KR102443861B1 - Organic light emitting device - Google Patents

Abstract

The present specification includes a first electrode;
a second electrode provided to face the first electrode;
a light emitting layer provided between the first electrode and the second electrode;
a second organic material layer provided between the first electrode and the light emitting layer; and
a first organic material layer provided between the first electrode and the second organic material layer;
The light emitting layer includes a compound represented by Formula 1,
The first organic layer includes a cured product of a coating composition comprising a compound of Formula 2 and a compound of Formula 3,
The second organic material layer relates to an organic light emitting device comprising a polymer including a unit represented by Formula 4.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

The present specification relates to an organic light emitting device.

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

As materials used in organic light emitting devices, pure organic materials or complex compounds in which organic materials and metals are complexed account for most of them. can be divided into Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state during oxidation, is mainly used. On the other hand, as an electron injection material or an electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state during reduction is mainly used. As the light emitting layer material, a material having both p-type properties and n-type properties, that is, a material having a stable form in both oxidation and reduction states, is preferable. desirable.

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

First, it is preferable that the material used in the organic light emitting device has excellent thermal stability. This is because joule heat is generated by the movement of electric charges in the organic light emitting diode. NPB, which is currently mainly used as a material for the hole transport layer, has a glass transition temperature of 100° C. or less, so it is difficult to use in an organic light emitting device that requires a high current.

Second, in order to obtain a high-efficiency organic light-emitting device that can be driven at a low voltage, holes or electrons injected into the organic light-emitting device should be smoothly transferred to the light-emitting layer, and the injected holes and electrons should not escape out of the light-emitting layer. For this purpose, a material used for an organic light emitting diode must have an appropriate band gap and HOMO or LUMO energy level. In the case of PEDOT:PSS, which is currently used as a hole transport material in an organic light emitting device manufactured by a solution coating method, the LUMO energy level is lower than the LUMO energy level of an organic material used as a light emitting layer material. there are difficulties in

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

Therefore, there is a demand in the art to develop an organic material having the above requirements.

Korean Patent Publication No. 2012-0112277

The present specification provides an organic light emitting device.

The present specification includes a first electrode;

a second electrode provided to face the first electrode;

a light emitting layer provided between the first electrode and the second electrode;

a second organic material layer provided between the first electrode and the light emitting layer; and

a first organic material layer provided between the first electrode and the second organic material layer;

The light emitting layer comprises a compound represented by the following formula (1),

The first organic layer includes a cured product of a coating composition comprising a compound of Formula 2 and a compound of Formula 3,

The second organic material layer provides an organic light emitting device comprising a polymer including a unit represented by the following formula (4).

[Formula 1]

In Formula 1,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L1 is a direct bond; Or a substituted or unsubstituted arylene group,

[Formula 2]

In Formula 2,

L11 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R11 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar11 and Ar12 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

X11 and X12 are the same as or different from each other, and each independently a photocurable group or a thermosetting group,

n11 and n14 are each independently an integer of 0 to 5,

n12 and n16 are each independently an integer of 0 to 4,

n13 and n15 are each independently an integer of 0 to 3,

When each of n11 to n16 is 2 or more, the substituents in parentheses are the same as or different from each other,

m11 and m12 are each 0 or 1,

[Formula 3]

In Formula 3,

At least one of R101 to R120 is F, a cyano group, or a substituted or unsubstituted fluoroalkyl group,

At least one of the remaining R101 to R120 is a curing group,

The remaining R101 to R120 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitro group; -C(O)R; -OR; -SR; -SO ₃ R; -COOR; -OC(O)R; -C(O)NRR'; a substituted or unsubstituted alkyl group; a substituted or unsubstituted fluoroalkyl 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 heteroaryl group,

R and R' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,

[Formula 4]

In Formula 4,

L101 to L105 are the same as or different from each other, and each independently a direct bond; -O-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; a substituted or unsubstituted divalent amine group; Or a substituted or unsubstituted heteroarylene group,

b101 is an integer from 1 to 10,

When b1 is 2 or more, two or more L101 are the same as or different from each other,

Ar101 to Ar103 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R201 to R205 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; hydroxyl group; nitrile group; 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,

r204 and r205 are each an integer of 0 to 3,

When r204 and r205 are each 2 or more, two or more R204 and R205 are the same as or different from each other,

m1 is the number of repetitions of the unit, and is an integer from 1 to 10,000.

In addition, the present invention comprises the steps of forming a first electrode on a substrate;

applying a coating composition comprising the compound of Formula 2 and the compound of Formula 3 on the first electrode;

forming a first organic material layer by curing the applied coating composition;

forming a second organic material layer by applying a coating composition comprising a polymer including a unit represented by Formula 4 on the first organic material layer;

It provides a method of manufacturing an organic light emitting device comprising the step of forming a light emitting layer by applying a coating composition including the compound represented by Formula 1 on the second organic material layer.

The organic light emitting device according to an exemplary embodiment of the present specification includes the anthracene compound of Formula 1 in the light emitting layer, and the fluorene compound of Formula 2 and the ionic compound of Formula 3 in the hole injection layer. Including cargo, the hole transport layer contains the polymer including the unit of Formula 4, and in particular, the compounds of Formulas 2 and 3 of the hole injection layer contain a functional group that is polymerized by heat or light, so that sufficient heat after film formation Alternatively, when light is applied, resistance to the process solvent is generated, and the compound according to an exemplary embodiment of the present specification is washed away or the film property is not changed by preventing the movement of the interlayer material, so that a reproducible organic light emitting device can be manufactured. .

In addition, the hole transport layer is an organic material layer formed using a polymer having a carbazole group substituted with an amine group of Formula 4 as a side chain, and the hole transport layer has excellent thermal and optical stability after curing through heat and light, and solubility in other solvents Since it does not have, a lamination film forming process may be performed through another solution process on the film forming process.

In this case, the anthracene compound of Formula 1 can be solution-processed in the light emitting layer, so that the device can have a large area, and it can be used as a material for the organic material layer of the organic light emitting device.

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

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

In the present specification, when a member is said to be located “on” another member, this includes not only a case in which a member is in contact with another member but also a case in which another member is present between the two members.

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

Throughout this specification, the term "combination of these" included in the expression of the Markush form means one or more mixtures or combinations selected from the group consisting of the components described in the expression of the Markush form, and the components It is meant to include one or more selected from the group consisting of.

An exemplary embodiment of the present specification includes a first electrode;

a second electrode provided to face the first electrode;

a light emitting layer provided between the first electrode and the second electrode;

a second organic material layer provided between the first electrode and the light emitting layer; and

A first organic material layer provided between the first electrode and the second organic material layer,

The light emitting layer includes a coating composition comprising the compound represented by Formula 1,

The first organic material layer includes a cured product of the coating composition comprising the compound represented by Chemical Formulas 2 and 3,

The second organic material layer provides an organic light emitting device comprising a polymer including a unit represented by the formula (4).

According to an exemplary embodiment of the present specification, the compounds of Formulas 1 to 3 and the polymer including the unit represented by Formula 4 are preferably compounds having solubility in a suitable organic solvent.

As used herein, the terms “thermosetting group or photocurable group” and “curing group” may refer to a reactive substituent that cross-links compounds by exposure to heat and/or light. Crosslinking may be generated by connecting radicals generated while decomposing carbon-carbon multiple bonds and cyclic structures by heat treatment or light irradiation.

In one embodiment of the present specification, the thermosetting group or the photocurable group is any one of the following structures.

.

.

In the exemplary embodiment of the present specification, in the case of a fluorene-based compound including a thermosetting group or a photocurable group, an organic light emitting device can be manufactured by a solution coating method, which is economical in terms of time and cost.

