KR102173252B1 - Amine-based compound, organic light emitting diode using the same and method of manufacturing the same - Google Patents

Abstract

The present specification provides a coating composition including an amine-based compound, an organic light emitting device formed using the coating composition, and a method of manufacturing the same.

Description

Amine compound, organic light emitting device using the same, and manufacturing method thereof {AMINE-BASED COMPOUND, ORGANIC LIGHT EMITTING DIODE USING THE SAME AND METHOD OF MANUFACTURING THE SAME}

The present specification relates to an amine compound, a coating composition including the amine compound, an organic light emitting device formed using the coating composition, and a method of 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 material layer is placed between the anode and the cathode, when a current is applied between the two electrodes, electrons and holes are injected into the organic material layer from the cathode and the anode, respectively. The electrons and holes injected into the organic material 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 generally be composed of an organic material layer including a cathode and an anode, and an organic material layer positioned therebetween, for example, a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.

Materials used in organic light-emitting devices are pure organic materials or complex compounds in which organic materials and metals form a complex, and depending on the purpose, hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. It can be classified as Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state upon oxidation is mainly used. Meanwhile, as an electron injection material or an electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state upon reduction is mainly used. As the light-emitting layer material, a material having both p-type and n-type properties, that is, a material having a stable form in both oxidation and reduction states, is preferable, and a material with high luminous efficiency that converts excitons to light when formed is preferred. desirable.

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

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

Second, in order to obtain a high-efficiency organic light-emitting device capable of low-voltage driving, holes or electrons injected into the organic light-emitting device must be smoothly transferred to the light-emitting layer, and holes and electrons injected into the light-emitting layer must not escape out of the light-emitting layer. For this, the material used in the organic light emitting device must have an appropriate band gap and HOMO or LUMO energy level. In the case of PEDOT:PSS, which is used as a hole transport material in an organic light emitting device manufactured by the current solution coating method, the LUMO energy level is lower than the LUMO energy level of the organic material used as the light emitting layer material. Is having difficulty.

In addition, materials used in organic light-emitting devices must have excellent chemical stability, charge mobility, and interfacial properties with electrodes or adjacent layers. That is, the material used in the organic light-emitting device should be less deformed by moisture or oxygen. In addition, by having an appropriate hole or electron mobility, the density of holes and electrons in the emission layer of the organic light-emitting device should be balanced to maximize the formation of excitons. In addition, for the stability of the device, the interface with the electrode including metal or metal oxide must be improved.

Recently, an organic light emitting device has been developed using a solution process, particularly an inkjet process, in place of the existing deposition process. In this case, the cost of processing the organic light emitting device can be drastically reduced. In the early days, an attempt was made to develop an organic light-emitting device by coating all organic light-emitting device layers by a solution process, but this is limited by the current technology, so only HIL, HTL, and EML are processed as a solution process in the regular structure, and the later process is the existing deposition process. A hybrid process that utilizes is being studied. In addition, organic light-emitting materials having a polymer type have been used a lot in order to increase coating properties in the related art, but a lot of single-molecule OLED materials are currently being developed due to the batch to batch problem and purity problem inherent in polymers.

Korean Patent Application Publication No. 2012-0112277

It is an object of the present specification to provide an amine compound, a coating composition including the amine compound, an organic light emitting device formed using the coating composition, and a method of manufacturing the same.

An exemplary embodiment of the present specification provides an amine-based compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

R1 to R3 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and It is any one selected from the group consisting of a substituted or unsubstituted heterocyclic group,

L is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group,

Y1 and Y2 each independently include a photocurable group or a thermosetting group,

a to d are each independently an integer of 1 to 5,

e is an integer from 1 to 7,

When a to e are 2 or more, R1, R2, R3, Y1 and Y2 are each the same as or different from each other,

When a, b, or e is 2 or more, each of R1, R2, or R3 may combine adjacent substituents to form a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

In addition, an exemplary embodiment of the present specification includes a coating composition including the amine-based compound described above.

