TW202328136A - Heterocyclic compound, organic light emitting device comprising the same and composition for organic material layer of organic light emitting device - Google Patents

Abstract

The present disclosure relates to a heterocyclic compound represented by Chemical Formula 1, an organic light emitting device comprising the same, and a composition for an organic material layer of an organic light emitting device.

Description

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

The disclosure relates to a heterocyclic compound, an organic light emitting device (organic light emitting device, OLED) including the heterocyclic compound, and a composition for an organic material layer.

This application claims priority and rights to Korean Patent Application No. 10-2021-0121280 filed with the Korea Intellectual Property Office on September 10, 2021, the entire content of which is incorporated herein by reference.

The organic light-emitting device is a self-emissive display device, and has the advantages of wide viewing angle, high response speed and excellent contrast.

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 such a structure, electrons and holes injected from the two electrodes are combined into pairs in the organic thin film, and light is emitted when the electrons and holes are annihilated. The organic thin film can be formed in a single layer or in multiple layers as needed.

The material of the organic thin film may have a light emitting function as required. For example, as the material of the organic thin film, compounds each capable of forming a light-emitting layer by itself, or compounds each capable of functioning as a host or a dopant of a light-emitting layer based on a host-dopant may be used. In addition, compounds capable of performing functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and the like can also be used as materials for organic thin films.

In order to enhance the potency, lifetime or efficiency of organic light-emitting devices, there is a continuing need to develop organic thin film materials. [Prior Technical Document] [Patent Document] (Patent Document 1) US Patent No. 4,356,429

[technical problem]

The purpose of the present disclosure is to provide a heterocyclic compound, an organic light-emitting device including the heterocyclic compound, and a composition for an organic material layer. [Technical solution]

In order to achieve the above objects, the present disclosure provides a heterocyclic compound represented by the following Chemical Formula 1. [chemical formula 1]

In Chemical Formula 1, R1 to R10 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; 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)R101R102 ; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 Heterocyclic ring, wherein R101, R102 and R103 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 Substituted C2 to C60 heteroaryl, R11 is the following chemical formula 2, [chemical formula 2] In Chemical Formula 2, L1 is a direct bond; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, m is an integer of 0 to 5, and when When m is 2 or greater than 2, L1 are the same or different from each other, and N-Het is a C2 to C60 monocyclic or polycyclic heterocyclic group that is substituted or unsubstituted and includes two or more Ns, and * is a link to the point of the following chemical formula 3, [chemical formula 3] X1 is NRa; O; S; CRbRc; or a direct bond, and Ra, Rb, Rc, and R21 to R24 are the same or different from each other, and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; 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 alkane Oxygen; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted -P(=O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 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 addition, the present disclosure provides an organic light-emitting device, including: first electrode; a second electrode disposed opposite the first electrode; and one or more organic material layers, disposed between the first electrode and the second electrode, wherein at least one of the one or more layers of the organic material layer includes a heterocyclic compound represented by Chemical Formula 1.

In addition, the present disclosure provides an organic light-emitting device, wherein the organic material layer further includes a heterocyclic compound represented by the following Chemical Formula 5. [chemical formula 5]

In Chemical Formula 5, R61 to R70 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; 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)R101R102 ; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 Heterocyclic ring, wherein R101, R102 and R103 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 A substituted C2 to C60 heteroaryl, R71 is a substituted or unsubstituted C6 to C60 aryl; a substituted or unsubstituted C2 to C60 heteroaryl; or the following chemical formula 6, when the heteroaryl of the heteroaryl When the atom is N, including a heteroatom, [Chemical Formula 6] In chemical formula 6, L2 is a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl, n is an integer from 1 to 5, and when n is 2 or greater than 2, L2 is the same or different from each other, and Ar1 and Ar2 are the same or different from each other, and are each independently substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 hetero Aryl, and * is the point of attachment to the following chemical formula 7, [chemical formula 7] X2 is NRe; O; S; CRfRg; or a direct bond, and Re, Rf, Rg, and R81 to R84 are the same or different from each other, and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; 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 alkane Oxygen; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted -P(=O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 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.

In addition, the present disclosure provides a composition for an organic material layer of an organic light emitting device, the composition including the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5. [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 play the role of hole injection layer material, electron blocking layer material, hole transport layer material, light emitting layer material, electron transport layer material, hole blocking layer material, electron injection layer material and similar materials in organic light-emitting elements. effect. Specifically, the compound can be used as a light-emitting layer material of an organic light-emitting element.

Specifically, the compound can be used alone as a light-emitting material or as a mixture with a P-type host, and can be used as a host material or a dopant material of a light-emitting layer. Using the compound represented by Chemical Formula 1 in the organic material layer can reduce driving voltage, enhance luminous efficiency, and enhance lifetime properties in an organic light emitting element.

More specifically, the heterocyclic compound represented by Chemical Formula 1 of the present disclosure can improve hole injection and Hole transport properties, and thus can reduce the driving voltage and enhance luminous efficiency and life properties.

Hereinafter, the present disclosure will be explained in more detail.

In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of substitution is not limited as long as it is a position where a hydrogen atom is substituted (also 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 selected from deuterium, halogen, cyano, C1 to C60 straight or branched chain alkyl, C2 to C60 straight or branched chain alkenyl, C2 to C60 straight chain or branched chain 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 alkylamine, C6 to C60 monocyclic or polycyclic arylamine and C2 to C60 monocyclic or One or more substituents of the group consisting of polycyclic heteroarylamine groups are substituted or unsubstituted, or a substituent in which two or more substituents selected from the above-exemplified substituents are linked Substituted or not.

