TWI622582B - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

This specification relates to a heterocyclic compound and an organic light-emitting element containing the same.

Description

Heterocyclic compound and organic light-emitting element containing the same

This specification relates to a heterocyclic compound and an organic light-emitting element containing the same. The present application claims priority to and the benefit of the Korean Patent Application No. 10-2015-0077591, filed on Jan. 1, 2015, in the Korean Intellectual Property Office, the entire contents of which is incorporated herein by reference. in.

In general, organic luminescence refers to the phenomenon of converting electrical energy into light energy by using organic materials. An organic light-emitting element using an organic light-emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer interposed therebetween. Here, the organic material layer may have a multilayer structure composed of different materials to improve the efficiency and stability of the organic light emitting element in many cases, and may be, for example, a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer. , an electron injection layer and the like. In the structure of the organic light-emitting element, if a voltage is applied between the two electrodes, a hole is injected from the anode into the organic material layer and electrons are injected from the cathode into the organic material layer, and when the injected hole and the electron meet each other Excitons are formed and illuminate when the excitons fall again to the ground state.

There is a continuing need to develop novel materials for the aforementioned organic light-emitting elements.

[reference list] [Patent Literature]

International Publication No. 2003/012890

An object of the present specification is to provide a heterocyclic compound and an organic light-emitting element containing the same.

The present specification provides a heterocyclic compound represented by the following Chemical Formula 1.

In Chemical Formula 1, X1 to X3 are the same or different from each other, and are each independently N; or CR, X1 to X3 are not CR at the same time, and Ar1 is a substituent represented by the following Chemical Formula 2,

L is a direct bond, Ar2 and Ar3 are different from Ar1, and Ar2 and Ar3 are the same or different from each other, and are each independently a substituted or unsubstituted pentylene group having less than a penta ring; or a substituted or unsubstituted lower than a heterocyclic group of a pentacyclic ring, and R are the same or different from each other, and are each independently hydrogen; hydrazine; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

The present specification provides an organic light-emitting element comprising: a cathode; an anode; and one or more organic material layers disposed between the cathode and the anode, wherein one or more layers of the organic material layer comprise the above described Heterocyclic compound.

The heterocyclic compound according to the present specification can be used as a material for an organic material layer of an organic light-emitting element, and the organic light-emitting element containing the heterocyclic compound has characteristics of low driving voltage, high efficiency, and/or long service life.

1‧‧‧Substrate

2‧‧‧Anode

3‧‧‧Lighting layer

4‧‧‧ cathode

5‧‧‧ hole injection layer

6‧‧‧ hole transport layer

7‧‧‧Electronic transport layer

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

FIG. 2 illustrates an example of an organic light emitting element according to an exemplary embodiment of the present specification.

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

The present specification includes a heterocyclic compound represented by Chemical Formula 1.

Ar1 is a substituent represented by Chemical Formula 2.

In this specification, Means to connect to the part of Chemical Formula 1.

In the case where an exemplary embodiment according to the present specification includes a substituent represented by Chemical Formula 2, when a structure represented by Chemical Formula 2 and having a nonlinear structure is introduced, a wider optical band gap can be formed.

In this case, it is possible to reduce the influence of the energy barrier on the light-emitting layer by increasing the LUMO energy level of a material having a low HOMO energy level value such as a structure including X1 to X3 in Chemical Formula 1. In addition, in the case of including the substituent represented by Chemical Formula 2, the structure becomes close to an amorphous structure, making it possible to expect a low driving voltage and/or high efficiency in terms of the performance of the organic light emitting element.

In an exemplary embodiment of the present specification, the HOMO level of the heterocyclic compound represented by Chemical Formula 1 is from 5.8 eV to 6.7 eV.

In an exemplary embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 1 has a LUMO energy level of from 2.6 eV to 3.2 eV.

In the present invention, energy level means the magnitude of energy. Therefore, even when the energy level is expressed in the negative (-) direction from the vacuum level, it is interpreted that the energy level means the absolute value of the corresponding energy value. For example, the HOMO energy level means the distance from the vacuum level to the highest occupied molecular orbital. In addition, the LUMO energy level means the distance from the vacuum energy level to the lowest unoccupied molecular orbital domain.

In order to measure the HOMO energy level in this specification, UV photoelectron spectroscopy (UPS) can be used, in the film table. The surface is irradiated with ultraviolet light and the electrons that jump out in this case are detected to measure the ionization potential of the material. In addition, to measure the HOMO energy level, cyclic voltammetry (CV) can be used to dissolve the material to be measured and the electrolytic solution in a solvent, and then measure the oxidation potential via voltage scanning. Further, a method of photoemission yield spectrometer in air (PYSA) which is measured in the atmosphere by using an AC-3 machine (manufactured by RKI Instruments, Inc.) can be used. Ionization potential.

Specifically, the HOMO level of the present specification is achieved by vacuum depositing a target material on an ITO substrate to a thickness of 50 nm or more, and then using an AC-3 meter (manufactured by RKI Instruments Co., Ltd.). Measurement. In addition, for the LUMO energy level, the absorption spectrum (abs.) and the photoluminescence spectrum (PL) of the sample prepared above were measured, and then the energy of each spectral edge was calculated, and the difference was regarded as The band gap (Eg), and the LUMO energy level is calculated as a value obtained by subtracting the band gap difference by the HOMO energy level measured by AC-3.

In the present specification, the LUMO energy level can be obtained by measuring inverse photoelectron spectroscopy (IPES) or electrochemical reduction potential. IPES is a method of determining the LUMO energy level by irradiating an electron beam on a film and measuring the light emitted in this case. Further, to measure the electrochemical reduction potential, the measurement target material and the electrolytic solution are dissolved in a solvent, and then the reduction potential can be measured via voltage scanning. In addition, the LUMO energy level can be calculated by using the HOMO energy level and the singlet energy level obtained by measuring the degree of ultraviolet light absorption of the target material.

In an exemplary embodiment of the present specification, Ar1 is different from Ar2 and Ar3. Specifically, for Ar1, the compound may have an amorphous property due to the structure of the nonlinear triphenyl group represented by Chemical Formula 2. If it will be the same as Ar1 When the substituent is introduced into Ar2 and Ar3, the degree of crystallinity may increase due to the symmetrical structure. Therefore, in order to maximize the amorphousness, it is preferred that Ar1, Ar2, and Ar3 are different from each other.

In an exemplary embodiment of the present specification, the compound of the formula has a glass transition temperature (Tg) of from 120 ° C to 160 ° C, and preferably from 120 ° C to 140 ° C. When Ar2 or/and Ar3 is a biphenyl having the same structure as Ar1, the glass transition temperature (Tg) is lowered to 120 ° C or lower, and thus the stability of the compound is lowered.

