KR20220057190A - Novel compound, coating composition comprising same, organic light emitting device using same and method of manufacturing same - Google Patents

Abstract

The present specification relates to a compound represented by chemical formula 1, a coating composition comprising the compound represented by chemical formula 1, an organic light emitting device using the same, and a method for manufacturing the same. According to the present invention, the compound represented by chemical formula 1 has excellent solubility to an organic solvent, so that the compound is not crystallized in a coating composition when the compound is dissolved in the organic solvent to form the coating composition.

Description

A novel compound, a coating composition comprising the same, an organic light emitting device using the same, and a manufacturing method thereof {NOVEL COMPOUND, COATING COMPOSITION COMPRISING SAME, ORGANIC LIGHT EMITTING DEVICE USING SAME AND METHOD OF MANUFACTURING SAME}

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

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

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

Accordingly, there is a demand for development of materials for solution processing.

Korean Patent Publication No. 10-2000-0051826

An object of the present specification is to provide a novel compound and an organic light emitting device including the same.

A compound represented by the following formula (1) is provided.

[Formula 1]

In Formula 1,

L1 to L4 are the same as or different from each other, and are each independently a substituted or unsubstituted arylene group,

Y1 to Y4 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted an aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group or a curable group, and at least one of Y1 to Y4 is a curable group,

R1 to R5 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted an aryloxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

n1 and n4 are each an integer from 0 to 4,

n2 and n3 are each an integer from 0 to 3,

n5 is an integer from 0 to 5,

When each of n1 to n5 is 2 or more, the substituents in the parentheses of 2 or more are the same as or different from each other,

m is an integer from 3 to 10;

The present specification provides a coating composition comprising the compound.

The present specification also includes a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the one or more organic material layers provides an organic light emitting device including the above-described coating composition or a cured product thereof.

Finally, the present specification includes the steps of preparing a first electrode; forming one or more organic material layers on the first electrode; and forming a second electrode on the one or more organic material layers, wherein the forming of the one or more organic material layers includes forming one or more organic material layers using the coating composition. A method of manufacturing a device is provided.

The compound of Formula 1 of the present invention can be used as a material for an organic material layer of an organic light-emitting device, and a device having a low driving voltage, excellent luminous efficiency and lifespan characteristics can be obtained, and a solution process is possible, so that a large area of the device is possible. .

According to an exemplary embodiment of the present invention, when the coating composition is formed by dissolving the compound of Formula 1 in an organic solvent, the coating composition has a viscosity suitable for a solution process, and the compound of Formula 1 has solubility in an organic solvent It has the advantage that it is not crystallized in the coating composition because it is excellent.

In addition, when the organic material layer containing the compound of Formula 1 of the present invention is formed through a solution process and then the organic material layer of the upper layer is formed through a solution process, the organic layer containing the compound of Formula 1 does not dissolve in the solution process solvent of the upper layer, so the device The advantage is that the performance of the

1 illustrates an example of an organic light emitting device according to an exemplary embodiment of the present specification.

Hereinafter, the present specification will be described in detail.

In the present specification, when a member (layer) is said to be located “on” another member (layer), this is not only when a member (layer) is in contact with another member but also between two members (layers). (layer) is also included.

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

As used herein, the term “curable group” refers to a photocurable group or a thermosetting group, and may refer to a reactive substituent for crosslinking between compounds by exposure to heat and/or light. Crosslinking may be generated while radicals generated while decomposing carbon-carbon multiple bonds or cyclic structures are connected by heat treatment or light irradiation.

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

In the present specification, "-----" refers to a site bonded to another substituent or a bonding portion.

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

As used herein, the term "substituted or unsubstituted" is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryl group, and a heteroaryl group, It means that it is unsubstituted or substituted with a substituent to which two or more substituents are connected among the above-exemplified substituents. For example, "a substituent in which two or more 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 addition, as used herein, the term “substituted or unsubstituted” refers to deuterium, a halogen group, a nitrile group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, 6 to 60 carbon atoms. It means that it is unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 2 to 60 carbon atoms, or substituted or unsubstituted with a substituent to which two or more substituents among the above-exemplified substituents are connected.

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 20. According to another exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 10. Specific examples of the alkyl group include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, etc. , but not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but may have 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group may have 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. Specific examples of the cycloalkyl group include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like.

