KR101889603B1 - Coating composition comprising a derivative imoniun and organic light emitting device using the same - Google Patents

Abstract

The present disclosure provides coating compositions comprising imonium derivatives, organic light emitting devices formed using the coating compositions, and methods of making the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a coating composition containing an oxonium derivative and an organic light emitting device using the coating composition. [0002]

The present disclosure relates to a coating composition comprising an imonium derivative, an organic light emitting device formed using the coating composition, and a method of manufacturing the same.

The organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of organic luminescence phenomenon is as follows. When an organic layer is positioned between the anode and the cathode, electrons and holes are injected into the organic layer from the cathode and the anode, respectively, when an electric current is applied between the two electrodes. Electrons and holes injected into the organic layer are recombined to form an exciton, and the exciton falls back to the ground state to emit light. An organic light emitting device using such a principle may be generally composed of an organic material layer including a cathode, an anode and an organic material layer disposed therebetween, for example, a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer.

As a material used in an organic light emitting device, a pure organic material or a complex in which an organic material and a metal form a complex is mostly used. Depending on the application, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, . As the hole injecting material and the hole transporting material, an organic material having a p-type property, that is, an organic material that is easily oxidized and electrochemically stable at the time of oxidation is mainly used. On the other hand, as an electron injecting material or an electron transporting material, an organic material having an n-type property, that is, an organic material that is easily reduced and electrochemically stable when being reduced is mainly used. As the light emitting layer material, a material having both a p-type property and an n-type property, that is, a material having both a stable form in oxidation and in a reduced state is preferable, and a material having a high luminous efficiency for converting an exciton into light desirable.

In addition to the above, it is preferable that the material used in the organic light emitting device further has the following properties.

First, the material used in the organic light emitting device is preferably excellent in thermal stability. This is because joule heating occurs due to the movement of charges in the organic light emitting device. NPB, which is mainly used as a hole transport layer material, has a glass transition temperature of 100 ° C or less, which is a problem that is difficult to use in an organic light emitting device requiring a high current.

Secondly, in order to obtain a highly efficient organic light emitting device capable of driving at a low voltage, holes or electrons injected into the organic light emitting element should be smoothly transferred to the light emitting layer, and injected holes and electrons should not escape from the light emitting layer. For this purpose, the material used in the organic light emitting device should have an appropriate band gap and a HOMO or LUMO energy level. In the case of PEDOT: PSS used as a hole transport material in the organic light emitting device manufactured by the solution coating method, since the LUMO energy level is lower than the LUMO energy level of the organic material used as the light emitting layer material, There is a difficulty in.

In addition, materials used in organic light emitting devices should have excellent chemical stability, charge mobility, and interface characteristics with electrodes or adjacent layers. That is, the material used in the organic light emitting device should have little deformation of the material due to moisture or oxygen. In addition, by having appropriate hole or electron mobility, it is necessary to maximize the formation of excitons by balancing the density of holes and electrons in the light emitting layer of the organic light emitting device. And, for the stability of the device, the interface with the electrode including the metal or the metal oxide should be good.

In recent years, organic light emitting devices have been developed by using a solution process, particularly an inkjet process, in place of the existing deposition process. This can drastically reduce the cost of the organic light emitting device process. In the early days, it was attempted to develop organic light emitting devices by coating all the organic light emitting device layers by a solution process. However, since there are limitations in the current technology, only HIL, HTL, and EML are processed in a solution process, Is being studied. In the early days, organic luminescent materials having a polymer shape were used to increase the coating property. However, due to the batch-batch problem and purity problem inherent in polymers, many monolayer OLED materials are under development.

The charge transporting material used as the hole injecting layer has semiconductor characteristics but does not have sufficient number of charge and charge mobility for generating and transporting electric charge and thus an arbitrary amount of electron accepting compound is added so that the number of charges and the charge mobility And the performance and lifetime of the organic light emitting device can be improved. Examples of such electron-accepting compounds include TCNQ, F ₄ TCNQ, tris (4-bromophenylaminium hexachloroantimonate) and TBPAH. The difference in structure can interfere with intermolecular stacking or charge transport.

Korean Patent Publication No. 2012-0112277

It is an object of the present invention to provide a coating composition comprising an imonium derivative, an organic light emitting element formed using the coating composition, and a method of manufacturing the same.

