KR102128646B1 - Compound, coating composition comprising the same, organic light emitting device using the same and method of manufacturing the same - Google Patents

Abstract

The present specification relates to a compound of Formula 1, a coating composition comprising the compound of Formula 1, an organic light emitting device using the same, and a method of manufacturing the same.

Description

Compound, coating composition comprising the same, organic light emitting device using same, and manufacturing method thereof {COMPOUND, COATING COMPOSITION COMPRISING THE SAME, ORGANIC LIGHT EMITTING DEVICE USING THE SAME AND METHOD OF MANUFACTURING THE SAME}

The present specification relates to a compound, a coating composition containing the compound, an organic light emitting device formed using the coating composition, and a method for manufacturing the same.

The organic light emission phenomenon is an example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of the organic light emission phenomenon is as follows. When an organic layer is placed between the anode and the cathode, when an electric current is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. The electrons and holes injected into the organic layer recombine to form excitons, and the excitons fall back to the ground state to emit light. An organic light emitting device using this principle may be generally composed of a cathode and an anode, and an organic material layer disposed therebetween, such as a hole injection layer, a hole transport layer, an emission layer, and an organic material layer including an electron transport layer.

Conventionally, a deposition process has been mainly used to manufacture an organic light emitting device. However, when manufacturing an organic light emitting device by a deposition process, there is a problem that a lot of material loss occurs. In order to solve this, a technique of manufacturing a device through a solution process that can increase production efficiency by reducing material loss It is being developed, and the development of materials that can be used in solution processing is required.

The material used in the organic light emitting device for the solution process should have the following properties.

First, it must be possible to form a homogeneous solution that can be stored. In the case of a commercially available material for a deposition process, the crystallinity is good, so it is highly likely that the concentration gradient of the solution changes or a defective device is formed depending on the storage period because the crystal is easily caught even if it is not soluble in a solution or forms a solution.

Second, the layers in which the solution process is performed must be resistant to solvents and materials used in the process of forming another layer, and it is required to have excellent current efficiency and excellent life characteristics when manufacturing an organic light emitting device.

Korea Patent Publication No. 2012-0112277

It is an object of the present specification to provide a compound usable in an organic light emitting device for solution processing and an organic light emitting device including the same.

It provides a compound represented by the following formula (1).

[Formula 1]

In Chemical Formula 1,

Ar ₁ to Ar ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heterocyclic group, or may combine with an adjacent substituent to form an aromatic hydrocarbon ring,

s1 and s2 are each an integer of 0 to 6, and when s1 and s2 are each 2 or more, the substituents in parentheses are the same or different from each other,

s3 and s4 are each an integer from 0 to 4, and when s3 and s4 are each 2 or more, the substituents in parentheses are the same or different from each other,

L is a substituted or unsubstituted arylene group,

n is 1 or 2,

When n is 2, L is the same as or different from each other,

L ₁ and L ₄ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

L ₇ and L ₈ are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

L ₂ and L ₃ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted alkenylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

L ₅ and L ₆ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted alkenylene group; Or a substituted or unsubstituted arylene group,

Y ₁ to Y ₆ are the same as or different from each other, and each independently hydrogen; Or a functional group capable of crosslinking by heat or light, and at least one of Y ₁ to Y ₆ is a functional group crosslinkable by heat or light.

The present specification provides a coating composition comprising the compound.

The specification also includes a cathode; Anode; And one or more organic material layers provided between the cathode and the anode, and at least one layer of the organic material layer includes a cured product of the coating composition, and the cured product of the coating composition is used for heat treatment or light treatment. It provides an organic light emitting device that is in a cured state.

Finally, the present specification includes preparing a substrate; Forming a cathode or anode on the substrate; Forming one or more organic material layers on the cathode or anode; And forming an anode or a cathode on the organic material layer, and forming the organic material layer includes forming one or more organic material layers using the coating composition. do.

The compound according to an exemplary embodiment of the present invention is capable of a solution process, enables a large area of a device, can be used as a material for an organic material layer of an organic light emitting device, and provides low driving voltage, high luminous efficiency and high lifespan characteristics. Can.

In addition, the compound according to an exemplary embodiment of the present invention contains a functional group capable of crosslinking by heat or light, and by containing oxygen (O) and fluorine (F) in the compound, solubility (solvent) and coating properties for organic solvents It has the advantage of being excellent.

1 shows an example of an organic light emitting device according to an exemplary embodiment of the present specification.
2 is a diagram showing an MS spectrum of Compound 1 prepared in Preparation Example 1.
3 is a diagram showing a current density-driving voltage value according to Examples and Comparative Examples.
4 is a diagram showing luminance-time values according to examples and comparative examples.

Hereinafter, the present specification will be described in detail.

One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[Formula 1]

In Chemical Formula 1,

Ar ₁ to Ar ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heterocyclic group, or may combine with an adjacent substituent to form an aromatic hydrocarbon ring,

s1 and s2 are each an integer of 0 to 6, and when s1 and s2 are each 2 or more, the substituents in parentheses are the same or different from each other,

s3 and s4 are each an integer from 0 to 4, and when s3 and s4 are each 2 or more, the substituents in parentheses are the same or different from each other,

L is a substituted or unsubstituted arylene group,

n is 1 or 2,

When n is 2, L is the same as or different from each other,

L ₁ and L ₄ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

L ₇ and L ₈ are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

L ₂ and L ₃ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted alkenylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

L ₅ and L ₆ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted alkenylene group; Or a substituted or unsubstituted arylene group,

Y ₁ to Y ₆ are the same as or different from each other, and each independently hydrogen; Or a functional group capable of crosslinking by heat or light, and at least one of Y ₁ to Y ₆ is a functional group crosslinkable by heat or light.

The compound according to an exemplary embodiment of the present invention has the advantage of being excellent in solvability and coating properties by including oxygen (O). Considering that the conventional arylamine compound has low solubility in an organic solvent, the intermediate oxygen (O) linker can be dissolved in the organic solvent more flexibly by increasing the flexibility of the material to enable rotation. In addition, since these properties have a large degree of packing when crosslinked, bonds between compounds are well formed to enhance the coating properties. In addition, when the compound of Formula 1 contains fluorine (F), when used together with a dopant containing fluorine (F), the affinity between the dopant containing fluorine is excellent, so that the dopant and host are well bonded to other layers. Movement can be controlled.

