KR102182177B1 - Carbazole derivatives and organic light emitting diode using the same - Google Patents

Abstract

The present specification relates to a carbazole derivative, a coating composition including the carbazole derivative, and an organic light emitting device formed using the coating composition.

Description

Carbazole derivatives and organic light emitting devices using the same TECHNICAL FIELD [CARBAZOLE DERIVATIVES AND ORGANIC LIGHT EMITTING DIODE USING THE SAME}

The present specification relates to a carbazole derivative, a coating composition including the carbazole derivative, and an organic light emitting device formed using the coating composition.

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

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

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

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

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

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

Therefore, in the technical field, the development of organic materials having the above requirements is required.

Korean Patent Publication No. 2012-0112277

The present specification is to provide a carbazole derivative that satisfies the above-described conditions usable in an organic light-emitting device and an organic light-emitting device including the same.

Z ⁺ X ^- or Z ^+. As a compound represented by X ^- , Z is a carbazole derivative represented by Formula 1 below, and may have a cationic or cationic radical form, wherein X ^- provides a compound with an anionic group.

[Formula 1]

In Formula 1,

Ar1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R1 to R6 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 cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted ester group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,

r1 is an integer from 1 to 5,

r2 is an integer from 1 to 3,

When r1 and r2 are each 2 or more, the structures in parentheses are the same or different from each other,

n is an integer of 1 or 2,

When n is 1, Ar2 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

When n is 2, Ar2 is a divalent substituted or unsubstituted alkyl group; A divalent substituted or unsubstituted cycloalkyl group; A divalent substituted or unsubstituted amine group; A divalent substituted or unsubstituted arylamine group; A divalent substituted or unsubstituted aryl group; Or a divalent substituted or unsubstituted heterocyclic group,

The R1 to R6, Ar1 and Ar2 may include a photocurable group or a thermosetting group.

In addition, the present specification provides a coating composition comprising the compound according to claims 1 to 8.

In addition, the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a cured product of the coating composition of claim 9 to provide.

The compound containing the carbazole derivative according to the exemplary embodiment of the present specification increases charge mobility and increases the number of charges, thereby acting as an efficient hole transporting material, and does not contain impurities such as cations of the existing electron-accepting material that have been modified or reduced. Therefore, it is possible to improve the performance, life and reproducibility of the electroluminescent device.

When the compound containing the carbazole derivative according to the exemplary embodiment of the present specification is used as a hole transporting material alone, batch to batch change according to the change in the ratio of the hole transporting compound and the electron accepting material as in the existing process You can solve the problem.

The compound containing a carbazole derivative according to an exemplary embodiment of the present specification contains a functional group that is polymerized by heat or light, so if sufficient heat or light is applied after film formation, resistance to the solvent for the next solution process occurs. Since the compound containing the carbazole derivative according to the exemplary embodiment of the specification is not washed away or the film properties are not changed, a reproducible organic light emitting device may be manufactured.

The compound including the carbazole derivative according to the exemplary embodiment of the present specification has high solubility in various organic solvents and may form a uniform film by using a solution in which the derivative is dissolved.

The organic material layer formed by using the compound containing the carbazole derivative according to the exemplary embodiment of the present specification has excellent thermal and optical stability after curing through heat and light and does not have solubility in other solvents, so that another solution on the film formation Through the process, a lamination film formation process may be performed.

The compound according to the exemplary embodiment of the present specification may be used as an organic material layer material of an organic light-emitting device, and may provide low driving voltage, high luminous efficiency, and high lifespan characteristics.

1 shows an example of an organic light-emitting device according to an exemplary embodiment of the present specification.
2 is a diagram showing an MS spectrum of Chemical Formula 3-31.
3 is a diagram showing an H ¹ -NMR spectrum of Chemical Formula 3-31.
4 is a diagram showing an MS spectrum of the cation and anion of Formula 3-29.
5 is a diagram showing an H1-NMR spectrum of Chemical Formula 3-29.
6 is a diagram showing an MS spectrum of the cations and anions of Formula 3-14.
7 is a diagram showing an H1-NMR spectrum of Chemical Formula 3-14.
8 is a diagram showing an MS spectrum of cations and anions of Formula 3-14 Mixture A.

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

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

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

In the entire specification of the present application, the term "combination of these" included in the expression of the Makushi format refers to one or more mixtures or combinations selected from the group consisting of the components described in the expression of the Makushi format, and the component It means to include one or more selected from the group consisting of

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

Meanwhile, the hole-transporting compound may use an inorganic material capable of a solution process, or an organic material having semiconductor characteristics. In the case of PEDOT:PSS, which is used as a hole-transporting compound in an organic light-emitting device manufactured by the current solution coating method, the LUMO energy level is lower than that of the organic material used as the light-emitting layer material. Is having difficulty. In addition to PEDOT:PSS, aryl amine derivatives are also widely used.

In particular, carbazole derivatives containing aryl amines are representative hole transporting compounds because of their relatively high hole transport rate and excellent electrical stability. Since carbazole derivatives contain amines, it is advantageous to generate and transport holes, and by introducing an appropriate number of carbazoles into the compound, the HOMO energy level can be adjusted to 5.0 to 5.3 eV suitable for the material for the hole injection layer.

