TW202330508A - Heterocyclic compound, organic light emitting device comprising same and composition for organic material layer of organic light emitting device - Google Patents

Abstract

The present specification relates to a heterocyclic compound represented by the following Chemical Formula 1, an organic light emitting device including the same and a composition for an organic material layer. The definition of each substituent of the compound represented by Chemical Formula 1 is described in the present specification. The compound described in the present specification can be used as a material for the organic material layer of the organic light emitting device. When the compound represented by Chemical Formula 1 is used for an organic material layer, the driving voltage of the device can be lowered, the light efficiency of the device can be improved, and the service life characteristics of the device can be improved due to the thermal stability of the compound.

Description

Heterocyclic compound, organic light-emitting device including same, and organic layer composition of organic light-emitting device

[CROSS-REFERENCE TO RELATED APPLICATIONS]

This application claims priority and benefit from Korean Patent Application No. 10-2021-0137098 filed with the Korea Intellectual Property Office on October 15, 2021, the entire contents of which are incorporated herein by reference

This specification relates to a heterocyclic compound, an organic light-emitting element including the heterocyclic compound, and an organic material layer composition.

An electroluminescence (EL) element is a self-emission type display element, and is advantageous in that it has a wide viewing angle, an excellent contrast ratio, and a fast response speed.

An organic light emitting element has a structure in which an organic thin film is provided between two electrodes. When a voltage is applied to the organic light emitting element having the structure, electrons and holes injected from the two electrodes are combined with each other in the organic thin film, and then emit light while being extinguished. The organic thin film may consist of a single layer or a plurality of layers as required.

The material used for the organic thin film may have a light emitting function as required. For example, as a material for an organic thin film, a compound that can constitute a light-emitting layer by itself, or a compound that can be used as a host or a dopant for a host-dopant-based light-emitting layer can also be used. In addition, as a material for the organic thin film, compounds that can perform functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport, or electron injection can also be used.

In order to improve the efficacy, service life, or efficiency of organic light-emitting devices, there is a continuing need to develop materials for organic thin films. [Related Technical Documents] [Patent Document] US Patent No. 4,356,429

[technical problem]

The present invention is dedicated to providing a heterocyclic compound, an organic light-emitting element including the heterocyclic compound, and an organic material layer composition. [Technical solution]

In an exemplary embodiment of the present application, a heterocyclic compound represented by the following Chemical Formula 1 is provided. [chemical formula 1]

In Chemical Formula 1, X is O or S, Ar1 and Ar2 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR';-SiRR'R''; and substituted or unsubstituted amine groups, R1 to R8 are the same or different from each other, and are each independently selected from the group consisting of: hydrogen; deuterium ; halo; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted Substituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR';-SiRR'R''; and substituted or unsubstituted amino, and at least one of R1 to R6 One is substituted or unsubstituted C6 to C60 aryl, a is an integer of 0 to 2, b and c are integers of 0 to 4, when a is an integer of 2 or b and c are 2 or an integer higher than 2, the substituents in the brackets are the same or different from each other, m is an integer of 0 or 1, when m is an integer of 1, R5 and R6 are hydrogen or deuterium, when m is 0 When an integer, at least one of Ar1 and Ar2 is represented by the following chemical formula 1-1, [chemical formula 1-1] In Chemical Formula 1-1, X1 is O or S, R11 to R15 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted Substituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl -P(=O)RR';-SiRR'R''; and a substituted or unsubstituted amino group, and at least one of R11 to R15 is a substituted or unsubstituted C6 to C60 aromatic R, R' and R'' are the same or different from each other, and are independently substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or Unsubstituted C2 to C60 heteroaryl, and a1 is an integer of 0 to 3, and when a1 is an integer of 2 or higher, the substituents in parentheses are the same or different from each other.

In addition, in an exemplary embodiment of the present application, there is provided an organic light emitting element including: a first electrode; a second electrode disposed to face the first electrode; and having one or more layers The organic material layer is disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer includes the heterocyclic compound represented by Chemical Formula 1.

In addition, an exemplary embodiment of the present application provides an organic light emitting device in which the organic material layer including the heterocyclic compound of Chemical Formula 1 further includes a heterocyclic compound represented by Chemical Formula 2 below. [chemical formula 2]

In Chemical Formula 2, R1 to R14 are the same or different from each other, and each independently is hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; Substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 Heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; SiRaRa'Ra''; or -P(=O)RaRa', La1 and La2 are the same or different from each other, and each is independently a direct bond; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl, Ara1 and Ara2 are the same or different from each other, and are each independently -CN; SiRaRa'Ra''; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl, and Ra, Ra' and Ra'' are the same or different from each other, and are independently substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted Substituted C2 to C60 heteroaryl.

In addition, another exemplary embodiment of the present application provides an organic light emitting device organic material layer composition, which includes a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2. [Beneficial effect]

The compounds described in this specification can be used as a material for an organic material layer of an organic light-emitting element. The compound can be used as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like in an organic light emitting element. Specifically, the compound can be used as a material of a light-emitting layer of an organic light-emitting element.

Specifically, the compound can also be used alone as a light-emitting material, and can also be used as a host material or a dopant material of a light-emitting layer. When the compound represented by Chemical Formula 1 is used for the organic material layer, the driving voltage of the element can be reduced, the light efficiency of the element can be improved, and the lifetime characteristics of the element can be improved due to the thermal stability of the compound.

Specifically, both the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 may be used as a material of a light emitting layer of an organic light emitting element. In this case, the driving voltage of the device can be reduced, the light efficiency can be improved, and the lifetime characteristics of the device can be improved especially by the thermal stability of the compound.

Hereinafter, the present application will be explained in detail.

In the present invention, "when no substituent is specified in the chemical formula or the structure of the compound" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium ( ² H) and tritium ( ³ H) are isotopes of hydrogen, some hydrogen atoms may be either deuterium or tritium.

In an exemplary embodiment of the present invention, "when no substituent is indicated in the chemical formula or the structure of the compound" may mean that all positions accessible to the substituent are hydrogen, deuterium or tritium. That is, deuterium and tritium are isotopes of hydrogen, some hydrogen atoms may be deuterium and tritium as their isotopes, and in this case, the content of deuterium or tritium may be 0% to 100%.

In an exemplary embodiment of the present invention, in "the case where the substituent is not specified in the chemical formula or the structure of the compound", when the substituent does not explicitly exclude deuterium and tritium (such as "the content of deuterium is 0%", "the content of tritium When the content is 0%", "the content of hydrogen is 100%" and "the substituents are all hydrogen"), hydrogen, deuterium and tritium can be mixed and used in the compound.

In an exemplary embodiment of the present invention, deuterium is one of the isotopes of hydrogen, is an element having a deuteron composed of one proton and one neutron as a nucleus, and can be represented by hydrogen-2, and the element symbol can also be Expressed as D or ² H. Similarly, the element symbol of tritium can also be expressed as T or ³ H.

In an exemplary embodiment of the present invention, isotopes mean atoms having the same atomic number (Z) but different mass numbers (A), and isotopes can be interpreted as elements having the same number of protons but different numbers of neutrons.

In an exemplary embodiment of the present invention, when the total number of substituents of the base compound is defined as T1, and the number of specific substituents among the substituents is defined as T2, the content T of the specific substituents % can be defined as T2/T1×100 = T%.

That is, in the example, by The indicated deuterium content of 20% in the phenyl group may mean that the total number of substituents that the phenyl group may have is 5 (T1 in the formula) and the number of deuterium in the substituents is 1 (T2 in the formula) situation. That is, the deuterium content of 20% in the phenyl group can be represented by the following structural formula.

Also, in the exemplary embodiment of the present application, "a phenyl group having a deuterium content of 0%" may mean a phenyl group not including a deuterium atom (ie, having five hydrogen atoms).

In this specification, the term "substitution" 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 one where the hydrogen atom is substituted The position (that is, the position where the substituent can be substituted) is sufficient, and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

In this specification, "substituted or unsubstituted" means unsubstituted or selected from deuterium, halo, cyano, C1 to C60 straight or branched chain alkyl, C2 to C60 straight or branched alkenes C2 to C60 straight chain or branched alkynyl, C3 to C60 monocyclic or polycyclic cycloalkyl, C2 to C60 monocyclic or polycyclic heterocycloalkyl, C6 to C60 monocyclic or polycyclic aryl, C2 to C60 monocyclic or polycyclic heteroaryl, -SiRR'R'', -P(=O)RR', C1 to C20 alkylamines, C6 to C60 monocyclic or polycyclic arylamines, and C2 to C60 One or more substituents of the group consisting of monocyclic or polycyclic heteroarylamines are substituted, or unsubstituted or substituted by two or more substituents selected from the exemplified substituents linked to base substitution.

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

In the present specification, the alkyl group includes straight or branched chains having 1 to 60 carbon atoms, and may be additionally substituted with another substituent. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, second-butyl, 1-methylbutyl , 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, third pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl Base-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl , n-octyl, third octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propane radical, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but not limited thereto.

In the present specification, the alkenyl group includes straight or branched chains having 2 to 60 carbon atoms, and may be additionally substituted with another substituent. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples of alkenyl include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-butenyl, Pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylethenyl-1-yl, 2-phenylethenyl-1-yl, 2,2-Diphenylethenyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)ethenyl-1-yl, 2,2-bis(diphenyl-1-yl) Vinyl-1-yl, distyryl, styryl and the like, but not limited thereto.

In the present specification, the alkynyl group includes straight or branched chains having 2 to 60 carbon atoms, and may be additionally substituted with another substituent. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

In this specification, the alkoxy group may be a straight chain, branched or cyclic alkoxy group. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1-20. Specific examples of the alkoxy group include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, Tributoxy, second butoxy, n-pentoxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n- Octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like, but not limited thereto.

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be additionally 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 also be another cyclic group such as a heterocycloalkyl group, an aryl group, a heteroaryl group, and the like. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4- Methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and similar groups, but not limited to this.

In the present specification, the heterocycloalkyl group contains O, S, Se, N or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be additionally substituted with another substituent. 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 also be another cyclic group such as cycloalkyl, aryl, heteroaryl and the like. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and 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 additionally substituted with another substituent. Here, polycyclic means a group in which an aryl group is directly linked or fused to another cyclic group. Here, the other cyclic group may also be an aryl group, but may also be another cyclic group such as cycloalkyl, heterocycloalkyl, heteroaryl and the like. Aryl includes spirocyclyl. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of aryl groups include phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, phenanthryl, phenanthrenyl, perylene, fluoranthenyl, biterphenylenyl, phenanthyl, pyrenyl, pyrene, Phenyl, fused pentaphenyl, fluorenyl, indenyl, acenaphthyl, benzofluorenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, fused rings thereof and similar groups, but Not limited to this.

In this specification, the phosphine oxide group is represented by -P(=O)R101R102, and R101 and R102 are the same or different from each other, and may each independently be a substituent composed of at least one of the following: hydrogen; deuterium; halogen alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and heterocyclyl. Specifically, the phosphine oxide group may be substituted with an aryl group, and the above examples may apply to aryl groups. Examples of the phosphine oxide group include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide group, and the like.

In the present specification, the silyl group contains Si and is a substituent to which the Si atom is directly bonded as a radical, and is represented by -SiR104R105R106, and R104 to R106 are the same or different from each other, and may each independently be represented by at least Substituents consisting of: hydrogen; deuterium; halo; alkyl; alkenyl; alkoxy; cycloalkyl; aryl; Specific examples of silyl groups include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, Diphenylsilyl, phenylsilyl and the like, but not limited thereto.

In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

When the fluorenyl group is substituted, the substituent may be the following structure, but is not limited thereto.

In the present specification, the heteroaryl group contains S, O, Se, N or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be additionally substituted with another substituent. 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 also be another cyclic group such as cycloalkyl, heterocycloalkyl, aryl and the like. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of heteroaryl include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, tri Azolyl, furanyl, oxadiazolyl, thiadiazolyl, bithiazolyl, tetrazolyl, pyranyl, thiopyryl, diazinyl, oxazinyl, thiazinyl, dioxinyl (dioxynyl) group), triazinyl, tetrazinyl, quinolinyl, isoquinolyl, quinazolinyl (quinazolinyl group), isoquinazolinyl, quinazolilyl group (qninozolilyl group), naphthyridinyl, acridine Base, phenanthridinyl group (phenanthridinyl group), imidazopyridyl, naphthyl, triazindenyl, indolyl, indolyl, benzothiazolyl, benzoxazolyl, benzimidazole benzothienyl, benzofuryl, dibenzothienyl, dibenzofuryl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenazinyl, dibenzosilyl Cyclopentadienyl (dibenzosilole group), spirobis(dibenzosilole), dihydrophenanthrazinyl, phenanthoxazinyl, phenanthridyl group, imidazopyridyl, thiophene Indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, indolinyl, 10,11-dihydro-dibenzo[b,f ]Azinyl, 9,10-dihydroacridinyl, phenazinyl, phenothiathiazinyl group, phthalazinyl, naphthiazinyl, phenanthrinyl, benzo[c][1,2 ,5]thiadiazolyl, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl, pyrido [1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]indolinyl, 5,11-dihydroindeno[1,2-b] Carbazolyl and the like, but not limited thereto.

In this specification, the amine group can be selected from monoalkylamine group, monoarylamine group, monoheteroarylamine group, _-NH2 , dialkylamine group, diarylamine group, diheteroarylamine group A group consisting of an alkylarylamine group, an alkylarylamine group, an alkylheteroarylamine group and an arylheteroarylamine group, and the number of carbon atoms in the amine group is not particularly limited, but is preferably 1-30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a biphenylamine group, , anthracenylamino, 9-methyl-anthracenylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenylcresylamino, triphenylamino, biphenyl phenylnaphthylamine, phenylbiphenylylamine, biphenylfluorenylamine, phenylbisphenylylamine, biphenylbiphenylylamine and similar groups, but not limited to this.

In this specification, the aryl group means a group having two bonding positions in the aryl group, that is, a divalent group. The above description for the aryl group is applicable to the aryl group except that the aryl group is each a divalent group. Furthermore, a heteroaryl means that there are two bonding positions in the heteroaryl, ie a divalent group. In addition to divalent heteroaryl groups, the above description for heteroaryl groups can be applied to heteroaryl groups.

In this specification, an "adjacent" group may mean a substituent substituted by an atom directly bonded to the atom in which the corresponding substituent is substituted, a substituent spatially closest to the corresponding substituent, or a substituent in which the corresponding substituent is substituted. Substituent A substituting atom is substituted by another substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted with the same carbon in an aliphatic ring may be construed as being "adjacent" to each other.

In an exemplary embodiment of the present application, a compound represented by Chemical Formula 1 is provided.

In an exemplary embodiment of the present application, a group not represented by a substituent or a group represented by hydrogen may mean that both may be substituted with deuterium. That is, in the exemplary embodiments of the present application, it may be shown that hydrogen or deuterium may be substituted for each other.

In the exemplary embodiment of the present application, the fact that m is 0 means direct bonding.

Specifically, in Chemical Formula 1, the case where m is 0 may mean the following structural formula, and since m is 0, the definition of each substituent may be interpreted identically except being directly bonded.

In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of Chemical Formula 3 to Chemical Formula 5 below. [chemical formula 3] [chemical formula 4] [chemical formula 5]

In Chemical Formula 3 to Chemical Formula 5, The definition of each substituent is the same as that in Chemical Formula 1.

In an exemplary embodiment of the present application, Chemical Formula 3 may be represented by any one of the following Chemical Formula 3-1 to Chemical Formula 3-3. [chemical formula 3-1] [chemical formula 3-2] [chemical formula 3-3]

In Chemical Formula 3-1 to Chemical Formula 3-3, The definition of each substituent is the same as that in Chemical Formula 3.

In an exemplary embodiment of the present application, Chemical Formula 4 may be represented by any one of the following Chemical Formula 4-1 to Chemical Formula 4-3. [chemical formula 4-1] [chemical formula 4-2] [chemical formula 4-3]

In Chemical Formula 4-1 to Chemical Formula 4-3, The definition of each substituent is the same as that in Chemical Formula 4.