An embodiment of the present invention provides a coating composition for an organic light emitting device comprising an imonium derivative represented by the following Formula 1:

[Chemical Formula 1]

In formula (1)

R 1 to R 4 are the same or different and each independently represents a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle,

L is a substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In addition, one embodiment of the present disclosure includes a cathode; Anode; And one or more organic layers disposed between the cathode and the anode, wherein at least one of the organic layers includes the above-described coating composition.

In addition, one embodiment of the present disclosure provides a method of manufacturing a semiconductor device, comprising: preparing a substrate; Forming a cathode or an anode on the substrate; Forming at least one organic material layer on the cathode or the anode; And forming an anode or a cathode on the organic material layer, wherein at least one of the organic material layers is formed using the coating composition described above.

The coating composition according to one embodiment of the present disclosure can be used as an organic layer material of an organic light emitting device and can provide a low driving voltage, a high luminous efficiency and a high lifetime characteristic.

1 shows an example of an organic light emitting device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

Hereinafter, the present specification will be described in detail.

When a member is referred to herein as being "on" another member,

Not only when a member is in contact with another member but also when another member is present between the two members.

Whenever a component is referred to as "comprising ", it is to be understood that the component may include other components as well, without departing from the scope of the present invention.

One embodiment of the present invention provides a coating composition for an organic light emitting device comprising the imonium derivative represented by the above formula (1). In the case of the coating composition for an organic electroluminescent device comprising the imonium derivative represented by the above formula (1), it is easy to manufacture due to its excellent solubility, and a uniform coating layer can be formed using the coating composition. In addition, when mixed with a charge transporting material used as a hole injecting layer, the hole transporting ability is improved due to the presence of an imonium derivative, the driving voltage is lowered, high luminous efficiency is exhibited, and high lifetime characteristics are provided.

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

는 다른 치환기에 연결되는 부위를 의미한다.In the present specification,

Quot; refers to a moiety that is connected to another substituent.

In the present specification, the term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, When substituted, two or more substituents may be the same or different from each other.

As used herein, the term "substituted or unsubstituted" heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; An alkyl group; An alkoxy group; An alkenyl group; An aryl group; An amine group; An arylamine group, and a heterocyclic group, or a substituted or unsubstituted aryl group to which at least two of the substituents exemplified above are connected. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

Substituents comprising the alkyl groups, alkoxy groups and other alkyl moieties described herein include both straight chain and branched forms.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to 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,

,

, A spirofluorenyl group

(9,9-dimethylfluorenyl group), and

(9,9-diphenylfluorenyl group), and the like. However, the present invention is not limited thereto.

The aryl group may be substituted with an alkyl group to act as an arylalkyl group. The alkyl group may be selected from the examples described above.

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, P, S, Si and Se, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is from 1 to 30. [ Examples of the heterocyclic group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, A thiadiazole group, a thiadiazole group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a pyrazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, A phenanthridinyl group, a diazanaphthalenyl group, a triazinylidene group, an indole group, a thiazolidinyl group, a thiomorpholinyl group, a thiomorpholinyl group, a thiomorpholinyl group, an isothiazolyl group, , Indolinyl group, indolizinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group , Benzofuranyl group, dibenzothiophenyl group and dibenzofura < RTI ID = 0.0 > But are not limited to these.

The heterocyclic group may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring.

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

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. The amine group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine A phenyl group, a phenyl group, a phenyl group, a phenyl group, a naphthyl group, a naphthyl group, a naphthyl group, a biphenyl group, an anthracenyl group, a 9-methyl- anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, , Triphenylamine group and the like, but are not limited thereto.

In the present specification, an arylamine group means an amine group substituted with an aryl group, and the above-mentioned examples can be applied to an aryl group.

In the present specification, the description of the above-mentioned cycloalkyl group can be applied, except that the cycloalkylene is a divalent group.

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

In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group.

As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the ring formed by bonding adjacent groups to each other may be monocyclic or polycyclic, and may be an aliphatic, aromatic, or aliphatic and aromatic condensed ring, and may form a hydrocarbon ring or a heterocyclic ring.

