KR102128152B1 - Compound, coating composition comprising the same, organic light emitting device using the same and method of manufacturing the same - Google Patents

Abstract

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

Description

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

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

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

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

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

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

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

Korea Patent Publication No. 2012-0112277

An object of the present specification is to provide a compound usable in an organic light emitting device for solution processing, a coating composition comprising the compound, an organic light emitting device including the coating composition, and a method for manufacturing the organic light emitting device.

The present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1,

X1 and X2 are the same as or different from each other, and each independently represented by the following Formula 1-1 or Formula 1-2,

A is represented by the following formula 1-3,

B is represented by the following formula 1-4,

a and b are each an integer of 1 or more,

c is an integer greater than or equal to 0,

When c is 0, X1 and X2 are the same as or different from each other, and each independently is the following Formula 1-2,

When c is 1 or more, a and b are integers of 2 or more,

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

[Formula 1-1]

In Chemical Formula 1-1,

R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroaryl group,

[Formula 1-2]

In Chemical Formula 1-2,

R6 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroaryl group,

Ar1 is a substituted or unsubstituted heterocycle,

[Formula 1-3]

In Chemical Formula 1-3,

R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroaryl group,

[Formula 1-4]

In the above formula 1-4,

R15 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroaryl group,

Ar2 is a substituted or unsubstituted heterocycle.

The present specification provides a coating composition comprising the compound.

The present specification also includes a first electrode; A second electrode; And at least one organic material layer provided between the first electrode and the second electrode, and at least one layer of the organic material layer includes the coating composition.

Finally, the present specification includes preparing a substrate; Forming a first electrode on the substrate; Forming one or more organic material layers on the first electrode; And forming a second electrode on the organic material layer, wherein forming the organic material layer includes forming one or more organic material layers using the coating composition. do.

The compound according to an exemplary embodiment of the present invention is capable of a solution process, enables a large area of a device, can be used as a material for an organic material layer of an organic light emitting device, has excellent charge transport ability, low driving voltage, high luminous efficiency and high It can provide life characteristics.

1 shows 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.

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

[Formula 1]

In Chemical Formula 1,

X1 and X2 are the same as or different from each other, and each independently represented by the following Formula 1-1 or Formula 1-2,

A is represented by the following formula 1-3,

B is represented by the following formula 1-4,

a and b are each an integer of 1 or more,

c is an integer greater than or equal to 0,

When c is 0, X1 and X2 are the same as or different from each other, and each independently is the following Formula 1-2,

When c is 1 or more, a and b are integers of 2 or more,

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

[Formula 1-1]

In Chemical Formula 1-1,

R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroaryl group,

[Formula 1-2]

In Chemical Formula 1-2,

R6 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroaryl group,

Ar1 is a substituted or unsubstituted heterocycle,

[Formula 1-3]

In Chemical Formula 1-3,

R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroaryl group,

[Formula 1-4]

In the above formula 1-4,

R15 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroaryl group,

Ar2 is a substituted or unsubstituted heterocycle.

The compound according to an exemplary embodiment of the present invention includes aniline, which acts as a push in one molecule, and quinoxaline or benzothiadiazole, which acts as a pull, in a molecule. Due to the occurrence of intramolecular charge transfer, the band gap becomes small and the charge transport ability is improved due to the smaller band gap.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

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

,

Spirofluorenyl groups such as,

(9,9-dimethylfluorenyl group), and

(9,9-diphenylfluorenyl group), and a substituted fluorenyl group such as 9,9-dioctylfluorenyl group. However, it is not limited thereto.

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

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

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

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

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

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

In one embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 2 or Chemical Formula 3.

[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3,

The definitions of A and B are the same as those in Formula 1,

Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted heteroring,

R21 to R26 and R31 to R40 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroaryl group,

a'and b'are each an integer of 1 or more,

c” is an integer of 1 or more,

a” and b” are each an integer of 2 or more.

In one embodiment of the present specification, X1 and X2 are the same as or different from each other, and are each independently represented by Chemical Formula 1-1 or Chemical Formula 1-2.

In one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to another exemplary embodiment, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to another exemplary embodiment, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluorine (F); A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

In another exemplary embodiment, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluorine (F); Methyl group; Ethyl group; Phenyl group; Or a biphenyl group.

According to one embodiment of the present specification, R1 to R5 are hydrogen.