In addition, an exemplary embodiment of the present specification is a cathode; Anode; And one or more organic material layers provided between the cathode and the anode, and at least one of the organic material layers includes the above-described coating composition, and the cured product of the coating composition cures the coating composition by heat treatment or light treatment. It provides an organic light emitting device that is in the state.

In addition, an exemplary embodiment of the present specification includes preparing a substrate; Forming a cathode or an 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, wherein the forming of the organic material layer includes forming one or more organic material layers using the above-described coating composition,

Forming the organic material layer formed using the coating composition comprises coating the coating composition on the cathode or anode, and heat-treating or light-treating the coated coating composition. Provides.

The amine-based compound according to an exemplary embodiment of the present specification can be subjected to a solution process, and thus a large area of the device is possible. The amine-based compound according to the exemplary embodiment of the present specification may be used as an organic material layer material of an organic light emitting device, and may provide low driving voltage, high luminous efficiency, and high lifespan characteristics. The organic material layer formed by using the amine-based compound according to the exemplary embodiment of the present specification has excellent chemical resistance and film retention.

In addition, as the amine-based compound is used, solubility increases, so that the selection of a solvent is broadened and the melting point and the curing temperature can be lowered.

1 shows an example of an organic light-emitting device according to an exemplary embodiment of the present specification.
2 to 4 are MS data for confirming the synthesis of intermediates and compounds according to an exemplary embodiment of the present specification.

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

When a member is referred to herein as being “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.

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

An exemplary embodiment of the present specification provides a coating composition for an organic light-emitting device including the amine-based compound represented by Chemical Formula 1. In the case of the coating composition for an organic light-emitting device including the amine-based compound represented by Formula 1, the solubility is excellent, so it is easy to manufacture, and a uniform coating layer can be formed by using the coating composition. In addition, when used in combination with a p-doped material used as a hole injection layer, hole transport capability is improved due to the amine-based compound, resulting in a lower driving voltage and high luminous efficiency.

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

는 다른 치환기에 연결되는 부위를 의미한다.In this specification,

Means a moiety connected to another substituent.

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 as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and 2 or more When substituted, two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; Alkyl group; Alkoxy group; Alkenyl group; Silyl group; Ester group; Cycloalkyl group; Aryl group; Amine group; It means substituted or unsubstituted with one or more substituents selected from the group consisting of an arylamine group and a heterocyclic group, or substituted or unsubstituted with two or more substituents connected among the above-exemplified substituents. For example, "a substituent to which two or more substituents are connected" 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, 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-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but are 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 it is preferably 1 to 40 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. May be, but is not limited thereto.

Substituents including an alkyl group, an alkoxy group and other alkyl group moieties described in the present specification include all of the straight chain or branched form.

In the present specification, the alkenyl group may be a linear or branched chain, 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, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the ester group may be substituted with a C1-C25 linear, branched or cyclic alkyl group or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

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

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

In the present specification, the 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,

,

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.

The aryl group may be substituted with an alkyl group and may function as an arylalkyl group. The alkyl group may be selected from the above examples.

In the present specification, the heterocyclic group is a heterocyclic group including at least one of N, O, P, S, Si, and Se as a hetero atom, and the number of carbons is not particularly limited, but is preferably 1 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 1 to 30. Examples of the heterocyclic group include pyridyl group, pyrrole group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, Triazole group, oxadiazole group, thiadiazole group, dithiazole group, tetrazol group, pyranyl group, thiopyranyl group, pyrazinyl group, oxazinyl group, thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, qui Nolinyl group, isoquinolinyl group, quinolyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, acridyl 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 , A benzofuranyl group, a dibenzothiophenyl group, and a dibenzofuranyl group, but are not limited thereto.

The heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic, or condensed rings of aromatic and aliphatic.

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

In the present specification, the number of carbon atoms in the amine group is not particularly limited, but is preferably 1 to 30. The amine group may be substituted with the aforementioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof, and specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine Group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group And triphenylamine groups, but are not limited thereto.