In addition, when the coating layer is formed by using a coating composition containing a fluorene-based compound including a thermosetting group or a photocurable group, since the thermosetting group or the photocurable group is crosslinked by heat or light, it is added on top of the coating layer By preventing the fluorene-based compound contained in the coating composition from being washed away by the solvent when laminating the layer of the coating composition, an additional layer can be laminated on top while maintaining the coating layer.

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

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

According to an exemplary embodiment of the present specification, in the case of a fluorene-based compound cross-linked by heat treatment or light irradiation, since a plurality of fluorene-based compounds are cross-linked and provided in the organic light emitting device in the form of a thin film, there is an excellent effect of thermal stability .

In addition, since the fluorene-based compound according to an exemplary embodiment of the present specification includes an amine structure in its core structure, it may have an energy level and a band gap suitable as a hole injection, hole transport material, or light emitting material in an organic light emitting device. In addition, by adjusting the substituent of the fluorene-based compound of Formula 1 according to an exemplary embodiment of the present specification, an appropriate energy level and a band gap can be finely adjusted, and the interfacial property between organic materials is improved, so that a low driving voltage and a high An organic light emitting device having luminous efficiency can be provided.

In an exemplary embodiment of the present specification, the curing group is any one of the following curing groups.

[hardener group]

In the curing group, L is a direct bond; O; S; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

k is 1 or 2, and when k is 2, the substituents in parentheses are the same as or different from each other,

R21 is a substituted or unsubstituted alkyl group.

In the exemplary embodiment of the present specification, various curing groups may be used as long as the curing group is a curing device capable of curing, and the curing group is not limited to the curing group.

Hereinafter, the substituents of the present specification will be described in detail below, but the present invention is not limited thereto.

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

refers to a site bonded to another substituent or a bonding group.

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; imid; amino group; an alkyl group; alkoxy group; aryloxy group; cycloalkyl group; alkenyl group; amine group; boron group; silyl group; phosphine oxide group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; aralkyl group; aralkenyl group; an alkylaryl group; an aralkylamine group; arylamine group; an aryl phosphine group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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

In the present specification, the alkyl group may be a straight chain, branched chain, or cyclic chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3- Dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2- propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, is not limited to

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be, but is not limited thereto.

In the present specification, the aryloxy group is a phenoxy group, 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-anthracenyl oxy group, 2-anthracenyloxy group, 9-anthracenyloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiR _aa R _bb R _cc , wherein R _aa , R _bb and R _cc are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, there are trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc., but is not limited thereto. .

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 40. Specific examples 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, etc., but are not limited thereto.

The alkyl group may be substituted with an aryl group or a heterocyclic group to function as an arylalkyl group or a heteroarylalkyl group. The aryl group and heterocyclic group may be selected from examples of an aryl group or heterocyclic group to be described later.

In the present specification, the length of the alkyl group does not affect the conjugated length of the compound, and may affect the application of the compound to an organic light emitting device application method, for example, a vacuum deposition method or a solution application method.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto. does not

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

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

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

and

etc. can be However, the present invention is not limited thereto.

The aryl group may be substituted with an alkyl group or an alkoxy group to function as an arylalkyl group or an aryloxy group. The alkyl group or the alkoxy group may be selected from the examples described above.

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. The amine group may be substituted with the aforementioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof, and specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group. group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group , a triphenylamine group, and the like, but is 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 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. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above. Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthra Cenyl amine, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole and triphenyl amine group, but is not limited thereto.

In the present specification, the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, a triazinyl group Jolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidyl group, pyridopyrazinyl group, pyrazinopyrazinyl group , isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, pe Nonthrolinyl group (phenanthroline), isoxazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but is not limited thereto.

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

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.

In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.

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

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

In an exemplary embodiment of the present specification, L in Formula 1 is a direct bond; Or a substituted or unsubstituted arylene group.

In an exemplary embodiment of the present specification, L in Formula 1 is a direct bond; Or a substituted or unsubstituted phenylene group.

In an exemplary embodiment of the present specification, L in Formula 1 is a direct bond.

In an exemplary embodiment of the present specification, L in Formula 1 is a phenylene group.

In an exemplary embodiment of the present specification, L in Formula 1 is a carbonyl group; imide group; amino group; a silyl group substituted with a substituted or unsubstituted aryl group; a substituted or unsubstituted boron group; a substituted or unsubstituted C 2 to C 60 alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aralkyl group; a substituted or unsubstituted aralkenyl group; a substituted or unsubstituted alkylaryl group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted phenylene group with a substituent selected from the group consisting of a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C14 aryl group; or a substituted or unsubstituted C10 to C20 heteroaryl group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted benzofluorene group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium or an alkyl group; a naphthyl group unsubstituted or substituted with deuterium or an alkyl group; a fluorene group unsubstituted or substituted with deuterium or an alkyl group; a benzofluorene group unsubstituted or substituted with deuterium or an alkyl group; a dibenzofuran group unsubstituted or substituted with deuterium or an alkyl group; or a dibenzothiophene group unsubstituted or substituted with deuterium or an alkyl group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium or an alkyl group; naphthyl group; a fluorene group unsubstituted or substituted with an alkyl group; a benzofluorene group unsubstituted or substituted with an alkyl group; dibenzofuran group; or a dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium, a methyl group, or a butyl group; naphthyl group; a fluorene group substituted with a methyl group; a benzofluorene group substituted with a methyl group; dibenzofuran group; or a dibenzothiophene group.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 is selected from the following compounds.

According to an exemplary embodiment of the present specification, R11 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to another exemplary embodiment, R11 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 1 to C 40 alkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In another exemplary embodiment, R11 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; or a substituted or unsubstituted C 1 to C 20 alkyl group.

According to another exemplary embodiment, R11 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted isobutyl group; a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted pentyl group; or a substituted or unsubstituted hexyl group.

In another exemplary embodiment, R11 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a methyl group unsubstituted or substituted with a halogen group; an ethyl group unsubstituted or substituted with a halogen group; a propyl group unsubstituted or substituted with a halogen group; a substituted or unsubstituted butyl group; an isobutyl group unsubstituted or substituted with a halogen group; tert-butyl group unsubstituted or substituted with a halogen group; a pentyl group substituted or unsubstituted with a halogen group; or a hexyl group unsubstituted or substituted with a halogen group.

According to another exemplary embodiment, R11 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; fluorine; a methyl group unsubstituted or substituted with fluorine; ethyl group; Profile group; butyl group; isobutyl group; tert-butyl group; pentyl group; or a hexyl group.

In another exemplary embodiment, R11 and R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; fluorine; a methyl group unsubstituted or substituted with fluorine; ethyl group; Profile group; butyl group; isobutyl group; tert-butyl group; pentyl group; or a hexyl group.

According to another exemplary embodiment, R12, R13, R15 and R16 are hydrogen.

According to an exemplary embodiment of the present specification, n12, n13, n15, and n16 are each an integer of 0 to 2.

According to another exemplary embodiment, n12, n13, n15, and n16 are 0 or 1, respectively.

In another exemplary embodiment, each of n11 and n14 is an integer of 0 to 5.

In another exemplary embodiment, n11 and n14 are 0, 1, 2, or 5, respectively.

In an exemplary embodiment of the present specification, L11 is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

In an exemplary embodiment of the present specification, L11 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 2 to C 30 heteroarylene group.

According to another exemplary embodiment, L11 is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted fluorenylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted binaphthylene group; Alternatively, it may be a substituted or unsubstituted naphthylene group, or a group in which two or more of the substituents are connected.

According to another exemplary embodiment, L11 is selected from the following structural formulas.

