KR102768898B1 - Compound, coating compositions comprising the same, and organic light emitting device using the same - Google Patents

Abstract

The present specification provides a compound represented by chemical formula 1, a coating composition comprising the same, and an organic light-emitting device using the same.

Description

COMPOUND, COATING COMPOSITIONS COMPRISING THE SAME, AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME

The present specification relates to a compound, a coating composition comprising the same, and an organic light-emitting device formed using the same.

Organic luminescence is an example of an electric current being converted into visible light by an internal process of a specific organic molecule. The principle of the organic luminescence is as follows. When an organic layer is positioned between an anode and a cathode and a current is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. The electrons and holes injected into the organic layer recombine to form excitons, and when these excitons fall back to the ground state, light is emitted. An organic electroluminescent device utilizing this principle can generally be composed of an organic layer including a cathode and an anode and an organic layer positioned therebetween, such as a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an electron injection layer.

Most of the materials used in organic light-emitting devices are pure organic substances or complex compounds formed by complexing organic substances with metals, and can be classified into hole injection materials, hole transport materials, luminescent materials, electron transport materials, and electron injecting materials depending on the purpose. Here, organic substances with p-type properties, that is, organic substances that are easily oxidized and have an electrochemically stable state when oxidized, are mainly used as hole injection materials or hole transport materials. On the other hand, organic substances with n-type properties, that is, organic substances that are easily reduced and have an electrochemically stable state when reduced, are mainly used as electron injection materials or electron transport materials. As luminescent materials, a material that has both p-type and n-type properties, that is, a material that is stable in both oxidized and reduced states, and a material with high luminescent efficiency that converts excitons into light when formed is preferable.

In addition to those mentioned above, it is desirable for materials used in organic light-emitting devices to have the following additional properties.

First, it is desirable that the material used in the organic light-emitting device have excellent thermal stability. This is because Joule heating occurs due to the movement of charges within the organic light-emitting device. NPB (N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), which is currently mainly used as a hole transport layer material, has a glass transition temperature of less than 100℃, and therefore has a problem in that it is difficult to use in organic light-emitting devices that require high current.

Second, in order to obtain a high-efficiency organic light-emitting device that can be driven at low voltage, the holes or electrons injected into the organic light-emitting device must be smoothly transferred to the light-emitting layer, while the injected holes and electrons must be prevented from escaping out of the light-emitting layer. To this end, the material used in the organic light-emitting device must have an appropriate band gap and HOMO (Highest Occupied Molecular Orbital) or LUMO (Lowest Unoccupied Molecular Orbital) energy level. In the case of PEDOT:PSS (Poly(3,4-ethylenediocythiophene) doped:poly(styrenesulfonic acid)), which is currently used as a hole transport material in organic light-emitting devices manufactured by the solution coating method, the LUMO energy level is lower than that of the organic material used as the light-emitting layer material, making it difficult to manufacture high-efficiency, long-life organic light-emitting devices.

In addition, the material used in the organic light-emitting device must have excellent chemical stability, charge mobility, and interface characteristics with the electrode or adjacent layer. In other words, the material used in the organic light-emitting device must be less deformed by moisture or oxygen. In addition, it must have appropriate hole or electron mobility so that the density of holes and electrons in the light-emitting layer of the organic light-emitting device is balanced to maximize exciton formation. In addition, it must be able to improve the interface with the electrode including a metal or metal oxide for the stability of the device.

In addition to those mentioned above, materials used in organic light-emitting devices for solution processes must additionally have the following properties.

First, a storable, homogeneous solution must be formed. In the case of commercialized deposition process materials, they have good crystallinity and do not dissolve well in the solution, or even if a solution is formed, crystals are easily formed, so the concentration gradient of the solution changes depending on the storage period, or there is a high possibility of forming a defective element.

Second, the layers in which the solution process is performed must have solvent and material resistance with respect to other layers. To this end, a material that can form a self-cross-linked polymer on the substrate through heat treatment or UV (ultraviolet) irradiation after solution application by introducing a curing agent, such as VNPB (N4,N4'-di(naphthalen-1-yl)-N4,N4'-bis(4-vinylphenyl)biphenyl-4,4'-diamine), or a material that can form a polymer sufficiently resistant to the next process is preferable. A material that can have solvent resistance on its own, such as HATCN (Hexaazatriphenylenehexacarbonitrile), is also preferable.

Therefore, in the field of party technology, there is a demand for the development of organic materials having the above requirements.