In the present specification, when a member is positioned “on” another member, this includes not only the case where one member is in contact with the other member, but also the case where another member is present between the two members.

In the present specification, when a part “includes” a certain component, it means that the component may further include other components, not to exclude other components, unless otherwise stated.

In the present specification, the term “a combination of these” included in the expression of the marki form means two or more mixed or combined states selected from the group consisting of the components described in the expression of the marki form, wherein It means to include one or more selected from the group of components.

In one embodiment of the present specification, the compound of Formula 1 is preferably a compound having solubility in a suitable organic solvent.

As used herein, “a functional group crosslinkable by heat or light” may mean a reactive substituent that crosslinks between compounds by exposure to heat and/or light. Cross-linking may be generated by heat-radiation or light irradiation, carbon-carbon multiple bonds, and radicals formed as the cyclic structures are decomposed and linked.

In one embodiment of the present specification, in the case of a compound containing a functional group capable of crosslinking by heat or light, an organic light emitting device can be manufactured by a solution coating method, which is economical in time and cost.

In addition, when a coating layer is formed by using a coating composition containing a compound containing a functional group capable of crosslinking by heat or light, since the functional group crosslinkable by heat or light is crosslinked by heat or light, the coating layer When the additional layer is stacked on the top, the fluorene derivative contained in the coating composition is prevented from being washed off by the solvent, and the additional layer can be stacked on the top while maintaining the coating layer.

In addition, when a functional layer capable of crosslinking by heat or light forms a crosslink to form a coating layer, chemical resistance to the solvent of the coating layer increases, and a film retention rate is high.

In addition, in the case of the compound according to the exemplary embodiment of the present specification, an organic light emitting device may be manufactured by a solution coating method, and thus a large area of the device may be possible.

According to an exemplary embodiment of the present specification, in the case of a compound formed by cross-linking by heat treatment or light irradiation, a plurality of compounds of Formula 1 are cross-linked and provided in the organic light emitting device in the form of a thin film, thereby having excellent thermal stability.

In addition, since the compound according to an exemplary embodiment of the present specification includes an amine structure in the core structure, it may have an appropriate energy level and a band gap as a hole injection, hole transport or light emitting material in the organic light emitting device. In addition, by controlling the substituents of the compound of Formula 1 according to an exemplary embodiment of the present specification, it is possible to finely adjust an appropriate energy level and a band gap, and improve the interfacial properties between organic materials, resulting in low driving voltage and high luminous efficiency. It is possible to provide an organic light-emitting device having.

Hereinafter, the substituents of the present specification will be described in detail.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification,

Means a site that is attached to another substituent or linkage.

In the present specification, the term “substitution” means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where the substituent is replaceable. When two or more are substituted, two or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" in this specification is deuterium; Halogen group; Nitrile group; Hydroxy group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkoxy groups; Alkenyl group; Aryl group; Alkylamine groups; Arylamine group; Heteroarylamine group; And substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups, or substituted or unsubstituted with two or more substituents among the exemplified substituents. For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

In the present specification, the halogen group is fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).

In the present specification, the silyl group may be represented by the formula of -SiR _a R _b R _c , wherein R _a , R _b and R _c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. Does not.

In the present specification, the boron group may be represented by the formula of -BR _a R _b , wherein R _a and R _b are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group is specifically, a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.

In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but may be 1 to 30, and according to an exemplary embodiment, the number of carbon atoms of the alkyl group may be 1 to 20. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group are methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group , Isopentyl group, neopentyl group, tert-pentyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, hexyl group, isohexyl group, 4-methylhexyl group, 5- Methylhexyl group, heptyl group, and the like, but are not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, and may be 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. Specific examples of the cycloalkyl group are cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclo Hexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but may be 1 to 20 carbon atoms. Specific examples of the alkoxy group include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, i-propyloxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n -Pentyloxy group, neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n -It may be a decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, but is not limited thereto.

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but may be 2 to 30, and according to an exemplary embodiment, the alkenyl group may have 2 to 20 carbon atoms. Specific examples of the alkenyl group include a vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3 -Methyl-1-butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2 -Phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, and the like. It is not limited.

In the present specification, the aryl group is not particularly limited, but may be 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure.

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

Spirofluorenyl groups, such as

(9,9-dimethylfluorenyl group), and

It may be a substituted fluorenyl group, such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.

In the present specification, the heterocyclic group is a heteroatom as a heterocyclic group including one or more of N, O, P, S, Si, and Se, and the number of carbon atoms is not particularly limited, but may be 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to another exemplary embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include pyridyl group, pyrrol group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, oxazole group, isooxazole group, thiazole group, isothiazole group, Triazole group, oxadiazole group, thiadiazole group, dithiazole group, tetrazole group, pyranyl group, thiopyranyl group, pyrazinyl group, oxazinyl group, thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, quie Nolinyl group, isoquinolinyl group, quinolyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, acridil group, xanthenyl group, phenanthridinyl group, diazanaphthalenyl group, triazindenyl group, indole group , Indolinyl group, indolizinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group , Benzofuranyl group, dibenzothiophenyl group, dibenzofuranyl group, carbazole group, benzocarbazole group, dibenzocarbazole group, indolocarbazole group, indenocarbazole group, phenazinyl group, imidazopyridine group, phenoxazinyl group , Phenanthridine group, phenanthroline group, phenothiazine group, imidazopyridine group, imidazophenanthridine group. Benzoimidazoquinazoline groups, benzoimidazophenanthridine groups, and the like, but are not limited to these.

In the present specification, the number of carbon atoms in the alkylamine group is not particularly limited, but is preferably 1 to 40. Specific examples of the alkylamine group are methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine Groups, diphenylamine groups, phenylnaphthylamine groups, ditolylamine groups, phenyltolylamine groups, triphenylamine groups, and the like, but are not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including the two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, and 9-methyl-anthra Senilamine, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole and triphenyl amine group, but are not limited thereto.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroarylamine group including two or more heterocyclic groups may include a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group simultaneously.

In the present specification, a description of the aforementioned heterocyclic group may be applied, except that the heteroaryl group is aromatic.

In this specification, "adjacent" A group may mean a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent located closest to the corresponding substituent and the other substituent substituted on the atom in which the substituent is substituted. For example, two substituents substituted at the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as “adjacent” to each other.

In the present specification, the aromatic hydrocarbon ring may be an aromatic condensed ring, and may be selected from examples of the aryl group, except that it is not a monovalent group.