In one embodiment of the present specification, R31 to R40 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to another exemplary embodiment, R31 to R40 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, R31 to R40 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to another exemplary embodiment, R31 to R40 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluorine (F); A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

In another exemplary embodiment, R31 to R40 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluorine (F); Methyl group; Ethyl group; Phenyl group; Or a biphenyl group.

According to one embodiment of the present specification, R31 to R40 are hydrogen.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted heteroring.

According to another exemplary embodiment, Ar1 is a heterocycle containing two substituted or unsubstituted N.

In another exemplary embodiment, Ar1 is a 5-membered or 6-membered heterocycle containing 2 substituted or unsubstituted N.

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

According to another exemplary embodiment, Ar11 and Ar12 are the same or different from each other, and each is a heterocycle that includes two independently substituted or unsubstituted N.

In another exemplary embodiment, Ar11 and Ar12 are the same as or different from each other, and each independently a 5-membered or 6-membered heterocycle containing 2 substituted or unsubstituted N.

In one embodiment of the present specification, Chemical Formula 1-2 may be represented by Chemical Formula 1-2-A or 1-2-B.

[Formula 1-2-A]

[Formula 1-2-B]

In Chemical Formulas 1-2-A and 1-2-B,

The definition of R6 to R8 is the same as the definition in Chemical Formula 1-2,

X1 is O or S,

R41 and R42 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R41 and R42 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In another exemplary embodiment, R41 and R42 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, R41 and R42 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In another exemplary embodiment, R41 and R42 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with an alkoxy group; Or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkoxy group.

According to another exemplary embodiment, R41 and R42 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a methyl group unsubstituted or substituted with an n-octyloxy group; an ethyl group substituted or unsubstituted with an n-octyloxy group; a phenyl group unsubstituted or substituted with an n-octyloxy group; Or a biphenyl group unsubstituted or substituted with an n-octyloxy group.

In another exemplary embodiment, R41 and R42 are hydrogen.

In one embodiment of the present specification, R21 to R26 and R6 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In another exemplary embodiment, R21 to R26 and R6 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, R21 to R26 and R6 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In another exemplary embodiment, R21 to R26 and R6 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluorine (F); A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Or a substituted or unsubstituted phenyl group.

According to another exemplary embodiment, R21 to R26 and R6 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluorine (F); Methyl group; Ethyl group; Or a phenyl group.

In another exemplary embodiment, R21 to R26 and R6 to R8 are hydrogen.

In one embodiment of the present specification, Chemical Formula 2 may be represented by the following Chemical Formula 2-A or Chemical Formula 2-B.

[Formula 2-A]

[Formula 2-B]

In the above formulas 2-A and 2-B,

A is represented by Chemical Formula 1-3,

a'and b'are each an integer of 1 or more,

X1 is O or S,

R6 to R8, R41 and R42 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, A is represented by Chemical Formula 1-3.

In one embodiment of the present specification, R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to another exemplary embodiment, R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to another exemplary embodiment, R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluorine (F); A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Or a substituted or unsubstituted phenyl group.

In another exemplary embodiment, R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluorine (F); Methyl group; Ethyl group; Or a phenyl group.

In another exemplary embodiment, R11 to R14 are hydrogen.

In one embodiment of the present specification, B is represented by Chemical Formula 1-4.

According to an exemplary embodiment of the present specification, Ar2 is a heterocyclic group containing two substituted or unsubstituted N.

In another exemplary embodiment, Ar2 is a 5-membered or 6-membered heterocycle containing 2 substituted or unsubstituted N.

In one embodiment of the present specification, Chemical Formula 1-4 is represented by Chemical Formula 1-4-A or 1-4-B.

[Formula 1-4-A]

[Formula 1-4-B]

In Chemical Formulas 1-4-A and 1-4-B,

The definitions of R15 and R16 are the same as those in Formula 1-4,

X2 is O or S,

R43 and R44 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R43 and R44 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In another exemplary embodiment, R43 and R44 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, R43 and R44 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In another exemplary embodiment, R43 and R44 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with an alkoxy group; Or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkoxy group.

According to another exemplary embodiment, R43 and R44 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a methyl group unsubstituted or substituted with an n-octyloxy group; an ethyl group substituted or unsubstituted with an n-octyloxy group; a phenyl group unsubstituted or substituted with an n-octyloxy group; Or a biphenyl group unsubstituted or substituted with an n-octyloxy group.