The structures may include an additional substituted or unsubstituted alkyl group; Or it may be further substituted with a substituted or unsubstituted aryl group.

In the above structures, R21 to R25 and R30 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C30 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, R21 to R25 and R30 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 1 to C 20 alkyl group; or a substituted or unsubstituted C6-C20 aryl group.

In an exemplary embodiment of the present specification, R21 to R25 and R30 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 1 to C 20 alkyl group; or an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R21 to R25 and R30 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 1 to C 8 alkyl group; or an aryl group having 6 to 12 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, R21 to R25 and R30 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted t-butyl group; a substituted or unsubstituted pentyl group; a substituted or unsubstituted hexyl group; or a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, R21 to R25 and R30 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; ethyl group; Profile group; butyl group; t-butyl group; pentyl group; hexyl group; or a phenyl group unsubstituted or substituted with a methyl group, a butyl group, or a hexyl group.

In an exemplary embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In another exemplary embodiment, Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C40 aryl group; Or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

In the exemplary embodiment of the present specification, Ar11 and Ar12 may be any one of the following structures, but are not limited thereto, and the following structures may be further substituted.

In the above structures,

W is O, S, NRa, CRbRc or SiRdRe;

R41 to R51, Ra, Rb, Rc, Rd and Re 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,

p1 is an integer from 0 to 7,

p2, p4 and p5 are each an integer from 0 to 4,

p3 and p6 are each an integer from 0 to 5,

When p1 to p6 are each 2 or more, the substituents in parentheses are the same as or different from each other.

In an exemplary embodiment of the present specification, R49 to R51 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C30 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, R49 to R51 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 1 to C 20 alkyl group; or a substituted or unsubstituted C6-C20 aryl group.

In another exemplary embodiment, R49 to R51 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 1 to C 8 alkyl group; or a substituted or unsubstituted C6-C12 aryl group.

In another exemplary embodiment, R49 to R51 are hydrogen.

In an exemplary embodiment of the present specification, R41 to R48 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 1 to C 20 alkyl group; or a substituted or unsubstituted C6-C20 aryl group.

In another exemplary embodiment, R41 to R48 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 1 to C 8 alkyl group; or a substituted or unsubstituted C6-C12 aryl group.

In an exemplary embodiment of the present specification, R41 to R48 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; fluorine; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted biphenyl group.

In another exemplary embodiment, R41 to R48 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; fluorine; methyl group; ethyl group; Profile group; phenyl group; naphthyl group; or a biphenyl group.

In an exemplary embodiment of the present specification, W is O.

In the exemplary embodiment of the present specification, W is S.

In an exemplary embodiment of the present specification, W is CRbRc.

In the exemplary embodiment of the present specification, W is SiRdRe.

In an exemplary embodiment of the present specification, Rb, Rc, Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C30 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, Rb, Rc, Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 1 to C 20 alkyl group; or a substituted or unsubstituted C6-C20 aryl group.

In another exemplary embodiment, Rb, Rc, Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 1 to C 8 alkyl group; or a substituted or unsubstituted C6-C12 aryl group.

According to another exemplary embodiment, Rb, Rc, Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; or a substituted or unsubstituted phenyl group.

According to another exemplary embodiment, Rb, Rc, Rd and Re are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; ethyl group; or a phenyl group.

According to an exemplary embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; It is a substituted or unsubstituted fluorenyl group.

In an exemplary embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium or an alkyl group; a biphenyl group unsubstituted or substituted with deuterium or an alkyl group; a naphthyl group unsubstituted or substituted with deuterium or an alkyl group; It is a fluorenyl group unsubstituted or substituted with deuterium or an alkyl group.

In another exemplary embodiment, Ar11 and Ar12 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; naphthyl group; It is a fluorenyl group substituted with a methyl group.

According to an exemplary embodiment of the present specification, m11 and m12 are 0 or 1.

When m11 is 0, carbon 9 of fluorene and X11 are directly bonded, and the specific structure is as follows.

When m12 is 0, carbon 9 of fluorene and X12 are directly bonded, and the specific structure is as follows.

In an exemplary embodiment of the present specification, X11 and X12 are the same as or different from each other, each independently a photocurable group or a thermosetting group, and may have the following structure.

일 수 있다.According to another exemplary embodiment, the X11 and X12 are

can be

According to an exemplary embodiment of the present invention, the compound of Formula 2 may be represented by any one of the following compounds.

.

.

In the exemplary embodiment of the present specification, if the compound represented by Chemical Formula 3 does not have a curing group, curing is not performed, and thus, the compound of Chemical Formula 3 of the present specification decreases the characteristics of the device due to movement between the electrode layers. In addition, when the number of curing machines is increased, the curing rate of the coating composition is increased and the film retention rate is improved.

In an exemplary embodiment of the present specification, at least one of R101 to R105 is F, a cyano group, or a substituted or unsubstituted fluoroalkyl group,

At least one of the remaining R101 to R105 is a curing group,

The remaining R101 to R105 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitro group; -C(O)R; -OR; -SR; -SO ₃ R; -COOR; -OC(O)R; -C(O)NRR'; a substituted or unsubstituted alkyl 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,

R and R' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,

The R106 to R120 are the same as or different from each other, and each independently a curing group; F; cyano group; a substituted or unsubstituted fluoroalkyl group; Hydrogen; heavy hydrogen; nitro group; -C(O)R; -OR; -SR; -SO ₃ R; -COOR; -OC(O)R; -C(O)NRR _' ; a substituted or unsubstituted alkyl 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,

R and R' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, among the benzene ring to which R101 to R105 of Formula 3 are bonded, the benzene ring to which R106 to R110 are bonded, the benzene ring to which R111 to R115 are bonded, and the benzene ring to which R116 to R120 are bonded At least one benzene ring is selected from the following structural formulas.

In one embodiment of the present specification, among the benzene ring to which R101 to R105 of Formula 3 are bonded, the benzene ring to which R106 to R110 are bonded, the benzene ring to which R111 to R115 are bonded, and the benzene ring to which R116 to R120 are bonded At least one benzene ring is selected from the following structural formulas.

In an exemplary embodiment of the present specification, the compound of Formula 3 is selected from the following structural formulas.

In the above structural formula, n is an integer of 1 to 3, m is an integer of 1 to 3, m+n=4,

q is an integer from 0 to 3, r is an integer from 1 to 4, q+r=4,

Z is deuterium; halogen group; nitro group; cyano group; amino group; -C(O)R; -OR; -SR; -SO ₃ R; -COOR; -OC(O)R; -C(O)NRR'; a substituted or unsubstituted alkyl 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,

l is an integer from 1 to 4, and when l is 2 or more, Z is the same as or different from each other,

R and R' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted alkyl group.

In an exemplary embodiment of the present specification, the compound represented by Formula 3 is an anionic group.

In an exemplary embodiment of the present specification, the cationic group is an onium compound.

In the present specification, the onium compound refers to a compound formed by coordination bonding of hydrogen ions or other organic radicals with lone pairs of electrons such as oxygen, sulfur, nitrogen, and phosphorus.

In an exemplary embodiment of the present specification, the cationic group is selected from the following structural formulas.

In the structural formula, X ₁₀₁ to X ₁₇₅ are the same as or different from each other, and each independently hydrogen; cyano group; nitro group; halogen group; -COOR; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted fluoroalkyl group; Or a substituted or unsubstituted aryl group, or a curing group,

R is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,

p is an integer from 0 to 10,

a is 1 or 2, b is 0 or 1, a+b=2,

X ₁₇₇ to X ₁₇₉ are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or groups adjacent to each other combine with each other to form a ring.