In the present specification, the above description of the aryl group is applied, except that the arylene group is a divalent group.

In the present specification, the description of the aforementioned heterocyclic group is applied except that the divalent heterocyclic group is a divalent group.

In the present specification, the description of the aforementioned alkyl group is applied, except that the alkylene group is a divalent group.

In the present specification, the above description of the alkenyl group is applied, except that the alkenylene group is a divalent group.

In one embodiment of the present specification, Y ₁ to Y ₆ are the same as or different from each other, and each independently hydrogen; Or a functional group capable of crosslinking by heat or light, and at least one of Y ₁ to Y ₆ is a functional group crosslinkable by heat or light.

According to another exemplary embodiment, Y ₁ to Y ₆ are the same as or different from each other, and each independently hydrogen; Or a functional group crosslinkable by heat or light, and two or more of Y ₁ to Y ₆ are functional groups crosslinkable by heat or light.

According to another exemplary embodiment, Y ₁ to Y ₆ are the same as or different from each other, and each independently hydrogen; Or a functional group crosslinkable by heat or light, 2 of Y ₁ to Y ₆ are functional groups crosslinkable by heat or light, and the rest are hydrogen.

In another exemplary embodiment, Y ₅ and Y ₆ are functional groups capable of crosslinking by heat or light, and Y ₁ to Y ₄ are hydrogen.

In another exemplary embodiment, Y ₂ and Y ₃ are functional groups crosslinkable by heat or light, and Y ₁ , Y ₄ , Y ₅ and Y ₆ are hydrogen.

In another exemplary embodiment, Y ₁ and Y ₄ are functional groups capable of crosslinking by heat or light, and Y ₂ , Y ₃ , Y ₅ and Y ₆ are hydrogen.

In another exemplary embodiment, Y ₁ and Y ₆ are functional groups capable of crosslinking by heat or light, and Y ₂ to Y ₅ are hydrogen.

In another exemplary embodiment, Y ₄ and Y ₅ are functional groups capable of crosslinking by heat or light, and Y ₁ , Y ₂ , Y ₃ and Y ₆ are hydrogen.

In another exemplary embodiment, Y ₃ and Y ₅ are functional groups capable of crosslinking by heat or light, and Y ₁ , Y ₂ , Y ₄ and Y ₆ are hydrogen.

In another exemplary embodiment, Y ₂ and Y ₆ are functional groups capable of crosslinking by heat or light, and Y ₁ , Y ₃ , Y ₄ and Y ₅ are hydrogen.

In one embodiment of the present specification, the functional group capable of crosslinking by heat or light is one of the following structures.

In the above structure,

R is hydrogen; Or a substituted or unsubstituted alkyl group,

A ₁ to A ₃ are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, R is hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms.

In another exemplary embodiment, R is hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, R is hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted butyl group; Or a substituted or unsubstituted tert-butyl group.

In another exemplary embodiment, R is hydrogen; Methyl group; Ethyl group; Propyl group; Isopropyl group; Butyl group; Or tert-butyl group.

According to another exemplary embodiment, R is hydrogen.

In one embodiment of the present specification, A ₁ to A ₃ are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted pentyl group; It is a substituted or unsubstituted hexyl group.

In another exemplary embodiment, A ₁ to A ₃ are the same as or different from each other, and each independently a methyl group; Ethyl group; Propyl group; Isopropyl group; Butyl group; tert-butyl group; Pentyl group; Hexyl group.

In one embodiment of the present specification, n is 1 or 2.

In one embodiment of the present specification, L is a substituted or unsubstituted arylene group containing fluorine (F).

In another exemplary embodiment, L is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms containing fluorine (F).

According to another exemplary embodiment, L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms containing fluorine (F).

In another exemplary embodiment, L is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms containing fluorine (F).

In one embodiment of the present specification, L is represented by the following Chemical Formula 2.

[Formula 2]

In Chemical Formula 2,

R ₁ to R ₄ are the same as or different from each other, and each independently hydrogen; Or fluorine (F), and at least one of R ₁ to R ₄ is fluorine (F),

m is 1 or 2, and when m is 2, the substituents in parentheses are the same or different from each other.

In one embodiment of the present specification, R ₁ to R ₄ are the same as or different from each other, and each independently hydrogen; Or fluorine (F), and 2 or more of R ₁ to R ₄ are fluorine (F).

In another exemplary embodiment, R ₁ to R ₄ are fluorine (F).

According to one embodiment of the present specification, R ₁ to R ₄ are any one selected from the following structures.

In one embodiment of the present specification, L ₁ and L ₄ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, L ₁ and L ₄ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

In another exemplary embodiment, L ₁ and L ₄ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent dibenzofuranylene group; Or a substituted or unsubstituted divalent dibenzothiophenylene group.

According to another exemplary embodiment, L ₁ and L ₄ are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Terphenylene group; Naphthylene group; Divalent dibenzofuranyl group; Or a divalent dibenzothiophenyl group.

According to the exemplary embodiment of the present specification, L ₁ and L ₄ are a direct bond or a phenylene group.

In one embodiment of the present specification, L ₇ and L ₈ are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to another exemplary embodiment, L ₇ and L ₈ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted terphenylene group; Or a substituted or unsubstituted naphthylene group.

In another exemplary embodiment, L ₇ and L ₈ are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Terphenylene group; Or a naphthylene group.

According to the exemplary embodiment of the present specification, L ₇ and L ₈ are a direct bond or a phenylene group.

In one embodiment of the present specification, L ₂ and L ₃ are the same as or different from each other, and each independently, a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted alkenylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.

In another exemplary embodiment, L ₂ and L ₃ are the same as or different from each other, and each independently, a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.

According to another exemplary embodiment, L ₂ and L ₃ are the same as or different from each other, and each independently, a direct bond; An arylene group unsubstituted or substituted with an alkyl group or an aryl group; Or a divalent heterocyclic group unsubstituted or substituted with an alkyl group or an aryl group.

In another exemplary embodiment, L ₂ and L ₃ are the same as or different from each other, and each independently, a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

According to another exemplary embodiment, L ₂ and L ₃ are the same as or different from each other, and each independently, a direct bond; An arylene group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group; Or a divalent heterocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group.

In another exemplary embodiment, L ₂ and L ₃ are the same as or different from each other, and each independently, a direct bond; An arylene group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms; Or it is a C2-C30 divalent heterocyclic group substituted or unsubstituted with a C1-C20 alkyl group or a C6-C30 aryl group.