In the present specification, the alkoxy group may be linear or branched. The number of carbon atoms of the alkoxy group is not particularly limited, but may be 1 to 20 carbon atoms. Specific examples of the alkoxy group include a methoxy group, an ethoxy group, n-propoxy group, n-butoxy group, tert-butoxy group, n-pentyloxy group, n-hexyloxy group, n-octyloxy group, n-no It may be a nyloxy group, an n-decyloxy group, etc., but is not limited thereto.

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

a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, S, Si and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but may have 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a pyridazine group, a furan group, a thiophene group, a benzothiophene group, a benzofuran group, a dibenzothiophene group, a dibenzofuran group, a carbazole group and the like, but is not limited thereto.

In the present specification, the description of the above-mentioned heterocyclic group is applied except that the heteroaryl group is aromatic.

In the present specification, the description of the above-described aryl group is applied to the aryl group of the aryloxy group.

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

As used herein, the "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. 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.

In the present specification, in a substituted or unsubstituted ring formed by bonding to each other, "ring" is a hydrocarbon ring; or a heterocyclic ring. The hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic. The description of the heterocyclic group may be applied except that the heterocycle is divalent.

In the present specification, the description of the above-described aryl group may be applied, except that the aromatic hydrocarbon ring is divalent.

In the present specification, the description of the above-described cycloalkyl group may be applied, except that the aliphatic hydrocarbon ring is divalent.

According to an exemplary embodiment of the present specification, there is provided a compound represented by Formula 1 above.

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

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

According to an exemplary embodiment of the present specification, Y1 to Y4 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or an unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group or a curable group, and at least one of Y1 to Y4 is a curable group.

In another exemplary embodiment, Y1 to Y4 are the same as or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a substituted or unsubstituted C _1-20 alkyl group or a curable group, and among Y1 to Y4 1 or more is a curable group.

According to another exemplary embodiment, Y1 to Y4 are the same as or different from each other, and each independently represent hydrogen, a fluoro group, a methyl group, a tert-butyl group, or a curable group, and at least one of Y1 to Y4 is a curable group .

According to another exemplary embodiment, 1 to 4 of Y1 to Y4 are curable groups.

In another exemplary embodiment, one to two of Y1 to Y4 are curable groups.

In another exemplary embodiment, three of Y1 to Y4 are curable groups.

According to another exemplary embodiment, two of Y1 to Y4 are curable groups.

In another exemplary embodiment, any one of Y1 and Y2 is a curable group, and the other one is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or an unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, wherein any one of Y3 and Y4 is a curable group, and the other is hydrogen , deuterium, halogen group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted aryl group or substituted Or an unsubstituted heterocyclic group.

According to another exemplary embodiment, any one of Y1 and Y2 is a curable group, and the other one is hydrogen, deuterium, a halogen group, or a substituted or unsubstituted C _1-20 alkyl group, and any one of Y3 and Y4 One is a curable group, and the other is hydrogen, deuterium, a halogen group, or a substituted or unsubstituted C _1-20 alkyl group.

In another exemplary embodiment, any one of Y1 and Y2 is a curable group, the other is hydrogen, a fluoro group, a methyl group, or a tert-butyl group, and any one of Y3 and Y4 is a curable group, The other one is hydrogen, a fluoro group, a methyl group, or a tert-butyl group.

According to an exemplary embodiment of the present specification, the curable group is any one of the following structures.

는 결합되는 위치를 나타낸다.In the above structures,

indicates a binding position.

또는

이다.In one embodiment of the present specification, the curable group

or

am.

는 3 이상의 치환 또는 비치환된 벤젠고리가 선형(linear)으로 연결된 치환기이며, 상기

이 치환 또는 비치환된 벤젠고리가 1개 또는 2개 연결된 치환기인 화합물 보다 소자에 적용 시 매우 향상된 특성(구동전압, 효율 및 수명)을 갖는다.In Formula 1 above

is a substituent in which three or more substituted or unsubstituted benzene rings are linearly connected, and

This substituted or unsubstituted benzene ring has significantly improved properties (driving voltage, efficiency, and lifespan) when applied to a device than a compound having one or two connected substituents.

는 하기 구조일 수 있다.According to an exemplary embodiment of the present specification, the

may have the following structure.