In an exemplary embodiment of the present specification, the X ₁₀₁ to X ₁₇₅ are the same as or different from each other, and each independently hydrogen; cyano group; nitro group; F; Cl; -COOR; methyl group; ethyl group; Profile group; butyl group; pentane group; hexane group; methoxy group; cyclopropyl group; ethoxyethoxy; phenyl group; naphthyl group; Or a curing group, wherein R is a methyl group.

In an exemplary embodiment of the present specification, the cation group is a monovalent cationic group.

In an exemplary embodiment of the present specification, the monovalent cationic group includes Na ⁺ , Li ⁺ , K ⁺ , and the like, but is not limited thereto.

In an exemplary embodiment of the present specification, in Formula 4, L101 to L105 are the same as or different from each other, and each independently a direct bond; -O-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; a substituted or unsubstituted divalent amine group; or a substituted or unsubstituted heteroarylene group.

In an exemplary embodiment of the present specification, in Formula 4, L101 to L105 are the same as or different from each other, and each independently represent a substituted or unsubstituted C6-C30 arylene group.

In an exemplary embodiment of the present specification, in Formula 4, L101 to L105 are the same as or different from each other, and each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted a naphthylene group, or a substituted or unsubstituted fluorenylene group.

In an exemplary embodiment of the present specification, in Formula 4, L101 is a phenylene group.

In an exemplary embodiment of the present specification, in Formula 4, L102 is a direct bond.

In an exemplary embodiment of the present specification, in Formula 4, L102 is a phenylene group.

In an exemplary embodiment of the present specification, in Formula 4, L103 is a direct bond.

In an exemplary embodiment of the present specification, in Formula 4, L103 is a phenylene group.

In an exemplary embodiment of the present specification, in Formula 4, L104 is a direct bond.

In an exemplary embodiment of the present specification, in Formula 4, L104 is a phenylene group.

In an exemplary embodiment of the present specification, in Formula 4, L105 is a direct bond.

In an exemplary embodiment of the present specification, in Formula 4, L105 is a phenylene group.

In an exemplary embodiment of the present specification, in Formula 4, Ar101 to Ar103 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, in Formula 4, Ar101 is a substituted or unsubstituted C1-C30 alkyl group.

In an exemplary embodiment of the present specification, in Formula 4, Ar101 is a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group.

In the exemplary embodiment of the present specification, in Formula 4, Ar101 is a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.

In an exemplary embodiment of the present specification, in Formula 4, Ar101 is a methoxy group.

In an exemplary embodiment of the present specification, in Formula 4, Ar101 is an ethoxy group.

In an exemplary embodiment of the present specification, in Formula 4, Ar101 is an isopropoxy group.

In an exemplary embodiment of the present specification, in Formula 4, Ar101 is a tert-butoxy group.

In an exemplary embodiment of the present specification, in Formula 4, Ar101 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, in Formula 4, Ar101 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

In an exemplary embodiment of the present specification, in Formula 4, Ar101 is a phenyl group.

In an exemplary embodiment of the present specification, in Formula 4, Ar102 and Ar103 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, in Formula 4, Ar102 and Ar103 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group , a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted fluorenyl group.

In an exemplary embodiment of the present specification, in Formula 4, Ar102 is a phenyl group.

In an exemplary embodiment of the present specification, in Formula 4, Ar102 is a biphenyl group.

In an exemplary embodiment of the present specification, in Formula 4, Ar102 is a fluorenyl group substituted with an alkyl group.

In an exemplary embodiment of the present specification, in Formula 4, Ar102 is a fluorenyl group substituted with a methyl group.

In an exemplary embodiment of the present specification, in Formula 4, Ar103 is a phenyl group.

In an exemplary embodiment of the present specification, in Formula 4, Ar103 is a biphenyl group.

In an exemplary embodiment of the present specification, in Formula 4, Ar103 is a fluorenyl group substituted with an alkyl group.

In an exemplary embodiment of the present specification, in Formula 4, Ar103 is a fluorenyl group substituted with a methyl group.

In an exemplary embodiment of the present specification, in Formula 4, R201 to R205 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; hydroxyl group; nitrile group; 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.

In an exemplary embodiment of the present specification, in Formula 4, R201 to R205 are hydrogen.

In an exemplary embodiment of the present specification, in Formula 4, r104 and r105 are each an integer of 0 to 3, and when r104 and r105 are each 2 or more, two or more R104 and R105 are the same as or different from each other, respectively.

In an exemplary embodiment of the present specification, in Formula 4, m1 is a repeating number of units, and is an integer of 1 to 10,000.

In an exemplary embodiment of the present specification, the unit represented by Formula 4 may be represented by any one of the following structures.

In the structure,

m1 is the number of repetitions of the unit, and is an integer from 1 to 10,000.

In an exemplary embodiment of the present specification, the number average molecular weight of the polymer may be 5,000 g/mol to 1,000,000 g/mol. Specifically, it may be 5,000 g/mol to 300,000 g/mol.

In the present specification, molecular weight analysis was analyzed using GPC equipment. PL mixed Bx2 was used for the column, and tetrahydrofuran (THF) (filtered to 0.45 m) was used as the solvent. It was measured at a flow rate of 1.0 mL/min and a sample concentration of 1 mg/mL. 100 L of the sample was injected, and the column temperature was set to 40 °C. Agilent RI detector was used as the detector, and the standard was set with PS (polystyrene). Data processing was performed through the ChemStation program.

In the present specification, a coating composition comprising a compound represented by Formula 1, a coating composition comprising a compound represented by Formula 2 and Formula 3, and a coating comprising a polymer comprising a unit represented by Formula 4 The composition may further comprise a solvent.

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

In one embodiment of the present specification, the solvent is, for example, a chlorine-based solvent such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene; ether solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone solvents, such as acetone, methyl ethyl ketone, and cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyvalents such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol alcohols and derivatives thereof; alcohol solvents such as methanol, ethanol, propanol, isopropanol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents such as methyl benzoate, butyl benzoate and 3-phenoxy benzoate; A solvent such as tetralin is exemplified, but any solvent capable of dissolving or dispersing the compound according to an exemplary embodiment of the present specification is possible, and the present disclosure is not limited thereto.

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

In another exemplary embodiment, the boiling point of the solvent is preferably 40°C to 250°C, more preferably 60°C to 230°C, but is not limited thereto.

In another exemplary embodiment, 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 another embodiment, the concentration of the coating composition is preferably 0.1 wt/v% to 20 wt/v%, more preferably 0.5 wt/v% to 5 wt/v%, but is not limited thereto .

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

The thermal polymerization initiator is methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, methylcyclohexanone peroxide, cyclohexanone peroxide, isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide , bis-3,5,5-trimethyl hexanoyl peroxide, lauryl peroxide, benzoyl peroxide, p-chlorobenzoyl peroxide, dicumylperoxide, 2,5-dimethyl-2,5-(t-butyl Oxy)-hexane, 1,3-bis(t-butyl peroxy-isopropyl) benzene, t-butyl cumyl peroxide, di-tbutyl peroxide, 2,5-dimethyl-2,5-( dit-butyl peroxy) hexane-3, tris-(t-butyl peroxy) triazine, 1,1-dit-butyl peroxy-3,3,5-trimethyl cyclohexane, 1,1-dit -Butyl peroxycyclohexane, 2,2-di(t-butyl peroxy)butane, 4,4-di-t-butyrpaoxyvaleric acid n-butyl ester, 2,2-bis(4, 4-t-Butyl peroxy cyclohexyl) propane, t-butylperoxyisobutylate, dit-butyl peroxy hexahydro terephthalate, t-butyl peroxy-3,5,5-trimethylhexaate, t- peroxides such as butyl peroxybenzoate and dit-butyl peroxy trimethyl adipate, or azo-based compounds such as azobis isobutylnitrile, azobisdimethylvaleronitrile, and azobiscyclohexyl nitrile, but are not limited thereto. .