According to another exemplary embodiment, L ₂ and L ₃ are the same as or different from each other, and each independently, a direct bond; An arylene group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms; Or it is a C2-C30 divalent heterocyclic group substituted or unsubstituted with a C1-C10 alkyl group or a C6-C20 aryl group.

In another exemplary embodiment, L ₂ and L ₃ are the same as or different from each other, and each independently, a direct bond; An arylene group having 6 to 30 carbon atoms unsubstituted or substituted with a methyl group, ethyl group, n-propyl group, n-butyl group, phenyl group, biphenyl group, or naphthyl group; Or a divalent heterocyclic group having 2 to 30 carbon atoms, which is unsubstituted or substituted with a methyl group, ethyl group, n-propyl group, n-butyl group, phenyl group, biphenyl group, or naphthyl group.

According to another exemplary embodiment, L ₂ and L ₃ are the same as or different from each other, and each independently, a direct bond; A phenylene group unsubstituted or substituted with a methyl group, ethyl group, n-propyl group, n-butyl group, phenyl group, biphenyl group, or naphthyl group; A biphenylylene group unsubstituted or substituted with a methyl group, ethyl group, n-propyl group, n-butyl group, phenyl group, biphenyl group, or naphthyl group; A naphthylene group unsubstituted or substituted with a methyl group, ethyl group, n-propyl group, n-butyl group, phenyl group, biphenyl group, or naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an n-butyl group, a phenyl group, a biphenyl group, or a naphthyl group; Or a carbazole group unsubstituted or substituted with a methyl group, ethyl group, n-propyl group, n-butyl group, phenyl group, biphenyl group, or naphthyl group.

In one embodiment of the present specification, L ₅ and L ₆ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; A substituted or unsubstituted 2 to 30 alkenylene group; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In another exemplary embodiment, L ₅ and L ₆ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted alkylene group having 1 to 20 carbon atoms; A substituted or unsubstituted 2 to 20 alkenylene group; Or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to another exemplary embodiment, L ₅ and L ₆ are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

In another exemplary embodiment, L ₅ and L ₆ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; Or a substituted or unsubstituted naphthylene group.

According to another exemplary embodiment, L ₅ and L ₆ are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Or a naphthylene group.

In another exemplary embodiment, L ₅ and L ₆ are a direct bond.

In another exemplary embodiment, L ₅ and L ₆ are phenylene groups.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with adjacent substituents to form an aromatic hydrocarbon ring.

In another exemplary embodiment, Ar ₁ and Ar ₂ are the same as or different from each other, and 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 20 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combines with adjacent substituents to form an aromatic hydrocarbon ring.

In another exemplary embodiment, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted n-propyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted n-butyl group; A substituted or unsubstituted t-butyl group; A substituted or unsubstituted pentyl group; A substituted or unsubstituted hexyl group; A substituted or unsubstituted methoxy group; A substituted or unsubstituted ethoxy group; A substituted or unsubstituted vinyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; It is a substituted or unsubstituted dibenzofuran group or a substituted or unsubstituted dibenzothiophenyl group, or combines with adjacent substituents to form an aromatic hydrocarbon ring.

In another exemplary embodiment, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Methyl group; Ethyl group; n-propyl group; Isopropyl group; n-butyl group; t-butyl group; Pentyl group; Hexyl group; Methoxy group; Ethoxy group; Vinyl group; Phenyl group; Chi biphenyl group; Naphthyl group; It is a dibenzofuran group or a dibenzothiophenyl group, or combines with adjacent substituents to form an aromatic hydrocarbon ring.

In another exemplary embodiment, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Methyl group; Ethyl group; n-propyl group; Isopropyl group; n-butyl group; t-butyl group; Pentyl group; Hexyl group; Methoxy group; Ethoxy group; Vinyl group; Phenyl group; Chi biphenyl group; Naphthyl group; It is a dibenzofuran group or a dibenzothiophenyl group, or combines with adjacent substituents to form a benzene ring.

In one embodiment of the present specification, s1 and s2 are each an integer of 0 to 6, and when s1 and s2 are each 2 or more, the substituents in parentheses are the same or different from each other.

According to another exemplary embodiment, s1 and s2 are each an integer of 0 to 3, and when s1 and s2 are each 2 or more, the substituents in parentheses are the same or different from each other.

In another exemplary embodiment, s1 and s2 are integers from 0 to 2, and when s1 and s2 are 2, the substituents in parentheses are the same or different from each other.

In one embodiment of the present specification, s1 is an integer from 0 to 2, and when s1 is 2, two Ar _1s may combine with each other to form an aromatic hydrocarbon ring.

In one embodiment of the present specification, s1 is an integer from 0 to 2, and when s1 is 2, two Ar _1s may combine with each other to form a benzene ring.

In one embodiment of the present specification, s2 is an integer from 0 to 2, and when s2 is 2, two Ar ₂ may be bonded to each other to form an aromatic hydrocarbon ring.

In one embodiment of the present specification, s2 is an integer from 0 to 2, and when s2 is 2, two Ar ₂ may combine with each other to form a benzene ring.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with adjacent substituents to form an aromatic hydrocarbon ring.

In another exemplary embodiment, Ar ₃ and Ar ₄ are the same as or different from each other, and 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 20 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combines with adjacent substituents to form an aromatic hydrocarbon ring.

In another exemplary embodiment, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted n-propyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted n-butyl group; A substituted or unsubstituted t-butyl group; A substituted or unsubstituted pentyl group; A substituted or unsubstituted hexyl group; A substituted or unsubstituted methoxy group; A substituted or unsubstituted ethoxy group; A substituted or unsubstituted vinyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; It is a substituted or unsubstituted dibenzofuran group or a substituted or unsubstituted dibenzothiophenyl group, or combines with adjacent substituents to form an aromatic hydrocarbon ring.

In another exemplary embodiment, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Methyl group; Ethyl group; n-propyl group; Isopropyl group; n-butyl group; t-butyl group; Pentyl group; Hexyl group; Methoxy group; Ethoxy group; Vinyl group; Phenyl group; Chi biphenyl group; Naphthyl group; Dibenzofuran group or dibenzothiophenyl group.

In one embodiment of the present specification, s3 and s4 are each an integer of 0 to 4, and when s3 and s4 are each 2 or more, the substituents in parentheses are the same or different from each other.