However, when the hole transport layer is formed by using an aryl amine derivative alone, it does not have a sufficient number of charges and charge mobility, so an arbitrary amount of an electron-accepting compound is added to the hole transport compound to achieve the number of charges and charge mobility. And improves the performance and lifetime of organic light emitting devices.

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

In addition, the electron-accepting compound receives electrons from all or part of the host material and promotes conversion of the host material into cation or cation radicals, thereby helping to facilitate polymerization of the host material during heat treatment or light treatment after coating.

The electron accepting compound may have the following structure, but is not limited thereto.

The above structures are added together with an aryl amine derivative used as a hole-transporting compound to oxidize the hole-transporting compound to convert it into a cation or a cation radical, and the converted hole-transporting compound becomes a counter ion of an anion and exists as an ionic pair. The cation of the existing electron-accepting compound that has oxidized the transporting compound is modified or reduced to exist in the hole injection layer. The modified or reduced existing cations may act as impurities in the hole injection layer, and are preferably removed during the process, but it is difficult to remove the existing modified or reduced cations due to the process currently used. In fact, in the above structure, 4-Isopropyl-4'-methyldiphenyliodonium Tetrakis (pentafluorophenyl) borate) lost 5% weight in TGA measurement. (weight loss) was observed at 235°C, so 4-Isopropyl-4'-methyldiphenyliodonium ion or a material modified from this ion is an electroluminescent device for general solution process It can be guessed that it remains in the hole injection layer during the manufacturing process.

In addition, the process known so far prepares a solution for the hole transport layer by mixing a hole-transporting compound and an electron-accepting material in a specific ratio, but the ratio of the two substances may vary depending on the batch when preparing the solution. The number of charges and charge mobility may vary, which may cause a problem of batch to batch change in the electroluminescent device.

In addition, the film coated with a solution prepared by mixing the hole transporting compound and the existing electron-accepting material has no solvent resistance to the next process solvent, so the electron-accepting material that could not be reacted by the solvent is washed away and the hole mobility decreases or the film characteristics There is a problem of deterioration of the device characteristics due to this deformation.

In order to solve this problem, development of a material having the properties of a hole-transporting compound and an electron-accepting compound is required.

Z ⁺ X ^- or Z ⁺ as described herein ^. The compound represented by X ^- has both hole-transporting properties and electron-accepting properties, so it is efficient because it does not require a process such as mixing two different materials, and the ratio that can occur when two different materials are mixed Change and further process problems can be prevented.

In the exemplary embodiment of the present specification, the compound containing the carbazole derivative represented by Formula 1 includes a polymerizable functional group, and thus, curing after film formation is possible.

In the present specification, the term "polymerizable functional group" may mean a reactive substituent that polymerizes between compounds by exposure to heat and/or light. The polymerization may be generated by heat treatment or light irradiation, and the carbon-carbon multiple bonds and radicals generated as the cyclic structure are decomposed are connected.

As in the exemplary embodiment of the present specification, in the case of a compound containing a polymerizable functional group, an organic light emitting device can be manufactured by a solution coating method, so that there is an economic effect in terms of time and cost.

In addition, since the carbazole derivative according to the 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 and hole transport material in an organic light emitting device.

In addition, by adjusting the substituent of the carbazole derivative of Formula 1 according to an exemplary embodiment of the present specification, an appropriate energy level and band gap can be finely adjusted, and interface characteristics between organic substances are improved, thereby lowering driving voltage and high light emission It is possible to provide an organic light emitting device having an efficiency.

In addition, the compound containing the carbazole derivative according to the exemplary embodiment of the present specification can finely adjust the energy level and the band gap by changing the anion, and improve the interfacial properties between organic substances, thereby reducing the driving voltage and high An organic light-emitting device having luminous efficiency can be provided.

In addition, the compound containing the carbazole derivative according to an exemplary embodiment of the present specification is introduced in the 3-position to the core structure, so it is advantageous for the generation and movement of holes.

In addition, the compound containing the carbazole derivative according to an exemplary embodiment of the present specification has two or more functional groups that cause polymerization, causing crosslinking during polymerization to extremely lower the solubility in various solvents, and thus including the present compound After the film formation process with a solution, an additional solution process is possible on the crosslinked film.

The compound containing the carbazole derivative according to the exemplary embodiment of the present specification has excellent thermal stability since the glass transition temperature (Tg) after crosslinking does not appear below 300°C, so it can induce improvement in driving stability and life characteristics of the device. have.

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

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

Means a site bonded to another substituent or a bonding portion.

In the present specification, the term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and 2 or more When substituted, two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to hydrogen; heavy hydrogen; Halogen group; Alkyl group; Cycloalkyl group; Silyl group; Alkoxy group; Alkenyl group; Ester group; Aryl group; Amine group; Arylamine group; And substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted with two or more substituents connected among the aforementioned substituents.

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, etc., but these Is not limited to

The alkyl group may be substituted with an aryl group or a heteroaryl group, and may 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 a heterocyclic group described below.

In the present specification, the length of the alkyl group does not affect the conjugation length of the compound, and may affect the application of the organic light emitting device of the compound, such as a vacuum deposition method or a solution coating method.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 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, and the like, but are not limited thereto. Does not.

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

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. May be, but is not limited thereto.

The alkoxy group may be substituted with an aryl group or a heteroaryl group, and may function as an aryloxy group or heteroaryloxy group. The aryl group and heterocyclic group may be selected from examples of an aryl group or a heterocyclic group described below.

