TW201704236A - Heterocyclic compound and organic light-emitting device - Google Patents

Abstract

The present application provides a heterocyclic compound and an organic light-emitting device, which can greatly improve the lifetime, efficiency, electrochemical stability and thermal stability of an organic light-emitting device, and the organic compound layer in the organic light-emitting device includes The heterocyclic compound.

Description

Heterocyclic compound and organic light-emitting device

The present application claims the priority of Korean Patent Application No. 10-2015-0060829 and No. 10-2015-0060836 filed on April 29, 2015 in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. This reference.

This application relates to a heterocyclic compound and an organic light-emitting device using the heterocyclic compound.

The electroluminescent device is a self-luminous display device, which has the advantages of wide viewing angle, strong contrast and fast response speed.

The organic light-emitting device has a structure in which an organic film is disposed between the two electrodes. When a voltage is applied to the organic light-emitting device having such a structure, electrons and holes injected from the two electrodes are bonded to each other on the organic thin film to form a pair, and then emit light when it is lowered to the ground state. The organic film may be a single layer or may be a plurality of layers as needed.

The material of the organic film has a light-emitting function as needed. For example, the material of the organic thin film may be a compound capable of constituting the light-emitting layer by itself, and a compound may be used as a host material or a dopant of the blended light-emitting layer. Further, the material of the organic thin film may also be a compound having functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport, or electron injection.

In order to improve the performance, service life or efficiency of an organic light-emitting device, it is necessary to continuously develop materials for organic thin films.

[Reference List] [Patent Documents] US Patent No. 4,356,429

[technical problem]

We need to study an organic light-emitting device whose chemical structure has the conditions required for the material of the organic light-emitting device, such as appropriate energy level, electrochemical stability, thermal stability, etc., and can be replaced by a substituent. The various functions required for the organic light-emitting device are exerted.

[Technical Solutions]

An exemplary embodiment of the present application provides a heterocyclic compound represented by the following Chemical Formula 1.

[Chemical Formula 1] In Chemical Formula 1, R1 is hydrogen or heavy hydrogen, or is represented by -(Li)p-(Y1)q, R2 is hydrogen, heavy hydrogen or a naphthyl group, or by -(L2)r-(Y2) As indicated by s, L1 and L2 are each independently selected from the group consisting of a monosubstituted or unsubstituted arylene group; and a substituted or unsubstituted cyclic or polycyclic heteroarylene group, Y1 and Y2 Is selected from the group consisting of: hydrogen; heavy hydrogen; a halogen group; -CN; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkyne group a monosubstituted or unsubstituted alkoxy group; a monosubstituted or unsubstituted cycloalkyl group; a monosubstituted or unsubstituted heterocycloalkyl group; a monosubstituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; ;-SiRR'R";-P(=O)RR'; and an amine group which is not taken or substituted with an alkyl group, a monosubstituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; , p is 0 to 10 and q is 1 to 10, r is 0 to 10, and s is 1 to 10, and R3 to R10 are the same or different from each other, and are each independently selected from the group consisting of: hydrogen; Heavy hydrogen; a halogen group a -substituted or unsubstituted alkyl group; a monosubstituted or unsubstituted alkenyl group; a monosubstituted or unsubstituted alkyne group; a monosubstituted or unsubstituted alkoxy group; a monosubstituted or unsubstituted cycloalkyl group; a monosubstituted or unsubstituted heterocycloalkyl group; a monosubstituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; -SiRR'R";-P(=O)RR'; and an amine group , which is unsubstituted or substituted with a monoalkyl group, a monosubstituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted a monocyclic or polycyclic aliphatic or aromatic hydrocarbon ring group, and R, R' and R" are the same or different from each other, and each independently is hydrogen; a heavy hydrogen; -CN; a monosubstituted or unsubstituted alkyl group; a monosubstituted or unsubstituted cycloalkyl group; a monosubstituted or unsubstituted aryl group; or a monosubstituted or unsubstituted heteroaryl group.

In addition, another exemplary embodiment of the present application provides an organic light emitting device including a positive electrode, a negative electrode, and one or more organic material layers disposed between the positive electrode and the negative electrode, the organic material layer One or more of the above includes the above heterocyclic compound.

[Help effect]

A heterocyclic compound according to an exemplary embodiment of the present application can be used as a material of an organic material layer in an organic light-emitting device. The heterocyclic compound can be used as a material for a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like in an organic light-emitting device. Specifically, the heterocyclic compound represented by Chemical Formula 1 can be used as an electron transport layer, a hole transport layer or a light-emitting layer material of an organic light-emitting device. Further, when the heterocyclic compound represented by Chemical Formula 1 is used in an organic light-emitting device, it contributes to lowering the driving voltage of the device, improving the luminous efficiency of the device, and prolonging the life characteristics of the device with its thermal stability.

The contents of this application are detailed below.

A heterocyclic compound according to an exemplary embodiment of the present application is represented by Chemical Formula 1. More specifically, the heterocyclic compound represented by Chemical Formula 1 can be used as a material of the organic material layer in the organic light-emitting device because of the structural characteristics and substituents of the above core structure.

According to an exemplary embodiment of the present specification, Chemical Formula 1 can be expressed as any one of the following Chemical Formulas 2 to 7.

[Chemical Formula 2]

[Chemical Formula 3]

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

[Chemical Formula 7]

In the formulas 2 to 7, R1 to R10 have the same definitions as in Chemical Formula 1.

R11 is each independently selected from the group consisting of: hydrogen; heavy hydrogen; a halogen group; -CN; a monosubstituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted Alkynyl group; monosubstituted or unsubstituted alkoxy group; monosubstituted or unsubstituted cycloalkyl group; monosubstituted or unsubstituted heterocycloalkyl group; monosubstituted or unsubstituted aryl group; monosubstituted or unsubstituted hetero An aryl group; -SiRR'R"; -P(=O)RR'; and an unsubstituted or substituted with a monoalkyl group, a monosubstituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group The amine group, R, R' and R" are the same or different from each other, and are each independently hydrogen; heavy hydrogen; -CN; a mono- or unsubstituted alkyl group; a mono- or unsubstituted cycloalkyl group; a monosubstituted or unsubstituted aryl group; or a monosubstituted or unsubstituted heteroaryl group, each of which is an integer of from 0 to 7, and when m is 2 or more, two or more R11 are the same or different from each other, And n is each an integer of 0 to 5, and when n is 2 or more, two or more R11 are the same or different from each other.

In an exemplary embodiment of the present application, when R2 of Chemical Formula 1 is hydrogen or heavy hydrogen, R1 may be represented by -(L1)p-(Y1)q.

In an exemplary embodiment of the present application, L1 of Chemical Formula 1 is a monosubstituted or unsubstituted arylene group, and Y may be selected from the group consisting of hydrogen; heavy hydrogen; monosubstituted or unsubstituted aromatic a group; a substituted or unsubstituted heteroaryl group; and -P(=O)RR'.

In an exemplary embodiment of the present application, R11 of Chemical Formulas 2 to 4 may each independently be selected from the group consisting of hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group; a substituted or unsubstituted hetero An aryl group; and -P(=O)RR'.

In an exemplary embodiment of the present application, when R1 of Chemical Formula 1 is hydrogen or heavy hydrogen, R2 may be a naphthyl group or represented by -(L2)r-(Y2)s. R2 can be an unsubstituted naphthalene group.

In an exemplary embodiment of the present application, L2 of Chemical Formula 1 is a monosubstituted or unsubstituted arylene group, and Y may be selected from the group consisting of: a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and -P(=O)RR'.

In an exemplary embodiment of the present application, R11 of Chemical Formulas 5 to 7 may each independently be selected from the group consisting of: a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; And -P(=O)RR'.

In an exemplary embodiment of the present application, p and r of Chemical Formula 1 may each independently be from 0 to 10, and from 1 to 10.

In an exemplary embodiment of the present application, R3 to R10 of Chemical Formula 1 may each independently be hydrogen or heavy hydrogen.

In the present application, the substituents of Chemical Formulas 1 to 7 will be specifically described below.

In the present specification, "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of: heavy hydrogen; a halogen group; -CN; a straight chain or a branch a chain C ₁ to C ₆₀ alkyl group; a straight chain or a branched C ₂ to C ₆₀ alkenyl group; a straight chain or a branched C ₂ to C ₆₀ alkyne group; a monocyclic or polycyclic C ₃ to C ₆₀ ring An alkyl group; a monocyclic or polycyclic C ₂ to C ₆₀ heterocycloalkyl group; a monocyclic or polycyclic C ₆ to C ₆₀ aryl group; a monocyclic or polycyclic C ₂ to C ₆₀ heteroaryl group; a group; -SiRR'R";-P(=O)RR'; a C ₁ to C ₂₀ alkylamine group; a monocyclic or polycyclic C ₆ to C ₆₀ arylamine group; and a single ring Or a polycyclic C ₂ to C ₆₀ heteroarylamine group, or unsubstituted or substituted with one or more substituents bonded to the above two or more substituents, or unsubstituted or linked by two or more substituents as defined above The substituent is substituted. For example, "the substituent to which the above two or more substituents are bonded" may be a biphenyl group. That is, the biphenyl group may also be an aryl group and may be interpreted as a substituent to which a diphenyl group is bonded. Additional substituents may also be substituted. R, R 'and R "are the same or different and are each independently hydrogen lines; deuterium; -CN; of a substituted or unsubstituted straight or branched chain C ₁ to C ₆₀ alkyl group; a substituted or unsubstituted Substituted monocyclic or polycyclic C ₃ to C ₆₀ cycloalkyl groups; monosubstituted or unsubstituted monocyclic or polycyclic C ₆ to C ₆₀ aryl groups; or monosubstituted or unsubstituted monocyclic or polycyclic C ₂ to C ₆₀ heteroaryl groups.