In another exemplary embodiment, R43 and R44 are hydrogen.

In one embodiment of the present specification, R15 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In another exemplary embodiment, R15 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, R15 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In another exemplary embodiment, R15 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluorine (F); A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Or a substituted or unsubstituted phenyl group.

According to another exemplary embodiment, R15 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Fluorine (F); Methyl group; Ethyl group; Or a phenyl group.

In another exemplary embodiment, R15 and R16 are fluorine (F) or hydrogen.

According to an exemplary embodiment of the present specification, the formula 3 may be represented by the following formula 3-A or 3-B.

[Formula 3-A]

[Formula 3-B]

In the above formula 3-A and 3-B,

A is represented by Chemical Formula 1-3,

B is represented by the following formula 1-4,

a” and b” are each an integer of 2 or more,

X2 is O or S,

R31 to R40, R15, R16, R43 and R44 are the same as or different from each other, and independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, a and b are each an integer of 1 or more and 3 or less.

According to an exemplary embodiment of the present specification, c is an integer of 0 or more and 3 or less.

In another exemplary embodiment, c is 0 and a and b are 1.

According to another exemplary embodiment, c is 1 and a and b are 2.

According to an exemplary embodiment of the present specification, the a'and b'are integers of 1 or more and 3 or less, respectively.

According to another exemplary embodiment, a'and b'are 1 or 2, respectively.

In one embodiment of the present specification, c” is an integer of 1 or more and 3 or less.

According to another exemplary embodiment, c” is 1.

According to an exemplary embodiment of the present specification, the a" and b" is an integer of 2 or 3, respectively. In one embodiment of the present specification, the compound of Formula 1 may be represented by any one of the following compounds 1 to 5.

[Compound 1]

[Compound 2]

[Compound 3]

[Compound 4]

[Compound 5]

The compound represented by Chemical Formula 1 according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described later.

For example, the compound represented by Chemical Formula 1 is a Buchwald-Hartwig Coupling reaction of a fused aromatic ring containing a secondary amine derivative having a monofunctional or polyfunctional group containing aniline and halogen and halogen. It can be synthesized, and the substituents can be combined by methods known in the art, and the type, position, or number of substituents can be changed according to techniques known in the art.

In one embodiment of the present specification, a coating composition including the compound represented by Chemical Formula 1 is provided.

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

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

In one embodiment of the present specification, the solvent includes, for example, chlorine-based solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; Ether-based solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; Aliphatic hydrocarbon-based solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, isosophone, tetralone, decalone, and acetylacetone; Ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyvalent values of ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, etc. Alcohol and derivatives thereof; Alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide-based solvents such as dimethyl sulfoxide; And amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; A solvent such as tetralin is exemplified, but a solvent capable of dissolving or dispersing the compound of Formula 1 according to an exemplary embodiment of the present invention is sufficient, and the solvent is not limited thereto.

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

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

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

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

According to the exemplary embodiment of the present specification, the p-doped material may be represented by the following Chemical Formula S or Chemical Formula T, but is not limited thereto.

[Formula S]

In the above formula S,

M1 and M2 are the same as or different from each other, and each independently an substituted or unsubstituted arylene group,

L is a direct bond; Or a divalent ketone (-C=O-),

Q1 and Q2 are the same as or different from each other, and each independently hydrogen; Or a sulfonic acid group (-SO ₃ H),

r1 and r2 are each an integer of 0 to 7, and when r1 is 2 or more, Q1 is the same or different from each other, and when r2 is 2 or more, Q2 is the same or different from each other.

[Formula T]

In the above formula T,

M3 and M4 are the same as or different from each other, and each independently an substituted or unsubstituted arylene group,

L1 and L3 are the same as or different from each other, and each independently an substituted or unsubstituted arylene group,

L2 is a substituted or unsubstituted alkylene group,

Q3 and Q4 are the same as or different from each other, and each independently hydrogen; Or a sulfonic acid group (-SO ₃ H),

r3 and r4 are each an integer of 0 to 7, and when r3 is 2 or more, Q3 is the same or different from each other, and when r4 is 2 or more, Q4 is the same or different from each other.