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

The alkenyl group may be substituted with an aryl group or a heteroaryl group and may function as an arylalkenyl or heteroarylalkenyl group. The aryl group and heterocyclic group may be selected from examples of an aryl group or a heterocyclic group described below.

In the present specification, the number of carbon atoms of the ester group is not particularly limited, but it is preferably 1 to 50 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, 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 has 10 to 30 carbon atoms. 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 be bonded to each other to form a ring.

,

및

,

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

,

And

,

Etc. However, it is not limited thereto.

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

In the present specification, the heterocyclic group includes at least one atom or hetero atom other than carbon, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se, and S. The number of carbon atoms of the heterocyclic group is not particularly limited, but it is preferably 2 to 60 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group Group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are not limited thereto.

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

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

In the present specification, 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 containing 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 There are senylamine, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole, and triphenyl amine group, but are not limited thereto.

In the present specification, an 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.

In the present specification, a heteroarylene group refers to a heteroaryl group having two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aforementioned heteroaryl group may be applied.

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

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

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

In the present specification, the condensed structure may be a structure in which an aromatic carbon hydrogen ring is condensed with a corresponding substituent.

,

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.For example, as a condensed ring of benzimidazole

,

,

,

And the like, but is not limited thereto.

(spiro[fluorene-9,8'-indolo[3,2,1-de]acridine]) 등이 될 수 있으나, 이에 한정되는 것은 아니다.For example, as a condensed ring of acridine

(spiro[fluorene-9,8'-indolo[3,2,1-de]acridine]) or the like, but is not limited thereto.

In an exemplary embodiment of the present specification, Z ⁺ X ^- or Z ^+. Provides a compound represented by X ^- .

In the exemplary embodiment of the present specification, Z is a carbazole derivative represented by Formula 1 below, and may have a cationic or cationic radical form.

[Formula 1]

In the exemplary embodiment of the present specification, X ^- is an anionic group.

In the exemplary embodiment of the present specification, Ar1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group. , A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted pyrene group, or a substituted or unsubstituted fluorenyl group.

In the exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with an alkyl group or an aryl group.

In the exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with a methyl group, an ethyl group, a tert-butyl group, an isopropyl group, a phenyl group, a biphenyl group, or an alkenyl group.

In an exemplary embodiment of the present specification, Ar1 is a phenyl group.

In the exemplary embodiment of the present specification, Ar1 is a biphenyl group unsubstituted or substituted with a methyl group, an ethyl group, a tert-butyl group, an isopropyl group, a phenyl group, a biphenyl group, or an alkenyl group.

In an exemplary embodiment of the present specification, Ar1 is a biphenyl group.

In the exemplary embodiment of the present specification, Ar1 is a naphthyl group unsubstituted or substituted with a methyl group, ethyl group, tert-butyl group, isopropyl group, phenyl group, biphenyl group, or alkenyl group.

In an exemplary embodiment of the present specification, Ar1 is a naphthyl group.

In an exemplary embodiment of the present specification, Ar1 is a fluorenyl group unsubstituted or substituted with a methyl group, an ethyl group, a tert-butyl group, an isopropyl group, a phenyl group, a biphenyl group, or an alkenyl group.

In an exemplary embodiment of the present specification, Ar1 is a fluorenyl group.

In the exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted amine group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 is an amine group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, Ar1 is a phenyl group, a biphenyl group, or an amine group unsubstituted or substituted with styrene.

In the exemplary embodiment of the present specification, Ar1 is a diphenylarylamine group.

In an exemplary embodiment of the present specification, Ar1 is N-phenyl-4-vinylaniline.

In the exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylylene group, or a substituted or unsubstituted It is a fluorenylene group.

In the exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, or a phenylene group, a biphenylylene group, or a pulluorenylene group.

In the exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond or a phenylene group.

In an exemplary embodiment of the present specification, R1 to R6 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 cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted ester group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be bonded to each other with an adjacent group to form a substituted or unsubstituted ring.

In the exemplary embodiment of the present specification, R1 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

In an exemplary embodiment of the present specification, R1 is an aryl group in which an alkyl group, an alkoxy group, an alkenyl group, an aryl group, or a heterocyclic group is substituted or unsubstituted.

In the exemplary embodiment of the present specification, R1 is a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, an alkoxy group, an alkenyl group, an amine group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazole group. , A dibenzofuran group, or a phenyl group unsubstituted or substituted with a dibenzothiophene group.

In an exemplary embodiment of the present specification, R1 is a phenyl group.

In the exemplary embodiment of the present specification, R1 is a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, an alkoxy group, an alkenyl group, an amine group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazole group. , A dibenzofuran group, or a biphenyl group unsubstituted or substituted with a dibenzothiophene group.

In an exemplary embodiment of the present specification, R1 is a biphenyl group.

In the exemplary embodiment of the present specification, R1 is a substituted or unsubstituted silyl group.

In an exemplary embodiment of the present specification, R1 is a silyl group in which an alkyl group, an alkoxy group, an alkenyl group, or an aryl group is substituted or unsubstituted.

In an exemplary embodiment of the present specification, R1 is a silyl group.

In the exemplary embodiment of the present specification, R1 is a substituted or unsubstituted amine group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R1 is an amine group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, R1 is a phenyl group or an amine group unsubstituted or substituted with styrene.