In an exemplary embodiment of the present application, Chemical Formula 5 may be represented by any one of the following Chemical Formula 5-1 to Chemical Formula 5-3. [chemical formula 5-1] [chemical formula 5-2] [chemical formula 5-3]

In Chemical Formula 5-1 to Chemical Formula 5-3, The definition of each substituent is the same as that in Chemical Formula 5.

In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of Chemical Formula 6 to Chemical Formula 8 below. [chemical formula 6] [chemical formula 7] [chemical formula 8]

In Chemical Formula 6 to Chemical Formula 8, The definition of each substituent is the same as that in Chemical Formula 1.

In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of Chemical Formula 9 to Chemical Formula 11 below. [chemical formula 9] [chemical formula 10] [chemical formula 11]

In Chemical Formula 9 to Chemical Formula 11, R1 to R8, R11 to R15, a, b, c, a1, X, and X1 are as defined in Chemical Formula 1, and Ar11 and Ar12 are the same or different from each other, and each is independently a substituted or unsubstituted C6-C60 aryl group.

In an exemplary embodiment of the present application, Ar11 and Ar12 are the same or different from each other, and each is independently a substituted or unsubstituted C6-C60 aryl group.

In another exemplary embodiment, Ar11 and Ar12 are the same or different from each other, and each is independently a substituted or unsubstituted C6-C40 aryl group.

In yet another exemplary embodiment, Ar11 and Ar12 are the same or different from each other, and each is independently a substituted or unsubstituted C6-C20 aryl group.

In yet another exemplary embodiment, Ar11 and Ar12 are the same or different from each other, and each is independently a substituted or unsubstituted C6-C12 aryl group.

In yet another exemplary embodiment, Ar11 and Ar12 are the same or different from each other, and each is independently an unsubstituted or deuterium-substituted C6-C12 aryl group.

In yet another exemplary embodiment, Ar11 and Ar12 are the same or different from each other, and each is independently an unsubstituted or deuterium-substituted phenyl group; or an unsubstituted or deuterium-substituted biphenyl group.

In an exemplary embodiment of the present application, Chemical Formula 1-1 may be represented by any one of the following Chemical Formula 1-1-1 to Chemical Formula 1-1-4. [chemical formula 1-1-1] [Chemical formula 1-1-2] [chemical formula 1-1-3] [chemical formula 1-1-4]

In Chemical Formula 1-1-1 to Chemical Formula 1-1-4, The definition of each substituent is the same as in Chemical Formula 1-1.

In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by the following Structural Formulas A to D, and the deuterium content of the following Structural Formulas A to D is 0% to 100%. [Structural formula A] [Structural formula B] [Structural formula C] [Structural formula D]

In structural formula A to structural formula D, the bonding position means a position to which each substituent is bonded, and the same symbols are bonded to each other, and the definition of each substituent is the same as that in Chemical Formula 1.

In an exemplary embodiment of the present application, the deuterium content of the structural formula A may be 0% to 100%.

In another exemplary embodiment, the deuterium content of structural formula A may be 0% to 100%; 10% to 100%; 20% to 100%; 30% to 100%; 50% to 100%; or 80% to 100%.

In yet another exemplary embodiment, the deuterium content of Formula A may be 0% or 100%.

In an exemplary embodiment of the present application, the deuterium content of the structural formula B may be 0% to 100%.

In another exemplary embodiment, the deuterium content of formula B may be 0% to 100%; 10% to 100%; 20% to 100%; 30% to 100%; 50% to 100%; or 80% to 100%.

In yet another exemplary embodiment, the deuterium content of Formula B may be 0% or 100%.

In an exemplary embodiment of the present application, the deuterium content of the structural formula C may be 0% to 100%.

In another exemplary embodiment, the deuterium content of structural formula C may be 0% to 100%; 10% to 100%; 20% to 100%; 30% to 100%; 50% to 100%; or 80% to 100%.

In yet another exemplary embodiment, the deuterium content of Formula C may be 0% or 100%.

In an exemplary embodiment of the present application, the deuterium content of the structural formula D may range from 0% to 100%.

In another exemplary embodiment, the deuterium content of structural formula D may be 0% to 100%; 10% to 100%; 20% to 100%; 30% to 100%; 50% to 100%; or 80% to 100%.

In yet another exemplary embodiment, the deuterium content of Formula D may be 0% or 100%.

In an exemplary embodiment of the present application, the deuterium content of the structural formulas A to D may be 0% or 100%.

In an exemplary embodiment of the present application, R1 to R8 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halo; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; -SiRR'R''; and substituted or unsubstituted amine, and at least one of R1 to R6 may be substituted or unsubstituted C6 to C60 aryl .

In another exemplary embodiment, R1 to R8 are the same or different from each other, and are independently hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aromatic or a substituted or unsubstituted C2 to C60 heteroaryl group, and at least one of R1 to R6 may be a substituted or unsubstituted C6 to C60 aryl group.

In yet another exemplary embodiment, R1 to R8 are the same or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted C1 to C40 alkyl; substituted or unsubstituted C6 to C40 aromatic or a substituted or unsubstituted C2 to C40 heteroaryl group, and at least one of R1 to R6 may be a substituted or unsubstituted C6 to C40 aryl group.

In yet another exemplary embodiment, R1 to R8 are the same or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aromatic or a substituted or unsubstituted C2 to C20 heteroaryl group, and at least one of R1 to R6 may be a substituted or unsubstituted C6 to C20 aryl group.

In yet another exemplary embodiment, R1 to R8 are the same or different from each other, and each independently is hydrogen; deuterium; unsubstituted or deuterium-substituted C1 to C20 alkyl; unsubstituted or deuterium-substituted C6 to C20 aryl; or unsubstituted or deuterium substituted C2 to C20 heteroaryl, and at least one of R1 to R6 may be unsubstituted or deuterium substituted C6 to C20 aryl.

In yet another exemplary embodiment, R1 to R8 are the same or different from each other, and each independently is hydrogen; deuterium; or unsubstituted or deuterium-substituted phenyl, and at least one of R1 to R6 may be unsubstituted Substituted or deuterium-substituted phenyl.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same or different from each other, and can each be independently selected from the group consisting of hydrogen; deuterium; halo; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted Substituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl ; -P(=O)RR'; -SiRR'R''; and substituted or unsubstituted amine groups,

In another exemplary embodiment, Ar1 and Ar2 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl.

In yet another exemplary embodiment, Ar1 and Ar2 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C1 to C40 alkyl; substituted or unsubstituted C6 to C40 aryl; or a substituted or unsubstituted C2 to C40 heteroaryl.

In yet another exemplary embodiment, Ar1 and Ar2 are the same or different from each other, and may each independently be hydrogen; deuterium; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl; or a substituted or unsubstituted C2 to C20 heteroaryl.

In yet another exemplary embodiment, Ar1 and Ar2 are the same or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or Substituted or unsubstituted C2 to C20 heteroaryl.

In yet another exemplary embodiment, Ar1 and A2 are the same or different from each other, and each independently can be an unsubstituted or deuterium-substituted C1-C20 alkyl group; an unsubstituted or deuterium-substituted C6-C20 aryl group ; or unsubstituted or deuterium-substituted C2 to C20 heteroaryl.

In yet another exemplary embodiment, Ar1 and Ar2 are the same or different from each other, and each independently can be an unsubstituted or deuterium-substituted C1-C20 alkyl group; an unsubstituted or deuterium-substituted C6-C20 aryl group or a C2 to C20 heteroaryl that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C6 to C20 aryl.

In yet another embodiment, Ar1 and Ar2 are the same or different from each other, and each independently can be unsubstituted or deuterium-substituted phenyl; unsubstituted or deuterium-substituted biphenyl; unsubstituted or deuterium-substituted biphenyl; Substituted dibenzofuryl; unsubstituted or deuterium-substituted dibenzothienyl.

In an exemplary embodiment of the present application, when m is an integer of 1, R5 and R6 may be hydrogen or deuterium. That is, in Chemical Formula 1, when m is an integer of 1, at least one of R1 to R4 has a substituted or unsubstituted C6 to C60 aryl group, and R5 and R6 may have hydrogen or deuterium.

In an exemplary embodiment of the present application, when m is an integer of 0, at least one of Ar1 and Ar2 may be represented by the following Chemical Formula 1-1. [chemical formula 1-1]

In Chemical Formula 1-1, X1 is O or S, R11 to R15 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halo; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; Unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; -SiRR 'R''; and a substituted or unsubstituted amino group, and at least one of R11 to R15 is a substituted or unsubstituted C6 to C60 aryl group.

In an exemplary embodiment of the present application, R11 to R15 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halo; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; -SiRR'R''; and a substituted or unsubstituted amino group, and at least one of R11 to R15 is a substituted or unsubstituted C6 to C60 aryl group.

In another exemplary embodiment, R11 to R15 are the same or different from each other, and are independently hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aromatic or a substituted or unsubstituted C2 to C60 heteroaryl group, and at least one of R11 to R15 is a substituted or unsubstituted C6 to C60 aryl group.

In yet another exemplary embodiment, R11 to R15 are the same or different from each other, and are each independently hydrogen; deuterium; unsubstituted or deuterium-substituted C1 to C60 alkyl; unsubstituted or deuterium-substituted C6 to C60 aryl; or unsubstituted or deuterium-substituted C2 to C60 heteroaryl, and at least one of R11 to R15 is unsubstituted or deuterium-substituted C6 to C60 aryl.

In yet another exemplary embodiment, R11 to R15 are the same or different from each other, and each independently is hydrogen; deuterium; unsubstituted or deuterium-substituted C1 to C40 alkyl; unsubstituted or deuterium-substituted C6 to C40 alkyl; C40 aryl; or unsubstituted or deuterium-substituted C2 to C40 heteroaryl, and at least one of R11 to R15 is unsubstituted or deuterium-substituted C6 to C40 aryl.

In yet another exemplary embodiment, R11 to R15 are the same or different from each other, and each independently is hydrogen; deuterium; unsubstituted or deuterium-substituted C1 to C20 alkyl; unsubstituted or deuterium-substituted C6 to C20 alkyl; C20 aryl; or unsubstituted or deuterium-substituted C2 to C20 heteroaryl, and at least one of R11 to R15 is unsubstituted or deuterium-substituted C6 to C20 aryl.

In yet another exemplary embodiment, R11 to R15 are the same or different from each other, and each independently is hydrogen; deuterium; or an unsubstituted or deuterium-substituted C6 to C20 aryl group, and at least one of R11 to R15 is an unsubstituted or deuterium-substituted C6 to C20 aryl.

In yet another exemplary embodiment, R11 to R15 are the same or different from each other, and each independently is hydrogen; deuterium; or unsubstituted or deuterium-substituted phenyl, and at least one of R11 to R15 is unsubstituted Substituted or deuterium-substituted phenyl.

In an exemplary embodiment of the present application, R, R' and R'' are the same or different from each other, and each independently may be a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or substituted or unsubstituted heteroaryl.

In another exemplary embodiment, R, R′ and R″ are the same or different from each other, and each independently may be a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

In yet another exemplary embodiment, R, R' and R'' are the same or different from each other, and may each be independently substituted or unsubstituted C1 to C60 alkyl; or substituted or unsubstituted C6 to C60 aryl.

In yet another exemplary embodiment, R, R′ and R″ are the same or different from each other, and may each be independently a C1 to C60 alkyl group; or a C6 to C60 aryl group.

In yet another exemplary embodiment, R, R′ and R″ are the same or different from each other, and may each independently be a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

In yet another exemplary embodiment, R, R' and R'' may be substituted or unsubstituted phenyl groups.

In yet another exemplary embodiment, R, R' and R'' may be phenyl.

In an exemplary embodiment of the present application, there is provided a heterocyclic compound in which Chemical Formula 1 is represented by any one of the following compounds.

In addition, various substituents may be introduced into the structure of Chemical Formula 1 to synthesize compounds having inherent properties of the introduced substituents. For example, by using substituents commonly used in hole injection layer materials, materials for transporting holes, light-emitting layer materials, electron transport layer materials, and charge generation layer materials (all of which are used in the preparation of organic light-emitting elements) Introduced into the core structure, materials satisfying the conditions required for each organic material layer can be synthesized.

In addition, by introducing various substituents into the structure of Chemical Formula 1, the energy band-gap can be finely adjusted, and at the same time, the characteristics at the interface between organic materials can be improved, and the material can be The uses are diverse.

Meanwhile, the compound has a high glass transition temperature (Tg), and thus has excellent thermal stability. The increase in thermal stability becomes an important factor in providing drive stability to the element.

In addition, in an exemplary embodiment of the present application, there is provided an organic light emitting element including: a first electrode; a second electrode disposed to face the first electrode; and having one or more layers The organic material layer is disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer includes the heterocyclic compound represented by Chemical Formula 1.

In an exemplary embodiment of the present application, the first electrode may be a positive electrode, and the second electrode may be a negative electrode.

In another exemplary embodiment, the first electrode may be a negative electrode, and the second electrode may be a positive electrode.

In an exemplary embodiment of the present application, the organic light emitting element may be a blue organic light emitting element, and the heterocycle according to Chemical Formula 1 may be used as a material for the blue organic light emitting element.

In an exemplary embodiment of the present application, the organic light emitting element may be a green organic light emitting element, and the compound represented by Chemical Formula 1 may be used as a material for the green organic light emitting element.

In an exemplary embodiment of the present application, the organic light emitting element may be a red organic light emitting element, and the compound represented by Chemical Formula 1 may be used as a material for the red organic light emitting element.

In an exemplary embodiment of the present application, the organic light emitting element may be a blue organic light emitting element, and the heterocycle according to Chemical Formula 1 may be used as a material for a light emitting layer of the blue organic light emitting element.

In an exemplary embodiment of the present application, the organic light emitting element may be a green organic light emitting element, and the compound represented by Chemical Formula 1 may be used as a material for a light emitting layer of the green organic light emitting element.

In an exemplary embodiment of the present application, the organic light emitting element may be a red organic light emitting element, and the compound represented by Chemical Formula 1 may be used as a material for a light emitting layer of the red organic light emitting element.

The specific content of the heterocyclic compound represented by Chemical Formula 1 is the same as the above-mentioned content.

The organic light-emitting device of the present invention can be manufactured using typical manufacturing methods and materials of an organic light-emitting device, except that the above-mentioned heterocyclic compound is used to form an organic material layer having one or more layers.

When manufacturing an organic light emitting element, the heterocyclic compound can be formed as an organic material layer not only by a vacuum deposition method but also by a solution application method. Here, the solution application method means spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating (roll coating) and similar methods, but not limited thereto.

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

In an organic light emitting element according to an exemplary embodiment of the present application, there is provided an organic light emitting element in which an organic material layer including a heterocyclic compound represented by Chemical Formula 1 further includes a heterocyclic compound represented by Chemical Formula 2 below. [chemical formula 2]

In Chemical Formula 2, R1 to R14 are the same or different from each other, and each independently is hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; Substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 Heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; SiRR'R''; or -P(=O)RR', La1 and La2 are the same or different from each other, and each is independently a direct bond; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl, Ara1 and Ara2 are the same or different from each other, and are each independently -CN; SiRaRa'Ra''; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl, and Ra, Ra' and Ra'' are the same or different from each other, and are independently substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted Substituted C2 to C60 heteroaryl.

In an exemplary embodiment of the present application, Chemical Formula 2 may be represented by a bond of the following Structural Formula A-1 to the following Structural Formula C-1. [Structural formula A-1] [Structural formula B-1] [Structural formula C-1]

In structural formula A-1 to structural formula C-1, the bonding position means the position to which each substituent is bonded, and the same symbols are bonded to each other, the definition of each substituent is the same as the definition in Chemical Formula 2, and the deuterium content of Structural Formula A-1 to Structural Formula C-1 from 0% to 100%.

The deuterium content of Structural Formula A-1 to Structural Formula C-1 may refer to the total deuterium content in the structures represented by Structural Formula A-1 to Structural Formula C-1.

In an exemplary embodiment of the present application, the deuterium content of the structural formula A-1 may be 0% to 100%.