The photopolymerization initiator is diethoxy acetophenone, 2,2-dimethoxy-1,2-diphenyl ethan-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 4- (2-hydroxyethoxy) Phenyl-(2-hydroxy-2-propyl)ketone,2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone-1,2-hydroxy-2-methyl-1-phenyl Propan-1-one, 2-methyl-2-morpholino (4-methyl thiophenyl) propan-1-one, 1-phenyl-1,2-propanedione-2- (o-ethoxycarbonyl) oxime acetophenone-based or ketal-based photopolymerization initiators such as Photoinitiators, benzophenone-based photoinitiators such as benzophenone, 4-hydroxybenzophenone, 2-benzoylnaphthalene, 4-benzoyl biphenyl, 4-benzoylphenyl ether, acrylated benzophenone, and 1,4-benzoylbenzene, 2 -There are thioxanthone-based photopolymerization initiators such as isopropylthioxanthone, 2-chlorothioxanthone, 2,4-dimethyl thioxanthone, 2,4-diethylthioxanthone, and 2,4-dichlorothioxanthone. , Other photoinitiators include ethyl anthraquinone, 2,4,6-trimethylbenzoyl diphenyl phosphine oxide, 2,4,6-trimethylbenzoyl phenyl ethoxy phosphine oxide, bis(2,4,6-trimethylbenzoyl) Phenyl phosphine oxide, bis (2,4-dimethoxy benzoyl) -2,4,4-trimethyl pentyl phosphine oxide, methyl phenyl glyceryl ester, 9, 10-phenanthrene, acridine-based compound, tria ginsic compounds and imidazole-based compounds, but are not limited thereto.

Moreover, what has a photoinitiator effect can also be used individually or in combination with the said photoinitiator. For example, triethanolamine, methyl diethanolamine, 4-dimethylamino ethyl benzoate, 4-dimethylamino benzoate isoamyl, benzoate (2-dimethylamino) ethyl, 4,4'-dimethylaminobenzophenone, etc., but this It is not limited.

In an exemplary embodiment of the present invention, 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 an exemplary embodiment of the present invention, the cured product of the coating composition of the first organic material layer is in a state in which the coating composition is cured by heat treatment or light treatment.

In one embodiment of the present invention, the cured product of the coating composition of the second organic material layer is in a state in which the coating composition is cured by heat treatment or light treatment.

In an exemplary embodiment of the present invention, the second organic material layer is formed by baking a coating composition including a polymer including a unit represented by Formula 4 above.

In an exemplary embodiment of the present invention, the light emitting layer is formed by baking a coating composition including the compound represented by Formula 1 above.

In an exemplary embodiment of the present invention, the compound represented by Formula 2 and the compound represented by Formula 3 in the first organic layer are included in the coating composition in a weight ratio of 1:1 to 50:1.

In one embodiment of the present invention, the thickness of the light emitting layer is 100 Å to 500 Å.

In an exemplary embodiment of the present invention, the thickness of the first organic material layer is 100 Å to 1000 Å.

In an exemplary embodiment of the present invention, the thickness of the second organic material layer is 200 Å to 1000 Å.

In an exemplary embodiment of the present invention, the first organic material layer is a hole injection layer.

In an exemplary embodiment of the present invention, the second organic material layer is a hole transport layer.

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

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

In another exemplary embodiment, the organic light emitting device may be an 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 specification may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

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

In FIG. 1 , an organic light emitting device in which a first electrode 201 , a hole injection layer 301 , a hole transport layer 401 , a light emitting layer 501 , and a second electrode 601 are sequentially stacked on a substrate 101 . structure is illustrated.

In the exemplary embodiment of the present specification, the hole injection layer 301 of FIG. 1 includes a cured product of a coating composition including the compounds represented by Chemical Formulas 2 and 3, and the hole transport layer 401 is formed by Chemical Formula 4 Including a cured product of a coating composition including a polymer including a unit represented by, the light emitting layer 501 may be formed using a coating composition including the compound represented by the formula (1).

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

In an exemplary embodiment of the present invention, the method comprising: forming a first electrode on a substrate;

applying a coating composition comprising a compound of Formula 2 and a compound of Formula 3 on the first electrode;

forming a first organic material layer by curing the applied coating composition;

forming a second organic material layer by applying a coating composition comprising a polymer including a unit represented by the following Chemical Formula 4 on the first organic material layer;

It provides a method of manufacturing an organic light emitting device comprising the step of forming a light emitting layer by applying a coating composition comprising a compound represented by the following formula (1) on the second organic material layer.

[Formula 1]

In Formula 1,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L1 is a direct bond; Or a substituted or unsubstituted arylene group,

[Formula 2]

In Formula 2,

L11 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R11 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar11 and Ar12 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

X11 and X12 are the same as or different from each other, and each independently a photocurable group or a thermosetting group,

n11 and n14 are each independently an integer of 0 to 5,

n12 and n16 are each independently an integer of 0 to 4,

n13 and n15 are each independently an integer of 0 to 3,

When each of n11 to n16 is 2 or more, the substituents in parentheses are the same as or different from each other,

m11 and m12 are each 0 or 1,

[Formula 3]

In Formula 3,

At least one of R101 to R120 is F, a cyano group, or a substituted or unsubstituted fluoroalkyl group,

At least one of the remaining R101 to R120 is a curing group,

The remaining R101 to R120 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitro group; -C(O)R; -OR; -SR; -SO ₃ R; -COOR; -OC(O)R; -C(O)NRR'; a substituted or unsubstituted alkyl group; a substituted or unsubstituted fluoroalkyl 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 heteroaryl group,

R and R' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,

[Formula 4]

In Formula 4,

L101 to L105 are the same as or different from each other, and each independently a direct bond; -O-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; a substituted or unsubstituted divalent amine group; Or a substituted or unsubstituted heteroarylene group,

b101 is an integer from 1 to 10,

When b1 is 2 or more, two or more L101 are the same as or different from each other,

Ar101 to Ar103 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R201 to R205 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; hydroxyl group; nitrile group; 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,

r204 and r205 are each an integer of 0 to 3,

When r204 and r205 are each 2 or more, two or more R204 and R205 are the same as or different from each other,

m1 is the number of repetitions of the unit, and is an integer from 1 to 10,000.

In an exemplary embodiment of the present invention, the solvent of the coating composition including the compound represented by Formula 1 is selected from the group consisting of an aromatic solvent containing a ketone group, an ester group, or an ester group, and an aliphatic solvent.

In one embodiment of the present invention, the solvent of the coating composition comprising the compound represented by Formula 1 is 1-methylnaphthalene, dibenzyl ether, ethyl-4-methoxybenzoate (ethyl-4-methoxybenzoate), There are diethyl phthalate, diethylene monophenyl ether, isoamylbenzoate, and the like, and is not limited as long as the polymer including the unit represented by Chemical Formula 4 is not soluble in an organic solvent.

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

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

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

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

Specifically, in one embodiment of the present specification, the method comprising: preparing a substrate; forming a cathode or an anode on the substrate; forming one or more organic material layers on the cathode or anode; and forming an anode or a cathode on the organic material layer, wherein the forming of the organic material layer comprises the step of forming one or more organic material layers using the coating composition It provides a method of manufacturing an organic light emitting device do.

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

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

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

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

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

In one embodiment of the present specification, the time for heat-treating the organic material layer formed using the coating composition is preferably within 1 hour, more preferably within 30 minutes.