In an exemplary embodiment of the present specification, R1 is a diphenylarylamine group.

In an exemplary embodiment of the present specification, R1 is N-phenyl-4-vinylaniline.

In the exemplary embodiment of the present specification, R4 is a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms.

In an exemplary embodiment of the present specification, R4 is an alkenyl group in which an alkyl group is substituted or unsubstituted.

In an exemplary embodiment of the present specification, R4 is an alkenyl group in which a methyl group or an ethyl group is substituted or unsubstituted.

In an exemplary embodiment of the present specification, R4 is an alkenyl group.

In an exemplary embodiment of the present specification, R4 is a substituted or unsubstituted alkoxy group.

In an exemplary embodiment of the present specification, R4 is an alkoxy group.

In an exemplary embodiment of the present specification, R4 is a substituted or unsubstituted ester group.

In an exemplary embodiment of the present specification, R4 is an ester group in which an alkenyl group is substituted or unsubstituted.

In an exemplary embodiment of the present specification, R4 is an ester group.

In the exemplary embodiment of the present specification, R4 is a substituted or unsubstituted silyl group.

In the exemplary embodiment of the present specification, R4 is a silyl group in which an alkyl group, an alkoxy group, an alkenyl group, or an aryl group is substituted or unsubstituted.

In an exemplary embodiment of the present specification, R4 is a silyl group.

In the exemplary embodiment of the present specification, R4 is a substituted or unsubstituted amine group having 6 to 50 carbon atoms.

In the exemplary embodiment of the present specification, R4 is an amine group unsubstituted or substituted with an aryl group or a heterocyclic group.

In the exemplary embodiment of the present specification, R4 is a phenyl group or an amine group unsubstituted or substituted with styrene.

In an exemplary embodiment of the present specification, R4 is a diphenylarylamine group.

In an exemplary embodiment of the present specification, R4 is N-phenyl-4-vinylaniline.

In the exemplary embodiment of the present specification, R4 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

In an exemplary embodiment of the present specification, R4 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group , A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted pyrene group, or a substituted or unsubstituted fluorenyl group.

In the exemplary embodiment of the present specification, R4 is a phenyl group unsubstituted or substituted with an alkyl group or an aryl group.

In the exemplary embodiment of the present specification, R4 is a phenyl group unsubstituted or substituted with a methyl group, an ethyl group, a tert-butyl group, an isopropyl group, a phenyl group, a biphenyl group, or an alkenyl group.

In an exemplary embodiment of the present specification, R4 is a phenyl group.

In the exemplary embodiment of the present specification, R4 is a biphenyl group unsubstituted or substituted with a methyl group, an ethyl group, a tert-butyl group, an isopropyl group, a phenyl group, a biphenyl group, or an alkenyl group.

In an exemplary embodiment of the present specification, R4 is a biphenyl group.

In an exemplary embodiment of the present specification, R4 is a naphthyl group unsubstituted or substituted with a methyl group, an ethyl group, a tert-butyl group, an isopropyl group, a phenyl group, a biphenyl group, or an alkenyl group.

In an exemplary embodiment of the present specification, R4 is a naphthyl group.

In the exemplary embodiment of the present specification, R4 is a fluorenyl group unsubstituted or substituted with a methyl group, an ethyl group, a tert-butyl group, an isopropyl group, a phenyl group, a biphenyl group, or an alkenyl group.

In an exemplary embodiment of the present specification, R4 is a fluorenyl group.

In the exemplary embodiment of the present specification, R4 is a substituted or unsubstituted heterocyclic group having 6 to 50 carbon atoms.

In an exemplary embodiment of the present specification, R4 is a substituted or unsubstituted thiophene group, a substituted or unsubstituted furan group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzofuran group, a substituted or unsubstituted A substituted carbazole group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, or a substituted or unsubstituted tria It is novelty.

In an exemplary embodiment of the present specification, R4 is a carbazole group in which an aryl group is substituted or unsubstituted.

In an exemplary embodiment of the present specification, R4 is a carbazole group in which a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group is substituted or unsubstituted.

In an exemplary embodiment of the present specification, R4 is a carbazole group.

In an exemplary embodiment of the present specification, R2, R3, R5 and R6 are hydrogen.

In the exemplary embodiment of the present specification, R5 and R6 may be bonded to each other to form a substituted or unsubstituted ring.

In the exemplary embodiment of the present specification, R5 and R6 may be bonded to each other to form a substituted or unsubstituted aromatic ring.

In an exemplary embodiment of the present specification, n is an integer of 1 or 2.

In the exemplary embodiment of the present specification, when n is 1, Ar2 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, when n is 1, Ar2 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

In the exemplary embodiment of the present specification, when n is 1, Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or It is an unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted pyrene group, or a substituted or unsubstituted fluorenyl group.

In an exemplary embodiment of the present specification, when n is 1, Ar2 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrene group, or a fluorenyl group.

In the exemplary embodiment of the present specification, when n is 1, Ar2 is a substituted or unsubstituted heterocyclic group having 6 to 50 carbon atoms.

In the exemplary embodiment of the present specification, when n is 1, Ar2 is a substituted or unsubstituted thiophene group, a substituted or unsubstituted furan group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzo. Furan group, substituted or unsubstituted carbazole group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted pyridine group, substituted or unsubstituted pyrimidine group, or It is a substituted or unsubstituted triazine group.