In an exemplary embodiment of the present specification, Ar2 and Ar3 comprise an aryl group having less than a penta ring or a heterocyclic group lower than a penta ring. In an exemplary embodiment of the present specification, the molecular weight is increased to 750 g/m or more than 750 g/m by introducing a sub-five substituent into Ar2 and Ar3. In this case, sublimation purification can be promoted, and an increase in thermal stability at a high temperature can be expected.

In an exemplary embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 1 has a molecular weight of less than 900 g/mole. More preferably, the molecular weight of the heterocyclic compound represented by Chemical Formula 1 is less than 750 g/mole. In this case, sublimation purification can be promoted, and thermal stability at high temperatures can be increased.

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

In the present specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound becomes another substituent, and the position to be substituted is not limited as long as the position is a position at which a hydrogen atom is substituted. That is, a substituent may be substituted for a position, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" means that a group is taken by one or two or more substituents selected from the group consisting of: Generation: hydrogen; halogen group; nitrile group; nitro group; hydroxyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; An unsubstituted amino group; a substituted or unsubstituted aryl group; and a substituted or unsubstituted heterocyclic group, or a substituent exemplified above, linked to two or more than two substituents Substituents are substituted or have no substituents. For example, "substituents linked to two or more than two substituents" may be a biphenyl group. That is, the biphenyl group may also be an aryl group and may be interpreted as a substituent attached to two phenyl groups.

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 linear or branched alkyl group, and the number of carbon atoms thereof is not particularly limited, but is preferably from 1 to 50. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, t-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, third amyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl Benzyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl , n-octyl, trioctyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-decyl, 2,2-dimethylheptyl, 1-ethyl-propyl Base, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but the number of carbon atoms thereof is preferably from 3 to 60, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a 3-methylcyclopentyl group. , 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 alkoxy group may be a linear, branched or cyclic alkoxy group. base. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably from 1 to 20. Specific examples thereof include a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, an i-propyloxy group, a n-butoxy group, an isobutoxy group, and a third butoxy group. , second butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, N-decyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like, but are not limited thereto.

In the present specification, the alkenyl group may be a linear or branched alkenyl group, and the number of carbon atoms thereof is not particularly limited, but is preferably from 2 to 40. Specific examples thereof include a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, and a 3-pentene group. , 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, fluorenyl, styryl and the like, but are not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the aryl group is a phenyl group.

When the aryl group is a polycyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably from 10 to 24. Specific examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthryl group, an anthracenyl group, an anthracenyl group, a chrysenyl group, a fluorenyl group, and the like, but are not limited thereto.

In the present specification, polycyclic ring means that the number of condensed rings is 2 or more, and a single ring, that is, a ring in which a benzene ring is bonded by a single bond rather than a condensation, is not included in the polycyclic range. .

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

When the thiol group is substituted, the thiol group can be And similar groups. However, the base is not limited to this.

In the present specification, a heterocyclic group contains one or more atoms other than carbon, that is, a hetero atom, and specifically, a hetero atom may contain one or more atoms consisting of O, N, Se, S, and the like. The atoms selected from the group consisting of. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably from 2 to 60. Examples of heterocyclic groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, anthracene Pyridyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, pyridazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinoline Base, sulfhydryl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline A group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazine group, a dibenzofuranyl group, and the like, but is not limited thereto.

The heterocyclic group may be monocyclic or polycyclic, and may be an aromatic ring, an aliphatic ring or a condensed ring of an aromatic ring and an aliphatic ring.

In the present specification, the hydrocarbon ring may be an aliphatic ring, an aromatic ring, or a condensed ring of an aromatic ring and an aliphatic ring, and may be selected from the examples of a cycloalkyl group or an aryl group, but not a monovalent hydrocarbon ring. except. The heterocyclic ring may be an aliphatic ring, an aromatic ring or a condensed ring of an aromatic ring and an aliphatic ring, and may be selected from the examples of the heterocyclic group, except for the monovalent heterocyclic ring.

In the present specification, the meaning of monocyclic, bicyclic and pentacyclic rings is the number of condensed rings constituting the substituent, and the number of rings only connected by a single bond is not included in the number of rings. Inside. In particular, a phenyl substituted naphthyl group can be defined as a substituted bicyclic group rather than a tricyclic group.

In an exemplary embodiment of the present specification, L is a direct key.

When L of the present specification is a direct bond, the length of the conjugate bond can be further lowered as compared with the compound having a linking group at the L position, and thus the effect of appropriately transporting electrons and blocking holes can be obtained by having a wide band gap.

In an exemplary embodiment of the present specification, Ar 2 and Ar 3 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and less than a penta ring; or substituted Or unsubstituted heterocyclic group having less than pentacyclic ring of 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar 2 and Ar 3 are the same or different from each other, and are each independently a pentylene group having 6 to 30 carbon atoms, which is unsubstituted or subjected to one Or two or more substituents selected from the group consisting of hydrazine, cyano, alkyl, aryl and heterocyclic groups; or a heterocyclic ring having less than five rings having from 2 to 30 carbon atoms A group wherein the heterocyclic group is unsubstituted or substituted with one or two or more than two substituents selected from the group consisting of hydrazine, cyano, alkyl, aryl and heterocyclic groups.

In an exemplary embodiment of the present specification, Ar2 and Ar3 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having a lower than penta ring having 6 to 30 carbon atoms.

In another exemplary embodiment, Ar2 and Ar3 are the same or different from each other, and are each independently a substituted or unsubstituted heterocyclic group having less than pentacyclic groups of 2 to 30 carbon atoms.

In still another exemplary embodiment, Ar2 and Ar3 are the same or different from each other, And each independently is a substituted or unsubstituted heterocyclic group having less than pentacyclic groups of 2 to 30 carbon atoms, which contains N, O or S.

In an exemplary embodiment of the present specification, Ar 2 and Ar 3 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and the aryl group is a single ring. To tetracyclic aryl.

In an exemplary embodiment of the present specification, Ar 2 and Ar 3 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and the aryl group is a single ring. To tricyclic aryl.

In another exemplary embodiment of the present specification, Ar 2 and Ar 3 are the same or different from each other, and are each independently a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms, and the heterocyclic ring The group is a monocyclic to tetracyclic heterocyclic group.

In still another exemplary embodiment of the present specification, Ar 2 and Ar 3 are the same or different from each other, and are each independently a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms, and the hetero The ring group is a monocyclic to tricyclic heterocyclic group.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and the aryl group is a monocyclic to tricyclic aryl group.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group.

In another exemplary embodiment, Ar2 is phenyl.