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

In the present specification, the alkyl group includes linear or branched chain alkyl groups having 1 to 60 carbon atoms, and may be further substituted with other substituents. 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 may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, second-butyl, 1-methyl- Butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-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 propyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like, but not limited thereto.

In the present specification, the alkenyl group includes linear or branched alkenyl groups having 2 to 60 carbon atoms, and may be further substituted with other substituents. 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 may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl , 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-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, stilbenyl (stilbenyl group), styryl and the like, but not limited thereto.

In the present specification, the alkynyl group includes linear or branched alkynyl groups having 2 to 60 carbon atoms, and may be further substituted with other substituents. 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 alkoxy may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy Oxygen, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy , benzyloxy, p-methylbenzyloxy and similar groups, but not limited thereto.

In the present specification, cycloalkyl includes monocyclic or polycyclic rings having 3 to 60 carbon atoms, and may be further substituted with other substituents. Herein, polycyclic means a group in which a cycloalkyl group is directly linked or fused to another cyclic group. Herein, the other cyclic groups may be cycloalkyl groups, but may also be different types of cyclic groups, such as heterocycloalkyl groups, aryl groups and heteroaryl groups. 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 may 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 further substituted with other substituents. Herein, polycyclic means a group in which a heterocycloalkyl group is directly bonded or fused to another cyclic group. Herein, the other cyclic groups may be heterocycloalkyl groups, but may also be different types of cyclic groups, such as cycloalkyl groups, aryl groups and heteroaryl groups. 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 monocyclic or polycyclic rings having 6 to 60 carbon atoms, and may be further substituted with other substituents. Herein, polycyclic means a group in which an aryl group is directly linked or fused to another cyclic group. Herein, the other cyclic groups may be aryl groups, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl and heteroaryl. Aryl groups may include spirocyclic groups. 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 may include phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, phenanthryl, phenanthrenyl, perylenyl, fluoranthracenyl, biterphenylenyl, phenanthryl, pyrenyl, fused Tetraphenyl, 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, wherein R101 and R102 are the same or different from each other, and each independently may be a substituent formed by 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 as the aryl group, the above-mentioned examples may be applied. Examples of the phosphine oxide group may include diphenylphosphine oxide group, dinaphthyl phosphine oxide group, and the like, but are not limited thereto.

In this specification, a silyl group is a substituent containing Si and having a Si atom directly linked as a radical, and is represented by -SiR101R102R103. R101 to R103 are the same or different from each other, and may each independently be a substituent formed by at least one of the following: hydrogen; deuterium; halo; alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and heterocyclyl. Specific examples of silyl groups may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl , diphenylsilyl, phenylsilyl and similar groups, 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 fluorenyl is substituted, may include , , , , , and similar groups, however, the structure 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 further substituted with other substituents. Herein, polycyclic means a group in which a heteroaryl group is directly linked or fused to another cyclic group. Herein, other cyclic groups may be heteroaryl groups, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl and aryl. 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 may include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, Triazolyl, furanyl, oxadiazolyl, thiadiazolyl, bithiazolyl, tetrazolyl, pyryl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl ( dioxynyl group), triazine, tetrazine, quinolinyl, isoquinolinyl, quinazolinyl group, isoquinazolinyl, quinazolinyl group, naphthyridinyl, acridine Pyridyl, phenanthridinyl (phenanthridinyl group), imidazopyridyl, naphthyl, triazindenyl, 2-indolyl, indolizyl, benzothiazolyl, benzoxazolyl, Benzimidazolyl, benzothienyl, benzofuryl, dibenzothienyl, dibenzofuryl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenhydrazinyl, diphenyl Dibenzosilole group, spirobis(dibenzosilole group), dihydrophenanthrazinyl, phenanthrazinyl, phenanthridyl group, thienyl (thienyl group), indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, indolinyl, 10,11-dihydro-dibenzo[ b,f]Azinyl, 9,10-dihydroacridinyl, phenanthazinyl, phenanthiazinyl, phthalazinyl, naphthyridinyl, phenanthrolinyl, 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]carba Azolyl and the like, but not limited thereto.

In this specification, the amine group can be selected from the group consisting of: monoalkylamine group; monoarylamine group; monoheteroarylamine group; -NH ₂ ; ; diheteroarylamine group; alkylarylamine group; alkylheteroarylamine group; and arylheteroarylamine group, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 30 . Specific examples of the amine group may include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, biphenylamine Base, anthracenylamine, 9-methyl-anthrylamine, diphenylamine, phenylnaphthylamine, xylylamine, phenylcresylamine, triphenylamine, biphenyl Phenylnaphthylamino, phenylbiphenylylamino, biphenylfluorenylamino, phenylbisphenylylamino, biphenylbiphenylylamino and similar groups, but not limited to this.

In this specification, an aryl group means an aryl group having two bonding sites, ie, a divalent group. The descriptions provided above for aryl groups can be applied to the arylene groups except that each of the arylene groups is a divalent group. In addition, the heteroaryl group means a heteroaryl group having two bonding sites, that is, a divalent group. The remarks provided above for heteroaryl groups can be applied to heteroaryl groups except that each of the heteroaryl groups is a divalent group.

In this specification, an "adjacent" group may mean a substituent that replaces an atom directly bonded to an atom substituted by the corresponding substituent, a substituent that is spatially closest to the corresponding substituent, or a substituent that replaces the corresponding substituent. Another substituent for the substituted atom. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be construed as being "adjacent" to each other.