In the exemplary embodiment of the present specification, when n is 1, Ar2 is a carbazole group in which an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group is substituted or unsubstituted.

In the exemplary embodiment of the present specification, when n is 1, Ar2 is a carbazole group in which a phenyl group or an alkenyl group is substituted or unsubstituted.

In the exemplary embodiment of the present specification, when n is 1, Ar2 is a carbazole group.

In the exemplary embodiment of the present specification, when n is 2, Ar2 is a divalent substituted or unsubstituted alkyl group; A divalent substituted or unsubstituted cycloalkyl group; A divalent substituted or unsubstituted amine group; A divalent substituted or unsubstituted arylamine group; A divalent substituted or unsubstituted aryl group; Or a divalent substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, when n is 2, Ar2 is a substituted or unsubstituted aryl group.

In the exemplary embodiment of the present specification, when n is 2, Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or It is an unsubstituted phenanthryl group or a substituted or unsubstituted fluorenyl group.

In the exemplary embodiment of the present specification, when n is 2, Ar2 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, or a fluorenyl group.

In the exemplary embodiment of the present specification, when n is 2, Ar2 is a spirobifluorenyl group.

In the exemplary embodiment of the present specification, when n is 2, Ar2 is a substituted or unsubstituted amine group.

In the exemplary embodiment of the present specification, when n is 2, Ar2 is an amine group in which an aryl group is substituted or unsubstituted.

In the exemplary embodiment of the present specification, when n is 2, Ar2 is an amine group in which a phenyl group, a biphenyl group, or a fluorenyl group is substituted or unsubstituted.

In the exemplary embodiment of the present specification, when n is 2, Ar2 is an amine group.

In the exemplary embodiment of the present specification, when n is 2, Ar2 is a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, when n is 2, Ar2 is a substituted or unsubstituted thiophene group, a substituted or unsubstituted furan group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzo. Furan group, substituted or unsubstituted carbazole group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted pyridine group, substituted or unsubstituted pyrimidine group, or It is a substituted or unsubstituted triazine group.

In the exemplary embodiment of the present specification, when n is 2, Ar2 is a carbazole group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, when n is 2, Ar2 is a carbazole group.

In the exemplary embodiment of the present specification, R1 to R6, Ar1, and Ar2 may include a photocurable group or a thermosetting group.

In the exemplary embodiment of the present specification, at least one of R1 to R6, Ar1 and Ar2 may include a photocurable group or a thermosetting group.

In an exemplary embodiment of the present specification, at least one of R3 to R6 may include a photocurable group or a thermosetting group.

In the exemplary embodiment of the present specification, R4 may include a photocurable group or a thermosetting group.

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

In the above structure,

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

In the exemplary embodiment of the present specification, Z may be any one selected from Formulas 1-1 to 1-82 below.

In the exemplary embodiment of the present specification, X ^- may be represented by any one of the following Formulas [2-A] to [2-E].

[Formula 2-A]

[Formula 2-B]

[Formula 2-C]

[Formula 2-D]

[Formula 2-E]

In the above formulas [2-A] to [2-E],

G1 is oxygen, G2 is nitrogen, G3 is carbon, G4 is boron or potassium, G5 is phosphorus or antimony,

B1 to B6 are the same as or different from each other, and each independently a divalent substituted or unsubstituted arylene group, or a divalent substituted or unsubstituted heteroarylene group,

R11 to R25 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 alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted hydrocarbon ring by bonding of adjacent substituents to each other; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, X ^- may be any one selected from Formulas 2-1 to 2-18 below.

In an exemplary embodiment of the present specification, Z ⁺ X ^- or Z ^+. The compound represented by X ^- may be any one selected from Formulas 3-1 to 3-24 below.

In addition, the present specification is Z ⁺ X ^- or Z ^+. It provides a coating composition comprising the compound represented by X ^- .

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

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

In an exemplary embodiment of the present specification, the solvent is, for example, a chlorine-based solvent such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; Ether solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone solvents such as acetone, methyl ethyl ketone, 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, 1,2-hexanediol, etc. Alcohol and its derivatives; Alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; 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 invention is not sufficient, and these are not limited.

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

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

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

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

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

Examples of the thermal polymerization initiator include methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, methylcyclohexanone peroxide, cyclohexanone peroxide, isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide. Oxide, bis-3,5,5-trimethyl hexanoyl peroxide, lauryl peroxide, benzoyl peroxide, p-crole benzoyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-(t- Butyloxy)-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-di t-butyl peroxy cyclohexane, 2,2-di (t-butyl peroxy) butane, 4,4-di-t-butyric acid vareric acid n-butyl ester, 2,2-bis (4 ,4-t-butyl peroxy cyclohexyl)propane, t-butylperoxyisobutylate, dit-butyl peroxy hexahydro terephthalate, t-butyl peroxy-3,5,5-trimethylhexaate, t -There are peroxides such as butyl peroxybenzoate and dit-butyl peroxy trimethyl adipate, or azo systems such as azobis isobutyl nitrile, azobisdimethylvaleronitrile, and azobis cyclohexyl nitrile, but are not limited thereto .

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

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

In an exemplary embodiment of the present specification, the cathode; Anode; And at least one organic material layer provided between the cathode and the anode, and at least one of the organic material layers is formed using the coating composition.

