KR102254298B1 - 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 using the same.

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 including a cured product of the coating composition.

The organic light emission phenomenon is an example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of the organic light emission phenomenon is as follows. When an organic 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 use, hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. It can be classified as

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 at the time of 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, and a material with high luminous efficiency that converts excitons into light when formed is preferred. desirable.

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

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

Second, it 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 organic light emitting devices 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, chemical stability, charge mobility, and interfacial properties with electrodes or adjacent layers should be excellent. For example, a material used in an 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 diode 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.

Recently, in order to reduce process cost, an organic light emitting device using a solution process, in particular an inkjet process, instead of a conventional deposition process has been developed. 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 in a solution process in the form of a regular structure, and the later process is the existing deposition process. A hybrid process utilizing the process is being studied. In addition, due to the problem of batch-to-batch and purity, studies on monomolecular materials other than polymeric materials are being conducted.

The charge transporter used as the hole injection layer uses an inorganic material or an organic material capable of a solution process. In this case, although it has semiconductor characteristics, the number of charges to generate and transport charges and charge mobility are insufficient. Therefore, it is necessary to add a positive electron-accepting compound or self-doping in order to improve the performance and lifetime of the organic light-emitting device.

On the other hand, the hole transport layer material is an arylamine-based material excellent in high hole movement speed and electrical stability. The hole transport layer organic monomolecular material must have a high hole moving speed and form an interface in contact with the light emitting layer, so the ionization potential moves in the light emitting layer with an appropriate value between the hole injection layer and the light emitting layer in order to suppress the generation of excitons at the hole transport layer-light emitting layer interface. It is necessary to have the ability to properly control the incoming electrons.

Korean Patent Laid-Open Publication No. 10-2012-0112277 Korean Patent Laid-Open Publication No. 10-2009-0042800

Room-Temperature Sol-Gel Derived Molybdenum Oxide Thin Films for Efficient and Stable Solution-Processed Organic Light-Emitting Diodes, ACS Appl. Mater. Interfaces, 2013, 5 (13), pp 6024-6029.

It is an object of the present specification to provide a carbazole derivative, a coating composition including the same, and an organic light emitting device including the same.

The present specification provides a carbazole derivative represented by the following formula (1).

[Formula 1]

In Formula 1,

Y1 is a thermosetting group; Or a photocurable group,

Y2 is a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Thermosetting machine; Or a photocurable group,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a is an integer from 0 to 5,

When a is 2 or more, 2 or more R2s are the same as or different from each other,

b is an integer from 0 to 7,

When b is 2 or more, 2 or more R1s are the same as or different from each other,

c is 1 or 2, provided that when c is 2, R2 is a substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,

When c is 2, the structures in parentheses are the same as or different from each other,

d is an integer from 0 to 5,

When d is 2 or more, 2 or more Y1s are the same as or different from each other.

In addition, the present specification provides a coating composition comprising the carbazole derivative.

In addition, the present specification is a cathode;

Anode; And

Including one or more organic material layers provided between the cathode and the anode,

At least one layer of the organic material layer includes a cured product of the coating composition,

The cured product of the coating composition provides an organic light-emitting device in which the coating composition is cured by heat treatment or light treatment.

The carbazole derivative according to an exemplary embodiment of the present specification is capable of a solution process, and thus a large area of the device is possible.

The carbazole derivative according to the exemplary embodiment of the present specification has high solubility in various organic solvents, and a uniform film formation may be formed using a solution in which the carbazole derivative is dissolved.

The carbazole derivative 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.

The organic material layer formed using the carbazole derivative according to an 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 the layered film is formed by another solution process on the film formation. The process can be carried out.

1 is a diagram showing a stacked structure 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 1-1.
3 is a diagram showing the DSC measurement result of Chemical Formula 1-1.
4 is a diagram showing an MS spectrum of Chemical Formula 1-1.
5 is a diagram showing the DSC measurement result of Chemical Formula 1-1.

Hereinafter, the present specification will be described in detail.

In the present specification, when a member is said to be positioned "on" another member, this includes not only the case where the member is in contact with the other 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.

An exemplary embodiment of the present specification provides a carbazole derivative represented by Chemical Formula 1.

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

In the present specification, the term "thermosetting group or photocurable group" may mean a reactive substituent for crosslinking between compounds by exposure to heat and or light. Crosslinking may be generated by heat treatment or light irradiation, as the carbon-carbon multiple bonds and cyclic structures are decomposed and the radicals generated are connected.

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

In the exemplary embodiment of the present specification, in the case of a carbazole derivative including a thermosetting group or a photocurable 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, in the case of forming a coating layer using a coating composition containing a carbazole derivative containing a thermosetting group or a photocurable group, since the thermosetting group or the photocurable group is crosslinked by heat or light, additional When the layers are stacked, the carbazole derivatives included in the coating composition are prevented from being washed away by the solvent, so that an additional layer can be stacked on the 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 the solvent is increased, and the film retention rate is high.