Korean Patent Publication No. 10-2004-0028954

The present specification provides a compound, a coating composition comprising the same, and an organic light-emitting device formed using the same.

One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[Chemical Formula 1]

In the above chemical formula 1,

A1 to A6 are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted heterocycle,

R1 to R4 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

Ar1 and Ar2 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

a and c are integers from 1 to 4, respectively.

b and d are each integers from 1 to 3,

When the above a is 2 or more, the above 2 or more R1 are the same or different from each other,

When the above b is 2 or more, the above 2 or more R2 are the same or different from each other,

When the above c is 2 or more, the above 2 or more R3 are the same or different from each other,

When the above d is 2 or more, the two or more R4s are the same or different from each other.

Another embodiment of the present disclosure provides a coating composition comprising the compound.

Another embodiment of the present disclosure comprises: a first electrode;

A second electrode provided opposite to the first electrode;

Comprising at least one organic layer provided between the first electrode and the second electrode,

An organic light-emitting device is provided, wherein at least one of the organic layers comprises the compound.

Another embodiment of the present specification comprises the steps of preparing a first electrode;

A step of forming one or more organic layers including a light-emitting layer on the first electrode; and

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

The method for manufacturing an organic light-emitting device is provided, wherein the step of forming the organic layer includes the step of forming the light-emitting layer using the coating composition.

A compound according to one embodiment of the present specification has a short conjugation length and a high molecular weight, thereby improving inkjet characteristics. Accordingly, a solution process is possible when applied to a device.

In addition, a compound according to one embodiment of the present specification can be used as a material of an organic layer of an organic light-emitting device, thereby improving the life characteristics of the device.

Figures 1 and 2 are diagrams illustrating the structure of an organic light-emitting device according to one embodiment of the present specification.

Below, the present specification is described in more detail.

The present specification provides a compound represented by the following chemical formula 1.

[Chemical Formula 1]

In the above chemical formula 1,

A1 to A6 are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted heterocycle,

R1 to R4 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

Ar1 and Ar2 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

a and c are integers from 1 to 4, respectively.

b and d are each integers from 1 to 3,

When the above a is 2 or more, the above 2 or more R1 are the same or different from each other,

When the above b is 2 or more, the above 2 or more R2 are the same or different from each other,

When the above c is 2 or more, the above 2 or more R3 are the same or different from each other,

When the above d is 2 or more, the two or more R4s are the same or different from each other.

The compound of the above chemical formula 1 has a short conjugation length and a high molecular weight, thereby improving inkjet characteristics. Accordingly, a solution process is possible when applied to a device.

In addition, the compound of the above chemical formula 1 has a structure of a dimer including two heterocycles including boron, and is more chemically and structurally stable than a compound having a structure including one heterocycle including boron. In addition, the compound of the above chemical formula 1 has a high glass transition temperature (Tg), and therefore has excellent thermal stability. Therefore, the compound of the above chemical formula 1 exhibits an effect of improving the lifespan when applied to an organic light-emitting device.

When it is said in this specification that an element is located "on" another element, this includes not only cases where an element is in contact with another element, but also cases where another element exists between the two elements.

When it is said in this specification that a part "includes" a certain component, this does not exclude other components, but rather may include other components, unless otherwise specifically stated.

Examples of substituents in this specification are described below, but are not limited thereto.

The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited to the position at which the hydrogen atom is replaced, i.e., a position at which the substituent can be replaced, and when two or more are substituted, the two or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group (-CN); a silyl group; a boron group; a nitrile group; a nitro group; an imide group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryloxy group; an amine group; an aryl group; and a heterocyclic group, or substituted with a substituent in which two or more substituents are connected among the above-mentioned substituents, or has no substituents. For example, "a substituent connected with two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent in which two phenyl groups are connected.

Examples of the above substituents are described below, but are not limited thereto.

In this specification, examples of halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

In the present specification, the amide group may have the nitrogen of the amide group substituted with hydrogen, a straight-chain, branched-chain or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound having the following structural formula, but is not limited thereto.

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 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and the like.

In the present specification, the carbon number of the cycloalkyl group is not particularly limited, but is preferably 3 to 60. According to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. Specific examples of the cycloalkyl group include, but are not limited to, 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, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, and the like.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples of the alkenyl group include, but are not limited to, 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, and styrenyl.

In this specification, the number of carbon atoms in the alkynyl group is not particularly limited, but is preferably 2 to 30.