In one embodiment of the present specification, the organic material layer formed by using the coating composition is a hole transport layer, a hole injection layer, or a layer that simultaneously transports and injects holes.

In another exemplary embodiment, the organic material layer formed by using the coating composition is a light emitting layer.

In another exemplary embodiment, the organic material layer formed by using the coating composition is an emission layer, and the emission layer includes the carbazole derivative as a host of the emission layer.

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

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

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

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

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

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

In FIG. 1, the hole injection layer 301, the hole transport layer 401, and the light-emitting layer 501 are formed using a coating composition containing a carbazole derivative represented by Chemical Formula 1.

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

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

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

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

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

Specifically, in the exemplary embodiment of the present specification, the step of preparing a substrate; Forming a cathode or an anode on the substrate; Forming one or more organic material layers on the cathode or anode; And forming an anode or a cathode on the organic material layer, wherein at least one layer of the organic material layer is formed using the coating composition.

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

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

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

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

In an exemplary embodiment of the present specification, the forming of the organic material layer formed by using the coating composition includes coating the coating composition on the cathode or anode; And heat treatment or light treatment of the coated coating composition.

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

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

In the case of including the heat treatment or light treatment step in the step of forming the organic material layer formed by using the coating composition, a plurality of carbazole derivatives included in the coating composition may form crosslinks to provide an organic material layer including a thinned structure. . In this case, it is possible to prevent dissolution, morphological influence, or decomposition by a 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 the heat treatment or light treatment step, the resistance to the solvent increases, so that the solution deposition and crosslinking method are repeatedly performed to form a multilayer, and the stability of the device is increased. It can increase the life characteristics.

In one embodiment of the present specification, the coating composition containing the compound may be a coating composition mixed and dispersed in a polymeric binder.

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

In addition, the compound according to an exemplary embodiment of the present specification may include a compound alone in the organic material layer by including a carbazole and an amine group, and a coating composition including the compound may be thinned through heat treatment or light treatment. It can be included as a copolymer by using a coating composition mixed with a monomer. In addition, a copolymer or a mixture may be included by using a coating composition mixed with another polymer.

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

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

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

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

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

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

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

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer.As an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer, and a material having high mobility for electrons is suitable. Do. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium and samarium, and in each case an aluminum layer or a silver layer follows.

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

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

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

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

In the exemplary embodiment of the present specification, the 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 described in detail in order to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various forms, and the scope of the present specification is not construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.

< Example >

Manufacturing example 1-1. Preparation of Formula 3-31

In a nitrogen atmosphere, 500 mL of dichloromethane was added to the formula A (5.00g, 6.10mmol) and stirred, and then silver hexafluoroantimonate (2.05g, 6.00mmol) was added, followed by stirring at room temperature for 20 hours. After passing through a pad of Celite, dichloromethane was removed in an evaporator, dissolved in dichloromethane (200 mL) and ethyl acetate (300 mL), and washed with water (400 mL). The organic layer was separated and concentrated with an evaporator. After vacuum drying, a black powder (5.29 g, yield 82%) was obtained.

Figure 2 is a diagram showing the MS spectrum of the cation and anion of Formula 3-31, Figure 3 is a diagram showing the H ¹ -NMR spectrum of the formula 3-31, a peak broadening phenomenon occurs in the Aromatic region, a radical or a radical cation It can be confirmed that it exists.

Manufacturing example 1-2. Preparation of Formula 3-29

In a nitrogen atmosphere, 500 mL of dichloromethane was added to Formula B (5.00 g, 7.54 mmol) and stirred, and then silver hexafluoroantimonate (2.48 g, 7.26 mmol) was added, followed by stirring at room temperature for 20 hours. After passing through a pad of Celite, dichloromethane was removed in an evaporator and dried in vacuum to obtain a dark green powder (6.30 g, yield 94%).

Figure 4 is a diagram showing the MS spectrum of the cation and anion of the formula 3-29, Figure 5 is a diagram showing the H ¹ -NMR spectrum of the formula 3-29, it is seen that the peak does not appear due to the peak broadening phenomenon in the Aromatic region It can be confirmed that a radical or a radical cation is present.

Manufacturing example 1-3. Preparation of Formula 3-14

In a nitrogen atmosphere, 500 mL of dichloromethane was added to Formula C (1000 mg, 0.978 mmol) and stirred, and then 4-isopropyl-4'-methyl diphenyl iodonium tetrakis (pentafluorophenyl) borate (1000 mg, 0.09840 mmol) was added. After adding and stirring at room temperature for 20 hours, the temperature was raised to 60°C, leaving about 100 mL of dichloromethane, evaporating to reflux, and stirring for 7 hours. After cooling to room temperature, hexane (75 mL) was added and stirred for 4 hours, and then a purple precipitate (790 mg, yield 95%) was obtained by filtration.

6 is a diagram showing the MS spectrum of the cations and anions of Chemical Formula 3-14, and FIG. 7 is a diagram showing the H ¹ -NMR spectrum of Chemical Formula 3-14. As a result of peak broadening in the Aromatic region, radicals or radicals It can be seen that cations are present.