The hydrocarbon ring may be selected from the examples of the cycloalkyl group or the aryl group except that the hydrocarbon ring is not the monovalent group. The heterocyclic ring may be an aliphatic, aromatic, or aliphatic and aromatic condensed ring, and examples thereof may be selected from the heterocyclic groups except that the heterocyclic group is not a monovalent group.

According to another embodiment, L is a cycloalkylene group having 1 to 20 carbon atoms, phenylene, biphenylene or naphthylene.

According to another embodiment, R1 to R4 are the same or different and are each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to another embodiment, R1 to R4 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to another embodiment, R1 to R4 are the same or different and each independently represents an aryl group substituted or unsubstituted with an amine group; Or a heterocyclic group substituted or unsubstituted with an aryl group.

According to another embodiment, R1 to R4 are the same or different and each independently represent an aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with an amine group; Or a heterocyclic group having 1 to 40 carbon atoms which is unsubstituted or substituted with an aryl group.

In one embodiment of the present disclosure, the coating composition comprises a monovalent anion. In one embodiment of the present invention, the monovalent anion is represented by any one of the following formulas (2-1) to (2-6).

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Chemical Formula 2-5]

[Chemical Formula 2-6]

In the formulas (2-1) to (2-6), A1 is a divalent element, A2 is a trivalent element, A3 is a tetravalent element, A4 is a trivalent element and A55 is an element of the valence, B1 to B6 are the same or different from each other , Each independently a divalent linking group, R 5 to R 20 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted aryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring.

According to another embodiment, A1 is oxygen (O), A2 is nitrogen (N), A3 is carbon (C), A4 is boron (B) or gallium (Ga) Sb).

According to one embodiment, is the B1 to B6 is SO _2.

According to an embodiment of the the B1 to B6 is CF _2.

According to another embodiment, R5 to R20 are the same or different and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to another embodiment, R5 to R20 are the same or different and each independently represents an alkyl group substituted or unsubstituted with a fluorine group; Or an aryl group which is substituted or unsubstituted with a fluorine group. According to another embodiment, R5 to R20 are the same or different and are each independently a pentafluorophenyl group.

In one embodiment of the present disclosure, the coating composition comprises a compound represented by any one of the following structural formulas.

In one embodiment of the present disclosure, the coating composition comprises a charge transport material represented by the following formula (3).

(3)

In formula (3)

X1 and X2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group,

a and b are each an integer of 1 to 6,

When a and b are each 2 or more, the structures in parentheses are the same or different from each other,

A and B are the same or different from each other, and each independently hydrogen; Or deuterium,

Ar 1 and Ar 2 are the same or different and are each independently a substituted or unsubstituted aryl group,

n is an integer of 1 to 4,

When n is an integer of 2 or more, L2 of 2 or more are the same or different,

L1 is a substituted or unsubstituted arylene group,

L2 and L3 are the same or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

Y1 and Y2 are the same or different from each other and each independently is a functional group capable of crosslinking by heat or light.

In one embodiment of the present specification, X1 and X2 are the same or different and each independently a substituted or unsubstituted aryl group.

In one embodiment of the present invention, X1 and X2 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment, X1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, X1 is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, X1 is a phenyl group.

In one embodiment, X2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, X2 is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, X2 is a phenyl group.

In one embodiment of the present disclosure, A is hydrogen.

In another embodiment, B is hydrogen.

In one embodiment of the present disclosure, n is one.

In another embodiment, n is two.

In one embodiment of the present specification, L1 is a substituted or unsubstituted arylene group.

In another embodiment, L < 1 > is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In another embodiment, it is a substituted or unsubstituted biphenylene group.

In another embodiment, L < 1 > is a biphenylene group.

In one embodiment of the present specification, L2 and L3 are the same or different from each other, and each independently is a direct bond; Or a substituted or unsubstituted arylene group.

In one embodiment of the present specification, L2 and L3 are the same or different from each other, and each independently is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L2 and L3 are the same or different from each other, and each independently is a direct bond; Or a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, L2 is a direct bond.

In another embodiment, L2 is a substituted or unsubstituted phenylene group.

In another embodiment, L2 is a phenylene group.

In one embodiment of the present specification, L3 is a direct bond.

In another embodiment, L3 is a substituted or unsubstituted phenylene group.