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

According to an exemplary embodiment of the present specification, in the case of a carbazole derivative crosslinked by heat treatment or light irradiation, since a plurality of carbazole derivatives are crosslinked and provided in the organic light emitting device in the form of a thin film, there is an effect of excellent thermal stability. Therefore, the organic light-emitting device using the carbazole derivative according to the exemplary embodiment of the present specification has excellent life characteristics.

In addition, since the carbazole derivative according to the exemplary embodiment of the present specification includes an amine structure, it may have an appropriate energy level and a band gap as a hole injection material, a hole transport material, or a light-emitting material in an organic light-emitting device. In addition, the carbazole derivative of Formula 1 according to an exemplary embodiment of the present specification can finely adjust an appropriate energy level and band gap by adjusting a substituent, and improves the interfacial properties between organic substances, thereby reducing driving voltage and high light emission. It is possible to provide an organic light emitting device having an efficiency.

In addition, since the carbazole derivative according to an exemplary embodiment of the present specification includes a phenyl amine structure, it has high solubility, and the thermosetting group or photocurable group connected to the phenyl amine has an effect of further improving the solubility.

According to the present specification, the carbazole derivative may include two or more thermosetting groups or photocurable groups. When two or more thermosetting groups or photocurable groups are included, crosslinking is induced during polymerization, thereby lowering solubility in various solvents. Therefore, after the film formation process using the coating composition containing the carbazole derivative, a solution process can be further performed on the crosslinked film.

In the carbazole derivative according to the exemplary embodiment of the present specification, the glass transition temperature (Tg) after crosslinking may not appear at 300°C or less. Therefore, it is excellent in thermal stability, and it is possible to induce improvement in driving stability and lifetime characteristics of the device.

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

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

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

The term "substituted" 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 where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are 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 deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amine group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; A substituted or unsubstituted silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine 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 above-exemplified substituents. For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent connected to two phenyl groups.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group 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, cyclopentylmethyl, cycloheptylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

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. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. 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.

In the present specification, the alkoxy group is not particularly limited, but is preferably 1 to 40 carbon atoms. According to an exemplary embodiment, the alkoxy group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkoxy group has 1 to 6 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, an isobutyloxy group, a sec-butyloxy group, a pentyloxy group, an iso-amyloxy group, and a hexyloxy group.

In the present specification, the amine group is an alkylamine group; Aralkylamine group; Heteroarylamine group; And an arylamine group.

In the present specification, the number of carbon atoms in the amine group is not particularly limited, but is preferably 1 to 30. 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, triphenylamine group, and the like, but are not limited thereto.

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

Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 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, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroarylamine group including two or more heterocyclic groups may include a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group at the same time.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. 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, a triphenylene group, and the like, but is not limited thereto.

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

,

,

, 및

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

,

,

, And

Can be, etc. However, it is not limited thereto.

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

In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as those of the aforementioned heteroaryl group.

In the present specification, the heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group.

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

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. 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.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with a C1-C25 linear, branched or cyclic alkyl group or an aryl group having 6 to 25 carbon atoms in the oxygen of the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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

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

In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphine 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.

In the present specification, the aryl group in the aryloxy group, arylthioxy group, arylsulfoxy group, arylphosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group, arylamine group, and arylheteroarylamine group is described above. A description of an aryl group may apply.

In the present specification, among the alkyl thioxy group, alkyl sulfoxy group, aralkyl group, aralkylamine group, alkylaryl group, and alkylamine group, the above description of the alkyl group may be applied.

In the present specification, the heteroaryl group among the heteroaryl group, the heteroarylamine group, and the arylheteroarylamine group may be described above with respect to the heterocyclic group.

In the present specification, the alkenyl group among the aralkenyl groups may be described above with respect to the alkenyl group.

In the present specification, the "adjacent" group refers to a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, or a substituent located three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. can do. For example, two substituents substituted with an ortho position in a benzene ring and two substituents substituted with the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other. Alternatively, two substituents of carbon 9 in fluorene may be interpreted as "adjacent" to each other.

In the present specification, in a substituted or unsubstituted ring formed by bonding of adjacent groups to each other, "ring" refers to a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.

The hydrocarbon ring may be selected from examples of the cycloalkyl group or an aryl group.

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

[Formula 2]

[Formula 3]

In Formula 2 or 3,

Y1, Y2, R1, R2, a, b and d are the same as the definition in Formula 1,

Y3 is a thermosetting group; Or a photocurable group,

Y4 is a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Thermosetting machine; Or a photocurable group,

b'is an integer from 0 to 6,

When b'is 2 or more, 2 or more R1s are the same as or different from each other,

e is an integer from 0 to 5,

When e is 2 or more, 2 or more Y3s are the same as or different from each other.