In the present disclosure, "the case where no substituent is specified in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium ( ² H) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

In one embodiment of the present disclosure, "the case where no substituent is specified in the chemical formula or compound structure" may mean that the positions that can be used as substituents are all hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms may be deuterium as an isotope, and herein, the content of deuterium may be 0% to 100%.

In one embodiment of the present disclosure, in "the situation where no substituent is specified in the chemical formula or compound structure", when deuterium is not explicitly excluded (for example, "the deuterium content is 0%", "the hydrogen content is 100%" or "The substituents are all hydrogen"), hydrogen and deuterium can be used interchangeably in the compound.

In one embodiment of the present disclosure, deuterium is one of the isotopes of hydrogen, an element having a deuteron formed from one proton and one neutron as a nucleus, and can be expressed as hydrogen-2, and its element symbol It can also be written as D or ² H.

In one embodiment of the present disclosure, isotopes refer to atoms with the same atomic number (Z) but different mass numbers (A), and can also be interpreted as elements with the same number of protons but different numbers of neutrons.

In one embodiment of the present disclosure, when the total number of substituents that the base compound may have is defined as T1, and the number of specific substituents among these substituents is defined as T2, the content of the specific substituent T% The meaning of can be defined as T2/T1×100=T%.

In other words, in one example, after the The indicated phenyl having a deuterium content of 20% 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 among these substituents is 1 (T2 in the formula) . In other words, having a deuterium content of 20% in the phenyl group can be represented by the following structural formula.

In addition, in an embodiment of the present disclosure, "phenyl with 0% deuterium content" may refer to a phenyl group without deuterium atoms, that is, a phenyl group with 5 hydrogen atoms.

In the present disclosure, a C6 to C60 aromatic hydrocarbon ring means a compound including an aromatic ring formed of C6 to C60 carbons and hydrogen. Examples of C6 to C60 aromatic hydrocarbon rings may include phenyl, biphenyl, terphenyl, biterphenyl, naphthalene, anthracene, anthracene, phenanthrene, fluorene, pyrene, perylene, perylene, azulene, and similar compounds, but are not limited thereto , and includes all aromatic hydrocarbon ring compounds known in the art and satisfying the above-mentioned number of carbon atoms.

The present disclosure provides a heterocyclic compound represented by Chemical Formula 1 below. [chemical formula 1]

In Chemical Formula 1, R1 to R10 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; 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)R101R102 ; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 Heterocyclic ring, wherein R101, R102 and R103 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 Substituted C2 to C60 heteroaryl, R11 is the following chemical formula 2, [chemical formula 2] In Chemical Formula 2, L1 is a direct bond; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, m is an integer of 0 to 5, and when When m is 2 or greater than 2, L1 are the same or different from each other, and N-Het is a C2 to C60 monocyclic or polycyclic heterocyclic group that is substituted or unsubstituted and includes two or more Ns, and * is a link to the point of the following chemical formula 3, [chemical formula 3] X1 is NRa; O; S; CRbRc; or a direct bond, and Ra, Rb, Rc, and R21 to R24 are the same or different from each other, and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; 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 alkane Oxygen; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted -P(=O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 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 one embodiment of the present disclosure, R1 to R10 are the same or different from each other, and are independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C2 to C30 alkenyl; substituted or unsubstituted C2 to C30 alkynyl; substituted or unsubstituted C1 to C30 alkoxy; substituted or unsubstituted C3 to C30 cycloalkyl; substituted or unsubstituted C2 to C30 heterocycloalkyl; substituted or unsubstituted C6 to C30 aryl; substituted or unsubstituted C2 to C30 heteroaryl; -P(=O)R101R102; -SiR101R102R103 ; or -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocyclic ring , and R101, R102, and R103 are the same or different from each other, and can be independently substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted Substituted C2 to C30 heteroaryl.

In another embodiment of the present disclosure, R1 to R10 are the same or different from each other, and are independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted Substituted C2 to C20 alkenyl; substituted or unsubstituted C2 to C20 alkynyl; substituted or unsubstituted C1 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; Substituted or unsubstituted C2 to C20 heterocycloalkyl; Substituted or unsubstituted C6 to C20 aryl; Substituted or unsubstituted C2 to C20 heteroaryl; -P(=O)R101R102;- SiR101R102R103; or -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 hetero Ring, wherein R101, R102 and R103 are the same or different from each other, and each independently can be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted Substituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, R1 to R10 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, R1 to R10 are the same or different from each other, and each independently can be hydrogen; or deuterium.

In one embodiment of the present disclosure, L1 may be a direct bond; a substituted or unsubstituted C6-C30 arylylene group; or a substituted or unsubstituted C2-C30 heteroarylylene group.

In another embodiment of the present disclosure, L1 may be a direct bond; a substituted or unsubstituted C6-C20 arylylene group; or a substituted or unsubstituted C2-C20 heteroarylylene group.

In another embodiment of the present disclosure, L1 may be a direct bond; an unsubstituted or deuterium-substituted C6-C20 arylylene group; or an unsubstituted or deuterium-substituted C2-C20 heteroarylyl group.

In one embodiment of the present disclosure, N-Het may be a substituted or unsubstituted C2 to C30 monocyclic or polycyclic heterocyclic group including two or more Ns.

In one embodiment of the present disclosure, N-Het may be a substituted or unsubstituted C2 to C20 monocyclic or polycyclic heterocyclic group including two or more Ns.

In another embodiment of the present disclosure, N-Het may be a C2 to C20 monocyclic or polycyclic heterocyclic group that is unsubstituted or substituted with deuterium and includes two or more Ns.

