KR20240028587A - Ink composition, organic material layer comprising same and organic light emitting device comprising same - Google Patents

Abstract

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

Description

Ink composition, organic material layer containing the same, and organic light-emitting device containing the same {INK COMPOSITION, ORGANIC MATERIAL LAYER COMPRISING SAME AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

This specification relates to an ink composition, an organic material layer containing the same, and an organic light-emitting device containing the same.

The organic luminescence phenomenon is an example of an electric current being converted into visible light by an internal process of a specific organic molecule. The principle of organic luminescence phenomenon is the same as follows. When an organic layer is placed between an anode and a cathode and an electric current is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and anode, respectively. Electrons and holes injected into the organic layer recombine to form excitons, and when these excitons fall back to the ground state, they emit light. Organic light-emitting devices using this principle are generally composed of a cathode, an anode, and an organic material layer located between them, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, an electron transport layer, an electron blocking layer, a hole blocking layer, etc. .

Conventionally, a deposition process has been mainly used to manufacture organic light-emitting devices. However, when manufacturing an organic light-emitting device using a deposition process, there are problems that a lot of material loss occurs and that it is difficult to manufacture a large-area device. To solve these problems, devices using a solution process are being developed.

Therefore, there is a need for development of materials for solution processing.

Korean Patent Publication No. 10-2012-0112277 Korean Patent Publication No. 10-2013-0042364

This specification relates to an ink composition, an organic material layer containing the same, and an organic light-emitting device containing the same.

An exemplary embodiment of the present specification includes a compound represented by the following formula (1); A first solvent represented by the following formula (A); and a second solvent represented by the following formula (B).

[Formula 1]

[Formula A]

[Formula B]

In Formula 1, A and B,

La is a substituted or unsubstituted divalent hydrocarbon ring group; Or a substituted or unsubstituted divalent heterocyclic group,

Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L10 and L11 are the same or different from each other and are each independently a substituted or unsubstituted arylene group,

L20 and L21 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

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

R1 to R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r1 and r2 are each integers from 0 to 7, and when r1 and r2 are each 2 or more, 2 or more substituents in parentheses are the same or different from each other,

r3 and r4 are each integers from 0 to 4, and when r3 and r4 are each 2 or more, 2 or more substituents in parentheses are the same or different from each other,

f1 is the number of bonding positions where substituents can be bonded to 0 to Ar1,

f2 is the number of bonding positions where a substituent can be bonded to 0 to Ar2,

f3 and f4 are each integers from 0 to 5, r3+f3 is 5 or less, r4+f4 is 5 or less, f1+f2+f3+f4 is an integer of 1 or more,

Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; hydroxyl group; ether group; carbonyl group; ester group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted amine group,

L1 and L2 are the same or different from each other and are each independently directly bonded; -O-; Or a substituted or unsubstituted alkylene group,

Z1 and Z2 are the same or different from each other and are each independently a substituted or unsubstituted alkyl group,

a1 is 0 or 1,

l1 and l2 are each integers of 1 to 10, and when l1 and l2 are each 2 or more, 2 or more substituents in parentheses are the same or different from each other.

Another embodiment of the present specification provides a pixel containing the above-described ink composition or a cured product thereof.

Another embodiment of the present specification provides an organic material layer including the above-described pixels.

Another embodiment of the present specification includes a first electrode; second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer is the organic material layer described above.

The ink composition according to an exemplary embodiment of the present specification can be subjected to a solution process or an inkjet process. Accordingly, it is possible to increase the area of the device.

A pixel containing an ink composition or a cured product thereof according to an exemplary embodiment of the present specification has excellent flatness.

The ink composition according to an exemplary embodiment of the present specification can be used as a material for the organic layer of an organic light-emitting device and exhibit low driving voltage, excellent luminous efficiency, and long lifespan characteristics.

Figure 1 illustrates an organic light-emitting device according to an exemplary embodiment of the present specification.
Figure 2 shows a line bank inkjet substrate on which an ink composition according to an exemplary embodiment of the present specification is applied.
Figure 3 shows an ink composition according to an exemplary embodiment of the present specification being applied to a line bank inkjet substrate.
Figure 4 shows an ink composition according to an exemplary embodiment of the present specification formed as a thin film on a line bank inkjet substrate.
Figure 5 is a diagram illustrating the flatness measurement area (A) of a pixel.
Figure 6 is a diagram showing the NMR measurement results of compound DA.
Figure 7 is a diagram showing the NMR measurement results of compound DB.

Hereinafter, the present invention will be described in detail.

An exemplary embodiment of the present specification includes a compound represented by the following formula (1); A first solvent represented by the following formula (A); and a second solvent represented by the following formula (B).

[Formula 1]

[Formula A]

[Formula B]

In Formula 1, A and B,

La is a substituted or unsubstituted divalent hydrocarbon ring group; Or a substituted or unsubstituted divalent heterocyclic group,

Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L10 and L11 are the same or different from each other and are each independently a substituted or unsubstituted arylene group,

L20 and L21 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

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

R1 to R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r1 and r2 are each integers from 0 to 7, and when r1 and r2 are each 2 or more, 2 or more substituents in parentheses are the same or different from each other,

r3 and r4 are each integers from 0 to 4, and when r3 and r4 are each 2 or more, 2 or more substituents in parentheses are the same or different from each other,

f1 is the number of bonding positions where substituents can be bonded to 0 to Ar1,

f2 is the number of bonding positions where a substituent can be bonded to 0 to Ar2,

f3 and f4 are each integers from 0 to 5, r3+f3 is 5 or less, r4+f4 is 5 or less, f1+f2+f3+f4 is an integer of 1 or more,

Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; hydroxyl group; ether group; carbonyl group; ester group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted amine group,

L1 and L2 are the same or different from each other and are each independently directly bonded; -O-; Or a substituted or unsubstituted alkylene group,

Z1 and Z2 are the same or different from each other and are each independently a substituted or unsubstituted alkyl group,

a1 is 0 or 1,

l1 and l2 are each integers of 1 to 10, and when l1 and l2 are each 2 or more, 2 or more substituents in parentheses are the same or different from each other.

The compound represented by Formula 1 according to an exemplary embodiment of the present specification includes two types of substituents with different structures on fluorene, specifically a haloaryl group and other curable groups, thereby inhibiting the formation of radicals at the corresponding position, thereby increasing the stability of the compound. It has a high HOMO (highest occupied molecular orbital) energy level value and excellent hole mobility. For this reason, when the compound represented by Formula 1 is applied to the organic material layer in an organic light-emitting device, the performance and/or stability of the device can be improved. Specifically, when the compound represented by Formula 1 is included in the hole injection layer, there is an advantage in that it is possible to obtain an organic light-emitting device with a long lifespan by facilitating hole injection from the hole injection layer to the hole transport layer.

The first solvent represented by Formula A according to an exemplary embodiment of the present specification contains biphenyl as a parent nucleus structure, and thus has excellent solubility in the aromatic solute contained in the ink composition. In addition, it has the advantage of improving the uniformity of the organic layer by reducing the thickness deviation for each position of each pixel due to the good leveling effect. Specifically, in pixels formed by applying and curing the ink composition, the thickness deviation within a pixel and the thickness deviation between pixels can be reduced. Accordingly, factors affecting the interference conditions of light emitted from the light emitting device depending on the thickness are reduced, and excellent light emission and/or color development effects can be expected.

The second solvent represented by Chemical Formula B according to an exemplary embodiment of the present specification has the effect of improving solubility as it contains an ester group (-COO-). In addition, as it contains an alkyl group, it has the advantage of exhibiting low surface tension characteristics and forming a flat thin film.

In this specification, when a member (layer) is said to be located “on” another member (layer), this means not only when a member (layer) is in contact with another member (layer), but also when there is another member (layer) between the two members (layers). Also includes cases where (layer) exists.

In this specification, when a part "includes" a certain component, this means that it may further include other components rather than excluding other components unless specifically stated to the contrary.

In this specification, the “layer” is interchangeable with the “film” mainly used in the present technical field, 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 a “layer” may be the same as the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.

In the present invention, the “room temperature” refers to a natural temperature that is not heated or reduced, for example, any temperature in the range of about 10°C to 30°C, for example, about 15°C, about 18°C, It means a temperature of about 20℃, about 23℃ or about 25℃. Additionally, in the present invention, unless otherwise specified, the unit of temperature is °C.

In the present invention, “normal pressure” refers to natural pressure that is not pressurized or decompressed, and is usually referred to as atmospheric pressure of about 1 atmosphere (about 700 to 800 mmHg).

Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by a person skilled in the art to which the present invention pertains. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments herein, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, and in case of conflict, unless a specific passage is cited, the present invention, including definitions, will control. Moreover, the materials, methods, and examples are illustrative only and are not intended to be limiting.

" 및 ""는 각각 다른 치환기 또는 결합부에 연결되는 부위를 의미한다.In this specification, "

" and " " means a site connected to a different substituent or bonding group.

In this specification, the term "substitution" means changing a hydrogen atom bonded to a carbon atom of a compound to another substituent, and the position to be substituted is not limited as long as it is a position where a hydrogen atom is substituted, that is, a position where the substituent can be substituted, When two or more substituents are substituted, the two or more substituents may be the same or different from each other.

As used herein, the term “substituted or unsubstituted” refers to hydrogen; heavy hydrogen; halogen group; Amine group; Alkyl group; Aryl group; It means that it is substituted with one or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituents.

In this specification, linking two or more substituents means that the hydrogen of one substituent is linked to another substituent. For example, an isopropyl group and a phenyl group are connected to or It can be a substituent of .

In this specification, the halogen group is a fluoro group (-F), a chloro group (-Cl), a bromo group (-Br), or an iodo group (-I).

In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is 1 to 30; 1 to 20; 1 to 10; Or it is preferably 1 to 5. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, iso Pentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentyl Methyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1 -Dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto.

In the present specification, the alkyl group may include a haloalkyl group, which is an alkyl group substituted with a halogen group. Specific examples include, but are not limited to, a methyl group substituted with three fluoro groups, that is, a trifluoromethyl group.

In this specification, an alkylene group refers to an alkyl group having two bonding positions, that is, a bivalent group. The description of the alkyl group described above can be applied except that each of these is a divalent group.

In this specification, the number of carbon atoms in the cycloalkyl group is not particularly limited, but is preferably 3 to 60. According to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. Specific examples of the cycloalkyl group include, but are not limited to, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, and cyclooctyl group.

In the present specification, the alkoxy group may be straight chain, branched chain, or ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It may be possible, but it is not limited to this.