According to another exemplary embodiment, s3 and s4 are integers from 0 to 2, and when s3 and s4 are 2, the substituents in parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, the compound of Formula 1 may be any one selected from the following structures.

.

.

The compound according to the exemplary embodiment of the present specification may be prepared by a manufacturing method described later.

For example, the compound of Formula 1 may be prepared by the method described in Preparation Examples below. Substituents can be combined by methods known in the art, and the type, location, or number of substituents can be varied according to techniques known in the art.

In one embodiment of the present specification, there is provided a coating composition comprising the compound of Formula 1 described above.

In one embodiment of the present specification, the coating composition includes the compound of Formula 1 and a solvent.

In one embodiment of the present specification, the coating composition may further include one or two compounds selected from the group consisting of a compound and a polymer compound in which a functional group crosslinkable by heat or light is introduced into a molecule.

In one embodiment of the present specification, the coating composition may further include a compound in which a functional group capable of crosslinking by heat or light is introduced into the molecule. When the coating composition further includes a compound in which a functional group crosslinkable by heat or light is introduced into the molecule, the degree of curing of the coating composition may be further increased.

In one embodiment of the present specification, the molecular weight of a compound in which a functional group capable of crosslinking by heat or light is introduced into a molecule is 1,000 g/mol to 3,000 g/mol.

In one embodiment of the present specification, the coating composition may further include a polymer compound. When the coating composition further includes a polymer compound, ink characteristics of the coating composition may be improved. That is, the coating composition further comprising the polymer compound may provide a suitable viscosity for coating or ink jetting.

In one embodiment of the present specification, the molecular weight of the polymer compound is 10,000 g/mol to 200,000 g/mol.

In one embodiment of the present specification, the polymer compound may further include a crosslinkable functional group.

In one embodiment of the present specification, the coating composition may be liquid. The term "liquid phase" means a liquid state at normal temperature and pressure.

In one embodiment of the present specification, the solvent includes, for example, 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 and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; Aliphatic hydrocarbon-based solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, isosophone, tetralone, decalone, and acetylacetone; Ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyvalent values of 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 derivatives thereof; Alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide-based solvents such as dimethyl sulfoxide; And amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; A solvent such as tetralin is exemplified, but a solvent capable of dissolving or dispersing the compound of Formula 1 according to an exemplary embodiment of the present invention is sufficient, and the solvent is not limited thereto.

In another exemplary embodiment, the solvent may be used alone or as a mixture of two or more solvents.

In one embodiment of the present specification, the coating composition may further include one or more additives selected from the group consisting of a thermal polymerization initiator and a photo polymerization initiator.

In one embodiment of the present specification, the coating composition does not further include a p-doped material.

In one embodiment of the present specification, the coating composition further includes a p-doped material.

In the present specification, the p-doped material may promote thermosetting or photocuring.

In the present specification, the p-doped material means a material that makes the host material have p-semiconductor properties. The p-semiconductor property means a property in which holes are injected or transported at a HOMO (highest occupied molecular orbital) energy level, that is, a property of a material having high hole conductivity.

In one embodiment of the present specification, the p-doped material may be represented by any one of the following Chemical Formulas A to E, but is not limited thereto.

[Formula A]

[Formula B]

[Formula C]

[Formula D]

[Formula E]

In the present specification, the p-doped material is sufficient as long as it is a material having p-semiconductor properties, and one or two or more types can be used, and the type of the p-doped material is not limited.

In one embodiment of the present specification, the content of the p-doped material is 0% to 50% by weight based on the compound of Formula 1 above.

In one embodiment of the present specification, the content of the p-doped material includes 0 to 30% by weight based on the total solid content of the coating composition. In one embodiment of the present specification, the content of the p-doped material preferably includes 1 to 30% by weight based on the total solid content of the coating composition, and in another embodiment, the p-doped material It is more preferable that the content of 1 to 20% by weight based on the total solid content of the coating composition.

In another embodiment, the coating composition is a single molecule containing a functional group crosslinkable by heat or light; Or it may further include a single molecule containing a terminal group capable of forming a polymer by heat. Single molecule containing a functional group crosslinkable by heat or light as described above; Alternatively, the molecular weight of a single molecule including a terminal group capable of forming a polymer by heat may be 2,000 g/mol or less.

In one embodiment of the present specification, the coating composition has a molecular weight of 2,000 g/mol or less, a single molecule including a functional group capable of crosslinking by heat or light; Or it further includes a single molecule containing a terminal group capable of forming a polymer by heat.

A single molecule containing a functional group crosslinkable by the heat or light; Or a single molecule containing a terminal group capable of forming a polymer by heat includes phenyl, biphenyl, fluorene, and naphthalene aryl; Arylamine; Or it may mean a single molecule in which fluorene is substituted with a functional group crosslinkable by heat or light or a terminal group capable of forming a polymer by heat.

The crosslinkable functional group is the same as described above.

In addition, in one embodiment of the present specification, the single molecule including the crosslinkable functional group has the following structures, but is not limited as long as it does not impair the properties of the coating composition of the present specification.

In another exemplary embodiment, a single molecule including a terminal group capable of forming a polymer by heat has the following structures, but is not limited as long as it does not impair the properties of the coating composition of the present specification.

In another exemplary embodiment, the viscosity of the coating composition is 2 cP to 15 cP.

When the viscosity is satisfied, it is easy to manufacture a cleaning agent.

The present specification also provides an organic light emitting device formed using the coating composition.

In one embodiment of the present specification, the cathode; Anode; And one or more organic material layers provided between the cathode and the anode, and at least one layer of the organic material layer includes a cured product of the coating composition, and the cured product of the coating composition is used for heat treatment or light treatment. It means that it is in a cured state.

In one embodiment of the present specification, the organic material layer containing the cured product of the coating composition is a hole transport layer, a hole injection layer, or a layer simultaneously performing hole transport and hole injection.

In another exemplary embodiment, the organic material layer formed using the coating composition is a light emitting layer.

In another exemplary embodiment, the organic material layer including the cured product of the coating composition is a light emitting layer, and the light emitting layer contains the compound of Formula 1 as a host of the light emitting layer.

In one embodiment of the present specification, the organic light emitting device is a hole injection layer, a hole transport layer. It further includes one or more layers selected from the group consisting of an electron transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer.

In another exemplary embodiment, the organic light emitting device may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In another exemplary embodiment, 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.