In another exemplary embodiment of the present specification, Ar2 is a phenyl group which is unsubstituted or substituted with a substituent selected from the group consisting of a cyano group, an aryl group, and a heterocyclic group.

In still another exemplary embodiment of the present specification, Ar2 is unsubstituted or A phenyl group substituted with an aryl group.

In still another exemplary embodiment, Ar2 is a phenyl group which is unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Ar2 is a phenyl group substituted with a phenyl group.

In another exemplary embodiment, Ar2 is a phenyl group substituted with a naphthyl group.

In an exemplary embodiment of the present specification, Ar2 is a phenyl group substituted with a cyano group.

In an exemplary embodiment of the present specification, Ar2 is a phenyl group substituted with an aryl group.

In another exemplary embodiment of the present specification, Ar2 is a phenyl group substituted with a substituted or unsubstituted heterocyclic group.

In yet another exemplary embodiment, Ar2 is phenyl substituted by a substituted or unsubstituted heterocyclic group comprising one or more of N, O and S atoms.

In still another exemplary embodiment, Ar 2 is a phenyl group, which is substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms and containing one or more of N, O and S atoms Replacement of the group.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted biphenyl group.

In another exemplary embodiment, Ar2 is a biphenyl group.

In an exemplary embodiment of the present specification, Ar2 is a biphenyl group which is unsubstituted or substituted with a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, Ar2 is unsubstituted or linked A triphenyl substituted biphenyl group is extended.

In an exemplary embodiment of the present specification, Ar2 is a biphenyl group which is unsubstituted or substituted with a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted naphthyl group.

In another exemplary embodiment, Ar2 is a naphthyl group.

In yet another exemplary embodiment, Ar2 is an aryl substituted naphthyl group.

In still another exemplary embodiment, Ar2 is a naphthyl group substituted with an aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Ar2 is a naphthyl group substituted with a phenyl group.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted phenanthrenyl group.

In another exemplary embodiment, Ar2 is a phenanthrenyl group.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted fluorenyl group.

In another exemplary embodiment, Ar2 is an unsubstituted or alkyl-substituted fluorenyl group.

In an exemplary embodiment of the present specification, Ar2 is an anthracenyl group which is unsubstituted or substituted with an alkyl group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar2 is a methyl group substituted with a methyl group.

In an exemplary embodiment of the present specification, Ar2 is a 2-methyl group substituted with a methyl group.

In an exemplary embodiment of the present specification, Ar 2 is a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms, and the heterocyclic group is a monocyclic to tricyclic heterocyclic group. .

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms and containing one or more S atoms.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted monocyclic heterocyclic group containing one or more S atoms.

In another exemplary embodiment, Ar2 is a substituted or unsubstituted thienyl group.

In an exemplary embodiment of the present specification, Ar2 is a thienyl group.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms and containing one or more N atoms.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted tricyclic heterocyclic group having 3 to 30 carbon atoms and containing one or more N atoms. In another exemplary embodiment, Ar2 is a substituted or unsubstituted carbazolyl group.

In yet another exemplary embodiment, Ar2 is a carbazolyl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and the aryl group is a monocyclic to tricyclic aryl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted phenyl group.

In another exemplary embodiment, Ar3 is a phenyl group.

In another exemplary embodiment of the present specification, Ar3 is a phenyl group, and the phenyl group is unsubstituted or selected from the group consisting of a cyano group, an aryl group, and a heterocyclic group. Substituent substitution.

In still another exemplary embodiment of the present specification, Ar3 is a phenyl group which is unsubstituted or substituted with an aryl group.

In still another exemplary embodiment, Ar3 is a phenyl group which is unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Ar3 is a phenyl group substituted with a phenyl group.

In another exemplary embodiment, Ar3 is a naphthyl substituted phenyl group.

In an exemplary embodiment of the present specification, Ar3 is a phenyl group substituted with a cyano group.

In another exemplary embodiment of the present specification, Ar3 is a phenyl group substituted with a heterocyclic group.

In another exemplary embodiment, Ar3 is a phenyl group substituted with a heterocyclic group containing one or more N atoms.

In yet another exemplary embodiment, Ar3 is a phenyl group substituted with a heterocyclic group having 2 to 30 carbon atoms and containing one or more N atoms.

In still another exemplary embodiment, Ar3 is a phenyl group substituted with a pyridyl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted biphenyl group.

In another exemplary embodiment, Ar3 is a biphenyl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted naphthyl group.

In another exemplary embodiment, Ar3 is a naphthyl group.

In yet another exemplary embodiment, Ar3 is an aryl substituted naphthyl group.

In still another exemplary embodiment, Ar3 is a naphthyl group substituted with an aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Ar3 is a naphthyl group substituted with a phenyl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted phenanthrenyl group.

In another exemplary embodiment, Ar3 is a phenanthrene group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted fluorenyl group.

In another exemplary embodiment, Ar3 is an unsubstituted or alkyl-substituted fluorenyl group.

In an exemplary embodiment of the present specification, Ar3 is an anthracenyl group which is unsubstituted or substituted with an alkyl group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar3 is a methyl group substituted with a methyl group.

In an exemplary embodiment of the present specification, Ar3 is a 2-methyl group substituted with a methyl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms, and the heterocyclic group is a monocyclic to tricyclic heterocyclic group. .

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms and containing one or more S atoms.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted monocyclic heterocyclic group containing one or more S atoms.

In another exemplary embodiment, Ar3 is a substituted or unsubstituted thienyl group.

In an exemplary embodiment of the present specification, Ar3 is a thienyl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms and containing one or more N atoms.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted tetracyclic heterocyclic group having 3 to 30 carbon atoms and containing one or more N atoms.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted tricyclic heterocyclic group having 3 to 30 carbon atoms and containing one or more N atoms.

In another exemplary embodiment, Ar3 is a substituted or unsubstituted carbazolyl group.

In yet another exemplary embodiment, Ar3 is a substituted or unsubstituted benzoxazolyl group.

In yet another exemplary embodiment, Ar3 is a carbazolyl group.

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

In other exemplary embodiments, the naphthyl group is

In an exemplary embodiment of the present specification, biphenyl is

In other exemplary embodiments, the biphenyl group is

In still other exemplary embodiments, the biphenyl group is

In another exemplary embodiment, phenanthryl is

In yet another illustrative embodiment, phenanthryl is

In the present specification, the phenyl group substituted by a cyano group is

In other exemplary embodiments, the phenyl group substituted with a cyano group is

In the present specification, a heterocyclic group is selected from the following structural formula.