In one embodiment of the present specification, M1 and M2 are the same as or different from each other, and each independently an substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to another exemplary embodiment, M1 and M2 are the same as or different from each other, and each is an arylene group having 6 to 30 carbon atoms independently substituted or unsubstituted with fluorine (F).

According to another exemplary embodiment, the M1 and M2 are the same as or different from each other, and each independently a phenylene group substituted or unsubstituted with fluorine (F); A biphenylylene group unsubstituted or substituted with fluorine (F); Or a naphthylene group unsubstituted or substituted with fluorine (F).

In another exemplary embodiment, the M1 and M2 are the same as or different from each other, and each independently a phenylene group substituted with fluorine (F); A biphenylylene group substituted with fluorine (F); Or a naphthylene group substituted with fluorine (F).

According to another exemplary embodiment, the M1 and M2 are the same as or different from each other, and each may be independently selected from the following structures.

In one embodiment of the present specification, L is a direct bond; Or a divalent ketone (-C=O-).

In one embodiment of the present specification, r1 and r2 are each an integer of 1 to 7.

According to another exemplary embodiment, r1 and r2 are 2.

In one embodiment of the present specification, r1 and r2 are 2, and Q1 and Q2 are sulfonic acid groups (-SO ₃ H).

According to an exemplary embodiment of the present specification, the M3 and M4 are the same as or different from each other, and each independently an substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to another exemplary embodiment, M3 and M4 are the same as or different from each other, and each independently is an arylene group having 6 to 30 carbon atoms unsubstituted or substituted with fluorine (F).

According to another exemplary embodiment, the M3 and M4 are the same as or different from each other, and each independently substituted or unsubstituted with fluorine (F) a phenylene group; A biphenylylene group unsubstituted or substituted with fluorine (F); Or a naphthylene group unsubstituted or substituted with fluorine (F).

In another exemplary embodiment, the M3 and M4 are the same as or different from each other, and each independently a phenylene group substituted with fluorine (F); A biphenylylene group substituted with fluorine (F); Or a naphthylene group substituted with fluorine (F).

According to another exemplary embodiment, the M3 and M4 are the same as or different from each other, and each may be independently selected from the following structures.

In one embodiment of the present specification, L1 and L3 are the same as or different from each other, and each independently an substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to another exemplary embodiment, L1 and L3 are the same as or different from each other, and each independently substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; Or a substituted or unsubstituted naphthylene group.

In another exemplary embodiment, L1 and L3 are the same as or different from each other, and each independently a phenylene group; Biphenylylene group; Or a naphthylene group.

In one embodiment of the present specification, r3 and r4 are each an integer of 1 to 7.

According to another exemplary embodiment, r3 and r4 are 2.

In one embodiment of the present specification, r3 and r4 2 are the same, and Q3 and Q4 are sulfonic acid groups (-SO ₃ H).

According to an exemplary embodiment of the present specification, L2 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

According to another exemplary embodiment, L2 is a substituted or unsubstituted methylene group; A substituted or unsubstituted ethylene group; Or a 5-substituted or unsubstituted propylene group.

According to another exemplary embodiment, L2 may be represented by Chemical Formula A below.

[Formula A]

In Chemical Formula A,

Q5 and Q6 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or Q5 and Q6 combine with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, Q5 and Q6 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group, or Q5 and Q6 combine with each other to form a substituted or unsubstituted ring.

According to another exemplary embodiment, Q5 and Q6 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted phenyl group, or Q5 and Q6 combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

In another exemplary embodiment, Q5 and Q6 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted phenyl group, or Q5 and Q6 combine with each other to form an aromatic hydrocarbon ring substituted or unsubstituted with a substituted or unsubstituted arylamine group.

According to another exemplary embodiment, Q5 and Q6 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted phenyl group, or Q5 and Q6 combine with each other to form an aromatic hydrocarbon ring substituted or unsubstituted with a diphenylamine group substituted with a diphenylamine group.

In one embodiment of the present specification, the p-doped material may be represented by any one of the following Chemical Formulas T-1 to T-3, but is not limited thereto.

[Formula T-1]

[Formula T-2]

[Formula T-3]

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

In one embodiment of the present specification, the content of the p-doped material is 0% to 500% by weight based on the compound of Formula 1 above. According to another exemplary embodiment, the content of the p-doped material is 100% to 500% by weight based on the compound of Chemical Formula 1, and in another exemplary embodiment, 200 based on the compound of Chemical Formula 1 Weight percent to 400 weight percent.