The organic material layer of the organic light emitting device of the present specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer as an organic material layer. However, the structure of the organic light emitting device is not limited to this, and may include fewer organic layers.

For example, the structure of the organic light emitting device according to the exemplary embodiment of the present specification is illustrated in FIG. 1.

1, an organic light emitting device in which an anode 201, a hole injection layer 301, a hole transport layer 401, a light emitting layer 501, an electron transport layer 601, and a cathode 701 are sequentially stacked on a substrate 101 The structure of is illustrated.

1 illustrates an organic light emitting device and is not limited thereto.

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 of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer is formed using a coating composition including the compound of Formula 1 above.

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating an anode, an organic material layer, and a cathode on a substrate. At this time, an anode is formed by depositing a metal or conductive metal oxide or alloys thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. And, after forming a hole injection layer, a hole transport layer, an organic material layer including a light emitting layer and an electron transport layer, and can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The present specification also provides a method for manufacturing an organic light emitting device formed using the coating composition.

Specifically, in one embodiment of the present specification, preparing a substrate; Forming a cathode or anode on the substrate; Forming one or more organic material layers on the cathode or anode; And forming an anode or a cathode on the organic material layer, and forming the organic material layer includes forming one or more organic material layers using the coating composition.

In one embodiment of the present specification, the organic material layer formed using the coating composition is formed using spin coating.

In another embodiment, the organic layer formed using the coating composition is formed by a printing method.

In the state 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 thereto.

Since the coating composition according to one embodiment of the present specification has a structural property, a solution process is suitable and can be formed by a printing method, and thus has an economical effect in time and cost when manufacturing the device.

In one embodiment of the present specification, the step of forming an organic material layer formed using the coating composition may include coating the coating composition on the cathode or anode; And heat-treating or photo-treating the coated coating composition.

In one embodiment of the present specification, the heat treatment temperature in the heat treatment step is 85°C to 250°C, and according to one embodiment, it may be 100°C to 250°C, and in another embodiment, 150°C To 200°C. When the range of the heat treatment temperature is satisfied, there is an advantage that packing can occur well at a temperature sufficient for crosslinking.

In another embodiment, the heat treatment time in the heat treatment step is 1 minute to 1 hour, and according to one embodiment, it may be 20 minutes to 1 hour. When the range of the heat treatment time is satisfied, there is an advantage in that it is possible to configure the device with stable multi-layer formation.

In one embodiment of the present specification, when the coating composition does not contain an additive, heat treatment is performed at a temperature of 100°C to 250°C, and crosslinking is preferably performed, and crosslinking is performed at a temperature of 120°C to 200°C. It is more preferable to be. In addition, the coating composition of the present specification may further include an initiator, but it is more preferably not used.

In the case of including the heat treatment or the light treatment step in the step of forming the organic material layer formed using the coating composition, a plurality of compounds of Formula 1 included in the coating composition forms a crosslink to provide an organic material layer containing a thinned structure. Can. In this case, when laminating another layer on the surface of the organic layer formed using the coating composition, it can be prevented from being dissolved by a solvent, morphologically affected or decomposed.

Therefore, when the organic layer formed by using the coating composition is formed by including a heat treatment or a photo-treatment step, resistance to a solvent is increased, and a solution deposition and crosslinking method can be repeatedly performed to form a multilayer, and stability is increased to increase the Life characteristics can be increased.

In one embodiment of the present specification, the coating composition comprising the compound of Formula 1 may use a coating composition mixed with a polymer binder and dispersed.

In one embodiment of the present specification, as the polymer binder, it is preferable that the charge transport is not extremely inhibited, and that the absorption of visible light is not strong is preferably used. Examples of the polymer binder include poly(N-vinylcarbazole), polyaniline and derivatives thereof, polythiophene and derivatives thereof, poly(p-phenylenevinylene) and derivatives thereof, poly(2,5-thienylenevinylene), and And derivatives thereof, polycarbonate, polyacrylate, polymethylacrylate, polymethylmethacrylate, polystyrene, polyvinyl chloride, polysiloxane, and the like.

In addition, the compound of Formula 1 according to an exemplary embodiment of the present specification may include the compound of Formula 1 alone in the organic material layer by including a carbazole and an amine group, and a coating composition comprising the compound of Formula 1 Thinning may be performed through heat treatment or light treatment, and may be included as a copolymer using a coating composition mixed with other monomers. In addition, by using a coating composition mixed with other polymers, it may be included as a copolymer, or may be included as a mixture.

As the anode material, a material having a large work function is preferably used to facilitate hole injection into the organic material layer. Specific examples of anode materials that can be used in the present invention include 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 SNO2: combination of metal and oxide such as Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the cathode material include metals such as barium, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There are multilayer structure materials such as LiF/Al or LiO2/Al, and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in the light emitting layer. A compound which prevents migration of the excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferable. It is preferable that the highest occupied molecular orbital (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 the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. As a hole transport material, the hole is transported from the anode or the hole injection layer and transported to the light emitting layer. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in the visible light region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

The light emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound. A compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons Suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited to these. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound 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)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

The hole blocking layer is a layer that prevents the cathode from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but are not limited thereto.

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

Hereinafter, examples will be described in detail to specifically describe the present specification. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more fully describe the present specification to those skilled in the art.

< Manufacturing example >

Manufacturing example 1. Preparation of Compound 1

(1) Preparation of intermediate 1-1

Intermediate 1-1

Decafluorobiphenyl (2.0 g, 6.06 mmol), 4-(phenylamino)phenol] (3.37 g, 18.17 mmol), potassium carbonate (2.5) in 100 ml RBF g, 18.17 mmol) in DMF 40 ml. The reaction was allowed to proceed by stirring at 120°C under a nitrogen atmosphere. After completion of the reaction, it is diluted with methyl-tert-butyl ether and washed with an aqueous sodium bicarbonate solution and brine. The organic layer was separated and dried over magnesium sulfate, and then the solvent was removed and purified by column chromatography to obtain intermediate 1-1.