According to an exemplary embodiment of the present application, "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of: heavy hydrogen, monohalogen, -CN, -SiRR'R", -P(=O)RR', a straight or branched C ₁ to C ₂₀ alkyl group, a monocyclic or polycyclic C ₆ to C ₆₀ aryl group, and a single ring or more a C ₂ to C ₆₀ heteroaryl group, and R, R′ and R′′ are the same or different from each other, and each independently is hydrogen; a heavy hydrogen; —CN; a C ₁ to C ₆₀ alkyl group, unsubstituted or heavy hydrogen, a halogen group, -CN, a C ₁ to a C ₂₀ alkyl group, substituted a C ₆ to C ₆₀ aryl group and a C ₂ to C ₆₀ heteroaryl group; a C ₃ To a C ₆₀ cycloalkyl group which is unsubstituted or as a heavy hydrogen, halogen, -CN, a C ₁ to C ₂₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a C ₂ to C ₆₀ heteroaryl group. Substituted; a C ₆ to C ₆₀ aryl group which is unsubstituted or substituted with a heavy hydrogen, a halogen, a -CN, a C1 to C20 alkyl group, a C ₆ to C ₆₀ aryl group, and a C ₂ to C ₆₀ heteroaryl groups substituted by aryl; or a C ₂ to C ₆₀ heteroaryl radical, which system is unsubstituted or deuterium, halogen, -CN, a C ₁ to a C ₂₀ alkyl group , A C ₆ to C ₆₀ aryl group, and a C ₂ to C ₆₀ heteroaryl groups substituted with aryl.

The term "substitution" means to change a hydrogen atom bonded to a carbon atom of a compound to 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, The position at which a substituent may be substituted, and when two or more positions are substituted, the two or more substituents may be the same or different from each other.

In the present specification, the halogen may be fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group includes a straight or branched chain having from 1 to 60 carbon atoms and may be substituted with another substituent. The number of carbon atoms of the alkyl group may range from 1 to 60, specifically from 1 to 40, more specifically from 1 to 20. Specific examples thereof include a monomethyl group, a monoethyl group, a propyl group, a n-propyl group, an isopropyl group, a monobutyl group, a n-butyl group, an isobutyl group, a three a butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, a n-pentyl group, an iso-pentyl group, a new pentane a group, a triamyl group, a monohexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3 , 3-dimethylbutyl group, mono-2-ethylbutyl group, monoheptyl group, mono-heptyl group, 1-methylhexyl group, monocyclopentylmethyl group, monocyclohexylmethyl group , an octyl group, a n-octyl group, a trioctyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentyl group, a n-decyl group, a 2,2-dimethylheptyl group, a 1-ethyl-propyl group, a 1,1-dimethyl-propyl group, an isohexyl group, a 2-methylpentyl group, a 4-methylhexyl group, 5-methylhexyl group and the like, but not limited thereto.

In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms and may be substituted with another substituent. The number of carbon atoms of the alkenyl group may range from 2 to 60, specifically from 2 to 40, more specifically from 2 to 20. Specific examples thereof include a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butene group, a 2-butene group, a 3-butene group, and a 1-pentyl group. An alkenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butene group, a 1,3-butadienyl group, an allyl group, a 1-phenylethene-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylethylene-1-yl group, a 2-phenyl-2-(naphthyl group) -1) an ethylene-1-group, a 2,2-bis(diphenyl-1)ethene-1-yl group, a stilbene group, a styrene group, and the like, but not Limited.

In the present specification, the alkyne group includes a straight or branched chain having 2 to 60 carbon atoms and may be substituted with another substituent. The alkyne group may have a number of carbon atoms of from 2 to 60, specifically from 2 to 40, more specifically from 2 to 20.

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be substituted with another substituent. Here, polycyclic means a group in which a cycloalkyl group is directly bonded or fused to another cyclic group. Here, the other cyclic group may also be a cycloalkyl group, but may be another type of cyclic group, for example, a heterocycloalkyl group, an aryl group, a heteroaryl group, and Similar. The cycloalkyl group may have a carbon atom number of from 3 to 60, specifically from 3 to 40, more specifically from 5 to 20. Specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methyl group. a cyclohexylene group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 1-tetrabutylcyclohexyl group, A cycloheptyl group, a cyclooctyl group, and the like, but not limited thereto.

In the present specification, the heterocycloalkyl group includes O, S, Se, N or Si as a hetero atom, including a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted with another Substituted by the base. Here, polycyclic means a group in which a heterocycloalkyl group is directly bonded or fused to another cyclic group. Here, the other cyclic group may also be a heterocycloalkyl group, but may be another type of cyclic group, for example, a cycloalkyl group, an aryl group, a heteroaryl group, and Similar. The heterocycloalkyl group may have a carbon atom number of 2 to 60, specifically 2 to 40, more specifically 3 to 20.

In the present specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted with another substituent. Here, the polycyclic ring means a group in which an aryl group is directly bonded or fused to another cyclic group. Here, the other cyclic group may also be an aryl group, but may be another type of cyclic group, for example, a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, and Similar. The aryl group includes a helical group. The aryl group may have a carbon atom number of 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group include a monophenyl group, a biphenyl group, a triphenyl group, a naphthyl group, a fluorene group, a decyl group, a phenanthrene group, a fluorene group, and a a fluoranthene group, a monobenzophenanthrene group, a fluorene group, a fluorene group, a tetraalkenyl group, a condensed pentaphenyl group, a fluorene group, a fluorene group, a fluorene group, a benzoindole group, a cyclo-biguanide group, a 2,3-dihydro-1H-indenyl group, a fused cyclic group thereof and the like, but not limited thereto.

In the present specification, the helical group is a group comprising a helical structure and may have from 15 to 60 carbon atoms. For example, the helical group may comprise a structure in which a 2,3-dihydro-1H-indole group or a cyclohexane group is helically bonded to a fluorene group. In particular, the helical group may include a group having any of the following structural formulas.

In the present specification, the heteroaryl group includes O, S, Se, N or Si as a hetero atom, including a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may further have another substituent. Replaced. Here, polycyclic means a group in which a heteroaryl group is directly bonded or fused to another cyclic group. Here, the other cyclic group may also be a heteroaryl group, but may be another type of cyclic group, for example, a cycloalkyl group, a heterocycloalkyl group, an aryl group, and Similar. The heteroaryl group may have a number of carbon atoms of from 2 to 60, specifically from 2 to 40, more specifically from 3 to 25. Specific examples of the heteroaryl group include a pyridyl group, a pyrrole group, a pyrimidine group, a pyridazine group, a furan group, a thiophene group, an imidazolyl group, and a pyrazolyl group. a group, a oxazole group, an isoxazole group, a thiazole group, an isothiazyl group, a triazole group, a monofurazan group, a oxadiazole group, a thiadiazole group a group, a dithiazole group, a tetrazole group, a pyran group, a monothiopyranyl group, a diazinyl group, a monooxazide group, a thiazine group, a diterpene a group, a triazine group, a tetrazine group, a monoquinolyl group, an isoquinolyl group, a quinazoline group, an isoquinazoline group, a quinazoline group, a naphthoquinone group, an acridine group, a phenanthryl group, an imidazopyridine group, a diaza naphthyl group, a triazaindole group, a fluorene group, a fluorene group a pyridyl group, a benzothiazole group, a benzoxazole group, a benzimidazole group, a benzothiophene group, a benzofuran group, a dibenzothiophene group, a two Benzofuran group, monocarbazole group, one a benzoxazole group, a dibenzoxazole group, a phenazine group, a dibenzothiazole group, a spirobis(dibenzothiazole), a dihydrophenazine group, a a phenyloxazinyl group, a phenanthridine group, an imidazopyridine group, a thiophene group, a fluoren [2,3-a]carbazole group, a hydrazine [2,3- b] carbazole group, monoporphyrin porphyrin group, a 10,11-dihydro-dibenzo[b,f]azepinel group, a 9,10-dihydroacridinyl group a phenanthrene group, a phenol thiazide group, a pyridazine group, a naphthyridine group, a monomorpholine group, a monobenzo[c][1,2,5]thiadiazole group, a 5,10-dihydrodibenzo[b,e][1,4]nonazaalkyl group, a pyrazolo[1,5-c]quinazoline group, a pyrido[1,2 -b] carbazole group, monopyrido[1,2-a]imidazo[1,2-e]porphyrin group, a 5,11-dihydroindeno[1,2-b]indole Oxazole groups and the like, but not limited thereto.