In one embodiment of the present specification, the coating composition includes the compound of Formula 1 and the p-doped material, and the compound of Formula 1 and the p-doped material is included in the coating composition at 0.01 wt% to 10 wt% According to another exemplary embodiment, 1 wt% to 5 wt% is included.

In one embodiment of the present specification, the weight average molecular weight of the coating composition is 5,000 g/mol or less. In another exemplary embodiment, the weight average molecular weight of the coating composition is 1 or more and 5,000 g/mol or less.

In another exemplary embodiment, the viscosity of the coating composition is 2 cP to 15 cP. When the viscosity is satisfied, it is easy to manufacture the 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 at least one layer of an organic material provided between the first electrode and the second electrode, and at least one layer of the organic material layer provides an organic light emitting device including the coating composition.

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

In one embodiment of the present specification, the organic material layer including the coating composition is a light emitting layer.

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

According to the exemplary embodiment of the present specification, the organic material layer including the coating composition is an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Forming an organic layer formed using the coating composition may include coating the coating composition on the first electrode; And drying the coated coating composition.

In one embodiment of the present specification, the drying step may be performed through heat treatment, and the heat treatment temperature in the drying step by heat treatment may be 85°C to 250°C, and according to one embodiment, the temperature may be 100°C to 250°C. In another exemplary embodiment, it may be 150°C to 250°C. When the range of the heat treatment temperature is satisfied, there is an advantage that the solvent can be completely removed and sufficiently p-doped through reaction with a dopant.

In another embodiment, the heat treatment time in the step of drying by heat treatment is 1 minute to 2 hours, and in one embodiment, it may be 1 minute to 1 hour, and in another embodiment, 30 It may be from minutes to 1 hour. When the range of the heat treatment time is satisfied, there is an advantage that the solvent can be completely removed and sufficiently p-doped through reaction with a dopant.

When the step of forming the organic layer formed by using the coating composition includes drying by heat treatment, when another layer is stacked on the surface of the organic layer formed by using the coating composition, it is dissolved by a solvent or morphologically It can be prevented from being affected or decomposed.

In one embodiment of the present specification, the coating composition containing the copolymer may use a coating composition mixed with a polymer binder and dispersed.

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

Further, according to one embodiment of the present specification, the organic material layer may include the compound represented by Formula 1 alone, or the coating composition containing the compound represented by Formula 1 is dried through heat treatment to perform thinning. It may also be included, and may be included as a copolymer using a coating composition mixed with other monomers. In addition, by using a coating composition mixed with other polymers, it may be included as a copolymer, or may be included as a mixture.

As the anode material, a material having a large work function is preferably used to facilitate hole injection into the organic material layer. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SNO2: combination of metal and oxide such as Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the cathode material include metals such as barium, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There is a multilayer structure 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 an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in the light emitting layer. A compound which prevents migration of the excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

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

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

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

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

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

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

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

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

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

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

< Manufacturing example >

Manufacturing example 1. Compound Preparation

Manufacturing example 1-1. Preparation of compound 1

[Formula A]

[Compound 1]

Formula A (2g, 7.26mmol), 5,8-dibromoquinoxanline (0.951g, 3.30mmol), sodium tert-butoxide (0.952) under nitrogen atmosphere g, 9.90 mmol), bis(dibenzylideneacetone)palladium(0) [Bis(dibenzylideneacetone)palladium(0)] (0.114g), (±)-2,2′-bis(diphenylphosphino)-1 Put 100 mL of toluene in ,1′-binaphthalene [(±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene] (0.185g, 0.297mmol) and reflux for 12 hours. After lowering the temperature to room temperature, wash it with water, remove residual water with MgSO ₄ , add hydrazine monohydrate, stir for 30 minutes at room temperature, precipitate in hexane, filter solids and dry under vacuum Compound 1 was obtained. MS (M/z): 676

Formula A was synthesized with reference to New Journal of Chemistry, 28. 1235 2004.