In an exemplary embodiment of the present specification, Ar 2 and Ar 3 are the same or different from each other and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; substituted or unsubstituted Substituted or unsubstituted phenanthryl; substituted or unsubstituted fluorenyl; substituted or unsubstituted thienyl; substituted or unsubstituted carbazolyl; substituted or unsubstituted Substituted phenothiphenyl; substituted or unsubstituted dibenzodioxanyl; substituted or unsubstituted quinolinyl; substituted or unsubstituted benzoxazolyl; Substituted or unsubstituted indolocarbazolyl.

In an exemplary embodiment of the present specification, Ar2 and Ar3 are different from each other.

In an exemplary embodiment of the present specification, Ar2 and Ar3 are each independent And differently selected from the group consisting of: substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthrene Substituted or unsubstituted fluorenyl; substituted or unsubstituted thienyl; substituted or unsubstituted carbazolyl; substituted or unsubstituted morphine; substituted or unsubstituted Substituted dibenzodioxanyl; substituted or unsubstituted quinolyl; substituted or unsubstituted benzoxazolyl; or substituted or unsubstituted indolocarbazole base.

The compound according to an exemplary embodiment of the present specification induces the maximization of amorphousness by making Ar2 and Ar3 different from Ar1. According to another exemplary embodiment of the present specification, Ar2 and Ar3 may also be configured differently from each other to induce the asymmetry of the compound represented by Chemical Formula 1, and this case may further enhance the amorphous effect.

Therefore, the amorphous property of Ar1 due to the structure of the nonlinear triphenyl group represented by Chemical Formula 2 can be further maximized by making Ar2 and Ar3 different from each other. Therefore, the heterocyclic compound according to an exemplary embodiment of the present specification can form an amorphous deposited film and can provide an element having a low driving voltage and a long service life.

Specifically, when one of Ar2 and Ar3 has a carbazolyl group, a broad light-emitting region is formed in the light-emitting layer by suppressing the electron transporting ability of the triazine, pyrimidine and pyridine skeleton. Therefore, there is a role of giving the organic light-emitting element a long service life.

In an exemplary embodiment of the present specification, X1 to X3 are the same or different from each other, and are each independently N or CR, at least one of X1 to X3 is N, and R is each independently hydrogen or deuterium.

In an exemplary embodiment of the present specification, X1 to X3 are the same or different from each other, and are each independently N or CH, and at least one of X1 to X3 is N.

In an exemplary embodiment of the present specification, X1 to X3 may all be N.

In an exemplary embodiment of the present specification, X1 may be N and X2 and X3 may be CH.

In an exemplary embodiment of the present specification, X2 may be N and X1 and X3 may be CH.

In an exemplary embodiment of the present specification, X3 may be N and X1 and X2 may be CH.

In an exemplary embodiment of the present specification, X1 and X2 may be N. In this case, X3 is CH.

In an exemplary embodiment of the present specification, X1 and X3 may be N. In this case, X2 is CH.

In an exemplary embodiment of the present specification, X2 and X3 may be N. In this case, X1 is CH.

In an exemplary embodiment of the present specification, X1 to X3 are N.

In an exemplary embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following structural formulae.

In another exemplary embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following structural formulae.

In still another exemplary embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following structural formulae.

The heterocyclic compound according to an exemplary embodiment of the present specification can be produced by the production method described below.

The heterocyclic compound of the present specification can be produced by a method of reacting the chemical formula 2 in which a halogen group or a cyclopentylborane group is substituted in Ar2 and Ar3. Substituted in the structure of X1 to X3 in which a halogen group is substituted.

Further, the present specification provides an organic light-emitting element comprising the heterocyclic compound represented by Chemical Formula 1.

The present specification provides an organic light emitting device comprising: a cathode; an anode; and one or more organic material layers disposed between the cathode and the anode, Wherein one or more layers of the organic material layer comprise a heterocyclic compound as described above.

When a member is placed "on" another member in this specification, this includes not only the case where the one member is in contact with another member but also the case where another member exists between the two members. .

When a component is "contained" in the specification, unless otherwise specifically described, it is not intended to exclude another component, but rather to include another component.

The organic material layer of the organic light-emitting element of the present specification may be composed not only of a single layer structure but also of a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting element 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 element is not limited thereto, and may include a smaller number of organic layers.

In an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer contains a heterocyclic compound.

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer contains a heterocyclic compound.

In still another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer contains a heterocyclic compound as a host of the light emitting layer.

In an exemplary embodiment of the present specification, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer contains a heterocyclic compound.

An exemplary embodiment of the present specification includes: a cathode; an anode; a light-emitting layer disposed between the cathode and the anode; and one or two or more than two organic material layers disposed between the anode and the light-emitting layer, and an organic material The layer comprises a heterocyclic compound, and one or more layers of organic material are selected from the group consisting of: an electron transport layer, an electron injection layer, a layer that simultaneously transports and ejects electrons, and a hole blocking layer.

In an exemplary embodiment of the present specification, the organic material layer disposed between the anode and the light-emitting layer has two or more than two layers.

In an exemplary embodiment of the present specification, the organic material layer contains two or more than two electron transport layers, and at least one of the two or more than two electron transport layers contains a heterocyclic compound. In particular, in an exemplary embodiment of the present specification, the heterocyclic compound may also be included in one of the two or more than two electron transport layers, and may be included in the two or more than two In each layer of the electron transport layer.

Further, in an exemplary embodiment of the present specification, when a heterocyclic compound is contained in each of the two or more than two electron transporting layers, materials other than the heterocyclic compound may be the same or different from each other.

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

In an exemplary embodiment of the present specification, the organic material layer further includes a hole injection layer or a hole transport layer, and the organic material layer includes an aryl group-containing group and an oxazolyl group in addition to the heterocyclic compound. Or a compound of benzoxazolyl.

In an exemplary embodiment of the present specification, the organic material layer containing the heterocyclic compound contains a heterocyclic compound as a host and another organic compound, a metal or a metal compound as a dopant.

In another exemplary embodiment, the organic light emitting element may be an organic light emitting element having an anode, one or more organic material layers, and a structure (standard type) in which the cathodes are sequentially stacked on the substrate.

In another exemplary embodiment, the organic light emitting element may be an organic light emitting element having a cathode, one or more organic material layers, and a reverse structure (inverted type) in which the anodes are sequentially stacked on the substrate.

For example, the structure of an organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2.

1 illustrates the structure of an organic light-emitting element in which a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 are sequentially stacked. In the structure, a heterocyclic compound may be contained in the light-emitting layer 3.

2 illustrates the structure of an organic light emitting diode in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a cathode 4 are sequentially stacked. In the structure, the heterocyclic compound may be contained in one or more of the hole injection layer 5, the hole transport layer 6, the light-emitting layer 3, and the electron transport layer 7.

1 and 2 illustrate an organic light emitting element, and the organic light emitting element is not limited this.