In another exemplary embodiment, the deuterium content of the structural formula A-1 may be 0% to 100%, 20% to 100%, 30% to 100%, 40% to 100%, 50% to 100%, 60% % to 100% and 70% to 100%, and can be 0% or 100%.

In an exemplary embodiment of the present application, the deuterium content of the structural formula B-1 may be 0% to 100%.

In another exemplary embodiment, the deuterium content of the structural formula B-1 can be 0% to 100%, 20% to 100%, 30% to 100%, 40% to 100%, 50% to 100%, 60% % to 100% and 70% to 100%, and can be 0% or 100%.

In an exemplary embodiment of the present application, the deuterium content of the structural formula C-1 may be 0% to 100%.

In another exemplary embodiment, the deuterium content of structural formula C-1 may be 0% to 100%, 20% to 100%, 30% to 100%, 40% to 100%, 50% to 100%, 60% % to 100% and 70% to 100%, and can be 0% or 100%.

In an exemplary embodiment of the present application, the deuterium content of the structural formula A-1, structural formula B-1, structural formula C-1, or structural formula A-1 to structural formula C-1 may be 100%.

In an exemplary embodiment of the present application, the deuterium content of the structural formula A-1 and the structural formula B-1 is 50% to 100%, and the deuterium content of the structural formula C-1 may be 0%.

In another exemplary embodiment, the deuterium content of the structural formula A-1 and the structural formula B-1 is 60% to 100%, and the deuterium content of the structural formula C-1 may be 0%.

In yet another exemplary embodiment, the deuterium content of the structural formula A-1 and the structural formula B-1 is 70% to 100%, and the deuterium content of the structural formula C-1 may be 0%.

In yet another exemplary embodiment, the deuterium content of the structural formula A-1 and the structural formula B-1 is 80% to 100%, and the deuterium content of the structural formula C-1 may be 0%.

In yet another exemplary embodiment, the deuterium content of the structural formula A-1 and the structural formula B-1 is 100%, and the deuterium content of the structural formula C-1 may be 0%.

In an exemplary embodiment of the present application, the deuterium content of the structural formula C-1 is 50% to 100%, and the deuterium content of the structural formula A-1 and the structural formula B-1 may be 0%.

In another exemplary embodiment, the deuterium content of the structural formula C-1 is 60% to 100%, and the deuterium content of the structural formula A-1 and the structural formula B-1 may be 0%.

In yet another exemplary embodiment, the deuterium content of the structural formula C-1 is 70% to 100%, and the deuterium content of the structural formula A-1 and the structural formula B-1 may be 0%.

In yet another exemplary embodiment, the deuterium content of the structural formula C-1 is 80% to 100%, and the deuterium content of the structural formula A-1 and the structural formula B-1 may be 0%.

In yet another exemplary embodiment, the deuterium content of the structural formula C-1 is 100%, and the deuterium content of the structural formula A-1 and the structural formula B-1 may be 0%.

In an exemplary embodiment of the present application, the deuterium content of the structural formulas A-1 to C-1 may be 50% to 100%.

In another exemplary embodiment, the deuterium content of the structural formulas A-1 to C-1 may be 60% to 100%.

In yet another exemplary embodiment, the deuterium content of the structural formulas A-1 to C-1 may be 70% to 100%.

In yet another exemplary embodiment, the deuterium content of the structural formulas A-1 to C-1 may be 100%.

In an exemplary embodiment of the present application, R1 to R14 are the same or different from each other, and each independently is hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl; substituted or Unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl ; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; SiRR'R''; -P(=O)RR'.

In another exemplary embodiment, R1 to R14 are the same or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aromatic or substituted or unsubstituted C2 to C60 heteroaryl.

In yet another exemplary embodiment, R1 to R14 are the same or different from each other, and are each independently hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C40 aromatic or substituted or unsubstituted C2 to C40 heteroaryl.

In yet another exemplary embodiment, Ra1 to Ra14 are the same or different from each other, and are each independently hydrogen or deuterium.

In an exemplary embodiment of the present application, La1 and La2 are the same or different from each other, and each is independently a direct bond; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 To C60 extended heteroaryl.

In another exemplary embodiment, La1 and La2 are the same or different from each other, and each is independently a direct bond; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 Heteroaryl.

In yet another exemplary embodiment, La1 and La2 are the same or different from each other, and each is independently a direct bond; or a substituted or unsubstituted C6 to C40 aryl group.

In yet another exemplary embodiment, La1 and La2 are the same or different from each other, and each is independently a direct bond; or a substituted or unsubstituted C6 to C20 aryl group.

In yet another exemplary embodiment, La1 and La2 are the same or different from each other, and each is independently a direct bond; or an unsubstituted or deuterium-substituted C6-C20 arylylene group.

In yet another exemplary embodiment, La1 and La2 are the same or different from each other, and are each independently a direct bond; an unsubstituted or deuterium-substituted phenylene group; or an unsubstituted or deuterium-substituted biphenylene group .

In an exemplary embodiment of the present application, Ara1 and Ara2 are the same or different from each other, and are each independently -CN; SiRaRa'Ra''; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted a substituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl.

In another exemplary embodiment, Ara1 and Ara2 are the same or different from each other, and are each independently -CN; SiRaRa'Ra''; substituted or unsubstituted C1 to C40 alkyl; substituted or unsubstituted C6 to C40 aryl; or substituted or unsubstituted C2 to C40 heteroaryl.

In yet another exemplary embodiment, Ara1 and Ara2 are the same or different from each other, and are each independently -CN; SiRaRa'Ra''; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

In yet another exemplary embodiment, Ara1 and Ara2 are the same or different from each other, and are each independently -CN; SiRaRa'Ra''; unsubstituted or deuterium-substituted C1 to C20 alkyl; unsubstituted or deuterium-substituted C6 to C20 aryl; or unsubstituted or deuterium-substituted C2 to C20 heteroaryl.

In yet another exemplary embodiment, Ara1 and Ara2 are the same or different from each other, and are each independently -CN; SiRaRa'Ra''; unsubstituted or deuterium-substituted phenyl; unsubstituted or deuterium-substituted Biphenyl; unsubstituted or deuterium-substituted naphthyl; unsubstituted or deuterium-substituted biterphenyl; unsubstituted or deuterium-substituted terphenyl; unsubstituted or deuterium-substituted bis methylfluorenyl; unsubstituted or deuterium-substituted diphenylfluorenyl; or unsubstituted or deuterium-substituted spirobifluorenyl.

In an exemplary embodiment of the present application, Ra, Ra' and Ra'' are the same or different from each other, and are each independently substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

In another exemplary embodiment, Ra, Ra' and Ra'' are the same or different from each other, and each is independently a substituted or unsubstituted C6-C60 aryl group.

In yet another exemplary embodiment, Ra, Ra' and Ra'' are the same or different from each other, and each is independently a substituted or unsubstituted C6-C40 aryl group.

In yet another exemplary embodiment, Ra, Ra' and Ra'' are the same or different from each other, and each is independently a substituted or unsubstituted C6-C20 aryl group.

In yet another exemplary embodiment, Ra, Ra' and Ra'' are the same or different from each other, and are each independently an unsubstituted or deuterium-substituted C6-C20 aryl group.

In yet another exemplary embodiment, Ra, Ra' and Ra'' are the same or different from each other, and are each independently unsubstituted or deuterium-substituted phenyl.

When the compound of Chemical Formula 1 and the compound of Chemical Formula 2 are contained in the organic material layer of the organic light-emitting device, better efficiency and service life effects are exhibited. From this result it can be expected that an exciplex phenomenon will occur when both compounds are included.

The excited complex phenomenon is the release of the energy level of the highest occupied molecular orbital (HOMO) with a donor (p-body) and an acceptor (n-body) due to the electron exchange between two molecules. The phenomenon of the energy of the magnitude of the lowest unoccupied molecular orbital (LUMO) energy level. When excitation complexes occur between two molecules, reverse intersystem crossing (RISC) occurs, and due to RISC, the internal quantum efficiency of fluorescence can be increased to 100%. When a donor (p-host) with good hole-transport ability and an acceptor (n-host) with good electron-transport ability are used as hosts for the light-emitting layer, holes are injected into the p-host, and electrons Injected into the n-body so that the driving voltage can be reduced, which can help to improve lifetime.

In an exemplary embodiment of the present application, the heterocyclic compound represented by Chemical Formula 2 may be any one selected from the following compounds.

In addition, another exemplary embodiment of the present application provides an organic light emitting device organic material layer composition, which includes a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2.

Specific contents of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 are the same as those described above.

The weight ratio of the heterocyclic compound represented by Chemical Formula 1: the heterocyclic compound represented by Chemical Formula 2 in the composition may be 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1 and 1:2 to 2:1, but not limited to.

The composition may be used when forming an organic material for an organic light emitting element, and in particular, may be more preferably used when forming a host of a light emitting layer.

In an exemplary embodiment of the present application, the organic material layer includes a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2, and may be used together with a phosphorescent dopant.

In an exemplary embodiment of the present application, the organic material layer includes a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2, and may be used together with an iridium-based dopant.

As a material for the phosphorescent dopant, materials known in the art can be used.

For example, phosphorescent dopant materials represented by LL'MX', LL'L''M, LMX'X'', L2MX', and L3M may be used, but the scope of the invention is not limited to these examples.

Here, L, L', L'', X', and X'' are mutually different bidentate ligands, and M is a metal forming an octahedral complex.

M can be iridium, platinum, osmium, and similar materials.

L is an anionic didentate ligand coordinated on M by sp2 carbon and heteroatoms through iridium-based dopants, and X can function to trap electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole) , (7,8-benzoquinoline), (thienylpyrazine), phenylpyridine, benzothienylpyrazine, 3-methoxy-2-phenylpyridine, thienylpyrazine, tolylpyridine and similar materials. Non-limiting examples of X' and X'' include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate and similar materials.

More specific examples thereof will be shown below, but the present application is not limited to these examples.

In an exemplary embodiment of the present application, as an iridium-based dopant, Ir(ppy) ₃ may be used as a green phosphorescent dopant.

In an exemplary embodiment of the present application, based on the entire light emitting layer, the content of the dopant may be 1% to 15%, preferably 3% to 10%, and more preferably 5% to 10%.

In an exemplary embodiment of the present application, there is provided an organic light emitting element, wherein an organic material layer of the organic light emitting element includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.

In an exemplary embodiment of the present application, an organic light-emitting element is provided, wherein the organic material layer of the organic light-emitting element includes a light-emitting layer, and the light-emitting layer includes a host material, and the host material includes the heterocyclic ring compound.

In the organic light emitting device of the present invention, the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include the heterocyclic compound.

In another organic light emitting device, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.

In yet another organic light emitting device, the organic material layer includes an electron transport layer, a light emitting layer or a hole blocking layer, and the electron transport layer, light emitting layer or hole blocking layer may contain the heterocyclic compound.

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

1 to 3 illustrate a stacking sequence of electrodes and organic material layers of an organic light emitting element according to an exemplary embodiment of the present application. However, the scope of the present application is not intended to be limited by these drawings, and structures of organic light-emitting devices known in the art are also applicable to the present application.

According to FIG. 1 , an organic light emitting element in which a positive electrode 200 , an organic material layer 300 and a negative electrode 400 are sequentially stacked on a substrate 100 is shown. However, the organic light emitting element is not limited to this structure, and as shown in FIG. 2 , an organic light emitting element in which a negative electrode, an organic material layer, and a positive electrode are sequentially stacked on a substrate may also be implemented.

FIG. 3 exemplifies the case where the organic material layer is a multilayer. The organic light emitting device according to FIG. 3 includes a hole injection layer 301 , a hole transport layer 302 , a light emitting layer 303 , a hole blocking layer 304 , an electron transport layer 305 and an electron injection layer 306 . However, the scope of the present application is not limited by the stack structure as described above, and layers other than the light emitting layer may be omitted and another necessary functional layer may be further added as needed.

In an exemplary embodiment of the present application, there is provided a method of manufacturing an organic light-emitting element, the method comprising: preparing a substrate; forming a first electrode on the substrate; forming an organic light-emitting device having one or more layers on the first electrode. a material layer; and forming a second electrode on the organic material layer, wherein the forming the organic material layer includes using an organic material layer composition according to an exemplary embodiment of the present application to form an organic material having one or more layers layer.

In an exemplary embodiment of the present application, there is provided a method of manufacturing an organic light-emitting element, in which the forming of the organic material layer is performed by premixing the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 compound and use a thermal vacuum deposition method to form the organic material layer.

Pre-mixing means that before depositing the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 on the organic material layer, the materials are first mixed, and the mixture is accommodated in a common container and mixed.

According to an exemplary embodiment of the present application, the pre-mixed material may be referred to as an organic material layer composition.

The organic material layer including Chemical Formula 1 may additionally include another material, if necessary.

If necessary, the organic material layer containing both Chemical Formula 1 and Chemical Formula 2 may additionally contain another material.

In the organic light-emitting element according to the exemplary embodiment of the present application, materials other than the compound of Chemical Formula 1 and the compound of Chemical Formula 2 will be exemplified below, but these materials are only exemplary and not intended to limit the present invention. scope of the application and may be substituted by materials known in the art.

As the positive electrode material, a material having a relatively high work function may be used, and a transparent conductive oxide, a metal, or a conductive polymer, and the like may be used. Specific examples of positive electrode materials 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 (indium zinc oxide, IZO); combinations of metals and oxides, such as ZnO:Al or SnO ₂ :Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-( Ethylene-1,2-dioxy)thiophene] (poly[3,4-(ethylene-1,2-dioxy)thiophene], PEDOT), polypyrrole and polyaniline; and similar materials, but not limited thereto.

As the negative electrode material, a material having a relatively low work function can be used, and a metal, a metal oxide, or a conductive polymer, and the like can be used. Specific examples of negative electrode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, zinc, aluminum, silver, tin, and lead, or alloys thereof; multilayer structural materials such as LiF/Al or LiO ₂ /Al; and similar materials, but not limited thereto.

As the hole injection material, known hole injection materials can also be used, and for example, a phthalocyanine compound, such as copper phthalocyanine disclosed in US Pat. No. 4,356,429; or document [Advanced Material (Advanced Material) , 6, p. 677 (1994)] star burst amine derivatives, such as tris (4-carbazolyl-9-ylphenyl) amine (tris (4-carbazolyl-9-ylphenyl) amine , TCTA), 4,4',4''-tri[phenyl(m-tolyl)amino]triphenylamine (4,4',4''-tri[phenyl(m-tolyl)amino]triphenylamine , m-MTDATA), 1,3,5-tris[4-(3-methylphenylanilino)phenyl]benzene (1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene, m-MTDAPB), polyaniline/dodecylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (which is a soluble conductive polymer), polyaniline/ Camphorsulfonic acid or polyaniline/poly(4-styrene-sulfonate), and similar materials.

As the hole transport material, pyrazoline derivatives, arylamine-based derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like can be used, and low-molecular-weight materials or polymer materials can also be used.

As the electron transport material, oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyano anthraquinone dimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, dibenzoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, and similar materials, and may also Use low molecular weight materials as well as polymeric materials.

As an electron injection material, for example, LiF is typically used in this technique, but the present application is not limited thereto.

As the luminescent material, red, green or blue luminescent materials may be used, and two or more luminescent materials may be mixed and used as necessary. In such cases, two or more luminescent materials are deposited as or used as separate supplies, or are premixed to be deposited as and used as one supply. In addition, a fluorescent material can also be used as a light-emitting material, but a phosphorescent material can also be used. As a light-emitting material, a material that emits light by combining holes and electrons each injected from a positive electrode and a negative electrode can also be used alone, but a material in which a host material participates in light emission together with a dopant material can also be used.

When the hosts of luminescent materials are mixed and used, hosts of the same series may also be mixed and used, and hosts of different series may also be mixed and used. For example, two or more types of materials selected from n-type host materials or p-type host materials can be used as the host material of the light emitting layer.