(2) Preparation of Intermediate 1-2

Intermediate 1-2

Intermediate 1-1 under nitrogen atmosphere in 50 ml RBF (1.3g, 1.96mmol), 9-(4-(1,3-dioxolan-2-yl)phenyl)-3-bromo-9H-carbazole[9-(4-(1,3-dioxolan- 2-yl)phenyl)-3-bromo-9H-carbazole] (1.7g, 4.3mmol), Pd[P(t-Bu) ₃ ] ₂ (50mg, 0.10mmol), NaOt-Bu (470mg, 4.89mmol) Is dissolved in 10 ml of toluene. The reaction is allowed to proceed by heating and stirring at 90°C. Then, when the reaction is complete, work up with H ₂ O and EA, separate the organic layer, dry it, and filter. The solvent is then removed by rotary evaporation. The obtained material was purified by column chromatography to obtain solid intermediate 1-2.

(3) Preparation of Intermediate 1-3

Intermediate 1-3

Dissolve intermediate 1-2 (2.0 g, 1.55 mmol) in 50 ml RBF in 10 ml THF. 1N HCl (5.0ml. 4.64mmol) was added slowly and stirred. NaHCO ₃ after the reaction is completed The reaction was terminated by adding an aqueous solution and stirring. Subsequently, the organic layer was separated and the solvent was removed, and then TEA was added to deactivation to load on silica gel, which was then purified through column chromatography. After purification solid intermediate 1-3 is obtained.

(4) Preparation of compound 1

Compound 1

CH ₃ PPh ₃ Br (1.1 g, 3.08 mmol) and t-BuOK (409 mg, 3.64 mmol) vacuum dried at 250° C. in 250 mL RBF at room temperature and nitrogen atmosphere, dissolved in 10 ml THF and stirred for 1 hour. To generate ylide. Intermediate 1-3 was slowly added to proceed with an olefination reaction. After confirming that the reaction is over, terminating with water, work-up with EA and brine, remove the residue with Na ₂ SO ₄ and remove the solvent. It was loaded as a solid on silica gel, which was deactivated by adding TEA, and purified through column chromatography. After removal of the solvent, a white solid compound 1 was obtained. 2 is a diagram showing an MS spectrum of Compound 1, and NMR data values of Compound 1 are shown below.

1H NMR (500 MHz): δ = 8.03-8.01 (d, 2H), 7.93 (s, 2H), 7.69-7.68 (d, 2H), 7.57-7.56 (d, 2H), 7.43-7.39 (m, 6H ), 7.26-7.23 (m, 6H), 7.14-7.08 (m, 8H), 7.00-6.95 (m, 6H), 6.90-6.84 (m, 2H), 5.91-5.87 (d, 2H), 5.39-5.37 (d, 2H)

Manufacturing example 2. Preparation of compound 2

(1) Preparation of compound 2

Compound 2

Intermediate 1-1 (2.0 g, 3.01 mmol), 3-bromo-9-phenyl-6-(4-vinylphenyl)-9H-carbazole [3-bromo-9-phenyl-6] in nitrogen atmosphere in 50 ml RBF -(4-vinylphenyl)-9H-carbazole] (2.5g, 6.32mmol), Pd[P(t-Bu) ₃ ] ₂ (75mg, 0.15mmol), NaOt-Bu (865mg, 9.0mmol) toluene ) Dissolve in 15 ml. The reaction is allowed to proceed by heating and stirring at 90°C. Then, when the reaction is complete, work up with H ₂ O and EA, separate the organic layer, dry it, and filter. The solvent is then removed by rotary evaporation. The obtained material was purified by column chromatography to obtain solid compound 2. The NMR data values of Compound 2 are shown below.

1H NMR (500 MHz): δ = 8.32-8.30 (d, 2H), 8.16-7.13 (d, 2H), 7.90 (s, 2H),7.62-7.50 (m, 20H),7.36-7.33 (m, 4H ), 7.25-7.23 (m, 4H), 7.16-7.05 (m, 10H), 6.87-6.85 (d, 4H), 6.74-6.71 (m, 2H), 5.76-5.74 (d, 2H), 5.26-5.24 (d, 2H)

Manufacturing example 3. Preparation of compound 83

(1) Preparation of compound 83

Compound 83

Intermediate 1-1 (2.0 g, 3.01 mmol), 3-(4-crophenyl)-9-(4-vinylphenyl)-9H-carbazole [3-(4-chlorophenyl)- under nitrogen atmosphere in 50 ml RBF- 9-(4-vinylphenyl)-9H-carbazole] (2.4g, 6.32mmol), Pd[P(t-Bu) ₃ ] ₂ (75mg, 0.15mmol), NaOt-Bu (865mg, 9.0mmol) with toluene ( Toluene) dissolved in 15 ml. The reaction is allowed to proceed by heating and stirring at 90°C. Then, when the reaction is complete, work up with H ₂ O and EA, separate the organic layer, dry it, and filter. The solvent is then removed by rotary evaporation. The obtained material was purified by column chromatography to obtain solid compound 83. The NMR data values of Compound 83 are shown below.

1H NMR (500 MHz): δ = 8.55-8.53 (d, 2H), 8.00-7.94 (m, 6H), 7.79-7.77 (d, 2H), 7.70-7.68 (d, 4H), 7.56-7.50 (m , 8H), 7.39-7.36 (m, 6H), 7.24-7.18 (m, 16H), 7.95-6.87 (m, 4H), 6.88-6.82 (m, 2H), 5.79-5.76 (d, 2H), 5.32 -5.29 (d, 2H)

Manufacturing example 4. Preparation of compound 165

(1) Preparation of intermediate 165-1

Intermediate 165-1

Perfluorobenzene (3.0g, 16.1mmol), 4-(phenylamino)phenol (5.9g, 32.5mmol), potassium carbonate (5.5g) in 100ml RBF , 40.01mmol) in 40 ml of DMF. The reaction proceeds by stirring at 120 ^° C under a nitrogen atmosphere. After completion of the reaction, dilute with methyl-tert-butyl ether, and then wash with aqueous sodium bicarbonate solution and brine. The organic layer was separated and dried over magnesium sulfate, and then the solvent was removed and purified by column chromatography to obtain intermediate 165-1.

(1) Preparation of compound 165

Compound 165

Intermediate 1 (1.0g, 1.51mmol), 3-bromo-9-(4-vinylphenyl)-9H-carbazole (1.4g, 4.0mmol), Pd[P(t-Bu) ₃ ] ₂ under nitrogen atmosphere in 50ml RBF (50mg, 0.10mmol) and NaOt-Bu (433mg, 4.5mmol) are dissolved in 8ml of toluene. The reaction was allowed to proceed by heating and stirring at 90 ^° C. Then, when the reaction is complete, work up with H ₂ O and EA, separate the organic layer, dry it, and filter. The solvent is then removed by rotary evaporation. The obtained material was purified by column chromatography to obtain solid compound 165. The NMR data values of Compound 165 are shown below.