In the present specification, the amine group may be selected from the group consisting of -NH ₂ ; an alkylamine group; an arylalkylamine group; an arylamine group; an arylheteroarylamine group; an alkylheteroarylamine group, and a heteroarylamine group, but is not limited thereto. The number of carbon atoms in the amine group is not particularly limited, but is preferably 1 to 60.

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

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

When the above fluorenyl group is substituted, , Spirofluorenyl group of the back, (9,9-dimethylfluorenyl group), and (9,9-diphenylfluorenyl group), and the structure may be substituted with an additional substituent. However, the structure of the substituted fluorenyl group is not limited thereto.

In the present specification, the aromatic hydrocarbon ring may be monocyclic or polycyclic, and may be selected from among the examples of the above aryl group, excluding those that are monovalent. For example, it may be a phenyl group having two or more valences; or a naphthyl group having two or more valences, but is not limited thereto.

In the present specification, a heterocyclic group includes one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably 2 to 30 carbon atoms. In one embodiment of the present specification, the heterocyclic group may be monocyclic or polycyclic. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine, phenanthroline, isoxazole group, thiadiazole group, Examples include, but are not limited to, phenothiazine groups and dibenzofuran groups.

In the present specification, the heterocycle may be monocyclic or polycyclic, and may be selected from among the examples of the above heterocyclic groups, excluding those that are monovalent. For example, it may be a carbazole group having a valence of two or more; a dibenzofuran group having a valence of two or more; or a dibenzothiophene group having a valence of two or more; but is not limited thereto.

In the present specification, the alkylamine group has no particular limitation on the number of carbon atoms, but may have 1 to 40 carbon atoms, and in one embodiment, may have 1 to 20 carbon atoms. Specific examples of the alkylamine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, etc.

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

Specific examples of arylamine groups include, but are not limited to, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a biphenylphenylamine group, a dibiphenylamine group, and a fluorenylphenylamine group.

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

In the present specification, the heteroaryl group may be selected from among the examples of the above heterocyclic groups, except that it is aromatic, but is not limited thereto.

In this specification, an arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group.

In this specification, an arylalkylamine group means an amine group substituted with an aryl group and an alkyl group.

In this specification, an alkylheteroarylamine group means an amine group substituted with an alkyl group and a heteroaryl group.

In the present specification, the aryl group in the aryloxy group is the same as the examples of the aryl group described above. Specifically, the aryloxy group includes, but is not limited to, a phenoxy group, benzyloxy, p-methylbenzyloxy, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like.

In the present specification, the aromatic hydrocarbon rings and heterocycles located at A1 to A6 are excluded from being monovalent, and may be, for example, a divalent or higher aryl group or a divalent or higher heterocyclic group.

In one embodiment of the present specification, A1 to A6 are the same as or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring.

In one embodiment of the present specification, A1 to A6 are the same as or different from each other, and are each independently a substituted or unsubstituted divalent or higher aryl group.

In one embodiment of the present specification, A1 to A6 are the same as or different from each other, and are each independently a substituted or unsubstituted divalent or higher phenyl group; or a substituted or unsubstituted divalent or higher naphthyl group.

In one embodiment of the present specification, A1 and A4 are the same as or different from each other, and are each independently a substituted or unsubstituted trivalent aromatic hydrocarbon ring.

In one embodiment of the present specification, A1 and A4 are the same as or different from each other, and each independently represents a substituted or unsubstituted trivalent phenyl group; or a trivalent naphthyl group.

In one embodiment of the present specification, A2, A3, A5 and A6 are the same as or different from each other, and are each independently a substituted or unsubstituted divalent aromatic hydrocarbon ring.

In one embodiment of the present specification, A2, A3, A5 and A6 are the same as or different from each other, and each independently represents a substituted or unsubstituted divalent phenyl group; or a divalent naphthyl group.

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

[Chemical Formula 1-1]

In the above chemical formula 1-1,

R1 to R4, a, b, c, d, Ar1 and Ar2 are the same as defined in chemical formula 1,

R11 to R32 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; an amide 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 alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and adjacent groups may be bonded to each other to form a ring.

In this specification, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent stereostructurally closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, in a ring formed by bonding adjacent groups to each other, “ring” means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or a condensed ring of aromatic and aliphatic groups, and may be selected from among the examples of the cycloalkyl group or aryl group, excluding those that are monovalent.

In one embodiment of the present specification, R16 and R17 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.