In the present specification, the amine group may be selected from the group consisting of: a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; -NH2; a dialkylamine group; a diarylamine group; a diheteroarylamine group; a monoalkylarylamine group; a monoalkylheteroarylamine group; and an arylheteroarylamine group The number of carbon atoms is not particularly limited, but is preferably from 1 to 30. Specific examples of the amine group include a monomethylamine group, a monodimethylamine group, a monoethylamine group, a diethylamine group, a monophenylamine group, a naphthylamino group. Group, monobiphenylamine group, monodiphenylamine group, monodecylamine group, a 9-methyl-decylamine group, a diphenylamine group, a monophenylnaphthalene An amine group, a monomethylamino group, a monophenyltoluene group, a triphenylamine group, a biphenylnaphthylamine group, a monophenylbiphenylamine group, a a biphenyl fluorenylamine group, a phenylbenzophenanthrenylamine group, a monobiphenylbenzophenanthrylamine group, and the like, but not limited thereto.

In the present specification, the arylene group means that there are two bonding sites in one aryl group, that is, a divalent group. The above description for aryl groups applies here, except that the arylene groups are each a divalent group. Further, the heteroarylene group means that there are two bonding sites in a heteroaryl group, that is, a divalent group. The above description for heteroaryl groups is applicable here, except that the heteroarylene groups are each a divalent group.

According to an exemplary embodiment of the present application, Y1 or Y2 of Chemical Formula 1 is And X3 and X4 may be a mono- or unsubstituted aromatic hydrocarbon ring; or a mono- or unsubstituted aromatic heterocyclic ring.

It can be expressed as any of the following structural formulas, but not limited to this.

In these structural formulas, Z ₁ to Z ₃ are the same or different from each other, and each of them is independently S or O, and Z4 to Z9 are the same or different from each other, and each of them is independently CR'R", NR', S Or O, and R' and R" are the same or different from each other, and are each independently hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present application, Chemical Formula 1 may be represented as any of [Group 1] compounds, but is not limited thereto.

[Group 1]

Further, according to an exemplary embodiment of the present application, the chemical formula 1 may be represented by any of the following [Group 2] compounds, but is not limited thereto.

[Group 2]

Further, various substituents may be introduced into the structure of Chemical Formula 1 to synthesize a compound having the intrinsic properties of the introduced substituent. For example, a substituent commonly used for fabricating a hole injection layer in an organic light-emitting device, a transmission hole material, a light-emitting layer material, and an electron transport layer material may be introduced into a core structure to synthesize a condition required for each organic material layer. Material.

Further, various substituents can be introduced into the structure of Chemical Formula 1 to fine tune the band gap, which can additionally improve the characteristics at the interface between the organic materials, and can change the use of such materials.

At the same time, the heterocyclic compound has a high glass transition temperature (Tg) and thus has excellent thermal stability. The increase in thermal stability is an important factor in device drive stability.

Heterocyclic compounds according to an exemplary embodiment of the present application can be prepared via a multi-step chemical reaction. First, some intermediate compounds are prepared, and the compound of Chemical Formula 1 is prepared by using such an intermediate compound. More specifically, the heterocyclic compound according to an exemplary embodiment of the present application can be produced according to the following preparation examples.

Another exemplary embodiment of the present application provides an organic light-emitting device comprising the heterocyclic compound of Chemical Formula 1.

The organic light-emitting device according to an exemplary embodiment of the present application can be made through a general preparation method and material for fabricating an organic light-emitting device, except that the above heterocyclic compound is used to form one or more organic material layers.

In the production of the organic light-emitting device, the heterocyclic compound may be formed not only by a vacuum deposition method but also as a layer of an organic material via a solution coating method. Here, the solution coating method means spin coating, dip coating, jet printing, screen printing, sputtering, roll coating, and the like, but is not limited thereto.

Specifically, an organic light-emitting device according to an exemplary embodiment of the present application includes a positive electrode, a negative electrode, and one or more organic material layers disposed between the positive and negative electrodes, wherein one of the organic material layers Or a multilayer includes the heterocyclic compound represented by Chemical Formula 1.

1 to 3 illustrate a stacking sequence of electrodes and organic material layers in an organic light-emitting device according to an exemplary embodiment of the present application. However, the scope of the present application should not be limited to the drawings, and the structure of the organic light-emitting device known in the art can also be applied to the present application.

The organic light-emitting device shown in FIG. 1 has a positive electrode 200, an organic material layer 300, and a negative electrode 400, which are sequentially stacked on a substrate 100. However, the organic light-emitting device is not limited to such a structure, and as shown in FIG. 2, the organic light-emitting device is sequentially stacked on the substrate with a negative electrode, an organic material layer, and a positive electrode.

The organic material layer illustrated in FIG. 3 is a plurality of layers. The organic light-emitting device of FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light-emitting layer 303, a hole barrier layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited to the above-described stacked structure, and if necessary, other layer bodies other than the light-emitting layer may be omitted, and other necessary functional layers may be further added.

In addition, an organic light-emitting device according to an exemplary embodiment of the present application includes a positive electrode, a negative electrode, and two or more stacked bodies disposed between the positive and negative electrodes, and the two or more stacked systems independently include A light-emitting layer, a charge generation layer is disposed between the two stacks, and the charge generation layer includes the heterocyclic compound represented by Chemical Formula 1.

In addition, an organic light-emitting device according to an exemplary embodiment of the present application includes a positive electrode, a first stacked body (provided on the positive electrode and including a first light-emitting layer), and a charge generating layer (provided in the first a second stack (on the charge generation layer and including a second light-emitting layer) and a negative electrode (on the second stack). In this case, the charge generating layer may include a heterocyclic compound represented by Chemical Formula 1. Furthermore, the first stacked body and the second stacked body may each independently further comprise one or more of the above-mentioned hole injection layer, hole transport layer, hole barrier layer, electron transport layer, electron injection layer, and the like. By.

The charge generating layer may be an N type charge generating layer, and the charge generating layer may further include a dopant known in the art in addition to the heterocyclic compound represented by Chemical Formula 1.

4 is a schematic diagram showing an organic light-emitting device having a two-series stack structure according to an exemplary embodiment of the present application.

In this embodiment, the first electronic barrier layer, the first hole barrier layer, the second hole barrier layer, and the like shown in FIG. 4 may be omitted.

The organic light-emitting device of the present invention can be produced by materials and methods known in the art, except that one or more of the organic material layers include the heterocyclic compound represented by Chemical Formula 1.

The heterocyclic compound represented by Chemical Formula 1 may constitute one or more organic material layers in the organic light-emitting device alone. However, if necessary, the heterocyclic compound represented by Chemical Formula 1 may be mixed with another material to constitute an organic material layer.

The heterocyclic compound represented by Chemical Formula 1 can be used as a material of an electron transporting layer, a hole blocking layer, a light emitting layer and the like in the organic light-emitting device. For example, the heterocyclic compound represented by Chemical Formula 1 can be used as a material of an electron transport layer, a hole transport layer or a light-emitting layer in an organic light-emitting device.

Further, the heterocyclic compound represented by Chemical Formula 1 can be used as a material of a light-emitting layer in an organic light-emitting device. For example, the heterocyclic compound represented by Chemical Formula 1 can be used as a material of the phosphorescent host of the light-emitting layer in the organic light-emitting device.

Hereinafter, other materials than the chemical formula 1 heterocyclic compound in the organic light-emitting device will be described in accordance with an exemplary embodiment of the present application, but such materials are merely illustrative and should not be construed as limiting the scope of the present application, and may be Substituting materials known in the art to replace them.

The material of the positive electrode may use a material having a higher work function, for example, a transparent conductive oxide, a metal or a conductive polymer, and the like may be used. Specific examples of the positive electrode material include: a metal such as vanadium, chromium, copper, zinc, and gold or an alloy thereof; a metal oxide 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; a conductive polymer such as poly(3-methyl compound), poly[3,4-(ethylene-1,2-dioxy) Compounds] (PEDOT), polypyrrole and polyaniline and the like, but not limited thereto.

As the material of the negative electrode, a material having a lower work function can be used, and for example, a metal, a metal oxide or a conductive polymer and the like can be used. Specific examples of the negative electrode material include: a metal such as magnesium, calcium, sodium, potassium, titanium, indium, lanthanum, lithium, lanthanum, aluminum, silver, tin, and lead or an alloy thereof; and a multilayer structural material such as LiF/ Al or LiO ₂ /Al and the like, but not limited thereto.

The hole injecting material may also be a hole injecting material known in the art, and may be, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or as a document [Advanced Material, 6, p. A stellate amine derivative as described in 677 (1994)], for example, tris(4-oxazolyl-9-phenyl)amine (TCTA), 4,4',4"-tris[phenyl (m- Tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/ten Dialkylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate), which is a soluble conductive polymer, polyaniline/camphorsulfonic acid or polyaniline /Poly(4-styrenesulfonate) and the like.

The hole transporting material may use a pyrazoline derivative, an arylamine derivative, a monoterpene derivative, a triphenyldiamine derivative, and the like, and may also use a low molecular weight material or a polymer material. .