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

The heterocyclic compound according to the exemplary embodiment of the present application can be used even in devices including organic solar cells, organic photoconductors, organic transistors, and the like based on principles similar to those applied to organic light-emitting elements. play a role in organic electronic components. [invention method]

Hereinafter, the present description will be explained in more detail by examples, but these examples are provided only to exemplify the application and are not intended to limit the scope of the application. <Preparation Example> [Preparation Example 1] Preparation of Intermediate 1 (A) The synthetic method of intermediate A-2

1-Bromo-6-chlorodibenzo[b,d]furan (15 g, 53.28 mmol), phenylboronic acid (7.79 g, 63.93 mmol), tetrakis( A mixture of triphenylphosphine)palladium(0) (3.07 g, 2.66 mmol), potassium carbonate (22.09 g, 159.84 mmol) and 1,4-dioxane/water (150 mL/37.5 mL) was refluxed for 3 hours. After the reaction was completed, the temperature was lowered to room temperature, and then the obtained solid was washed with distilled water and methanol (MeOH) to obtain Intermediate A-2. (14 grams, 94%) The synthetic method of intermediate A-1

A-2 (14 g, 53.28 mmol), (4-bromophenyl)boronic acid (12.1 g, 60.2 mmol), tetrakis(triphenylphosphine) palladium (0 ) (2.9 g, 2.5 mmol), potassium carbonate (22.8 g, 150.6 mmol) and a mixture of 1,4-dioxane/water (140 ml/35 ml) was refluxed for 3 hours. After the reaction was completed, the temperature was lowered to room temperature, and then the obtained solid was washed with distilled water and MeOH to obtain Intermediate A-1. (18 grams, 90%) Synthetic method of intermediate 1 (A)

In A-1 (18 g, 45 mmol), bis (pinacolato) diboron (bis (pinacolato) diboron) (22.8 g, 90.2 mmol), Pd (dppf) Cl ₂ (1.6 g , 2.6 mmol) and KOAc (13.2 g, 135 mmol) were put into the reaction flask, 180 ml of 1,4-dioxane was added thereto, and then the resulting mixture was heated at 120°C 4 hours. After the reaction was complete, the base was removed, and then the solvent was concentrated and subjected to column purification to obtain Intermediate 1(A). (17 grams, 85%) [Preparation Example 2] Preparation of Intermediate 2 (B) The synthetic method of intermediate B-2

1-Bromo-7-chlorodibenzo[b,d]furan (15 g, 53.28 mmol), phenylboronic acid (7.79 g, 63.93 mmol), tetrakis( A mixture of triphenylphosphine)palladium(0) (3.07 g, 2.66 mmol), potassium carbonate (22.09 g, 159.84 mmol) and 1,4-dioxane/water (150 mL/37.5 mL) was refluxed for 3 hours. After the reaction was completed, the temperature was lowered to room temperature, and then the obtained solid was washed with distilled water and MeOH to obtain Intermediate B-2. (14 grams, 94%) The synthetic method of intermediate B-1

In the mixture of B-2 (14 g, 62 mmol), bis(pinacolate) diboron (25.5 g, 100 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxy Base-1,1'-biphenyl (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, Sphos) (4.1 g, 10 mmol), KOAc (14.7 g, 150 mmol ) and Pd ₂ (dba) ₃ (4.5 g, 5 mmol) into the reaction flask, 140 ml of 1,4-dioxane was added thereto, and then the resulting mixture was heated at 120°C 4 hours. After the reaction was complete, the base was removed, and then the solvent was concentrated and subjected to column purification to obtain Intermediate B-1. (16 g, 86%) Synthesis of Intermediate 2 (B)

In the mixture of B-1 (16 g, 43 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (9.72 g, 43 mmol), Pd(PPh ₃ ) ₄ (2.5 g, 2.2 mmol) and K ₂ CO ₃ (11.8 g, 86 mmol) were put into the reaction flask, tetrahydrofuran (Tetrahydrofuran, THF)/water (160 ml/32 ml) was heated for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, and then the obtained solid was washed with distilled water and MeOH to obtain Intermediate 2(B). (15 g, 80%) [Preparation Example 3] Preparation of Compound 1-1 (C) Synthetic method of compound 1-1 (C)

After intermediate 1 (12 g, 27.6 mmol), intermediate 2 (10 g, 23 mmol), Pd(PPh ₃ ) ₄ (1.3 g, 1.2 mmol) and K ₂ CO ₃ (9.5 g, 69 mmol) into the reaction flask, a mixture of 1,4-dioxane/water (100 mL/25 mL) was heated at 120° C. for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, and then the obtained solid was washed with distilled water and MeOH to obtain Compound 1-1(C). (14 grams, 84%)

The following compound (C) was synthesized in the same manner as in Preparation Example 1 to Preparation Example 3, except that Intermediate 1 (A) and Intermediate 2 (B) in Table 1 below were used. [Table 1] compound Intermediate 1 (A) Intermediate 2 (B) Compound (C) Yield (%) 1-2 85 1-3 83 1-4 80 1-5 81 1-6 82 1-7 83 1-8 88 1-9 85 1-10 83 1-11 84 1-12 83 1-13 80 1-14 88 1-15 86 1-18 85 1-19 83 1-20 84 1-21 88 1-22 86 1-23 84 1-24 85 1-25 83 1-26 80 1-27 81 1-28 82 1-29 83 1-30 88 1-31 85 1-32 83 1-33 84 1-34 83 1-35 80 1-38 85 1-39 83 1-40 80 1-41 81 1-42 82 1-43 83 1-44 88 1-45 85 1-46 83 1-47 84 1-48 83 1-49 80 1-50 83 1-51 81 1-52 80 1-53 81 1-54 82 1-55 84 1-58 88 1-59 85 1-60 86 1-61 85 1-62 87 1-63 88 1-64 85 1-65 84 1-66 82 1-67 80 1-68 83 1-69 88 1-70 85 1-71 86 1-72 85 1-73 87 1-74 88 1-75 85 1-78 84 1-79 82 1-80 80 [Preparation Example 4] Preparation of Compound 1-81 The preparation method of intermediate A'-2

Intermediate A'-2 was synthesized in the same manner as in Intermediate A-2 of Preparation Example 1. The preparation method of intermediate A'-1

A'-2 (10 g, 35.8 mmol), (4'-bromo-[1,1'-biphenyl]-4-yl)boronic acid (11.9 g, 43 millimoles), Pd(dba) ₂ (0.6 g, 1.79 millimoles), 2-dicyclohexylphosphino-2,4',6-triisopropylbiphenyl (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, Xphos) (1.7 g, 3.58 mol), K ₂ CO ₃ (14.8 g, 107.4 mmol) and 1,4-dioxane/water (100 ml/25 ml) were refluxed for 3 hours. After the reaction was completed, the temperature was lowered to room temperature, and then the obtained solid was washed with distilled water and MeOH to obtain Intermediate A'-1. (15 g, 88%) Synthesis of intermediate 1 (D)

In the mixture of A'-1 (10 g, 21 mmol), bis(pinacolate) diboron (10.6 g, 42 mmol), Pd(dppf)Cl ₂ (0.76 g, 1.05 mmol) and KOAc (6.18 g, 63 mmol) were put into the reaction flask, 100 mL of 1,4-dioxane was added thereto, and the resulting mixture was then heated at 120° C. for 4 hours. After the reaction was complete, the base was removed, and then the solvent was concentrated and subjected to column purification to obtain Intermediate 1(D). (8 g, 80%) Synthetic method of compound 1-81 (E)

After intermediate 1(D) (10 g, 19.14 mmol), IV (6.13 g, 22.9 mmol), Pd(PPh ₃ ) ₄ (1.09 g, 0.95 mmol) and K ₂ CO ₃ ( 7.9 g, 57.4 mmol) into the reaction flask, a mixture of 1,4-dioxane/water (100 ml/25 ml) was heated at 120° C. for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, and then the obtained solid was washed with distilled water and MeOH to obtain Compound 1-81(E). (10 grams, 83%)

The following compound (E) was synthesized in the same manner as in Preparation Example 4, except that other I, III, and IV in Table 2 below were used. [Table 2] compound I III IV Compound (E) Yield (%) 1-82 85 1-83 83 1-84 80 1-85 81 1-86 82 1-87 83 1-88 88 1-89 85 1-90 83 1-91 84 1-92 83 1-93 80 1-94 88 1-101 86 1-102 85 1-103 83 1-104 84 1-105 88 1-106 86 1-107 84 1-108 85 1-109 83 1-110 80 1-111 81 1-112 82 1-113 83 1-114 88 1-117 85 1-118 83 1-119 84 1-121 83 1-122 80 1-123 85 1-124 83 1-125 80 1-126 81 1-127 82 1-128 83 1-129 88 1-130 85 1-131 83 1-132 84 1-133 83 1-134 80 1-141 83 1-142 81 1-143 80 1-144 81 1-145 82 1-146 84 1-147 88 1-148 85 1-149 86 1-150 85 1-151 87 1-152 88 1-153 85 1-154 84 1-157 82 1-158 80 1-159 83 [Preparation Example 5] Preparation of Compound 1-161(F) The preparation method of intermediate G

Compound A-1 (1 g, 1 eq), Benzene-D6 (50 g, 210.8 eq) and CF ₃ SO ₃ H (14.4 g, 32.4 eq) were put into a reaction flask, and then reacted at 50° C. for 1 hour. After the reaction was completed, H ₂ O was added thereto for neutralization, then the resulting product was extracted with methylene chloride (MC) and H ₂ O, and then the organic layer was subjected to column purification, to obtain intermediate G. (0.65 g, 62%) Preparation method of compound B-1-1

Compound B-1-1 was prepared in the same manner as in B-1 of Preparation Example 1. The preparation method of intermediate 2-1 (H)

Intermediate 2-1(H) was prepared in the same manner as in Intermediate 2(B) of Production Example 2. Preparation method of compound 1-161(F)

Compound 1-161(F) was produced in the same manner as compound 1-1(C) of Production Example 3.

The following compound (F) was synthesized in the same manner as in Preparation Example 5, except that other Intermediate 1 (A) and Intermediate 2-1 (H) in Table 3 below were used. [table 3] compound Intermediate 1 (A) Intermediate 2 (B) Compound (F) Yield (%) 1-162 78 1-164 64 [Preparation Example 6] Preparation of Compound 1-170(I)

Compound C (10 g, 1 eq), Benzene-D6 (500 g, 287.93 eq) and CF ₃ SO ₃ H (245 g, 75 eq) were put into a reaction flask, and then stirred at 50° C. for 1 Hour. When the reaction was completed, H ₂ O was added thereto for neutralization, and the resulting product was extracted with MC and H ₂ O, and then subjected to column purification to obtain Compound 1-170(I). (7 grams, 68%) [Preparation Example 7] Preparation of Compound 2-1 The synthetic method of intermediate 1

In 3-bromo-9H-carbazole (10.0 g, 49.59 mmol), 2-bromophen-1-yl onium (A) (24.2 g, 148.77 mmol), Pd ₂ (dba) ₃ (2.27 g, 2.48 mmol), P(t-Bu) ₃ (2.42 ml, 9.92 mmol) and NaOtBu (9.53 g, 99.18 mmol) were put into the reaction flask, toluene (100 ml), and the resulting mixture was heated at 135°C for 15 hours. After the reaction was completed, extraction was performed with MC and H ₂ O, and then column purification was performed to obtain Intermediate 1. (14 g, 98%) Synthetic method of compound 2-1 (C)

After intermediate 1 (14 g, 43.4 mmol), (9-phenyl-9H-carbazol-3-yl)boronic acid (B) (14.9 g, 52 mmol), Pd(PPh ₃ ) ₄ (2.5 g, 2.17 mmol) and K ₂ CO ₃ (17.9 g, 130 mmol) were put into the reaction flask, and 1,4-dioxane/water (140 ml/35 ml) was heated for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, and then the obtained solid was washed with distilled water and MeOH to obtain Compound 2-1(C). (17 grams, 80%)

The following compound (C) was synthesized in the same manner as in Preparation Example 7 except that other A and B in Table 4 below were used. [Table 4] compound A B C Yield (%) 2-2 82 2-3 80 2-4 83 2-5 88 2-6 86 2-7 80 2-11 81 2-16 80 2-19 83 2-20 81 2-21 80 2-22 79 2-23 82 2-26 81 2-27 85 2-28 81 2-29 80 2-30 79 2-32 81 2-33 81 2-34 82 2-38 82 2-40 81 2-41 80 2-42 79 2-43 78 2-45 79 2-46 80 2-48 81 2-49 83 2-50 82 2-51 84 2-52 80 2-55 81 2-57 82 2-60 82 [Preparation Example 8] Preparation of Compound 2-61 The synthetic method of intermediate 2

After 3-bromo-9H-carbazole (10 g, 40.23 mmol) and 1000 mL of D6-benzene were put into the reaction flask, CF ₃ SO ₃ H (170 g, 1075 mmol ), and then the resulting mixture was stirred at 50 °C. When the reaction was complete, the resulting product was neutralized with D ₂ O, then extracted with MC and Na ₂ CO ₃ aqueous solution, and then column purified to obtain Intermediate 2. (10 g, 98%) Synthesis of Intermediate 3

After intermediate 2 (10 g, 39.5 mmol), bromobenzene (12.4 g, 79 mmol), Pd ₂ (dba) ₃ (1.81 g, 1.98 mmol), P(t-Bu) ₃ (1.93 ml, 7.9 mmol) and NaOtBu (11.4 g, 118.51 mmol) were put into the reaction flask, toluene (100 ml) was added thereto, and then the resulting mixture was heated at 135°C for 10 Hour. After the reaction was completed, extraction was performed with MC and H ₂ O, and then column purification was performed to obtain intermediate 3. (11 g, 84%) Synthesis of Intermediate 4

After 9H-carbazol-3-ylboronic acid (10 g, 47.3 mmol) and 1000 mL of D6-benzene were put into the reaction flask, CF ₃ SO ₃ H (170 g, 1075 mmol ear), and then the resulting mixture was stirred at 50 °C. When the reaction was complete, the resulting product was neutralized with D ₂ O, then extracted with MC and aqueous Na ₂ CO ₃ , and then column purified to obtain intermediate 4. (9 g, 87%) Synthesis of intermediate 5

After intermediate 4 (9 g, 41.3 mmol), bromobenzene (12.9 g, 82.5 mmol), Pd ₂ (dba) ₃ (1.89 g, 2.06 mmol), P(t-Bu) ₃ (2 ml, 8.25 mmol) and NaOtBu (7.93 g, 82.54 mmol) were put into the reaction flask, toluene (100 ml) was added thereto, and then the resulting mixture was heated at 135°C for 10 Hour. After the reaction was completed, extraction was performed with MC and H ₂ O, and then column purification was performed to obtain intermediate 5. (10 g, 82%) Synthetic method of compound 2-61 (F)

After intermediate 3 (10 g, 30.37 mmol), intermediate 5 (17.87 g, 60.75 mmol), Pd(PPh ₃ ) ₄ (1.3 g, 1.52 mmol) and K ₂ CO ₃ (12.59 g, 91.13 mmol) into the reaction flask, a mixture of 1,4-dioxane/water (140 mL/35 mL) was heated at 120 °C for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, and then the obtained solid was washed with distilled water and MeOH to obtain Compound 2-61(F). (13 grams, 85%)

The following compound (F) was synthesized in the same manner as in Preparation Example 8, except that other D and E in Table 5 below were used. [table 5] compound D. E. f Yield (%) 2-62 82 2-63 84 2-64 80 2-65 81 2-66 82 2-68 84 2-69 80 2-70 81 2-74 81 2-75 80 2-81 83 [Preparation Example 9] Preparation of Compound 2-81(H)

Compound G (10 g, 1 eq), D6-benzene (500 g, 287.93 eq) and CF ₃ SO ₃ (245 g, 75.04 eq) were put into a reaction flask, and then reacted at 50° C. for 1 hour . When the reaction was completed, H ₂ O was added thereto for neutralization, the resulting product was extracted with MC and H ₂ O, and then the organic layer was subjected to column purification to obtain compound 2-81 (H ). (7 grams, 66%)

Compounds H were each synthesized by synthesis in the same manner as in Preparation Example 9, except that Compound G in Table 6 below was used in Preparation Example 9. [Table 6] compound G h Yield (%) 2-81 63 2-82 62 2-83 64 2-85 60 2-86 61 2-87 61 2-88 62 2-89 62 2-90 64 2-92 60 2-102 61

In addition to the compounds described in Preparation Example 1 to Preparation Example 9, compounds related to Chemical Formula 1 and Chemical Formula 2 were also prepared in the same manner as described in the above Preparation Example.

