the formula 202 is represented by any one of the following formulas 202-1 to 202-10.

[0341] [Chemical Formula 202-1]

[0342]

[0343] [Chemical Formula 202-2]

[0344]

[0345] [Chemical Formula 202-3]

[0346]

[0347] [Chemical Formula 202-4]

[0348]

[0349] [Chemical Formula 202-5]

[0350]

[0351] [Chemical Formula 202-6]

[0352]

[0353] [Chemical Formula 202-7]

[0354]

[0355] [Chemical Formula 202-8]

[0356]

[0357] [Chemical Formula 202-9]

[0358]

[0359] [Chemical Formula 202-10]

[0360]

[0361] According to one embodiment of the present invention, the formula 203 is represented by any one of the following formulas 203-1 to 203-8.

[0362] [Chemical Formula 203-1]

[0363]

[0364] [Chemical Formula 203-2]

[0365]

[0366] [Chemical Formula 203-3]

[0367]

[0368] [Chemical Formula 203-4]

[0369]

[0370] [Chemical Formula 203-5]

[0371]

[0372] [Chemical Formula 203-6]

[0373]

[0374] [Chemical Formula 203-7]

[0375]

[0376] [Chemical Formula 203-8]

[0377]

[0378] According to one embodiment of the present invention, Ar'201 to Ar'204 are identical or different from each other, and at least one of Ar'201 to Ar'204 is an aryl group having 6 to 30 carbon atoms substituted with a vinyl group, and the remaining Ar'201 to Ar'204 are aryl groups having 6 to 30 carbon atoms substituted with a halogen group.

[0379] According to one embodiment of the present invention, Ar'201 to Ar'204 are identical or different from each other, and at least one of Ar'201 to Ar'204 is an aryl group having 6 to 20 carbon atoms substituted with a vinyl group, and the remaining Ar'201 to Ar'204 are aryl groups having 6 to 20 carbon atoms substituted with a halogen group.

[0380] According to one embodiment of the present invention, Ar'201 to Ar'204 are identical or different from each other, and at least one of Ar'201 to Ar'204 is an aryl group having 6 to 12 carbon atoms substituted with a vinyl group, and the remaining Ar'201 to Ar'204 are aryl groups having 6 to 12 carbon atoms substituted with a halogen group.

[0381] According to one embodiment of the present invention, Ar'201 to Ar'204 are identical or different from each other, and at least one of Ar'201 to Ar'204 is a phenyl group substituted with a vinyl group, and the remaining Ar'201 to Ar'204 are phenyl groups substituted with a halogen group.

[0382] According to one embodiment of the present invention, Ar'201 to Ar'204 are identical or different from each other, and at least one of Ar'201 to Ar'204 is a phenyl group substituted with a vinyl group, and the remaining Ar'201 to Ar'204 are phenyl groups substituted with a fluoro group.

[0383] According to one embodiment of the present invention, any one of Ar'201 to Ar'204 is a phenyl group substituted with a vinyl group, and the remaining Ar'201 to Ar'204 are phenyl groups substituted with a fluoro group.

[0384] According to one embodiment of the present invention, any one of Ar'201 to Ar'204 is a phenyl group substituted with a vinyl group, and the remaining Ar'201 to Ar'204 are pentafluorophenyl groups.

[0385] According to one embodiment of the present invention, the second compound is any one selected from the following structural formulas.

[0386]

[0387]

[0388]

[0389]

[0390] In the above structural formula, r is an integer from 1 to 4, q is an integer from 0 to 3, and q+r=4.

[0391] According to one embodiment of the present invention, the ionic compound comprises a cation group, and the cation group is selected from a monovalent cation group, an onium compound, or the following structural formulas.

[0392] According to one embodiment of the present invention, the monovalent cation group may be an alkali metal cation, and the alkali metal cation is Na + , Li + , K + There are, but are not limited to, the following.

[0393] According to one embodiment of the present invention, the ionic compound comprises a cation group, and the cation group is selected from an onium compound or the following structural formulas.

[0394]

[0395] In the above structural formula, X1 to X 76 are the same or different from one another, and each independently hydrogen; cyano group; nitro group; halogen group; -COOR 104; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted fluoroalkyl group; or substituted or unsubstituted aryl group, or a curable group selected from the above curable group group, and

[0396] R 104 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group, and

[0397] p is an integer from 0 to 10, and

[0398] a is 1 or 2, b is 0 or 1, and a+b=2.

[0399] According to one embodiment of the present invention, the cation group is represented by any one of the following chemical formulas A10 to A15.

[0400] [Chemical Formula A10]

[0401]

[0402] [Chemical Formula A11]

[0403]

[0404] [Chemical Formula A12]

[0405]

[0406] [Chemical Formula A13]

[0407]

[0408] [Chemical Formula A14]

[0409]

[0410] [Chemical Formula A15]

[0411]

[0412] In the above chemical formulas A10 to A15,

[0413] X 100 To X 142 Same or different from one another, and each independently hydrogen; cyano group; nitro group; halogen group; -COOR 105; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted fluoroalkyl group; or substituted or unsubstituted aryl group, or a curable group selected from the above curable group group, and

[0414] The above R 105 is a substituted or unsubstituted alkyl group.

[0415] According to one embodiment of the present invention, the cation group is any one selected from the following structural formulas.

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422] According to one embodiment of the present invention, the ionic compound is selected from the following structural formulas.

[0423]

[0424]

[0425]

[0426]

[0427]

[0428] [Chemical Formula 1-6-1]

[0429]

[0430] The following is information regarding the ink composition.

[0431] According to one embodiment of the present invention, the above-described ink composition further comprises one or more solvents.

[0432] According to one embodiment of the present invention, the one or more solvents are 3,4-dimethylanisole, 4-propyl cyclohexanone, 1,2-dimethoxybenzene, butanedioic acid ethyl methyl ester, propanoic acid phenyl ester, pentanedioic acid dimethyl ester, 1-phenyl-2-propanone, m-dimethoxybenzene, 1-phenyl-1,2-propanedione, 2-methoxyethyl benzoate, 4-(methoxymethyl) Anisole (4-(methoxymethyl) anisole), 2,5-dimethyl benzoate, Benzyl isobutyrate, Phenyl butanoate, Tert-butyl benzoate, 4-phenyl-2-butanone, P-tolyl isobutyrate, 1-methyl naphthalene, 2-ethoxyethyl benzoate, 1-phenyl-1-pentanone, 2-methoxy-1-phenylethanone, 2-methoxyethyl-4-methylbenzoate, phenyl pentanoate, propyl-4-methyl benzoate, phenylethyl isobutyrate,Ethyl-2-ethoxybenzoate, 3-phenyl propyl isobutyrate, Ethyl 3-methoxy benzoate, Ethyl 2-methoxy benzoate, Amyl benzoate, Ethyl 3,5-dimethyl benzoate, Isobutyl salicylate, 1,7-dimethyl naphthalene, 1,3-dimethyl naphthalene, 1,4-dimethyl naphthalene, Ethyl 3-ethoxy Benzoate (Ethyl 3-ethoxy benzoate), 1,6-dimethyl naphthalene, P-tolyl isovalerate, Ethyl 2-(2-oxocyclohexyl) acetate, 1,2-dimethyl naphthalene, Methyl 4-ethoxy benzoate, Butyl p-toluate, 4-isobutyl acetophenone, Methyl 2-isopropoxy benzoate, 4-ethylphenyl butyrate, Ethyl phenethyl Carboate (Ethyl phenethyl carbonate), Ethyl 3-methoxyphenyl acetate, Ethyl 2-methyl-2-phenoxypropanoate, Ethyl 2-acetoxybenzoate, 1,1-Diphenylethane, 2-tert-butyl-4-methylphenyl acetate, 1-(4-methoxy-3-methylphenyl) ethanone, methyl 3-methyl benzofuran-2-carboxylate, ethyl 4-isopropylphenyl acetate, 1-(4-butylphenyl)-ethanone, cyclopentyl benzoate, 1-benzyl-3-methyl benzene, ethyllaitone, (4-methoxyphenyl) butanoate phenyl)butanoate), Acetyl isodurene, 2-(2-methoxyphenyl)-4,5-dimethyl-1,3-dioxolane, 2-methoxyethyl phenyl acetate, Methyl 3-(benzyloxy)propanoate, Ethyl 2-(benzyloxy)acetate, 4-methyl diphenyl methane, 1-(4-isobutylphenyl)propan-1-one, Ethyl 3-phenyl propyl carbonate, 1-(4-propoxy 1-(4-propoxyphenyl) ethanone, ethyl 3-(4-methoxyphenyl) propanoate, 5-undecanolide,It is one or more selected from the group consisting of 4-pentyl acetophenone, ethyl ethoxy (phenyl) acetate, 2-methyl-2-phenyl cyclohexanone, 4-ethoxyphenethyl acetate, 2-pentyloxy acetophenone, 4-methoxy diphenyl methane, ethyl 4-phenoxy butanoate, and benzylbenzoate. However, it is not limited to the above examples.