The electron transporting material may use an oxadiazole derivative, quinodimethane and its derivatives, benzopyrene and its derivatives, naphthoquinone and its derivatives, hydrazine and its derivatives, tetracyanoquinone Methane and its derivatives, monoterpene derivatives, diphenyldicyanoethylene and its derivatives, monohydric phenolphthalein derivatives, 8-hydroxyquinoline metal complexes and derivatives thereof, and the like, A low molecular weight material and a polymeric material are used.

The electron injecting material is generally used by a user in the art, for example, LiF, but the present application is not limited thereto.

The luminescent material may be a red, green or blue luminescent material, and if necessary, two or more luminescent materials may be used in combination. Further, the fluorescent material may be used as a light-emitting material, but a phosphorescent material may also be used. As the luminescent material, a material which emits light by combining holes and electrons respectively injected from the positive and negative electrodes may be used alone, but a material which emits light by the interaction of the host material and the dopant material may also be used.

The organic light-emitting device according to an exemplary embodiment of the present application may be of a top emission type, a bottom emission type, or a dual emission type depending on materials used.

The heterocyclic compound according to an exemplary embodiment of the present application can be operated using an operation principle similar to that of an organic light-emitting device, even an organic electronic device including an organic solar cell, an organic photoconductor, an organic transistor, and the like.

The invention is illustrated by the following examples, which are intended to be illustrative only and not to limit the scope of the application.

< Instance >

1. Group 1 Preparation of compounds

< Preparation Example 1> Preparation of Compound 1

1) Compound 1-1 Preparation

After dissolving 2-fluoronitrobenzene (1 equivalent) in 600 ml of DMF, hydrazine (1 equivalent) was added thereto, followed by addition of cesium carbonate (2.3 equivalent), and then the resulting mixture was stirred at room temperature for 18 hours. . When the reaction was completed, cesium carbonate was filtered off with a filter paper, and then the filtrate was extracted with ethyl acetate and H ₂ O. After the extraction, the filtrate was separated and purified by column chromatography to give Compound 1-1.

2) Compound 1-2 Preparation

Compound 1-1 (1 equivalent) was dissolved in ethanol and H ₂ O (ratio 10: 7), then ammonium chloride (4 equivalents) and iron (5 equivalents) were added thereto, and the resulting mixture was heated for 3 hours. When the reaction was completed, the solvent was concentrated, and then extracted with ethyl acetate and H ₂ O. After the extraction, the extract was separated and purified by column chromatography to obtain Compound 1-2.

3) Compound 1 Preparation

Compound 1-2 (1 equivalent) was dissolved in 500 ml of toluene. 1-naphthaldehydride (1.1 equivalent) and p-toluenesulfonic acid (0.1 equivalent) were added thereto, and the resulting mixture was heated for 24 hours. When the reaction was completed, extraction was carried out using dichloromethane and H ₂ O. After the extraction, the extract was separated and purified by column chromatography, whereby Compound 1 was obtained.

< Preparation Example 2> Preparation of Compound 2

1) Compound 1-1 Preparation

Compound 1-1 was prepared in the same manner as in the preparation of Compound 1-1 of Example 1.

2) Compound 1-2 Preparation

Compound 1-2 was prepared in the same manner as in the preparation of Compound 1-2 of Preparation Example 1.

3) Compound 2 Preparation

Compound 1-2 (1 equivalent) was dissolved in 500 ml of toluene. A 2-naphthol anhydrate (1.1 equivalent) and p-toluenesulfonic acid (0.1 equivalent) were added thereto, and the resulting mixture was heated for 24 hours. When the reaction was completed, extraction was carried out using dichloromethane and H ₂ O. After the extraction, the extract was separated and purified by column chromatography, whereby Compound 2 was obtained.

< Preparation Example 3> Preparation of a compound having a substituent of the following Table 1

1) Compound 1-1 Preparation

Compound 1-1 was prepared in the same manner as in the preparation of Compound 1-1 of Example 1.

2) Compound 1-2 Preparation

Compound 1-2 was prepared in the same manner as in the preparation of Compound 1-2 of Preparation Example 1.

3) Compound 1-3 Preparation

Compound 1-2 (1 equivalent) was dissolved in 500 ml of toluene. 4-Bromobenzaldehyde (1.1 equivalents) and p-toluenesulfonic acid (0.1 equivalents) were added thereto, and the resulting mixture was heated for 24 hours. When the reaction was completed, extraction was carried out using dichloromethane and H ₂ O. After the extraction, the extract was separated and purified by column chromatography, whereby Compound 1-3 was obtained.

4) Compound 1-4 Preparation

Compound 1-3 (1 equivalent) was dissolved in 500 ml of 1,4-dioxane. 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborane (2 equivalents), potassium acetate ( 3 equivalents) and PdCl 2 (dppf) (0.05 equivalents) were added thereto, and the resulting mixture was heated for 4 hours.

When the reaction was completed, extraction was carried out using dichloromethane and H 2 O. After the extraction, the extract was separated and purified by column chromatography, whereby Compound 1-4 was obtained.

5) Compound P3 Preparation

Compound 1-4 (2.2 eq.) was dissolved in 1,4-dioxane and H ₂ O (ratio 4:1), then Pd(PPh ₃ ) ₄ (0.05 eq.), K ₂ CO ₃ (3 eq.) And the compound S-1 (1 equivalent) was added thereto, and the resulting mixture was heated for 4 hours. When the reaction was completed, extraction was carried out using dichloromethane and H ₂ O. After the extraction, the extract was separated and purified by column chromatography to obtain a target compound P3 (yield: 42 to 75%).

[Table 1]

< Preparation Example 4> Preparation of a compound having a substituent of the following Table 2

1) Compound 1-1 Preparation

Compound 1-1 was prepared in the same manner as in the preparation of Compound 1-1 of Preparation Example 1.

2) Compound 1-2 Preparation

Compound 1-2 was prepared in the same manner as in the preparation of Compound 1-2 of Preparation Example 1.

3) Compound 1-3 Preparation

Compound 1-2 (1 equivalent) was dissolved in 500 ml of toluene. 3-Bromobenzaldehyde (1.1 equivalent) and p-toluenesulfonic acid (0.1 equivalent) were added thereto, and the resulting mixture was heated for 24 hours. When the reaction was completed, extraction was carried out using dichloromethane and H ₂ O. After the extraction, the extract was separated and purified by column chromatography, whereby Compound 1-3 was obtained.

4) Compound 1-4 Preparation

Compound 1-3 (1 equivalent) was dissolved in 500 ml of 1.4-dioxane. 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborane (2 equivalents), potassium acetate ( 3 equivalents) and PdCl ₂ (dppf) (0.05 equivalents) were added thereto, and the resulting mixture was heated for 4 hours.

When the reaction was completed, extraction was carried out using dichloromethane and H ₂ O. After the extraction, the extract was separated and purified by column chromatography, whereby Compound 1-4 was obtained.

5) Compound P4 Preparation

Compound 1-4 (2.2 eq.) was dissolved in 1,4-dioxane and H ₂ O (ratio 4:1), then Pd(PPh ₃ ) ₄ (0.05 eq.), K ₂ CO ₃ (3 eq.) And the compound S-1 (1 equivalent) was added thereto, and the resulting mixture was heated for 4 hours. When the reaction was completed, extraction was carried out using dichloromethane and H ₂ O. After the extraction, the extract was separated and purified by column chromatography to obtain a target compound P4 (yield: 43 to 78%).

[Table 2]

< Preparation Example 5> Preparation of Compound 18

1) Compound 1-1 Preparation

Compound 1-1 was prepared in the same manner as in the preparation of Compound 1-1 of Example 1.

2) Compound 1-2 Preparation

Compound 1-2 was prepared in the same manner as in the preparation of Compound 1-2 of Preparation Example 1.

3) Compound 1-3 Preparation

Compounds 1-3 were prepared in the same manner as in the preparation of the compound 1-3 of Example 3.

4) Compound 18 Preparation

Compound 1-3 (1 eq.) was dissolved in 50 mL of dry THF and the resulting solution was then cooled to -78. n-Butyllithium (2.5 in hexane, 1 equivalent) was slowly added dropwise thereto, and the resulting mixture was stirred for 1 hour. Diphenylphosphonium chloride (1 equivalent) was added dropwise to the solution, and the reaction solution was stirred at room temperature for 12 hours. The reaction mixture was extracted using MC/H ₂ O and then distilled under reduced pressure. The reaction mixture was dissolved in MC (250 ml), and then the reaction mixture was stirred with 20 ml of 30% aqueous H ₂ O ₂ at room temperature for 1 hour. The reaction mixture was extracted with MC/H ₂ O, and then the concentrated mixture was separated by column chromatography (SiO ₂ , MC : methanol = 25 : 1 ) to give a target compound 18 in a yield of 22%.

< Preparation Example 6> Preparation of Compound 98

1) Compound 1-1 Preparation

Compound 1-1 was prepared in the same manner as in the preparation of Compound 1-1 of Preparation Example 1.

2) Compound 1-2 Preparation

Compound 1-2 was prepared in the same manner as in the preparation of Compound 1-2 of Preparation Example 1.