In this specification, an aryl group refers to a monovalent group of a monovalent aromatic hydrocarbon or an aromatic hydrocarbon derivative. In the present specification, an aromatic hydrocarbon refers to a compound containing 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 with an aromatic hydrocarbon. . Additionally, in the present specification, the aryl group is intended to include a monovalent group in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are linked together. The aryl group is not particularly limited, but 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 preferably 6 to 12, and may be a monocyclic aryl group or a polycyclic aryl group.

The monocyclic aryl group is not particularly limited, but 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 preferably 6 to 12, and may specifically be a phenyl group, biphenyl group, terphenyl group, etc., but is not limited thereto.

The polycyclic aryl group is not particularly limited, but has 6 to 60 carbon atoms; 6 to 45 carbon atoms; 6 to 30 carbon atoms; 6 to 22 carbon atoms; 6 to 22; 6 to 20; 6 to 18; 6 to 16; 6 to 15; 6 to 14; 6 to 13; 6 to 12; Or it is preferably 6 to 10, and may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylenyl group, chrysenyl group, fluorenyl group, etc., but is limited thereto. no.

In the present specification, the aryl group may include a haloaryl group substituted with a halogen group. The haloaryl group refers to an aryl group substituted with one or more halogen groups, and the haloaryl group may be an aryl group substituted with one or more substituents selected from the group consisting of a fluoro group, a chloro group, a bromo group, and an iodo group. In addition, the haloaryl group may be substituted with two or more of the same halogen group. For example, it may be an aryl group substituted with one fluoro group as well as an aryl group substituted with two or more fluoro groups.

In the present specification, an arylene group refers to an aryl group having two bonding positions, that is, a bivalent group. The description of the aryl group described above can be applied, except that each of these is a divalent group.

In the present invention, the heterocyclic group is an aromatic, aliphatic, or condensed ring group of aromatic and aliphatic containing one or more of N, O, P, and S as heteroatoms. The number of carbon atoms of the heterocyclic group is not particularly limited, but may have 2 to 60 carbon atoms.

In the present invention, heteroaryl group refers to a monovalent aromatic hetero ring. Here, the aromatic heterocycle refers to a monovalent group of an aromatic ring or a derivative of an aromatic ring, and includes one or more heteroatoms selected from the group consisting of N, O, P, S, Si, and Se. The derivatives of the aromatic ring include all structures in which an aromatic ring or an aliphatic ring is condensed with an aromatic ring. In addition, in the present invention, the heteroaryl group is intended to include a monovalent group in which two or more aromatic rings containing heteroatoms or derivatives of aromatic rings containing heteroatoms are linked together. 2 to 60 carbon atoms in the heteroaryl group; 2 to 50; 2 to 30; 2 to 20; 2 to 18; Or it is preferably 2 to 13. Examples of heteroaryl groups include thiophene group, furanyl group, pyrrole group, imidazole group, thiazole group, oxazole group, pyridine group, pyrimidine group, triazine group, triazole group, acridine group, pyridazine group, pyrazine group, Quinoline group, quinazoline group, quinoxaline group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzo These include, but are not limited to, furan groups, phenanthrolinyl groups, and dibenzofuran groups.

In the present specification, a heteroarylene group refers to a heteroaryl group having two bonding positions, that is, a bivalent group. The description of the heteroaryl group described above can be applied, except that each of these is a divalent group.

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

In the present specification, the above description regarding the aryl group may be applied to the aromatic ring.

In the present specification, the aliphatic ring is a hydrocarbon ring rather than an aromatic ring, and examples include the cycloalkyl group described above and an adamantyl group.

In the present specification, the curable group can progress a polymerization or crosslinking reaction, through which a large molecular weight increase reaction can proceed, and includes a thermosetting group that is cured by heat or a photocurable group that is cured by light.

In one embodiment of the present specification, the curable group has any one of the following structures.

In the above structure,

R32 and R34 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,

L31 to L38 are the same or different from each other and are each independently directly bonded; -O-; Substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,

l34 to l38 are integers from 1 to 10, and when l34 to l38 are each 2 or more, two or more substituents in parentheses are the same or different from each other,

은 상기 화학식 1에 결합되는 부위이다.

is a site bound to Formula 1 above.

In one embodiment of the present specification, the curable group has any one of the following structures.

In the above structure, L31 to L38, l34 to l38, R32, R34 and is the same as described above.

Hereinafter, the compound represented by Formula 1 will be described in detail.

The ink composition of the present specification includes a compound represented by Formula 1.

In one embodiment of the present specification, Formula 1 is represented by the following Formula 1-1.

[Formula 1-1]

In Formula 1-1,

The definitions of Ar1, Ar2, L10, L11, L20, L21, La, X1, X2, R1 to R4, r1 to r4, and f1 to f4 are the same as in Formula 1.

In an exemplary embodiment of the present specification, L10 and L11 are the same as or different from each other, and each independently represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L10 and L11 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, L10 and L11 are phenylene groups.

In an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 1-2.

[Formula 1-2]

In Formula 1-2,

The definitions of Ar1, Ar2, L20, L21, La, X1, X2, R1 to R4, r1 to r4 and f1 to f4 are the same as in Formula 1,

R5 and R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r5 and r6 are each integers of 0 to 4, and when r5 and r6 are each 2 or more, two or more substituents in parentheses are the same or different from each other.

In an exemplary embodiment of the present specification, R5 and R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R5 and R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; an alkyl group having 1 to 30 carbon atoms; An alkoxy group having 1 to 30 carbon atoms; Aryl group having 6 to 30 carbon atoms; Or it is a heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R5 and R6 are hydrogen.

In an exemplary embodiment of the present specification, r5 and r6 are each 0 or 1.

In one embodiment of the present specification, La is a substituted or unsubstituted divalent hydrocarbon ring group having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present specification, La is a substituted or unsubstituted divalent hydrocarbon ring group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, La is a divalent hydrocarbon ring group having 6 to 30 carbon atoms that is substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, La is one of the following structures.

In the above structure,

R10 to R31 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

n10 to n21 are each integers from 1 to 4, n22, n23, n28 and n29 are each integers from 1 to 3, n24 and n25 are each integers from 1 to 7, n26 is an integer from 1 to 8, and n27 is an integer from 1 to 6, and when n10 to n29 are each 2 or more, 2 or more substituents in parentheses are the same or different from each other,

is the site bound to Chemical Formula 1.

In an exemplary embodiment of the present specification, R10 to R31 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R10 to R31 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R10 to R31 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, L20 and L21 are the same or different from each other and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

In one embodiment of the present specification, L20 and L21 are a direct bond.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms; A biphenyl group substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms; Or it is a terphenyl group substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; Biphenyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; Or it is a terphenyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R1 to R4 are hydrogen.

In an exemplary embodiment of the present specification, f1 is the number of bonding positions at which a substituent can be bonded to 0 to Ar1, and f2 is the number of bonding positions at which a substituent can be bonded to 0 to Ar2. As a specific example, when Ar1 or Ar2 is a phenyl group, the number of bonding positions to which a substituent can be bonded means 5 hydrogen bonded positions, and when Ar1 or Ar2 is a biphenyl group, it means 9 hydrogen bonded positions.

In an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 1-3.

[Formula 1-3]

In Formula 1-3,

The definitions of L10, L11, L20, L21, La, X1, X2, R1 to R4, r1 and r2 are the same as in Formula 1,

L22 and l23 are the same or different from each other and are each independently directly bonded; Or a substituted or unsubstituted arylene group,

R7 and R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r3 and r4 are each integers from 0 to 4, and when r3 and r4 are each 2 or more, 2 or more substituents in parentheses are the same or different from each other,

r7 and r8 are each integers from 0 to 4, and when r7 and r8 are each 2 or more, 2 or more substituents in parentheses are the same or different from each other,

f3 and f4 are each integers from 0 to 5, r3+f3 is 5 or less, r4+f4 is 5 or less,

f7 and f8 are each integers from 0 to 5, f7+r7 is an integer of 5 or less, f8+r8 is an integer of 5 or less, and f3+f4+f7+f8 is an integer of 1 or more.

In an exemplary embodiment of the present specification, f1 and f2 are each integers from 0 to 9.

In an exemplary embodiment of the present specification, f1 and f2 are each integers from 0 to 5.

In an exemplary embodiment of the present specification, f1 and f2 are each integers from 1 to 9.

In an exemplary embodiment of the present specification, f1 and f2 are each integers of 1 to 5.

In an exemplary embodiment of the present specification, f3 and f4 are each integers from 0 to 5.

In an exemplary embodiment of the present specification, f3 and f4 are each integers of 1 to 5.

In an exemplary embodiment of the present specification, f7 and f8 are each integers from 0 to 5.

In an exemplary embodiment of the present specification, f7 and f8 are each integers of 1 to 5.

In one embodiment of the present specification, f1+f2+f3+f4 is an integer from 1 to 28.

In one embodiment of the present specification, f1+f2+f3+f4 is an integer from 1 to 20.

In one embodiment of the present specification, f3+f4+f7+f8 is an integer from 1 to 28.

In one embodiment of the present specification, f3+f4+f7+f8 is an integer from 1 to 20.

In an exemplary embodiment of the present specification, Formula 1 is any one of the following structures.

Hereinafter, the first solvent represented by Formula A will be described in detail.

The ink composition of the present specification includes a first solvent represented by Formula A.

[Formula A]

In Formula A, Y1 to Y10 are the same or different from each other and are each independently hydrogen; heavy hydrogen; hydroxyl group; ether group; carbonyl group; ester group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted amine group.

In an exemplary embodiment of the present specification, Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted amine group.

In an exemplary embodiment of the present specification, Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted alkoxy group.

In an exemplary embodiment of the present specification, Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or it is a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 8 carbon atoms; Or it is a substituted or unsubstituted alkoxy group having 1 to 8 carbon atoms.

In an exemplary embodiment of the present specification, Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group substituted or unsubstituted with an alkoxy group; Or it is an alkoxy group.

In an exemplary embodiment of the present specification, Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; Substituted or unsubstituted ethyl group; Substituted or unsubstituted propyl group; Substituted or unsubstituted butyl group; Substituted or unsubstituted pentyl group; Substituted or unsubstituted hexyl group; Substituted or unsubstituted methoxy group; Or it is a substituted or unsubstituted ethoxy group.

In an exemplary embodiment of the present specification, Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A methyl group substituted or unsubstituted with an alkoxy group; An ethyl group unsubstituted or substituted with an alkoxy group; A propyl group substituted or unsubstituted with an alkoxy group; Butyl group substituted or unsubstituted with an alkoxy group; Pentyl group substituted or unsubstituted with an alkoxy group; Hexyl group substituted or unsubstituted with an alkoxy group; methoxy group; Or it is an ethoxy group.