는 아민기에 결합되는 위치를 나타낸다.The structure may be substituted with additional substituents,

represents a position bonded to an amine group.

는 하기 구조일 수 있다.In one embodiment of the present specification, the

may have the following structure.

는 아민기에 결합되는 위치를 나타낸다.The structure may be substituted with additional substituents,

represents a position bonded to an amine group.

는 하기 구조일 수 있다.In one embodiment of the present specification, the

may have the following structure.

는 아민기에 결합되는 위치를 나타낸다.The structure may be substituted with additional substituents,

represents a position bonded to an amine group.

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

[Formula 2]

In Formula 2,

The definitions of L1 to L4, Y1 to Y4, R1 to R4 and n1 to n4 are the same as in Formula 1,

R11 to R13 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted an aryloxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

n11 and n12 are each an integer from 0 to 4,

n13 is an integer from 0 to 5,

When each of n11 to n13 is two or more, the substituents in the two or more parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, R11 to R13 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C _1-20 alkyl group, a substituted or unsubstituted C _3-20 cycloalkyl group, substituted or unsubstituted C _1-20 alkoxy group, substituted or unsubstituted C _6-30 aryloxy group, substituted or unsubstituted C _6-30 aryl group or substituted or It is an unsubstituted C _2-30 heterocyclic group.

According to another exemplary embodiment, R11 to R13 are each hydrogen.

According to an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently represents a substituted or unsubstituted C _6-30 arylene group.

In an exemplary embodiment of the present specification, L1 to _L4 are the same as or different from each other, and each independently C ₆ - It is an arylene group of ₃₀ .

According to another exemplary embodiment, L1 to L4 are the same as or different from each other, and each independently represent a substituted or unsubstituted phenylene group.

In another exemplary embodiment, L1 to L4 are the same as or different from each other, and each independently a phenylene group unsubstituted or substituted with one or more substituents among a halogen group and a substituted or unsubstituted C _1-20 alkyl group. .

According to another exemplary embodiment, L1 to L4 are the same as or different from each other, and each independently represents a phenylene group unsubstituted or substituted with one or more of a fluoro group, a methyl group, and a tert-butyl group.

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

[Formula 3]

In Formula 3,

Y1 to Y4, R1 to R5, n1 to n5 and m have the same definitions as in Formula 1,

R21 to R24 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted an aryloxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

n21 to n24 are each an integer of 0 to 4,

When each of n21 to n24 is 2 or more, the substituents in the two or more parentheses are the same as or different from each other.

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

[Formula 3-1]

In Formula 3-1,

Y1 to Y4, R1 to R4 and n1 to n4 have the same definitions as in Formula 1,

R11 to R13 and R21 to R24 are the same as or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, A substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

n11, n12 and n21 to n24 are each an integer of 0 to 4,

n13 is an integer from 0 to 5,

When n11 to n13 and n21 to n24 are 2 or more, respectively, the substituents in the two or more parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, R21 to R24 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C _1-20 alkyl group, a substituted or unsubstituted C _3-20 cycloalkyl group, substituted or unsubstituted C _1-20 alkoxy group, substituted or unsubstituted C _6-30 aryloxy group, substituted or unsubstituted C _6-30 aryl group or substituted or It is an unsubstituted C _2-30 heterocyclic group.

In another exemplary embodiment, R21 to R24 are hydrogen, a halogen group, or a substituted or unsubstituted C _1-20 alkyl group.

According to another exemplary embodiment, R21 to R24 are hydrogen, a fluoro group, a methyl group, or a tert-butyl group.

In the exemplary embodiment of the present specification, n21 to n24 are each an integer of 0 to 2, and when n21 to n24 are each 2, the substituents in the two parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C _1-20 alkyl group, a substituted or unsubstituted C _3-20 cycloalkyl group, substituted or unsubstituted C _1-20 alkoxy group, substituted or unsubstituted C _6-30 aryloxy group, substituted or unsubstituted C _6-30 aryl group or substituted or It is an unsubstituted C _2-30 heterocyclic group.

According to an exemplary embodiment of the present specification, R1 to R5 are each hydrogen.

According to an exemplary embodiment of the present specification, m is an integer of 3 to 10.

In another exemplary embodiment, m is 3.

In an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following compounds.