In one embodiment of the present specification, R29 and R30 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.

In one embodiment of the present specification, R15 and R16 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.

In one embodiment of the present specification, R30 and R31 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.

In one embodiment of the present specification, the chemical formula 1 is represented by one of the following chemical formulas 1-2 to 1-4.

[Chemical Formula 1-2]

[Chemical Formula 1-3]

[Chemical Formula 1-4]

In the above chemical formulas 1-2 to 1-4,

R1 to R4, a, b, c, d, Ar1 and Ar2 are the same as defined in chemical formula 1,

R11 to R36 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; an amide 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 alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

e, f, g and h are integers from 1 to 4, respectively.

When the above e is 2 or more, the above 2 or more R33s are the same or different from each other,

When the above f is 2 or more, the above 2 or more R34s are the same or different from each other,

When the above g is 2 or more, the above 2 or more R35s are the same or different from each other,

When the above h is 2 or more, the two or more R36 are the same or different.

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

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

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group substituted or unsubstituted with an alkyl group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted with an alkyl group.

In one embodiment of the present specification, R11 to R32 are the same as or different from each other, and each independently represent hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted amine group.

In one embodiment of the present specification, R11 to R32 are the same as or different from each other, and each independently represent hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted diarylamine group.

In one embodiment of the present specification, R11 to R32 are the same as or different from each other, and each independently represent hydrogen; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted diarylamine group.

In one embodiment of the present specification, R11 to R32 are the same as or different from each other, and are each independently hydrogen; a linear or branched, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a diarylamine group unsubstituted or substituted with an alkyl group.

In one embodiment of the present specification, R11 to R32 are the same as or different from each other, and are each independently hydrogen; a methyl group; a tert-butyl group; or a diphenylamine group substituted or unsubstituted with a tert-butyl group.

In one embodiment of the present specification, the compound is represented by one of the following structures.

In one embodiment of the present specification, the molecular weight of the compound is 1,000 g/mol to 10,000 g/mol. Specifically, the molecular weight of the compound is 1,000 g/mol to 2,000 g/mol. Preferably, the molecular weight of the compound is 1,000 g/mol to 1,500 g/mol.

The core structure of chemical formula 1 according to one embodiment of the present specification can be manufactured as shown in the following reaction formula, and the substituents can be combined by a method known in the art, and the type, position or number of the substituents can be changed according to a technique known in the art.

<Reaction formula>

In the above reaction formula, A1 to A6, Ar1 and Ar2 are the same as defined in chemical formula 1.

In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In addition, in the present invention, HOMO and LUMO energy levels of the compound can also be controlled by introducing various substituents into the core structure having the structure described above.

In addition, by introducing various substituents into the core structure having the structure as described above, it is possible to synthesize a compound having the unique characteristics of the introduced substituent. For example, by introducing a substituent mainly used in hole injection layer materials, hole transport materials, light-emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the core structure, it is possible to synthesize a material satisfying the conditions required for each organic layer.

One embodiment of the present disclosure provides a coating composition comprising the compound described above.

In one embodiment of the present specification, the coating composition further comprises a solvent. In one embodiment of the present specification, the coating composition comprises the compound and a solvent.

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

In one embodiment of the present specification, it is preferable that the solvent does not dissolve the material applied to the lower layer.

For example, when the coating composition is applied to a light-emitting layer, there is an advantage in that the light-emitting layer can be introduced through a solution process by using a solvent that does not dissolve the material of the lower layer (hole transport layer, hole injection layer, first electrode, etc.).

In one embodiment of the present specification, the solvent is, for example, a chlorine solvent such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene; an ether solvent such as tetrahydrofuran, dioxane; an aromatic hydrocarbon solvent such as toluene, xylene, trimethylbenzene, mesitylene; a ketone solvent such as acetone, methyl ethyl ketone, cyclohexanone; an ester solvent such as ethyl acetate, butyl acetate, ethyl cellosolve acetate; a polyhydric alcohol and derivatives thereof 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; Examples of the solvent include alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents such as methyl benzoate, butyl benzoate, and 3-phenoxy benzoate; and tetralin. However, any solvent capable of dissolving or dispersing the compound according to one embodiment of the present specification may be used, and is not limited thereto.

In one embodiment of the present specification, the solvent may be used alone or as a mixture of two or more solvents.

In one embodiment of the present specification, the boiling point of the solvent is preferably 40°C to 350°C, more preferably 80°C to 330°C, but is not limited thereto.