In an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by Chemical Formula 4 or 5.

[Formula 4]

[Formula 5]

In Formula 4 or 5,

Y1, Y2, R1, R2, a and d are the same as defined in Formula 1,

Y3 is a thermosetting group; Or a photocurable group,

Y4 is a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Thermosetting machine; Or a photocurable group,

e is an integer from 0 to 5,

When e is 2 or more, 2 or more Y3s are the same as or different from each other.

In an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; 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.

In an exemplary embodiment of the present specification, R1 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R1 is hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, R1 is hydrogen.

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

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

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

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

In the exemplary embodiment of the present specification, R1 is a phenyl group substituted with a heterocyclic group.

In the exemplary embodiment of the present specification, R1 is a phenyl group substituted with a carbazole group.

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

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

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

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

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

In the exemplary embodiment of the present specification, R1 is a carbazole group substituted with an aryl group.

In the exemplary embodiment of the present specification, R1 is a carbazole group substituted with a phenyl group.

In the exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; 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.

In the exemplary embodiment of the present specification, R2 is hydrogen; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, R2 is hydrogen.

In the exemplary embodiment of the present specification, R2 is a substituted or unsubstituted alkenyl group.

In the exemplary embodiment of the present specification, R2 is an unsubstituted alkenyl group.

In an exemplary embodiment of the present specification, R2 is an ethenyl group.

In the exemplary embodiment of the present specification, R2 is a substituted or unsubstituted amine group.

In the exemplary embodiment of the present specification, R2 is an amine group substituted with an aryl group.

In the exemplary embodiment of the present specification, R2 is an amine group substituted with a phenyl group.

In the exemplary embodiment of the present specification, R2 is an amine group substituted with a phenyl group substituted with an alkenyl group.

In the exemplary embodiment of the present specification, R2 is a diphenylamine group.

In the exemplary embodiment of the present specification, R2 is a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, R2 is a carbazole group.

In the exemplary embodiment of the present specification, the carbazole derivative represented by Formula 1 may be represented by any one of the following structural formulas.

In an exemplary embodiment of the present specification, it provides a coating composition comprising the above-described carbazole derivative.

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

In the exemplary embodiment of the present specification, the coating composition may further include one or two compounds selected from the group consisting of a compound and a polymer compound in which a thermosetting group or a photocurable group is introduced into a molecule.

In the exemplary embodiment of the present specification, the coating composition may further include a compound in which a thermosetting group or a photocurable group is introduced into the molecule. When the coating composition further includes a compound having a thermosetting group or a photocurable group introduced into the molecule, the degree of curing of the coating composition may be further increased.

In an exemplary embodiment of the present specification, the molecular weight of the compound into which a thermosetting group or a photocurable group is introduced is 100g/mol to 1,500g/mol.

In an exemplary embodiment of the present specification, the coating composition may further include a polymer compound. When the coating composition further includes a polymer compound, ink characteristics of the coating composition may be improved. That is, the coating composition further comprising the polymer compound may provide a viscosity suitable for coating or inkjet.

In one embodiment of the present specification, the viscosity of the coating composition is 2cP to 15cP. When it has a viscosity in the above range, it is easy to manufacture a device.

In an exemplary embodiment of the present specification, the molecular weight of the polymer compound is 10,000g/mol to 1,000,000g/mol.

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

In an exemplary embodiment of the present specification, the coating composition may be in a liquid state. The "liquid" refers to a liquid state at room temperature and pressure.

In the 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, cyclohexanone, isophorone, tetralone, decalone, and acetylacetone; Ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyvalents such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 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; It may be tetralin or the like. However, any solvent capable of dissolving or dispersing the carbazole derivative according to the exemplary embodiment of the present specification is sufficient, and is not limited thereto.

In one embodiment of the present specification, the boiling point of the solvent may be 40 ℃ to 250 ℃. Specifically, it may be between 60 ℃ and 230 ℃.

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

In an exemplary embodiment of the present specification, the viscosity of the single or mixed solvent may be 1cp to 10cp. Specifically, it may be 3 cp to 8 cp.

In the exemplary embodiment of the present specification, the concentration of the carbazole derivative in the coating composition may be 0.1wt/v% to 20wt/v%. Specifically, the concentration of the carbazole derivative in the coating composition may be 0.5wt/v% to 5wt/v%.

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.

As a thermal polymerization initiator, methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, methyl cyclohexanone peroxide, cyclohexanone peroxide, isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide , Bis-3,5,5-trimethyl hexanoyl peroxide, lauryl peroxide, benzoyl peroxide, p-crole benzoyl peroxide, dicumyl peroxide, 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 peroxy cyclohexane, 2,2-di (t-butyl peroxy) butane, 4,4-di-t-butyric acid valeric 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 systems such as azobis isobutyl nitrile, azobisdimethylvaleronitrile, and azobis cyclohexyl nitrile, but are not limited thereto. .