The compound of Formula 1 according to an exemplary embodiment of the present specification can be synthesized by an amination reaction (Buchwald-Hartwig amination) of an aryl compound containing an amine group and a bromo compound containing a curing group in a toluene solvent, and the aryl compound is water An aryl compound having a halogen substituent and an aryl compound having a boronic acid or boronic ester substituent can be synthesized through a Suzuki coupling reaction in a co-solvent of tetrahydrofuran and tetrahydrofuran. A more detailed synthesis method was described in the synthesis example.

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

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

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

In one 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, 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, and 1,2-hexanediol alcohols and derivatives thereof; 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 compound of Formula 1 according to an exemplary embodiment of the present invention is sufficient, and the present invention is not limited thereto.

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

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

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

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

In the exemplary embodiment of the present specification, the content of the p-doping material is 0 wt% to 50 wt% based on the compound of Formula 1 above.

In an exemplary embodiment of the present specification, the content of the p doping material includes 0 to 30% by weight based on the total solid content of the coating composition. In an exemplary embodiment of the present specification, the content of the p doping material is preferably 1 to 30% by weight based on the total solid content of the coating composition, and in another exemplary embodiment, the p doping material The content of the coating composition more preferably includes 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 comprising a photocurable group and / or thermosetting group; Alternatively, it may further include a single molecule including a terminal group capable of forming a polymer by heat. Monomolecules containing a photocurable group and/or a thermosetting 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 3,000 g/mol or less.

a single molecule comprising the photocurable group and/or the thermosetting group; Alternatively, a single molecule including a terminal group capable of forming a polymer by heat may be aryl such as phenyl, biphenyl, fluorene, or naphthalene; arylamine; Alternatively, it may refer to a single molecule in which a photocurable group and/or a thermosetting group or a terminal group capable of forming a polymer by heat is substituted with fluorene.

In another exemplary embodiment, the viscosity of the coating composition is 2 cP to 15 cP at room temperature (about 25° C.).

When the above viscosity is satisfied, it is easy to manufacture a device.

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

In one embodiment of the present specification, the first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the one or more organic material layers includes the coating composition or a cured product thereof, and the cured product of the coating composition comprises: The coating composition is in a cured state by heat treatment or light treatment.

In an exemplary embodiment of the present specification, the organic material layer including the coating composition or a cured product thereof is a hole transport layer or a hole injection layer.

In an exemplary embodiment of the present specification, the organic material layer including the coating composition or a cured product thereof is an electron transport layer or an electron injection layer.

In another exemplary embodiment, the organic material layer including the coating composition or a cured product thereof is a light emitting layer.

In another exemplary embodiment, the organic material layer including the coating composition or a cured product thereof is an emission layer, and the emission layer includes the compound of Formula 1 as a host of the emission layer.

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

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

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

According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

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 inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole injection and transport layer, an electron injection and transport layer, etc. 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, a first electrode 201, a hole injection layer 301, a hole transport layer 401, a light emitting layer 501, an electron injection and transport layer 601 and a second electrode 701 are sequentially shown on a substrate 101 The structure of the organic light-emitting device stacked with Here, the electron injection and transport layer means a layer that simultaneously injects and transports electrons. The hole injection layer 301 and/or the hole transport layer 401 of FIG. 1 may be formed using a coating composition including the compound of Formula 1 described above.

1 illustrates an organic light emitting device, but 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 using materials and methods known in the art, except that at least one layer of the organic material layer is formed using a coating composition including the compound of Formula 1 above.

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking 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, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. and an organic material layer including at least one layer of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, an electron transport layer, a hole injection and transport layer, and an electron injection and transport layer thereon. It can be prepared by depositing a material that can be used as a cathode on it. In addition to this 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.

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

Specifically, in one embodiment of the present specification, the steps of preparing a first electrode; forming one or more organic material layers on the first electrode; and forming a second electrode on the one or more organic material layers, wherein the forming of the one or more organic material layers includes forming one or more organic material layers using the coating composition.

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

In another embodiment, the step of forming one or more organic material layers using the coating composition uses a printing method.

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

Since the coating composition according to an exemplary embodiment of the present specification is suitable for a solution process due to its structural characteristics, it can be formed by a printing method, thereby having an economical effect in terms of time and cost when manufacturing a device.