In the present specification, the arylamine group refers to an amine group substituted with an aryl group, and the aryl group may be applied to the above example.

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

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

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, a ring formed by bonding of adjacent groups to each other may be monocyclic or polycyclic, and may form a hydrocarbon ring or a hetero ring.

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

According to an exemplary embodiment of the present specification, R1 to R3 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amine group , Any one selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group.

According to another exemplary embodiment, R1 to R3 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms, a substituted or unsubstituted carbon number Selected from the group consisting of an alkoxy group of 1 to 40, a substituted or unsubstituted amine group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms It is one that becomes.

According to another exemplary embodiment, R1 to R3 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 40 carbon atoms, a substituted or unsubstituted carbon number It is any one selected from the group consisting of 6 to 60 aryl groups and substituted or unsubstituted C 2 to C 60 heterocyclic groups.

According to another exemplary embodiment, R1 to R3 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 40 carbon atoms, and a substituted or unsubstituted carbon number. It is any one selected from the group consisting of 6 to 60 aryl groups.

According to another exemplary embodiment, R1 to R3 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, and a substituted or unsubstituted carbon number. It is any one selected from the group consisting of 6 to 30 aryl groups.

According to another exemplary embodiment, R1 to R3 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a phenyl group, a biphenyl group, It is a naphthylenyl group or a phenanthryl group.

According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.

According to another exemplary embodiment, L is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

According to another exemplary embodiment, L is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

According to another exemplary embodiment, L is a phenyl group, a biphenyl group, a naphthylenyl group, or a phenanthryl group.

According to another exemplary embodiment, L is a phenyl group.

In the present specification, the term "thermosetting group or photocurable group" may mean a reactive substituent for crosslinking compounds by exposure to heat and or light. Crosslinking may be generated by heat treatment or light irradiation, as the carbon-carbon multiple bonds and cyclic structures are decomposed and radicals generated are connected.

이고, 상기 열경화성기 또는 광경화성기가 열처리 또는 광처리에 의하여 가교되는

의 구조로 다른 아민계 화합물과 연결될 수 있다.For example, the thermosetting group or photocurable group

And the thermosetting group or photocurable group is crosslinked by heat treatment or light treatment

It can be connected to other amine compounds by the structure of.

According to the exemplary embodiment of the present specification, each of Y1 and Y2 independently includes a thermosetting group or a photocurable group, and the thermosetting group or photocurable group is selected from the following structures.

In the above structure, R7 is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to another exemplary embodiment, R7 is hydrogen or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, R7 is hydrogen or an alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, R7 is hydrogen or an alkyl group having 1 to 6 carbon atoms.

In the exemplary embodiment of the present specification, in the case of an amine-based compound containing a thermosetting group or a photocurable group, an organic light-emitting device can be manufactured by a solution coating method, so there is an economic effect in terms of time and cost.

In addition, when a coating layer is formed using a coating composition containing an amine-based compound containing a thermosetting group or a photocurable group, since the thermosetting group or the photocurable group is crosslinked by heat or light, additional When the layers are stacked, the amine compound contained in the coating composition is prevented from being washed away by the solvent, so that an additional layer can be stacked on the top while maintaining the coating layer.

In addition, when the coating layer is formed by crosslinking the thermosetting group or the photocurable group, the chemical resistance of the coating layer to the solvent is increased, and the film retention rate is high.

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

According to an exemplary embodiment of the present specification, in the case of an amine-based compound crosslinked by heat treatment or light irradiation, a plurality of amine-based compounds are crosslinked to be provided in the organic light emitting device in the form of a thin film, so that thermal stability is excellent. Therefore, the organic light-emitting device using the amine-based compound according to the exemplary embodiment of the present specification has an effect of excellent life characteristics.