The following Tables 7 and 8 are the field desorption-mass spectrometry (field desorption-mass spectrometry, FD-MS) data and 1H nuclear magnetic resonance (nuclear magnetic resonance, NMR) data of the synthesized compounds, and can be confirmed by the following data The desired compound was synthesized. [Table 7] compound FD-Mass compound FD-Mass 1-1 m/z= 717.81 (C51H31N3O2=717.24) 1-2 m/z= 717.81 (C51H31N3O2=717.24) 1-3 m/z= 717.81 (C51H31N3O2=717.24) 1-4 m/z= 717.81 (C51H31N3O2=717.24) 1-5 m/z= 717.81 (C51H31N3O2=717.24) 1-6 m/z= 717.81 (C51H31N3O2=717.24) 1-7 m/z= 717.81 (C51H31N3O2=717.24) 1-8 m/z= 717.81 (C51H31N3O2=717.24) 1-9 m/z= 717.81 (C51H31N3O2=717.24) 1-10 m/z= 717.81 (C51H31N3O2=717.24) 1-11 m/z= 717.81 (C51H31N3O2=717.24) 1-12 m/z= 717.81 (C51H31N3O2=717.24) 1-13 m/z= 717.81 (C51H31N3O2=717.24) 1-14 m/z= 717.81 (C51H31N3O2=717.24) 1-15 m/z= 717.81 (C51H31N3O2=717.24) 1-16 m/z= 717.81 (C51H31N3O2=717.24) 1-17 m/z= 793.91 (C57H35N3O2= 793.27) 1-18 m/z= 793.91 (C57H35N3O2= 793.27) 1-19 m/z= 793.91 (C57H35N3O2= 793.27) 1-20 m/z= 793.91 (C57H35N3O2= 793.27) 1-21 m/z= 733.88 (C51H31N3OS= 733.21) 1-22 m/z= 733.88 (C51H31N3OS= 733.21) 1-23 m/z= 733.88 (C51H31N3OS= 733.21) 1-24 m/z= 733.88 (C51H31N3OS= 733.21) 1-25 m/z= 733.88 (C51H31N3OS= 733.21) 1-26 m/z= 733.88 (C51H31N3OS= 733.21) 1-27 m/z= 733.88 (C51H31N3OS= 733.21) 1-28 m/z= 733.88 (C51H31N3OS= 733.21) 1-29 m/z= 733.88 (C51H31N3OS= 733.21) 1-30 m/z= 733.88 (C51H31N3OS= 733.21) 1-31 m/z= 733.88 (C51H31N3OS= 733.21) 1-32 m/z= 733.88 (C51H31N3OS= 733.21) 1-33 m/z= 733.88 (C51H31N3OS= 733.21) 1-34 m/z= 733.88 (C51H31N3OS= 733.21) 1-35 m/z= 733.88 (C51H31N3OS= 733.21) 1-36 m/z= 809.97 (C57H35N3OS= 809.25) 1-37 m/z= 809.97 (C57H35N3OS= 809.25) 1-38 m/z= 809.97 (C57H35N3OS= 809.25) 1-39 m/z= 809.97 (C57H35N3OS= 809.25) 1-40 m/z= 809.97 (C57H35N3OS= 809.25) 1-41 m/z= 749.94 (C51H31N3S2= 749.20) 1-42 m/z= 749.94 (C51H31N3S2= 749.20) 1-43 m/z= 749.94 (C51H31N3S2= 749.20) 1-44 m/z= 749.94 (C51H31N3S2= 749.20) 1-45 m/z= 749.94 (C51H31N3S2= 749.20) 1-46 m/z= 749.94 (C51H31N3S2= 749.20) 1-47 m/z= 749.94 (C51H31N3S2= 749.20) 1-48 m/z= 749.94 (C51H31N3S2= 749.20) 1-49 m/z= 749.94 (C51H31N3S2= 749.20) 1-50 m/z= 749.94 (C51H31N3S2= 749.20) 1-51 m/z= 749.94 (C51H31N3S2= 749.20) 1-52 m/z= 749.94 (C51H31N3S2= 749.20) 1-53 m/z= 749.94 (C51H31N3S2= 749.20) 1-54 m/z= 749.94 (C51H31N3S2= 749.20) 1-55 m/z= 749.94 (C51H31N3S2= 749.20) 1-56 m/z= 826.04 (C57H35N3S2= 825.23) 1-57 m/z= 826.04 (C57H35N3S2= 825.23) 1-58 m/z= 826.04 (C57H35N3S2= 825.23) 1-59 m/z= 826.04 (C57H35N3S2= 825.23) 1-60 m/z= 826.04 (C57H35N3S2= 825.23) 1-61 m/z= 733.88 (C51H31N3OS= 733.21) 1-62 m/z= 733.88 (C51H31N3OS= 733.21) 1-63 m/z= 733.88 (C51H31N3OS= 733.21) 1-64 m/z= 733.88 (C51H31N3OS= 733.21) 1-65 m/z= 733.88 (C51H31N3OS= 733.21) 1-66 m/z= 733.88 (C51H31N3OS= 733.21) 1-67 m/z= 733.88 (C51H31N3OS= 733.21) 1-68 m/z= 733.88 (C51H31N3OS= 733.21) 1-69 m/z= 733.88 (C51H31N3OS= 733.21) 1-70 m/z= 733.88 (C51H31N3OS= 733.21) 1-71 m/z= 733.88 (C51H31N3OS= 733.21) 1-72 m/z= 733.88 (C51H31N3OS= 733.21) 1-73 m/z= 733.88 (C51H31N3OS= 733.21) 1-74 m/z= 733.88 (C51H31N3OS= 733.21) 1-75 m/z= 733.88 (C51H31N3OS= 733.21) 1-76 m/z= 809.97 (C57H35N3OS= 809.25) 1-77 m/z= 809.97 (C57H35N3OS= 809.25) 1-78 m/z= 809.97 (C57H35N3OS= 809.25) 1-79 m/z= 809.97 (C57H35N3OS= 809.25) 1-80 m/z= 809.97 (C57H35N3OS= 809.25) 1-81 m/z= 627.73 (C45H29N3O= 627.23) 1-82 m/z= 627.73 (C45H29N3O= 627.23) 1-83 m/z= 627.73 (C45H29N3O= 627.23) 1-84 m/z= 627.73 (C45H29N3O= 627.23) 1-85 m/z= 627.73 (C45H29N3O= 627.23) 1-86 m/z= 627.73 (C45H29N3O= 627.23) 1-87 m/z= 627.73 (C45H29N3O= 627.23) 1-88 m/z= 627.73 (C45H29N3O= 627.23) 1-89 m/z= 627.73 (C45H29N3O= 627.23) 1-90 m/z= 627.73 (C45H29N3O= 627.23) 1-91 m/z= 627.73 (C45H29N3O= 627.23) 1-92 m/z= 627.73 (C45H29N3O= 627.23) 1-93 m/z= 627.73 (C45H29N3O= 627.23) 1-94 m/z= 627.73 (C45H29N3O= 627.23) 1-95 m/z= 703.83 (C51H33N3O= 703.26) 1-96 m/z= 703.83 (C51H33N3O= 703.26) 1-97 m/z= 703.83 (C51H33N3O= 703.26) 1-98 m/z= 703.83 (C51H33N3O= 703.26) 1-99 m/z= 703.83 (C51H33N3O= 703.26) 1-100 m/z= 703.83 (C51H33N3O= 703.26) 1-101 m/z= 703.83 (C51H33N3O= 703.26) 1-102 m/z= 703.83 (C51H33N3O= 703.26) 1-103 m/z= 779.92 (C57H37N3O= 779.29) 1-104 m/z= 779.92 (C57H37N3O= 779.29) 1-105 m/z= 703.83 (C51H33N3O= 703.26) 1-106 m/z= 703.83 (C51H33N3O= 703.26) 1-107 m/z= 779.92 (C57H37N3O= 779.29) 1-108 m/z= 779.92 (C57H37N3O= 779.29) 1-109 m/z= 703.83 (C51H33N3O= 703.26) 1-110 m/z= 703.83 (C51H33N3O= 703.26) 1-111 m/z= 779.92 (C57H37N3O= 779.29) 1-112 m/z= 779.92 (C57H37N3O= 779.29) 1-113 m/z= 703.83 (C51H33N3O= 703.26) 1-114 m/z= 703.83 (C51H33N3O= 703.26) 1-115 m/z= 779.92 (C57H37N3O= 779.29) 1-116 m/z= 779.92 (C57H37N3O= 779.29) 1-117 m/z= 703.83 (C51H33N3O= 703.26) 1-118 m/z= 703.83 (C51H33N3O= 703.26) 1-119 m/z= 703.83 (C51H33N3O= 703.26) 1-120 m/z= 779.92 (C57H37N3O= 779.29) 1-121 m/z= 643.80 (C45H29N3S= 643.21) 1-122 m/z= 643.80 (C45H29N3S= 643.21) 1-123 m/z= 643.80 (C45H29N3S= 643.21) 1-124 m/z= 643.80 (C45H29N3S= 643.21) 1-125 m/z= 643.80 (C45H29N3S= 643.21) 1-126 m/z= 643.80 (C45H29N3S= 643.21) 1-127 m/z= 643.80 (C45H29N3S= 643.21) 1-128 m/z= 643.80 (C45H29N3S= 643.21) 1-129 m/z= 643.80 (C45H29N3S= 643.21) 1-130 m/z= 643.80 (C45H29N3S= 643.21) 1-131 m/z= 643.80 (C45H29N3S= 643.21) 1-132 m/z= 643.80 (C45H29N3S= 643.21) 1-133 m/z= 643.80 (C45H29N3S= 643.21) 1-134 m/z= 643.80 (C45H29N3S= 643.21) 1-135 m/z= 719.89 (C51H33N3S= 719.24) 1-136 m/z= 719.89 (C51H33N3S= 719.24) 1-137 m/z= 719.89 (C51H33N3S= 719.24) 1-138 m/z= 719.89 (C51H33N3S= 719.24) 1-139 m/z= 719.89 (C51H33N3S= 719.24) 1-140 m/z= 719.89 (C51H33N3S= 719.24) 1-141 m/z= 719.89 (C51H33N3S= 719.24) 1-142 m/z= 719.89 (C51H33N3S= 719.24) 1-143 m/z= 795.99 (C57H37N3S= 795.27) 1-144 m/z= 795.99 (C57H37N3S= 795.27) 1-145 m/z= 719.89 (C51H33N3S= 719.24) 1-146 m/z= 719.89 (C51H33N3S= 719.24) 1-147 m/z= 795.99 (C57H37N3S= 795.27) 1-148 m/z= 795.99 (C57H37N3S= 795.27) 1-149 m/z= 719.89 (C51H33N3S= 719.24) 1-150 m/z= 719.89 (C51H33N3S= 719.24) 1-151 m/z= 795.99 (C57H37N3S= 795.27) 1-152 m/z= 795.99 (C57H37N3S= 795.27) 1-153 m/z= 719.89 (C51H33N3S= 719.24) 1-154 m/z= 719.89 (C51H33N3S= 719.24) 1-155 m/z= 795.99 (C57H37N3S= 795.27) 1-156 m/z= 795.99 (C57H37N3S= 795.27) 1-157 m/z= 719.89 (C51H33N3S= 719.24) 1-158 m/z= 719.89 (C51H33N3S= 719.24) 1-159 m/z= 719.89 (C51H33N3S= 719.24) 1-160 m/z= 795.99 (C57H37N3S= 795.27) 1-161 m/z= 728.88 (C51H20D11N3O2= 728.31) 1-162 m/z= 728.88 (C51H20D11N3O2= 728.31) 1-163 m/z= 728.88 (C51H20D11N3O2= 728.31) 1-164 m/z= 728.88 (C51H20D11N3O2= 728.31) 1-165 m/z= 744.94 (C51H20D11N3OS= 744.29 1-166 m/z= 738.91 (C51H26D5N3OS= 738.25) 1-167 m/z= 754.97 (C51H26D5N3S2= 754.23) 1-168 m/z= 754.97 (C51H26D5N3S2= 754.23) 1-169 m/z= 733.91 (C51H15D16N3O2= 733.34) 1-170 m/z= 749.00 (C51D31N3O2= 748.44) 1-171 m/z= 637.79 (C45H19D10N3O= 637.29) 1-172 m/z= 637.79 (C45H19D10N3O= 637.29) 1-173 m/z= 638.80 (C45H18D11N3O= 638.30) 1-174 m/z= 638.80 (C45H18D11N3O= 638.30) 1-175 m/z= 741.89 (C51H21D11N3O= 741.34) 1-176 m/z= 741.89 (C51H21D11N3O= 741.34) 1-177 m/z= 717.91 (C51H91D14N3O= 717.35) 1-178 m/z= 737.03 (C51D33N3O= 736.47) 1-179 m/z= 794.01 (C57H23D14N3O= 793.38) 1-180 m/z= 794.01 (C57H23D14N3O= 793.38) 2-1 m/z= 484.59(C36H24N2=484.19) 2-2 m/z= 560.69(C42H28N2=560.23) 2-3 m/z= 560.69(C42H28N2=560.23) 2-4 m/z= 560.69(C42H28N2=560.23) 2-5 m/z= 636.78(C48H32N2=636.26) 2-6 m/z= 636.78(C48H32N2=636.26) 2-7 m/z= 636.78(C48H32N2=636.26) 2-8 m/z= 543.65(C40H26N2=543.21) 2-9 m/z= 543.65(C40H26N2=543.21) 2-10 m/z= 600.75(C45H35N2=600.26) 2-11 m/z= 600.75(C45H35N2=600.26) 2-12 m/z= 724.89(C55H36N2=724.29) 2-13 m/z= 724.89(C55H36N2=724.29) 2-14 m/z= 724.89(C55H36N2=724.29) 2-15 m/z= 724.89(C55H36N2=724.29) 2-16 m/z= 634.77(C48H30N2=634.24) 2-17 m/z= 509.60(C37H23N3=509.19) 2-18 m/z= 742.98(C54H38N2Si=742.28) 2-19 m/z= 636.78(C48H32N2=636.26) 2-20 m/z= 636.78(C48H32N2=636.26) 2-21 m/z= 636.78(C48H32N2=636.26) 2-22 m/z= 712.88(C54H36N2=712.29) 2-23 m/z= 712.88(C54H36N2=712.29) 2-24 m/z= 712.88(C54H36N2=712.29) 2-25 m/z= 710.86(C54H34N2=710.27) 2-26 m/z= 712.88(C54H36N2=712.29) 2-27 m/z= 712.88(C54H36N2=712.29) 2-28 m/z= 712.88(C54H36N2=712.29) 2-29 m/z= 712.88(C54H36N2=712.29) 2-30 m/z= 712.88(C54H36N2=712.29) 2-31 m/z= 710.86(C54H34N2=710.27) 2-32 m/z= 636.78(C48H32N2=636.26) 2-33 m/z= 712.88(C54H36N2=712.29) 2-34 m/z= 712.88(C54H36N2=712.29) 2-35 m/z= 788.97(C60H40N2=788.32) 2-36 m/z= 686.84(C52H34N2=686.27) 2-37 m/z= 788.97(C60H40N2=788.32) 2-38 m/z= 788.97(C60H40N2=788.32) 2-39 m/z= 686.84(C52H34N2=686.27) 2-40 m/z= 686.84(C52H34N2=686.27) 2-41 m/z= 494.65(C36H14D10N2=494.26) 2-42 m/z= 654.89(C48H14D18N2=654.37) 2-43 m/z= 574.77(C41H14D14N2=574.31) 2-44 m/z= 650.86(C48H14D16N2=650.34) 2-45 m/z= 654.89(C48H14D18N2=654.37) 2-46 m/z= 654.89(C48H14D18N2=654.37) 2-47 m/z= 654.89(C48H14D18N2=654.37) 2-48 m/z=654.89(C48H14D18N2=654.37) 2-49 m/z= 654.89(C48H14D18N2=654.37) 2-50 m/z= 654.89(C48H14D18N2=654.37) 2-51 m/z= 735.01(C54H14D22N2=734.43) 2-52 m/z= 735.01(C54H14D22N2=734.43) 2-53 m/z= 730.98(C54H14D20N2=730.40) 2-54 m/z= 735.01(C54H14D22N2=734.43) 2-55 m/z=735.01(C54H14D22N2=734.43) 2-56 m/z= 815.13(C60H14D26N2=814.48) 2-57 m/z= 815.13(C60H14D26N2=814.48) 2-58 m/z= 815.13(C60H14D26N2=814.48) 2-59 m/z= 815.13(C60H14D26N2=814.48) 2-60 m/z= 666.86(C48H14D16N2O=666.34) 2-61 m/z= 498.68(C36H10D14N2=498.28) 2-62 m/z= 650.87(C48H18D14N2=650.34) 2-63 m/z= 574.77(C41H14D14N2=574.31) 2-64 m/z= 648.85(C48H16D14N2=648.33) 2-65 m/z= 650.87(C48H18D14N2=650.34) 2-66 m/z= 650.87(C48H18D14N2=650.34) 2-67 m/z= 650.87(C48H18D14N2=650.34) 2-68 m/z= 650.87(C48H18D14N2=650.34) 2-69 m/z= 650.87(C48H18D14N2=650.34) 2-70 m/z=650.87(C48H18D14N2=650.34) 2-71 m/z= 726.96(C54H22D14N2=726.38) 2-72 m/z= 726.96(C54H22D14N2=726.38) 2-73 m/z= 724.95(C54H20D14N2=724.36) 2-74 m/z= 726.96(C54H22D14N2=726.38) 2-75 m/z= 726.96(C54H22D14N2=726.38) 2-76 m/z= 803.06(C60H26D14N2=802.41) 2-77 m/z= 803.06(C60H26D14N2=802.41) 2-78 m/z= 803.06(C60H26D14N2=802.41) 2-79 m/z= 803.06(C60H26D14N2=802.41) 2-80 m/z= 803.06(C60H26D14N2=802.41) 2-81 m/z= 508.74(C36D24N2=508.34) 2-82 m/z= 668.98(C48D32N2=668.46) 2-83 m/z= 588.86(C42D28N2=588.40) 2-84 m/z= 664.95(C48D30N2=664.43) 2-85 m/z= 668.98(C48D32N2=668.46) 2-86 m/z= 668.98(C48D32N2=668.46) 2-87 m/z= 668.98(C48D32N2=668.46) 2-88 m/z= 668.98(C48D32N2=668.46) 2-89 m/z= 668.98(C48D32N2=668.46) 2-90 m/z= 668.98(C48D32N2=668.46) 2-91 m/z= 749.10(C54D36N2=748.51) 2-92 m/z= 749.10(C54D36N2=748.51) 2-93 m/z= 745.07(C54D34N2=744.49) 2-94 m/z= 749.10(C54D36N2=748.51) 2-95 m/z= 749.10(C54D36N2=748.51) 2-96 m/z= 829.22(C60D40N2=828.57) 2-97 m/z= 829.22(C60D40N2=828.57) 2-98 m/z= 829.22(C60D40N2=828.57) 2-99 m/z= 829.22(C60D40N2=828.57) 2-100 m/z= 680.95(C48D30N2O=680.42) 2-101 m/z= 697.02(C48D30N2S=696.40) 2-102 m/z= 829.22(C60D40N2=828.57) 2-103 m/z= 632.95(C45D32N2=632.46) 2-104 m/z= 713.07(C51D36N2=712.51) [Table 8] compound ¹ H NMR (CDCl3, 300 MHz) 1-1 δ = 8.28(d, 2H), 7.95(d, 1H), 7.85-7.75(m, 11H), 7.64-7.62(m, 3H), 7.51-7.38(m, 12H) 1-6 δ =8.28(d, 2H), 7.95(d, 2H), 7.85-7.75(m, 9H), 7.64(m, 3H), 7.51-7.38(m, 13H) 1-11 δ =8.28(d, 2H), 7.95-7.75(m, 11H), 7.66-7.62(m, 3H), 7.51-7.25(m, 14H) 1-17 δ =8.28(d, 2H), 7.95(d, 2H), 7.85-7.75(m, 9H), 7.64-7.41(m, 20H), 7.25(m, 2H) 1-29 δ =8.28(d, 2H), 8.11-8.08(m, 2H), 7.95-7.94(m, 2H), 7.85-7.75(m, 10H), 7.64-7.41(m, 13H), 7.25(m, 2H ) 1-31 δ =8.28(d, 2H), 8.11-8.08(m, 2H), 7.94-7.79(m, 12H), 7.66(d, 1H), 7.56-7.25(m, 14H) 1-33 δ =8.45(d, 1H), 8.28(m, 2H), 8.04-7.95(m, 3H), 7.85-7.75(m, 9H), 7.64-7.62(m, 2H), 7.52-7.41(m, 12H ) 1-37 δ =8.28(d, 2H), 8.11-8.04(m, 4H), 7.95(d, 1H), 7.85-7.77(m, 9H), 7.64-7.62(m, 2H), 7.52-7.41(m, 15H ), 7.25(m, 2H) 1-41 δ =8.41(d, 1H), 8.28(m, 2H), 8.20(d, 1H), 8.11-8.08(m, 2H), 7.94(d, 2H), 7.85-7.79(m, 9H), 7.58- 7.41(m, 12H), 7.25(m, 2H) 1-42 δ =8.41(d, 1H), 8.28(m, 2H), 8.20(d, 1H), 8.11-8.08(m, 2H), 8.00-7.94(m, 3H), 7.86-7.79(m, 7H), 7.58-7.41(m, 13H), 7.25(m, 2H) 1-44 δ =8.41(m, 2H), 8.28(m, 2H), 8.20(m, 2H), 8.11-8.08(m, 2H), 7.94(m, 1H), 7.85-7.79(m, 6H), 7.58- 7.41(m, 14H), 7.25(m, 2H) 1-52 δ =8.45(d, 1H), 8.25(m, 2H), 8.11-8.08(m, 2H), 7.98-7.94(m, 3H), 7.85-7.75(m, 7H), 7.56-7.41(m, 14H ), 7.25(m, 2H) 1-53 δ =8.45(d, 2H), 8.28(m, 2H), 8.11-7.94(m, 6H), 7.85-7.77(m, 8H), 7.56-7.41(m, 12H), 7.25(m, 2H) 1-55 δ =8.45-8.44(m, 2H), 8.28(m, 2H), 8.20(m, 1H), 7.98-7.79(m, 9H), 7.58-7.41(m, 15H), 7.25(m, 2H) 1-59 δ =8.45(d, 1H), 8.24(m, 2H), 8.11-7.94(m, 6H), 7.82-7.77(m, 6H), 7.70(s, 2H), 7.57-7.41(m, 18H) 1-61 δ =8.41(m, 1H), 8.28(m, 2H), 8.20(m, 1H), 7.95-7.94(m, 2H), 7.85-7.75(m, 9H), 7.64-7.41(m, 14H), 7.25(m, 2H) 1-69 δ =8.28(m, 2H), 8.11-8.05(m, 3H), 7.95-7.94(m, 2H), 7.85-7.75(m, 9H), 7.64-7.41(m, 13H), 7.25(m, 2H ) 1-70 δ =8.28(m, 2H), 8.00-7.75(m, 15H), 7.64-7.41(m, 13H), 7.25(m, 2H) 1-71 δ =8.45(d, 1H), 8.28(m, 2H), 7.98-7.75(m, 12H), 7.64-7.62(m, 2H), 7.51-7.41(m, 12H), 7.25(m, 2H) 1-74 δ =8.41(d, 1H), 8.28(m, 2H), 8.20(m, 1H), 7.94-7.79(m, 7H), 7.66-7.25(m, 20H) 1-76 δ =8.28(m, 2H), 8.11-8.05(m, 3H), 7.95-7.94(m, 2H), 7.85-7.79(m, 8H), 7.64-7.41(m, 18H), 7.25(m, 2H ) 1-81 δ =8.21(m, 4H), 7.85-7.75(m, 7H), 7.62(m, 1H), 7.51-7.38(m, 11H), 7.25(m, 6H) 1-87 δ =8.28(m, 4H), 7.95(m, 2H), 7.85(d, 2H), 7.75(d, 2H), 7.64(d, 2H), 7.51-7.41(m, 11H), 7.25(m, 6H) 1-92 δ =8.28(m, 4H), 7.85-7.81(m, 5H), 7.72-7.71(m, 2H), 7.52-7.38(m, 12H), 7.25(m, 6H) 1-109 δ =8.28(m, 2H), 7.85-7.72(m, 10H), 7.62(m, 1H), 7.52-7.41(m, 12H), 7.25(m, 6H) 1-112 δ =7.85-7.72(m, 12H), 7.62(m, 1H), 7.51-7.41(m, 14H), 7.25(m, 10H) 1-123 δ =8.41(m, 1H), 8.28(m, 4H), 8.20(m, 1H), 8.11-8.05(m, 3H), 7.85(m, 2H), 7.58-7.41(m, 12H), 7.25( m, 6H) 1-127 δ =8.28(m, 4H), 8.11-8.05(m, 6H), 7.85(m, 2H), 7.52-7.41(m, 11H), 7.25(m, 6H) 1-149 δ =8.28(m, 2H), 8.00-7.94(m, 3H), 7.93-7.79(m, 8H), 7.5697.41(m, 12H), 7.25(m, 8H) 1-156 δ =8.41(m, 1H), 8.28(m, 2H), 8.20(m, 1H), 7.88-7.79(m, 8H), 7.58-7.41(m, 17H), 7.25(m, 8H) 1-163 δ =8.28(m, 2H), 7.95(d, 1H), 7.85-7.75(m, 6H), 7.64-7.62(m, 2H), 7.51-7.41(m, 7H), 7.25(d, 2H) 1-172 δ =7.95(m, 1H), 7.85-7.75(m, 6H), 7.64-7.62(m, 2H), 7.51-7.44(m, 4H), 7.25(m, 6H) 2-3 δ =8.55(d, 1H), 8.18-8.09(m, 3H), 8.00-7.87(m, 3H), 7.77(s, 2H), 7.58-7.25(m, 18H) 2-4 δ =8.55(d, 1H), 8.18-8.12(m, 2H), 8.00-7.84(m, 3H), 7.79-7.77(m, 4H), 7.68-7.25(m, 22H) 2-7 δ =8.55(d, 1H), 8.18-8.09(m, 4H), 8.00-7.94(m, 2H), 7.87(m, 1H), 7.77(m, 2H), 7.69-7.63(m, 2H), 7.52-7.25(m, 20H) 2-27 δ =8.55(m, 1H), 8.18-8.09(m, 4h), 8.00-7.94(m, 2H), 7.77(m, 2H) 2-28 δ =8.55(m, 1H), 8.18-8.09(m, 3H), 8.00-8.79(m, 2H), 7.87(m, 1H), 7.79-7.77(m, 4H), 7.69-7.63(m, 4H ), 7.52-7.25(m, 12H) 2-29 δ =8.55(m, 1H), 8.18-8.09(m, 3H), 8.00-7.94(m, 2H0, 7.87(m, 1H), 7.87(m, 1H), 7.79-7.77(m, 4H), 7.69 -7.63(m, 4H), 7.52-7.25(m, 21H) 2-32 δ =8.55(m, 1H), 8.18-8.12(m, 2H), 8.00-7.87(m, 3H), 7.79-7.77(m, 6H), 7.69-7.63(m, 6H), 7.52-7.25(m , 14H) 2-34 δ =8.55(m, 1H), 8.18-8.12(m, 2H), 8.00-7.87(m, 3H), 7.79-7.77(m, 6H), 7.67-7.63(m, 6H), 7.52-7.25(m , 18H) 2-38 δ =8.55(m, 1H), 8.18-8.12(m, 2H), 8.05-7.87(m, 6H), 7.79-7.77(m, 4H), 7.69-7.63(m, 4H), 7.52-7.25(m , 23H) 2-46 δ =8.55(d, 1H), 8.18-8.12(m, 2H), 8.00-7.87(m, 3H), 7.77-7.63(m, 4H), 7.50(m, 1H), 7.33-7.25(m, 3H ) 2-49 δ =8.55(d, 1H), 8.18-8.12(m, 2H), 8.00-7.87(m, 3H), 7.77-7.63(m, 4H), 7.50(m, 1H), 7.33-7.25(m, 3H ) 2-62 δ =7.79(m, 4H), 7.68(m. 4H), 7.52-7.41(m, 10H) 2-65 δ =7.79(m, 2H), 7.70-7.68(m, 3H), 7.58-7.41(m, 13H) 2-70 δ =7.79(m, 4H), 7.68(m, 4H), 7.52-7.41(m, 10H) <Experimental example 1> - Manufacture of organic light-emitting device