[0433] According to one embodiment of the present invention, the one or more solvents comprise a plurality of solvents. In a specific example, the plurality of solvents comprises a first solvent and a second solvent. However, the above example is not limited to additional solvents.

[0434] According to one embodiment of the present invention, the vapor pressure of the first solvent has a value greater than the vapor pressure of the second solvent. In other words, the plurality of solvents includes two types of solvents, and among the two types of solvents, the solvent having a greater vapor pressure under conditions of 25°C and / or 1 atm is called the first solvent, and the remaining solvent is called the second solvent. The conditions of 25°C and / or 1 atm described above can be appropriately changed to conditions required for the manufacturing process of an organic light-emitting device, and even if the conditions of 25°C and / or 1 atm are appropriately changed to conditions required for the manufacturing process of an organic light-emitting device, the relationship of vapor pressure between the discoloration control agent, the first solvent, and the second solvent described below can be applied to the relationship of vapor pressure described below.

[0435] According to one embodiment of the present invention, the vapor pressure of the discoloration control agent has a value greater than the vapor pressure of the first solvent.

[0436] According to one embodiment of the present invention, the vapor pressure of the discoloration control agent has a value greater than the vapor pressure of the second solvent.

[0437] According to one embodiment of the present invention, the one or more solvents include a first solvent and a second solvent, the vapor pressure of the first solvent has a value greater than the vapor pressure of the second solvent, and the vapor pressure of the discoloration control agent has a value greater than the vapor pressure of the first solvent.

[0438] According to one embodiment of the present invention, the hole injection layer host is included in an amount of 0.01% to 10% by weight or 0.1% to 5% by weight based on 100% by weight of the ink composition.

[0439] According to one embodiment of the present invention, the hole injection layer dopant is included in an amount of 0.01% to 10% by weight or 0.1% to 5% by weight based on 100% by weight of the ink composition.

[0440] According to one embodiment of the present invention, the discoloration inhibitor is included in an amount of 50% to 80% by weight or 60% to 70% by weight based on 100% by weight of the ink composition.

[0441] According to one embodiment of the present invention, the discoloration inhibitor is included in an amount of 10% to 90% by weight; or 20% to 80% by weight, based on the total weight of the discoloration inhibitor and the solvent.

[0442] According to one embodiment of the present invention, the ink composition may be in a liquid state. The term "liquid state" means being in a liquid state at room temperature and pressure.

[0443] According to one embodiment of the present invention, the ink composition is an ink composition for an organic light-emitting diode.

[0444] According to one embodiment of the present invention, the concentration of the ink composition is 0.5 wt / v% to 10 wt / v%, preferably 1.0 wt / v% to 5.0 wt / v%, but is not limited thereto.

[0445] According to one embodiment of the present invention, the ink composition may further include one or more additives selected from the group consisting of thermal polymerization initiators and photopolymerization initiators.

[0446] As the above thermal polymerization initiator, methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, methylcyclohexanone peroxide, cyclohexanone peroxide, isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide, bis-3,5,5-trimethylhexanoyl peroxide, lauryl peroxide, benzoyl peroxide, p-chlor benzoyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-(t-butyl oxy)-hexane, 1,3-bis(t-butyl peroxy-isopropyl)benzene, t-butyl cumyl peroxide, di-t-butyl peroxide, 2,5-dimethyl-2,5-(dit-butyl peroxy)hexane-3, tris-(t-butyl peroxy) Peroxides such as triazines, 1,1-dit-butyl peroxy-3,3,5-trimethylcyclohexane, 1,1-dit-butyl peroxycyclohexane, 2,2-di(t-butyl peroxy)butane, 4,4-di-t-butylperoxyvaleric acid n-butyl ester, 2,2-bis(4,4-t-butyl peroxycyclohexyl)propane, t-butyl peroxyisobutylate, dit-butyl peroxyhexahydroterephthalate, t-butyl peroxy-3,5,5-trimethylhexaate, t-butyl peroxybenzoate, dit-butyl peroxytrimethyl adipate, or azo compounds such as azobis isobutylnitrile, azobis dimethylvaleronitrile, and azobis cyclohexyl nitrile, but are not limited thereto. does not.

[0447] As the above photopolymerization initiator, an acetophenone-based or ketal-based photopolymerization initiator such as diethoxyacetophenone, 2,2-dimethoxy-1,2-diphenyl ethane-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone-1,2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-methyl-2-morpholino(4-methylthiophenyl)propan-1-one, 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl)oxime; Examples include benzoin ether-based photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isomethyl ether, benzoin isopropyl ether, etc.; benzophenone-based photopolymerization initiators such as benzophenone, 4-hydroxybenzophenone, 2-benzoyl naphthalene, 4-benzoyl biphenyl, 4-benzoyl phenyl ether, acrylated benzophenone, 1,4-benzoyl benzene, etc.; and thioxantone-based photopolymerization initiators such as 2-isopropylthioxantone, 2-chlorothioxantone, 2,4-dimethylthioxantone, 2,4-diethylthioxantone, 2,4-dichlorothioxantone, etc. Other photopolymerization initiators include ethyl anthraquinone, 2,4,6-trimethylbenzoyl diphenyl phosphine oxide, 2,4,6-trimethylbenzoyl phenyl ethoxyphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenyl phosphine oxide, bis(2,4-dimethoxybenzoyl)-2,4,4-trimethyl pentylphosphine oxide, methylphenir glycyester, 9,10-phenanthrene, acridine compounds, triazine compounds, imidazole compounds, etc.

[0448] In addition, substances having a photopolymerization promoting effect may be used alone or in combination with the above-mentioned photopolymerization initiator. For example, substances having a photopolymerization promoting effect include triethanolamine, methyl diethanolamine, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, ethyl (2-dimethylamino)benzoate, 4,4'-dimethylaminobenzophenone, etc., but are not limited thereto.

[0449] According to one embodiment of the present invention, when the change in redness is measured using a PANTONE X-rite Ci7600 under conditions of 25°C and 1 atmosphere, the change in redness of the ink composition is within the range of 0 to 10; 1 to 10; or 2 to 9.9. At this time, the redness may be measured as the value of a*, which represents the red-green index in an L*a*b* colorimeter (L*a*b* Color Space). Furthermore, the conditions of 25°C and 1 atmosphere among the measurement conditions may be appropriately modified by a person skilled in the art. In addition, the above is not limited to the Pantone X-rite Ci7600 colorimeter.

[0450] According to one embodiment of the present invention, the redness has a value within the range of a rated luminous flux of the light source of 3000 lm to 6000 lm; or 4000 lm to 5000 lm. For example, the light source may be white light, but is not limited thereto.

[0451] According to one embodiment of the present invention, the redness refers to a value measured when the measurement target is exposed to a light source at a distance of about 1 m to 4 m; or within the range of 2 m to 3 m. However, the measurement conditions may be appropriately modified by a person skilled in the art.