1H NMR (500 MHz): δ = 8.64-8.61 (d, 2H), 8.12-8.01 (m, 6H), 7.82-7.80 (d, 2H), 7.75-7.73 (d, 4H), 7.66-7.58 (m , 8H), 7.42-7.39 (m, 6H), 7.28-7.23 (m, 16H), 7.95-7.90 (m, 4H), 6.90-6.88 (m, 2H), 5.80-5.78 (d, 2H), 5.40 -5.37 (d, 2H)

< Example >

Example One.

A glass substrate on which ITO (indium tin oxide) was thinned to a thickness of 1500 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol and acetone for 30 minutes each, and after drying, the substrate was transferred to a glove box.

Spin coating the coating composition of the following compound 1 (20 mg), formula C (1 mg) and toluene (1 mg) on the ITO transparent electrode thus prepared to form a hole injection layer of 300 mm thick and coated for 1 hour in a hot plate in air. The composition was cured. Subsequently, after transferring to a vacuum evaporator, the following a-NPD was vacuum deposited on the hole injection layer to form a hole transport layer.

After depositing a-NPD to a thickness of 40 nm, Alq3 below was vacuum-deposited to 50 nm on the hole transport layer to form a light emitting layer. A cathode was formed by depositing aluminum with a thickness of 0.5 nm and aluminum with a thickness of 100 nm on the electron transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, the LiF of the cathode was maintained at 0.3 Å/sec, and the deposition rate of 2 Å/sec for aluminum, and the vacuum degree during deposition was 2x10 ^-7 to 3x10. ^-5 torr was maintained.

Example 2.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2 instead of Compound 1 was used as the material for the hole injection layer, and Chemical Formula D was used instead of Chemical Formula C.

< Comparative example >

Comparative example One.

An organic light emitting device was manufactured in the same manner as in Example 1, except that the following compound HIL-1 was used instead of Compound 1 as the material for the hole injection layer, and Formula D was used instead of Formula C.

<Compound HIL-1>

For the organic light emitting device manufactured in Comparative Example 1, Example 1 and Example 2, the driving voltage, current efficiency and life were measured, and the results are shown in Table 1 below. It means the time it takes to decrease to.

3 is a diagram showing the current density-driving voltage value of the organic organic light-emitting device prepared in Comparative Example 1, Example 1 and Example 2, Figure 4 is in Comparative Example 1, Example 1 and Example 2 It is a diagram showing the luminance-time value of the manufactured organic organic light-emitting device. The black graph represents Comparative Example 1, the red graph represents Example 1, and the blue graph represents Example 2.

Sample Driving voltage (V) Life (T90@20mA/ cm ² ) Comparative Example 1 4.07 8 Example 1 3.67 25.4 Example 2 3.72 29.7

As shown in Table 1, it can be seen that Examples 1 and 2 using the compound of Formula 1 herein exhibit superior characteristics in terms of driving voltage and life of the organic light emitting device than Comparative Example 1.

101: substrate
201: anode
301: hole injection layer
401: hole transport layer
501: light emitting layer
601: electron transport layer
701: cathode

Claims (13)

Compound represented by the formula (1):
[Formula 1]

In Chemical Formula 1,
Ar ₁ to Ar ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heterocyclic group, or may combine with an adjacent substituent to form an aromatic hydrocarbon ring,
s1 and s2 are each an integer of 0 to 6, and when s1 and s2 are each 2 or more, the substituents in parentheses are the same or different from each other,
s3 and s4 are each an integer from 0 to 4, and when s3 and s4 are 2 or more, the substituents in parentheses are the same or different from each other,
L is a substituted or unsubstituted arylene group containing fluorine (F),
n is 1 or 2,
When n is 2, L is the same as or different from each other,
L ₁ and L ₄ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
L ₇ and L ₈ are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
L ₂ and L ₃ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted alkenylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
L ₅ and L ₆ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted alkenylene group; Or a substituted or unsubstituted arylene group,
Y ₁ to Y ₆ are the same as or different from each other, and each independently hydrogen; Or a functional group capable of crosslinking by heat or light, and at least one of Y ₁ to Y ₆ is a functional group crosslinkable by heat or light. The compound according to claim 1, wherein the functional group capable of crosslinking by heat or light in the definition of Y ₁ to Y ₆ is any one of the following structures:

In the above structure,
R is hydrogen; Or a substituted or unsubstituted alkyl group,
A ₁ to A ₃ are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. delete The method according to claim 1, wherein L is a compound represented by the formula (2):
[Formula 2]

In Chemical Formula 2,
R ₁ to R ₄ are the same as or different from each other, and each independently hydrogen; Or fluorine (F), and at least one of R ₁ to R ₄ is fluorine (F),
m is 1 or 2, and when m is 2, the substituents in parentheses are the same or different from each other. The compound according to claim 1, wherein the compound represented by Formula 1 is any one selected from Compounds 1 to 328 below:

. A coating composition comprising a compound according to any one of claims 1, 2, 4 and 5. The coating composition of claim 6, wherein the coating composition further comprises a p-doped material. The coating composition of claim 6, wherein the coating composition has a viscosity of 2 cP to 15 cP. Cathode;
Anode; And
It includes at least one layer of an organic material provided between the cathode and the anode,
At least one layer of the organic layer includes the cured product of the coating composition of claim 6,
The cured product of the coating composition is an organic light emitting device in which the coating composition is cured by heat treatment or light treatment. The organic light emitting device of claim 9, wherein the organic material layer containing the cured product of the coating composition is a hole transport layer, a hole injection layer, or a layer simultaneously performing hole transport and hole injection. Preparing a substrate;
Forming a cathode or anode on the substrate;
Forming one or more organic material layers on the cathode or anode; And
Forming an anode or a cathode on the organic material layer,
The step of forming the organic material layer includes forming one or more organic material layers using the coating composition of claim 6. The method of claim 11, wherein the organic material layer formed using the coating composition is formed using spin coating. The method according to claim 11, Forming an organic layer formed using the coating composition is
Coating the coating composition on the cathode or anode; And
A method of manufacturing an organic light emitting device comprising the step of heat-treating or photo-treating the coated coating composition.

Images