In one embodiment of the present specification, the viscosity of the single or mixed solvent is preferably 1 CP to 10 CP, more preferably 3 CP to 8 CP, but is not limited thereto.

In one embodiment of the present specification, the concentration of the compound in the coating composition is preferably 0.1 wt/v% to 20 wt/v%, more preferably 0.5 wt/v% to 10 wt/v%, but is not limited thereto.

One embodiment of the present specification comprises: a first electrode;

A second electrode provided opposite to the first electrode;

Comprising at least one organic layer provided between the first electrode and the second electrode,

An organic light-emitting device is provided, wherein at least one of the organic layers comprises the compound.

In one embodiment of the present specification, the thickness of the organic layer including the compound is 1 Å to 500 Å.

The organic layer of the organic light-emitting device of the present invention may be formed as a single-layer structure, but may be formed as a multilayer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including, as organic layers, a hole injection layer, a hole transport layer, a layer that simultaneously injects holes and transports holes, a light-emitting layer, an electron transport layer, an electron injection layer, etc. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers or a larger number of organic layers.

In one embodiment of the present specification, the organic layer includes at least one layer among an electron transport layer, an electron injection layer, and a layer that simultaneously injects electrons and transports electrons. At least one layer among the layers may include the compound.

In one embodiment of the present specification, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound.

In one embodiment of the present specification, the organic layer includes at least one layer among a hole injection layer, a hole transport layer, and a layer that simultaneously injects holes and transports holes, and at least one layer among the layers may include the compound.

In one embodiment of the present specification, the organic layer includes a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include the compound.

In one embodiment of the present specification, the organic layer containing the compound is a light-emitting layer.

In one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the dopant includes the compound.

In one embodiment of the present specification, the host comprises a compound represented by the following chemical formula 5.

[Chemical Formula 5]

In the above chemical formula 5,

Ar11 and Ar12 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently represents a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Ar11 and Ar12 are each a naphthyl group.

In one embodiment of the present specification, the light-emitting layer includes a compound represented by the chemical formula 1 as a dopant and a compound represented by the chemical formula 5 as a host.

In one embodiment of the present specification, the weight ratio of the host and the dopant is 50:50 to 99:1. In one embodiment of the present specification, the light-emitting layer contains the compound represented by the chemical formula 5 and the compound represented by the chemical formula 1 in a weight ratio of 50:50 to 99:1.

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

In another embodiment, the first electrode is a cathode and the second electrode is an anode.

The organic light-emitting device of the present invention can be laminated in a structure as shown in the following example.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

(18) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/hole blocking layer/electron injection layer and transport layer/cathode

The structure of the organic light-emitting device of the present invention may have a structure as shown in Fig. 1, but is not limited thereto.

Figure 1 illustrates the structure of an organic light-emitting device in which a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4) are sequentially laminated. In this structure, the compound may be included in the light-emitting layer (3).

FIG. 2 illustrates the structure of an organic light-emitting device comprising a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (7), an electron transport layer (8), and a cathode (4). In this structure, the compound may be included in the hole injection layer (5), the hole transport layer (6), the light-emitting layer (7), or the electron transport layer (8).

The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.

For example, the organic light-emitting device according to the present invention can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and then forming an organic layer including at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes, an emission layer, an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons, and then depositing a material that can be used as a cathode thereon. In addition to this method, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

The above compound can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

The above organic layer may have a multilayer structure including a light-emitting layer, but is not limited thereto and may have a single-layer structure. In addition, the organic layer may be manufactured with a smaller number of layers by using various polymer materials and a solvent process other than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

The above anode is an electrode that injects holes, and as the anode material, a material having a high work function is preferably used so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include, but are not limited to, 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); combinations of metals and oxides such as ZnO:Al and SnO ₂ :Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

The above cathode is an electrode that injects electrons, and it is preferable that the cathode material be a material having a low work function so that electrons can be easily injected into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF/Al or LiO ₂ /Al.

The above hole injection layer is a layer that facilitates the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage. 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 layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrine, oligothiophene, arylamine series organic compounds, hexanitrilehexaazatriphenylene series organic compounds, quinacridone series organic compounds, perylene series organic compounds, anthraquinone, and conductive polymers of polyaniline and polythiophene series.

The above hole transport layer can play a role in facilitating the transport of holes. As a hole transport material, a material that can transport holes from the anode or hole injection layer and transfer them to the light-emitting layer, and a material with high mobility for holes is suitable.