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

In an exemplary embodiment of the present specification, the heat treatment may be performed through heat treatment, and the heat treatment temperature in the heat treatment step may be 85° C. to 250° C., and 100° C. to 250° C. according to an exemplary embodiment, In another exemplary embodiment, it may be 150 °C to 250 °C.

In another exemplary embodiment, the heat treatment time in the heat treatment step is 1 minute to 2 hours, according to an exemplary embodiment may be 1 minute to 1 hour, in another exemplary embodiment, 30 minutes to It can be 1 hour.

When the step of forming one or more organic material layers formed by using the coating composition includes the heat treatment or light treatment step, a plurality of the compounds included in the coating composition form cross-linking to provide an organic material layer including a thinned structure. can In this case, when another layer is laminated on the surface of the organic material layer formed by using the coating composition, it can be prevented from being dissolved, morphologically affected, or decomposed by a solvent.

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

As the anode material, a material having a large work function is generally 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, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : a combination of a metal such as Sb and an oxide; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

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

The hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and is produced in the light emitting layer A compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include the compound of Formula 1, metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, and quinacridone-based organic material. , perylene-based organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or hole injection layer to the light emitting layer and has high hole mobility. material is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

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

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining 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 compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

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

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene, and the like, having an arylamino group. As the styrylamine compound, a substituted or unsubstituted It is a compound in which at least one arylvinyl group is substituted in the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. Do. Specific examples include 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 may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically, they are cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.

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

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

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

The hole blocking layer is a layer that blocks the 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 complex, and the like, but is not limited thereto.

The electron blocking layer is a layer that blocks electrons from reaching the anode, and a material known in the art may be used.

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

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

< Synthesis example >

1. Synthesis of intermediates

(1) Synthesis of intermediate P1

Put 3-Bromoiodobenzene (50.0g, 177.4mmol), Phenyl boronic acid (22.7g, 186.3mmol), 1,4-dioxane 150mL in a 500mL round-bottom flask After heating and stirring. After confirming the complete solution, Pd(PPh ₃ ) ₄ (3.0 g 2.7 mmol) was added, followed by K ₂ CO ₃ (29.4 g 212.9 mmol) dissolved in 50 mL of distilled water and an aqueous solution was added, followed by stirring in a 120 ° C bath for 12 hours or more. and refluxed and cooled to room temperature. The organic layer was extracted with ethyl acetate (EA), dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the material was separated through column chromatography (MC/Hexane).

In the case of the reaction, the purity is on the low side at 93%, but the remaining 7% is all iodobiphenyl. The next reaction was carried out without ¹ H NMR of P1: δ 7.75 - 7.67 (m, 3H), 7.49 - 7.41 (m, 6H)

(2) Synthesis of intermediate P2

Intermediate P1 (10.0g, 43.1mmol), 4-Aminophenylboronic acid pinacol ester (11.3g 51.7mmol), and 1,4-dioxane 100mL were added to a 500mL round-bottom flask Heat and stir. When the complete state is confirmed, Pd(PPh ₃ ) ₄ (1.0g, 0.9mmol) is added, followed by adding an aqueous solution in which K ₂ CO ₃ (7.0g, 51.7mmol) is dissolved in 20mL of distilled water, and in a 120℃ bath for 12 hours or more It was stirred and refluxed and cooled to room temperature. The organic layer was extracted with ethyl acetate (EA), dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the material was separated through column chromatography (MC/Hexane).

In the case of the substance, the target pit is measured under High Pressure Liquid Chromatography (HPLC) with a method of A solvent = tetrahydrofuran (THF) / acetonitrile (CAN) 50 : 50, B solvent = distilled water, A : B = 50 : 50 ratio. (target pea) was detected by dividing it into 1.84 min and 1.98 min, but it was confirmed that it was a single substance through thin layer chromatography (TLC) and NMR analysis. ¹ H NMR of P2: δ 7.81 - 7.71 (m, 3H), 7.63 - 7.49 (m, 6H), 7.46 - 7.43 (t, 1H), 6.62 - 6.60 (d, 3H), 5.24 (s, 2H)

(3) Synthesis of intermediate P3

Put 4-Bromoiodobenzene (50.0g, 177.4mmol), Phenyl boronic acid (22.7g, 186.3mmol), 1,4-dioxane 150mL in a 500mL round bottom flask After heating and stirring. Thereafter, the material was separated by purification in the same manner as in P1. ¹ H NMR of P3: δ 7.75 (d, 2H), 7.65 (s, 4H), 7.49 - 7.41 (m, 3H)