In addition, since the amine-based compound according to the exemplary embodiment of the present specification includes an amine structure in the core structure, it may have an energy level and a band gap suitable as a hole injection, a hole transport material, or a light emitting material in an organic light emitting device. In addition, by adjusting the substituent of the compound of Formula 1 according to an exemplary embodiment of the present specification, an appropriate energy level and band gap can be finely adjusted, and interface characteristics between organic substances are improved, thereby reducing driving voltage and high luminous efficiency. It is possible to provide an organic light emitting device having.

According to an exemplary embodiment of the present invention, the compound of Formula 1 is any one selected from the following compounds.

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

For example, the compound of Formula 1 may have a core structure as shown in Scheme 1 below. Substituents may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

[Scheme 1]

The present specification also provides a coating composition comprising the above-described amine-based compound.

In one embodiment of the present specification, the coating composition may be a liquid. The "liquid" means that it is in a liquid state at room temperature and pressure.

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

In an exemplary embodiment of the present specification, the solvent is, for example, a chlorine-based solvent 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, cyclohexanone, isophorone, tetralone, decalone, and acetylacetone; Ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyvalents such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, etc. Alcohol and its derivatives; Alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide 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 any solvent capable of dissolving or dispersing the carbazole derivative according to an exemplary embodiment of the present invention is not sufficient, and these are not limited.

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

In the exemplary 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 thermosetting group or a photocurable group is introduced into the molecule.

In the exemplary embodiment of the present specification, the coating composition may further include a compound in which a thermosetting group or a photocurable group is introduced into the molecule. When the coating composition further includes a compound having a thermosetting group or a photocurable group introduced into the molecule, the degree of curing of the coating composition may be further increased.

In an exemplary embodiment of the present specification, the molecular weight of the compound into which a thermosetting group or a photocurable group is introduced is 100 g/mol to 1,500 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 viscosity suitable for coating or inkjet.

In one embodiment of the present specification, the viscosity of the coating composition is 2 cP to 15 cP. When it has a viscosity in the above range, it is easy to manufacture a device.

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

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

As a thermal polymerization initiator, methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, methyl cyclohexanone peroxide, cyclohexanone peroxide, isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide , Bis-3,5,5-trimethyl hexanoyl peroxide, lauryl peroxide, benzoyl peroxide, p-crole benzoyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-(t-butyl Oxy)-hexane, 1,3-bis(t-butyl peroxy-isopropyl) benzene, t-butyl cumyl peroxide, di-tbutyl peroxide, 2,5-dimethyl-2,5-( Dit-butyl peroxy) hexane-3, tris-(t-butyl peroxy) triazine, 1,1-dit-butyl peroxy-3,3,5-trimethyl cyclohexane, 1,1-dit -Butyl peroxy cyclohexane, 2,2-di (t-butyl peroxy) butane, 4,4-di-t-butyric acid valeric acid n-butyl ester, 2,2-bis (4, 4-t-butyl peroxy cyclohexyl) propane, t-butylperoxyisobutylate, dit-butyl peroxy hexahydro terephthalate, t-butyl peroxy-3,5,5-trimethylhexaate, t- There are peroxides such as butyl peroxybenzoate and dit-butyl peroxy trimethyl adipate, or azo systems such as azobis isobutyl nitrile, azobisdimethylvaleronitrile, and azobis cyclohexyl nitrile, but are not limited thereto.