In an exemplary embodiment of the present specification, the atmosphere for heat-treating the organic material layer formed using the coating composition is preferably an inert gas such as argon or nitrogen.

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

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

In an exemplary embodiment of the present specification, the coating composition including the polymer may be mixed and dispersed in a polymer binder.

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

In addition, the polymer according to an exemplary embodiment of the present specification may be included alone as a compound in the organic layer, or may be included as a copolymer using a coating composition mixed with other monomers. In addition, a copolymer or a mixture may be included by using a coating composition mixed with other polymers.

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that may be used herein include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : a combination of a metal such as Sb and an oxide; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

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

The hole injection layer is a layer for injecting holes from the electrode, and when it includes an additional hole injection layer other than the hole injection layer including the coating composition of Chemical Formulas 2 and 3 according to an exemplary embodiment of the present specification, a hole injection material The furnace has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and prevents the movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material, and also , a compound excellent in the ability to form a thin film is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, 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, and an additional hole injection layer other than the hole injection layer including the polymer including the unit of Formula 4 according to an exemplary embodiment of the present specification. In the case of including, as the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

When an additional light emitting layer other than the light emitting layer comprising Formula 1 is included, the light emitting material is a material capable of emitting light in the visible ray region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively. However, a material having good quantum efficiency for phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene; Or rubrene, etc., but is not limited thereto.

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

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

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. do. Specific examples include Al complex of 8-hydroxyquinoline; complexes comprising Alq ₃ ; organic radical compounds; or a hydroxyflavone-metal complex, but is not limited thereto. The electron transport layer may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.

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

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

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

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

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

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

Preparation Example 1.

compound 1 compound 2 compound 3

Synthesis of 4-(2-bromo-9-hydroxy-9H-fluoren-9-yl)benzaldehyde (Compound 1): 1-bromo-4-(diethoxymethyl)benzene [1-bromo-4 -(diethyoxymethyl)benzene](30g, 115mmol) was dissolved in 250ml of tetrahydrofuran and lowered to -78℃. nBuLi (2.5M in hexane, 42ml, 105mol) was added and stirred at -78°C for 30 minutes. 2-Bromo-9H-fluoren-9-one [2-Bromo-9H-fluoren-9-one] (18.9 g, 73 mmol) was added at once and stirred overnight. After completion of the reaction with 1N HCl (aq), extraction was performed with ethyl acetate. The collected organic solution was dried using MgSO ₄ (magnesium sulfate) and filtered, and then the organic solvent was removed with a vacuum rotary concentrator. The residue was purified by column and recrystallized (toluene/hexane) to obtain 23 g (yield 87%) of Compound 1.

4-(2-bromo-9-phenyl-9H-fluoren-9-yl)benzaldehyde [4-(2-bromo-9-phenyl-9H-fluoren-9-yl)benzaldehyde] (Compound 2) Synthesis: 400 ml of benzene [benzene] was added to Compound 1 (11.5 g, 31.4 mmol), methane sulfonic acid (2.1 ml, 31.4 mmol) was added, and refluxed using a Dean-stark apparatus. . After neutralizing the acid with Sat'd NaHCO ₃ (aq), column purification was performed to obtain 6.5 g (yield 49%) of Compound 2.

Synthesis of 2-bromo-9-phenyl-9-(4-vinylphenyl)-9H-fluorene [2-bromo-9-phenyl-9-(4-vinylphenyl)-9H-fluorene] (Compound 3): Compound 2 (5.3 g, 12.3 mmol) and CH ₃ BrPPh ₃ (8.8 g, 24.7 mmol) were added to tetrahydrofuran [THF] and potassium tert-butoxide (2.77 g, 24.7 mmol) was added to 0. It was put at ℃ and stirred for 1 hour. The reaction was quenched with water and extracted with ethyl acetate (EA). MgSO ₄ (magnesium sulfate) was added to the collected organic solution, dried, filtered, and the organic solvent was removed with a vacuum rotary concentrator. The residue was purified by column to obtain 4.67 g of compound 3 (yield 89%).

Preparation Example 2.

compound 3 compound A

Synthesis of compound A: compound 3 (1.58 g, 3.74 mmol), N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine [N4,N4'-diphenyl-[1, 1'-biphenyl]-4,4'-diamine] (572 mg. 1.7 mmol), and sodium tert-butoxide] (980 mg, 10.2 mmol) was placed in a flask containing toluene [Toluene]. The flask containing the reactant was immersed in an oil bath at 90° C., and then Pd(PtBu ₃ ) ₂ (43 mg, 0.085 mmol) was added and returned for 1 hour. Water was added to stop the reaction, extraction was performed with dichloromethane [dichloromethane (DCM)], and the organic layer was dried with MgSO ₄ . After the organic solvent was removed using a vacuum rotary concentrator, the residue was purified by column to obtain 950 mg of Compound A (yield 55%, HPLC purity 99.5%). The NMR measurement values of Compound A are shown below.

¹ H NMR: δ 7.71 (d, 2H), 7.65 (d, 2H), 7.42 (d, 4H), 7.35 (d, 4H), 7.27 - 7.20 (m, 18H), 7.17 - 7.13 (m, 4H) , 7.11 - 7.06 (m, 14H), 7.03 (t, 2H), 6.70 - 6.64 (dd, 2H), 5.69 (d, 2H), 5.19 (d, 2H).

Preparation Example 3.

compound 3 compound B

Compound 3 (1.53 g, 3.61 mmol), N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine [N4,N4'-diphenyl-[1,1'-biphenyl] -4,4'-diamine] (801mg. 1.64mmol), and sodium tert-butoxide] (946mg, 9.84mmol) was placed in a flask containing toluene [Toluene]. After the flask containing the reactant was immersed in an oil bath at 90° C., Pd(PtBu ₃ ) ₂ (42 mg, 0.08 mmol) was added thereto and returned for 1 hour. Water was added to stop the reaction, extraction was performed with dichloromethane [dichloromethane (DCM)], and the organic layer was dried with MgSO ₄ . After removing the organic solvent using a vacuum rotary concentrator, the residue was purified by column to obtain 1.06 g (yield 55%, HPLC purity 99.4%) of Compound B. The NMR measurement values of Compound B are shown below.

¹ H NMR: δ 7.73 (d, 2H), 7.69 (d, 2H), 7.59 (d, 4H), 7.48 (t, 8H), 7.43 (t, 4H), 7.38 - 7.30 (m, 8H), 7.28 - 7.11 (m, 30H), 6.71 - 6.65 (dd, 2H), 5.69 (d, 2H), 5.20 (d, 2H).