The glass substrate in which ITO was thinly coated to have a thickness of 1,500 angstroms was ultrasonically cleaned with distilled water. When the wash with distilled water is complete, the glass substrate is ultrasonically washed with solvents such as acetone, methanol, and isopropanol, dried, and then subjected to UV exposure in an ultraviolet (UV) washing machine. 5 minutes of ultraviolet ozone (ultraviolet ozone, UVO) treatment. After that, the substrate is transferred to a plasma cleaning machine (PT), and then subjected to plasma treatment under vacuum to achieve ITO work function and remove residual film, and the substrate is transferred to a thermal deposition device for organic deposition.

As a common layer, a hole injection layer 4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine (4,4' ,4''-tris[2-naphthyl(phenyl)amino]triphenylamine, 2-TNATA) and hole transport layer N,N'-bis(1-naphthyl)-N,N'-diphenyl-(1 ,1'-biphenyl)-4,4'-diamine (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'- diamine, NPB).

A light-emitting layer was thermally vacuum deposited thereon as described below. A light-emitting layer with a thickness of 360 angstroms was deposited by using the heterocyclic compound of Chemical Formula 1 in Table 9 below as a host, and using tris(2-phenylpyridine)iridium (Ir(ppy) ₃ ) as a green phosphorescent dopant dopant to dope the host with Ir(ppy) ₃ in an amount of 7%. After that, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (2,9-dimethyl-4,7- diphenyl-1,10-phenanthroline, BCP), and deposited Alq ₃ as an electron transport layer with a thickness of 200 angstroms on it. Finally, lithium fluoride (LiF) was deposited with a thickness of 10 Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) negative electrode was deposited with a thickness of 1200 Å on the electron injection layer to form a negative electrode , thereby fabricating organic electroluminescent elements.