In one embodiment of the present specification, the first solvent represented by Formula A is any one or a mixture of two or more selected from the group consisting of the following structures.

In an exemplary embodiment of the present specification, the first solvent represented by Formula A is any one of the above structures.

In this specification, the first solvent represented by Formula A has the highest boiling point among the solvents included in the ink composition.

In an exemplary embodiment of the present specification, the boiling point of the first solvent represented by Formula A is 220°C to 340°C; 250°C to 340°C; or 265°C to 340°C.

As the first solvent having a boiling point in the above range is included, when manufacturing an organic light emitting device through a solution process, it can be expected that the flatness of the manufactured pixel and/or the flatness of the organic material layer will be excellent. Specifically, the first solvent represented by Formula A has the lowest vapor pressure among the constituent solvents and is not removed in the initial drying step, so it has the advantage of being able to control the difference in surface tension between the remaining materials even after the initial drying step. As a result, there is an advantage in that the flatness of the manufactured pixel and/or the organic layer is excellent.

In one embodiment of the present specification, the surface tension of the first solvent represented by Formula A is 32 mN/m to 38 mN/m. Specifically, 33 mN/m to 37 mN/m; or 33.5 mN/m to 36.5 mN/m.

By limiting the surface tension of the first solvent, the range of surface tension between materials other than the first solvent can be easily adjusted. Specifically, the materials included in the ink composition used in the solution process (e.g., the second solvent represented by Formula B, other organic solvents, etc.) generally have a surface tension value in the range of 25 mN/m to 45 mN/m. has When a small amount of the first and second solvents remain at the late stage of ink drying, if the difference in surface tension between the first and second solvents is large, the ultimately formed thin film may become uneven. Therefore, if the difference in surface tension between the first and second solvents is small, It is desirable. The surface tension in the range of 32 mN/m to 38 mN/m is close to the middle value of the surface tension range of 25 mN/m to 45 mN/m, which is the surface tension value of the common organic solvents, and accordingly, represented by the formula A If the first solvent has a surface tension in the range of 32 mN/m to 38 mN/m, the difference in surface tension between materials other than the first solvent can be adjusted to be small.

Hereinafter, the second solvent represented by Formula B will be described in detail.

The ink composition of the present specification includes a second solvent represented by Formula B.

In an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; -O-; Or it is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; -O-; Or it is an alkylene group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Formula B is any one of the following Formulas B-1 to B-3.

[Formula B-1]

[Formula B-2]

[Formula B-3]

In the above formulas B-1 to B-3,

Z1 and Z2 are the same or different from each other and are each independently a substituted or unsubstituted alkyl group,

L1' and L2 are the same or different from each other, and each independently represents a substituted or unsubstituted alkylene group.

In an exemplary embodiment of the present specification, L1' and L2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L1' and L2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, L1' and L2 are the same as or different from each other, and each independently represents an alkylene group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L1' and L2 are the same as or different from each other, and each independently represents an alkylene group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, L1' and L2 are the same as or different from each other, and are each independently a straight-chain alkylene group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, Z1 and Z2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Z1 and Z2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, Z1 and Z2 are the same as or different from each other, and are each independently an alkyl group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Z1 and Z2 are the same as or different from each other, and are each independently a straight-chain or branched alkyl group.

In an exemplary embodiment of the present specification, Z1 and Z2 are the same or different from each other, and are each independently a straight-chain alkyl group having 1 to 30 carbon atoms; Or it is a branched alkyl group having 3 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Z1 and Z2 are the same as or different from each other, and are each independently a straight-chain alkyl group having 1 to 10 carbon atoms; Or it is a branched alkyl group having 3 to 10 carbon atoms.

In one embodiment of the present specification, the second solvent represented by Formula B is any one or a mixture of two or more selected from the group consisting of the following structures.

In an exemplary embodiment of the present specification, the second solvent represented by Formula B is any one of the above structures.

In one embodiment of the present specification, the surface tension of the second solvent represented by Formula B is 25 mN/m to 35 mN/m; or 27 mN/m to 35 mN/m.

In an exemplary embodiment of the present specification, the boiling point of the second solvent represented by Formula B is 70°C to 320°C; 100°C to 320°C; or 150°C to 310°C.

In one embodiment of the present specification, the ink composition uses a material with a boiling point relatively lower than that of the first solvent represented by Formula A as the second solvent represented by Formula B. That is, among the solvents included in the ink composition, the boiling point of the first solvent represented by Formula A is higher than the boiling point of the second solvent represented by Formula B.

Hereinafter, the third solvent represented by Formula C will be described in detail.

The ink composition of the present specification further includes a third solvent represented by Formula C.

[Formula C]

In the formula C,

G1 and G2 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

g1 is an integer from 1 to 5, and when g1 is 2 or more, the substituents in parentheses are the same or different from each other.

In an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted alkyl group.

In an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is an alkyl group.

In an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is an alkyl group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is an alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, Formula C has the following structure.

In one embodiment of the present specification, the surface tension of the third solvent represented by Formula C is 25 mN/m to 37 mN/m; or 27 mN/m to 37 mN/m.

In an exemplary embodiment of the present specification, the boiling point of the solvent represented by Formula C is 70°C to 300°C; 100°C to 300°C; or 150°C to 270°C.

In one embodiment of the present specification, the third solvent of Formula C has a lower boiling point than other solvents included in the ink composition.

In one embodiment of the present specification, the ink composition includes a first solvent represented by Formula A; a second solvent represented by formula B; and a third solvent represented by Formula C. At this time, the boiling point of the first solvent is the highest, the boiling point of the second solvent is medium, and the boiling point of the third solvent is the lowest.

Hereinafter, the ionic compound containing an anion group represented by Formula 2 will be described in detail.

In one embodiment of the present specification, the ink composition further includes an ionic compound containing an anionic group represented by the following formula (2).

[Formula 2]

In Formula 2,

At least one of R201 to R220 is F; Cyano group; Or a substituted or unsubstituted fluoroalkyl group,

At least one of the remaining R201 to R220 is a curable group,

The remaining R201 to R220 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; nitro group; Cyano group; amino group; -OR221; -SR222; -SO ₃ R223; -COOR224; -OC(O)R225; -C(O)NR226R227; -C(O)R228; 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 a substituted or unsubstituted heterocyclic group,

R221 to R228 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, the ionic compound containing an anionic group represented by Formula 2 has a curable group introduced.

Unlike Formula 2, in the case of an ionic compound in which a curable group is not introduced, it is not cured, so the characteristics of the device are reduced due to movement between electrodes or layers of the ionic compound. On the other hand, as the number of curable groups in the ionic compound increases, the curing rate of the ionic compound or a composition containing it increases and the film retention rate improves.

In an exemplary embodiment of the present specification, the number of curable groups in the anionic group represented by Formula 2 is 1.

In one embodiment of the present specification, the number of curable groups in the anionic group represented by Formula 2 is two.

In one embodiment of the present specification, the number of curable groups in the anionic group represented by Formula 2 is 4.

In an exemplary embodiment of the present specification, it is more preferable that the anionic group represented by Formula 2 includes four curable groups in terms of film retention rate.

In an exemplary embodiment of the present specification, the compound of Formula 2 includes 8 to 20 F.

In one embodiment of the present specification, the number of F, cyano groups, or substituted or unsubstituted fluoroalkyl groups in the anionic group represented by Formula 2 is 16 to 19.

As described above, as the ratio of F, cyano group, or fluoroalkyl group in the molecule increases, the film retention rate improves during heat treatment.

In an exemplary embodiment of the present specification, the weight of F in the anionic group is 15 to 50 parts by weight, based on 100 parts by weight of the anionic group represented by Formula 2.

In an exemplary embodiment of the present specification, the weight of F in the anionic group is 10 to 45 parts by weight, based on 100 parts by weight of the anionic group represented by Formula 2.

In one embodiment of the present specification, an ionic compound containing an anionic group represented by Formula 2 may be used in a hole injection layer of an organic light-emitting device, and when used in a hole injection layer, it may be used as a dopant. At this time, as the content of F increases, the force to attract electrons from other compounds (host compounds) increases, and holes are more likely to be created in the host, thereby improving the performance of the hole injection layer.

In one embodiment of the present specification, 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, a method generally used for F analysis.

In an exemplary embodiment of the present specification, Formula 2 is any one of the following structures.

In the above structure,

n1 is an integer from 1 to 3, m1 is an integer from 1 to 3, n1+m1=4,

n2 is an integer from 0 to 3, m2 is an integer from 1 to 4, n2+m2=4,

M1 is deuterium; halogen group; nitro group; Cyano group; amino group; -OR221; -SR222; -SO ₃ R223; -COOR224; -OC(O)R225; -C(O)NR226R227; -C(O)R228; 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 a substituted or unsubstituted heterocyclic group,

R221 to R228 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,

i is an integer from 1 to 4, and when i is 2 or more, 2 or more M1s are the same or different from each other.

In an exemplary embodiment of the present specification, the ionic compound further includes a cationic group. Specifically, the above-described ink composition further includes an ionic compound containing an anionic group and a cationic group represented by the above-described formula (2).

In one embodiment of the present specification, the ionic compound further includes a cationic group, and the cationic group includes a monovalent cationic group, an onium compound, or any one of the following structures.

In the above structures,

Q30 to Q105 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Cyano group; nitro group; halogen group; hydroxyl group; -COOR250; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or it is a hardening stage,

R250 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,

x is an integer from 0 to 10,

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

In an exemplary embodiment of the present specification, the monovalent cationic group may be an alkali metal cation, and the alkali metal cation may include Na ⁺ , Li ⁺ , K ^{+ ,} etc., but is not limited thereto.

In one embodiment of the present specification, the cationic compound is an onium compound; Or any one selected from the structural formulas described above.

In an exemplary embodiment of the present specification, the cationic group has any one of the following structures.

In the above structures,

Q30 to Q34, Q30' to Q34' and Q62 to Q95 are the same or different from each other and are each hydrogen; heavy hydrogen; Cyano group; nitro group; halogen group; hydroxyl group; -COOR250; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or it is a hardening stage,

R250 is hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted alkyl group.

In an exemplary embodiment of the present specification, the cationic group has any one of the following structures.

In an exemplary embodiment of the present specification, the ionic compound is any one of the following formulas D-1 to D-37.