Manufacturing example 1-4. Preparation of Formula 3-16

In a nitrogen atmosphere, 500 mL of dichloromethane was added to Formula E (500 mg, 0.574 mmol), stirred, and then 4-isopropyl-4'-methyl diphenyl iodonium tetrakis (pentafluorophenyl) borate (500 mg, 0.492 mmol) was added. After adding and stirring at room temperature for 20 hours, the temperature was raised to 60°C, leaving about 100 mL of dichloromethane, evaporating to reflux, and stirring for 7 hours. After cooling to room temperature, hexane (75 mL) was added and stirred for 4 hours, followed by filtration to give a purple precipitate (yield 89%).

Manufacturing example 1-5. Preparation of Formula 3-18

In a nitrogen atmosphere, 500 mL of dichloromethane was added to Formula F (500 mg, 0.574 mmol), stirred, and then 4-isopropyl-4'-methyl diphenyl iodonium tetrakis (pentafluorophenyl) borate (500 mg, 0.492 mmol) was added. After adding and stirring at room temperature for 20 hours, the temperature was raised to 60°C, leaving about 100 mL of dichloromethane, evaporating to reflux, and stirring for 7 hours. After cooling to room temperature, hexane (75 mL) was added and stirred for 4 hours, and then a purple precipitate (yield 90%) was obtained by filtration.

Manufacturing example 1-6. Preparation of Formula 3-20

In a nitrogen atmosphere, 500 mL of dichloromethane was added to Formula G (500 mg, 0.574 mmol) and stirred, and then 4-isopropyl-4'-methyl diphenyl iodonium tetrakis (pentafluorophenyl) borate (500 mg, 0.492 mmol) was added. After adding and stirring at room temperature for 20 hours, the temperature was raised to 60°C, leaving about 100 mL of dichloromethane, evaporating to reflux, and stirring for 7 hours. After cooling to room temperature, hexane (75 mL) was added and stirred for 4 hours, followed by filtration to give a purple precipitate (yield 94%).

Manufacturing example 1-7. Preparation of Formula 3-2

In a nitrogen atmosphere, 500 mL of dichloromethane was added to the formula H (0.399 mg, 0.574 mmol), stirred, and then 4-isopropyl-4'-methyl diphenyl iodonium tetrakis (pentafluorophenyl) borate (0.399 mg, 0.393 mmol) ) Was added and stirred at room temperature for 20 hours, and the temperature was raised to 60°C, leaving about 100 mL of dichloromethane, evaporating and refluxing, and stirring for another 7 hours. After cooling to room temperature, hexane (75 mL) was added and stirred for 4 hours, and then a purple precipitate (yield 88%) was obtained by filtration.

Manufacturing example 1-8. Formula 3-14 Mixture A

In a nitrogen atmosphere, 200 mL of dichloromethane was added to the formula C (800 mg, 0.40 mmol), stirred, and then 4-isopropyl-4'-methyl diphenyl iodonium tetrakis (pentafluorophenyl) borate (200 mg, 0.10 mmol) was added. Add. The temperature was raised to 60° C., stirred for 48 hours, cooled to room temperature, and concentrated by evaporation. After toluene (200 mL) was added and stirred for 2 hours, a purple precipitate (350 mg, yield 75%) was obtained by filtration.

8 is a diagram showing an MS spectrum of cations and anions of Formula 3-14 Mixture A.

Experimental example . Preparation of coating composition

The coating composition is, as described in Table 1 below, Formula 3-31, Formula 3-29, Formula 3-14, Formula 3-16, Formula 3-18, and Formulas prepared in Preparation Examples 1-1 to 1-9. 3-20, Chemical Formula 3-2, Chemical Formula 3-28, Chemical Formula 3-14 Mixture A and the following HAT_CN were dissolved alone in cyclohexanone at 1 wt/v% to prepare coating compositions 1 to 9.

[HAT-CN]

Coating composition Solids One Chemical Formula 3-31 2 Chemical Formula 3-29 3 Formula 3-14 4 Formula 3-16 5 Chemical Formula 3-18 6 Formula 3-20 7 Formula 3-2 8 Formula 3-14 Mixture A 9 HAT-CN

Example One

A glass substrate on which a thin film of ITO (indium tin oxide) was deposited to a thickness of 500Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water was finished, ultrasonic cleaning was performed with a solvent of isopropyl alcohol and acetone for 30 minutes each, followed by drying, and the substrate was transported to a glove box.

On the thus prepared ITO transparent electrode, the coating composition 1 described in Table 1 was spin-coated to a thickness of 300 Å, and the coating composition was cured at 230° C. for 30 minutes in a nitrogen atmosphere to form a hole injection layer. Thereafter, the following compound 1 was dissolved in toluene at 1 wt/v% on the hole injection layer and spin-coated to form a hole transport layer.

Subsequently, after being transferred to a vacuum evaporator, Compound 2 and Compound 3 were vacuum deposited on the hole transport layer to a thickness of 300 Å at a ratio of 0.92:0.08 to form a light emitting layer. Compound 4 was vacuum-deposited to a thickness of 200 Å on the emission layer to form an electron injection and transport layer. A cathode was formed by sequentially depositing LiF to a thickness of 12 Å and aluminum to a thickness of 2000 Å on the electron injection and transport layer.

Was the deposition rate of the organic material in the above process, maintaining the range of 0.4 to 0.7Å / sec, LiF of the cathode was 0.3Å / sec, aluminum was deposited at a rate of 2Å / sec, the degree of vacuum during the deposition to 2 x 10 ^-7 Maintained 5 x 10 ^-8 torr.