Manufacturing example 1-2. Preparation of compound 4

[Formula A]

[Compound 4]

Formula A (2 g, 7.26 mmol), 4,7-dibromobenzo [c]-1,2,5-thiadiazole under a nitrogen atmosphere (4,7-dibromobenzo[c]-1,2,5-thiadiazole) (0.971 g, 3.30 mmol), sodium tert-butoxide (0.952 g, 9.90 mmol), bis(dibenzylideneacetone)palladium(0) [Bis(dibenzylideneacetone)palladium(0)] (0.114 g), [(±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene] [(±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene] (0.185g , 0.297mmol) and refluxed for 12 hours. After lowering the temperature to room temperature, wash it with water, remove residual water with MgSO ₄ , add hydrazine monohydrate, stir at room temperature for 30 minutes, precipitate in hexane, filter solids and dry under vacuum Compound 4 was obtained. MS (M/z): 682

Manufacturing example 1-3. Preparation of compound 5

[Formula A] [Formula B]

[Compound 5]

Formula A (2g, 7.26mmol), Formula B (1.089g, 3.30mmol), sodium tert-butoxide (0.952g, 9.90mmol), bis(dibenzylideneacetone)palladium under nitrogen atmosphere ( 0) [Bis(dibenzylideneacetone)palladium(0)] (0.114g), (±)-2,2′-bis(diphenylphosphino)- 1,1′-binaphthalene [(±)-2,2′ -Bis(diphenylphosphino)-1,1'-binaphthalene] (0.185 g 0.297 mmol) was added with 100 mL of toluene and refluxed for 12 hours. After lowering the temperature to room temperature, wash it with water, remove residual water with MgSO ₄ , add hydrazine monohydrate, stir for 30 minutes at room temperature, precipitate in hexane, filter solids, and under vacuum. Dry to obtain the compound 5. MS (M/z): 718

Manufacturing example 1-4. Preparation of compound 2

[Formula C] [Formula D] [Compound 2]

Formula C (0.658 g, 3.30 mmol), Formula D (1.518 g, 7.26 mmol), sodium tert-butoxide (0.952 g, 9.90 mmol), bis(dibenzylideneacetone) palladium under nitrogen atmosphere (0) [Bis(dibenzylideneacetone)palladium(0)] (0.114g), (±)-2,2′-bis(diphenylphosphino)- 1,1′-binaphthalene [(±)-2,2 100 mL of toluene was added to ′-Bis(diphenylphosphino)-1,1′-binaphthalene] (0.185g, 0.297mmol) and refluxed for 12 hours. After lowering the temperature to room temperature, wash it with water, remove residual water with MgSO ₄ , add hydrazine monohydrate, stir at room temperature for 30 minutes, precipitate in hexane, filter solids and dry under vacuum , Compound 2 was obtained. MS (M/z): 455

The formula C was synthesized with reference to New Journal of Chemistry, 28. 1235 2004, and the formula D was synthesized with reference to Tetrahedron, 2017. 73. 1618.

Manufacturing example 1-5. Preparation of compound 3

[Formula C] [Formula E] [Compound 3]

Formula C (0.658g, 3.30mmol), Formula E (1.561g, 7.26mmol), sodium tert-butoxide (0.952g, 9.90mmol), bis(dibenzylideneacetone)palladium under nitrogen atmosphere (0) [Bis(dibenzylideneacetone)palladium(0)] (0.114g), (±)-2,2′-bis(diphenylphosphino)- 1,1′-binaphthalene [(±)-2,2 100 mL of toluene was added to ′-Bis(diphenylphosphino)-1,1′-binaphthalene] (0.185g, 0.297mmol) and refluxed for 12 hours. After lowering the temperature to room temperature, wash it with water, remove residual water with MgSO ₄ , add hydrazine monohydrate, stir at room temperature for 30 minutes, precipitate in hexane, filter solids and dry under vacuum Compound 3 was obtained. MS (M/z): 467

Formula C was synthesized with reference to New Journal of Chemistry, 28. 1235 2004, Formula E was synthesized with reference to Macromolecular Rapid Communications, 2016. 37. 1352.