In one embodiment of the present specification, a hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and a material known in the art may be used for the hole buffer layer.

In one embodiment of the present specification, an electron suppression layer may be provided between the hole transport layer and the light emitting layer. A material known in the art may be used for the electron suppression layer.

The above-mentioned light-emitting layer can emit red, green or blue, preferably blue, and can be made of a phosphorescent material or fluorescent material. The above-mentioned light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from the hole transport layer and the electron transport layer respectively and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.

In one embodiment of the present specification, the light-emitting layer may further include a host material and a dopant material in addition to the compound of the present invention. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, the condensed aromatic ring derivative may include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene derivatives, fluoranthene derivatives, and the like, and the heterocyclic compound may include, but is not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like.

Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periflanthene, etc. having an arylamino group, and styrylamine compounds are compounds in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, and one 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, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but are not limited thereto. In addition, metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

In one embodiment of the present specification, a hole-suppressing layer may be provided between the electron transport layer and the light-emitting layer, and a material known in the art may be used for the hole-suppressing layer.

The above electron transport layer can play a role in facilitating electron transport. As the electron transport material, a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer is suitable, and a material with high electron mobility is suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq ₃ ; organic radical compounds; and hydroxyflavone-metal complexes.

The above electron injection layer can play a role in facilitating electron injection. As the electron injection material, a compound having the ability to transport electrons, an excellent electron injection effect from the cathode, an excellent electron injection effect for the light-emitting layer or the light-emitting material, preventing excitons generated in the light-emitting layer from moving to the hole injection layer, and excellent thin film forming ability is preferable. Specific examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

As the above metal complex compounds, 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-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

The above hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

A method for manufacturing an organic light-emitting device according to one embodiment of the present specification comprises the steps of: preparing a first electrode;

A step of forming one or more organic layers including a light-emitting layer on the first electrode; and

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

The step of forming the organic layer includes a step of forming the light-emitting layer using the coating composition.

In one embodiment of the present specification, the step of forming a light-emitting layer using the coating composition comprises:

A step of coating the coating composition on the first electrode; and

A step of drying the above-mentioned coated coating composition is included.

In one embodiment of the present specification, the drying step applies temperature conditions and time used in the art. For example, drying may be performed at 80° C. to 200° C. for 1 minute to 2 hours.

One embodiment of the present specification applies a method for manufacturing an organic light-emitting device used in the art, except that the coating composition is used.

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

Hereinafter, in order to specifically explain this specification, examples will be given in detail. However, the embodiments according to this specification may be modified in various different forms, and the scope of this application is not construed as being limited to the embodiments described below. The embodiments of this application are provided to more completely explain this specification to a person having average knowledge in the art.

<Synthetic example>

Synthesis Example 1. Preparation of Compound D-1

(1) Preparation of intermediate compound A-1

1-bromo-2,3-dichlorobenzene (10.0 g, 44.3 mmol, 1.5 eq), diphenylamine (5.0 g, 29.5 mmol, 1.0 eq), bis(tri-tert-butylphosphine)palladium(0) (Pd[P(tBu ₃ )] ₂ ) (0.6 g, 1.2 mmol, 0.04 eq), sodium tert-butoxide (NaOtBu) (8.5 g, 88.4 mmol, 3.0 eq) were placed in a two-neck round bottom flask (two-neck RB) and replaced with a nitrogen atmosphere. 300 mL Toluene (Tol) was added and stirred at 110℃ overnight. After cooling to room temperature, water (H ₂ O) was added and the organic layer was separated. Magnesium sulfate (MgSO ₄ ) was added to remove water, and the filtrate was filtered to remove the solvent. 7.8 g (84%) of intermediate compound A-1 was obtained through dichloromethane/hexane (DCM/Hx) column purification. MS: [M+H] ⁺ = 314

(2) Preparation of intermediate compound B-1

5 g (15.9 mmol, 1.1 eq) of intermediate compound A-1 obtained in (1) of the above Synthetic Example 1, 1.3 mL (14.2 mmol, 1.0 eq) of aniline, 0.3 g (0.6 mmol, 0.04 eq) of Pd[P(tBu ₃ )] ₂ , and 4.2 g (43.7 mmol, 3.1 eq) of NaOtBu were placed in a two-neck RB and replaced with a nitrogen atmosphere. 100 mL of toluene was added and stirred at 110°C overnight. After cooling to room temperature, H ₂ O was added and the organic layer was separated. MgSO ₄ was added to remove water, and the solvent of the filtrate was removed by filtering. 4.5 g (84%) of intermediate compound B-1 was obtained through DCM/Hx column purification. MS: [M+H] ⁺ = 371