In another embodiment, L3 is a phenylene group.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different and each independently a substituted or unsubstituted aryl group.

In another embodiment, Ar 1 and Ar 2 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different and are each independently a substituted or unsubstituted phenyl group.

As used herein, the term "crosslinkable functional group" may mean a reactive substituent which undergoes crosslinking between the compounds by exposure to heat and / or light. The crosslinking can be generated by heating or irradiating light to form a carbon-carbon multiple bond, linking radicals formed by decomposition of the cyclic structure.

이고, 상기 가교 가능한 작용기가 열처리 또는 광처리에 의하여 가교되는

의 구조로 다른 카바졸 유도체와 연결될 수 있다.For example, when the crosslinkable functional group is

, And the crosslinkable functional group is crosslinked by heat treatment or light treatment

Lt; RTI ID = 0.0 > carbazole < / RTI > derivatives.

In one embodiment of the present invention, Y1 and Y2 are each the same or different and are each independently represented by any one of the following formulas (3-1) to (3-7).

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Chemical Formula 3-4]

[Formula 3-5]

[Chemical Formula 3-6]

[Chemical Formula 3-7]

In formulas (3-1) to (3-7)

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

In another embodiment, Q is selected from the group consisting of hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In another embodiment, Q is selected from the group consisting of hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In another embodiment, the charge transporting material may be represented by any one of the following formulas (4-1) to (4-3).

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

In one embodiment of the present disclosure, the coating composition may further comprise an electron acceptor.

In another embodiment, the charge acceptor may be represented by any one of the following formulas (5-1) to (5-5).

[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

[Formula 5-4]

[Formula 5-5]

In one embodiment of the present disclosure, the coating composition comprises the imonium derivative, an anion and a solvent.

In one embodiment of the present disclosure, the coating composition may be in a liquid phase. The "liquid phase" means that the liquid phase is at normal temperature and pressure.

In one embodiment of the present invention, the solvent includes, for example, chlorinated solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; Ether solvents such as tetrahydrofuran and dioxane; 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 solvents such as acetone, methyl ethyl ketone, and cyclohexanone; Ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate; Examples of polyhydric alcohols 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, Alcohols and their derivatives; Alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; A sulfoxide-based solvent such as dimethylsulfoxide, an amide-based solvent such as N-methyl-2-pyrrolidone or N, N-dimethylformamide; Benzoate-based solvents such as butyl benzoate and methyl-2-methoxybenzoate; Tetralin; 3-phenoxy-toluene, and the like. However, it is sufficient for a solvent capable of dissolving or dispersing the emonium derivative according to one embodiment of the present invention, and the solvent is not limited thereto.

In another embodiment, the solvents may be used alone or in combination of two or more solvents.

One embodiment of the present disclosure includes a cathode; Anode; And one or more organic layers disposed between the cathode and the anode, wherein at least one of the organic layers includes the above-described coating composition.

In one embodiment of the present invention, the organic material layer including the coating composition is a hole transporting layer, a hole injecting layer, or a layer simultaneously transporting holes and injecting holes.

In one embodiment of the present invention, the organic light emitting element is a hole injection layer, a hole transport layer, An electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

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

 In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic layer, and an anode are sequentially stacked on a substrate.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer 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 injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

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

1 shows an organic light emitting device in which an anode 201, a hole injecting layer 301, a hole transporting layer 401, a light emitting layer 501, an electron transporting layer 601 and a cathode 701 are sequentially stacked on a substrate 101 Are illustrated.

1, the hole injection layer 301 is formed using a coating composition containing an emonium derivative.

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

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

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer is formed using the coating composition containing the imonium derivative.

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating an anode, an organic layer, and a cathode on a substrate. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate by a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and then depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

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

Specifically, in one embodiment of the present disclosure, there is provided a method comprising: preparing a substrate; Forming a cathode or an anode on the substrate; Forming at least one organic material layer on the cathode or the anode; And forming an anode or a cathode on the organic material layer, wherein at least one of the organic material layers is formed using the coating composition.

In one embodiment of the present invention, the organic 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 inkjet printing.

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, but is not limited to, nozzle printing, offset printing, transfer printing, or screen printing.