3) Compound 1-3 Preparation

Compound 1-3 was prepared in the same manner as in the preparation of Compound 1-3 of Example 4.

4) Compound 98 Preparation

Compound 1-3 (1 eq.) was dissolved in 50 mL of dry THF and the resulting solution was then cooled to -78. n-Butyllithium (2.5 equivalents in hexane) was slowly added dropwise thereto, and the resulting mixture was stirred for 1 hour. Diphenylphosphonium chloride (1 equivalent) was added dropwise to the solution, and the reaction solution was stirred at room temperature for 12 hours. The reaction mixture was extracted using MC/H ₂ O and then distilled under reduced pressure. The reaction mixture was dissolved in MC (250 ml), and then the reaction mixture was stirred with 20 ml of 30% aqueous H ₂ O ₂ at room temperature for 1 hour. The reaction mixture was extracted with MC/H ₂ O, and then the concentrated mixture was separated by column chromatography (SiO ₂ , MC : methanol = 25 : 1) to afford a target compound 98 (yield 22%).

< Preparation Example 7> Preparation of Compound 146

1) Compound A-1 Preparation

(9,9-Dimethyl-9H-indol-2-yl)boronic acid (2 equivalents), 1-bromo-2-nitrobenzene (1 equivalent), Pd(PPh ₃ ) ₄ (0.05 equivalents) A mixture of K ₂ CO ₃ (2 eq.) in THF (250 mL) / H ₂ O (50 mL) was refluxed in a single-necked round bottom flask and stirred for 24 hours. Removing the aqueous layer, the organic layer was then dried with MgSO _4. After concentration, the mixture was separated by column chromatography (SiO ₂ , hexane : MC = 2 : 1) to afford a yellow solid compound A-1.

2) Compound A-2 Preparation

Compound A-1 (1 eq) and the mixture was stirred at reflux with PPh _{3 (3} eq.) Of o-DCB (300 mL) in a single neck round bottom flask under nitrogen. The o-DCB was distilled off under vacuum, and then the reaction product (SiO ₂ , hexane : MC = 3 : 1) was separated by column chromatography to give a white solid compound A-2.

3) Compound 1-1 Preparation

Compound 1-1 was prepared in the same manner as in the preparation of Compound 1-1 of Example 1.

4) Compound 1-2 Preparation

Compound 1-2 was prepared in the same manner as in the preparation of Compound 1-2 of Preparation Example 1.

5) Compound 1-3 Preparation

Compound 1-3 was prepared in the same manner as in the preparation of Compound 1-3 of Example 3.

6) Compound P7 Preparation

Compound 1-3 (1 equivalent), compound A-2 (2 equivalents), Cu (0.05 equivalent), 18-crown-6-ether (0.05 equivalent) and K ₂ CO ₃ (2 equivalents) of o-DCB ( The 80 ml) mixture was refluxed in a single neck round bottom flask under nitrogen and stirred for 12 hours. The o-DCB was distilled and removed under vacuum, and then the reaction product was separated by column chromatography (SiO ₂ , hexane : MC = 4:1) to give a desired compound P7, yield 54%.

< Preparation Example 8> Preparation of Compound 165

1) Compound B-1 Preparation

Sulfuric acid (1 eq.) was slowly added dropwise to a 1,2-dicyclohexanone (1 eq.) and phenylhydrazine hydrochloride (2 eq.) of ethanol in a single neck round bottom flask under nitrogen (1,000 equivalents). The mixture was stirred in ML and then the resulting mixture was stirred at 60 ° C for 4 hours. The solution cooled to room temperature was filtered to give a tan solid.

Trifluoroacetic acid (2 eq.) was placed in a mixture of the solid (68.9 g, 0.25 m) and acetic acid (700 ml) in a single-necked round bottom flask, and the resulting mixture was stirred at 100 ° C for 15 hours. The solution cooled to room temperature was filtered and washed with acetic acid and hexane to give an ivory solid B-1.

2) Compound B-2 Preparation

Compound B-1 (1 equivalent), iodobenzene (1.5 equivalents), Cu (0.05 equivalent), 18-crown-6-ether (0.05 equivalent) and K ₂ CO ₃ (2 equivalents) of o-DCB (20 ml) The mixture was refluxed in a double necked round bottom flask under nitrogen and stirred for 16 hours. The solution which was cooled to room temperature was extracted with MC/H ₂ O and concentrated, and then separated by column chromatography (SiO ₂ , hexane : ethyl acetate = 10 : 1) to afford Compound Compound B-2 as white solid.

3) Compound 1-1 Preparation

Compound 1-1 was prepared in the same manner as in the preparation of Compound 1-1 of Example 1.

4) Compound 1-2 Preparation

Compound 1-2 was prepared in the same manner as in the preparation of Compound 1-2 of Preparation Example 1.

5) Compound 1-3 Preparation

Compounds 1-3 were prepared in the same manner as in the preparation of the compound 1-3 of Example 3.

6) Compound 165 Preparation

Compound 1-3 (1 equivalent), compound A-2 (2 equivalents), Cu (0.05 equivalent), 18-crown-6-ether (0.05 equivalent) and K ₂ CO ₃ (2 equivalents) of o-DCB ( The 80 ml) mixture was refluxed in a single neck round bottom flask under nitrogen and stirred for 12 hours. The o-DCB was distilled and removed under vacuum, and then the product was separated by column chromatography (SiO ₂ , hexane : MC = 4:1) to give a target compound 165 (yield 51%).

The compounds were prepared in the same manner as in the preparation of the preparation examples, and the results of the synthesis confirmation are shown in the following list. Table 3 shows the field desorption mass spectrometry (FD-MS) measurements, and Table 4 shows the NMR values.

[table 3]

[Table 4]

Figure 5 is a plot of PL measurement of Compound 16 at a wavelength of 286 nm.

Figure 6 is a graph of PL measurement of Compound 16 at a wavelength of 328 nm.

Figure 7 is a plot of PL measurement of compound 16 at a wavelength of 404 nm.

Figure 8 is a graph of PL measurement of compound 209 at a wavelength of 239 nm.

Figure 9 is a plot of PL of compound 209 at a wavelength of 292 nm.

Figure 10 is a plot of PL of compound 209 at a wavelength of 338 nm.

Figure 11 is a plot of PL of compound 209 at a wavelength of 408 nm.

Figure 12 is a graph of PL measurement of Compound 44 at a wavelength of 280 nm.

Figure 13 is a plot of PL of compound 44 at a wavelength of 414 nm.

2. Group 2 Preparation of compounds

< Preparation Example 9> Preparation of a compound having a substituent of the following Table 5

1) Compound 1-1 Preparation

The hydrazine (1 equivalent) was placed in a one-neck round bottom flask, and (4-bromophenyl) hydrazine (1.2 eq.) was dissolved in 500 ml of PhCl, followed by Pd(OAc) ₂ (0.01 eq.). F ₃ CCO ₂ H (1 equivalent) and 10-phenanthroline (0.5 equivalent) were added thereto, and the resulting mixture was heated for 5 hours. When the reaction was completed, extraction was carried out with ethyl acetate and H ₂ O. After the extraction, the extract was separated and purified by column chromatography to give Compound 1-1.

2) Compound 1-2 Preparation

After dissolving 2-fluoronitrobenzene (1 equivalent) in 600 ml of DMF, compound 1-1 (1 equivalent) was added thereto, followed by cesium carbonate (2.3 equivalent), and the resulting mixture was stirred at room temperature. hour. When the reaction was completed, cesium carbonate was filtered off with a filter paper, and then the filtrate was extracted with ethyl acetate and H ₂ O. After the extraction, the extract was separated and purified by column chromatography to obtain Compound 1-2.

3) Compound 1-3 Preparation

Compound 1-2 (1 equivalent) was dissolved in ethanol and H ₂ O (10:7 ratio), then ammonium chloride (4 equivalents) and iron (5 equivalents) were successively added, and the resulting mixture was heated for 3 hours. When the reaction was completed, the solvent was concentrated, and then extracted with ethyl acetate and H ₂ O. After the extraction, the extract was separated and purified by column chromatography, whereby Compound 1-3 was obtained.

4) Compound 1-4 Preparation

Compound 1-3 (1 equivalent) was dissolved in 500 ml of toluene. Formaldehyde (1.1 equivalents) and p-toluenesulfonic acid (0.1 equivalents) were added thereto, and the resulting mixture was heated for 24 hours. When the reaction was completed, extraction was carried out using dichloromethane and H ₂ O. After the extraction, the extract was separated and purified by column chromatography, whereby Compound 1-4 was obtained.

5) Compound 1-5 Preparation

Compound 1-4 (1 equivalent) was dissolved in 500 ml of 1,4-dioxane. 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborane (2 equivalents), potassium acetate ( 3 equivalents) and PdCl ₂ (dppf) (0.05 equivalents) were added thereto, and the resulting mixture was heated for 4 hours.

When the reaction was completed, extraction was carried out using dichloromethane and H ₂ O. After the extraction, the extract is separated and purified by column chromatography, whereby Compound 1-5 is obtained.