(3) Preparation of intermediate compound C-1

4 g (10.8 mmol, 2.1 eq) of intermediate compound B-1 obtained in (2) of the above Synthetic Example 1, 2.3 g (4.9 mmol, 1.0 eq) of 2,2'-dibromo-9,9'-spirobi[fluorine], Pd[P(tBu ₃ )] ₂ 0.1 g (0.2 mmol, 0.04 eq) and NaOtBu 1.4 g (14.6 mmol, 3.0 eq) were placed in a two-neck RB and replaced with a nitrogen atmosphere. 70 mL of toluene was added and stirred at 110°C overnight. After cooling to room temperature, H ₂ O was added and the organic layer was separated. MgSO ₄ was added to remove water, and the solvent of the filtrate was removed by filtering. 3.0 g (59%) of the intermediate compound C-1 was obtained through DCM/Hx column purification. MS: [M+H] ⁺ =1053

(4) Preparation of compound D-1

3.0 g (2.8 mmol, 1.0 eq) of the intermediate compound C-1 obtained in (3) of the above Synthetic Example 1 was dissolved in 100 mL of t-butyl benzene and the atmosphere was replaced with a nitrogen atmosphere. 2.0 mL (3.4 mmol, 1.2 eq) of 1.7 M tert-butyllithium (t-BuLi) was slowly added dropwise at -30°C, the temperature was raised to 65°C and stirred for 3 hours. The temperature was lowered to -30°C again and 0.3 mL (3.2 mmol, 1.1 eq) of boron tribromide (BBr ₃ ) was slowly added dropwise. After stirring at room temperature for 1 hour, 1 mL of N,N-diisopropylethylamine (DIPEA) (5.7 mmol, 2.0 eq) was added at 0°C, stirred at 120°C for 3 hours, and cooled to room temperature. 0.9 g (32%) of compound D-1 was obtained through ethyl acetate/hexane (EA/Hx) column purification. MS: [M+H] ⁺ =1001

Synthesis Example 2. Preparation of Compound D-2

Compound D-2 was obtained in the same manner as in Synthesis Example 1, except that 1-bromo-2,3-dichloro-5-methylbenzene was used instead of 1-bromo-2,3-dichlorobenzene in (1) of Synthesis Example 1. MS: [M+H] ⁺ = 1029

Synthesis Example 3. Preparation of Compound D-3

Compound D-3 was obtained in the same manner as in Synthesis Example 1, except that 1-bromo-2,3-dichloro-5-methylbenzene was used instead of 1-bromo-2,3-dichlorobenzene in (1) of the above Synthesis Example 1, and N1,N2,N3-triphenylbenzene-1,3-diamine was used instead of diphenylamine. MS: [M+H] ⁺ = 1363

Synthesis Example 4. Preparation of Compound D-4

Compound D-4 was obtained in the same manner as in Synthesis Example 1, except that 4-(tert-butyl)-2,6-dimethyl-N-phenylaniline was used instead of diphenylamine in (1) of Synthesis Example 1. MS: [M+H] ⁺ = 1169

<Example>

Example 1. Manufacturing of organic light-emitting device

A glass substrate on which a 500 Å thick ITO (indium tin oxide) film was deposited was placed in distilled water containing a detergent and ultrasonically cleaned. The detergent used was a Fisher Co. product, and the distilled water used was distilled water that had been filtered twice through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After the distilled water washing was complete, ultrasonic cleaning was performed with acetone, distilled water, and isopropyl alcohol solvents, and dried to prepare a cleaned ITO transparent electrode.

A composition containing the following compound Z-1 and the following compound Z-2 in a weight ratio of 8:2 was spin-coated on the ITO transparent electrode, and cured on a hot plate at 220°C for 30 minutes under a nitrogen atmosphere to form a hole injection layer with a thickness of 400 Å.

On the above hole injection layer, a composition in which the compound Z-1 was dissolved in toluene at a weight ratio of 1% was spin-coated and cured on a hot plate at 200°C for 30 minutes to form a hole transport layer with a thickness of 200 Å.