Since the coating composition according to one embodiment of the present invention has a structural characteristic and is suitable for a solution process, the coating composition can be formed by a printing method, so that there is an economical effect in time and cost in manufacturing a device.

In one embodiment of the present disclosure, the step of forming an organic layer formed using the coating composition comprises: coating the coating composition on the cathode or the anode; And heat treating or light treating the coated coating composition.

In the case of including the heat treatment or light treatment step in the step of forming the organic material layer formed using the coating composition, it is possible to provide an organic material layer including a structure in which a plurality of charge carriers contained in the coating composition form a bridge to form a thin film. In this case, the organic layer formed using the coating composition can be prevented from being dissolved, morphologically affected or decomposed by the solvent applied on the surface.

Therefore, when the organic material layer formed using the coating composition is formed by including the heat treatment or the light treatment step, the resistance to the solvent is increased, so that the multilayer can be formed by repeating the solution deposition and crosslinking method, Life characteristics can be increased.

In one embodiment of the present disclosure, the coating composition may comprise a monomolecular charge carrier comprising a carbazole.

In one embodiment of the present specification, the coating composition may be a coating composition in which a polymer binder is mixed and dispersed.

In one embodiment of the present invention, the polymer binder is preferably one that does not extremely inhibit charge transport, and that does not strongly absorb visible light. Examples of the polymeric binder include poly (N-vinylcarbazole), polyaniline and derivatives thereof, polythiophene and derivatives thereof, poly (p-phenylenevinylene) and derivatives thereof, poly (2,5-thienylenevinylene) A derivative thereof, a polycarbonate, a polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane and the like.

In addition, the coating composition according to one embodiment of the present invention may include the coating composition alone in the organic material layer, or the coating composition containing the imonium derivative may be thinned through heat treatment or light treatment, Can be incorporated as a copolymer using one coating composition. Also, copolymers, or mixtures thereof, may be included using coating compositions mixed with other polymers.

As the anode material, a material having a large work function is preferably used so that injection of holes into the organic material layer is smooth. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

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 magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole injecting material is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, a hole injecting effect for the anode, an excellent hole injecting effect for a light emitting layer or a light emitting material, A compound which prevents the exciton from migrating to the electron injection layer or the electron injection material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer and transports holes from the anode or the hole injection layer to the light emitting layer as the hole transport material. 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 together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected 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. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron transporting material is a layer that transports electrons from the electron injecting layer to the electron transporting layer and transports electrons from the electron injecting layer to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode to the light emitting layer. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material with a low work function followed by an aluminum layer or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from an electrode and has an ability to transport electrons and has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The hole blocking layer is a layer which prevents the cathode from reaching the hole, and can be generally formed under the same conditions as the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

The organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.

In one embodiment of the present invention, the coating composition may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

Manufacturing example  1. Preparation of Formula 1-1

(N1, N1, N ', N4'-tetraphenylbenzene-1,4-diamine, 5 g, 12.1 mmol) and lithium bis (trifluoro (Methylene chloride, 25 g) and ethanol (10 g) were charged and refluxed for 3 hours. Then, sodium persulfate (0.2 g, sodium persulfate, 2 g) and water (30 g) were added and refluxed for 2 hours. To the mixture was further added methylene chloride (40 g) and water (50 g), and the layered methylene chloride layer was vacuum distilled to obtain an imonium compound N, N, N ', N'-tetraphenylbenzene (N1, N1, N ', N4'-tetraphenylbenzene-1,4-diimonium bis (trifluoromethane) sulfonamide) was obtained.

Manufacturing example  2. Preparation of Formulas 1-2

Lithium bis (trifluoromethane) sulfonamide (7.66 g, 26.6 mmol) was added to a solution of potassium tris (trifluoromethanesulfonyl) methide (11.96 g, 2.9 g of the compound of the formula 1-2 was synthesized in the same manner as in the synthesis of the compound of the formula 1-1.

Manufacturing example  3. Preparation of Formulas 1-3

Lithium bis (trifluoromethane) sulfonamide (7.66 g, 26.6 mmol) was added to a solution of silver tetrakis (pentafluorophenyl) borate (20.87 g, 1.4 g of the compound of the formula 1-3 was synthesized in the same manner as in the synthesis of the compound of the formula 1-1.