In one embodiment of the present disclosure, when N-Het has a substituent, the substituent can be deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

In another embodiment of the present disclosure, when N-Het has a substituent, the substituent can be deuterium; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 aryl group; C30 heteroaryl.

In another embodiment of the present disclosure, when N-Het has a substituent, the substituent can be deuterium; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, when N-Het has a substituent, the substituent can be deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted dibenzofuryl; substituted or unsubstituted dibenzothienyl; substituted or unsubstituted naphthobenzofuryl; substituted or unsubstituted carbazolyl; substituted or unsubstituted naphthobenzothienyl; or substituted or unsubstituted benzocarbazolyl.

In one embodiment of the present disclosure, Ra, Rb, Rc, and R21 to R24 are the same or different from each other, and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C30 alkyl; Substituted or unsubstituted C2 to C30 alkenyl; substituted or unsubstituted C2 to C30 alkynyl; substituted or unsubstituted C1 to C30 alkoxy; substituted or unsubstituted C3 to C30 Cycloalkyl; substituted or unsubstituted C2 to C30 heterocycloalkyl; substituted or unsubstituted C6 to C30 aryl; substituted or unsubstituted C2 to C30 heteroaryl; -P(= O) R101R102; -SiR101R102R103; or -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or substituted or unsubstituted C2 to C30 heterocyclic ring, wherein R101, R102 and R103 are the same or different from each other, and can be independently substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2 to C30 heteroaryl.

In another embodiment of the present disclosure, Ra, Rb, Rc, and R21 to R24 are the same or different from each other, and each is independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl ; substituted or unsubstituted C2 to C20 alkenyl; substituted or unsubstituted C2 to C20 alkynyl; substituted or unsubstituted C1 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 heterocycloalkyl; substituted or unsubstituted C6 to C20 aryl; substituted or unsubstituted C2 to C20 heteroaryl; -P( =O) R101R102; -SiR101R102R103; or -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or substituted or unsubstituted Substituted C2 to C20 heterocyclic ring, wherein R101, R102 and R103 are the same or different from each other, and can each be independently substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl ; or a substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, Ra, Rb, Rc, and R21 to R24 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, Ra may be substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; or substituted or unsubstituted terphenyl.

In another embodiment of the present disclosure, Rb and Rc are the same or different from each other, and each independently can be a substituted or unsubstituted C1-C20 alkyl group.

In another embodiment of the present disclosure, Rb and Rc are the same or different from each other, and can each be independently substituted or unsubstituted methyl.

In another embodiment of the present disclosure, R21 to R24 are the same or different from each other, and each independently can be hydrogen; or deuterium.

In one embodiment of the present disclosure, the compound represented by Chemical Formula 1 may not contain deuterium as a substituent, or may have greater than 0%, 1%, or greater than 1%, 10%, or Greater than 10%, 20% or greater than 20%, 30% or greater than 30%, 40% or greater than 40%, or 50% or greater than 50% and 100% or less than 100%, 90% or less than 90%, 80% or A deuterium content of less than 80%, 70% or less, or 60% or less.

In another embodiment of the present disclosure, the compound represented by Chemical Formula 1 may not contain deuterium as a substituent, or may have a deuterium content of 1% to 100% based on the sum of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, the compound represented by Chemical Formula 1 may not contain deuterium as a substituent, or may have a deuterium content of 20% to 90% based on the sum of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, the compound represented by Chemical Formula 1 may not contain deuterium as a substituent, or may have a deuterium content of 30% to 80% based on the sum of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, the compound represented by Chemical Formula 1 may not contain deuterium as a substituent, or may have a deuterium content of 50% to 70% based on the sum of hydrogen atoms and deuterium atoms.

In one embodiment of the present disclosure, Chemical Formula 1 may be a heterocyclic compound represented by any one of the following Chemical Formula 1-1 and Chemical Formula 1-2. [chemical formula 1-1] [chemical formula 1-2]

In Chemical Formula 1-1 and Chemical Formula 1-2, R1 to R10 have the same definitions as in Chemical Formula 1, R11 has the same definition as in chemical formula 2, and X1 and R21 to R24 have the same definitions as in Chemical Formula 3.

In one embodiment of the present disclosure, Chemical Formula 2 may be represented by Chemical Formula 4 below. [chemical formula 4]

In chemical formula 4, X11 to X15 are the same or different from each other, and are each independently N; or CRd, At least two or more of X11 to X15 are N, When there are two or more CRd, Rd are the same or different from each other, Rd is selected from the group consisting of: hydrogen; deuterium; halogen; 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)R101R102; -SiR101R102R103; and -NR101R102, or two or more adjacent to each other A plurality of groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 are the same or different from each other, and each 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 L1 and m have the same definitions as in Chemical Formula 2.

In one embodiment of the present disclosure, Rd is hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C2 to C30 alkenyl; substituted or unsubstituted Substituted C2 to C30 alkynyl; substituted or unsubstituted C1 to C30 alkoxy; substituted or unsubstituted C3 to C30 cycloalkyl; substituted or unsubstituted C2 to C30 heterocycloalkane substituted or unsubstituted C6 to C30 aryl; substituted or unsubstituted C2 to C30 heteroaryl; -P(=O)R101R102; -SiR101R102R103; or -NR101R102, or two adjacent to each other or more groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocyclic ring, wherein R101, R102 and R103 are the same or different from each other, and each independently may be a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

In another embodiment of the present disclosure, Rd is hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C2 to C20 alkenyl; Unsubstituted C2 to C20 alkynyl; substituted or unsubstituted C1 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 heterocycle Alkyl; substituted or unsubstituted C6 to C20 aryl; substituted or unsubstituted C2 to C20 heteroaryl; -P(=O)R101R102; -SiR101R102R103; or -NR101R102, or adjacent to each other Two or more groups are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocyclic ring, wherein R101, R102 and R103 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 a substituted or unsubstituted C2 to C20 heteroaryl group.