In one embodiment of the present specification, in the ionic compound, the anionic group and the cationic group represented by Formula 2 are included in an equivalence ratio of 1:5 to 5:1. Specifically, the anionic group and cationic group represented by Formula 2 are included in an equivalence ratio of 1:1.

Below, the ink composition will be described in detail.

The present specification includes compounds represented by the above-mentioned formula (1); A first solvent represented by the above-mentioned formula A; and a second solvent represented by the above-described formula B.

In one embodiment of the present specification, the ink composition further includes an ionic compound containing an anionic group represented by the above-described formula (2).

In one embodiment of the present specification, the ionic compound further includes the above-described cationic group.

In one embodiment of the present specification, the ink composition may further include an additional solvent. The additional solvent includes chlorine-based solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; Ether-based solvents such as tetrahydrofuran, dioxane, and dipropylene glycol monomethyl ether; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone-based solvents such as acetone, methyl ethyl ketone, cyclohexanone, isophorone, Tetralone, Decalone, and Acetylacetone; Ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, and benzyl butyrate; Polyhydric acids such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, etc. alcohol and its derivatives; Alcohol-based solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide-based solvents such as dimethyl sulfoxide; and amide-based solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; and at least one selected from the group consisting of tetralin. However, it is not limited to the above example, and any solvent that can dissolve or disperse the compound represented by the above-mentioned formula (1) can be used.

An exemplary embodiment of the present specification includes a compound represented by the above-mentioned formula 1; A first solvent represented by the above-mentioned formula A; A second solvent represented by the above-mentioned formula B; A third solvent represented by the above-mentioned formula C; and an ionic compound containing an anionic group represented by the above-described formula (2).

In one embodiment of the present specification, with respect to 100 wt% of the ink composition, the compound represented by Formula 1 is contained in an amount of 0.1 wt% to 10 wt%; or 0.1 wt% to 5 wt%.

In one embodiment of the present specification, with respect to 100 wt% of the ink composition, the first solvent represented by Formula A is 0.5 wt% to 70 wt%; 3 wt% to 50 wt%; or 5wt% to 30wt%.

In one embodiment of the present specification, with respect to 100 wt% of the ink composition, the second solvent represented by Formula B is 0.5 wt% to 70 wt%; 3 wt% to 50 wt%; or 5wt% to 30wt%.

In one embodiment of the present specification, with respect to 100 wt% of the ink composition, the third solvent represented by the formula C is 1 wt% to 90 wt%; 5 wt% to 90 wt%; or 10 wt% to 85 wt%.

In one embodiment of the present specification, based on 100 wt% of the ink composition, the ionic compound containing an anionic group represented by Formula 2 is contained in an amount of 0.1 wt% to 10 wt%; or 0.1 wt% to 5 wt%.

In one embodiment of the present specification, with respect to 100 wt% of the ink composition, the additional solvent is 0 wt% to 80 wt%; or 0 wt% to 50 wt%.

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

The viscosity is a value measured at room temperature using a Brookfield viscometer after dissolving the object to be measured in the first to third solvents mixed in a random ratio at a concentration of 1 wt% to 3 wt%. At this time, the object to be measured is a compound represented by Formula 1; or a mixture of the compound represented by Formula 1 and the above-mentioned ionic compounds.

In one embodiment of the present specification, the ink composition is in a liquid form. The “liquid phase” means that it is in a liquid state at room temperature and pressure.

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

In one embodiment of the present specification, the ink composition is a single molecule containing a photocurable group and/or a thermosetting group; Or, it further includes a single molecule containing a terminal group capable of forming a polymer by heat. A single molecule containing a photocurable group and/or a thermocurable group as described above; Alternatively, the molecular weight of a single molecule containing a terminal group capable of forming a polymer by heat may be 3,000 g/mol or less, but the molecular weight is not limited to the above examples.

A single molecule containing the photo-curable group and/or thermo-curable group; Alternatively, single molecules containing terminal groups capable of forming polymers by heat include aryl such as phenyl, biphenyl, fluorene, and naphthalene; Arylamine; Alternatively, it may refer to a single molecule in which fluorene is substituted with a photocurable group and/or a thermosetting group or a terminal group capable of forming a polymer by heat.

In one embodiment of the present specification, the ink composition is used to form one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer.

Hereinafter, a pixel containing the above-described ink composition or a cured product thereof will be described in detail.

One embodiment of the present specification provides a pixel containing the above-described ink composition or a cured product thereof. The pixel may be included in an organic material layer, an organic light emitting diode, or an organic light emitting display device. Specific details regarding the organic layer will be described later.

In one embodiment of the present specification, the organic light emitting display device includes a plurality of pixels composed of red (R), green (G), and blue (B) subpixels, and each subpixel includes an organic light emitting diode and a pixel circuit. is located. The organic light emitting diode includes two electrodes (anode and cathode) and an organic light emitting layer positioned between them, and the pixel circuit includes at least two thin film transistors and at least one capacitor. The organic material layer, organic light emitting diode, or organic light emitting display device may include a bank. Preferably, the organic material layer, organic light emitting diode, or organic light emitting display device may include a bank in the form of a line. The line-shaped bank may define a line-shaped pixel area and/or a sub-pixel area. In normal cases, the light-emitting layer of the organic material layer consists of a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer located in each of the red subpixel, green subpixel, and blue subpixel. At this time, the aforementioned pixel may correspond to the pixel or subpixel. As a preferred example, the pixel corresponds to the subpixel.

In one embodiment of the present specification, the flatness of the pixel is 20 nm or less.

In an exemplary embodiment of the present specification, the flatness refers to a value measured by a 10-point average roughness (Rz) of a pixel.

In one embodiment of the present specification, the flatness may be measured by an optical thickness measuring device. The optical thickness measuring device may be Bruker's Optical Profiler, but is not limited thereto.

In one embodiment of the present specification, the 10-point average roughness can be measured using a measurement method known in the art. Specifically, the 10-point average roughness can be measured based on a size of 40 μm x 40 μm inside the pixel. For example, as shown in FIG. 5, the 10-point average roughness Rz in measurement area A (40 μm x 40 μm) among the formed pixels is measured.

In one embodiment of the present specification, the 10-point average roughness is the average value of the height from the highest mountain peak to the 5th highest mountain peak and the lowest valley measured in the height direction from the average line by sampling the reference length from the cross-sectional curve. It is a value obtained by calculating the sum of the average value of the absolute value of the depth from to the bottom of the 5th lowest trough.

In one embodiment of the present specification, the low flatness value means that the pixel is formed flat. In other words, the lower the flatness (average roughness of 10 points) value, the more uniformly the pixels are formed.

In an exemplary embodiment of the present specification, the one or more pixels may be included in the above-described organic material layer, organic light emitting diode, or organic light emitting display device.

Hereinafter, the organic material layer including the above-described pixels and the organic light-emitting device including the same will be described in detail.

One embodiment of the present specification provides an organic material layer including the above-described pixels. Since the pixel contains the above-described ink composition or a cured product thereof, an embodiment of the present specification may be said to provide an organic material layer containing the above-described ink composition or a cured product thereof.

In one embodiment of the present specification, the organic material layer includes a plurality of the pixels. For example, the organic material layer includes an x-axis in which na pixels are arranged, and a y-axis perpendicular to the x-axis and in which nb pixels are arranged, where na and nb are each integers of 2 to 10 ⁴ .

In an exemplary embodiment of the present specification, na and nb are each 2 or more; 5 or more; over 10; 20 or more; or greater than or equal to 40 and less than or equal to 10 ⁴ ; 10 ³ or less; or 10 ² or less.

In an exemplary embodiment of the present specification, the organic material layer includes two or more pixels; 4 or more; more than 10; 20 or more; 40 or more; 80+; or contains 100 or more, but not more than 10 ⁸ ; 10 ⁶ or less; 10 ⁴ or less; or 10 or ³ or less.

In one embodiment of the present specification, pixels included in the organic material layer are arranged in the form of a line. For example, as shown in FIG. 2, a plurality of pixels 1' are arranged in a line to form a line.

In one embodiment of the present specification, the organic material layer includes several lines where the plurality of pixels are arranged in a row. For example, as shown in FIG. 2, a plurality of lines may be formed at regular intervals. For example, the y-axis on which the above-mentioned nb pixels are listed is one line, and may include as many lines as the number of pixels (na) included in the x-axis.

In one embodiment of the present specification, the organic material layer includes na x nb pixels.

In one embodiment of the present specification, the plurality of pixels included in the organic material layer have uniform thickness.

In one embodiment of the present specification, the organic material layer is included in the organic light-emitting device.

In one embodiment of the present specification, the organic layer is formed through a solution process.

An exemplary embodiment of the present specification includes a first electrode; second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer is the organic material layer described above.

That is, an exemplary embodiment of the present specification includes a first electrode; second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one organic material layer is an organic material layer including the above-described pixels.

As described above, since the pixel contains the above-described ink composition or a cured product thereof, the fact that the organic material layer includes the pixel means that the organic material layer includes the ink composition or a cured product thereof. That is, an exemplary embodiment of the present specification includes a first electrode; second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the above-described ink composition or a cured product thereof.

In one embodiment of the present specification, the organic material layer is 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. Includes one or more floors as selected. However, the organic material layer forming the above group is only an example, and the organic material layers are not limited to the above-mentioned examples. Additionally, the organic material layer may include two or more layers performing the same role, if necessary. The 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.

In one embodiment of the present specification, the organic material layer of the organic light-emitting device has a single-layer structure. For example, the organic material layer of the single-layer structure is provided between the first electrode and the second electrode of the organic light-emitting device, and the organic material layer includes the ink composition or a cured product thereof.

In one embodiment of the present specification, the organic layer having a single-layer structure is a light-emitting layer, and in this case, the light-emitting layer includes the ink composition or a cured product thereof.

In one embodiment of the present specification, the organic material layer of the organic light emitting device has a multi-layer structure in which two or more organic material layers are stacked. The multi-layered organic material layer is provided between the first electrode and the second electrode of the organic light emitting device.

In one embodiment of the present specification, the organic material layer of the multi-layer structure includes a light-emitting layer and an organic material layer other than the light-emitting layer. As an example, the light-emitting layer is provided between the first electrode and the second electrode, and an organic material layer other than the light-emitting layer is provided between the first electrode and the light-emitting layer. As another example, the light-emitting layer is provided between the first electrode and the second electrode, and an organic layer other than the light-emitting layer is provided between the light-emitting layer and the second electrode. As another example, the light-emitting layer is provided between the first electrode and the second electrode, one organic layer other than the light-emitting layer is provided between the first electrode and the light-emitting layer, and one organic material layer other than the light-emitting layer is the light-emitting layer and It is provided between the second electrodes. However, the above structure is only an example, and the organic light emitting device of the present specification is not limited to the above structure.