[0452] According to one embodiment of the present invention, the redness refers to a value measured when the subject to measurement is exposed to the light source for a time condition within the range of 18 to 22 hours; a time condition within the range of 19 to 20 hours; or for 20 hours. However, the measurement conditions may be appropriately modified by a person skilled in the art. For example, the redness of the ink composition is measured using a colorimeter when the ink composition is exposed to white light for a time condition within the range of 18 to 22 hours; a time condition within the range of 19 to 20 hours; or for 20 hours.

[0453] One embodiment of the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise the aforementioned ink composition or a cured product thereof.

[0454] According to one embodiment of the present invention, when the change in redness is measured with a PANTONE X-rite Ci7600 under conditions of 25°C and 1 atmosphere, the change in redness of the organic layer containing the ink composition or the cured product thereof is within the range of 0 to 10; 1 to 10; or 2 to 9.9.

[0455] According to one embodiment of the present invention, an organic layer comprising the aforementioned ink composition or a cured product thereof is a light-emitting layer.

[0456] According to another embodiment of the present invention, the organic light-emitting element comprises two or more organic layers, and the two or more organic layers comprise the aforementioned ink composition or a cured product thereof. For example, one of the two or more organic layers comprises the aforementioned ink composition or a cured product thereof, and further comprises one or more remaining organic layers. According to one embodiment, the remaining one or more organic layers do not comprise the aforementioned ink composition or a cured product thereof. According to another embodiment, the remaining one or more organic layers further comprise the aforementioned ink composition or a cured product thereof. However, the invention is not limited to the above examples.

[0457] The above two or more organic layers comprise, for example, two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, etc. In this case, the hole injection and transport layer refers to a layer that performs hole injection and hole transport simultaneously, and the electron injection and transport layer refers to a layer that performs electron injection and electron transport simultaneously. However, the organic layers forming the above group are merely examples and are not limited to the above examples. Additionally, the above two or more organic layers may include two or more layers that perform the same function as needed. An organic light-emitting device according to one example includes a first hole injection layer and a second hole injection layer. However, it is not limited to the above examples.

[0458] According to one embodiment of the present invention, the organic layer comprises a light-emitting layer. As an example, the light-emitting layer comprises the aforementioned ink composition or a cured product thereof.

[0459] According to one embodiment of the present invention, the organic layer comprises a hole injection and transport layer, a hole injection layer, or a hole transport layer. As an example, the hole injection and transport layer, the hole injection layer, or the hole transport layer comprises the aforementioned ink composition or a cured product thereof.

[0460] According to one embodiment of the present invention, the organic layer comprises a hole injection layer. As an example, the hole injection layer comprises the aforementioned ink composition or a cured product thereof.

[0461] According to one embodiment of the present invention, the organic layer comprising the ink composition or the cured product thereof is a hole transport layer, a hole injection layer, or a layer that simultaneously transports and injects holes.

[0462] According to one embodiment of the present invention, the organic layer further comprises one or more layers selected from the group consisting of an electron blocking layer, 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 group consisting of the electron blocking layer, the hole blocking layer, the electron transport layer, the electron injection layer, and the electron injection and transport layer comprise the aforementioned ink composition or a cured product thereof. As another example, one or more layers selected from the group consisting of the electron blocking layer, the hole blocking layer, the electron transport layer, the electron injection layer, and the electron injection and transport layer do not comprise the aforementioned ink composition or a cured product thereof.

[0463] One embodiment of the present invention comprises a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, and

[0464] The above organic layer includes a light-emitting layer and a hole injection layer, and

[0465] The above-described hole injection layer provides an organic light-emitting device comprising the aforementioned ink composition or a cured product thereof.

[0466] Below, the stacked structure of the organic layer and the organic light-emitting device containing it is specifically described.

[0467] According to one embodiment of the present invention, the organic layer of the organic light-emitting device has a single-layer structure. For example, the single-layer organic layer is provided between the first electrode and the second electrode of the organic light-emitting device, and the organic layer comprises a compound of Formula 1. According to a specific embodiment, the organic layer formed by the single-layer structure is a light-emitting layer, wherein the light-emitting layer comprises the aforementioned ink composition or a cured product thereof.

[0468] According to another embodiment of the present invention, the organic layer of the organic light-emitting device is a multilayer structure in which two or more organic layers are stacked. For example, the organic layer of the multilayer structure is provided between the first electrode and the second electrode of the organic light-emitting device.

[0469] According to one embodiment of the present invention, the organic layer of the multilayer structure comprises a light-emitting layer and an organic layer other than the light-emitting layer. In one example, the light-emitting layer is provided between a first electrode and a second electrode, and the organic layer other than the light-emitting layer is provided between the first electrode and the light-emitting layer. In another example, the light-emitting layer is provided between the first electrode and the second electrode, and the organic layer other than the light-emitting layer is provided between the light-emitting layer and the second electrode. In yet another example, the light-emitting layer is provided between the first electrode and the second electrode, any one organic layer other than the light-emitting layer is provided between the first electrode and the light-emitting layer, and any other organic layer other than the light-emitting layer is provided between the light-emitting layer and the second electrode. However, the above structure is merely an example and is not limited to the above structure. In addition, the organic layer other than the above-mentioned light-emitting layer may be one or more layers selected from the group consisting of, for example, a hole injection and transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, but is not limited thereto.

[0470] Generally, in organic light-emitting diodes, a hole injection layer, a hole transport layer, or an electron blocking layer is provided between the anode and the light-emitting layer. As a specific example, the hole injection layer is provided above the anode, the hole transport layer is provided above the hole injection layer, and the electron blocking layer is provided above the hole injection layer, but is not limited to the above example.

[0471] In addition, generally, in organic light-emitting diodes, an electron injection layer, an electron transport layer, or a hole blocking layer is provided between the cathode and the light-emitting layer. As a specific example, the hole blocking layer is provided on top of the light-emitting layer, the electron transport layer is provided on top of the hole blocking layer, and the electron injection layer is provided on top of the electron transport layer, but is not limited to the above example.

[0472] An organic material layer having a multilayer structure included in an organic light-emitting device according to one embodiment of the present invention comprises: one or more layers selected from the group consisting of a hole injection and transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer; and a light-emitting layer, wherein the light-emitting layer is provided between a first electrode and a second electrode, the first electrode is provided between the first electrode and the light-emitting layer, and the one or more layers comprise a compound of Formula 1.

[0473] The structure of an organic light-emitting device according to one embodiment of the present invention is illustrated in FIG. 1. FIG. 1 illustrates the structure of an organic light-emitting device in which a first electrode (201), a hole injection layer (301), a hole transport layer (401), a light-emitting layer (501), an electron transport and injection layer (601), and a second electrode (701) are sequentially stacked on a substrate (101). The hole injection layer (301) and / or the hole transport layer (401) of FIG. 1 may comprise the aforementioned ink composition or a cured product thereof, or may be formed using the aforementioned ink composition or a cured product thereof. In this case, the fact that the hole injection layer (301) and / or the hole transport layer (401) of FIG. 1 may be formed using the aforementioned ink composition or a cured product thereof will be described later in the specific details of the organic layer, its materials, and manufacturing method. Furthermore, FIG. 1 illustrates an organic light-emitting device according to one embodiment of the present invention and is not limited thereto.

[0474] According to one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.

[0475] According to another embodiment of the present invention, the first electrode is a cathode and the second electrode is an anode.

[0476] As described above, an organic light-emitting device having a single-layer or multi-layer organic layer structure may have a stacked structure such as the following, but is not limited thereto.