Manufacturing example  4. Preparation of Formulas 1-4

N, N ', N'-tetraphenyl- [1,1'-biphenyl] -4,4-diamine (N, Bis (trifluoromethane) sulfonamide (6.43 g, 22.5 mmol), methylene chloride (25 g), and the like) And ethanol (10 g) were added. After refluxing for 3 hours, sodium persulfate (2 g) and water (30 g) were added, and the mixture was refluxed for 2 hours. To the mixture was further added methylene chloride (40 g) and water (50 g), and the layered methylene chloride layer was vacuum distilled to obtain an iminium compound N, N, N ', N'-tetraphenyl- [1,1'-biphenyl] -4,4-diimonium bis (trifluoromethane) sulfonimide (N, N ', N'- tetraphenyl- [1,1'-biphenyl] -4 , 4'-diimonium bis (trifluoromethane) sulfonamide).

Manufacturing example  5. Preparation of Formulas 1-5

Lithium bis (trifluoromethane) sulfonamide (6.43 g, 22.5 mmol) was added to a solution of potassium tris (trifluoromethanesulfonyl) methide (10.12 g, 1.4 g of the compound of the formula 1-5 was synthesized in the same manner as in the synthesis of the compound of the formula 1-4.

Manufacturing example  6. Preparation of 1-6

Lithium bis (trifluoromethane) sulfonamide (6.43 g, 22.5 mmol) was added to a solution of silver tetrakis (pentafluorophenyl) borate (17.7 g, 3.5 g of the compound of the formula 1-6 was synthesized in the same manner as in the synthesis of the compound of the formula 1-4.

Manufacturing example  7. Preparation of 1-7

N'-diphenyl-N, N'-bis (9-phenyl-9H- carbazole-3-yl) - [1,1'-biphenyl] -4,4'-diamine, 6.48 g, 7.92 mmol) and lithium bis (trifluoromethane) sulfonamide , 5g, 17.4mmol), methylene chloride (25g) and ethanol (10g) were added and refluxed for 3 hours. Then sodium persulfate (2g) and water (30g) Lt; / RTI > To the mixture was further added methylene chloride (40 g) and water (50 g), and the layered methylene chloride layer was vacuum distilled to obtain an iminium compound N, N, N ', N'-tetraphenyl- [1,1'-biphenyl] -4,4-diimonium (N, N'-diphenyl-N, N'- -biphenyl] -4,4'-diaminonium bis (trifluoromethane) sulfonamide.

The following preparations were synthesized similarly to the above method.

Experimental Example  One

The coating composition can be prepared by mixing the compound represented by Formula 1 of the present invention, The charge carriers represented by the following Chemical Formulas 4-1 to 4-3 described in Application No. KR10-2015-0169384 or KR10-2016-0049481 were mixed in an organic solvent (cyclohexanone) at 5 wt%.

As the charge transporting material, the following arylamine-based derivatives of the following formulas (4-1) to (4-3) are used, but the present invention is not limited thereto

[Formula 4-1]

[화학식 4-2]

[Formula 4-2]

[Formula 4-3]

Coating composition Charge carrier Imonium derivative Charge transporter: Emonium derivative ratio One - Formula 1-15 0: 1 2 4-1 Formula 1-15 0.8: 0.2 3 4-2 Formula 1-15 0.7: 0.3 4 4-3 Formula 1-15 0.8: 0.2 5 4-2 1-7 0.8: 0.2 6 4-1 1-8 0.7: 0.3 7 4-3 1-7 0.8: 0.2 8 4-3 (1-1) 0.8: 0.2 9 4-3 1-2 0.8: 0.2 10 4-3 1-3 0.8: 0.2 11 4-3 Formula 1-4 0.8: 0.2 12 4-3 1-5 0.8: 0.2 13 4-3 1-6 0.8: 0.2 14 4-3 1-8 0.8: 0.2 15 4-3 1-9 0.8: 0.2 16 4-3 1-10 0.8: 0.2 17 4-3 (1-11) 0.8: 0.2 18 4-3 (1-12) 0.8: 0.2 19 4-3 Formula 1-13 0.8: 0.2 20 4-3 (1-14) 0.8: 0.2 21 4-1 - 1: 0 22 4-2 - 1: 0 23 4-3 - 1: 0

Example  One

The glass substrate on which ITO (indium tin oxide) was deposited to a thickness of 1500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic cleaning was performed with a solvent of isopropyl alcohol and acetone for 30 minutes each, and the substrate was transported to a glove box.