As a 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-methyl thiophenyl) propan-1-one, 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl) oxime Acetophenone-based or ketal-based photopolymerization initiators such as; Benzoin ether photopolymerization initiators such as benzoin, benzoin methylate, benzoin ethylate, benzoin isobylate, and benzoin isopropyrate; Benzophenone photopolymerization initiators such as benzophenone, 4-hydroxybenzophenone, 2-benzoyl naphthalene, 4-benzoyl biphenyl, 4-benzoyl phenyl ether, acrylated benzophenone, and 1,4-benzoyl benzene; Thioxanthone photopolymerization initiators, such as 2-isopropyl thioxanthone, 2-chloro thioxanthone, 2,4-dimethyl thioxanthone, 2,4-diethyl thioxanthone, and 2,4-dichloro thioxanthone; And 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-dimethoxybenzoyl)-2,4,4-trimethyl pentylphosphine oxide, methylphenirgryoxystel, 9,10-phenanthrene, acridine compound, triazine compound, imida And other photoinitiators such as sol-based compounds. 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. Not limited.

In the exemplary embodiment of the present specification, the coating composition may further include a p-doped material.

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

The p-doped material 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.

In the exemplary embodiment of the present specification, the p-doped material may be represented by any one of Formulas 11 to 14 below.

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

In Formulas 11 to 14,

A1 to A6 and A9 to A42 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Carbonyl group; Ester group; Amide group; A substituted or unsubstituted sulfonyl group (-SO ₂ R _a ); A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic group,

R _a is a substituted or unsubstituted aryl group,

A7 and A8 are the same as or different from each other, and each independently hydrogen; Nitrile group; -CF ₃ ; Or a substituted or unsubstituted ester group,

Y11 to Y15 are N.

In the present specification, A1 to A6 are the same as or different from each other, and each independently hydrogen; Nitrile group; Nitro group; Carbonyl group; Ester group; Amide group; A substituted or unsubstituted sulfonyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocycle, or combined with an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle.

In the present specification, A1 to A6 are the same as or different from each other, and each independently a nitrile group; Nitro group; A substituted or unsubstituted sulfonyl group; It is a substituted or unsubstituted alkenyl group or a substituted or unsubstituted aryl group.

In the present specification, each of A1 to A6 is a nitrile group.

In the present specification, each of A1 to A6 is a nitro group.

In the present specification, A1 to A6 are each a substituted or unsubstituted sulfonyl group.

In the present specification, each of A1 to A6 is a sulfonyl group substituted with an aryl group.

In the present specification, each of A1 to A6 is a sulfonyl group substituted with a phenyl group.

In the present specification, A1 to A6 are each a substituted or unsubstituted aryl group.

In the present specification, A1 to A6 are each a substituted or unsubstituted phenyl group.

In the present specification, each of A1 to A6 is a phenyl group substituted with a nitrile group.

In the present specification, each of A1 to A6 is a phenyl group substituted with a nitro group.

In the present specification, A1 to A6 are each a substituted or unsubstituted alkenyl group.

In the present specification, each of A1 to A6 is an alkenyl group substituted with a nitrile group.

In the present specification, Formula 11 may be represented by any one of the following structural formulas.

In the present specification, A9 to A12 are the same as or different from each other, and each independently hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic group.

In the present specification, A13 to A24 are the same as or different from each other, and each independently hydrogen; Halogen group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic group.

In the present specification, A13 and A14 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

In the present specification, A13 and A14 are bonded to each other to form a benzene ring.

In the present specification, A17 and A18 combine with each other to form a substituted or unsubstituted hydrocarbon ring.

In the present specification, A17 and A18 are bonded to each other to form a benzene ring.

In the present specification, A19 and A20 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

In the present specification, A19 and A20 are bonded to each other to form a benzene ring.

In the present specification, Formula 13 may be represented by Formula 13-1 or Formula 13-2 below.

[Chemical Formula 13-1]

[Chemical Formula 13-2]

In Formulas 13-1 and 13-2,

A13 to A18, A21 to A24 and Y15 are the same as defined in Formula 13,

A43 to A58 are the same as or different from each other, and each independently hydrogen; Halogen group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, A25 to A42 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents combine with each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, the p-doped material may be a conductive dopant.

In the exemplary embodiment of the present specification, the conductive dopant may be represented by any one of the following structural formulas.

In the present specification, the conductive dopant may mean a dopant that increases the conductivity of an organic material layer formed using a carbazole derivative.

In the exemplary embodiment of the present specification, the p-doped material may be a metal oxide. For example, it may be MoO ₂ (acac) ₃ or VO (acac) ₂ , but is not limited thereto.