[0477] (1) Anode / hole transport layer / emissive layer / cathode

[0478] (2) Anode / hole injection layer / hole transport layer / emissive layer / cathode

[0479] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / cathode

[0480] (4) Anode / hole transport layer / emissive layer / electron transport layer / cathode

[0481] (5) Anode / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0482] (6) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / cathode

[0483] (7) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0484] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / cathode

[0485] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0486] (10) Anode / hole transport layer / electron blocking layer / emissive layer / electron transport layer / cathode

[0487] (11) Anode / hole transport layer / electron blocking layer / emissive layer / electron transport layer / electron injection layer / cathode

[0488] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / emissive layer / electron transport layer / cathode

[0489] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / emissive layer / electron transport layer / electron injection layer / cathode

[0490] (14) Anode / hole transport layer / emissive layer / hole blocking layer / electron transport layer / cathode

[0491] (15) Anode / hole transport layer / emissive layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0492] (16) Anode / hole injection layer / hole transport layer / emissive layer / hole blocking layer / electron transport layer / cathode

[0493] (17) Anode / hole injection layer / hole transport layer / emissive layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0494] (18) Anode / hole injection layer / hole transport layer / emissive layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capsule

[0495] (19) Anode / hole injection layer / first hole transport layer / second hole transport layer / emissive layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capsule

[0496] According to one embodiment of the present invention, the organic light-emitting device may be an organic light-emitting device of a normal type structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0497] According to another embodiment of the present invention, the organic light-emitting device may be an inverted type organic light-emitting device in which a canode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0498] The specific details of the aforementioned organic layer, its materials, and manufacturing methods are described below. However, the organic light-emitting device of the present invention may be manufactured using materials and methods known in the art, except that the organic layer comprises the aforementioned compound.

[0499] An organic light-emitting device according to one embodiment of the present invention is formed such that one or more layers of the organic layer are formed using the aforementioned ink composition or a cured product thereof. Except for this, it can be manufactured using materials and methods known in the art.

[0500] For example, the organic light-emitting device of the present invention can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. In this case, the device can be manufactured by forming an anode 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, and then forming an organic layer containing one or more of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, an electron transport layer, a hole transport and injection layer, and an electron transport and injection layer through a solution process or a deposition process, and then depositing a material that can be used as a cathode on top of it. In addition to this method, an organic light-emitting device can be made by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0501] One embodiment of the present invention also provides a method for manufacturing an organic light-emitting device formed using the aforementioned ink composition or a cured product thereof.

[0502] Specifically, according to one embodiment of the present invention, the method comprises the steps of: preparing a first electrode; forming one or more organic layers on the first electrode; and forming a second electrode on the one or more organic layers, wherein the step of forming one or more organic layers includes forming the organic layers using the aforementioned ink composition or a cured product thereof.

[0503] According to one embodiment of the present invention, the step of forming one or more organic layers using the aforementioned ink composition or a cured product thereof utilizes a spin coating method.

[0504] According to another embodiment of the present invention, the step of forming one or more organic layers using the aforementioned ink composition or a cured product thereof utilizes a printing method.

[0505] According to one embodiment of the present invention, the printing method may be, for example, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing, but is not limited to the printing methods listed above.

[0506] Since the ink composition or the cured product thereof according to one embodiment of the present invention is suitable for a solution process due to its structural characteristics and can be formed by a printing method, there is an economic effect in terms of time and cost during the manufacture of the device.

[0507] According to one embodiment of the present invention, the step of forming one or more organic layers using the aforementioned ink composition or a cured product thereof includes the step of coating the aforementioned ink composition or a cured product thereof; and the step of heat-treating or photo-treating the coated ink composition or a cured product thereof.

[0508] According to one embodiment of the present invention, the step of forming one or more organic layers using the aforementioned ink composition or a cured product thereof comprises: a step of coating the aforementioned ink composition or a cured product thereof on the first electrode or one or more organic layers; and a step of heat treating or phototreating the coated ink composition or a cured product thereof.

[0509] According to one embodiment of the present invention, the heat treatment step may be performed through heat treatment, and the heat treatment temperature in the heat treatment step may be 85 ℃ to 250 ℃, according to one embodiment it may be 100 ℃ to 250 ℃, and in another embodiment it may be 150 ℃ to 250 ℃.

[0510] According to one embodiment of the present invention, the heat treatment time in the heat treatment step is within the range of 10 minutes to 2 hours, according to one embodiment, it may be within the range of 10 minutes to 1 hour, and in another embodiment, it may be within the range of 20 minutes to 1 hour.

[0511] In the step of forming one or more organic layers using the aforementioned ink composition or a cured product thereof, if the heat treatment or phototreatment step is included, a plurality of the compounds included in the aforementioned ink composition may form crosslinks to provide an organic layer having a thin film structure. At this time, when another layer is laminated on the surface of the organic layer formed using the aforementioned ink composition or a cured product thereof, it is possible to prevent dissolution by a solvent, morphological influence, or decomposition.

[0512] Accordingly, when an organic layer formed using the aforementioned ink composition or a cured product thereof is formed including a heat treatment or phototreatment step, its resistance to solvents increases, allowing for the formation of multiple layers by repeatedly performing solution deposition and crosslinking methods, and increasing stability, thereby increasing the lifespan characteristics of the device.

[0513] The materials of the aforementioned anode, cathode, and specific organic layer are described in detail below.

[0514] As for the anode material, a material with a high work function is generally preferred to facilitate hole injection into the organic 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-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0515] The above cathode material is preferably a material with a small work function to facilitate electron injection into an organic 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, but are not limited thereto.

[0516] The light-emitting layer may include a host material and / or a dopant material.

[0517] The above host materials include condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0518] The above dopant materials include aromatic amine derivatives, styramine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and periplantene having arylamine groups. In addition, styramine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, wherein one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamine groups are substituted or unsubstituted. Specifically, styramine, styryldiamine, styryltriamine, styryltetraamine, etc. are examples, but are not limited thereto. In addition, metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0519] The hole injection layer described above is a layer that receives holes from an electrode. It is desirable for the hole injection material to have the ability to transport holes, thereby having an excellent hole receiving effect from the anode and an excellent hole injection effect on the emitting layer or emitting material. In addition, it is desirable for the material to have an excellent ability to prevent the movement of excitons generated in the emitting layer to the electron injection layer or electron injection material. In addition, it is desirable for the material to have an excellent thin film formation ability. Furthermore, it is desirable for the HOMO of the hole injection material to be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic materials; hexanitrile-hexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; and polythiophene-based conductive polymers such as anthraquinone and polyaniline.

[0520] The hole transport layer described above is a layer that receives holes from the hole injection layer and transports holes to the light-emitting layer, and may be a single layer or a multilayer structure of two or more layers. As for the hole transport material, a material capable of receiving holes from an anode or the hole injection layer and transferring them to the light-emitting layer is preferably a material with high mobility for holes.

[0521] The electron transport layer described above is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. As for the electron transport material, a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer is preferred, and a material with high electron mobility is desirable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material, as used in the prior art. In particular, a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically, examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum layer or a silver layer.

[0522] The electron injection layer is a layer that receives electrons from an electrode. As for the electron injection material, it is desirable to have excellent electron transport ability and to have an electron receiving effect from the cathode, and an excellent electron injection effect on the emitting layer or emitting material. In addition, it is desirable to have a material that prevents excitons generated in the emitting layer from moving to the hole injection layer and has excellent thin film formation ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, etc., derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but are not limited thereto. The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, Examples include bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, but are not limited thereto.

[0523] The electron blocking layer is a layer capable of improving the lifespan and efficiency of a device by preventing electrons injected from the electron injection layer from passing through the emitting layer and entering the hole injection layer. The electron blocking layer may be formed between the emitting layer and the hole injection layer, or between the emitting layer and a layer that performs hole injection and hole transport simultaneously, using the compound of Formula 2 described above. Additionally, other known electron blocking materials may be included in addition to the compound of Formula 2 as needed.

[0524] The hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, the hole blocking layer material includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc., but is not limited thereto.

[0525] The above hole injection and transport layers may include the materials of the hole injection layer and hole transport layer described above.

[0526] When the above organic light-emitting element includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0527] The organic light-emitting device according to the present invention may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0528] One embodiment of the present invention provides an electronic device comprising an organic light-emitting element comprising the aforementioned ink composition or a cured product thereof, or an organic layer formed using the ink composition or a cured product thereof.