In one embodiment of the present specification, the organic layer other than the light-emitting layer is a 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. It may be one or more floors selected from, but is not limited to this.

In an exemplary embodiment of the present specification, at least one layer of the multi-layered organic material layer includes the above-described ink composition or a cured product thereof. For example, the multi-layer organic material layer includes one organic material layer containing the ink composition or a cured product thereof and an additional organic material layer. In one embodiment of the present specification, the additional organic material layer does not include the ink composition or a cured product thereof. In another exemplary embodiment, the additional organic material layer includes the ink composition or a cured product thereof.

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

In one embodiment of the present specification, the organic material layer includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer, and the hole injection layer, the hole transport layer, and the hole At least one layer selected from the group consisting of an injection and transport layer and an electron blocking layer includes the ink composition or a cured product thereof.

In one embodiment of the present specification, the organic material layer includes a hole injection layer, and the hole injection layer includes the ink composition or a cured product thereof.

In one embodiment of the present specification, the organic material layer further includes one or more layers selected from the group consisting of a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer. As an example, one or more layers selected from the group consisting of the hole blocking layer, the electron transport layer, the electron injection layer, and the electron injection and transport layer include the ink composition or a cured product thereof. As another example, one or more layers selected from the group consisting of the hole blocking layer, the electron transport layer, the electron injection layer, and the electron injection and transport layer do not include the ink composition or a cured product thereof.

In one embodiment of the present specification, the organic light emitting device includes a first electrode; second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein the organic material layer includes a light-emitting layer, a hole injection layer, and an electron blocking layer, and the hole injection layer or the electron blocking layer is the ink. It includes a composition or a cured product thereof.

Generally, in an organic light emitting device, a hole injection layer, a hole transport layer, and an electron blocking layer are provided between the anode and the light emitting layer. As a specific example, the hole injection layer is provided on the anode, the hole transport layer is provided on the hole injection layer, and the electron blocking layer is provided on the hole injection layer, but the structure is not limited to the above example.

Additionally, generally in organic light emitting devices, 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 the light emitting layer, the electron transport layer is provided on the hole blocking layer, and the electron injection layer is provided on the electron transport layer, but the structure is not limited to the above examples.

The structure of an organic light-emitting device according to an exemplary embodiment of the present specification is illustrated in FIG. 1. In Figure 1, 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 provided on the substrate 101. The structure of sequentially stacked organic light emitting devices is illustrated.

In one embodiment of the present specification, the hole injection layer 301 and/or the hole transport layer 401 of FIG. 1 may include the above-described ink composition or a cured product thereof, or may be formed using the ink composition. .

1 illustrates an organic light-emitting device according to an exemplary embodiment of the present specification, and the structure of the organic light-emitting device of the present specification is not limited thereto.

As described above, an organic light-emitting device having a single-layer or multi-layer organic material layer may have, for example, a stacked structure as shown below, but is not limited thereto.

(1) Anode/hole transport layer/light emitting layer/cathode

(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode

(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode

(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode

(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

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

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

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

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

(10) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode

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

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

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

(14) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode

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

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

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

(18) Anode/hole injection layer/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capsule

(19) Anode/hole injection layer/first hole transport layer/second hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capsule

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

Additionally, in the above structure, 'hole injection layer/hole transport layer' can be replaced with 'hole injection and transport layer' or 'layer that performs hole injection and hole transport simultaneously'.

In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

In one embodiment of the present specification, the first electrode is a cathode, and the second electrode is an anode.

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

In one embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

Hereinafter, the manufacturing method of the organic light emitting device will be described in detail.

One embodiment of the present specification includes preparing a first electrode;

Forming one or more organic layers on the first electrode; and

Comprising the step of forming a second electrode on the organic layer,

The step of forming the organic material layer provides a method of manufacturing an organic light-emitting device including forming one or more organic material layers using the above-described ink composition.

In one embodiment of the present specification, the step of forming one or more organic material layers using the ink composition may be performed on a substrate or organic material layer including a line-shaped bank.

As an example, the above-described ink composition is applied to a substrate including line-shaped banks (line bank inkjet substrate, FIG. 2) (FIG. 3), and then the ink composition is dried and/or heat-treated to form a thin film (FIG. 4). )can do.

In one embodiment of the present specification, the step of forming one or more organic layers using the ink composition uses a spin coating method.

In one embodiment of the present specification, the step of forming one or more organic layers using the ink composition uses a printing method.

In one embodiment of the present specification, the printing method includes, for example, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing, but is not limited to the printing methods listed above.

In one embodiment of the present specification, the step of forming one or more organic layers using the ink composition uses an inkjet printing method.

The ink composition according to an exemplary embodiment of the present specification is suitable for a solution process due to its structural characteristics and can be formed by a printing method, so it is economical in terms of time and cost when manufacturing a device. Additionally, since a solution process is possible, it is possible to increase the area of the device.

In one embodiment of the present specification, the step of forming one or more organic layers on the first electrode may further include one or more steps of reducing pressure and then drying. As an example, the step of forming one or more organic layers on the first electrode further includes two steps of pressure reduction and drying. At this time, the first drying step after decompression is performed from normal pressure to 2 x 10 ^-2 torr, and decompression from normal pressure to 2 x 10 ^-2 torr can be performed for 30 to 600 seconds. In addition, the second decompression drying step is performed from 2 x 10 ^-2 to 2 x 10 ^-6 torr, and the decompression from 2 x 10 ^-2 torr to 2 x 10 ^-6 torr is performed for 30 to 600 seconds. You can.

In one embodiment of the present specification, forming an organic layer using the ink composition includes coating the ink composition; and heat-treating or light-treating the coated ink composition.

In one embodiment of the present specification, forming one or more organic material layers using the ink composition includes coating a coating composition on the first electrode or one or more organic material layers; and heat-treating or light-treating the coated coating composition.

When the step of forming one or more organic layers formed using the ink composition includes the heat treatment or light treatment step, a plurality of the compounds included in the ink composition form crosslinks to provide an organic layer containing a thin film structure. You can. At this time, when another layer is laminated on the surface of the organic layer formed using the ink composition, it can be prevented from being dissolved by a solvent, morphologically affected, or decomposed.

Therefore, when the organic material layer formed using the ink composition is formed including a heat treatment or light treatment step, the resistance to solvent increases, so that a multilayer can be formed by repeatedly performing the solution deposition and crosslinking methods, and the stability increases, thereby increasing the device's stability. Lifespan characteristics can be increased.

In one embodiment of the present specification, the heat treatment temperature in the heat treatment step is 85°C to 250°C; 100°C to 250°C; Or it may be 150°C to 250°C.

In one embodiment of the present specification, the heat treatment time in the heat treatment step is 10 minutes to 2 hours; 10 minutes to 1 hour; Or it may range from 20 minutes to 1 hour.

In one embodiment of the present specification, the organic light-emitting device may be manufactured using materials and methods known in the art, except that one or more organic layers are formed using the above-described ink composition.

For example, the organic light emitting device of the present specification can be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on the substrate to form an anode. After forming an organic layer including 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, a deposition process, etc., thereon, It can be manufactured by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

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

The cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. metals or alloys thereof, for example magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; Examples include, but are not limited to, multi-layered materials such as LiF/Al or LiO ₂ /Al.

The light emitting layer may include a host material and/or a dopant material.

The host material includes a condensed aromatic ring derivative or a heterocyclic ring-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, These include, but are not limited to, pyrimidine derivatives.

The dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group, and include pyrene, anthracene, chrysene, periplanthene, etc. having an arylamine group. In addition, a styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. The substituent is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. Additionally, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

The hole injection layer is a layer that receives holes from the electrode. The hole injection material preferably has the ability to transport holes and has an excellent hole receiving effect from the anode and an excellent hole injection effect with respect to the light emitting layer or light emitting material. Additionally, a material that has an excellent ability to prevent the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material is desirable. Additionally, materials with excellent thin film forming ability are desirable. Additionally, it is preferable that the HOMO of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, and arylamine-based organic materials; Hexanitrilehexaazatriphenylene series organic substances; Organic substances of the quinacridone series; Perylene-based organic substances; Polythiophene-based conductive polymers such as anthraquinone and polyaniline; There are compounds of the above-mentioned formula 1, but they are not limited thereto.

In one embodiment of the present specification, the hole injection layer is formed of the above-described ink composition or a cured product thereof.

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

In one embodiment of the present specification, the ionic compound is included as a dopant in the hole injection layer.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and may have a single-layer structure or a multi-layer structure of two or more layers. The hole transport material is preferably a material that can receive holes from the anode or hole injection layer and transfer them to the light emitting layer, and has high mobility for holes. Specific examples of hole transport materials include, but are not limited to, arylamine-based organic materials, carbazole-based compounds, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transport material is a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is preferred. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq ₃ ; organic radical compounds; These include, but are not limited to, hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material, as used according to the prior art. In particular, suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.

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

The electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. The electron blocking layer may be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously performs hole injection and hole transport, using the compound of Formula 2 described above.

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. The hole blocking layer material specifically includes, but is not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

The hole injection and transport layer may include the materials of the hole injection layer and hole transport layer described above.

The electron injection and transport layer may include the materials of the electron injection layer and hole transport layer described above.

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

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

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

The electronic device includes an 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 clad plate, a buffer coat film, and a multilayer printed circuit board. Insulating film for solder resist film, insulating film for OLED, protective film for thin film transistor of liquid crystal display device, electrode protective film and semiconductor protective film for organic EL device, OLED insulating film, LCD insulating film, semiconductor insulating film, solar module, touch panel, display panel, etc. It may include all devices, etc., but is not limited thereto.

Hereinafter, the present invention will be described in detail with reference to examples. However, the embodiments according to the present invention may be modified into various other forms, and the scope of the present specification is not to be construed as limited to the embodiments described below. The embodiments of this specification are provided to more completely explain the present invention to those skilled in the art.