On this ITO transparent electrode, the coating composition 1 shown in the following table was spin-coated to form a hole injection layer having a thickness of 300 Å, and the coating composition was cured on a hot plate for 30 minutes under an N ₂ atmosphere. Thereafter, the resultant was transferred to a vacuum evaporator, and then Compound A was vacuum-deposited on the hole injection layer to form a hole transport layer.

Subsequently, Compound B and Compound C were vacuum deposited on the hole transport layer at a concentration of 8% to a thickness of 300 ANGSTROM to form a light emitting layer. Compound D was vacuum deposited on the light emitting layer to a thickness of 200 Å to form an electron injection and transport layer. Aluminum was sequentially deposited on the electron injecting and transporting layer to a thickness of 12 Å and a thickness of 2000 Å to form a cathode.

Was maintained at the deposition rate 0.4 ~ 0.7Å / sec for organic material in the above process, the cathode of LiF was 0.3Å / sec, aluminum was deposited at a rate of 2Å / sec, the degree of vacuum upon deposition 2x10 ^-7 ~ 5x10 ^{- 8} torr was maintained.

Example 2

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 2 was used instead of the coating composition 1 as the hole injecting layer in Example 1.

Example 3

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 3 was used instead of the coating composition 1 as the hole injecting layer in Example 1.

Example 4

An organic light emitting device was prepared in the same manner as in Example 1, except that the hole injection layer in Example 1 was replaced with the coating composition 4 in place of the coating composition 1.

Example 5

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 5 was used instead of the coating composition 1 as the hole injection layer in Example 1.

Example 6

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 6 was used instead of the coating composition 1 as the hole injecting layer.

Example 7

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 7 was used instead of the coating composition 1 as the hole injecting layer in Example 1.

Example 8

An organic light emitting device was prepared in the same manner as in Example 1 except that the coating composition 8 was used instead of the coating composition 1 as the hole injection layer in Example 1.

Example 9

An organic light emitting device was prepared in the same manner as in Example 1, except that the hole injection layer in Example 1 was replaced with the coating composition 9 in place of the coating composition 1.

Example 10

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 10 was used instead of the coating composition 1 as the hole injection layer in Example 1.

Example 11

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 11 was used instead of the coating composition 1 as the hole injecting layer in Example 1.

Example 12

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 12 was used instead of the coating composition 1 as the hole injecting layer in Example 1.

Example 13

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 13 was used instead of the coating composition 1 as the hole injection layer in Example 1.

Example 14

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 14 was used instead of the coating composition 1 as the hole injecting layer in Example 1.

Example 15

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 15 was used instead of the coating composition 1 as the hole injection layer in Example 1.

Example 16

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 16 was used instead of the coating composition 1 as the hole injection layer in Example 1.

Example 17

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 17 was used instead of the coating composition 1 as the hole injecting layer in Example 1.

Example 18

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 18 was used instead of the coating composition 1 as the hole injection layer in Example 1.

Example 19

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 19 was used instead of the coating composition 1 as the hole injecting layer in Example 1.

Example 20

An organic light emitting device was prepared in the same manner as in Example 1, except that the coating composition 20 was used instead of the coating composition 1 as the hole injection layer in Example 1.

Comparative Example 1

An organic light emitting device was prepared in the same manner as in Example 1, except that the hole injection layer in Example 1 was replaced with the coating composition 21 in place of the coating composition 1.

Comparative Example 2

An organic light emitting device was manufactured in the same manner as in Example 1, except that the hole injection layer in Example 1 was replaced with the coating composition 22 in place of the coating composition 1.

Comparative Example 3

An organic light emitting device was manufactured in the same manner as in Example 1, except that the hole injection layer in Example 1 was replaced with the coating composition 23 in place of the coating composition 1.

The results of measuring the driving voltage and the luminous efficiency at an electric current density of 10 mA / cm < ² > are shown in Table 3 below.