When the organic light emitting element 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 element of the present specification can be produced by materials and methods known in the art, but one or more layers of the organic material layer contain a heterocyclic compound, that is, a compound represented by Chemical Formula 1.

For example, the organic light-emitting element of the present specification can be fabricated by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. In this case, the organic light-emitting element can be fabricated by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to have conductivity. A metal or metal oxide, or an alloy thereof, is deposited on the substrate to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and then deposited thereon Used as a material for the cathode. In addition to the methods described above, the organic light-emitting element can also be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

Further, when the organic light-emitting element is manufactured, the compound of Chemical Formula 1 can be formed not only by a vacuum deposition method but also by a solution coating method as an organic material layer. Here, the solution coating method means spin coating, dip coating, blade scraping, ink jet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to the method as described above, an organic light-emitting element can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Publication No. 2003/012890). However, the manufacturing method is not limited to this.

As the anode material, a material having a large work function is usually preferable in order to smoothly inject a hole into the organic material layer. Specific examples of the anode material which can be used in the present specification 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 metals and oxides such as ZnO:Al or SnO ₂ :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4 -(3,4-(ethylene-1,2-dioxy)thiophene], PEDOT), polypyrrole and polyaniline, and the like, but not Limited to this.

As the cathode material, a material having a small work function is usually preferable in order to smoothly inject electrons into the organic material layer. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, lanthanum, lithium, lanthanum, aluminum, silver, tin, and lead, or alloys thereof; multilayer structural materials such as LiF/Al or LiO ₂ / Al, and the like, but not limited to this.

The hole injecting material is a layer injected from the electrode into the hole, and is preferably a compound having the ability to transport holes, and thus having a function of injecting a hole in the anode and injecting a hole for the light emitting layer or The excellent function of the luminescent material prevents the excitons generated by the luminescent layer from moving into the electron injecting layer or the electron injecting material, and the ability to form a thin film is excellent. The highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the peripheral organic material layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine organic material, hexonitrile hexaazatriphenylene organic material, quinacridone organic material, quinone organic material, hydrazine, Polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto.

The hole transport layer receives holes from the hole injection layer and transmits the holes to the hair The layer of the light layer, and the hole transporting material is a material that can receive a hole from the anode or the hole injection layer to transfer the hole to the light emitting layer, and is preferably a material having a large hole mobility. Specifically, it includes an aromatic amine-based organic material, a conductive polymer, a conjugated portion, and a block copolymer in which a non-conjugated portion coexists, and the like, but is not limited thereto.

The luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer, and combine the holes and electrons to emit light in the visible light region, and is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole compound; distyrene-based compound; BAlq; 10-hydroxybenzoquinoline-metal compound; benzoxazole , benzothiazoles and benzimidazoles; poly(p-phenylenevinylene, PPV) polymers; spiro compounds; polyfluorene, rubeene, and Analogous, but not limited to.

The luminescent layer may comprise a host material and a dopant material. Examples of the host material include a condensed aromatic ring derivative, or a compound containing a hetero ring, and the like. Specifically, examples of the condensed aromatic ring derivative include an anthracene derivative, an anthracene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like. Examples of the compound containing a hetero ring include a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, and the like, but examples thereof are not limited thereto.

Examples of the doping material include an aromatic amine derivative, a styrylamine compound, a boron complex, an allene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and examples thereof include ruthenium, osmium, yttrium, diterpene fluorene, and the like having an arylamine group. And the styrylamine compound is a substituted or unsubstituted arylamine One aryl vinyl substituted compound, and one or two or more than two substituents selected from the group consisting of substituted or unsubstituted: aryl, decyl, alkyl, naphthenic Base and arylamine group. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, and the like, but are not limited thereto. Further, examples of the metal complex include ruthenium complex, platinum complex, and the like, but are not limited thereto.

The electron transporting material is a material that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting material is a material that can sufficiently inject electrons from the cathode and can transfer electrons to the light emitting layer, and is preferably allowed to allow larger electrons Mobility material. Specific examples thereof include: an Al complex of 8-hydroxyquinoline; a complex comprising Alq ₃ ; an organic group compound; a hydroxyflavone-metal complex; and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material, as used in accordance with the related art. In particular, examples of suitable cathode materials are typical materials having a low work function, followed by an aluminum layer or a silver layer. Specific examples thereof include ruthenium, osmium, calcium, strontium and barium, and in each case, an aluminum layer or a silver layer.

The electron injecting layer is a layer which injects electrons from the electrode, and is preferably a compound which has the ability to transport electrons, has an effect of injecting electrons from the cathode, and has an excellent effect of injecting electrons into the light emitting layer or the light emitting material. The excitons generated by the light-emitting layer are prevented from moving to the hole injection layer, and the ability to form a film is also excellent. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, anthracene. Perylenetetracarboxylic acid, fluorenylidene methane, anthrone and the like, and derivatives thereof, metal complex compounds, a 5-membered ring derivative of nitrogen, and the like, but is not limited thereto.

Examples of metal complex compounds include 8-hydroxyquinolinyl lithium, bis(8-hydroxyquinolinyl) zinc, bis(8-hydroxyquinolinyl) copper, bis(8-hydroxyquinolinyl) manganese, ginseng (8-hydroxyquinolinyl) aluminum, ginseng (2-methyl-8-hydroxyquinolinyl) aluminum, ginseng (8-hydroxyquinolinyl) gallium, bis(10-hydroxybenzo[h]quinolinyl ) bismuth, bis(10-hydroxybenzo[h]quinolinyl)zinc, bis(2-methyl-8-quinolinyl)chlorogallium, bis(2-methyl-8-quinolinyl) (o-) Cresol) gallium, bis(2-methyl-8-quinolinyl)(1-naphthyl)aluminum, bis(2-methyl-8-quinolinyl)(2-naphthol) gallium, and the like Things, but not limited to them.

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

The organic light-emitting element according to the present specification may be of a top emission type, a bottom emission type or a dual emission type, depending on the materials used.

In an exemplary embodiment of the present specification, a heterocyclic compound may be contained in an organic solar cell or an organic transistor in addition to the organic light-emitting element.

Hereinafter, the present invention will be described in detail with reference to examples for specifically describing the present specification. However, the examples according to the present specification may be modified in various forms, and the scope of the present specification should not be construed as being limited to the examples described in detail below. The examples are provided to more fully explain the present specification to those of ordinary skill in the art.