Thereafter, the sealing glass and the glass substrate were bonded to the glass using a photocurable epoxy resin to perform sealing, thereby producing an organic EL device having a multilayer structure. The subsequent operation was performed in air and at room temperature (25°C).

Example 2

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

Example 3

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

Example 4

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

Example 5

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

Example 6

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

Example 7

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

Example 8

An organic light-emitting device was manufactured in the same manner as in Example 1, except that coating composition 8 was used instead of coating composition 1 for the hole injection layer in Example 1.

Comparative example One

An organic light-emitting device was manufactured in the same manner as in Example 1, except that coating composition 9 was used instead of coating composition 1 for the hole injection layer in Example 1.

Table 2 shows the results of measuring the driving voltage and luminous efficiency at a current density of 10 mA/cm ² for the organic light emitting device manufactured by the above method.

Example Driving voltage (V) Current efficiency (cd/A) Power efficiency (lm/W) Life time
(95%,h) Example 1 6.29 2.18 1.16 0.5 Example 2 10.23 2.74 0.84 0.5 Example 3 5.98 2.73 1.46 24 Example 4 6.05 2.65 1.32 20 Example 5 6.30 2.22 1.13 23 Example 6 6.09 1.99 1.22 20 Example 7 7.66 1.41 1.21 14 Example 8 9.65 0.65 0.54 25 Comparative Example 1 11.05 0.51 0.26 30

As shown in Table 2, the carbazole derivative according to an exemplary embodiment of the present specification has excellent solubility in an organic solvent and is easy to prepare a coating composition, so that a uniform coating layer can be formed using the coating composition. have.

In addition, it can be seen that the compound containing the carbazole derivative represented by Chemical Formula 1 has a lower driving voltage, higher efficiency, and superior lifetime compared to Comparative Example 1.

Through the above, the preferred embodiment (hole transport layer) of the present specification has been described, but the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention. Belongs to the scope of the invention.

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

Claims (14)

Z ⁺ X ^- or Z ^+. As a compound represented by X ^- ,
Z is a carbazole derivative represented by the following Formula 1, and may have a cationic or cationic radical form,
The X ^- is a compound of the following formula 2-4 or 2-5:
[Formula 2-4]

[Formula 2-5]

[Formula 1]

In Formula 1,
Ar1 is an alkyl group; Biphenyl group; Naphthyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted carbazole group; Thermosetting machine; Or a photocurable group,
L1 to L3 are the same as or different from each other, and each independently a direct bond; Naphthylene group; Biphenylene group; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted divalent carbazole group,
R1 is hydrogen; Phenyl group; Carbazole; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted alkyl group; Thermosetting machine; Or a photocurable group,
R2 to R6 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted carbazole group; Thermosetting machine; Or a photocurable group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
r1 is an integer from 1 to 5,
r2 is an integer from 1 to 3,
When r1 and r2 are each 2 or more, the structures in parentheses are the same or different from each other,
n is an integer of 1 or 2,
When n is 1, Ar2 is hydrogen; Phenyl group; Biphenyl group; Naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted carbazole group; Thermosetting machine; Or a photocurable group,
When n is 2, Ar2 is a phenylene group; Biphenylene group; Divalent phenanthrene group; Naphthylene group; Binaphthylene group; A divalent substituted or unsubstituted fluorenyl group; A divalent substituted or unsubstituted amine group; A divalent substituted or unsubstituted arylamine group; Or a divalent substituted or unsubstituted carbazole group,
The substituted or unsubstituted alkyl group; Silyl group; Alkoxy group; Amine group; Ester group; Phenyl group; Heterocyclic group; One or more substituents selected from the group consisting of a thermosetting group and a photocurable group or two or more substituents are substituted or unsubstituted with a connected substituent,
The thermosetting group or photocurable group

or

ego,
In the above structure, R7 is hydrogen; Or an alkyl group. The compound of claim 1, wherein at least one of R1 to R6, Ar1 and Ar2 contains a photocurable group or a thermosetting group. The compound of claim 1, wherein at least one of R3 to R6 contains a photocurable group or a thermosetting group. The compound of claim 1, wherein R4 contains a photocurable group or a thermosetting group. delete The compound of claim 1, wherein Z is any one selected from Formulas 1-1 to 1-82:

delete The method according to claim 1, Z ⁺ X ^- or Z ^+. The compound represented by X ^- is any one selected from the following Formulas 3-1 to 3-24:

A coating composition comprising the compound according to any one of claims 1 to 4, 6 and 8. The method of claim 9,
The coating composition is a coating composition for an organic light emitting device. A first electrode;
A second electrode provided to face the first electrode; And
It includes at least one organic material layer provided between the first electrode and the second electrode,
At least one of the organic material layers is an organic light-emitting device comprising a cured product of the coating composition of claim 9. The organic light-emitting device of claim 11, wherein the cured product of the coating composition is cured by heat treatment or light treatment of the coating composition. The organic light-emitting device of claim 11, wherein the organic material layer including the cured product of the coating composition is a hole transport layer, a hole injection layer, or a layer that simultaneously transports and injects holes. The organic light emitting device of claim 11, wherein the organic material layer including the cured product of the coating composition is a light emitting layer.

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