(4) Synthesis of intermediate P4

Intermediate P3 (10.0g, 43.1mmol), 4-Aminophenylboronic acid pinacol ester (11.3g 51.7mmol), and 1,4-dioxane 100mL were added to a 500mL round-bottom flask Heat and stir. Thereafter, the material was separated by purification in the same manner as in P2. ¹ H NMR of P4: δ 7.75 (d, 1H), 7.49 - 7.41 (m, 5H), 7.25 (s, 4H), 6.58 (d, 2H), 5.24 (s, 2H)

(5) Synthesis of intermediate P5

Put 2-Bromoiodobenzene (50.0g, 177.4mmol), Phenyl boronic acid (22.7g, 186.3mmol), 1,4-dioxane 150mL into a 500mL round-bottom flask After heating and stirring. Thereafter, the material was separated by purification in the same manner as in P1. ¹ H NMR of P5: δ 7.73 - 7.66 (m, 2H), 7.52 - 7.41 (m, 7H)

(6) Synthesis of intermediate P6

Intermediate P5 (10.0g, 43.1mmol), 4-aminophenylboronic acid pinacol ester (11.3g 51.7mmol), and 1,4-dioxane 100mL were added to a 500mL round-bottom flask Heat and stir. Thereafter, the material was separated by purification in the same manner as in P2. ¹ H NMR of P6: δ 7.96 (d, 2H), 7.79 (d, 2H), 7.60 (d, 2H), 7.46 - 7.41 (m, 3H), 6.58 (d, 2H), 5.24 (s, 2H)

2. Synthesis of compound A

In a 250mL round-bottom flask, Intermediate P2 (2.0g, 8.2mmol) and curing group-binding intermediate (9.8g, 17.2mmol), NaOtBu (1.73g, 18.0mmol) and Pd[P(t-Bu) ₃ ] ₂ (130mg, 0.2 mmol) and then suspended in toluene (50 mL). The input mixture was stirred and refluxed for 2 hours, and then cooled to room temperature. Distilled water was added to the reaction solution to terminate the reaction, and the organic layer was extracted, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the material was separated through column chromatography (dichloromethane (MC)/Hexane) to obtain Compound A. [M+H] ⁺ = 1225

3. Synthesis of compound B

In a 250mL round-bottom flask, intermediate P4 (2.0g, 8.2mmol) and curing group-binding intermediate (9.8g, 17.2mmol), NaOtBu (1.73g, 18.0mmol) and Pd[P(t-Bu) ₃ ] ₂ (130 mg, 0.2 mmol) and then suspended in toluene (50 mL). The input mixture was stirred and refluxed for 2 hours, and then cooled to room temperature. Thereafter, purification was carried out in the same manner as in Compound A to isolate the material to obtain Compound B. [M+H] ⁺ = 1225

4. Synthesis of compound C

In a 250mL round-bottom flask, intermediate P6 (2.0g, 8.2mmol) and curing group-binding intermediate (9.8g, 17.2mmol), NaOtBu (1.73g, 18.0mmol) and Pd[P(t-Bu) ₃ ] ₂ (130 mg, 0.2 mmol) and then suspended in toluene (50 mL). The input mixture was stirred and refluxed for 2 hours, and then cooled to room temperature. Thereafter, purification was carried out in the same manner as in Compound A to isolate the material to obtain Compound C. [M+H] ⁺ = 1225

5. Synthesis of compound D

In a 250mL round-bottom flask, Intermediate P2 (2.0g, 8.2mmol) and the curing group-binding intermediate (7.7g, 17.2mmol), NaOtBu (1.73g, 18.0mmol) and Pd[P(t-Bu) ₃ ] ₂ (130 mg, 0.2 mmol) and then suspended in toluene (50 mL). The input mixture was stirred and refluxed for 2 hours, and then cooled to room temperature. Thereafter, purification was carried out in the same manner as in Compound A to isolate the material to obtain Compound D. [M+H] ⁺ = 985