Preparation Example 4.

compound 4

Mg (193 mg, 7.9208 mmol), I2 (4 mg), and tetrahydrofuran (THF) (10 mL) were added to a 100 mL round-bottom flask under a nitrogen atmosphere and stirred for 30 minutes. 4-Bromostyrene (1.04 mL, 7.9208 mmol) was added, and a water bath at 30 °C was placed under a round-bottom flask and stirred for one day. It was confirmed that the reaction solution became black and Mg was dissolved. The reaction solution was diluted by adding 5 mL of ether. Tris(pentafluorophenyl)borane (1 g, 3.9604 mmol) was dissolved in 5 mL of ether and slowly added to the reaction solution for 30 minutes. Agitate the solution for one day. Na2CO3 (0.1 M, 80 mL, 8.0mmol) is slowly added to the reaction solution. The organic solvent was extracted using ethyl acetate (EA) (20 mL x 3), and the residue was removed with MgSO ₄ . In order to additionally remove residual water and impurities, it was distilled with benzene using Dean-stock. When about 10 mL of the solvent remained, the solution was cooled and filtered to obtain 1.6 g of Compound 4. (Yield: 64%)

Preparation 5.

compound 4 compound C

In a 25 mL round-bottom flask, add compound 4 sodium tris (perfluorophenyl) (4-vinylphenyl) borate (100 mg, 0.1567 mmol), distilled water 10 mL, Ph ₂ ICl (60 mg , 0.1881 mmol) for 1 hour stirred. When 15 mL of acetone was added to the reaction solution, a precipitate was formed, and the precipitate was filtered and dried to obtain 140 mg of Compound C. (Yield: 100%)

Preparation 6.

compound 5

After dissolving 3-bromo-9-phenyl-9H-carbazole (9 g, 27.9 mmol) and 4-formylbenzene boronic acid (4.18 g, 27.9 mmol) in anhydrous tetrahydrofuran (THF, 100 mL), Pd (PPh ₃ ) ₄ (0.32 g, 0.28 mmol) and 70 ml of a 2M aqueous potassium carbonate (K ₂ CO ₃ /H ₂ 0) solution were added and refluxed for 6 hours. After the reaction solution was cooled to room temperature, the organic layer was extracted. The reaction solution was concentrated and recrystallized from ethyl alcohol (EtOH) to obtain compound 5 (8.9 g, yield 92%). MS: [M+H]+ = 348

Preparation 7.

compound 5 compound 6 compound 7

The compound 5 (8.2 g, 23.6 mmol) was dissolved in dimethylformaldehyde (200 mL), and N-bromosuccinimide (4.15 g, 23.6 mmol) was added thereto, followed by stirring at room temperature for 5 hours. After the reaction was terminated by adding distilled water to the reaction solution, the organic layer was extracted. The reaction solution was concentrated and recrystallized from ethyl alcohol (EtOH) to obtain compound 6 (8.25 g, yield 82%). MS: [M+H]+ = 427

Methyltriphenylphosphonium bromide salt (13.41g, 37.532mmol) and potassium t-butoxide (4.21g, 37.532mmol) were put in anhydrous tetrahydrofuran (300ml) and stirred first did. Then, compound 6 (8 g, 18.766 mmol) dissolved in anhydrous tetrahydrofuran (60 ml) was slowly added dropwise, followed by reaction for 5 hours. After the reaction was terminated with an aqueous sodium carbonate solution, the organic layer was extracted using methylene chloride and water, and the residual moisture was removed using MgSO ₄ . After the reaction solution was concentrated, column chromatography was performed using methylene chloride and hexane to obtain compound 7 (7.8 g, 98%). MS: [M+H]+ =425

Preparation 8.

compound 7 compound 8

Compound 7 (3.65 g, 8.615 mmol), (4-(diphenylamino)phenyl)boronic acid (2.99 g, 10.338 mmol), Pd(PPh3)4 (498 mg, 0.431 mmol) and K ₂ CO ₃ (3.57 g, 25.845 mmol) ) was dissolved in anhydrous tetrahydrofuran (200ml) and distilled water (100ml), followed by stirring at 70°C for 15 hours. The organic layer was extracted using ethyl acetate and water. After removing water using MgSO ₄ , the solvent was removed under reduced pressure. Compound 8 was isolated and purified by column chromatography on the obtained material using ethyl acetate and hexane. MS: [M+H]+ = 589

Preparation 9.

compound 8 compound D

Compound 8 (500 mg) and AIBN (1.2 mg) were added to toluene, and reacted at 100° C. for 14 hours under nitrogen substitution. Compound D prepared by precipitation in ethyl acetate was prepared. Mn=16,300 Mw=29,400

Preparation 10.

compound 7 compound 9

Compound 7 (3.65 g, 8.615 mmol), diphenylamine (1.74 g, 10.338 mmol), Pd(tBu ₃ P) ₂ (220 mg, 0.431 mmol) and sodium t-Butoxide (2.48 g, 25.845 mmol) It was dissolved in toluene (26ml) and stirred at 100°C for 15 hours. The organic layer was extracted using ethyl acetate and water. After removing water using MgSO ₄ , the solvent was removed under reduced pressure. Compound 9 was isolated and purified by column chromatography on the obtained material using ethyl acetate and hexane. [M+H]+=513

Preparation 11.

compound 9 compound E

Compound E was prepared in the same manner as in the preparation of Compound C, except that Compound 9 was used instead of Compound 8. Mn=104,000 Mw=225,000

Preparation 12.

compound F

9-Bromo-10-(naphthalen-1-yl)anthracene (1.92g, 5mmol), ((3-(naphthalen-2-yl)phenyl)boronic acid (1.86g, 7.5mmol), Pd(PPh3)4 (0.58g, 0.5mmol) and K2CO3 (2.07g, 15mmol) were dissolved in toluene (60ml) and distilled water (20ml) and stirred for 15 hours at 90° C. After separating the organic layer, it was dried with MgSO ₄ After removal, the solvent was removed under reduced pressure.The obtained material was subjected to column chromatography using dichloromethane and hexane to separate and purify compound F. MS: [M+H]+ = 507

Preparation 13.

compound G

9-(4-bromophenyl)-10-(naphthalen-1-yl)anthracene (2.3 g, 5 mmol) was used in place of 9-bromo-10-(naphthalen-1-yl)anthracene. Compound G was prepared in the same manner as for preparing compound E. MS: [M+H]+ = 583

Experimental example .

Preparation of ITO substrate

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,500 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water.

After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol and acetone and dried. After washing the substrate for 5 minutes, the substrate was transported to a glove box.

Example 1

On the ITO transparent electrode, 1.5wt% toluene ink containing compound A and compound C in a weight ratio of 8:2 was spin-coated on the ITO surface and heat-treated (cured) at 220°C for 30 minutes to form a hole injection layer to a thickness of 30nm did. A 2wt% toluene ink of Compound D was spin-coated on the hole injection layer formed above, and baked at 190° C. for 1 hour to form a hole transport layer to a thickness of 40 nm. A 2wt% cyclohexanone solution was prepared in 95:5 parts by weight of compound F and the following compound H on the hole transport layer, spin-coated at 5000rpm, baked at 80°C for 2 minutes, and baked at 120°C for 30 minutes. ) to form a light emitting layer with a thickness of 55 nm. After drying this at 130° C. for 10 minutes in a nitrogen gas atmosphere, lithium fluoride (LiF) was deposited to a thickness of about 1 nm, and finally aluminum was deposited to a thickness of 100 nm to form a cathode. In the above process, the lithium fluoride of the negative electrode maintained a deposition rate of 0.3 Å/sec and aluminum 2 Å/sec, and the vacuum degree during deposition was maintained at 2 X 10 ^-7 to 5 X 10 ^-6 torr, an organic light emitting device was manufactured. .

Example 2

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

Example 3

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

Example 4

An organic light emitting diode was manufactured in the same manner as in Example 2, except that Compound G was used instead of Compound F in the manufacturing process of Example 2.

Example 5

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

Example 6

An organic light emitting diode was manufactured in the same manner as in Example 5, except that Compound B was used instead of Compound A in the manufacturing process of Example 5.

Example 7

An organic light emitting diode was manufactured in the same manner as in Example 5, except that Compound G was used instead of Compound F in the manufacturing process of Example 5.

Example 8

An organic light emitting diode was manufactured in the same manner as in Example 7, except that Compound B was used instead of Compound A in the manufacturing process of Example 7.

Comparative Example 1

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

Comparative Example 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Comparative Compound 2 was used instead of Compound C in the manufacturing process of Example 1.