In another embodiment of the present disclosure, Rd is hydrogen; deuterium; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl, or two adjacent to each other One or more groups may be bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocyclic ring.

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

In Chemical Formula 4-1 to Chemical Formula 4-4, R31 to R43 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; 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 Substituted C2 to C60 heterocycloalkyl; Substituted or unsubstituted C6 to C60 aryl; Substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)R101R102; -SiR101R102R103; -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101 , R102 and R103 are the same or different from each other, and each independently is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 aryl group; C60 heteroaryl, and L1 and m have the same definitions as in Chemical Formula 2.

In one embodiment of the present disclosure, R31 and R32 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

In another embodiment of the present disclosure, R31 and R32 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C6-C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

In another embodiment of the present disclosure, R31 and R32 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C6-C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, R31 and R32 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; Substituted or unsubstituted naphthyl; Substituted or unsubstituted dibenzofuryl; Substituted or unsubstituted dibenzothienyl; Substituted or unsubstituted naphthobenzofuryl; substituted or unsubstituted carbazolyl; or substituted or unsubstituted naphthobenzothienyl.

In one embodiment of the present disclosure, R33 to R35 are the same or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 A heteroaryl group, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring.

In another embodiment of the present disclosure, R33 to R35 are the same or different from each other, and are independently hydrogen; deuterium; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocyclic ring .

In another embodiment of the present disclosure, R33 to R35 are the same or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocyclic ring .

In another embodiment of the present disclosure, R33 to R35 are the same or different from each other, and are independently hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; Substituted or unsubstituted naphthyl, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocycles.

In one embodiment of the present disclosure, R36 to R40 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

In another embodiment of the present disclosure, R36 to R40 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

In another embodiment of the present disclosure, R36 to R40 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, R36 to R40 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; Substituted or unsubstituted naphthyl; Substituted or unsubstituted carbazolyl; Substituted or unsubstituted dibenzofuryl; Substituted or unsubstituted naphthobenzofuryl; Substituted or unsubstituted naphthobenzothienyl; or substituted or unsubstituted benzocarbazolyl.

In one embodiment of the present disclosure, R41 to R43 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

In another embodiment of the present disclosure, R41 to R43 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

In another embodiment of the present disclosure, R41 to R43 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, R41 to R43 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted phenyl; or substituted or unsubstituted biphenyl.

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

In Chemical Formula 4-2-1 to Chemical Formula 4-2-3, Y is O; or S, R44 to R56 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; 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 Substituted C2 to C60 heterocycloalkyl; Substituted or unsubstituted C6 to C60 aryl; Substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)R101R102; -SiR101R102R103; -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101 , R102 and R103 are the same or different from each other, and each independently is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 aryl group; C60 heteroaryl, and L1 and m have the same definitions as in Chemical Formula 2.

In one embodiment of the present disclosure, R44 to R46 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

In another embodiment of the present disclosure, R44 to R46 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

In another embodiment of the present disclosure, R44 to R46 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, R44 to R46 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; or Substituted or unsubstituted naphthyl.

In one embodiment of the present disclosure, R47 to R51 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

In another embodiment of the present disclosure, R47 to R51 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

In another embodiment of the present disclosure, R47 to R51 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, R47 to R51 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; Substituted or unsubstituted naphthyl; substituted or unsubstituted carbazolyl; substituted or unsubstituted dibenzofuryl; substituted or unsubstituted dibenzothienyl; substituted or unsubstituted substituted naphthobenzofuranyl; substituted or unsubstituted benzocarbazolyl; or substituted or unsubstituted naphthobenzothienyl.

In one embodiment of the present disclosure, R52 to R56 are the same or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 A heteroaryl group, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring.

In another embodiment of the present disclosure, R52 to R56 are the same or different from each other, and are independently hydrogen; deuterium; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocyclic ring .

In another embodiment of the present disclosure, R52 to R56 are the same or different from each other, and are independently hydrogen; deuterium; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocyclic ring .

In another embodiment of the present disclosure, R52 to R56 are the same or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted terphenyl; substituted or unsubstituted carbazolyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted Dibenzothienyl; substituted or unsubstituted naphthobenzofuryl; or substituted or unsubstituted naphthobenzothienyl, or two or more groups adjacent to each other may be bonded to each other combined to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.

In one embodiment of the present disclosure, Chemical Formula 1 may be a heterocyclic compound represented by any one of the following compounds.

In addition, by introducing various substituents to the structure of Chemical Formula 1, compounds having unique properties of the introduced substituents can be synthesized. For example, by introducing hole injection layer materials, electron blocking layer materials, hole transport layer materials, light emitting layer materials, electron transport layer materials, and hole blocking layer materials commonly used in the manufacture of organic light emitting devices into the core structure And the substituents of the material of the charge generation layer, the 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 controlled, and at the same time, properties at the interface between organic materials can be enhanced, and material applications can be diversified .

In addition, an embodiment of the present disclosure relates to an organic light-emitting element, and the organic light-emitting element includes: first electrode; a second electrode disposed opposite the first electrode; and one or more organic material layers, disposed between the first electrode and the second electrode, wherein at least one of the one or more layers of the organic material layer includes a heterocyclic compound represented by Chemical Formula 1.