In the present specification, the p-doped material is sufficient as long as it has a p-semiconductor property, and one or two or more types thereof may be used, and the type thereof is not limited.

In the exemplary embodiment of the present specification, the content of the p-doped material is 0 mol% to 80 mol% based on the carbazole derivative of Formula 1.

In an exemplary embodiment of the present specification, the cathode;

Anode; And

It includes at least one organic material layer provided between the cathode and the anode,

At least one of the organic material layers includes a cured product of the coating composition.

At this time, the cured product of the coating composition means a state in which the coating composition is cured by heat treatment or light treatment.

In one embodiment of the present specification, 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.

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

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

In FIG. 1, the hole injection layer 301, the hole transport layer 401, and the light emitting layer 501 may be formed using a coating composition including the carbazole derivative.

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

In another exemplary 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 using the coating composition may include coating the coating composition on the cathode or anode; And heat-treating or light-treating the coated coating composition.

In another exemplary embodiment, the heat treatment time in the heat treatment step may be within 1 hour. Specifically, it may be 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 atmosphere 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 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, when another layer is laminated on the surface of the organic material layer formed by using the coating composition, it is possible to prevent dissolution, morphological influence, or decomposition by a solvent.

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 methods are repeatedly performed to form a multilayer, and the stability of the device is increased. It can increase the life characteristics.

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

In the exemplary 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 a 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 carbazole derivative according to an exemplary embodiment of the present specification includes a carbazole and an amine group, so that the carbazole derivative alone may be included in the organic layer, and the coating composition including the carbazole derivative is thinned through heat treatment or light treatment. It may proceed, and may be included as a copolymer by using a coating composition mixed with other monomers. In addition, a coating composition mixed with another polymer may be used, and may be included as a copolymer or may be included as a mixture.

As the anode material, a material having a large work function is 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 SNO2: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 so that electrons can be easily injected 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 LiO2/Al, but are not limited thereto.

The hole injection material is a layer that injects holes from the electrode, and the hole injection material has the ability to transport holes, 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 in the light emitting layer. A compound that prevents the excitons from moving to the electron injection layer or the electron injection material and has excellent thin film formation ability 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.

As the light-emitting material, a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-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, and ladders. 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, periflanthene and the like 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 cyclic 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, and styryltetraamine, but are not limited thereto. In addition, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The electron transport material is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. The electron transport material is a material that can receive electrons from the cathode and transfer them to the emission layer. This is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq3; 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, it is cesium, barium, calcium, ytterbium and samarium, in each case followed 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, 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 is excellent in thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. 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-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 heterocyclic 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.

Manufacturing example 1. Preparation of Formula 1-1

Formula A (2g, 4.592mmol), N-phenyl-4-vinylaniline (1.97g, 15 22.96mmol), sodium tertbutoxdie (2.2g, 22.96mmol) toluene After dissolving in 50 mL of (toluene), the temperature was increased to 90°C. Bis (tri-tert-butylphosphine) palladium (0) (bis (tri-tert butylphosphine) palladium (0), 0.120 g) was dissolved in 10 mL of toluene and then reacted at 90° C. for 24 hours. The temperature was lowered, dissolved in methyl chloride (MC), and washed with water. The residual water was removed with magnesium sulfate (MgSO ₄ ), and the solvent was removed, followed by separation into a silica column (H/MC=3:1).

2 is a diagram showing an MS spectrum of Chemical Formula 1-1.

3 is a diagram showing the DSC measurement result of Chemical Formula 1-1.

Manufacturing example 2. Preparation of Formula 1-2

Formula B (1.98g, 4.592mmol), N-phenyl-4-vinylaniline (1.97g, 22.96mmol), sodium tertbutoxdie (2.2g, 22.96mmol) toluene After dissolving in 50 mL of (toluene), the temperature was increased to 90°C. Bis (tri-tert-butylphosphine) palladium (0) (bis (tri-tert-butylphosphine) palladium (0), 0.120 g) was dissolved in 10 mL of toluene and then reacted at 90° C. for 24 hours. The temperature was lowered, dissolved in methyl chloride (MC), and washed with water. The residual water was removed with magnesium sulfate (MgSO ₄ ), and the solvent was removed, followed by separation into a silica column (H/MC=3:1).

Manufacturing example 3. Preparation of Formula 1-3

Formula C (2.56 g, 7.22mmol), N-phenyl-4-vinylaniline (3.10g, 15.9mmol), sodium tertbutoxdie (3.46g, 36.1mmol) toluene After dissolving in (toluene) 70 mL, the temperature was increased to 90°C. Dissolve bis(tri-tert-butylphosphine)palladium(0)(bis(tri-tert-butylphosphine)palladium(0),0.180g) in 10 mL of toluene, and then reflux reaction at 110°C for 24 hours. Made it. The temperature was lowered, dissolved in methyl chloride (MC), and washed with water. The residual water was removed with magnesium sulfate (MgSO ₄ ), and the solvent was removed, followed by separation into a silica column (Toluene/Hexane=1/10).