6. Synthesis of compound E

In a 250mL round-bottom flask, Intermediate P4 (2.0g, 8.2mmol) and curing group-binding intermediate (7.7g, 17.2mmol), NaOtBu (1.73g, 18.0mmol) and Pd[P(t-Bu) ₃ ] ₂ (130mg, 0.2 mmol) and then suspended in toluene (50 mL). The input mixture was stirred and refluxed for 2 hours, and then cooled to room temperature. Then, purification was carried out in the same manner as in Compound A to separate the material to obtain Compound E. [M+H] ⁺ = 985

7. Synthesis of compound F

In a 250mL round-bottom flask, Intermediate P6 (2.0g, 8.2mmol) and curing group-binding intermediate (7.7g, 17.2mmol), NaOtBu (1.73g, 18.0mmol) and Pd[P(t-Bu) ₃ ] ₂ (130 mg, 0.2 mmol) and then suspended in toluene (50 mL). The input mixture was stirred and refluxed for 2 hours, and then cooled to room temperature. Thereafter, purification was carried out in the same manner as in Compound A to isolate the material to obtain Compound F. [M+H] ⁺ = 985

8. Synthesis of compound G

In a 250mL round-bottom flask, arylamine compound (1.4g, 8.2mmol) and curable group binding intermediate (9.8g, 17.2mmol), NaOtBu (1.73g, 18.0mmol) and Pd[P(t-Bu) ₃ ] ₂ (130mg) , 0.2 mmol) was added and then suspended in toluene (50 mL). The input mixture was stirred and refluxed for 2 hours, and then cooled to room temperature. Thereafter, purification was carried out in the same manner as in Compound A to isolate the material to obtain Compound G. [M+H] ⁺ = 1149

9. Synthesis of compound H

In a 250mL round-bottom flask, arylamine compound (1.4g, 8.2mmol) and curable group binding intermediate (7.7g, 17.2mmol), NaOtBu (1.73g, 18.0mmol) and Pd[P(t-Bu) ₃ ] ₂ (130mg) , 0.2 mmol) was added and then suspended in toluene (50 mL). The input mixture was stirred and refluxed for 2 hours, and then cooled to room temperature. Thereafter, purification was carried out in the same manner as in Compound A to separate the material to obtain Compound H. [M+H] ⁺ = 910

< Experimental example >

Example 1.

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,500 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing 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 and dried. After washing the substrate for 5 minutes, the substrate was transported to a glove box.

On the ITO transparent electrode prepared as described above, 1.5 wt% cyclohexanone ink containing compound A prepared in Synthesis Example and the weight ratio of compound P below (compound A:compound P) of 8:2 was spin-coated on the ITO surface, A hole injection layer was formed with a thickness of 30 nm by heat treatment (curing) at 220° C. for 30 minutes. A hole transport layer was formed to a thickness of 40 nm by spin coating 2 wt% toluene ink of the following α-NPD compound on the hole injection layer. Thereafter, after transferring to a vacuum evaporator, the weight ratio (ADN:DPAVBi) of the following ADN compound to the following DPAVBi compound was 20:1 on the hole transport layer, and vacuum deposition was performed to a thickness of 20 nm to form a light emitting layer. On the light emitting layer, the following BCP compound was vacuum-deposited to a thickness of 35 nm to form an electron injection and transport layer. A cathode was formed by sequentially depositing LiF to a thickness of 1 nm and aluminum to a thickness of 100 nm on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 2×10 ^-7 to 5×10 ^-6 torr was maintained.

Example 2.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound B was used instead of Compound A in Example 1.

Example 3.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound C was used instead of Compound A in Example 1.

Example 4.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound D was used instead of Compound A in Example 1.

Example 5.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound E was used instead of Compound A in Example 1.

Example 6.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound F was used instead of Compound A in Example 1.

Comparative Example 1.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound G was used instead of Compound A in Example 1.

Comparative Example 2.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound H was used instead of Compound A in Example 1.

Comparative Example 3.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that a compound having the following structure was used instead of Compound A in Example 1.

Driving voltage, current efficiency, quantum efficiency (QE) and luminance values were measured for the organic light emitting devices prepared in Examples 1 to 6 and Comparative Examples 1 to 3 at a current density of 10 mA/cm ² , and the luminance was the initial luminance ( 1000 nit) compared to 95% of the time (T95) was measured. The results are shown in Table 1 below.