As a photoinitiator, diethoxy acetophenone, 2,2-dimethoxy-1,2-diphenyl ethan-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 4-(2-hydroxy ethoxy) Phenyl-(2-hydroxy-2-propyl) ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl) butanone- 1,2-hydroxy-2-methyl-1-phenyl Propan-1-one, 2-methyl-2-morpholino (4-methyl thiophenyl) propan-1-one, 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl) oxime , Acetophenone-based or ketal-based photopolymerization initiators, benzoin, benzoin methylate, benzoin ethylate, benzoin isobutyrate, benzoin isopropyrate, and other benzoin ethers Benzophenone photopolymerization initiators such as photopolymerization initiators, benzophenone, 4-hydroxybenzophenone, 2-benzoyl naphthalene, 4-benzoyl biphenyl, 4-benzoyl phenyl ether, acrylated benzophenone, 1,4-benzoyl benzene, Thioxanthone photoinitiators such as 2-isopropyl thioxanthone, 2-chloro thioxanthone, 2,4-dimethyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-dichloro thioxanthone, etc. As other photoinitiators, ethyl anthraquinone, 2,4,6-trimethylbenzoyl diphenyl phosphine oxide, 2,4,6-trimethylbenzoyl phenyl ethoxy phosphine oxide, bis(2,4,6-trimethylbenzoyl) Phenylphosphine oxide, bis(2,4-dimethoxybenzoyl)-2,4,4-trimethyl pentylphosphine oxide, methylphenirgrioxystel, 9,10-phenanthrene, acridine compound, tria True compounds and imidazole compounds. Moreover, what has a photopolymerization accelerating effect can also be used individually or in combination with the said photoinitiator. For example, triethanolamine, methyl diethanol amine, 4-dimethylamino benzoate ethyl, 4-dimethylamino benzoate isoamyl, benzoic acid (2-dimethylamino) ethyl, 4,4'-dimethylaminobenzophenone, etc. It is not limited to this.

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

In another exemplary embodiment, the coating composition further includes a p-doped material.

In the present specification, the p-doped material refers to a material that makes the host material have p semiconductor properties. The p-semiconductor property refers to a property of injecting or transporting holes at the highest occupied molecular orbital (HOMO) energy level, that is, a property of a material having a high hole conductivity.

In the exemplary embodiment of the present specification, the p-doped material may be represented by any one of the following structures.

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

In the exemplary 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 is preferably 1 to 30% by weight based on the total solid content of the coating composition, and in another embodiment, the p-doped material The content of is more preferably 10 to 30% by weight based on the total solid content of the coating composition.

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

As in the exemplary embodiment of the present specification, the coating composition is a single molecule containing a thermosetting group or a photocurable group; Alternatively, when a single molecule containing a terminal group capable of forming a polymer by heat is further included, the curing temperature may be lowered, and it is more preferable to have similar structures that do not affect the physical properties of the amine compound of the present specification. .

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

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

An exemplary embodiment of the present specification is a cathode; Anode; And one or more organic material layers provided between the cathode and the anode, and at least one of the organic material layers includes a cured product of the above-described coating composition, and the cured product of the coating composition heat-treats or light-treats the coating composition. It provides an organic light emitting device that is in a cured state by.

In an exemplary embodiment of the present specification, the organic material layer including the cured product of the coating composition is a hole transport layer, a hole injection layer, or a layer that simultaneously transports and injects holes.

In another exemplary embodiment, the organic material layer including the cured product of 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 an emission layer, and the emission layer includes the amine compound as a host of the emission layer.

In the exemplary embodiment of the present specification, the organic light emitting device is a hole injection layer and a hole transport layer. It further includes one or two 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 a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In another exemplary embodiment, the organic light-emitting device may be an organic light-emitting device of an inverted type 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 multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present specification 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, and the like 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 the organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIG. 1.

1 shows 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.

In FIG. 1, the hole injection layer 301 is formed by using a coating composition containing an amine compound.

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 of the organic material layers is formed using a coating composition including the amine compound.

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

An exemplary embodiment of the present specification provides a method of manufacturing an organic light emitting device formed by using the coating composition.

Specifically, in the exemplary embodiment of the present specification, the step of preparing a substrate; Forming a cathode or an anode on the substrate; Forming one or more organic material layers on the cathode or anode; And in the step of forming the organic material layer, one or more organic material layers are formed using the above-described 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 exemplary embodiment, the organic material layer formed using the coating composition is formed by inkjet printing.

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

In the state of the present specification, the printing method includes, for example, a nozzle printing method, an offset printing method, a transfer printing method or a screen printing method, but is not limited thereto.

The coating composition according to an exemplary embodiment of the present specification has structural characteristics and is suitable for a solution process and can be formed by a printing method, so that there is an economic effect in terms of time and cost when manufacturing a device.