< Synthesis example A. Preparation of compounds>

Synthesis example A-1. Preparation of Compound H-1

(1) Preparation of intermediate 1-1

1-Bromo-3-fluorobenzene (27.9 mL, 255 mmol) was added to tetrahydrofuran (THF) (500 mL). After purging with nitrogen, it was cooled to -78°C. n -BuLi (2.5 M Hex) (96 mL, 240 mmol) was placed in a dropping funnel and then slowly added to the reaction mixture. It was stirred at -78°C for 30 minutes. 2-bromofluorenone (38.9 g, 150 mmol) was added. The temperature was slowly raised to room temperature and stirred overnight. The reaction was terminated by adding distilled water, and then extracted with ethyl acetate and water. After collecting the organic layer, it was dried using MgSO ₄ and filtered. The filtrate was dried using a vacuum rotary concentrator to remove the organic solvent, and intermediate 1-1 was obtained and used in the next reaction.

(2) Preparation of intermediate 1-2

Intermediate 1-1 (53 g, 150 mmol) and phenol (70.6 g, 750 mmol) were added to a round bottom flask (RBF). CH ₃ SO ₃ H (214 mL) was added and stirred at 60°C for 4 hours. After adding ice water, extraction was performed with ethyl acetate and water. After collecting the organic layer, it was dried using MgSO ₄ and filtered. The filtrate was dried using a vacuum rotary concentrator to remove the organic solvent. After column purification, 40.6 g of intermediate 1-2 was obtained by crystallization under dichloromethane/heptane conditions.

(3) Preparation of intermediate 1-3

Intermediate 1-2 (40 g, 92.7 mmol), 4-nitrobenzaldehyde (21.2 g, 139 mmol), Cu(OAc) ₂ (842 mg, 4.64 mmol) and Cs ₂ CO ₃ (45.3 g, 139 mmol) was added to RBF. Dimethylformamide (DMF) (310 mL) was added and stirred at 100°C for 4 hours. After extraction with ethyl acetate and water, the organic layer was collected, dried using MgSO ₄ and filtered. The filtrate was dried using a vacuum rotary concentrator to remove the organic solvent. After column purification, 38.7 g of intermediate 1-3 was obtained by crystallization under dichloromethane/heptane (DCM/Heptane) conditions.

(4) Preparation of intermediate 1-4

CH ₃ PPh ₃ Br (51.6 g, 144.6 mmol), KOtBu (16.2 g, 144.6 mmol), and THF (217 mL) were placed in RBF and cooled to 0°C. A solution of Intermediate 1-3 (38.7 g, 72.3 mmol) dissolved in tetrahydrofuran (THF) (144 mL) was added to the reaction mixture. The temperature was raised to room temperature and stirred for 1 hour. After extraction with ethyl acetate and water, the organic layer was collected, dried using MgSO ₄ and filtered. The filtrate was dried using a vacuum rotary concentrator to remove the organic solvent. After column purification, 33.7 g of intermediate 1-4 was obtained by crystallization under DCM/EtOH conditions.

(5) Preparation of compound H-1

N,N'-Bis(4-fluorophenyl)benzidine (944 mg, 2.5 mmol), intermediate 1-4 (2.73 g, 5.13 mmol), Pd ( PtBu ₃ ) ₂ (64 mg, 0.125 mmol) and NaOtBu (961 mg, 10 mmol) were added to RBF. After purging with nitrogen, toluene (12.5 mL) was added and stirred at 90°C for 1 hour. After extraction with ethyl acetate and water, the organic layer was collected, dried using MgSO ₄ and filtered. The filtrate was dried using a vacuum rotary concentrator to remove the organic solvent. After column purification, 2.7 g of compound H-1 was obtained by crystallization under DCM/EtOH conditions. The synthesis of the compound was confirmed through LC-MS and NMR. MS: [M+H] ⁺ = 1277

NMR measurements of compound H-1: ¹ H NMR (500 MHz, DMSO-d6) δ 7.83 (m, 4H), 7.45 - 7.36 (m, 12H), 7.27 (t, 2H), 7.17 - 6.86 (m, 36H), 6.65 - 6.57 (m, 2H), 5.65 (dd, 2H), 5.11 (dd, 2H)

Synthesis example A-2. Preparation of Compound H-2

(1) Preparation of intermediate 2-4

Synthesis Example A, except that 1-bromo-4-fluorobenzene was used instead of 1-bromo-3-fluorobenzene in (1) of Synthesis Example A-1. Intermediate 2-1 was prepared in the same manner as (1) in -1. Thereafter, in (2) to (4) of Synthesis Example A-1, except that 2-1 was used instead of 1-1, 2-2 was used instead of intermediate 1-2, and 2-3 was used instead of intermediate 1-3. prepared intermediates in the same manner as (2) to (4) of Synthesis Example A-1, and finally obtained intermediate 2-4.

(2) Preparation of compound H-2

Compound H-2 was obtained in the same manner as (5) of Synthesis Example A-1, except that 2-4 was used instead of intermediate 1-4 in (5) of Synthesis Example A-1. The synthesis of the compound was confirmed through LC-MS and NMR. MS: [M+H] ⁺ = 1277

NMR measurements of compound H-2: ¹ H NMR (500 MHz, DMSO-d6) δ 7.83 (m, 4H), 7.45 - 7.36 (m, 12H), 7.27 (t, 2H), 7.17 - 6.86 (m, 36H), 6.65 - 6.57 (m, 2H), 5.65 (dd, 2H), 5.11 (dd, 2H)

Synthesis example A-3. Preparation of Compound 3

(1) Preparation of intermediate 3-4

In (1) of Synthesis Example A-1, except that 4-bromo-1,2-difluorobenzene was used instead of 1-bromo-3-fluorobenzene. Then, intermediate 3-1 was prepared in the same manner as (1) of Synthesis Example A-1. Thereafter, in (2) to (4) of Synthesis Example A-1, except that 3-1 was used instead of 1-1, 3-2 was used instead of intermediate 1-2, and 3-3 was used instead of intermediate 1-3. prepared intermediates in the same manner as (2) to (4) of Synthesis Example A-1, and finally obtained intermediate 3-4.

(2) Preparation of compound H-3

Compound H-3 was obtained in the same manner as (5) of Synthesis Example A-1, except that 3-4 was used instead of intermediate 1-4 in (5) of Synthesis Example A-1. The synthesis of the compound was confirmed through LC-MS and NMR. MS: [M+H] ⁺ = 1313

NMR measurements of compound H-3: ¹ H NMR (500 MHz, DMSO-d6) δ 7.87 (t, 4H), 7.50 (d, 4H), 7.44 - 7.27 (m, 12H), 7.11 - 7.00 (m, 22H) 6.94 - 6.83 (m, 10H), 6.66 - 6.59 (m, 2H), 5.66 (dd, 2H), 5.12 (dd, 2H)

Synthesis example A-4. Preparation of Compound H-4

2,2'-Bis(4-fluorophenylamino)-9,9'-spirobi[9 H -fluorene](2,2'-Bis(4-fluorophenylamino)-9,9'-spirobi[9 H -fluorene]) (1.34 g, 2.5 mmol), intermediate 2-4 (2.73 g, 5.13 mmol), Pd(PtBu ₃ ) ₂ (64 mg, 0.125 mmol) and NaOtBu (961 mg, 10 mmol) in RBF. I put it in. After purging with nitrogen, toluene (12.5 mL) was added and stirred at 90°C for 1 hour. After extraction with ethyl acetate and water, the organic layer was collected, dried using MgSO ₄ and filtered. The filtrate was dried using a vacuum rotary concentrator to remove the organic solvent. After column purification, 2.9 g of compound H-4 was obtained by crystallization under DCM/EtOH conditions. The synthesis of the compound was confirmed through LC-MS and NMR. MS: [M+H] ⁺ = 1440

NMR measurements of compound H-4: ¹ H NMR (500 MHz, DMSO-d6) δ 7.80 - 7.74 (m, 6H), 7.69 (d, 2H), 7.44 - 7.33 (m, 8H), 7.30 - 7.24 ( m, 4H), 7.06 - 6.80 (m, 36H), 6.71 - 6.63 (m, 2H), 6.56 (m, 2H), 6.30 - 6.28 (m, 2H), 5.70 (dd, 2H), 5.17 (dd, 2H)

Synthesis example A-5. Preparation of Compound H-5

In Synthesis Example A-4, instead of 2,2'-bis(4-fluorophenylamino)-9,9'-spirobi[9 H -fluorene], 2,2'-bis(3,4-difluorine) Lophenylamino)-9,9'-spirobi[9 H -fluorene] (2,2'-Bis(3,4-difluorophenylamino)-9,9'-spirobi[9 H -fluorene]) Compound H-5 was prepared in the same manner as Synthesis Example A-4 except that. The synthesis of the compound was confirmed through LC-MS and NMR. MS: [M+H] ⁺ = 1475

NMR measurements of compound H-5: ¹ H NMR (500 MHz, DMSO-d6) δ 7.79 - 7.73 (m, 6H), 7.69 - 7.66 (m, 2H), 7.44 - 7.40 (m, 6H), 7.36 - 7.22 (m, 8H), 7.08 - 6.85 (m, 22H), 6.85 - 6.67 (m, 10H), 6.71 - 6.63 (m, 2H), 6.58 - 6.55 (m, 2H), 6.26 (m, 2H), 5.70 (dd, 2H), 5.17 (dd, 2H)

< Synthesis example B. Preparation of ionic compounds>

Synthesis example B-1. Preparation of ionic compound D-A

Add 1-bromo-2,3,5,6-tetrafluoro-4-vinylbenzene (2 g, 7.8428 mmol) to 20 mL of THF in a 50 mL round bottom flask and stir for 30 minutes at -78°C. did. n-BuLi in hexane (3.45 mL, 8.6271 mmol, 2.5 M) was slowly added to the solution and stirred at -78°C for 30 minutes. BCl ₃ (2.6 mL, 2.6142 mmol, 1 M in heptane solution) was added to the reaction solution at -78°C over 15 minutes. The reaction solution was stirred for a day while slowly raising the temperature to room temperature, and then 30 mL of water was added. The synthetic material was extracted with ethyl acetate (EA) (10 mL, 3 times), and all solvents were removed. Water was completely removed using benzene through Dean-stock, and the solid was filtered to prepare 800 mg of Compound B-1. (Yield: 43%)

Add compound B-1 (400 mg, 0.5569 mmol), diphenyliodonium chloride (176 mg, 0.5569 mmol), 10 mL of H ₂ O, and 10 mL of acetone to a 25 mL round bottom flask and stir vigorously for 30 minutes. did. It was extracted using dichloromethane, the solvent was removed, and it was dried. After removing all solvents, water was completely removed using benzene through Dean-stock, and the solid was filtered to prepare 340 mg of the target compound DA. (Yield: 28%) The synthesis of the compound was confirmed through LC-MS and NMR.

MS: [M-H]- = 711 (negative mode)

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

Figure 6 shows the NMR measurement results of compound D-A.