Experimental example Driving voltage (V) Efficiency (Cd/A) QE (%) Luminance (cd/m ² ) Lifetime (hr, T95) Example 1 4.75 5.26 6.54 525.97 152 Example 2 4.84 5.13 6.44 513.82 94 Example 3 4.66 5.22 6.19 508.26 101 Example 4 4.62 5.04 6.18 503.65 149 Example 5 4.75 4.99 6.21 521.32 89 Example 6 4.71 5.09 6.32 515.73 92 Comparative Example 1 5.74 4.67 6.55 490.13 42 Comparative Example 2 5.92 4.71 6.36 481.95 38 Comparative Example 3 6.87 4.84 6.69 483.65 12

From the results of Table 1, the devices of Examples 1 to 6 including the organic material layer formed using the coating composition containing the compound of the present application have lower driving voltage than the devices of Comparative Examples 1 to 3, current efficiency and quantum efficiency, In particular, it can be seen that the lifetime value is significantly improved. Specifically, Examples 1 to 6 using the present compound have a structure similar to that of the present compound, but have superior device properties than Comparative Examples 1 to 3 using a compound having three or less consecutive benzene rings included in the aryl group. can be checked

101: substrate
201: first electrode
301: hole injection layer
401: hole transport layer
501: light emitting layer
601: electron injection and transport layer
701: second electrode

Claims (11)

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

In Formula 1,
L1 to L4 are the same as or different from each other, and are each independently a substituted or unsubstituted arylene group,
Y1 to Y4 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted an aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group or a curable group, and at least one of Y1 to Y4 is a curable group,
R1 to R5 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted an aryloxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
n1 and n4 are each an integer from 0 to 4,
n2 and n3 are each an integer from 0 to 3,
n5 is an integer from 0 to 5,
When each of n1 to n5 is 2 or more, the substituents in the parentheses of 2 or more are the same as or different from each other,
m is an integer from 3 to 10; The method according to claim 1,
Formula 1 is a compound represented by Formula 2 below:
[Formula 2]

In Formula 2,
The definitions of L1 to L4, Y1 to Y4, R1 to R4 and n1 to n4 are the same as in Formula 1,
R11 to R13 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted an aryloxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
n11 and n12 are each an integer from 0 to 4,
n13 is an integer from 0 to 5,
When each of n11 to n13 is two or more, the substituents in the two or more parentheses are the same as or different from each other. The method according to claim 1,
wherein L1 to L4 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenylene group. The method according to claim 1,
Formula 1 is a compound represented by Formula 3 below:
[Formula 3]

In Formula 3,
Y1 to Y4, R1 to R5, n1 to n5 and m have the same definitions as in Formula 1,
R21 to R24 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted an aryloxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
n21 to n24 are each an integer of 0 to 4,
When each of n21 to n24 is 2 or more, the substituents in the two or more parentheses are the same as or different from each other. The method according to claim 1,
Formula 1 is a compound represented by the following Formula 3-1:
[Formula 3-1]

In Formula 3-1,
Y1 to Y4, R1 to R4 and n1 to n4 have the same definitions as in Formula 1,
R11 to R13 and R21 to R24 are the same as or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, A substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
n11, n12 and n21 to n24 are each an integer of 0 to 4,
n13 is an integer from 0 to 5,
When n11 to n13 and n21 to n24 are 2 or more, respectively, the substituents in the two or more parentheses are the same as or different from each other. The method according to claim 1,
The compound of Formula 1 is represented by any one of the following compounds:

. A coating composition comprising a compound according to any one of claims 1 to 6. a first electrode;
a second electrode; and
At least one organic material layer provided between the first electrode and the second electrode,
At least one of the at least one organic material layer is an organic light emitting device comprising the coating composition of claim 7 or a cured product thereof. 9. The method of claim 8,
The organic material layer comprising the coating composition or a cured product thereof is an organic light emitting device that is a hole transport layer or a hole injection layer. preparing a first electrode;
forming one or more organic material layers on the first electrode; and
Comprising the step of forming a second electrode on the at least one organic material layer,
The method of manufacturing an organic light emitting device, wherein the forming of the at least one organic material layer comprises the step of forming at least one organic material layer using the coating composition of claim 7 . 11. The method of claim 10,
The step of forming an organic material layer using the coating composition is
coating the coating composition on the first electrode or one or more organic material layers; and
Method of manufacturing an organic light-emitting device comprising the step of heat-treating or light-treating the coated coating composition.

Images