[0529] The above electronic device may include, but is not limited to, all of the interlayer insulating film of a semiconductor device, a color filter, a black matrix, an overcoat, a column spacer, a passivation film, a buffer coat film, an insulating film for a multilayer printed circuit board, a cover coat of a flexible copper coating plate, a buffer coat film, an insulating film solder resist film for a multilayer printed circuit board, an insulating film of an OLED, a protective film of a thin-film transistor of a liquid crystal display device, a diode for an OLED, an electrode protective film and a semiconductor protective film of an organic EL device, an insulating film of an OLED, an insulating film of an LCD, a insulating film of a semiconductor, a solar module, a touch panel, a display panel, etc.

[0530] Hereinafter, the present invention will be described in detail with reference to examples to specifically explain the invention. However, the embodiments according to the present invention may be modified in various different forms, and the scope of the present invention is not to be interpreted as being limited to the embodiments described below. The embodiments of the present invention are provided to more completely explain the invention to those with average knowledge in the art.

[0532] <Preparation Example>

[0533] Method 1 for synthesizing fluorene with a curable group (FS1-Preparation Examples 1, 2)

[0534]

[0535] A method for attaching a curable group to fluorene is schematically illustrated above. A fluorene cured body can be synthesized by lithiating 1-bromo-4-(diethyoxymethyl)benzene and adding it to fluorenone, followed by a dehydration condensation reaction of tertiary carbinol and arylene in the presence of acid and a Wittig reaction. Fluorene cured bodies F1P and F2P were synthesized by the above method, and specific manufacturing methods for fluorene cured bodies F1P and F2P are shown in Manufacturing Examples 1 and 2 below. The fluorene cured bodies that can be synthesized in this way are not limited to F1P and F2P.

[0537] Preparation Example 1-1. Synthesis of F1P

[0538]

[0539] Synthesis of 4-(2-bromo-9-hydroxy-9H-fluoren-9-yl)benzaldehyde (F1-int1): 1-bromo-4-(diethyoxymethyl)benzene (30 g, 115 mmol) was dissolved in 250 ml of tetrahydrofuran and cooled to -78°C. nBuLi (2.5 M in hexane, 42 ml, 105 mol) was added and stirred at -78°C for 30 minutes. 2-bromo-9H-fluoren-9-one (18.9 g, 73 mmol) was added all at once and stirred overnight. After terminating the reaction with 1N HCl(aq), the solution was extracted with ethyl acetate. The collected organic solution was dried using MgSO4 (magnesium sulfate) and filtered, after which the organic solvent was removed using a vacuum rotary evaporator. The residue was column-purified and recrystallized (toluene / hexane) to obtain 23 g of F1-int1 (yield 87%).

[0540] Synthesis of 4-(2-bromo-9-phenyl-9H-fluoren-9-yl)benzaldehyde [4-(2-bromo-9-phenyl-9H-fluoren-9-yl)benzaldehyde](F1-int2): 400 ml of benzene was added to F1-int1 (11.5 g, 31.4 mmol), followed by the addition of methanesulfonic acid (2.1 ml, 31.4 mmol), and the mixture was refluxed using a Dean-Stark apparatus. After neutralizing the acid with Sat'd NaHCO3(aq), column purification was performed to obtain 6.5 g (yield 49%) of F1-int2.

[0541] Synthesis of 2-bromo-9-phenyl-9-(4-vinylphenyl)-9H-fluorene (F1P): F1-int2 (5.3 g, 12.3 mmol) and CH3BrPPh3 (8.8 g, 24.7 mmol) were added to tetrahydrofuran [THF], and potassium tert-butoxide (2.77 g, 24.7 mmol) was added at 0°C and stirred for 1 hour. The reaction was stopped with water, and the mixture was extracted with ethyl acetate (EA). The collected organic solution was dried by adding magnesium sulfate (MgSO4), filtered, and the organic solvent was removed using a vacuum rotary evaporator. The residue was column-purified to obtain 4.67 g of F1P (yield 89%).

[0543] Preparation Example 1-2. Synthesis of F2P

[0544]

[0545] In the synthesis of F1-int2 of Preparation Example 1, xylene was used instead of benzene, and instead of refluxing using a Dean-Stark apparatus, stirring was performed overnight at 70°C. F2P 6.6g (73% two-step yield) was obtained using F1-int2 (7.3g, 20mmol).

[0547] Preparation Example 1-3. Synthesis of F2PPA

[0548]

[0549] Synthesis of 9-(2,5-dimethylphenyl)-N-phenyl-9-(4-vinylphenyl)-9H-fluoren-2-amine [9-(2,5-dimethylphenyl)-N-phenyl-9-(4-vinylphenyl)-9H-fluoren-2-amine] (F2PPA): Toluene was added to a flask containing F2P (5.55 g, 12.3 mmol), aniline (3.44 g, 36.9 mmol), and sodium tert-butoxide (2.95 g, 30.75 mmol). After placing the flask containing the reaction mixture into a 90°C oil bath, Pd(PtBu3)2 (314 mg, 0.62 mmol) was added and the mixture was stirred for 1 hour. The reaction was stopped by adding water, extracted with dichloromethane (DCM), and the organic layer was dried with MgSO4. After removing the organic solvent using a vacuum rotary evaporator, the residue was column-purified to obtain 5.1 g of F2PPA (yield 90%).

[0551] Preparation Example 2. Preparation of a hole injection layer host

[0552] Preparation Example 2-1. Synthesis of Compound H-2

[0553]

[0554] Synthesis of Compound H-2: Toluene was added to a flask containing F2P (1.37 g, 3.03 mmol), N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (464 mg, 1.38 mmol), and sodium tert-butoxide (769 mg, 8.3 mmol). The flask containing the reactants was placed in a 90°C oil bath, Pd(PtBu3)2 (36 mg, 0.085 mmol) was added, and the mixture was stirred for 1 hour. The reaction was stopped by adding water, extracted with dichloromethane (DCM), and the organic layer was dried with MgSO4. After removing the organic solvent using a vacuum rotary evaporator, the residue was column purified to obtain 500 mg of compound H-2 (yield 34%, HPLC purity 99.8%). The NMR measurements of compound H-2 are shown below.

[0555] 1 H NMR: δ 7.70 (d, 2H), 7.63 (d, 2H), 7.43 (d, 4H), 7.37 (t, 2H), 7.30 - 7.20 (m, 14H), 7.15 - 7.05 (m, 14H), 7.02 (t, 2H), 6.93 (s, 4H), 6.86 (s,2H), 6.71 - 6.65 (dd, 2H), 5.70 (d, 2H), 5.20 (d, 2H), 2.15 (s, 6H), 1.57 (s, 6H).

[0557] Preparation Example 2-2. Synthesis of Compound H-1

[0558] Compound H-1 was synthesized in the same manner as in Preparation Example 2-1 above, except that 9,9-dimethyl-N2,N7-diphenyl-9H-fluorene-2,7-diamine was used instead of N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine.

[0559]

[0561] Preparation Example 2-3. Synthesis of Compound H-3

[0562]

[0563] Synthesis of Compound H-3: Toluene was added to a flask containing F2PPA (2.32 g, 5.0 mmol), 2,2'-dibromo-9,9'-spirobi[fluorene] (948 mg, 2.0 mmol), and sodium tert-butoxide (960 mg, 10.0 mmol). The flask containing the reactants was placed in a 90°C oil bath, Pd(PtBu3)2 (72 mg, 0.14 mmol) was added, and the mixture was stirred for 1 hour. The reaction was stopped by adding water, extracted with dichloromethane (DCM), and the organic layer was dried with MgSO4. After removing the organic solvent using a vacuum rotary evaporator, the residue was column purified to obtain 1.46 g of compound H-3 (yield 59%, HPLC purity 99.2%). The NMR values ​​of compound H-3 are shown below.

[0564] 1 H NMR: δ 7.74 - 7.69 (m, 4H), 7.68 - 7.63 (m, 2H), 7.62 - 7.56 (m, 2H), 7.39 (td, 2H), 7.33 (ddddd, 4H), 7.26 (tdd, 6H), 7.19 - 7.04 (m, 12H), 7.04 - 6.90 (m, 14H), 6.85 (d, 2H), 6.76 - 6.68 (m, 4H), 6.65 - 6.55 (m, 2H), 5.78 - 5.70 (m, 2H), 5.25 (dq, 2H), 2.16 (s, 6H), 1.57 (s, 6H).