4 is a diagram showing an MS spectrum of Chemical Formula 1-3.

5 is a diagram showing DSC measurement results of Chemical Formula 1-3.

Manufacturing example 4. Preparation of Formula 1-4

Formula D (3.36 g, 7.22mmol), N-phenyl-4-vinylaniline (3.10g, 15.9mmol), sodium tertbutoxdie (3.46g, 36.1mmol) toluene After dissolving in (toluene) 70 mL, the temperature was increased to 90°C. Bis (tri-tert-butylphosphine) palladium (0) (bis (tri-tert-butylphosphine) palladium (0), 0.180 g) was dissolved in 10 mL of toluene and added to a reflux reaction at 110°C for 24 hours. Made it. The temperature was lowered, dissolved in methyl chloride (MC), and washed with water. The residual water was removed with magnesium sulfate (MgSO ₄ ), and the solvent was removed, followed by separation into a silica column (Toluene/Hexane=1/10).

Manufacturing example 5. Preparation of Formula 1-5

Formula E (2.31 g, 7.22mmol), N-phenyl-4-vinylaniline (2.08g, 9.39mmol), sodium tertbutoxdie (3.46g, 36.1mmol) toluene After dissolving in (toluene) 70 mL, the temperature was increased to 90°C. Bis (tri-tert-butylphosphine) palladium (0) (bis (tri-tert-butylphosphine) palladium (0), 0.180 g) was dissolved in 10 mL of toluene and added to a reflux reaction at 110°C for 24 hours. Made it. The temperature was lowered, dissolved in methyl chloride (MC), and washed with water. The residual water was removed with magnesium sulfate (MgSO ₄ ), and the solvent was removed, followed by separation into a silica column (Toluene/Hexane=1/10).

Manufacturing example 6. Preparation of Formula 1-6

Formula F (2.31 g, 7.22mmol), N-phenyl-4-vinylaniline (2.08g, 9.39mmol), sodium tertbutoxdie (3.46g, 36.1mmol) toluene After dissolving in (toluene) 70 mL, the temperature was increased to 90°C. Bis (tri-tert-butylphosphine) palladium (0) (bis (tri-tert-butylphosphine) palladium (0), 0.180 g) was dissolved in 10 mL of toluene and added to a reflux reaction at 110°C for 24 hours. Made it. The temperature was lowered, dissolved in methyl chloride (MC), and washed with water. The residual water was removed with magnesium sulfate (MgSO ₄ ), the solvent was removed, and the silica column (Toluene/Hexane=1/10) was separated.

Manufacturing example 7. Preparation of Formula 1-7

Formula G (2.55 g, 7.22mmol), N-phenyl-4-vinylaniline (2.08g, 9.39mmol), sodium tertbutoxdie (3.46g, 36.1mmol) toluene After dissolving in (toluene) 70 mL, the temperature was increased to 90°C. Bis (tri-tert-butylphosphine) palladium (0) (bis (tri-tert-butylphosphine) palladium (0), 0.180 g) was dissolved in 10 mL of toluene and subjected to reflux reaction at 110° C. for 24 hours. The temperature was lowered, dissolved in methyl chloride (MC), and washed with water. The residual water was removed with magnesium sulfate (MgSO ₄ ), and the solvent was removed, followed by separation into a silica column (Toluene/Hexane=1/10).

Manufacturing example 8. Preparation of Formula 1-8

Formula H (3.76 g, 7.22mmol), N-phenyl-4-vinylaniline (2.08g, 9.39mmol), sodium tertbutoxdie (3.46g, 36.1mmol) toluene After dissolving in (toluene) 70 mL, the temperature was increased to 90°C. Bis (tri-tert-butylphosphine) palladium (0) (bis (tri-tert-butylphosphine) palladium (0), 0.180 g) was dissolved in 10 mL of toluene and subjected to reflux reaction at 110° C. for 24 hours. The temperature was lowered, dissolved in methyl chloride (MC), and washed with water. The residual water was removed with magnesium sulfate (MgSO ₄ ), and the solvent was removed, followed by separation into a silica column (Toluene/Hexane=1/10).

Experimental example 1. Preparation of coating composition

The coating composition is composed by dissolving Formula 1-1, Formula 1-2, Formula 2-1, and Formula 2-2 alone at 1 wt/v% as described in Table 1 below, or together with a dopant (TB, IB). The composition was dissolved by dissolving.