6) Compound P8 Preparation

Compound 1-5 (2.2 eq.) was dissolved in 1,4-dioxane and H ₂ O (ratio 4:1), then Pd(PPh ₃ ) ₄ (0.05 eq.), K ₂ CO ₃ (3 eq. And the compound S-1 (1 equivalent) was added thereto, and the resulting mixture was heated for 4 hours. When the reaction was completed, extraction was carried out using dichloromethane and H ₂ O. After the extraction, the extract was separated and purified by column chromatography to obtain a target compound P8 (yield: 43 to 82%).

[table 5]

< Preparation Example 10> Preparation of a compound having a substituent of the following Table 6

1) Compound 1-1 Preparation

The hydrazine (1 equivalent) was placed in a one-neck round bottom flask, and (3-bromophenyl) hydrazine (1.2 eq.) was dissolved in 500 ml of PhCl, followed by Pd(OAc) ₂ (0.01 eq.). F ₃ CCO ₂ H (1 eq.) and 10- phenanthroline (0.5 eq.), and the resulting mixture was heated for 5 hr. When the reaction was completed, extraction was carried out using ethyl acetate and H ₂ O. After the extraction, the extract was separated and purified by column chromatography, whereby Compound 1-1 was obtained.

2) 1-2 Preparation of compounds

Compound 1-2 was prepared in the same manner as in the preparation of Compound 1-2 of Preparation Example 1.

3) Compound 1-3 Preparation

Compound 1-3 was prepared in the same manner as in the preparation of the compound 1-3 of Example 1.

4) Compound 1-4 Preparation

Compounds 1-4 were prepared in the same manner as in the preparation of the compound 1-4 of Example 1.

5) Compound 1-5 Preparation

Compound 1-5 was prepared in the same manner as in the preparation of the compound 1-5 of Example 1.

6) Compound P9 Preparation

Compound 1-5 (2.2 equivalents) was dissolved in 1,4-dioxane and H ₂ O (ratio 4:1), followed by Pd(PPh ₃ ) ₄ (0.05 equivalents), K ₂ CO ₃ (3 equivalents) And compound S-1 (1 equivalent), and the resulting mixture was heated for 4 hours. When the reaction was completed, extraction was carried out using dichloromethane and H ₂ O. After the extraction, the extract was separated and purified by column chromatography to obtain a target compound P9 (yield: 43 to 78%).

[Table 6]

< Preparation Example 11> Preparation of Compound 237

1) Compound 1-1 Preparation

Compound 1-1 was prepared in the same manner as in the preparation of Compound 1-1 of Example 9.

2) Compound 1-2 Preparation

Compound 1-2 was prepared in the same manner as in the preparation of Compound 1-2 of Example 9.

3) Compound 1-3 Preparation

Compound 1-3 was prepared in the same manner as in the preparation of Compound 1-3 of Example 9.

4) Compound 1-4 Preparation

Compounds 1-4 were prepared in the same manner as in the preparation of the compound 1-4 of Example 9.

5) Compound 237 Preparation

Compound 1-4 (1 equivalent) was dissolved in 50 mL of dry THF and then the resulting solution was cooled to -78 °C. n-Butyllithium (2.5 in hexane, 1 equivalent) was slowly added dropwise thereto, and the resulting mixture was stirred for 1 hour. Diphenylphosphonium chloride (1 equivalent) was added dropwise to the solution, and the reaction solution was stirred at room temperature for 12 hours. The reaction mixture was extracted with MC/H ₂ O and then distilled under vacuum. The reaction mixture was dissolved in MC (250 ml), and then the reaction mixture was stirred with 20 ml of 30% aqueous H ₂ O ₂ at room temperature for 1 hour. The reaction mixture was extracted with MC/H ₂ O, and then the concentrated mixture was separated by column chromatography (SiO ₂ , MC : methanol = 25 : 1 ) to yield a title compound 237 (yield: 58%).

< Preparation Example 12> Preparation of Compound 317

1) Compound 1-1 Preparation

Compound 1-1 was prepared in the same manner as in the preparation of Compound 1-1 of Example 10.

2) Compound 1-2 Preparation

Compound 1-2 was prepared in the same manner as in the preparation of Compound 1-2 of Example 10.

3) Compound 1-3 Preparation

Compound 1-3 was prepared in the same manner as in the preparation of Compound 1-3 of Example 10.

4) Compound 1-4 Preparation

Compounds 1-4 were prepared in the same manner as in the preparation of the compound 1-4 of Example 10.

5) Compound 317 Preparation

Compound 1-4 (1 equivalent) was dissolved in 50 mL of dry THF and then the resulting solution was cooled to -78 °C. n-Butyllithium (2.5 equivalents in hexane) was slowly added dropwise thereto, and the resulting mixture was stirred for 1 hour. Diphenylphosphonium chloride (1 equivalent) was added dropwise to the solution, and the reaction solution was stirred at room temperature for 12 hours. The reaction mixture was extracted with MC/H ₂ O and then distilled under vacuum. The reaction mixture was dissolved in MC (250 ml), and then the reaction mixture was stirred with 20 ml of 30% aqueous H ₂ O ₂ at room temperature for 1 hour. The reaction mixture was extracted with MC/H ₂ O, and then the concentrated mixture was separated by column chromatography (SiO ₂ , MC : methanol = 25 : 1 ) to yield the title compound 317 (yield: 62%).

The compounds were prepared in the same manner as in the preparation of the preparation examples, and the results of the synthesis confirmation are shown in the following list. Table 7 shows field desorption mass spectrometry (FD-MS) measurements, and Table 8 shows NMR values.

[Table 7]

[Table 8]

< Experimental example 1> Use group 1 Compound organic light-emitting device

1) Manufacture of organic light-emitting devices

The glass substrate on which the 1500 Å thick ITO was thinly coated was ultrasonically cleaned using distilled water. After the completion of the washing with distilled water, the glass substrate is ultrasonically cleaned using a solvent such as acetone, methanol or isopropyl alcohol, dried, and then sent to a UV cleaner for UV-treatment for 5 minutes. The substrate is then fed to a plasma cleaner (PT), subjected to plasma treatment, and the ITO work function is performed under vacuum and the residual film is removed and sent to a thermal deposition apparatus for organic deposition.

An organic material having a 2-stack white organic light-emitting device (WOLED) structure was formed on the ITO transparent electrode (positive electrode). In the first stack, the TAPC was first thermally deposited to a thickness of 300 Å under vacuum to form a hole transport layer. After the hole transport layer is formed, a light-emitting layer is thermally deposited thereon under vacuum in the following manner. The host layer TCz1 was doped with a concentration of 8% blue phosphorescent dopant FIrpic, and the luminescent layer was deposited to a thickness of 300 Å. An electron transport layer having a thickness of 400 Å was formed using TmPyPB, and then the compound in the following Table 7 was doped with Cs ₂ CO _{3 having} a concentration of 20% to form a charge generating layer having a thickness of 100 Å.

In the second stack, the thickness of MoO ₃ to 50 Å is first thermally deposited under vacuum to form a hole injection layer. The TAPC is doped with MoO ₃ at a concentration of 20%, and the thickness of TAPC is deposited to 300 Å, thereby forming a common hole transport layer of 100 Å thickness, and doping the body with a green phosphorescent dopant Ir(ppy) _{3 of} 8% concentration. TCz1 deposits a 300 Å thick luminescent layer on a common hole transport layer and then uses TmPyPB to form an electron transport layer with a thickness of 600 Å. Finally, a 10 Å thick lithium fluoride (LiF) is deposited on the electron transport layer to form an electron injection layer, and then a 1,200 Å thick aluminum (Al) negative electrode is deposited on the electron injection layer to form a negative electrode. An organic light-emitting device is thus fabricated.

At the same time, all the organic compounds required for the fabrication of the OLED device are subjected to vacuum sublimation purification at 10 ^-6 to 10 ^-8 torr and used to manufacture OLEDs.

2) Driving voltage and luminous efficiency of organic light-emitting device

The electroluminescence (EL) characteristics of the above-described organic light-emitting device were measured using M7000 manufactured by McScience Inc., and the lifetime measurement device (M6000) manufactured by McScience Inc. was used, and the reference luminance was evaluated to be 3,500 cd/m ² based on the measurement result. T ₉₅ . The measurement results of the white organic light-emitting device manufactured according to the present invention in terms of driving voltage, luminous efficiency, external quantum efficiency, and chromaticity coordinates (CIE) are shown in Table 9.

[Table 9]

As is apparent from the results of Table 9, the organic light-emitting device using the charge generating layer material of the present invention 2 stacked body white organic light-emitting device had a lower driving voltage and improved luminous efficiency as compared with Comparative Example 1.

The reason for this improvement is that the skeleton of the present invention has an appropriate length and strength and smoothness, and the compound of the present invention is used as an N-type charge generating layer composed of a suitable hetero compound capable of bonding with a metal, doping one. The alkali metal or alkaline earth metal forms an energy gap state in the N-type charge generation layer, and it is determined that electrons generated by the P-type charge generation layer can be easily introduced into the electron transport layer via the energy gap state generated in the N-type charge generation layer. Therefore, the P-type charge generating layer allows electrons to be smoothly introduced and transferred to the N-type charge generating layer, thereby lowering the driving voltage of the organic light-emitting device and improving the efficiency and lifetime.