Preparation Example 1. Synthetic Chemical Formula 1-1

[Chemical Formula 1-1]

In the case of 2-chloro-4,6-diphenyl-1,3,5-triazine (10 g, 37.4 mmol) and [1,1':3',1"-bitriphenyl]-5 After the --boronic acid (10.2 g, 37.4 mmol) was completely dissolved in tetrahydrofuran (60 ml), potassium carbonate (15.5 g, 112.1 mmol) was dissolved in 20 ml of water, and the resulting solution was added thereto. Yttrium-triphenylphosphine palladium (1.29 g, 1.12 mmol) was added, and then the resulting mixture was heated and stirred for 2 hours. The temperature was lowered to normal temperature, the reaction was terminated, and then the potassium carbonate solution was removed, and the white solid was filtered. The white solid was washed twice with tetrahydrofuran and ethyl acetate to give a compound of formula 1-1 (15.5 g, yield 90%).

MS[M+H] ⁺ =462

Preparation Example 2. Synthetic Chemical Formula 1-2

The compound of Chemical Formula 1-2 is prepared in the same manner as the method of preparing the compound represented by Chemical Formula 1-1 except that 2-chloro-4-(naphthalen-1-yl)-6-phenyl-1,3,5 is used. Triazine was used instead of the 2-chloro-4,6-diphenyl-1,3,5-triazine of Example 1.

MS[M+H] ⁺ =512

Preparation Example 3. Synthetic Chemical Formulas 1-3

The compound of Chemical Formula 1-3 is prepared in the same manner as the method of preparing the compound represented by Chemical Formula 1-1, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6- Phenyl-1,3,5-triazine was substituted for the 2-chloro-4,6-diphenyl-1,3,5-triazine of Example 1.

MS[M+H] ⁺ =538

Preparation Example 4. Synthetic Chemical Formulas 1-4

The compound of Chemical Formula 1-4 is prepared in the same manner as the method of preparing the compound represented by Chemical Formula 1-1, except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6- Phenyl-1,3,5-triazine was substituted for the 2-chloro-4,6-diphenyl-1,3,5-triazine of Example 1.

MS[M+H] ⁺ =538

Preparation Example 5. Synthetic Chemical Formula 1-5

[Chemical Formula 1-5]

The compound of Chemical Formula 1-5 is prepared in the same manner as the method of preparing the compound represented by Chemical Formula 1-1, except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6- Phenyl-1,3,5-triazine was substituted for the 2-chloro-4,6-diphenyl-1,3,5-triazine of Example 1.

MS[M+H] ⁺ =538

Preparation Example 6. Synthetic Chemical Formula 2-1

The compound of the formula 2-1 is prepared in the same manner as the method of preparing the compound represented by the formula 1-1, except that 4-([1,1'-biphenyl]-4-yl)-6-chloro-2- is used. Phenylpyrimidine was substituted for the 2-chloro-4,6-diphenyl-1,3,5-triazine of Example 1.

MS[M+H] ⁺ =537

Preparation Example 7. Synthetic Chemical Formula 2-2

The compound of the formula 2-2 is produced in the same manner as the method for producing the compound represented by the formula 1-1, except that 4-chloro-6-phenyl-2-(4-(pyridin-2-yl)phenyl) is used. Pyrimidine was substituted for the 2-chloro-4,6-diphenyl-1,3,5-triazine of Example 1.

MS[M+H] ⁺ =538

Preparation Example 8. Synthetic Chemical Formula 2-3

The compound of Chemical Formula 2-3 is prepared in the same manner as the method of preparing the compound represented by Chemical Formula 1-1, except that 2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro is used. Pyrimidine was substituted for the 2-chloro-4,6-diphenyl-1,3,5-triazine of Example 1.

MS[M+H] ⁺ =613

Preparation Example 9. Synthetic Chemical Formula 3-1

The compound of Chemical Formula 3-1 is prepared in the same manner as the method for preparing the compound represented by Chemical Formula 1-1, except that 4-([1,1'-biphenyl]-4-yl)-2-chloro-6- Phenylpyrimidine was substituted for the 2-chloro-4,6-diphenyl-1,3,5-triazine of Example 1.

MS[M+H] ⁺ =537

Preparation Example 10. Synthetic Chemical Formula 3-2

The compound of Chemical Formula 3-2 is prepared in the same manner as the method of preparing the compound represented by Chemical Formula 1-1, except that 4,6-di([1,1'-biphenyl]-4-yl)-2-chloro is used. Pyrimidine was substituted for the 2-chloro-4,6-diphenyl-1,3,5-triazine of Example 1.

MS[M+H] ⁺ =613

Preparation Example 11. Synthetic Chemical Formula 1-6

The compound of Chemical Formula 1-6 is prepared in the same manner as the method of preparing the compound represented by Chemical Formula 1-1 except that 4-(4-chloro-6-phenyl-1,3,5-triazin-2-yl is used. The benzonitrile was substituted for the 2-chloro-4,6-diphenyl-1,3,5-triazine of Example 1.

MS[M+H] ⁺ =487

Preparation Example 12. Synthetic Chemical Formula 1-7

The compound of Chemical Formula 1-7 is prepared in the same manner as the method of preparing the compound represented by Chemical Formula 1-1, except that 2-([1,1':3',1"-indenyl]-5'-yl is used. -4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine and (4-(9H-carbazol-9-yl)phenyl)boronic acid were respectively substituted for the preparation example 1. 2-Chloro-4,6-diphenyl-1,3,5-triazine and [1,1':3',1"-bitriphenyl]-5'-ylboronic acid.

MS[M+H] ⁺ =703

Preparation Example 13. Synthetic Chemical Formula 2-4

The compound of Chemical Formula 2-4 is prepared in the same manner as the method of preparing the compound represented by Chemical Formula 1-7, except that 4-([1,1':3',1"-biphenyl]-5'-yl group is used. -6-(4-chlorophenyl)-2-phenylpyrimidine instead of 2-([1,1':3',1"-indenyl]-5 ¹ -yl)-4 in Preparation Example 12. -(3-Chlorophenyl)-6-phenyl-1,3,5-triazine.

MS[M+H] ⁺ =702

<Experimental Example 1-1>

Thinly coated with an indium tin oxide (ITO) thickness of 1,000 Å (Å) The glass substrate was placed in distilled water in which a detergent was dissolved, and ultrasonic washing was performed. In this case, a product manufactured by Fischer Co. was used as a cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, the ultrasonic washing was repeated twice using distilled water for 10 minutes. After the washing with distilled water was completed, ultrasonic washing was performed using isopropyl alcohol, acetone, and methanol solvent, and drying was performed, and then the product was transferred to a plasma cleaner. In addition, the substrate was cleaned using oxygen plasma for 5 minutes and then the substrate was transferred to a vacuum evaporator.