Synthesis example B-2. Preparation of ionic compound D-B

Mg (193 mg, 7.9208 mmol), I ₂ (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 under the round bottom flask, and the mixture was stirred for one day. The reaction solution turned black and it was confirmed 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. Na ₂ CO ₃ (0.1 M, 80 mL, 8.0 mmol) was slowly added to the reaction solution. The organic solvent was extracted using EA, and the remaining water was removed with MgSO ₄ . Additionally, benzene was distilled using Dean-stock to remove remaining water and impurities. When about 10 mL of solvent remained, the solution was cooled and filtered to prepare 1.6 g of Compound B-2. (Yield: 64%)

Compound B-2 (100 mg, 0.1567 mmol), 10 mL of distilled water, and Ph ₂ ICl (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 was formed. The precipitate was filtered and dried to prepare 140 mg of compound DB. (Yield: 100%) The synthesis of the compound was confirmed through LC-MS and NMR.

MS: [M-H]- = 615 (negative mode)

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

Figure 7 shows the NMR measurement results of compound D-B.

<Preparation of ink composition>

Manufacturing example 1. Preparation of ink composition 1.

Compound H-1 and Compound D-A prepared in the above synthesis example were mixed at a weight ratio of 8:2. Thereafter, 2.0 wt% was added to a mixed solvent containing 10 wt%, 15 wt%, and 75 wt% of the first solvent, 4-butylbiphenyl, the second solvent, dibutyl adipate, and the third solvent, butyl benzoate, respectively. A mixture of Compound H-1 and Compound D-A was added to each concentration. Ink composition 1 was prepared by completely dissolving the mixed solution by stirring for 24 hours.

Manufacturing example 2 to 58. Preparation of ink compositions 2 to 58

Ink compositions 2 to 58 were prepared in the same manner as Preparation Example 1, except that compounds listed in Table 1 below were used as Compound H-1, Compound D-A, and the first and second solvents, respectively.

The structures of the host compounds H-1 to H-5, dopant compounds D-A, D-B, and the second solvent used in Table 1 below are as follows.

* Hole injection layer host compound (HIL HOST)

* Hole injection layer dopant compound (HIL DOPANT)

*Second solvent

ink composition HIL HOST HIL DOPANT first solvent secondary solvent tertiary solvent One H-1 D-A 4-Butylbiphenyl Dibutyl adipate Butylbenzoate 2 H-2 D-B 4-Butylbiphenyl Dibutyl adipate Butylbenzoate 3 H-4 D-A 4-Butylbiphenyl Dibutyl adipate Butylbenzoate 4 H-5 D-B 4-Butylbiphenyl Dibutyl adipate Butylbenzoate 5 H-1 D-B 4-Butylbiphenyl 2-Butoxyethylheptanoate Butylbenzoate 6 H-2 D-A 4-Butylbiphenyl 2-Butoxyethylheptanoate Butylbenzoate 7 H-4 D-A 4-Butylbiphenyl 2-Butoxyethylheptanoate Butylbenzoate 8 H-3 D-B 4-Butylbiphenyl 2-Butoxyethylheptanoate Butylbenzoate 9 H-4 D-A 4-Butylbiphenyl 2-Butoxyethylheptanoate Butylbenzoate 10 H-1 D-B 4-Butylbiphenyl Diisobutyl adipate Butylbenzoate 11 H-2 D-A 4-Butylbiphenyl Diisobutyl adipate Butylbenzoate 12 H-4 D-A 4-Butylbiphenyl Diisobutyl adipate Butyl Benzoate 13 H-4 D-B 4-Butylbiphenyl Diisobutyl adipate Butylbenzoate 14 H-5 D-A 4-Butylbiphenyl Diisobutyl adipate Butylbenzoate 15 H-2 D-A 4-Butylbiphenyl Dibutylsuccinate Butylbenzoate 16 H-2 D-B 4-Butylbiphenyl Dibutylsuccinate Butylbenzoate 17 H-3 D-A 4-Butylbiphenyl Dibutylsuccinate Butylbenzoate 18 H-3 D-B 4-Butylbiphenyl Dibutylsuccinate Butylbenzoate 19 H-4 D-A 4-Butylbiphenyl Dibutylsuccinate Butylbenzoate 20 H-4 D-B 4-Butylbiphenyl Dibutylsuccinate Butylbenzoate 21 H-5 D-A 4-Butylbiphenyl Dibutylsuccinate Butylbenzoate 22 H-2 D-B 4-Butylbiphenyl Ethyl dodecanoate Butylbenzoate 23 H-3 D-A 4-Butylbiphenyl Ethyl dodecanoate Butylbenzoate 24 H-4 D-B 4-Butylbiphenyl Ethyl dodecanoate Butylbenzoate 25 H-1 D-A 4-Butylbiphenyl Hexylpiperidine-1-carboxylate Butylbenzoate 26 H-1 D-B 4-Butylbiphenyl Hexylpiperidine-1-carboxylate Butylbenzoate 27 H-2 D-A 4-Butylbiphenyl Hexylpiperidine-1-carboxylate Butyl Benzoate 28 H-5 D-B 4-Butylbiphenyl Hexylpiperidine-1-carboxylate Butylbenzoate 29 H-2 D-A 4-Butylbiphenyl Ethyl 3-(dibutylamino)propanoate Butylbenzoate 30 H-3 D-B 4-Butylbiphenyl Ethyl 3-(dibutylamino)propanoate Butylbenzoate 31 H-4 D-A 4-Butylbiphenyl Ethyl 3-(dibutylamino)propanoate Butylbenzoate 32 H-4 D-B 4-Butylbiphenyl Ethyl 3-(dibutylamino)propanoate Butylbenzoate 33 H-5 D-A 4-Butylbiphenyl Ethyl 3-(dibutylamino)propanoate Butylbenzoate 34 H-5 D-B 4-Butylbiphenyl Ethyl 3-(dibutylamino)propanoate Butylbenzoate 35 H-1 D-B 4-Butylbiphenyl 3,5-dibutylpyridine Butylbenzoate 36 H-3 D-B 4-Butylbiphenyl 3,5-dibutylpyridine Butylbenzoate 37 H-4 D-A 4-Butylbiphenyl 3,5-dibutylpyridine Butylbenzoate 38 H-5 D-A 4-Butylbiphenyl 3,5-dibutylpyridine Butylbenzoate 39 H-2 D-A 4-Butylbiphenyl 1,9-Noneindthiol Butylbenzoate 40 H-3 D-A 4-Butylbiphenyl 1,9-Noneindthiol Butylbenzoate 41 H-5 D-A 4-Butylbiphenyl 1,9-Noneindthiol Butylbenzoate 42 H-5 D-B 4-Butylbiphenyl 1,9-Noneindthiol Butylbenzoate 43 H-2 D-A 4-Butylbiphenyl 5-hexyltetrahydrofuran-3-ylacetate Butylbenzoate 44 H-4 D-A 4-Butylbiphenyl 5-hexyltetrahydrofuran-3-ylacetate Butylbenzoate 45 H-5 D-B 4-Butylbiphenyl 5-hexyltetrahydrofuran-3-ylacetate Butylbenzoate 46 H-1 D-A dimethyl phthalate 2-Butoxyethylheptanoate Butylbenzoate 47 H-2 D-A dimethyl phthalate 2-Butoxyethylheptanoate Butylbenzoate 48 H-4 D-B dimethyl phthalate 2-Butoxyethylheptanoate Butylbenzoate 49 H-5 D-A dimethyl phthalate 2-Butoxyethylheptanoate Butylbenzoate 50 H-1 D-B 4-(2-acetoxyethoxy)toluene Ethyl dodecanoate Butylbenzoate 51 H-2 D-A 4-(2-acetoxyethoxy)toluene Ethyl dodecanoate Butylbenzoate 52 H-3 D-B 4-(2-acetoxyethoxy)toluene Ethyl dodecanoate Butylbenzoate 53 H-4 D-A 4-(2-acetoxyethoxy)toluene Ethyl dodecanoate Butylbenzoate 54 H-5 D-A 4-(2-acetoxyethoxy)toluene Ethyl dodecanoate Butylbenzoate 55 H-2 D-A 4-Butylbiphenyl Phenethylpropionate Butylbenzoate 56 H-4 D-B 4-Butylbiphenyl p-tolyl octanate Butylbenzoate 57 H-2 D-A Benzyl benzoate Dibutylsuccinate Butylbenzoate 58 H-4 D-B 1-methoxynaphthalene Dibutylsuccinate Butylbenzoate

< Experiment example 1>

Example 1-1.

After printing the ink composition 1 on an ITO substrate with a bank formed by an inkjet method, the printed substrate is placed in a vacuum chamber, and the decompression time from normal pressure to 2x10 ^-2 torr is 60 seconds, and from 2x10 ^-2 torr to 2x10 The decompression time to ^-6 torr was 180 seconds and dried at room temperature. After drying, the thin film was cured by heat treatment for 1 hour in an N ₂ atmosphere and at 230°C on a hot plate. Using Bruker's Optical profiler (model name: ContourGT-I), an optical thickness measuring device, the 10-point average roughness (flatness, Rz) was measured at a size of 40μm x 40μm inside the pixel contained in the cured thin film, and the results were measured in Table 2 below. It is described in .

Example 1-2 to 1-24 and Comparative example 1-1 to 1 -30.