< Experimental example 2> Use group 1 Compound organic light-emitting device

1) Manufacture of organic light-emitting devices

The glass transparent electrode ITO film (manufactured by Samsung-Corning Co., Ltd.) for OLED was washed with trichloroethylene, acetone, ethanol, and distilled water for 5 minutes, and then the ITO film was placed in isopropyl alcohol. Then use it.

Subsequently, an ITO substrate was placed in a substrate holder of a vacuum deposition apparatus, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) ) Put it in one of the vacuum deposition equipment.

The air in the emptying tank is followed until the vacuum in the tank reaches 10 ^-6 Torr, and then the current is passed into a small cell to volatilize 2-TNATA, thereby depositing a hole injection layer having a thickness of 600 Å on the ITO substrate.

The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) is placed in another cell of the vacuum deposition apparatus and a current is passed into the The small grid volatilizes the NPB, thereby depositing a hole transport layer having a thickness of 300 Å on the hole injection layer.

The hole injection layer and the hole transport layer are formed as above, and then a blue light-emitting material having the following structure is deposited thereon as a light-emitting layer. Specifically, the blue light-emitting host material H1 is vacuum-deposited to a thickness of 200 Å in one of the vacuum deposition apparatuses, and then the blue light-emitting dopant material D1 is vacuum-deposited thereon in an amount relative to the main body. 5% of the material.

Subsequently, a compound having the following structural formula E1 was deposited to a thickness of 300 Å as an electron transport layer.

Lithium fluoride (LiF) having a thickness of 10 Å was deposited as an electron injecting layer, and the thickness of the Al negative electrode was 1,000 Å, thereby fabricating an OLED device.

At the same time, all the organic compounds required for the fabrication of the OLED device were subjected to vacuum sublimation purification at 10 ^-6 to 10 ^-8 Torr and used to manufacture OLEDs.

2) Driving voltage and luminous efficiency of organic light-emitting device

The electroluminescence (EL) characteristics of the above-described organic light-emitting device were measured using M7000 manufactured by McScience Inc., and the lifetime measurement device (M6000) manufactured by McScience Inc. was used, and the reference luminance was evaluated to be 700 cd/m ² based on the measurement result. T ₉₅ . The measurement results of the organic light-emitting device manufactured according to the present invention in terms of driving voltage, luminous efficiency, external quantum efficiency, and chromaticity coordinates (CIE) are shown in Table 10.

[Table 10]

As is apparent from the results of Table 10, the organic light-emitting device using the electron-transporting layer material of the blue organic light-emitting device of the present invention has a lower driving voltage than that of Comparative Example 2, and can significantly improve luminous efficiency and lifetime.

The reason for this improvement is that the compound of the present invention has an appropriate length and strength and smoothing properties. When used as an electron transporting layer, it accepts electrons under specific conditions to produce a compound in an excited state, and in particular, when a compound When the hybrid skeleton site forms an excited state, the excited energy moves to a stable state, and then the excited hybrid skeleton site undergoes another reaction, and in the relatively stable compound, the compound does not decompose or destroy, And the electrons can be transmitted efficiently. For reference only, the compound having a stable state upon excitation should be an aryl or acene compound or a polycyclic compound. Therefore, the compound of the present invention can improve electron transport characteristics or stability, and exhibit excellent performance in terms of driving, efficiency, and life.

< Experimental example 3> Use group 2 Compound organic light-emitting device

1) Manufacture of organic light-emitting devices

The glass substrate on which the 1500 Å thick ITO was thinly coated was ultrasonically cleaned using distilled water. After the completion of the washing with distilled water, the glass substrate is ultrasonically cleaned using a solvent such as acetone, methanol or isopropyl alcohol, dried, and then sent to a UV washing machine for UV-treatment with UV for 5 minutes. The substrate is then fed to a plasma cleaner (PT), subjected to plasma treatment, and the ITO work function is performed under vacuum and the residual film is removed and sent to a thermal deposition apparatus for organic deposition.

An organic material having a 2-stack white organic light-emitting device (WOLED) structure was formed on the ITO transparent electrode (positive electrode). In the first stack, the TAPC was first thermally deposited to a thickness of 300 Å under vacuum to form a hole transport layer. After the hole transport layer is formed, a light-emitting layer is thermally deposited thereon under vacuum in the following manner. The host layer TCz1 was doped with a concentration of 8% blue phosphorescent dopant FIrpic, and the luminescent layer was deposited to a thickness of 300 Å. An electron transport layer having a thickness of 400 Å was formed using TmPyPB, and then the compound in the following Table 5 was doped with Cs ₂ CO ₃ at a concentration of 20% to form a charge generating layer having a thickness of 100 Å.

In the second stack, the thickness of MoO ₃ to 50 Å is first thermally deposited under vacuum to form a hole injection layer. The TAPC is doped with MoO ₃ at a concentration of 20%, and the thickness of TAPC is deposited to 300 Å, thereby forming a common hole transport layer of 100 Å thickness, and doping the body with a green phosphorescent dopant Ir(ppy) _{3 of} 8% concentration. TCz1, on which a thickness of 300 Å is deposited, and then TmPyPB is used to form an electron transport layer having a thickness of 600 Å. Finally, a 10 Å thick lithium fluoride (LiF) is deposited on the electron transport layer to form an electron injection layer, and then a 1,200 Å thick aluminum (Al) negative electrode is deposited on the electron injection layer to form a negative electrode. An organic light-emitting device is thus fabricated.

At the same time, all the organic compounds required for the fabrication of the OLED device were subjected to vacuum sublimation purification at 10 ^-6 to 10 ^-8 Torr and used to manufacture OLEDs.

2) Driving voltage and luminous efficiency of organic light-emitting device

The electroluminescence (EL) characteristics of the above-described organic light-emitting device were measured using M7000 manufactured by McScience Inc., and the lifetime measurement device (M6000) manufactured by McScience Inc. was used, and the reference luminance was evaluated to be 3,500 cd/m ² based on the measurement result. T ₉₅ . The measurement results of the white organic light-emitting device manufactured according to the present invention in terms of driving voltage, luminous efficiency, external quantum efficiency, and chromaticity coordinates (CIE) are shown in Table 11.

[Table 11]

As is apparent from the results of Table 11, the organic light-emitting device using the charge generating layer material of the present invention 2 stacked white organic light-emitting device had a lower driving voltage and improved luminous efficiency as compared with Comparative Example 3. The reason for this improvement is that the skeleton of the present invention has an appropriate length and strength and smoothness, and the compound of the present invention is used as an N-type charge generating layer composed of a suitable hetero compound capable of bonding with a metal, doping one. The alkali metal or alkaline earth metal forms an energy gap state in the N-type charge generation layer, and it is determined that electrons generated by the P-type charge generation layer can be easily introduced into the electron transport layer via the energy gap state generated in the N-type charge generation layer. Therefore, the P-type charge generating layer allows electrons to be smoothly introduced and transferred to the N-type charge generating layer, and thus the driving voltage of the organic light-emitting device is lowered and the efficiency and life are improved.

< Experimental example 4> Use group 2 Compound organic light-emitting device

1) Manufacture of organic light-emitting devices

The glass transparent electrode ITO film (manufactured by Samsung-Corning Co., Ltd.) for OLED was washed with trichloroethylene, acetone, ethanol, and distilled water for 5 minutes, and then the ITO film was placed in isopropyl alcohol. Then use it.

Subsequently, an ITO substrate was placed in a substrate holder of a vacuum deposition apparatus, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) ) Put it in one of the vacuum deposition equipment.

The air in the emptying tank is followed until the vacuum in the tank reaches 10 ^-6 Torr, and then the current is passed into a small cell to volatilize 2-TNATA, thereby depositing a hole injection layer having a thickness of 600 Å on the ITO substrate.

The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) is placed in another cell of the vacuum deposition apparatus and a current is passed into the The small grid volatilizes the NPB, thereby depositing a hole transport layer having a thickness of 300 Å on the hole injection layer.

The hole injection layer and the hole transport layer are formed as above, and then a blue light-emitting material having the following structure is deposited thereon as a light-emitting layer. Specifically, the blue light-emitting host material H1 is vacuum-deposited to a thickness of 200 Å in one of the vacuum deposition apparatuses, and then the blue light-emitting dopant material D1 is vacuum-deposited thereon in an amount relative to the main body. 5% of the material.

Subsequently, a compound having the following structural formula E1 was deposited to a thickness of 300 Å as an electron transport layer.

Lithium fluoride (LiF) having a thickness of 10 Å was deposited as an electron injecting layer, and the thickness of the Al negative electrode was 1,000 Å, thereby fabricating an OLED device.

At the same time, all the organic compounds required for the fabrication of the OLED device were subjected to vacuum sublimation purification at 10 ^-6 to 10 ^-8 Torr and used to manufacture OLEDs.