Coating composition Carbazole derivatives Dopant Carbazole derivative: weight ratio of dopant One Formula 1-1 - 1:0 2 Formula 1-3 - 1:0 3 Formula 1-1 TB 0.8:0.2 4 Formula 1-1 TB 0.98:0.02 5 Formula 1-1 IB 0.8:0.2 6 Formula 1-1 IB 0.98:0.02 7 Formula 1-3 TB 0.8:0.2 8 Formula 1-3 TB 0.98:0.02 9 Formula 1-3 IB 0.8:0.2 10 Formula 1-3 IB 0.98:0.02 11 Formula 2-1 - 1:0 12 Formula 2-2 - 1:0 13 Formula 2-1 TB 0.8:0.2 14 Formula 2-1 TB 0.98:0.02 15 Formula 2-1 IB 0.8:0.2 16 Formula 2-1 IB 0.98:0.02 17 Formula 2-2 TB 0.8:0.2 18 Formula 2-2 TB 0.98:0.02 19 Formula 2-2 IB 0.8:0.2 20 Formula 2-2 IB 0.98:0.02

Example One.

The glass substrate on which ITO (indium tin oxide) was deposited with a thickness of 1500Å 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, ultrasonic cleaning was performed with a solvent of isopropyl alcohol and acetone for 30 minutes each, and dried, and then the substrate was transported to a glove box.

On the thus prepared ITO transparent electrode, the coating composition 1 described in the following table was spin-coated to a thickness of 300 Å, and the coating composition was cured at 230° C. for 30 minutes in _{a nitrogen (N 2) atmosphere to form a hole injection layer.} Thereafter, after transferring to a vacuum evaporator, the following Compound 1 was vacuum deposited on the hole injection layer to form a hole transport layer.

Subsequently, compound 2 and compound 3 were vacuum-deposited at a concentration of 8% and a thickness of 300 Å on the hole transport layer to form a light emitting layer. The 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.

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

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 light emitting 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 coating composition 3 was used instead of coating composition 1 for the hole injection layer in Example 1 above.

Example 4.

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

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.

Example 9.

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.

Example 10.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that coating composition 10 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 11 was used instead of coating composition 1 for the hole injection layer in Example 1.

Comparative example 2.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that coating composition 12 was used instead of coating composition 1 for the hole injection layer in Example 1 above.

Comparative example 3.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that coating composition 13 was used instead of coating composition 1 for the hole injection layer in Example 1.

Comparative example 4.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that coating composition 14 was used instead of coating composition 1 for the hole injection layer in Example 1.

Comparative example 5.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that coating composition 15 was used instead of coating composition 1 for the hole injection layer in Example 1.

Comparative example 6.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that coating composition 16 was used instead of coating composition 1 for the hole injection layer in Example 1.

Comparative example 7.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that coating composition 17 was used instead of coating composition 1 for the hole injection layer in Example 1.

Comparative example 8.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that coating composition 18 was used instead of coating composition 1 for the hole injection layer in Example 1 above.

Comparative example 9.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that coating composition 19 was used instead of coating composition 1 for the hole injection layer in Example 1 above.

Comparative example 10.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that coating composition 20 was used instead of coating composition 1 for the hole injection layer in Example 1 above.

Example 11.

The glass substrate on which ITO (indium tin oxide) was deposited with a thickness of 1500Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform 10 ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol and acetone for 30 minutes each, and dried, and then the substrate was transported to a glove box.

PEDOT:PSS (AI4083) was spin-coated on the prepared ITO transparent electrode, coated to a thickness of 300 Å, and heat-treated at 180° C. for 30 minutes in an air atmosphere to form a hole injection layer. Thereafter, the coating composition 1 described in the above table was spin-coated to a thickness of 500 Å, and the coating composition was cured at 220° C. for 30 minutes in _{a nitrogen (N 2) atmosphere 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 concentration of 8% to form a light emitting layer. The 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.

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

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 light emitting device having a multilayer structure. The subsequent operation was performed in air and at room temperature (25°C).

Example 12.

An organic light-emitting device was manufactured in the same manner as in Example 11, except that coating composition 2 was used instead of coating composition 1 for the hole injection layer in Example 11.

Example 13.

An organic light-emitting device was manufactured in the same manner as in Example 11, except that coating composition 6 was used instead of coating composition 1 for the hole injection layer in Example 11.

Comparative example 11.

An organic light-emitting device was manufactured in the same manner as in Example 11, except that coating composition 11 was used instead of coating composition 1 for the hole injection layer in Example 11.

Comparative example 12.

An organic light-emitting device was manufactured in the same manner as in Example 11, except that coating composition 16 was used instead of coating composition 1 for the hole injection layer in Example 11.

Comparative example 13.

An organic light-emitting device was manufactured in the same manner as in Example 11, except that coating composition 20 was used instead of coating composition 1 for the hole injection layer in Example 1 above.

Example 14.