In one embodiment of the present disclosure, the first electrode may be a positive electrode, and the second electrode may be a negative electrode.

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

In another embodiment of the present disclosure, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the red organic light emitting device.

In another embodiment of the present disclosure, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the blue organic light emitting device.

In another embodiment of the present disclosure, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the green organic light emitting device.

In one embodiment of the present disclosure, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light emitting layer material of the red organic light emitting device.

In another embodiment of the present disclosure, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light emitting layer material of the blue organic light emitting device.

In another embodiment of the present disclosure, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light emitting layer material of the green organic light emitting device.

Specific explanations on the heterocyclic compound represented by Chemical Formula 1 are the same as those provided above.

In addition to using the above-mentioned heterocyclic compounds to form one or more organic material layers, common organic light-emitting device manufacturing methods and materials can be used to manufacture the organic light-emitting device of the present disclosure.

When manufacturing an organic light emitting element, the heterocyclic compound may be formed as an organic material layer using a solution coating method and a vacuum deposition method. Herein, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spray method, Roll coating and the like, but not limited thereto.

The organic material layer of the organic light-emitting device disclosed herein can be formed in a single-layer structure, but can also be formed in a multi-layer structure in which two or more organic material layers are laminated. For example, the organic light-emitting device of the present disclosure may have a layer including a hole injection layer, an electron blocking layer, a hole transport layer, a light emitting layer, an electron transport layer, a hole blocking layer, an electron injection layer, and the like as an organic material layer. structure. 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 device according to an embodiment of the present disclosure, the organic material layer including the heterocyclic compound represented by Chemical Formula 1 further includes a heterocyclic compound represented by Chemical Formula 5 below. [chemical formula 5]

In Chemical Formula 5, R61 to R70 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; 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)R101R102 ; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 Heterocyclic ring, wherein R101, R102 and R103 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 A substituted C2 to C60 heteroaryl, R71 is a substituted or unsubstituted C6 to C60 aryl; a substituted or unsubstituted C2 to C60 heteroaryl; or the following chemical formula 6, when the heteroaryl of the heteroaryl When the atom is N, including a heteroatom, [Chemical Formula 6] In chemical formula 6, L2 is a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl, n is an integer from 1 to 5, and when n is 2 or greater than 2, L2 is the same or different from each other, and Ar1 and Ar2 are the same or different from each other, and are each independently substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 hetero Aryl, and * is the point of attachment to the following chemical formula 7, [chemical formula 7] X2 is NRe; O; S; CRfRg; or a direct bond, and Re, Rf, Rg, and R81 to R84 are the same or different from each other, and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; 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 alkane Oxygen; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted -P(=O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 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 one embodiment of the present disclosure, R61 to R70 are the same or different from each other, and are independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C2 to C30 alkenyl; substituted or unsubstituted C2 to C30 alkynyl; substituted or unsubstituted C1 to C30 alkoxy; substituted or unsubstituted C3 to C30 cycloalkyl; substituted or unsubstituted C2 to C30 heterocycloalkyl; substituted or unsubstituted C6 to C30 aryl; substituted or unsubstituted C2 to C30 heteroaryl; -P(=O)R101R102; -SiR101R102R103 ; or -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocyclic ring , wherein R101, R102 and R103 are the same or different from each other, and can each be independently substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted Substituted C2 to C30 heteroaryl.

In another embodiment of the present disclosure, R61 to R70 are the same or different from each other, and are independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted Substituted C2 to C20 alkenyl; substituted or unsubstituted C2 to C20 alkynyl; substituted or unsubstituted C1 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; Substituted or unsubstituted C2 to C20 heterocycloalkyl; Substituted or unsubstituted C6 to C20 aryl; Substituted or unsubstituted C2 to C20 heteroaryl; -P(=O)R101R102;- SiR101R102R103; or -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 hetero ring, and R101, R102, and R103 are the same or different from each other, and can each be independently substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted Substituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, R61 to R70 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, R61 to R70 are the same or different from each other, and each independently can be hydrogen; or deuterium.

In one embodiment of the present disclosure, R71 may be a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or a group represented by Chemical Formula 6, and when When the heteroatom of the heteroaryl is N, one heteroatom may be included.

In another embodiment of the present disclosure, R71 may be a substituted or unsubstituted C6-C20 aryl group; a substituted or unsubstituted C2-C20 heteroaryl group; or a group represented by Chemical Formula 6, and When the heteroatom of the heteroaryl is N, one heteroatom may be included.

In another embodiment of the present disclosure, R71 can be substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthrenyl; substituted or unsubstituted dibenzothienyl; substituted or unsubstituted dibenzofuryl; substituted or unsubstituted carbazolyl; substituted or unsubstituted naphtho a benzofuryl group; a substituted or unsubstituted naphthobenzothienyl group; or a group represented by Chemical Formula 6.

In one embodiment of the present disclosure, L2 may be a substituted or unsubstituted C6-C30 arylylene group; or a substituted or unsubstituted C2-C30 heteroarylylene group.

In another embodiment of the present disclosure, L2 may be a substituted or unsubstituted C6-C20 arylylene; or a substituted or unsubstituted C2-C20 heteroaryl.

In another embodiment of the present disclosure, L2 may be an unsubstituted or deuterium-substituted C6-C20 arylylene group; or an unsubstituted or deuterium-substituted C2-C20 heteroarylyl group.

In one embodiment of the present disclosure, Ar1 and Ar2 are the same or different from each other, and can be independently substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl .

In another embodiment of the present disclosure, Ar1 and Ar2 are the same or different from each other, and can be independently substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl base.

In another embodiment of the present disclosure, Ar1 and Ar2 are the same or different from each other, and each independently can be an unsubstituted or deuterium-substituted C6-C20 aryl group; or an unsubstituted or deuterium-substituted C2-C20 aryl group heteroaryl.

In another embodiment of the present disclosure, Ar1 and Ar2 are the same or different from each other, and can be independently substituted or unsubstituted phenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted substituted or unsubstituted fluorenyl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothienyl.

In one embodiment of the present disclosure, Re, Rf, Rg, and R81 to R84 are the same or different from each other, and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C30 alkyl; Substituted or unsubstituted C2 to C30 alkenyl; substituted or unsubstituted C2 to C30 alkynyl; substituted or unsubstituted C1 to C30 alkoxy; substituted or unsubstituted C3 to C30 Cycloalkyl; substituted or unsubstituted C2 to C30 heterocycloalkyl; substituted or unsubstituted C6 to C30 aryl; substituted or unsubstituted C2 to C30 heteroaryl; -P(= O) R101R102; -SiR101R102R103; or -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or substituted or unsubstituted C2 to C30 heterocyclic ring, wherein R101, R102 and R103 are the same or different from each other, and can each be independently substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2 to C30 heteroaryl.

In another embodiment of the present disclosure, Re, Rf, Rg, and R81 to R84 are the same or different from each other, and each is independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl ; substituted or unsubstituted C2 to C20 alkenyl; substituted or unsubstituted C2 to C20 alkynyl; substituted or unsubstituted C1 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 heterocycloalkyl; substituted or unsubstituted C6 to C20 aryl; substituted or unsubstituted C2 to C20 heteroaryl; -P( =O) R101R102; -SiR101R102R103; or -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or substituted or unsubstituted Substituted C2 to C20 heterocyclic ring, wherein R101, R102 and R103 are the same or different from each other, and can each be independently substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl ; or a substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, Re, Rf, Rg, and R81 to R84 are the same or different from each other, and each independently can be hydrogen; deuterium; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, Re may be substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; or substituted or unsubstituted terphenyl.

In another embodiment of the present disclosure, Rf and Rg are the same or different from each other, and can each be independently substituted or unsubstituted C1-C20 alkyl.

In another embodiment of the present disclosure, Rf and Rg are the same or different from each other, and can each be independently substituted or unsubstituted methyl.

In another embodiment of the present disclosure, R81 to R84 are the same or different from each other, and each independently can be hydrogen; or deuterium.

In one embodiment of the present disclosure, the compound represented by Chemical Formula 5 may not contain deuterium as a substituent, or may have more than 0%, 1% or more than 1%, 10% or more, based on the total number of hydrogen atoms and deuterium atoms Greater than 10%, 20% or greater than 20%, 30% or greater than 30%, 40% or greater than 40%, or 50% or greater than 50% and 100% or less than 100%, 90% or less than 90%, 80% or A deuterium content of less than 80%, 70% or less, or 60% or less.

In another embodiment of the present disclosure, the compound represented by Chemical Formula 5 may not contain deuterium as a substituent, or may have a deuterium content of 1% to 100% based on the sum of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, the compound represented by Chemical Formula 5 may not contain deuterium as a substituent, or may have a deuterium content of 20% to 90% based on the sum of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, the compound represented by Chemical Formula 5 may not contain deuterium as a substituent, or may have a deuterium content of 30% to 80% based on the sum of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, the compound represented by Chemical Formula 5 may not contain deuterium as a substituent, or may have a deuterium content of 50% to 70% based on the sum of hydrogen atoms and deuterium atoms.

When the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 are contained at the same time, the effects of superior efficiency and lifespan are obtained. This might lead to the prediction that an exciplex phenomenon would occur when the two compounds are included at the same time.

The excited complex phenomenon is due to the electron exchange between two molecules that releases the HOMO energy level of the donor (p-body) and the lowest unoccupied molecular orbital (Lowest Unoccupied Molecular Orbital, LUMO) of the acceptor (n-body). The phenomenon of energy of the size of the energy level. When an excited complex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) occurs, and thus, the internal quantum efficiency of fluorescence can be increased to 100%. When a donor (p-host) with desirable hole-transporting ability and an acceptor (n-host) with desirable electron-transporting ability are used as hosts of the light-emitting layer, holes are injected into the p-host, and electrons is implanted into the n-body, and the driving voltage can be reduced, which thus contributes to lifetime enhancement. In other words, when the compound represented by Chemical Formula 1 is used as an acceptor and the compound represented by Chemical Formula 5 is used as a donor, excellent element properties are obtained.

In one embodiment of the present disclosure, when the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 are included at the same time, at least one of the compounds does not contain deuterium as a substituent, or contains a hydrogen atom Based on the total number of deuterium atoms, there may be more than 0%, 1% or more, 10% or more than 10%, 20% or more than 20%, 30% or more than 30%, 40% or more than 40%, or 50% % or greater than 50% and 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less deuterium content.

In another embodiment of the present disclosure, when the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 are included at the same time, at least one of the compounds does not contain deuterium as a substituent, or contains hydrogen Atoms may have a deuterium content of 1% to 100% based on the total number of deuterium atoms.

In another embodiment of the present disclosure, when the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 are included at the same time, at least one of the compounds does not contain deuterium as a substituent, or contains hydrogen The atoms may have a deuterium content of 20% to 90% based on the total number of deuterium atoms.