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

In the exemplary embodiment of the present specification, the heat treatment temperature in the heat treatment step is 85 to 300.

In another exemplary embodiment, the heat treatment time in the heat treatment step may be 1 minute to 1 hour.

In the exemplary embodiment of the present specification, when the coating composition does not contain an additive, it is preferable that crosslinking proceeds by heat treatment at a temperature of 100°C to 300°C, and crosslinking proceeds at a temperature of 150°C to 250°C. It is more preferable to be.

In addition, although the coating composition of the present specification may further include an initiator, it is more preferable not to use it.

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, a plurality of amine-based compounds included in the coating composition may crosslink to provide an organic material layer including a thinned structure. . In this case, the organic material layer formed by using the coating composition can be prevented from being dissolved, morphologically affected, or decomposed by a solvent applied on the surface.

Therefore, when the organic material layer formed by using the coating composition is formed including the heat treatment or light treatment step, the resistance to the solvent increases, so that the solution deposition and crosslinking method are repeatedly performed to form a multilayer, and the stability of the device is increased. It can increase the life characteristics.

In the exemplary embodiment of the present specification, the coating composition including the amine-based compound may be mixed and dispersed in a polymeric binder.

In one embodiment of the present specification, as the polymeric binder, those that do not extremely inhibit charge transport, and those that do not have strong absorption of visible light are preferably used. As the polymeric binder, poly(N-vinylcarbazole), polyaniline and derivatives thereof, polythiophene and derivatives thereof, poly(p-phenylenevinylene) and derivatives thereof, poly(2,5-thienylenevinylene) and Derivatives thereof, polycarbonate, polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane, and the like are exemplified.

In addition, the amine-based compound according to the exemplary embodiment of the present specification includes fluorene and an amine group, so that the amine-based compound alone may be included in the organic material layer, and the coating composition including the amine-based compound is thinned through heat treatment or light treatment. It may proceed, and may be included as a copolymer by using a coating composition mixed with other monomers. In addition, by using a coating composition mixed with another polymer, it may be included as a copolymer or a mixture.

As the anode material, a material having a large work function is preferred so that holes can be smoothly injected into the organic material layer. 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); A combination of a metal and an oxide such as ZnO:Al or SnO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

The cathode material is generally 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; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that injects holes from an electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material. A compound that prevents the movement of 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 HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, etc., 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 emission layer.The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

The light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

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, and periflanthene having an arylamino group, and the styrylamine compound is substituted or unsubstituted A compound in which at least one arylvinyl group is substituted on the arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer.As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer is suitable. Do. Specific examples include the 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 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 layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.

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

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

The hole blocking layer is a layer that prevents holes 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 complexes, etc., but are not limited thereto.

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

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

Hereinafter, examples will be described in detail in order to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various 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 completely describe the present specification to those of ordinary skill in the art.

Preparation Example 1. Preparation of Chemical Formula 1-1

2,2'-(5'- chloro -[1,1':3',1''- terphenyl ]-4,4''- diyl )bis(1,3- dioxolane ) Synthesis of (Compound 2)

[Scheme 1]

Add 1,3-dibromo-5-chlorobenzene (10g, 36.98mmol), (4-formylphenyl)boronic acid (11.4g, 75.8mmol), and potassium carbonate (15.33g, 110.09mmol) to a 1L round bottom flask (RBF). 200 ml of toluene, 100 ml of Ethanol, and 100 ml of water were added and dissolved by stirring at 80 °C. When the reaction material was completely dissolved in the solvent, Tetrakis (triphenylphosphine) palladium (2.14g, 1.849mmol) was added and reacted for 24 hours. After lowering the temperature and extracting with EA and water, the residual water was removed with MgSO ₄ , stirred in charcol, passed through a silica gel pad, the solvent was removed, and white crystals were obtained using THF and methanol. (Yield: 62%)