The glass substrate on which ITO (indium tin oxide) was deposited with a thickness of 1500Å 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, ultrasonic cleaning was performed with a solvent of isopropyl alcohol and acetone for 30 minutes each, and dried, and then the substrate was transported to a glove box.

The thus prepared coating composition 5 described in the above table was spin-coated to a thickness of 300 Å, and the coating composition was cured at 230° C. for 30 minutes in _{a nitrogen (N 2) atmosphere to form a hole injection layer.} Thereafter, the coating composition 1 described in the above table was spin-coated to a thickness of 500 Å, and the coating composition was cured at 220° C. for 30 minutes in _{a nitrogen (N 2) atmosphere to form a hole transport layer.}

Subsequently, compound 2 and compound 3 were vacuum-deposited at a concentration of 8% and a thickness of 300 Å on the hole transport layer to form a light emitting layer. The 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 0.4Å / sec to 0.7Å / sec, the cathode is LiF 0.3Å / sec, the deposition rate of aluminum was maintained 2Å / sec, the degree of vacuum upon deposition 2x10 ^{- 7} It was maintained at ⁸ torr ^- torr to 5x10.

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 15.

In Example 14, an organic light-emitting device was manufactured in the same manner as in Example 14, except that coating composition 9 was used instead of coating composition 5 for the hole injection layer, and coating composition 2 was used instead of coating composition 1 for the hole transport layer.

Example Driving voltage
(V) Current efficiency
(cd/A) Power efficiency
(1m/W) Life time
(95%, h) Example 1 11.2 0.85 0.77 0.6 Example 2 10.9 1.00 0.79 0.6 Example 3 5.6 2.36 1.37 88 Example 4 6.9 1.85 0.92 23 Example 5 5.5 2.55 1.33 84 Example 6 7.0 1.85 0.90 21 Example 7 5.4 3.66 1.98 180 Example 8 6.9 1.71 1.00 32 Example 9 5.2 3.82 2.05 175 Example 10 6.9 1.69 0.88 32 Example 11 5.7 3.34 1.74 55 Example 12 5.8 3.33 1.82 60 Example 13 5.1 3.90 2.30 201 Example 14 5.7 3.45 1.75 140 Example 15 5.7 3.40 1.72 141 Comparative Example 1 12.3 0.78 0.44 0.5 Comparative Example 2 12.6 0.64 0.51 0.5 Comparative Example 3 6.3 2.36 1.13 60. Comparative Example 4 7.5 1.84 0.89 20 Comparative Example 5 6.0 2.18 1.12 61 Comparative Example 6 7.6 1.88 0.95 21 Comparative Example 7 5.8 2.22 1.11 83 Comparative Example 8 7.7 1.62 1.01 19 Comparative Example 9 5.8 2.20 1.23 83 Comparative Example 10 7.8 1.69 1.21 17 Comparative Example 11 5.8 3.22 1.67 60 Comparative Example 12 5.1 3.85 2.10 190 Comparative Example 13 5.2 3.80 2.17 200

As a result of 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. .

In addition, when the formed coating layer is cured, the charge transporter is easily cured due to the addition of a curing group, and a layer that does not wash off the solvent can be formed. It was confirmed that it can be used as a material for a light emitting device.

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

Claims (12)

Carbazole derivatives represented by the following formula (5):
[Formula 5]

In Formula 5,
Y1 and Y3 are thermosetting or photocurable groups,
Y2 and Y4 are substituted or unsubstituted aryl groups; Thermosetting machine; Or a photocurable group,
R2 is a substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,
a is 1,
d is an integer from 0 to 5,
When d is 2 or more, 2 or more Y1s are the same as or different from each other,
e is an integer from 0 to 5,
When e is 2 or more, 2 or more Y3s are the same as or different from each other,
The thermosetting group or photocurable group

or

ego,
The substituted or unsubstituted is an amine group; Aryl group; Thermosetting machine; Or one or more substituents selected from the group consisting of a photocurable group or two or more substituents are substituted or unsubstituted with a connected substituent,
The carbazole derivative represented by Formula 5 includes two or more of the thermosetting group or photocurable group. delete delete delete delete delete The method according to claim 1,
The carbazole derivative is a carbazole derivative represented by any one of the following structural formulas:

A coating composition comprising the carbazole derivative according to claim 1 or 7. The method of claim 8,
The coating composition further comprises a p-doped material. Cathode;
Anode; And
Including one or more organic material layers provided between the cathode and the anode,
At least one layer of the organic material layer includes a cured product of the coating composition of claim 8,
The cured product of the coating composition is an organic light emitting device in a state obtained by curing the coating composition by heat treatment or light treatment. The method of claim 10,
The organic material layer including the cured product of the coating composition is an organic light emitting device comprising a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes. The method of claim 10,
An organic light-emitting device in which the organic material layer including the cured product of the coating composition includes a light-emitting layer.

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