Example The driving voltage (V) Current efficiency (cd / A) Power Efficiency (lm / W) Example 1 8.3 1.25 0.88 Example 2 5.8 3.65 1.12 Example 3 5.6 3.87 1.42 Example 4 6.3 2.65 0.87 Example 5 6.3 2.36 0.62 Example 6 6.5 2.11 0.89 Example 7 8.2 2.08 0.89 Example 8 5.1 1.52 0.78 Example 9 6.2 1.96 1.11 Example 10 8.4 1.11 1.01 Example 11 7.5 1.54 1.00 Example 12 7.0 3.85 1.54 Example 13 7.6 2.58 1.37 Example 14 9.1 1.37 0.75 Example 15 8.2 2.11 1.55 Example 16 8.4 2.36 1.45 Example 17 7.9 2.48 1.36 Example 18 6.2 3.33 1.72 Example 19 5.5 2.58 1.38 Example 20 8.4 3.19 1.57 Comparative Example 1 10.5 0.89 0.64 Comparative Example 2 12.1 1.05 0.57 Comparative Example 3 9.8 0.94 0.58

As a result of the above Table 3, the imonium derivative according to one embodiment of the present invention is excellent in solubility in an organic solvent and easy to produce a coating composition, so that a uniform coating layer can be formed using the coating composition .

Further, when the formed coating layer is cured, the addition of the emonium derivative facilitates curing of the charge transporting material, and a layer in which the solvent can not be washed can be formed, so that an additional layer can be laminated using a solution process , It can be used as a material of an organic light emitting device.

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

Claims (10)

1. A coating composition for an organic light emitting device comprising an imonium derivative represented by the following formula (1) and a charge transporting material represented by the following formula (3): < EMI ID =
[Chemical Formula 1]

In formula (1)
R 1 to R 4 are the same or different and each independently represents a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle,
L is a substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
(3)

In formula (3)
X1 and X2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group,
a and b are each an integer of 1 to 6,
When a and b are each 2 or more, the structures in parentheses are the same or different from each other,
A and B are the same or different from each other, and each independently hydrogen; Or deuterium,
Ar 1 and Ar 2 are the same or different and are each independently a substituted or unsubstituted aryl group,
n is an integer of 1 to 4,
When n is an integer of 2 or more, L2 of 2 or more are the same or different,
L1 is a substituted or unsubstituted arylene group,
L2 and L3 are the same or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
Y1 and Y2 are the same or different from each other and each independently is a functional group capable of crosslinking by heat or light. The method according to claim 1,
Wherein the coating composition comprises a monovalent anion. The method according to claim 1,
Wherein the coating composition comprises an anion represented by any one of the following formulas (2-1) to (2-6):
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Chemical Formula 2-5]

[Chemical Formula 2-6]

In formulas (2-1) to (2-6)
A1 is a divalent element, A2 is a trivalent element, A3 is a tetravalent element, A4 is a trivalent element and A55 is an element,
B1 to B6 are the same or different and are each independently a divalent linking group,
R5 to R20 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted aryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring. delete The method according to claim 1,
Wherein the coating composition comprises a charge transporting agent substituted with a curing agent represented by any one of the following formulas (3-1) to (3-7):
[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Chemical Formula 3-4]

[Formula 3-5]

[Chemical Formula 3-6]

[Chemical Formula 3-7]

In formulas (3-1) to (3-7)
Q are the same or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group. The method according to claim 1,
Wherein the coating composition comprises an electron acceptor. The method according to claim 1,
Wherein the coating composition comprises a compound represented by any one of the following structural formulas:

Cathode;
Anode; And
And at least one organic layer provided between the cathode and the anode,
Wherein at least one of the organic layers comprises the coating composition of any one of claims 1 to 3 and claims 5 to 7. [Claim 9] The organic light emitting device according to claim 8, wherein the organic material layer including the coating composition is a hole transporting layer, a hole injecting layer, or a layer simultaneously transporting holes and injecting holes. Preparing a substrate;
Forming a cathode or an anode on the substrate;
Forming at least one organic material layer on the cathode or the anode; And
Forming an anode or a cathode on the organic material layer,
Wherein at least one of the organic material layers is formed using the coating composition of any one of claims 1 to 3 and claims 5 to 7.

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