[0566] Preparation Example 2-4. Synthesis of Compound H-4

[0567]

[0568] Synthesis of Compound H-4: Toluene was added to a flask containing F1P (1.58 g, 3.74 mmol), N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (572 mg, 1.7 mmol), and sodium tert-butoxide (980 mg, 10.2 mmol). The flask containing the reactants was placed in a 90°C oil bath, Pd(PtBu3)2 (43 mg, 0.085 mmol) was added, and the mixture was stirred for 1 hour. The reaction was stopped by adding water, extracted with dichloromethane (DCM), and the organic layer was dried with MgSO4. After removing the organic solvent using a vacuum rotary evaporator, the residue was column purified to obtain 950 mg of compound H-4 (yield 55%, HPLC purity 99.5%). The NMR measurements of compound H-4 are shown below.

[0569] 1 H NMR: δ 7.71 (d, 2H), 7.65 (d, 2H), 7.42 (d, 4H), 7.35 (d, 4H), 7.27 - 7.20 (m, 18H), 7.17 - 7.13 (m, 4H), 7.11 - 7.06 (m, 14H), 7.03 (t, 2H), 6.70 - 6.64 (dd, 2H), 5.69 (d, 2H), 5.19 (d, 2H).

[0571] Preparation Example 2-5. Synthesis of Compound H-5

[0572] Compound H-5 was synthesized in the same manner as in Preparation Examples 2-4 above, except that N4,N4'-diphenyl-[1,1'-binaphthalene]-4,4'-diamine was used instead of N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine.

[0573]

[0575] Preparation Example 3. Preparation of hole injection layer dopant

[0576] Preparation Example 3-1. Synthesis of Compound D-1

[0577]

[0578] D-1-1

[0579] Mg (193 mg, 7.9208 mmol), I2 (4 mg), and tetrahydrofuran (THF) (10 mL) were added to a 100 mL round-bottom flask under a nitrogen atmosphere and stirred for 30 minutes. 4-bromostyrene (1.04 mL, 7.9208 mmol) was added, a 30 °C water bath was placed beneath the round-bottom flask, and the mixture was stirred for one day. It was confirmed that the reaction solution turned black and that Mg had dissolved. 5 mL of ether was added to dilute the reaction solution. Tris(pentafluorophenyl)borane (1 g, 3.9604 mmol) was dissolved in 5 mL of ether and slowly added to the reaction solution over 30 minutes. The solution was stirred for one day. Na2CO3 (0.1 M, 80 mL, 8.0 mmol) was slowly added to the reaction solution. The organic solvent was extracted using EA (20 mL x 3), and the residue was removed with MgSO4. Additionally, to remove residual water and impurities, distillation with benzene was performed using a Dean-stock method. When approximately 10 mL of solvent remained, the solution was cooled and filtered to obtain 1.6 g of the target compound D-1-1. (Yield: 64%)

[0580]

[0581] D-1

[0582] Sodium tris(perfluorophenyl)(4-vinylphenyl)borate (100 mg, 0.1567 mmol), 10 mL of distilled water, and pH 2ICl (60 mg, 0.1881 mmol) were added to a 25 mL round-bottom flask and stirred for 1 hour. When 15 mL of acetone was added to the reaction solution, a precipitate formed; this precipitate was filtered and dried to obtain 140 mg of compound D-1. (Yield: 100%)

[0584] Preparation Example 3-2. Synthesis of Compound D-2

[0585]

[0586] D-2-1

[0587] Add methyltriphenyl potassium bromide (13.90 g, 38.9135 mmol) and tetrahydrofuran (THF) (100 mL) to a 250 mL round-bottom flask and 0 o The mixture was stirred at C for 30 minutes. n-BuLi (15.6 mL, 38.9135 mmol, 2.5 M in Hexane) was slowly added to the reaction solution, and the mixture was stirred at 0 °C for 30 minutes. At 0 °C, 4-formyl-2,3,5,6-tetrafluoro-1-bromobenzene (5.0 g, 19.4568 mmol, in 30 mL tetrahydrofuran (THF)) was slowly added to the reaction solution. The reaction solution was stirred while slowly raising the temperature to room temperature. After 3 hours, 100 mL of ether and 400 mL of saturated NH4Cl solution were added to the reaction solution. The organic solvent was extracted using ether (2 x 200 mL), and the residue was removed with MgSO4. By column at EA:Hex = 1:9, 1.29 g of the target compound D-2-1 was obtained. (Yield: 26%)

[0588]

[0589] D-2-2

[0590] Mg (95 mg, 3.9214 mmol), 10 mL of THF, and I2 (4 mg) were added to a 25 mL round-bottom flask and stirred. 1-Bromo-2,3,5,6-tetrafluoro-4-vinylbenzene (1.0 g, 3.9214 mmol) was added to the reaction solution and stirred at room temperature. After 10 hours, when the solution turned black and it was confirmed that the Mg had completely dissolved, 10 mL of ether and BCl3 (1.3 mL, 1.3 mmol, 1 M in hexane solution) were added over 30 minutes. After stirring the reaction solution for one day, Na2CO3 (30 mL, 3.0 mmol, 0.1 M in H2O) was added. The synthetic product was extracted with EA (3 x 10 mL), and the residue was removed with MgSO4. After removing all the solvent, water was completely removed using Dean-stock with benzene, and the solid was filtered to obtain 340 mg of the target compound D-2-2. (Yield: 28%)

[0591]

[0592] Sodium tetrakis(2,3,5,6-tetrafluoro-4-vinylphenyl)borate (501 mg, 0.6823 mmol), diphenyliodonium chloride (216 mg, 0.6823 mmol), 10 mL of H2O, and 10 mL of acetone were added to a 25 mL round-bottom flask and stirred vigorously for 30 minutes. When a precipitate formed, the precipitate was washed with water to obtain 677 mg of target compound D-2. (Yield: 100%)

[0594] <Experimental Example>

[0595] Example 1, and Examples 2 to 17

[0596] In Example 1, the following compound H-1 was used as the hole injection layer host and the following compound D-1 was used as the hole injection layer dopant. A solute obtained by mixing the following compound H-1 and the following compound D-1 in an 8:2 mass ratio was mixed at a mass ratio of 2 wt% in the discoloration inhibitor 2-(2-methoxyethoxy)ethanol listed in Table 1 below, and no additional solvent was included. The mixed solution was stirred for 24 hours to completely dissolve the compounds, and then the solutions were exposed to white light for 20 hours. The degree of discoloration was quantified using a PANTONE X-rite Ci7600 under conditions of 25°C and 1 atm as the a value (Red index), which is the scale standard for red in an L*a*b* colorimeter, and the results are listed in Table 1 below. Examples 2 to 17 were conducted in the same manner as Example 1, except that the materials listed in Table 1 below were used instead of the hole injection layer host, hole injection layer dopant, and discoloration inhibitor of Example 1, and the results are listed in Table 1 below.