Manufacturing example 1-6. Preparation of compound P-1

[Formula F]

[Compound P-1]

Formula F (1.34 g, 7.26 mmol), 5, 8-dibromoquinoxanline (0.951 g, 3.30 mmol), sodium tert-butoxide (0.952) under nitrogen atmosphere g, 9.90mmol), bis(dibenzylideneacetone)palladium(0) [Bis(dibenzylideneacetone)palladium(0)] (0.114g), (±)-2,2′-(±)-2,2′- Bis(diphenylphosphino)-1,1′-binaphthalene [(±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene] (0.185g, 0.297mmol) with 100mL of toluene 12 Reflux for an hour. After lowering the temperature to room temperature, wash it with water, remove residual water with MgSO ₄ , add hydrazine monohydrate, stir at room temperature for 30 minutes, precipitate in hexane, filter solids and dry under vacuum The compound P-1 was obtained. MS (M/z): 494

Formula F was synthesized with reference to New Journal of Chemistry, 28. 1235 2004.

Manufacturing example 2. Preparation of coating composition

Manufacturing example 2-1. Preparation of coating composition 1

Compound 1 and the following formula T-1 were dissolved in dimethylformamide in a ratio of 1:4 to prepare a 2 wt% solution.

[Formula T-1]

Manufacturing example 2-2. Preparation of coating composition 2

The compound 4 and the formula T-1 were dissolved in dimethylformamide in a ratio of 1:4 to prepare a 2 wt% solution.

Manufacturing example 2-3. Preparation of coating composition 3

The compound 5 and the formula T-1 were dissolved in dimethylformamide in a ratio of 1:4 to prepare a 2 wt% solution.

Manufacturing example 2-4. Preparation of coating composition 4

The compound 2 and the formula T-1 were dissolved in dimethylformamide in a ratio of 1:4 to prepare a 2 wt% solution.

Manufacturing example 2-5. Preparation of coating composition 5

The compound 3 and the formula T-1 were dissolved in dimethylformamide in a ratio of 1:4 to prepare a 2 wt% solution.

Manufacturing example 2-6. Preparation of coating composition 6

The compound P-1 and the formula T-1 were dissolved in dimethylformamide in a ratio of 1:4 to prepare a 2 wt% solution.

Manufacturing example 2-7. Preparation of coating composition 7

The following compound P-2 and the formula T-1 were dissolved in dimethylformamide in a ratio of 1:4 to prepare a 2 wt% solution.

[Formula P-2]

The above formula P-2 was synthesized with reference to Journal of organic chemistry, 2005. 70. 2754.

< Example >

Example One.

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

The coating composition 1 was spin-coated on the substrate thus prepared, coated to a thickness of 300 mm 3, and heat-treated at 230° C. for 30 minutes in an N ₂ atmosphere to form a hole injection layer. Thereafter, on the hole injection layer, the following compound HT-1 was dissolved in toluene at 1 wt/v% and spin-coated to form a hole transport layer.

[Compound HT-1] [Compound EM-1]

[Compound EM-2] [Compound ET-1]

Subsequently, after transferring to a vacuum evaporator, compound EM-1 and compound EM-2 were vacuum-deposited to a thickness of 300 Pa at a ratio of 0.92:0.08 on the hole transport layer to form a light emitting layer. The compound ET-1 was vacuum deposited on the light emitting layer to a thickness of 200 Pa to form an electron injection and transport layer. A cathode was formed by sequentially depositing aluminum with a thickness of 12 MPa and a thickness of 2000 MPa on the electron injection and transport layer.

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

Subsequently, sealing was performed by bonding the glass to the glass using a photocurable epoxy resin, thereby producing an organic bladder device having a multilayer structure. Subsequent operation was performed at room temperature (25°C) in the air.

Example 2.

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

Example 3.

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

Example 4.

An organic light emitting device was manufactured in the same manner as in Example 1, except that the coating composition 4 was used instead of the coating composition 1 as the hole injection layer in Example 1.

Example 5.

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

Comparative example One.

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

Comparative example 2.

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

Example 1-5 and Comparative Example 1 were to second measurement of driving voltage and light emission efficiency of the organic light emitting device prepared with a current density of 10mA / cm ² in 95% of the initial luminance at a current density of 10mA / cm ² is Life time was measured. The results are shown in Table 1 below.