It was prepared in the same manner as Example 1-1 except that the ink composition shown in Table 2 below was used instead of Ink Composition 1.

ink composition Flatness Rz
(nm) Example 1-1 One 19.8 Example 1-2 2 5.6 Example 1-3 3 3.1 Example 1-4 4 13.5 Examples 1-5 5 7.5 Example 1-6 6 17.8 Example 1-7 7 13.4 Examples 1-8 8 14.3 Example 1-9 9 11.2 Examples 1-10 10 11.0 Example 1-11 11 18.0 Examples 1-12 12 12.7 Example 1-13 13 14.3 Example 1-14 14 3.4 Example 1-15 15 5.9 Example 1-16 16 5.8 Example 1-17 17 7.0 Example 1-18 18 7.4 Example 1-19 19 8.2 Examples 1-20 20 11.3 Example 1-21 21 4.4 Example 1-22 22 9.8 Example 1-23 23 10.4 Example 1-24 24 13.0 Comparative Example 1-1 25 22.5 Comparative Example 1-2 26 45.3 Comparative Example 1-3 27 35.5 Comparative Example 1-4 28 34.1 Comparative Example 1-5 29 62.9 Comparative Example 1-6 30 61.7 Comparative Example 1-7 31 41.0 Comparative Example 1-8 32 28.6 Comparative Example 1-9 33 23.1 Comparative Example 1-10 34 32.7 Comparative Example 1-11 35 40.0 Comparative Example 1-12 36 28.8 Comparative Example 1-13 37 45.4 Comparative Example 1-14 38 47.4 Comparative Example 1-15 39 44.0 Comparative Example 1-16 40 36.7 Comparative Example 1-17 41 68.8 Comparative Example 1-18 42 27.2 Comparative Example 1-19 43 34.9 Comparative Example 1-20 44 66.2 Comparative Example 1-21 45 51.8 Comparative Example 1-22 46 30.8 Comparative Example 1-23 47 41.8 Comparative Example 1-24 48 35.5 Comparative Example 1-25 49 29.7 Comparative Example 1-26 50 25.4 Comparative Example 1-27 51 38.7 Comparative Example 1-28 52 40.9 Comparative Example 1-29 53 29.5 Comparative Example 1-30 54 33.4 Comparative Example 1-31 55 27.4 Comparative Example 1-32 56 29.5 Comparative Example 1-33 57 26.1 Comparative Example 1-34 58 25.2

As shown in Table 2, examples using an ink composition according to an embodiment of the present specification have a flatness of 20 nm or less, and comparative examples using an ink composition not corresponding to the present specification have a flatness of 20 nm. It was confirmed that it had an exceeding value. Specifically, Examples 1-1 to 1-24 using the ink composition according to an embodiment of the present specification showed a small flatness of 20 nm or less, so it can be confirmed that pixels are formed uniformly. Accordingly, factors affecting the interference conditions of light emitted depending on the thickness of the organic material layer used in the organic light-emitting device are reduced, and excellent light-emitting and/or coloring effects can be expected. On the other hand, Comparative Examples 1-1 to 1-21, 1-31 and 1-32 in which a solvent other than Formula B was used as the second solvent, and Comparative Example 1- in which a solvent other than Formula A was used as the first solvent. Since the flatness of pixels 22 to 1-30, 1-33, and 1-34 all show large values exceeding 20 nm, it can be confirmed that pixels of non-uniform thickness were formed.

< Experiment example 2>

Example 2-1.

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 700 Å and on which hydrophobic banks were patterned was washed with distilled water for 30 minutes and dried on a hot plate at 230°C for 10 minutes. Ink composition 1 of Table 1 was inkjet printed on a bank-patterned cleaned substrate and heat treated at 230°C for 30 minutes to form a hole injection layer with a thickness of 30 nm. On the hole injection layer, an ink containing an α-NPD compound dissolved in cyclohexylbenzene at the following concentration of 2 wt% was inkjet printed to form a hole transport layer with a thickness of 40 nm. After being transferred to a vacuum deposition machine, the following AND compound and the following DPAVBi compound were vacuum deposited on the hole transport layer at a weight ratio of 20:1 (AND:DPAVBi) to a thickness of 20 nm to form a light emitting layer. The following BCP compound was vacuum deposited on the light emitting layer to a thickness of 35 nm to form an electron injection and transport layer. Organic light-emitting device 1 was manufactured by depositing LiF to a thickness of 1 nm and aluminum to a thickness of 100 nm to form a cathode on the electron injection and transport layer.

Example 2-2 to 2-24.

Organic light-emitting devices 2 to 24 were manufactured using the ink compositions in Table 3 below instead of ink composition 1 in Example 2-1.

ink composition Example 2-1 One Example 2-2 2 Example 2-3 3 Example 2-4 4 Example 2-5 5 Example 2-6 6 Example 2-7 7 Example 2-8 8 Example 2-9 9 Example 2-10 10 Example 2-11 11 Example 2-12 12 Example 2-13 13 Example 2-14 14 Example 2-15 15 Example 2-16 16 Example 2-17 17 Example 2-18 18 Example 2-19 19 Example 2-20 20 Example 2-21 21 Example 2-22 22 Example 2-23 23 Example 2-24 24

It was confirmed that the organic light emitting devices manufactured in Examples 2-1 to 2-24 were driven. Through this, it was confirmed that the ink composition according to the embodiment of the present invention is applicable to organic light-emitting devices.

1': pixel
101: substrate
201: first electrode
301: hole injection layer
401: hole transport layer
501: light emitting layer
601: Electron injection and transport layer
701: second electrode
A: Flatness measurement area of pixel

Claims (20)

A compound represented by the following formula (1);
A first solvent represented by the following formula (A); and
An ink composition comprising a second solvent represented by the following formula B:
[Formula 1]

[Formula A]

[Formula B]

In Formula 1, A and B,
La is a substituted or unsubstituted divalent hydrocarbon ring group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L10 and L11 are the same or different from each other and are each independently a substituted or unsubstituted arylene group,
L20 and L21 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
X1 and X2 are the same or different from each other and are each independently a curable group,
R1 to R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r1 and r2 are each integers from 0 to 7, and when r1 and r2 are each 2 or more, 2 or more substituents in parentheses are the same or different from each other,
r3 and r4 are each integers from 0 to 4, and when r3 and r4 are each 2 or more, 2 or more substituents in parentheses are the same or different from each other,
f1 is the number of bonding positions where substituents can be bonded to 0 to Ar1,
f2 is the number of bonding positions where a substituent can be bonded to 0 to Ar2,
f3 and f4 are each integers from 0 to 5, r3+f3 is 5 or less, r4+f4 is 5 or less, f1+f2+f3+f4 is an integer of 1 or more,
Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; hydroxyl group; ether group; carbonyl group; ester group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted amine group,
L1 and L2 are the same or different from each other and are each independently directly bonded; -O-; Or a substituted or unsubstituted alkylene group,
Z1 and Z2 are the same or different from each other and are each independently a substituted or unsubstituted alkyl group,
a1 is 0 or 1,
l1 and l2 are each integers of 1 to 10, and when l1 and l2 are each 2 or more, 2 or more substituents in parentheses are the same or different from each other. In claim 1,
An ink composition wherein the curable group has any one of the following structures:

In the above structure,
R32 and R34 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,
L31 to L38 are the same or different from each other and are each independently directly bonded; -O-; Substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,
l34 to l38 are integers from 1 to 10, and when l34 to l38 are each 2 or more, two or more substituents in parentheses are the same or different from each other,

is a site bound to Formula 1 above. In claim 1,
The ink composition of Formula 1 is represented by the following Formula 1-1:
[Formula 1-1]

In Formula 1-1,
The definitions of Ar1, Ar2, L10, L11, L20, L21, La, X1, X2, R1 to R4, r1 to r4, and f1 to f4 are the same as in Formula 1. In claim 1,
The ink composition wherein La is any one of the following structures:

In the above structure,
R10 to R31 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
n10 to n21 are each integers from 1 to 4, n22, n23, n28 and n29 are each integers from 1 to 3, n24 and n25 are each integers from 1 to 7, n26 is an integer from 1 to 8, and n27 is an integer from 1 to 6, and when n10 to n29 are each 2 or more, 2 or more substituents in parentheses are the same or different from each other,

is the site bound to Chemical Formula 1. In claim 1,
Y1 to Y10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or an ink composition containing a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms. In claim 1,
The formula B is an ink composition represented by any one of the following formulas B-1 to B-3:
[Formula B-1]

[Formula B-2]

[Formula B-3]

In the above formulas B-1 to B-3,
Z1 and Z2 are the same or different from each other and are each independently a substituted or unsubstituted alkyl group,
L1' and L2 are the same or different from each other, and each independently represents a substituted or unsubstituted alkylene group. In claim 1,
Formula 1 is an ink composition having any one of the following structures:

. In claim 1,
An ink composition wherein the first solvent represented by Formula A is any one or a mixture of two or more selected from the group consisting of the following structures:

. In claim 1,
An ink composition wherein the second solvent represented by Formula B is any one or a mixture of two or more selected from the group consisting of the following structures:

. In claim 1,
The ink composition further includes a third solvent represented by the following formula C:
[Formula C]

In the formula C,
G1 and G2 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
g1 is an integer from 1 to 5, and when g1 is 2 or more, the substituents in parentheses are the same or different from each other. In claim 1,
The ink composition further includes an ionic compound containing an anionic group represented by the following formula (2):
[Formula 2]

In Formula 2,
At least one of R201 to R220 is F; Cyano group; Or a substituted or unsubstituted fluoroalkyl group,
At least one of the remaining R201 to R220 is a curable group,
The remaining R201 to R220 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; nitro group; Cyano group; amino group; -OR221; -SR222; -SO ₃ R223; -COOR224; -OC(O)R225; -C(O)NR226R227; -C(O)R228; 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 a substituted or unsubstituted heterocyclic group,
R221 to R228 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted alkyl group. In claim 11,
Formula 2 is an ink composition having any one of the following structures:

In the above structure,
n1 is an integer from 1 to 3, m1 is an integer from 1 to 3, n1+m1=4,
n2 is an integer from 0 to 3, m2 is an integer from 1 to 4, n2+m2=4,
M1 is deuterium; halogen group; nitro group; Cyano group; amino group; -OR221; -SR222; -SO ₃ R223; -COOR224; -OC(O)R225; -C(O)NR226R227; -C(O)R228; 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 a substituted or unsubstituted heterocyclic group,
R221 to R228 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,
i is an integer from 1 to 4, and when i is 2 or more, 2 or more M1s are the same or different from each other. In claim 11,
The ionic compound further includes a cationic group, and the cationic group is a monovalent cationic group, an onium compound, or any of the following structures:

In the above structure,
Q30 to Q105 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; nitro group; halogen group; hydroxyl group; -COOR250; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or it is a hardening stage,
R250 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,
x is an integer from 0 to 10,
p1 is 1 or 2, q1 is 0 or 1, and p1+q1=2. In claim 11,
An ink composition wherein the ionic compound is any one of the following formulas D-1 to D-37:




. In claim 1,
The ink composition is for forming one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer. A pixel comprising the ink composition or a cured product thereof according to any one of claims 1 to 15. In claim 16,
A pixel wherein the flatness of the pixel is 20 nm or less. An organic layer containing pixels according to claim 16. first electrode;
second electrode; and
Comprising one or more organic material layers provided between the first electrode and the second electrode,
An organic light-emitting device wherein at least one layer of the organic material layers is the organic material layer according to claim 18. In claim 19,
The organic material layer includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer,
An organic light emitting device wherein at least one layer selected from the group consisting of the hole injection layer, hole transport layer, hole injection and transport layer, and electron blocking layer includes the ink composition or a cured product thereof.