[0598] HIL HOST

[0599]

[0600] H-1

[0601]

[0602] H-2

[0603]

[0604] H-3

[0605]

[0606] H-4

[0607]

[0608] H-5

[0610] HIL DOPANT

[0611]

[0612] D-1

[0613]

[0614] D-2

[0616] Experimental Example Examples HIL HOST, HIL DOPANT Discoloration inhibitor Boiling point (°C) Solubility (g / L) Red indicator (a) 0 - - Control group Tetrahydrofuran - - 0.01 24 1 H-1, D-1 2-(2-methoxyethoxy)ethanol 193 1000.0 7.1 25 2 H-1, D-2 2-2-(2-methoxyethoxy)ethoxyethanol 249 1000.0 7.4 26 3 H-2, D-1 Diethyleneglycol monobutyl ether 231 338.0 9.4 27 4 H-2, D-1 2-2-(2-ethoxyethoxy)ethoxyethanol 255.8 1000.0 9.5 28 5 H-2, D-2 Dipropyleneglycol n-butylether 222 94.0 7.5 29 6 H-2, D-2 Tetraethyleneglycol monomethyl ether 278 1000.0 6.7 30 7 H-2, D-2 Tripropylene Glycol Monomethyl Ether 243 1000.0 9.9 31 8 H-2, D-2 Dipropylene Glycol Monomethyl Ether 190 1000.0 8.8 32 9 H-3, D-1 Diethyleneglycol monobenzyl ether 311 148.0 6.2 33 10 H-3, D-2 Triethyleneglycol monobenzyl ether 357 287.0 2.2 34 11 H-3, D-2 2-(Benzyloxy)ethanol 256 72.2 9.1 35 12 H-3, D-2 3-Methoxybenzyl Alcohol 250 19.4 7.2 36 13 H-3, D-2 Diethylene Glycol Dimethyl Ether 162 1000.0 8.4 37 14 H-4, D-1 Triethylene Glycol Dimethyl Ether 216 1000.0 7.8 38 15 H-4, D-2 Tetraethylene Glycol Dimethyl Ether 275 1000.0 7.7 39 16 H-5, D-1 Triethylene Glycol Butyl Methyl Ether 269 164.0 7.9 40 17 H-5, D-2 Diethylene Glycol Butyl Methyl Ether 212 82.7 8.8

[0617] Experimental Examples 24 to 40 above correspond to Examples 1 to 17, respectively.

[0619] Comparative Examples 1 to 23

[0620] In Comparative Examples 1 to 23, experiments were conducted in the same manner as in the above Examples, except that the hole injection layer host, hole injection layer dopant, and other solvents listed in Table 2 below were used instead of the hole injection layer host, hole injection layer dopant, and discoloration inhibitor of the above Examples. The results measured and quantified in Comparative Examples 1 to 23 are listed in Table 2 below.

[0622] Experimental Example Comparative example HIL HOST, HIL DOPANT Other solvents Boiling point (°C) Solubility (g / L) Red indicator (a) 0 - Control group Tetrahydrofuran - - 0.01 1 1 H-1, D-1 Dibutylsuccinate 274 0.07 19.1 2 2 H-1, D-2 Diethylbutylmalonate 240 0.36 12.1 3 3 H-1, D-2 Ethyleneglycoldibutyrate 240 0.69 10.8 4 4 H-2, D-1 Dibutyloxalate 239 0.69 18.1 5 5 H-2, D-1 Hexylacetoacetate 232 1.94 12.8 6 6 H-2, D-1 Diethylene glycol diethyl ether 188 262.00 11.3 7 7 H-2, D-2 Ethylene glycol dibutyl ether 203.3 1.26 18.4 8 8 H-2, D-2 Diethylene Glycol Dibutyl Ether 256 2.51 12.8 9 9 H-2, D-2 Ethylene glycol diethyl ether 121.4 120.00 12.3 10 10 H-2, D-2 3-phenylpropylisobutyrate 252 0.01 14 11 11 H-2, D-2 2-phenylethylisovalerate 268 0.01 18.3 12 12 H-3, D-1 Phenethyl 2-methylbutyrate 230 0.01 14.7 13 13 H-3, D-1 Phenylethylisobutyrate 265 0.04 18.8 14 14 H-3, D-2 Ethyl 4-ethoxybenzoate 275 0.20 18.8 15 15 H-3, D-2 Benzylbutyrate 240 0.08 15.9 16 16 H-3, D-2 2-phenoxyethylacetate 243 0.46 18.7 17 17 H-3, D-2 Ethyl-4-methoxybenzoate 269.5 0.63 17.9 18 18 H-4, D-1 2-phenylethylacetate 232.6 0.27 18 19 19 H-4, D-2 Ethyl p-toluate 235 0.36 13.9 20 20 H-4, D-2 P-anisaldehydedimethylacetal 253 3.94 10.4 21 21 H-5, D-1 Phenylacetaldehyde dimethylacetal 240 2.22 17.2 22 22 H-5, D-1 (4-Methoxybenzyl)Methyl Ether 226 2.00 10.3 23 23 H-5, D-2 Benzyl Methyl Ether 170 3.41 13.9

[0623] Experimental Examples 1 to 23 above correspond to Comparative Examples 1 to 23, respectively.

[0625] From the experimental results of Tables 1 and 2 above, it was confirmed that the ink composition containing a discoloration inhibitor according to one embodiment of the present invention has a much slower rate of discoloration than an ink composition without such inhibitor. This can be confirmed in Figures 2 to 17, which illustrate the change in redness of the ink compositions in the above examples and comparative examples.

[0626] Figures 2 and 3 respectively illustrate the change in redness of the ink composition before and after in Experimental Examples 24 to 31 of the present invention.

[0627] Figures 4 and 5 respectively illustrate the change in redness of the ink composition before and after in Experimental Examples 32 to 35 of the present invention.

[0628] Figures 6 and 7 respectively show the change in redness of the ink composition before and after in Experimental Examples 36 to 40 of the present invention.

[0629] FIGS. 8 and 9 respectively illustrate the change in redness of the ink composition in Experimental Examples 1 to 5 of the present invention.

[0630] FIGS. 10 and 11 respectively illustrate the change in redness of the ink composition in Experimental Examples 6 to 9 of the present invention.

[0631] FIGS. 12 and 13 respectively illustrate the change in redness of the ink composition before and after in Experimental Examples 10 to 19 of the present invention.

[0632] FIGS. 14 and 15 respectively illustrate the change in redness of the ink composition before and after in Experimental Examples 20 to 23 of the present invention.

[0633] From the contents of Tables 1 and 2 above, it was confirmed that an ink composition containing a discoloration inhibitor according to one embodiment of the present invention inhibits discoloration more than an ink composition without such inhibitor. Specifically, when the hole injection layer host and dopant are exposed to light, they form a charge transfer complex by cation initiation to absorb visible light and gradually turn reddish-brown; however, it was confirmed that the speed of discoloration can be controlled by including the discoloration inhibitor according to the present invention.

[0634] Tetrahydrofuran, a colorless organic solvent, was used as a control, and Examples 1 to 17 (corresponding to Experimental Examples 24 to 40, respectively) had smaller Red Index (a) values ​​than Comparative Examples 1 to 23 (corresponding to Experimental Examples 1 to 13, respectively), thereby confirming that the discoloration speed can be controlled by including the discoloration inhibitor according to the present invention. Explanation of the symbols

[0636] 101: Board 201: Anode 301: Hole injection layer 401: Precision Transport Layer 501: Emissive layer 601: Layer that performs electron injection and electron transport simultaneously 701: Cathode