5'-chloro-[1,1':3',1''-terphenyl]-4,4''-dicarbaldehyde (Compound 1) (7.35g, 22.91mmol) obtained above was added to 250mL RBF and 100ml of toluene was added. After that, TsOH (0.04g, 0.23mmol) and Ethylene glycol (5.1ml, 91.64mmol) were added and dean-stark was installed, and the reaction was performed for 24 hours while draining water at high temperature. After quenching with NaHCO ₃ , work-up with EA and Brine, residual water was removed with MgSO ₄ , filtered, and the solvent was removed. After column with EA:Hex=1:5, precipitated with EA and Hex and filtered to obtain a white solid. (Yield: 53%) The results of synthesizing Compound 2 are shown in Fig. 2 showing the H NMR results.

[Scheme 2]

In 250mL RBF, add 4-(phenylamino)phenol (2.29g, 12.35mmol), compound 2 (5g, 12.23mmol), NaOtBu (5.93g, 61.75mmol) and N ₂ purging. 50ml of N ₂ bubbling toluene was added and dissolved by stirring up to 90°C. When the reaction material was completely dissolved in the solvent, Pd(PtBu ₃ ) ₂ (0.31g, 0.61mmol) was added and reacted for 3 hours. When it is confirmed that all the spots of Compound 2 have disappeared on TLC, lower the temperature, work-up with EA and Brine, remove residual water with MgSO ₄ , stir in charcoal, pass through a silica gel pad, remove the solvent, and EA:Hex= Flash column 1:2 to obtain a light brown solid compound 3. (Yield: 80%)

Compound 3 (5.05g, 9.06mmol), PBSF (4.88ml, 27.17mmol), K ₂ CO ₃ (3.76g, 27.17mmol) was added to 100mL RBF, and 30ml of Acetone and 15ml of DI water were added to dissolve. It reacted overnight. After confirming that the compound 5 disappeared by TLC, work-up with EA and Brine, the residual water was removed with Na ₂ SO ₄ and the solvent was removed and flash column with EA:Hex=1:3 to obtain a red solid compound 4. . (Yield: 90%)

[Scheme 3]

Add (9-phenyl-9H-carbazol-3-yl)boronic acid (1.499g, 5.22mmol), compound 4 (4.3g, 5.12mmol), K ₂ CO ₃ (2.12g, 15.36mmol) to 100mL RBF and toluene Add 20ml, 10ml of ethanol, and 10ml of DI water to dissolve by heating to 90°C. When the reaction product is completely dissolved, Pd(PPh ₃ ) ₄ (0.295g, 0.26mmol) is added and reacted for about 12 hours. After confirming that the compound 4 disappeared by TLC, work-up with EA/water, remove the residue with MgSO ₄ , stir in charcoal, pass through a silica gel pad, remove the solvent, and flash column with EA:Hex=1:3. A white solid compound 5 was obtained. (Yield: 50%)

Compound 5 was dissolved in THF, DI water and 1N HCl (catalyst) were added, followed by refluxing at 70° C. and stirred for 3 hours. After confirming that the reaction proceeded cleanly with one-spot on TLC, work-up with EA/Brine, the residual water was removed with Na ₂ SO ₄ and the solvent was removed to obtain a yellow solid compound 6 without any further purification.

Weigh CH ₃ PPh ₃ Br (7.2 g, 20.10 mmol) and t-BuOK (2.05 g, 18.30 mmol) vacuum-dried at 50°C in 250 mL RBF, purged with nitrogen gas, and then distilled THF in an ice bath to 70 mL. The mixture was poured and stirred for 1 hour to obtain a product. Again, the temperature of the bath was adjusted to 0 °C, and compound 6 was dissolved in 50 ml of distilled THF, followed by olefination reaction for about 2 hours. After confirming that the reaction is over, terminate it with water, work-up with EA and Brine, remove the residue with Na ₂ SO ₄ , blow off the solvent and add TEA to inactivate silica gel and load it as a solid into EA:Hex=1:50 Flash column. After removal of the solvent, it was recrystallized using MC and EA to obtain a white solid (Compound 1-1). (Yield: 64%) The mass spectrometry spectrum is shown in FIG. 3 as synthesis confirmation data for Compound 1-1.