A coating composition containing compound Z-3 and compound D-1 prepared in Synthesis Example 1 dissolved in toluene at a weight ratio of 96:4 and 0.5% was spin-coated on the hole transport layer, and dried on a hot plate at 120° C. for 10 minutes under a nitrogen atmosphere to form a 200 Å thick light-emitting layer.

Afterwards, the organic light-emitting device was fabricated by sequentially depositing the following compounds Z-4 (thickness: 300 Å), LiF (thickness: 10 Å), and Al (thickness: 1,000 Å) in a vacuum deposition device. In the process, the deposition rate of the cathode LiF was maintained at 0.1 Å/sec, the deposition rate of aluminum (Al) was maintained at 2 Å/sec, and the vacuum level during deposition was maintained at 2x10 ^-7 to 5x10 ^-8 torr.

Examples 2 to 4 and Comparative Example 1.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the material described in Table 2 below was used instead of compound D-1 as the light-emitting layer dopant material in Example 1.

Experimental example. Characteristic evaluation of organic light-emitting device

When current was applied to the organic light-emitting devices according to Examples 1 to 3 and Comparative Example 1, the driving voltage, current efficiency, power efficiency, and lifespan (T90) were measured. The results are shown in Table 1 below.

The above lifespan (T90) refers to the time required for the luminance to decrease to 90% of the initial luminance.

luminescent layer
Dopant Driving voltage
(V@10mA/ ^cm2 ) Current efficiency
(cd/A @10mA/cm ² ) T90 (hr)
@20mA/cm ² Example 1 Compound D-1 4.33 5.54 72 Example 2 Compound D-2 4.43 5.61 67 Example 3 Compound D-3 4.29 5.93 71 Comparative Example 1 Compound BD-1 4.51 5.65 38

From the above Table 1, it can be confirmed that when the compound according to the present invention is used as a dopant in the light-emitting layer, the lifespan of the device is superior compared to when it is not used.

1: Substrate
2: Bipolar
3: Emissive layer
4: Negative
5: Hole injection layer
6: Hole transport layer
7: Emissive layer
8: Electron transport layer

Claims (12)

A compound represented by any one of the following chemical formulas 1-2 to 1-4:
[Chemical Formula 1-2]

[Chemical Formula 1-3]

[Chemical Formula 1-4]

In the above chemical formulas 1-2 to 1-4,
R1 to R4 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.
Ar1 and Ar2 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,
R11 to R36 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; an amide 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 alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,
a, c, e, f, g and h are integers from 1 to 4, respectively.
b and d are each integers from 1 to 3,
When the above a is 2 or more, the above 2 or more R1 are the same or different from each other,
When the above b is 2 or more, the above 2 or more R2 are the same or different from each other,
When the above c is 2 or more, the above 2 or more R3 are the same or different from each other,
When the above d is 2 or more, the two or more R4s are the same or different from each other.
When the above e is 2 or more, the above 2 or more R33s are the same or different from each other,
When the above f is 2 or more, the above 2 or more R34s are the same or different from each other,
When the above g is 2 or more, the above 2 or more R35s are the same or different from each other,
When the above h is 2 or more, the two or more R36 are the same or different. delete delete In claim 1,
The above compound is a compound represented by one of the following structures:

A coating composition comprising a compound according to claim 1 or 4. In claim 5,
A coating composition further comprising a solvent. First electrode;
A second electrode provided opposite to the first electrode; and
Comprising at least one organic layer provided between the first electrode and the second electrode,
An organic light-emitting device, wherein at least one of the organic layers comprises a compound according to claim 1 or 4. In claim 7,
An organic light-emitting device, wherein the organic layer containing the above compound is a light-emitting layer. In claim 8,
The above-mentioned light-emitting layer comprises a host and a dopant,
An organic light-emitting device wherein the dopant comprises the compound. In claim 9,
The above host is an organic light-emitting device comprising a compound represented by the following chemical formula 5:
[Chemical Formula 5]

In the above chemical formula 5,
Ar11 and Ar12 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group. Step 1: Preparing the first electrode;
A step of forming one or more organic layers including a light-emitting layer on the first electrode; and
Comprising a step of forming a second electrode on the organic layer,
A method for manufacturing an organic light-emitting device, wherein the step of forming the organic layer includes the step of forming the light-emitting layer using the coating composition of claim 5. In claim 11,
The step of forming a light-emitting layer using the above coating composition is
A step of coating the coating composition on the first electrode; and
A method for manufacturing an organic light-emitting device, comprising the step of drying the coated coating composition.

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