The following compound [HI-A] was thermally vacuum deposited on the thus prepared transparent ITO electrode to a thickness of 600 Å, thereby forming a hole injection layer. The following chemical formula of Hexanitrile hexaazatriphenylene (HAT) and the following compound [HT-A] were vacuum deposited on the hole injection layer to respectively reach a thickness of 50 angstroms and 600 angstroms, thereby forming a hole. Transport layer.

Next, the following compound [BH] and the compound [BD] were vacuum deposited on the hole transport layer at a weight ratio of 25:1 to a film thickness of 200 angstroms, thereby forming a light-emitting layer.

A compound of [Formula 1-1] and a compound [LiQ] (lithium quinolate) were vacuum-deposited on the light-emitting layer at a weight ratio of 1:1, thereby forming an electron injecting and transporting layer having a thickness of 350 Å. Lithium fluoride (LiF) and aluminum were sequentially deposited on the electron injecting and transporting layer to a thickness of 10 angstroms and 1,000 angstroms, respectively, thereby forming a negative electrode.

In the foregoing procedure, the deposition rate of the organic material is maintained at 0.4 Å/sec to 0.9 Å/sec, and the deposition rates of lithium fluoride and aluminum of the negative electrode are maintained at 0.3 Å/sec and 2 Å/sec, respectively, and during deposition. The degree of vacuum was maintained at 1 × 10 ^-7 Torr to 5 × 10 ^-8 Torr, thereby manufacturing an organic light-emitting element.

[HAT]

<Experimental Example 1-2>

The organic light-emitting element was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula 1-2 was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Experimental Example 1-3>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula 1-3 was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Experimental Example 1-4>

The organic light-emitting element was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula 1-4 was used instead of the chemical formula 1-1 in Experimental Example 1-1. Things.

<Experimental Example 1-5>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula 1-5 was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Experimental Example 1-6>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula 1-6 was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Experimental Example 1-7>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula 1-7 was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 1-1>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of the chemical formula ET-1-A was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 1-2>

The organic light-emitting element was fabricated in the same manner as Experimental Example 1-1, except that the compound of the chemical formula ET-1-B was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 1-3>

An organic light-emitting device was fabricated in the same manner as Experimental Example 1-1 except that a compound of the formula ET-1-C was used instead of the chemical formula 1-1 in Experimental Example 1-1. Compound.

<Comparative Example 1-4>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of the chemical formula ET-1-D was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 1-5>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of the chemical formula ET-1-E was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 1-6>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of the chemical formula ET-1-F was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 1-7>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1 except that the compound of the chemical formula ET-1-G was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 1-8>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of the chemical formula ET-1-H was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 1-9>

An organic light-emitting device was fabricated in the same manner as Experimental Example 1-1 except that a compound of the formula ET-1-I was used instead of the chemical formula 1-1 in Experimental Example 1-1. Compound.

<Comparative Example 1-10>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1 except that the compound of the chemical formula ET-1-J was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 1-11>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of the chemical formula ET-1-K was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 1-12>

The organic light-emitting element was fabricated in the same manner as Experimental Example 1-1 except that the compound of the chemical formula ET-1-L was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 1-13>

The organic light-emitting element was fabricated in the same manner as Experimental Example 1-1, except that the compound of the chemical formula ET-1-M was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 1-14>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of the chemical formula ET-1-N was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 1-15>

An organic light-emitting device was fabricated in the same manner as Experimental Example 1-1 except that a compound of the formula ET-1-O was used instead of the chemical formula 1-1 in Experimental Example 1-1. Compound.

<Comparative Example 1-16>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of the chemical formula ET-1-P was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 1-17>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula ET-1-Q was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 1-18>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of the chemical formula ET-1-R was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

For the organic light-emitting element manufactured by the above method, the driving voltage and the luminous efficiency were measured at a current density of 10 mA/cm 2 and measured at a current density of 20 mA/cm 2 to reach 90% of the initial luminance. The time required for the value (T ₉₀ ). The results are shown in Table 1 below.

From the results of Table 1, it can be confirmed that the compound represented by Chemical Formula 1 according to an exemplary embodiment of the present specification can be used for the organic material layer of the organic light-emitting element, which can simultaneously inject and transport electrons.

In addition, it can be confirmed by experimental examples and comparative examples that, as in an exemplary embodiment of the present specification, the case where Ar 2 and Ar 3 are different from Ar 1 and contains a triphenyl group represented by Chemical Formula 2 can provide high efficiency and low efficiency. An organic light-emitting element that drives voltage and has a long lifetime.

Specifically, when the experimental example is compared with the comparative example, it can be confirmed that in the case of containing a triphenyl group having a different structure, in the case of containing a triphenyl group represented by Chemical Formula 2, in the organic light emission The components exhibit excellent characteristics in terms of driving voltage, efficiency and service life. The foregoing result is due to the fact that when a structure represented by Chemical Formula 2 and having a nonlinear structure is introduced, a wider optical band gap can be formed.

Further, when Experimental Example 1-1 was compared with Comparative Example 1-6 and Comparative Example 1-7, it was confirmed that a condensed ring was formed as compared with by substituting with another substituent or combining another substituent with each other. In the case where the triphenyl group represented by Chemical Formula 2 is contained, the organic light-emitting element exhibits excellent characteristics.

In addition, it can be confirmed from Comparative Examples 1-8 and Comparative Examples 1-9 that the case where the triazine compound having symmetry is used for the organic material layer capable of simultaneously injecting and transporting electrons includes exemplification according to one of the present specifications. The organic light-emitting element of the heterocyclic compound of the embodiment has higher efficiency, lower driving voltage, and longer lifetime.

It can be confirmed from Comparative Examples 1-10 that in the case of an organic light-emitting element comprising a heterocyclic compound according to an exemplary embodiment of the present specification, Ar2 and Ar2 and Ar3 are in the case of a five- or higher-order ring. The case where Ar3 is lower than the five rings has a lower driving voltage and a longer service life.

Further, it can be confirmed from Comparative Examples 1 to 11 and Experimental Examples that L is a direct bond and provides a lower driving voltage and higher luminous efficiency than in the case where L has a linking group even when Ar2 and Ar3 are identical to each other. And longer life organic light-emitting elements.

In addition, it can be confirmed from Comparative Examples 1-12 and Comparative Examples 1-14 and experimental examples that the case where L is a direct bond provides a lower driving voltage, higher luminous efficiency, and longer use than the case where L has a linking group. Lifetime organic light-emitting elements.

In addition, it can be confirmed from Comparative Example 1-17 and Comparative Examples 1 to 18 and experimental examples that the case where the triphenyl group represented by Chemical Formula 2 is contained in the structure in which any one of Ar1 to Ar3 is substituted with a carbazole derivative An organic light-emitting element having a low driving voltage, high luminous efficiency, and long service life is provided.