Practice/Comparative Example Driving voltage (V) Current efficiency (cd/A) Power efficiency (lm/W) Life time
(95%, h) Example 1 3.60 5.09 4.89 97 Example 2 3.58 4.97 4.36 80 Example 3 3.61 5.01 4.36 88 Example 4 3.63 5.20 4.50 72 Example 5 3.76 5.73 4.79 59 Comparative Example 1 4.53 5.43 3.76 38 Comparative Example 2 4.23 1.62 1.21 40

The compounds used in Examples 1 to 5 have a longer conjugation length than the compounds used in Comparative Examples 1 and 2, or have a greater number of quinoxaline or benzothiadiazoles that act as electron pulls. From the results of Table 1, it was confirmed that the organic light-emitting devices of Examples 1 to 5 prepared using the compound of Formula 1 herein have improved performance and lifespan than the organic light-emitting devices of Comparative Examples 1 to 2.

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

Claims (14)

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

In Chemical Formula 1,
X1 and X2 are the same as or different from each other, and each independently represented by the following Formula 1-1 or Formula 1-2,
A is represented by the following formula 1-3,
B is represented by the following formula 1-4,
a and b are each an integer of 1 or more,
c is an integer greater than or equal to 0,
When c is 0, X1 and X2 are the same as or different from each other, and each independently is the following Formula 1-2,
When c is 1 or more, a and b are integers of 2 or more,
When a, b, and c are each 2 or more, structures in parentheses are the same or different from each other,
[Formula 1-1]

In Chemical Formula 1-1,
R1 to R5 are hydrogen,
[Formula 1-2]

In Chemical Formula 1-2,
R6 to R8 are hydrogen,
Ar1 is a heteroatom, a pentagonal or hexagonal heterocycle containing one or more of N and S,
[Formula 1-3]

In Chemical Formula 1-3,
R11 to R14 are hydrogen,
[Formula 1-4]

In the above formula 1-4,
R15 and R16 are the same as or different from each other, and each independently a hydrogen or halogen group,
Ar2 is a heteroatom, a pentagonal or hexagonal heterocycle containing one or more of N and S. The method according to claim 1, wherein Formula 1 is a compound represented by Formula 2 or Formula 3:
[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3,
The definitions of A and B are the same as those in Formula 1,
Ar11 and Ar12 are the same as or different from each other, and each independently a heteroatom, a pentagonal or hexagonal heterocycle containing one or more of N and S, and
R21 to R26 and R31 to R40 are hydrogen,
a'and b'are each an integer of 1 or more,
c” is an integer of 1 or more,
a” and b” are each an integer of 2 or more. The method according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently a 5- or 6-membered heterocycle containing 2 N's. The method according to claim 1, wherein the formula 1-2 is a compound represented by the following formula 1-2-A or 1-2-B:
[Formula 1-2-A]

[Formula 1-2-B]

In Chemical Formulas 1-2-A and 1-2-B,
The definition of R6 to R8 is the same as the definition in Chemical Formula 1-2,
X1 is S,
R41 and R42 are hydrogen. The method according to claim 1, wherein the formula 1-4 is a compound represented by the following formula 1-4-A or 1-4-B:
[Formula 1-4-A]

[Formula 1-4-B]

In Chemical Formulas 1-4-A and 1-4-B,
The definitions of R15 and R16 are the same as those in Formula 1-4,
X2 is S,
R43 and R44 are hydrogen. The method according to claim 1, wherein the compound represented by Formula 1 is a compound represented by any one of the following compounds 1 to 5:
[Compound 1]

[Compound 2]

[Compound 3]

[Compound 4]

[Compound 5]

. A coating composition comprising a compound according to claim 1. The coating composition of claim 7, wherein the coating composition further comprises a p-doped material. The coating composition of claim 7, wherein the coating composition has a viscosity of 2 cP to 15 cP. A first electrode;
A second electrode; And
It includes at least one organic layer provided between the first electrode and the second electrode,
At least one layer of the organic layer comprises the coating composition of claim 7 wherein the organic light emitting device. The organic light emitting device of claim 10, wherein the organic material layer including the coating composition is a hole transport layer, a hole injection layer, or a layer simultaneously performing hole transport and hole injection. Preparing a substrate;
Forming a first electrode on the substrate;
Forming one or more organic material layers on the first electrode; And
And forming a second electrode on the organic material layer,
The step of forming the organic material layer includes forming one or more organic material layers using the coating composition of claim 7. The method of claim 12, wherein the organic material layer formed using the coating composition is formed using spin coating. The method according to claim 12, Forming an organic layer formed using the coating composition is
Coating the coating composition on the first electrode; And
Method of manufacturing an organic light emitting device comprising the step of drying the coated coating composition.

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