Simultaneously, for each material, all organic compounds required for the fabrication of organic light-emitting diode (OLED) elements were subjected to vacuum sublimed purification at 10 ^-6 Torr to 10 ^-8 Torr. ), and used to make OLEDs. For the organic electroluminescence element manufactured as described above, electroluminescence (EL) characteristics were measured by M7000 manufactured by McScience Inc., and based on the measurement results, by McScience Inc. The manufactured lifetime measuring device (M6000) measured T ₉₀ when the reference luminance was 6,000 candela/square meter (cd/m ² ). Table 9 shows the results of measuring the driving voltage, luminous efficiency, color coordinates (Commission Internationale de l´Eclairage, CIE) and service life of the organic light emitting element manufactured according to the present invention. [Table 9] compound Driving Voltage (Volts) Efficiency (cd/area) Color coordinates (x, y) Service life (T ₉₀ ) Comparative example 1 A 5.01 60.3 (0.286, 0.686) 89 Comparative example 2 B 5.62 65.4 (0.274, 0.678) 92 Comparative example 3 C 6.32 66.2 (0.279, 0.677) 95 Comparative example 4 D. 6.88 61.7 (0.278, 0.677) 96 Comparative Example 5 E. 6.32 60.3 (0.286, 0.686) 91 Example 1 1-1 4.71 89.2 (0.277, 0.669) 103 Example 2 1-2 4.72 89.3 (0.281, 0.679) 102 Example 3 1-3 4.76 90.2 (0.280, 0.677) 104 Example 4 1-4 4.70 90.7 (0.279, 0.676) 105 Example 5 1-7 4.67 88.2 (0.272, 0.669) 104 Example 6 1-10 4.66 89.4 (0.271, 0.671) 105 Example 7 1-15 4.72 87.2 (0.275, 0.672) 102 Example 8 1-20 4.69 88.3 (0.279, 0.675) 105 Example 9 1-29 4.63 90.9 (0.280, 0.676) 107 Example 10 1-30 4.62 90.1 (0.278, 0.672) 108 Example 11 1-32 4.63 91.3 (0.283, 0.687) 108 Example 12 1-33 4.64 90.2 (0.286, 0.686) 106 Example 13 1-34 4.66 91.1 (0.274, 0.678) 108 Example 14 1-35 4.60 92.2 (0.279, 0.677) 110 Example 15 1-40 4.60 84.2 (0.278, 0.677) 109 Example 16 1-41 4.57 93.3 (0.276, 0.671) 117 Example 17 1-42 4.59 93.4 (0.284, 0.687) 111 Example 18 1-43 4.60 90.4 (0.281, 0.684) 114 Example 19 1-44 4.60 91.2 (0.283, 0.681) 118 Example 20 1-45 4.58 89.5 (0.279, 0.681) 119 Example 21 1-46 4.58 88.7 (0.280, 0.679) 116 Example 22 1-47 4.57 90.2 (0.281, 0.678) 114 Example 23 1-49 4.58 88.2 (0.278, 0.682) 118 Example 24 1-51 4.58 90.3 (0.286, 0.692) 119 Example 25 1-54 4.60 88.2 (0.274, 0.672) 115 Example 26 1-55 4.59 90.4 (0.278, 0.678) 115 Example 27 1-57 4.60 88.4 (0.277, 0.674) 116 Example 28 1-61 4.58 92.2 (0.279, 0.674) 115 Example 29 1-62 4.59 89.3 (0.278, 0.677) 116 Example 30 1-69 4.53 93.3 (0.279, 0.681) 119 Example 31 1-70 4.54 93.4 (0.280, 0.679) 118 Example 32 1-71 4.53 94.3 (0.281, 0.678) 118 Example 33 1-72 4.53 95.4 (0.278, 0.682) 123 Example 34 1-73 4.55 92.3 (0.286, 0.692) 118 Example 35 1-74 4.51 89.2 (0.274, 0.672) 118 Example 36 1-75 4.42 97.4 (0.278, 0.678) 122 Example 37 1-76 4.55 97.4 (0.277, 0.674) 117 Example 38 1-77 4.52 95.6 (0.279, 0.674) 119 Example 39 1-80 4.41 97.4 (0.280, 0.676) 123 Example 40 1-81 4.71 89.3 (0.278, 0.672) 103 Example 41 1-86 4.72 90.2 (0.283, 0.687) 102 Example 42 1-87 4.76 90.7 (0.286, 0.686) 104 Example 43 1-90 4.70 88.2 (0.274, 0.678) 105 Example 44 1-94 4.67 89.4 (0.279, 0.677) 104 Example 45 1-95 4.66 87.2 (0.278, 0.677) 105 Example 46 1-101 4.70 90.7 (0.276, 0.671) 102 Example 47 1-109 4.63 90.9 (0.286, 0.692) 106 Example 48 1-111 4.62 90.1 (0.274, 0.672) 106 Example 49 1-112 4.63 91.3 (0.278, 0.678) 107 Example 50 1-115 4.60 92.2 (0.279, 0.677) 110 Example 51 1-117 4.69 85.4 (0.277, 0.674) 109 Example 52 1-118 4.78 90.2 (0.279, 0.674) 108 Example 53 1-120 4.59 93.1 (0.278, 0.677) 111 Example 54 1-123 4.62 86.2 (0.279, 0.681) 106 Example 55 1-124 4.62 85.2 (0.280, 0.679) 109 Example 56 1-135 4.69 91.2 (0.281, 0.678) 100 Example 57 1-138 4.62 91.7 (0.278, 0.682) 102 Example 58 1-145 4.72 87.2 (0.286, 0.692) 108 Example 59 1-149 4.69 93.2 (0.274, 0.672) 103 Example 60 1-151 4.62 86.2 (0.279, 0.681) 106 Example 61 1-155 4.58 92.3 (0.277, 0.674) 109 Example 62 1-160 4.60 92.4 (0.279, 0.674) 110 Example 63 1-161 4.78 92.6 (0.281, 0.678) 107 Example 64 1-166 4.64 85.4 (0.278, 0.682) 103 Example 65 1-170 4.62 90.2 (0.286, 0.692) 106 Example 66 1-173 4.62 86.4 (0.274, 0.672) 106 Example 67 1-177 4.59 92.5 (0.278, 0.678) 110 Example 68 1-180 4.58 92.3 (0.277, 0.674) 109

As can be seen from the results in Table 9, it was confirmed that the organic light-emitting element using the host material of the present invention had a low driving voltage and significantly improved luminous efficiency and service life compared to the comparative examples. The heterocyclic compound according to the present application has a molecular weight and a band gap suitable for use in a light-emitting layer of an organic light-emitting device while having high thermal stability. A suitable molecular weight is beneficial to the formation of the light-emitting layer of the organic light-emitting device, and a suitable band gap prevents electrons and holes from flowing out of the light-emitting layer, so as to help form an effective recombination zone. In addition, heterocyclic compounds with electron transfer properties substituted at appropriate positions can solve the hole blocking phenomenon caused by dopants to a greater extent than compounds substituted at other positions, and as can be seen from the above device evaluation It can be seen that, compared with the comparative examples, the compounds of the present invention are excellent in all aspects of driving, efficiency and service life. <Experimental example 2> - Manufacture of organic light-emitting device

The glass substrate in which ITO was thinly coated to have a thickness of 1,500 angstroms was ultrasonically cleaned with distilled water. When the wash with distilled water is complete, the glass substrate is ultrasonically washed with solvents such as acetone, methanol, and isopropanol, dried, and then subjected to a 5-minute UVO treatment using UV in a UV cleaning machine . After that, the substrate is transferred to a plasma cleaning machine (PT), and then subjected to plasma treatment under vacuum to achieve ITO work function and remove residual film, and the substrate is transferred to a thermal deposition device for organic deposition.

As a common layer, a hole injection layer 4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA) was formed on the ITO transparent electrode (positive electrode) And the hole transport layer N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPB).

A light-emitting layer was thermally vacuum deposited thereon as described below. Premixing was carried out by premixing one type of heterocyclic compound of Chemical Formula 1 and one type of compound of Chemical Formula 2 as a host as in Table 10 below, and then depositing a luminescent film with a thickness of 360 angstroms from a common container. layer, and a green phosphorescent dopant was deposited by doping the host with Ir(ppy) ₃ in an amount of 7% of the deposited thickness of the emissive layer. After that, BCP was deposited to a thickness of 60 Å as a hole blocking layer, and Alq ₃ was deposited thereon to a thickness of 200 Å as an electron transport layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron transport layer to form an electron injection layer, and then a negative electrode of aluminum (Al) was deposited to a thickness of 1,200 Å on the electron injection layer to form a negative electrode , thereby fabricating organic electroluminescence elements.