2) Driving voltage and luminous efficiency of organic light-emitting device

The electroluminescence (EL) characteristics of the above-described organic light-emitting device were measured using M7000 manufactured by McScience Inc., and the lifetime measurement device (M6000) manufactured by McScience Inc. was used, and the reference luminance was evaluated to be 700 cd/m ² based on the measurement result. T ₉₅ . The measurement results of the organic light-emitting device manufactured according to the present invention in terms of driving voltage, luminous efficiency, external quantum efficiency, and chromaticity coordinates (CIE) are shown in Table 12.

[Table 12]

As is apparent from the results of Table 12, the organic light-emitting device using the electron-transporting layer material of the blue organic light-emitting device of the present invention has a lower driving voltage than that of Comparative Example 4, and can significantly improve luminous efficiency and lifetime.

The reason for this improvement is that the compound of the present invention has an appropriate length and strength and smoothing properties. When used as an electron transporting layer, it accepts electrons under specific conditions to produce a compound in an excited state, and in particular, when a compound When the hybrid skeleton site forms an excited state, the excited energy moves to a stable state, and then the excited hybrid skeleton site undergoes another reaction, and in the relatively stable compound, the compound does not decompose or destroy, And the electrons can be transmitted efficiently. For reference only, the compound having a stable state upon excitation should be an aryl or acene compound or a polycyclic compound. Therefore, the compound of the present invention can improve electron transport characteristics or stability, and exhibit excellent performance in terms of driving, efficiency, and life.

100‧‧‧Substrate
200‧‧‧ positive electrode
300‧‧‧ organic material layer
301‧‧‧ hole injection layer
302‧‧‧ hole transport layer
303‧‧‧Lighting layer
304‧‧‧ hole barrier
305‧‧‧Electronic transport layer
306‧‧‧Electronic injection layer
400‧‧‧negative electrode

1 to 4 are schematic diagrams showing a stack structure of various organic light-emitting devices according to an exemplary embodiment of the present application. Figure 5 is a plot of PL measurement of Compound 16 at a wavelength of 286 nm. Figure 6 is a graph of PL measurement of Compound 16 at a wavelength of 328 nm. Figure 7 is a plot of PL measurement of Compound 16 at a wavelength of 404 nm. Figure 8 is a graph of PL measurement of compound 209 at a wavelength of 239 nm. Figure 9 is a plot of PL of compound 209 at a wavelength of 292 nm. Figure 10 is a plot of PL of compound 209 at a wavelength of 338 nm. Figure 11 is a plot of PL of compound 209 at a wavelength of 408 nm. Figure 12 is a graph of PL measurement of Compound 44 at a wavelength of 280 nm. Figure 13 is a P measurement of Compound 44 at a wavelength of 414 nm.

100‧‧‧Substrate

200‧‧‧ positive electrode

300‧‧‧ organic material layer

400‧‧‧negative electrode

Claims (17)

A heterocyclic compound represented by the following Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, R1 is hydrogen or heavy hydrogen, or is represented by -(Li)p-(Y1)q, R2 is hydrogen, a heavy hydrogen or a naphthyl group, or -(L2)r-(Y2) As indicated by s, L1 and L2 are each independently selected from the group consisting of a monosubstituted or unsubstituted arylene group; and a substituted or unsubstituted cyclic or polycyclic heteroarylene group, Y1 and Y2 Is selected from the group consisting of: hydrogen; heavy hydrogen; a halogen group; -CN; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkyne group a monosubstituted or unsubstituted alkoxy group; a monosubstituted or unsubstituted cycloalkyl group; a monosubstituted or unsubstituted heterocycloalkyl group; a monosubstituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; ;-SiRR'R";-P(=O)RR'; and an amine which is unsubstituted or substituted with a monoalkyl group, a monosubstituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; a group, p is 0 to 10 and q is 1 to 10, r is 0 to 10 and s is 1 to 10, and R3 to R10 are the same or different from each other, and are each independently selected from the group consisting of: Hydrogen; heavy hydrogen; a group; -CN; a monosubstituted or unsubstituted alkyl group; a monosubstituted or unsubstituted alkenyl group; a monosubstituted or unsubstituted alkyne group; a substituted or unsubstituted alkoxy group; a monosubstituted or unsubstituted cycloalkane a monosubstituted or unsubstituted heterocycloalkyl group; a monosubstituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; -SiRR'R";-P(=O)RR'; An amine group which is unsubstituted or substituted with a monoalkyl group, a monosubstituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or two or more adjacent groups are bonded to each other to form a substitution Or unsubstituted monocyclic or polycyclic aliphatic or aromatic hydrocarbon ring, and R, R' and R" are the same or different from each other, and are each independently hydrogen; heavy hydrogen; -CN; monosubstituted or unsubstituted alkyl group; a monosubstituted or unsubstituted cycloalkyl group; a monosubstituted or unsubstituted aryl group; or a monosubstituted or unsubstituted heteroaryl group. The heterocyclic compound according to claim 1, wherein when R2 of Chemical Formula 1 is hydrogen or heavy hydrogen, R1 is represented by -(L1)p-(Y1)q. The heterocyclic compound according to claim 1, wherein when R1 of Chemical Formula 1 is hydrogen or heavy hydrogen, R2 is a naphthyl group or is represented by -(L2)r-(Y2)s. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any one of Formulas 2 to 7 below: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] In Chemical Formulas 2 to 7, R1 to R10 are as defined in Chemical Formula 1, and R11 are each independently selected from the group consisting of hydrogen; heavy hydrogen; a halogen group; -CN; Unsubstituted alkyl group; monosubstituted or unsubstituted alkenyl group; monosubstituted or unsubstituted alkyne group; monosubstituted or unsubstituted alkoxy group; monosubstituted or unsubstituted cycloalkyl group; monosubstituted or unsubstituted hetero a cycloalkyl group; a monosubstituted or unsubstituted aryl group; a monosubstituted or unsubstituted heteroaryl group; -SiRR'R";-P(=O)RR'; and an unsubstituted or monoalkyl group, a substituted or unsubstituted aryl group, or an amine group substituted with a substituted or unsubstituted heteroaryl group, R, R' and R" are the same or different from each other, and each is independently hydrogen; heavy hydrogen; -CN a monosubstituted or unsubstituted alkyl group; a monosubstituted or unsubstituted cycloalkyl group; a monosubstituted or unsubstituted aryl group; or a monosubstituted or unsubstituted heteroaryl group, each of which is an integer from 0 to 7 And when m is 2 or more, two or more R11 are the same or different from each other, and n is each an integer of 0 to 5, and when n is 2 or more, two or more R11 They are the same or different from each other. The heterocyclic compound according to claim 1, wherein each of L1 and L2 of Chemical Formula 1 is independently a monosubstituted or unsubstituted arylene group, and Y1 and Y2 are each independently selected from the group consisting of the following items; Group: hydrogen; heavy hydrogen; monosubstituted or unsubstituted aryl group; monosubstituted or unsubstituted heteroaryl group; and -P(=O)RR'. The heterocyclic compound according to claim 1, wherein R3 to R10 of Chemical Formula 1 are each independently hydrogen or dihydrogen. The heterocyclic compound according to claim 2, wherein R11 of the chemical formulas 2 to 7 are each independently selected from the group consisting of hydrogen; heavy hydrogen; a monosubstituted or unsubstituted aryl group; Or unsubstituted heteroaryl group; and -P(=O)RR'. The heterocyclic compound according to claim 1, wherein Y1 or Y2 is And X3 and X4 are a monosubstituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted aromatic heterocyclic ring. a heterocyclic compound as described in claim 8 of the patent application, wherein It is represented by any of the following structural formulas: In these structural formulas, Z ₁ to Z ₃ are the same or different from each other, and are each independently S or O, and Z ₄ to Z ₉ are the same or different from each other, and are each independently CR'R", NR', S, or O, and R' and R" are the same or different from each other, and are each independently hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following group 1 compounds: [Group 1] The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following group 2 compounds: [Group 2] An organic light-emitting device comprising: a positive electrode; a negative electrode; and one or more organic material layers disposed between the positive electrode and the negative electrode, wherein one or more layers of the organic material layers are included in the patent application scope The heterocyclic compound according to any one of items 1 to 11. The organic light-emitting device of claim 12, wherein the organic material layer comprises at least one of a hole barrier layer, an electron injection layer and an electron transport layer, and the hole barrier layer, the electron injection layer At least one of the layer and the electron transport layer contains the heterocyclic compound. The organic light-emitting device of claim 12, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer comprises the heterocyclic compound. The organic light-emitting device of claim 12, wherein the organic material layer comprises a hole injection layer, a hole transport layer, and one or more layers of a layer of simultaneously implanted and transported holes, and the like One of the layers contains the heterocyclic compound. The organic light-emitting device of claim 12, wherein the organic material layer comprises a charge generating layer, and the charge generating layer comprises the heterocyclic compound. The organic light-emitting device of claim 16, wherein the organic light-emitting device comprises a positive electrode, a first stacked body disposed on the positive electrode and including a first light-emitting layer, and a first stacked body disposed on the first a charge generating layer on the stack, a second stack disposed on the charge generating layer and including a second light emitting layer, and a negative electrode disposed on the second stacked body.