Claims

Claim 1 An ink composition comprising a compound represented by the following chemical formula 101, a second compound, and a discoloration control agent, wherein the discoloration control agent comprises one or more non-covalent electron pairs and is represented by the following chemical formula 1 or the following chemical formula 2, and the second compound is represented by the following chemical formula 201 or the following chemical formula 301: [Chemical Formula 101] In the above chemical formula 101, L101 is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; R101 to R106 are identical or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; and Ar101 and Ar102 are identical or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, X101 and X102 are identical or different from each other and are each independently hardening groups, n101 and n104 are each independently integers from 0 to 5, n102 and n106 are each independently integers from 0 to 4, n103 and n105 are each independently integers from 0 to 3, where n101 to n106 are each 2 or more, the substituents in parentheses are identical or different from each other, m101 and m102 are each 0 or 1, [Chemical Formula 201] In the above Chemical Formula 201, Ar201 to Ar204 are the same or different from each other, at least one of Ar201 to Ar204 is represented by the following Chemical Formula 202, and the remaining Ar201 to Ar204 are represented by the following Chemical Formula 203, [Chemical Formula 202] In the above formula 202, at least one of R201 to R205 is F; a cyano group; or a substituted or unsubstituted fluoroalkyl group, and at least one of the remaining R201 to R205 is a curable group, and the remaining R201 to R205 are the same or different from each other and are each independently hydrogen; deuterium; a nitro group; -C(O)R200'; -OR201'; -SR202'; -SO3R203'; -COOR204'; -OC(O)R205'; -C(O)NR206'R207'; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and R200' to R207' are the same or different from each other and are each independently hydrogen; Deuterium; or a substituted or unsubstituted alkyl group, [Chemical Formula 203] In the above formula 203, at least one of R206 to R210 is a curable group, and the remaining R206 to R210 are the same or different from each other and are each independently hydrogen; deuterium; nitro group; -C(O)R200'; -OR201'; -SR202'; -SO3R203'; -COOR204'; -OC(O)R205'; -C(O)NR206'R207'; substituted or unsubstituted alkyl group; substituted or unsubstituted fluoroalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group, and R200' to R207' are the same or different from each other and are each independently hydrogen; deuterium; or substituted or unsubstituted alkyl group, [Formula 301] In the above Chemical Formula 301, Ar'201 to Ar'204 are identical or different from each other, at least one of Ar'201 to Ar'204 is an aryl group having 6 to 30 carbon atoms substituted with a vinyl group, and the remaining Ar'201 to Ar'204 are aryl groups having 6 to 30 carbon atoms substituted with a halogen group, [Chemical Formula 1] In the above Chemical Formula 1, L1 is a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms; or a substituted or unsubstituted arylalkylene group having 7 to 11 carbon atoms, X1 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and n1 is an integer from 1 to 5, [Chemical Formula 2] In the above formula 2, L2 is a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms, X2 and X3 are identical or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and n2 is an integer from 2 to 8. Claim 2 delete Claim 3 An ink composition according to claim 1, wherein the discoloration control agent is represented by the formula 1, L1 is an alkylene group having 1 to 3 carbon atoms substituted or unsubstituted with a methyl group; or an arylalkylene group having 7 to 11 carbon atoms substituted or unsubstituted with a methyl group; and X1 is an alkyl group having 1 to 4 carbon atoms substituted or unsubstituted with a phenyl group. Claim 4 An ink composition according to claim 1, wherein the discoloration control agent is represented by the chemical formula 1, and the chemical formula 1 is any one selected from the compound group 1 consisting of the following compounds: [Compound group 1] . Claim 5 An ink composition according to claim 1, wherein the discoloration control agent is represented by the formula 2, L2 is an alkylene group having 1 to 3 carbon atoms substituted or unsubstituted with a methyl group, X2 is an alkyl group having 1 to 4 carbon atoms, and X3 is a methyl group. Claim 6 Ink composition according to claim 1, wherein the discoloration control agent is represented by the chemical formula 2, and the chemical formula 2 is any one selected from the compound group 2 consisting of the following compounds: [Compound group 2] . Claim 7 An ink composition according to claim 1, wherein the boiling point of the discoloration control agent is 150 ℃ to 300 ℃. Claim 8 An ink composition according to claim 1, wherein the solubility of the discoloration control agent in water is 12 g / L to 18 g / L under conditions of 25°C and 1 atm. Claim 9 An ink composition according to claim 1, wherein the discoloration control agent is 50% to 80% by weight with respect to 100% by weight of the ink composition. Claim 10 An ink composition according to claim 1, wherein L101 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and Ar101 and Ar102 are identical or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Claim 11 An ink composition according to claim 1, wherein the second compound is any one selected from the following structural formulas: In the above structural formula, r is an integer from 1 to 4, q is an integer from 0 to 3, and q+r=4. Claim 12 An ink composition according to claim 1, wherein the curable group is any one selected from the following structures: In the above structures, Lc is a direct bond; -O-; -S-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, lc1 is 1 or 2, and when lc1 is 2, the Lc are the same or different from each other, and Rc1 is a substituted or unsubstituted alkyl group. Claim 13 An ink composition according to claim 1, further comprising one or more solvents. Claim 14 In claim 13, the one or more solvents are 3,4-dimethylanisole, 4-propylcyclohexanone, 1,2-dimethoxybenzene, ethyl methyl butanedione ester, phenyl ester propanoate, dimethyl pentanedione ester, 1-phenyl-2-propanone, m-dimethoxybenzene, 1-phenyl-1,2-propanedione, 2-methoxyethyl benzoate, 4-(methoxymethyl)anisole, 2,5-dimethyl benzoate, benzyl isobutyrate, phenyl butanoate, tertbutyl benzoate, 4-phenyl-2-butanone, p-tolyl isobutyrate, 1-methyl naphthalene, 2-ethoxyethyl benzoate, 1-phenyl-1-pentanone, 2-methoxy-1-phenylethanolone, 2-Methoxyethyl-4-Methylbenzoate, Phenylpentanoate, Propyl-4-Methylbenzoate, Phenylethyl Isobutyrate, Ethyl 2-Ethoxybenzoate, 3-Phenylpropyl Isobutyrate, Ethyl 3-Methoxybenzoate, Ethyl 2-Methoxybenzoate, Amyl benzoate, Ethyl 3,5-Dimethylbenzoate, Isobutyl salicylate, 1,7-Dimethylnaphthalene, 1,3-Dimethylnaphthalene, 1,4-Dimethylnaphthalene, Ethyl 3-Ethoxybenzoate, 1,6-Dimethylnaphthalene, P-Tolyl Isovalerate, Ethyl 2-(2-Oxocyclohexyl) Acetate), 1,2-Dimethylnaphthalene, Methyl 4-Ethoxy Benzoate, butyl p-toluate, 4-isobutyl acetophenone, methyl 2-isopropoxy benzoate, 4-ethylphenyl butyrate, ethyl phenethyl carboate, ethyl 3-methoxyphenyl acetate, ethyl 2-methyl 2-phenoxypropanoate, ethyl 2-acetoxybenzoate, 1,1-diphenylethane, 2-tertbutyl-4-methylphenyl acetate, 1-(4-methoxy-3-methylphenyl) ethanolone, methyl 3-methyl benzofuran-2-carboxylate, ethyl 4-isopropylphenyl acetate, 1-(4-butylphenyl) ethanolone, cyclopentyl benzoate, 1-benzyl-3-methylbenzene, ethyllytone, (4-methoxyphenyl) butanoate, Acetyl isoduren, 2-(2-methoxyphenyl)-4,5-dimethyl-1,3-dioxolane, 2-methoxyethyl phenyl acetate, methyl 3-(benzyloxy)propaneoate,An ink composition comprising one or more selected from the group consisting of ethyl 2-(benzyloxy)acetate, 4-methyl diphenylmethane, 1-(4-isobutylphenyl)propan-1-one, ethyl 3-phenylpropyl carbonate, 1-(4-propoxyphenyl)ethanolone, ethyl 3-(4-methoxyphenyl)propanoate, 5-undecanolid, 4-pentyl acetophenone, ethyl ethoxy(phenyl)acetate, 2-methyl-2-phenylcyclohexanone, 4-ethoxyphenethyl acetate, 2-pentyloxyacetophenone, 4-methoxydiphenylmethane, ethyl 4-phenoxybutanoate, and benzyl benzoate. Claim 15 An ink composition according to claim 13, wherein one or more solvents comprise a first solvent and a second solvent, the vapor pressure of the first solvent has a value greater than the vapor pressure of the second solvent, and the vapor pressure of the discoloration control agent has a value greater than the vapor pressure of the first solvent. Claim 16 An ink composition according to claim 1, wherein when the change in redness is measured with a PANTONE X-rite Ci7600 under conditions of 25°C and 1 atmosphere, the change in redness of the ink composition is within the range of 0 to 10. Claim 17 An organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise an ink composition according to any one of claims 1 and 3 to 16 or a cured product thereof. Claim 18 An organic light-emitting device according to claim 17, wherein when the change in redness is measured with a PANTONE X-rite Ci7600 under conditions of 25°C and 1 atm, the change in redness of the organic layer containing the ink composition or the cured product thereof is within the range of 0 to 10. Claim 19 An organic light-emitting device according to claim 17, wherein the organic layer comprising the ink composition or the cured product thereof is a hole transport layer, a hole injection layer, or a layer that simultaneously transports and injects holes.

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