Example 1

IB VNPB

Compound 5 Compound 6 Compound 7

The P-doped material (IB); The compound VNPB; And an organic solvent (cyclohexanone: cyclohexanone) was mixed to prepare a coating composition. The ratio of VNPB:p-dopant was mixed at a weight ratio of 0.8:0.2. A glass substrate on which ITO (indium tin oxide) was deposited with a thickness of 1500Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating 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, followed by drying, and the substrate was transported to a glove box. The coating composition was spin-coated on the prepared ITO transparent electrode to form a hole injection layer having a thickness of 300 Å, and the coating composition was cured on a hot plate at 220 ^° C. for 30 minutes in an N ₂ atmosphere. The hole injection layer on the organic solvent, the above formula 1-1 (toluene: toluene) in a weight ratio of 1% was applied by spin coating the dissolved composition to form a hole transport layer of 400Å thickness and N ₂ 230 ℃ on a hot plate in an atmosphere, and 30 minutes of The coating composition was cured under conditions. Thereafter, the device was fabricated by sequentially depositing Compound 7 and Compound 8 (8% concentration, 300 Å), Compound 9 (200 Å), LiF (12 Å), and Al (2000 Å) by moving to a vacuum evaporator. In the above process, the deposition rate of organic materials was maintained at 0.4 ~ 0.7Å/sec, the deposition rate of LiF of the cathode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 2x10 ^-7 ~ 5x10. ^-8 torr was maintained.

Example 2

The device was removed in the same manner as in Example 1, except that Formula 1-5 was used instead of Formula 1-1.

Example 3

The device was removed in the same manner as in Example 1, except that Formula 1-7 was used instead of Formula 1-1.

Example 4

The device was removed in the same manner as in Example 1, except that Formula 1-11 was used instead of Formula 1-1.

Comparative Example 1

Compound A

A device was manufactured in the same manner as in Example 1, except that Compound A was used instead of Formula 1-1.

Driving voltage (V) Current efficiency (cd/A) Power efficiency (lm/W) Example 1 5.94 4.88 2.58 Example 2 4.35 4.64 3.35 Example 3 5.81 5.42 2.93 Example 4 4.98 4.77 3.01 Comparative example 6.23 3.09 1.45

Looking at Table 1, it can be seen that the Comparative Example exhibits lower current efficiency and power efficiency compared to Examples 1 to 4.

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

Claims (8)

An amine compound represented by the following formula (1):
[Formula 1]

In Formula 1,
R1 is the same as or different from each other, and each independently hydrogen; Or an aryl group,
R2 is the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,
R3 is hydrogen,
L is an arylene group,
Y1 and Y2 are

ego,
a to d are each 5,
e is 7,
At least one of R2 is a substituted or unsubstituted alkyl group. delete The method according to claim 1,
Formula 1 is an amine compound that is any one selected from the following compounds:

. A coating composition comprising the amine-based compound according to any one of claims 1 and 3. The coating composition of claim 4, wherein the coating composition further comprises a p-doped material represented by any one of the following structures:

. Cathode;
Anode; And
Including one or more organic material layers provided between the cathode and the anode,
At least one layer of the organic material layer comprises a cured product of the coating composition of claim 4,
The cured product of the coating composition is an organic light-emitting device in a state cured by heat treatment or light treatment of the coating composition. The organic light-emitting device of claim 6, wherein the organic material layer including the cured product of the coating composition is a hole transport layer, a hole injection layer, or a layer that simultaneously transports and injects holes. Preparing a substrate;
Forming a cathode or an anode on the substrate;
Forming one or more organic material layers on the cathode or anode; And
Including the step of forming an anode or 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 4,
Forming the organic material layer formed using the coating composition comprises coating the coating composition on the cathode or anode, and heat-treating or light-treating the coated coating composition. .

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