Comparative Example 3

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Comparative Compound 3 was used instead of Compound D in the manufacturing process of Example 1.

Driving voltage, current efficiency, and quantum efficiency values were measured for the organic light emitting devices prepared in Examples 1 to 8 and Comparative Examples 1 to 3 at a current density of 10 mA/cm ² , and compared to initial luminance at a current density of 10 mA/cm ² The time to be 95% was measured, and the results are shown in Table 1 below.

Voltage
(V) power efficiency
(lm/W) luminous efficiency
(cd/A) quantum efficiency
(%) life span
(hr) Example 1 4.09 3.20 4.16 5.62 89.5 Example 2 3.82 4.37 5.31 5.69 91.3 Example 3 4.10 3.20 4.18 5.60 78.5 Example 4 3.90 4.35 5.39 5.74 81.3 Example 5 4.10 4.82 6.28 6.79 98.8 Example 6 3.89 4.26 5.28 5.65 100.5 Example 7 3.85 4.41 5.41 5.73 95.7 Example 8 4.14 4.82 6.35 6.88 93.5 Comparative Example 1 4.10 2.24 2.93 3.92 31.1 Comparative Example 2 3.82 0.29 0.35 0.38 2.1 Comparative Example 3 4.09 1.92 2.50 3.37 6.5

101: substrate
201: first electrode
301: first organic material layer
401: second organic material layer
501: light emitting layer
601: second electrode

Claims (13)

a first electrode;
a second electrode provided to face the first electrode;
a light emitting layer provided between the first electrode and the second electrode;
a second organic material layer provided between the first electrode and the light emitting layer; and
a first organic material layer provided between the first electrode and the second organic material layer;
The light emitting layer comprises a compound represented by the following formula (1),
The first organic layer includes a cured product of a coating composition comprising a compound of Formula 2 and a compound of Formula 3,
The second organic material layer comprises a polymer including a unit represented by the following formula (4),
The first organic material layer is an organic light emitting device comprising the compound of Formula 2 and the compound of Formula 3 in a weight ratio of 1:1 to 50:1:
[Formula 1]

In Formula 1,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L1 is a direct bond; Or a substituted or unsubstituted arylene group,
[Formula 2]

In Formula 2,
L11 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R11 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar11 and Ar12 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
X11 and X12 are the same as or different from each other, and each independently a photocurable group or a thermosetting group,
n11 and n14 are each independently an integer of 0 to 5,
n12 and n16 are each independently an integer of 0 to 4,
n13 and n15 are each independently an integer of 0 to 3,
When each of n11 to n16 is 2 or more, the substituents in parentheses are the same as or different from each other,
m11 and m12 are each 0 or 1,
[Formula 3]

In Formula 3,
At least one of R101 to R120 is F, a cyano group, or a substituted or unsubstituted fluoroalkyl group,
At least one of the remaining R101 to R120 is a curing group,
The remaining R101 to R120 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitro group; -C(O)R; -OR; -SR; -SO ₃ R; -COOR; -OC(O)R; -C(O)NRR'; a substituted or unsubstituted alkyl group; a substituted or unsubstituted fluoroalkyl 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 heteroaryl group,
R and R' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,
[Formula 4]

In Formula 4,
L101 to L105 are the same as or different from each other, and each independently a direct bond; -O-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; a substituted or unsubstituted divalent amine group; Or a substituted or unsubstituted heteroarylene group,
b101 is an integer from 1 to 10,
When b1 is 2 or more, two or more L101 are the same as or different from each other,
Ar101 to Ar103 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R201 to R205 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; hydroxyl group; nitrile group; 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,
r204 and r205 are each an integer of 0 to 3,
When r204 and r205 are each 2 or more, two or more R204 and R205 are the same as or different from each other,
m1 is the number of repetitions of the unit, and is an integer from 1 to 10,000. The organic light-emitting device according to claim 1, wherein in Formula 2, the photocurable group or the thermosetting group in the definitions of X1 and X2 has any one of the following structures:

. The organic light-emitting device of claim 1 , wherein in Formula 3, the curing group is any one of the following curing groups:
[hardener group]

In the curing group, L is a direct bond; O; S; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
k is an integer of 1 or 2, and when k is 2, the substituents in parentheses are the same as or different from each other,
R21 is a substituted or unsubstituted alkyl group. The organic light emitting diode of claim 1, wherein the polymer including the unit represented by Formula 4 has a number average molecular weight of 5,000 g/mol to 1,000,000 g/mol. The organic light-emitting device according to claim 1, wherein the cured product of the coating composition of the first organic material layer is in a state in which the coating composition is cured by heat treatment or light treatment. delete The organic light emitting diode of claim 1, wherein the light emitting layer has a thickness of 100 Å to 500 Å. The organic light emitting diode of claim 1, wherein the first organic material layer has a thickness of 100 Å to 1000 Å. The organic light emitting diode of claim 1, wherein the second organic material layer has a thickness of 100 Å to 1000 Å. The organic light emitting diode of claim 1, wherein the first organic material layer is a hole injection layer. The organic light emitting diode of claim 1, wherein the second organic material layer is a hole transport layer. forming a first electrode on a substrate;
applying a coating composition comprising a compound of Formula 2 and a compound of Formula 3 on the first electrode;
forming a first organic material layer by curing the applied coating composition;
forming a second organic material layer by applying a coating composition comprising a polymer including a unit represented by the following Chemical Formula 4 on the first organic material layer;
Forming a light emitting layer by applying a coating composition comprising a compound represented by the following formula (1) on the second organic layer,
The method of manufacturing an organic light emitting device, wherein the first organic material layer includes the compound of Formula 2 and the compound of Formula 3 in a weight ratio of 1:1 to 50:1:
[Formula 1]

In Formula 1,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L1 is a direct bond; Or a substituted or unsubstituted arylene group,
[Formula 2]

In Formula 2,
L11 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R11 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar11 and Ar12 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
X11 and X12 are the same as or different from each other, and each independently a photocurable group or a thermosetting group,
n11 and n14 are each independently an integer of 0 to 5,
n12 and n16 are each independently an integer of 0 to 4,
n13 and n15 are each independently an integer of 0 to 3,
When each of n11 to n16 is 2 or more, the substituents in parentheses are the same as or different from each other,
m11 and m12 are each 0 or 1,
[Formula 3]

In Formula 3,
At least one of R101 to R120 is F, a cyano group, or a substituted or unsubstituted fluoroalkyl group,
At least one of the remaining R101 to R120 is a curing group,
The remaining R101 to R120 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitro group; -C(O)R; -OR; -SR; -SO ₃ R; -COOR; -OC(O)R; -C(O)NRR'; a substituted or unsubstituted alkyl group; a substituted or unsubstituted fluoroalkyl 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 heteroaryl group,
R and R' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,
[Formula 4]

In Formula 4,
L101 to L105 are the same as or different from each other, and each independently a direct bond; -O-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; a substituted or unsubstituted divalent amine group; Or a substituted or unsubstituted heteroarylene group,
b101 is an integer from 1 to 10,
When b1 is 2 or more, two or more L101 are the same as or different from each other,
Ar101 to Ar103 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R201 to R205 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; hydroxyl group; nitrile group; 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,
r204 and r205 are each an integer of 1 to 3,
When r204 and r205 are each 2 or more, two or more R204 and R205 are the same as or different from each other,
m1 is the number of repetitions of the unit, and is an integer from 1 to 10,000. The method according to claim 12,
The solvent of the coating composition comprising the compound represented by Formula 1 is a method of manufacturing an organic light emitting device that is selected from the group consisting of an aromatic solvent comprising a ketone group, an ester group, or an ester group, and an aliphatic solvent.

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