The chemical formula 1 according to an exemplary embodiment of the present specification The composition has excellent thermal stability, a deep HOMO level of 6.0 eV or higher, a triple triplet energy (ET) and a hole stability and thus can exhibit excellent characteristics.

In an exemplary embodiment of the present specification, when the compound is used in an organic material layer capable of simultaneously injecting and transporting electrons, a mixture of the compound and an n-type dopant may be used. Therefore, the compound represented by Chemical Formula 1 can have a low driving voltage and high efficiency, and the stability of the element can be improved by the hole stability of the compound.

<Experimental Example 2-1>

The organic light-emitting element was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula 2-1 was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Experimental Example 2-2>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula 2-2 was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Experimental Example 2-3>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula 2-3 was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Experimental Example 2-4>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula 3-1 was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Experimental Example 2-5>

An organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula 3-2 was used instead of the chemical formula 1-1 in Experimental Example 1-1. Things.

<Experimental Example 2-6>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula 2-4 was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 2-1>

An organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula ET-2-A was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 2-2>

An organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula ET-2-B was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 2-3>

The organic light-emitting element was fabricated in the same manner as Experimental Example 1-1, except that the compound of the chemical formula ET-2-C was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 2-4>

An organic light-emitting device was fabricated in the same manner as Experimental Example 1-1 except that a compound of the chemical formula ET-2-D was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 2-5>

An organic light-emitting device was fabricated in the same manner as Experimental Example 1-1 except that a compound of the formula ET-2-E was used instead of the chemical formula 1-1 in Experimental Example 1-1. Compound.

<Comparative Example 2-6>

An organic light-emitting device was fabricated in the same manner as Experimental Example 1-1 except that a compound of the chemical formula ET-2-F was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 2-7>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula ET-2-G was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 2-8>

The organic light-emitting element was fabricated in the same manner as Experimental Example 1-1, except that the compound of Chemical Formula ET-2-H was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 2-9>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1 except that the compound of the chemical formula ET-2-I was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

<Comparative Example 2-10>

The organic light-emitting device was fabricated in the same manner as Experimental Example 1-1, except that the compound of the chemical formula ET-2-J was used instead of the compound of Chemical Formula 1-1 in Experimental Example 1-1.

For the organic light-emitting element manufactured by the above method, the driving voltage and the luminous efficiency were measured at a current density of 10 mA/cm 2 and measured at a current density of 20 mA/cm 2 to reach 90% of the initial luminance. The time required for the value (T ₉₀ ). The results are shown in Table 2 below.

From the results of Table 2, it was confirmed that the compound represented by Chemical Formula 1 according to an exemplary embodiment of the present specification can be used for an organic layer of an organic light-emitting element which can simultaneously inject and transport electrons.

In addition, it can be confirmed by experimental examples and comparative examples that, as in an exemplary embodiment of the present specification, Ar 2 and Ar 3 are different from Ar 1 and a direct bond containing a triphenyl group represented by Chemical Formula 2 can be provided. High-efficiency, low-drive voltage and long-life organic light-emitting elements.

Further, as a result of Comparative Examples 2 to 8 and Comparative Examples 2 to 10 and experimental examples, it was confirmed that the triphenyl group represented by Chemical Formula 2 was contained in the structure in which any of Ar1 to Ar3 was substituted with a carbazole derivative. Provides low drive voltage and high Organic light-emitting element with luminous efficiency and long service life.

The compound represented by Chemical Formula 1 according to an exemplary embodiment of the present specification has excellent thermal stability, a deep HOMO level of 6.0 eV or higher, a high triplet energy (ET), and a hole stability and thus can Shows excellent features.

In an exemplary embodiment of the present specification, when the compound is used in an organic material layer capable of simultaneously injecting and transporting electrons, a mixture of the compound and an n-type dopant may be used. Therefore, the compound represented by Chemical Formula 1 can have a low driving voltage and high efficiency, and the stability of the element can be improved by the hole stability of the compound.

An important feature of an organic material for an organic light-emitting element is that it is required to form an amorphous deposited film, and an organic material having high crystallinity has a disadvantage in that the film is unevenly deposited during deposition, and thus, when driving the element, driving The voltage is greatly increased, and the life of the component is shortened, and thus the component is rapidly deteriorated. In order to compensate for these disadvantages, it is necessary to form an amorphous film, and the inventors increase the asymmetry by making Ar2 and Ar3 different from Ar1 in the structure containing X1 to X3, thereby promoting the formation of an amorphous film.

Further, the formation of the aforementioned amorphous film is maximized by introducing the structure of Chemical Formula 2.

Claims (12)

A heterocyclic compound represented by the following Chemical Formula 1: In Chemical Formula 1, X1 to X3 are the same or different from each other, and are each independently N or CH, and X1 to X3 are not simultaneously CH, and Ar1 is a substituent represented by the following Chemical Formula 2, L is a direct bond, Ar2 and Ar3 are different from Ar1, and Ar2 and Ar3 are each independently unsubstituted or substituted by cyano, dimethyl decyl, triphenylene, phenothiaphthyl, dibenzodioxanyl, a phenyl group substituted with a quinolyl group or a benzoxazolinyl group; unsubstituted or substituted by cyano, dimethyl decyl, triphenylene, phenothiaphthyl, dibenzodioxyl, quinolyl or Benzooxazolyl substituted biphenyl; unsubstituted naphthyl; unsubstituted phenanthryl; unsubstituted or methyl substituted thiol; unsubstituted thienyl; unsubstituted Ethylthio; unsubstituted dibenzodioxanyl; unsubstituted quinolyl; unsubstituted benzoxazolyl; or unsubstituted indolocarbazolyl. The heterocyclic compound according to claim 1, wherein Ar2 and Ar3 are different from each other. The heterocyclic compound according to claim 1, wherein X1 to X3 are N. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following chemical structural formulae: The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following chemical structural formulae: The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following chemical structural formulae: The heterocyclic compound according to claim 1, wherein the compound of Chemical Formula 1 has a glass transition temperature (Tg) of 120 ° C or higher. An organic light-emitting element comprising: a cathode; an anode; and one or more organic material layers disposed between the cathode and the anode, wherein one or more layers of the organic material layer include The heterocyclic compound according to any one of items 1 to 7. The organic light-emitting element according to claim 8, wherein the organic material layer comprises a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the hetero ring Compound. The organic light-emitting element of claim 8, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer comprises the heterocyclic compound. The organic light-emitting element according to claim 8, wherein the organic material layer comprises an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer comprises the heterocyclic compound. The organic light-emitting device of claim 8, further comprising: one or two or more than two selected from the group consisting of: a hole injection layer, a hole transport layer, an electron transport layer, Electron injection layer, electron blocking layer and hole blocking layer.