Meanwhile, for each material, all organic compounds required for manufacturing OLED elements were subjected to vacuum sublimation purification at 10 ^-6 Torr to 10 ^-8 Torr, and used to manufacture OLEDs. For the organic electroluminescence element manufactured as described above, the electroluminescence (EL) characteristics were measured by M7000 manufactured by Mike Science Corporation, and based on the measurement results, the lifetime was measured by the M7000 manufactured by Mike Science Corporation The measuring equipment (M6000) measured T ₉₀ when the reference luminance was 6,000 cd/m2. Table 10 shows the results of measuring the driving voltage, luminous efficiency, color coordinate (CIE) and service life of the organic light-emitting element manufactured according to the present invention. [Table 10] Light-emitting layer compound Ratio (weight ratio) Driving Voltage (Volts) Efficiency (cd/area) Color coordinates (x, y) Service life (T ₉₀ ) Comparative example 1 A:2-82 1 : 3 4.69 110.0 (0.277, 0.682) 209 Comparative example 2 1 : 2 4.62 111.1 (0.277, 0.678) 203 Comparative example 3 B:2-82 1 : 3 4.67 101.8 (0.276, 0.679) 206 Comparative example 4 1 : 2 4.64 109.2 (0.277, 0.677) 206 Comparative Example 5 C:2-85 1 : 3.5 4.69 103.7 (0.277, 0.680) 209 Comparative example 6 1 : 2.5 4.69 104.8 (0.278, 0.681) 200 Comparative Example 7 1 : 2 4.68 104.8 (0.278, 0.681) 201 Comparative Example 8 D:2-86 1 : 3 4.66 102.3 (0.277, 0.682) 200 Comparative Example 9 1 : 2 4.62 105.2 (0.278, 0.683) 209 Example 1 1-1 : 2-81 1 : 3.5 3.75 176.6 (0.277, 0.678) 310 Example 2 1 : 3 3.70 178.4 (0.277, 0.682) 308 Example 3 1 : 2 3.68 178.8 (0.277, 0.678) 304 Example 4 1 : 1 3.66 179.2 (0.276, 0.679) 303 Example 5 1-2 : 2-82 1 : 3 3.68 172.3 (0.277, 0.677) 307 Example 6 1 : 2 3.60 178.8 (0.277, 0.680) 306 Example 7 1-3 : 2-86 1 : 3 3.66 173.4 (0.278, 0.681) 304 Example 8 1 : 2 3.62 179.6 (0.277, 0.682) 300 Example 9 1-7:2-87 1:2.5 3.66 172.2 (0.278, 0.683) 310 Example 10 1:1 3.60 177.3 (0.277, 0.682) 309 Example 11 1-10:2-83 1:3.5 3.70 171.4 (0.277, 0.678) 310 Example 12 1:2 3.66 173.2 (0.276, 0.679) 306 Example 13 1-15:2-88 1:3 3.71 172.3 (0.277, 0.677) 309 Example 14 1:2 3.68 174.6 (0.277, 0.680) 304 Example 15 1:1 3.64 177.9 (0.278, 0.683) 303 Example 16 1-20:2-80 1:3 3.66 174.3 (0.277, 0.682) 310 Example 17 1 : 2 3.64 176.7 (0.277, 0.678) 306 Example 18 1 : 1 3.60 179.4 (0.276, 0.679) 305 Example 19 1-29:2-87 1 : 3 3.60 186.2 (0.277, 0.677) 310 Example 20 1 : 2 3.59 187.3 (0.277, 0.680) 308 Example 21 1-30:2-88 1 : 3 3.60 182.7 (0.278, 0.681) 307 Example 22 1 : 2 3.59 186.3 (0.278, 0.683) 304 Example 23 1-31:2-87 1 : 3 3.68 176.3 (0.277, 0.682) 288 Example 24 1 : 2 3.66 180.1 (0.277, 0.678) 285 Example 25 1-35 : 2-86 1 : 3 3.48 190.7 (0.281, 0.676) 375 Example 26 1 : 2 3.40 194.4 (0.280, 0.676) 373 Example 27 1-36 : 2-81 1 : 3 3.66 178.2 (0.276, 0.679) 292 Example 28 1 : 2 3.65 176.6 (0.275, 0.679) 290 Example 29 1-40 : 2-85 1 : 3 3.42 194.2 (0.278, 0.678) 377 Example 30 1 : 2 3.39 196.3 (0.279, 0.677) 376 Example 31 1-41 : 2-4 1 : 3 3.98 148.2 (0.275, 0.680) 235 Example 32 1 : 2 3.92 149.7 (0.274, 0.678) 230 Example 33 1-41: 2-27 1 : 3 3.90 148.9 (0.276, 0.676) 250 Example 34 1 : 2 3.85 150.0 (0.274, 0.679) 248 Example 35 1-41 : 2-32 1 : 3 3.91 147.7 (0.288, 0.681) 250 Example 36 1 : 2 3.87 148.9 (0.285, 0.680) 249 Example 37 1-41 : 2-33 1 : 3 3.88 148.8 (0.276, 0.679) 248 Example 38 1 : 2 3.85 149.2 (0.276, 0.676) 246 Example 39 1-41 : 2-42 1 : 3 3.92 152.6 (0.278, 0.681) 210 Example 40 1 : 2.5 3.92 158.4 (0.275, 0.680) 207 Example 41 1:2 3.90 150.3 (0.274, 0.679) 205 Example 42 1:1 3.88 151.1 (0.288, 0.681) 203 Example 43 1-41 : 2-45 1 : 3 3.96 159.4 (0.285, 0.680) 230 Example 44 1 : 2 3.94 151.1 (0.276, 0.679) 226 Example 45 1 : 1.5 3.85 156.3 (0.276, 0.676) 220 Example 46 1 : 1 3.85 157.6 (0.278, 0.681) 200 Example 47 1-41:2-65 1 : 3 3.80 163.7 (0.274, 0.679) 300 Example 48 1 : 2 3.78 165.5 (0.288, 0.681) 296 Example 49 1 : 1.5 3.77 166.7 (0.285, 0.680) 295 Example 50 1 : 1 3.74 168.9 (0.276, 0.679) 290 Example 51 1-41:2-69 1 : 3 3.78 164.2 (0.274, 0.679) 298 Example 52 1 : 2.5 3.76 166.4 (0.288, 0.681) 295 Example 53 1 : 2 3.75 167.9 (0.285, 0.680) 290 Example 54 1-41:2-74 1 : 2 3.79 167.3 (0.276, 0.679) 292 Example 55 1 : 1.5 3.76 169.2 (0.280, 0.676) 290 Example 56 1 : 1 3.75 170.0 (0.276, 0.679) 288 Example 57 1-41 : 2-82 1 : 3.5 3.74 171.1 (0.274, 0.678) 310 Example 58 1 : 2.5 3.72 175.6 (0.276, 0.676) 308 Example 59 1:2 3.63 177.3 (0.274, 0.679) 305 Example 60 1:1 3.60 180.4 (0.288, 0.681) 304 Example 61 1-41 : 2-83 1 : 3 3.62 173.2 (0.280, 0.676) 309 Example 62 1 : 2 3.61 178.3 (0.276, 0.679) 308 Example 63 1-41 : 2-85 1 : 3 3.70 178.3 (0.274, 0.679) 312 Example 64 1 : 2 3.68 180.7 (0.288, 0.681) 309 Example 65 1 : 1 3.65 181.3 (0.285, 0.680) 306 Example 66 1-41 : 2-88 1 : 3 3.69 178.7 (0.275, 0.680) 310 Example 67 1 : 2.5 3.62 180.3 (0.274, 0.679) 309 Example 68 1 : 1 3.61 181.1 (0.274, 0.679) 306 Example 69 1-42:2-83 1 : 3.5 3.75 173.2 (0.277, 0.678) 310 Example 70 1 : 2.5 3.70 178.3 (0.276, 0.679) 309 Example 71 1 : 2 3.66 180.4 (0.277, 0.682) 304 Example 72 1-44:2-85 1 : 3 3.74 171.3 (0.277, 0.678) 308 Example 73 1 : 2 3.70 176.1 (0.276, 0.677) 304 Example 74 1 : 1.5 3.68 179.4 (0.280, 0.679) 303 Example 75 1-45:2-87 1 : 2 3.75 170.6 (0.278, 0.681) 310 Example 76 1 : 1 3.65 179.3 (0.276, 0.679) 309 Example 77 1-46:2-98 1 : 3 3.70 170.4 (0.277, 0.678) 310 Example 78 1 : 2 3.62 177.7 (0.276, 0.677) 305 Example 79 1-47:2-96 1 : 3 3.77 170.6 (0.280, 0.679) 308 instance 80 1 : 2 3.65 174.8 (0.278, 0.681) 306 Example 81 1-49:2-88 1 : 3 3.71 170.3 (0.276, 0.677) 310 Example 82 1 : 2.5 3.68 173.7 (0.280, 0.679) 308 Example 83 1:2 3.65 175.4 (0.278, 0.681) 307 Example 84 1-51:2-89 1 : 3.5 3.68 170.7 (0.277, 0.678) 308 Example 85 1 : 2.5 3.62 172.7. (0.276, 0.677) 305 Example 86 1 : 2 3.60 173.7 (0.280, 0.679) 304 Example 87 1-54:2-80 1 : 3.5 3.73 170.3 (0.276, 0.677) 310 Example 88 1 : 2 3.70 172.6 (0.278, 0.681) 304 Example 89 1 : 1 3.65 175.3 (0.276, 0.679) 302 Example 90 1-55:2-86 1 : 3 3.70 171.1 (0.276, 0.677) 305 Example 91 1 : 2.5 3.64 176.3 (0.280, 0.679) 303 Example 92 1-57:2-88 1 : 3.5 3.71 170.4 (0.277, 0.678) 310 Example 93 1 : 2 3.68 173.1 (0.276, 0.677) 306 Example 94 1 : 1 3.62 174.3 (0.280, 0.679) 303 Example 95 1-69 : 2-82 1 : 3.5 3.60 182.3 (0.276, 0.677) 310 Example 96 1 : 2.5 3.59 188.3 (0.280, 0.679) 309 Example 97 1:2 3.56 190.1 (0.278, 0.681) 308 Example 98 1:1 3.55 190.7 (0.278, 0.681) 303 Example 99 1-71 : 2-82 1 : 3.5 3.70 174.2 (0.276, 0.677) 300 instance 100 1 : 2.5 3.66 177.9 (0.280, 0.679) 299 Example 101 1:2 3.65 179.2 (0.278, 0.681) 294 Example 102 1:1 3.60 180.3 (0.276, 0.677) 290 Example 103 1-75:2-16 1:3 3.62 176.6 (0.280, 0.679) 300 Example 104 1:2 3.60 178.4 (0.276, 0.677) 292 Example 105 1-75:2-33 1:3 3.61 177.9 (0.278, 0.681) 299 Example 106 1:2 3.60 179.9 (0.276, 0.679) 296 Example 107 1-75:2-42 1:3.5 3.61 183.2 (0.276, 0.677) 320 Example 108 1:3 3.56 185.1 (0.280, 0.679) 315 Example 109 1:2 3.55 185.5 (0.277, 0.678) 314 Example 110 1-75:2-66 1:3 3.53 187.3 (0.276, 0.677) 340 Example 111 1:2 3.50 189.2 (0.280, 0.679) 338 Example 112 1-75:2-74 1:3 3.52 188.3 (0.280, 0.679) 339 Example 113 1:2 3.50 190.1 (0.276, 0.677) 336 Example 114 1-75 : 2-82 1 : 3.5 3.47 191.3 (0.277, 0.678) 380 Example 115 1 : 2.5 3.45 194.7 (0.276, 0.677) 378 Example 116 1:2 3.41 199.3 (0.280, 0.679) 377 Example 117 1:1 3.39 200.7 (0.280, 0.679) 370 Example 118 1-77 : 2-82 1 : 3.5 3.60 188.3 (0.274, 0.679) 311 Example 119 1 : 2.5 3.59 189.7 (0.288, 0.681) 308 Example 120 1:2 3.57 190.3 (0.285, 0.680) 307 Example 121 1:1 3.55 192.3 (0.285, 0.680) 304 Example 122 1-80 : 2-82 1 : 3.5 3.50 194.4 (0.276, 0.677) 380 Example 123 1 : 3 3.48 197.2 (0.278, 0.681) 374 Example 124 1 : 2.5 3.45 198.3 (0.276, 0.679) 370 Example 125 1:2 3.40 199.0 (0.274, 0.679) 369 Example 126 1:1 3.30 199.8 (0.288, 0.681) 368 Example 127 1-81:2-81 1 : 3 3.66 178.3 (0.277, 0.678) 310 Example 128 1 : 2 3.64 180.2 (0.276, 0.677) 308 Example 129 1-86:2-84 1:2.5 3.63 177.6 (0.280, 0.679) 309 Example 130 1 : 2 3.62 178.2 (0.280, 0.679) 308 Example 131 1 : 1 3.60 179.3 (0.274, 0.679) 307 Example 132 1-90:2-82 1:3 3.70 176.3 (0.288, 0.681) 310 Example 133 1:2.5 3.66 178.9 (0.285, 0.680) 309 Example 134 1:1 3.62 180.2 (0.285, 0.680) 308 Example 135 1-94:2-81 1 : 3 3.68 176.3 (0.277, 0.678) 309 Example 136 1 : 2 3.64 177.7 (0.276, 0.677) 304 Example 137 1-95:2-83 1:2.5 3.69 177.7 (0.280, 0.679) 309 Example 138 1 : 2 3.64 179.3 (0.280, 0.679) 308 Example 139 1 : 1 3.60 180.4 (0.274, 0.679) 306 Example 140 1-101:2-84 1 : 3 3.62 174.5 (0.288, 0.681) 309 Example 141 1 : 2 3.60 177.7 (0.285, 0.680) 304 Example 142 1-109:2-81 1 : 3 3.58 188.7 (0.285, 0.680) 310 Example 143 1 : 2 3.56 190.2 (0.277, 0.678) 309 Example 144 1-115:2-83 1 : 3 3.42 194.9 (0.276, 0.677) 380 Example 145 1 : 2 3.40 199.2 (0.280, 0.679) 377 Example 146 1-120:2-91 1 : 3 3.40 196.3 (0.280, 0.679) 379 Example 147 1 : 2 3.32 199.4 (0.274, 0.679) 377 Example 148 1-124:2-97 1 : 3 3.70 178.4 (0.288, 0.681) 310 Example 149 1 : 2 3.68 179.9 (0.285, 0.680) 308 Instance 150 1-138:2-91 1:3 3.68 176.4 (0.285, 0.680) 309 Example 151 1 : 2.5 3.62 177.2 (0.277, 0.678) 307 Example 152 1 : 2 3.60 179.5 (0.276, 0.677) 306 Example 153 1-145:2-91 1:3 3.64 178.4 (0.280, 0.679) 308 Example 154 1 : 2.5 3.62 179.0 (0.280, 0.679) 307 Example 155 1 : 2 3.60 170.1 (0.274, 0.679) 306 Example 156 1-149:2-88 1 : 3 3.60 181.4 (0.288, 0.681) 310 Example 157 1 : 2 3.59 188.7 (0.285, 0.680) 308 Example 158 1-153:2-97 1 : 3 3.64 179.2 (0.285, 0.680) 304 Example 159 1 : 2 3.62 180.8 (0.277, 0.678) 300 Instance 160 1-166:2-82 1 : 3 3.70 178.4 (0.276, 0.677) 310 Example 161 1 : 2 3.68 179.5 (0.280, 0.679) 308 Example 162 1-176:2-88 1 : 3 3.40 192.9 (0.280, 0.679) 380 Example 163 1 : 2 3.38 199.4 (0.274, 0.679) 378 Instance 164 1-180:2-85 1 : 3 3.38 197.4 (0.288, 0.681) 379 Example 165 1 : 2 3.34 199.6 (0.285, 0.680) 375 Example 166 1-162:2-4 1 : 3 3.62 174.5 (0.288, 0.681) 309 Example 167 1 : 2 3.60 177.7 (0.285, 0.680) 304 Example 168 1-162:2-27 1:3 3.70 176.3 (0.288, 0.681) 300 Example 169 1:2.5 3.66 178.9 (0.285, 0.680) 299 Instance 170 1:1 3.62 180.2 (0.285, 0.680) 298 Example 171 1-163:2-27 1 : 3 3.66 178.3 (0.277, 0.678) 310 Example 172 1 : 2 3.64 179.2 (0.276, 0.677) 309 Example 173 1-169:2-33 1 : 3 3.80 163.7 (0.274, 0.679) 300 Example 174 1 : 2 3.78 165.5 (0.288, 0.681) 296 Example 175 1-169:2-40 1 : 3 3.62 174.5 (0.288, 0.681) 300 Example 176 1 : 2 3.60 177.7 (0.285, 0.680) 292 Example 177 1-169:2-38 1 : 2.5 3.66 177.9 (0.280, 0.679) 299 Example 178 1:2 3.65 179.2 (0.278, 0.681) 294 Example 179 1-170:2-6 1 : 3 3.60 181.4 (0.288, 0.681) 310 Instance 180 1 : 2 3.59 188.7 (0.285, 0.680) 308 Example 181 1-170:2-27 1 : 3 3.62 182.5 (0.288, 0.681) 303 Example 182 1 : 2 3.60 180.7 (0.285, 0.680) 300 Example 183 1-170:2-32 1 : 3 3.48 180.7 (0.281, 0.676) 300 Example 184 1 : 2 3.40 179.4 (0.280, 0.676) 299 Example 185 1-175:2-20 1 : 3 3.66 178.2 (0.276, 0.679) 301 Example 186 1 : 2 3.65 176.6 (0.275, 0.679) 200 Example 187 1-175:2-24 1 : 3 3.42 174.2 (0.278, 0.678) 307 Example 188 1 : 2 3.39 176.3 (0.279, 0.677) 306 Example 189 1-179:2-40 1 : 3 3.98 180.2 (0.275, 0.680) 305 Example 190 1 : 2 3.92 179.7 (0.274, 0.678) 300

As can be seen from the results in Table 10, it was confirmed that when the heterocyclic compound of the present invention was used as an N-type host and mixed with a P-type host and deposited, the driving, efficiency, and service life of the organic light emitting element were improved. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as the host of the light-emitting layer, due to the excited complex phenomenon of the N+P compound, the Holes are injected into the p-body and cause electrons to be injected into the n-body, thus adjusting the charge balance within the element. Therefore, it can be seen that the combination of an N-type host compound having a suitable electron transfer property and a P-type host compound having a suitable hole transfer property in an appropriate ratio helps to improve driving efficiency and service life.

100: Substrate 200: positive electrode 300: organic material layer 301: Hole injection layer 302: Hole transport layer 303: luminous layer 304: Hole blocking layer 305: electron transport layer 306: Electron injection layer 400: negative electrode

1 to 3 are each a diagram schematically illustrating a stacked structure of an organic light emitting element according to an exemplary embodiment of the present application.

100: Substrate

200: positive electrode

300: organic material layer

400: negative electrode

Claims (15)

A heterocyclic compound represented by the following Chemical Formula 1: [Chemical Formula 1] Wherein, in Chemical Formula 1, X is O or S, Ar1 and Ar2 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted Substituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl -P(=O)RR';-SiRR'R''; and substituted or unsubstituted amino groups, R1 to R8 are the same or different from each other, and are each independently selected from the group consisting of hydrogen ; deuterium; halo; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR';-SiRR'R''; and substituted or unsubstituted amino, and R1 to R6 At least one of is a substituted or unsubstituted C6 to C60 aryl group, a is an integer of 0 to 2, b and c are integers of 0 to 4, when a is an integer of 2 or b and c are When it is an integer of 2 or higher than 2, the substituents in the brackets are the same or different from each other, m is an integer of 0 or 1, when m is an integer of 1, R5 and R6 are hydrogen or deuterium, when m is When an integer of 0, at least one of Ar1 and Ar2 is represented by the following chemical formula 1-1, [chemical formula 1-1] In Chemical Formula 1-1, X1 is O or S, R11 to R15 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted Substituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl -P(=O)RR';-SiRR'R''; and a substituted or unsubstituted amino group, and at least one of R11 to R15 is a substituted or unsubstituted C6 to C60 aromatic R, R' and R'' are the same or different from each other, and are independently substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or Unsubstituted C2 to C60 heteroaryl, and a1 is an integer of 0 to 3, and when a is an integer of 2 or higher, the substituents in parentheses are the same or different from each other. The heterocyclic compound as described in claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formula 3 to Chemical Formula 5: [Chemical Formula 3] [chemical formula 4] [chemical formula 5] In Chemical Formula 3 to Chemical Formula 5, the definition of each substituent is the same as that in Chemical Formula 1. The heterocyclic compound as claimed in claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formula 6 to Chemical Formula 8: [Chemical Formula 6] [chemical formula 7] [chemical formula 8] In Chemical Formula 6 to Chemical Formula 8, the definition of each substituent is the same as that in Chemical Formula 1. The heterocyclic compound as claimed in claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formula 9 to Chemical Formula 11: [Chemical Formula 9] [chemical formula 10] [chemical formula 11] In Chemical Formula 9 to Chemical Formula 11, the definitions of R1 to R8, R11 to R15, a, b, c, a1, X and X1 are the same as those in Chemical Formula 1, and Ar11 and Ar12 are the same or different from each other, and each independently is a substituted or unsubstituted C6 to C60 aryl group. The heterocyclic compound as described in Claim 1, wherein Chemical Formula 1 is represented by the following Structural Formula A to Structural Formula D, and the deuterium content of the following Structural Formula A to Structural Formula D is 0% to 100%: [Structural Formula A] [Structural formula B] [Structural formula C] [Structural formula D] In structural formula A to structural formula D, the bonding position means a position to which each substituent is bonded, and the same symbols are bonded to each other, and the definition of each substituent is the same as that in Chemical Formula 1. The heterocyclic compound as claimed in item 1, wherein chemical formula 1 is represented by any one of the following compounds: . An organic light emitting element, comprising: first electrode; a second electrode disposed facing said first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, Wherein one or more layers of the organic material layer comprise the heterocyclic compound as described in any one of claims 1 to 6. The organic light-emitting device according to claim 7, wherein the organic material layer comprising the heterocyclic compound further comprises a heterocyclic compound represented by the following chemical formula 2: [chemical formula 2] In Chemical Formula 2, Ra1 to Ra14 are the same or different from each other, and are each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted Substituted C2 to C60 heterocycloalkyl; Substituted or unsubstituted C6 to C60 aryl; Substituted or unsubstituted C2 to C60 heteroaryl; SiRaRa'Ra''; or -P(=O) RaRa', La1 and La2 are the same or different from each other, and each is independently a direct bond; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, Ara1 and Ara2 are the same or different from each other, and are each independently -CN; SiRaRa'Ra''; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted Or unsubstituted C2 to C60 heteroaryl, and Ra, Ra' and Ra'' are the same or different from each other, and each independently is a substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl. The organic light-emitting element as claimed in item 8, wherein Chemical Formula 2 is represented by a bond of the following Structural Formula A-1 to the following Structural Formula C-1, and the deuterium content of the following Structural Formula A-1 to the following Structural Formula C-1 0% to 100%: [Structural formula A-1] [Structural formula B-1] [Structural formula C-1] In structural formula A-1 to structural formula C-1, the bonding position means a position to which each substituent is bonded, and the same symbols are bonded to each other, and the definition of each substituent is the same as that in Chemical Formula 2. The organic light-emitting element as claimed in item 8, wherein the heterocyclic compound represented by Chemical Formula 2 is represented by any one of the following compounds: . The organic light-emitting device according to claim 7, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound. The organic light-emitting device according to claim 7, wherein the organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes the heterocyclic compound. The organic light-emitting device according to claim 7, further comprising one selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. layer or two or more layers. An organic light-emitting element organic material layer composition, the composition comprising the heterocyclic compound as described in any one of claims 1 to 6 and the heterocyclic compound represented by the following chemical formula 2: [chemical formula 2] In Chemical Formula 2, Ra1 to Ra14 are the same or different from each other, and are each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted Substituted C2 to C60 heterocycloalkyl; Substituted or unsubstituted C6 to C60 aryl; Substituted or unsubstituted C2 to C60 heteroaryl; SiRaRa'Ra''; or -P(=O) RaRa', La1 and La2 are the same or different from each other, and each is independently a direct bond; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, Ara1 and Ara2 are the same or different from each other, and are each independently -CN; SiRaRa'Ra''; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted Or unsubstituted C2 to C60 heteroaryl, and Ra, Ra' and Ra'' are the same or different from each other, and each independently is a substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl. The composition according to claim 14, wherein the weight ratio of the heterocyclic compound: the heterocyclic compound represented by Chemical Formula 2 in the composition is 1:10 to 10:1.