In another embodiment of the present disclosure, when the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 are included at the same time, at least one of the compounds does not contain deuterium as a substituent, or contains hydrogen The atoms may have a deuterium content of 30% to 80% based on the total number of deuterium atoms.

In another embodiment of the present disclosure, when the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 are included at the same time, at least one of the compounds does not contain deuterium as a substituent, or contains hydrogen The atoms may have a deuterium content of 50% to 70% based on the total number of deuterium atoms.

In one embodiment of the present disclosure, the heterocyclic compound represented by Chemical Formula 5 may be any one selected from the following compounds.

In addition, an embodiment of the present disclosure provides a composition for an organic material layer of an organic light emitting device, the composition including the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5.

Specific explanations about the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 are the same as those provided above.

In an embodiment of the present disclosure, in the composition of the organic material layer for an organic light-emitting element, the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 may have a ratio of 1:10 to 10:1 , 1:8 to 8:1, 1:5 to 5:1 or 1:2 to 2:1 weight ratio, however, the ratio is not limited thereto.

When forming an organic material of an organic light-emitting element, the composition for an organic material layer of an organic light-emitting element can be used, and specifically, when forming a host of a light-emitting layer, the composition for an organic light-emitting element can be more preferably used. The composition of the organic material layer of the light-emitting device.

In one embodiment of the present disclosure, the organic material layer includes the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5, and a phosphorescent dopant may be used together therewith.

As the phosphorescent dopant material, 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 can be used, however, the scope of the present disclosure is not limited by this limited by some examples.

M can be iridium, platinum, osmium or similar material.

L is an anionic bidentate ligand coordinated to M by sp ² carbon and heteroatoms, and X can play the role of trapping electrons or holes. Non-limiting examples of L may include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, phenylpyridine , benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, tolylpyridine, and similar materials. Non-limiting examples of X' and X'' may include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinoline salts and similar materials.

Specific examples of the phosphorescent dopant are shown below, however, the phosphorescent dopant is not limited to these examples.

In one embodiment of the present disclosure, the organic material layer includes the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5, and an iridium-based dopant may be used together therewith.

In one embodiment of the present disclosure, as an iridium dopant, (piq) ₂ (Ir)(acac) can be used as a red phosphorescent dopant, or Ir(ppy) ₃ can be used as a green phosphorescent dopant.

In an embodiment of the present disclosure, based on the total weight of the light emitting layer, the content of the dopant may be 1% to 15%, preferably 2% to 10%, and more preferably 3% to 7%.

In an organic light emitting device according to an embodiment of the present disclosure, 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 a heterocyclic compound represented by Chemical Formula 1.

In an organic light emitting device according to another embodiment of the present disclosure, 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 a heterocyclic compound represented by Chemical Formula 1.

In an organic light-emitting element according to another embodiment, 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 a heterocyclic compound represented by Chemical Formula 1 .

In the organic light emitting element according to another embodiment, the organic material layer includes a light emitting layer, and the light emitting layer may include a heterocyclic compound represented by Chemical Formula 1.

In the organic light emitting element according to another embodiment, the organic material layer includes a light emitting layer including a host material, and the host material may include a heterocyclic compound represented by Chemical Formula 1.

In the organic light-emitting element according to another embodiment, the light-emitting layer may include two or more host materials, and at least one of the host materials may include the heterocyclic compound represented by Chemical Formula 1, and the other may include the heterocyclic compound represented by Chemical Formula The heterocyclic compound represented by 5.

In the organic light emitting element according to another embodiment, two or more host materials may be premixed and used in the light emitting layer, and at least one of the two or more host materials may contain The heterocyclic compound, while the other may contain the heterocyclic compound represented by Chemical Formula 5.

Pre-mixing means that the two or more host materials of the emissive layer are first mixed in one supply before being deposited on the organic material layer.

An organic light-emitting device according to an embodiment of the present disclosure may further include one layer, 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 blocking layer, and a hole blocking layer. layer or more.

1 to 3 illustrate the stacking sequence of electrodes and organic material layers of an organic light emitting device according to an embodiment of the present disclosure. However, the scope of the present application is not limited by these figures, and structures of organic light-emitting devices known in the art can also be used in the present application.

FIG. 1 shows an organic light emitting device in which a positive electrode 200 , an organic material layer 300 and a negative electrode 400 are sequentially stacked on a substrate 100 . However, the structure of 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 obtained.

FIG. 3 shows 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 such a laminated structure, and layers other than the light emitting layer may not be included and other necessary functional layers may be further added as needed.

An embodiment of the present disclosure provides a method for manufacturing an organic light emitting device, the method including the following steps: Prepare the substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the one or more layers of organic material, The step of forming the one or more organic material layers includes the step of using the composition for an organic material layer according to an embodiment of the present disclosure to form the one or more organic material layers.

In one embodiment of the present disclosure, forming the organic material layer may be formed using a thermal vacuum deposition method after premixing the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5. Referring to FIG.

Pre-mixing means that before depositing the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 on the organic material layer, the materials are first mixed in one supply source.

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

The organic material layer including the heterocyclic compound represented by Chemical Formula 1 may further include other materials as needed.

The organic material layer including both the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 may further contain other materials as needed.

In the organic light-emitting element according to one embodiment of the present disclosure, materials other than the heterocyclic compound represented by Chemical Formula 1 or the heterocyclic compound represented by Chemical Formula 5 are shown below, however, these materials are only for illustration It is not intended to limit the scope of the application and such materials may be substituted by materials known in the art.

As the positive electrode material, materials each having a relatively large work function can be used, and transparent conductive oxides, metals, conductive polymers, or the like can 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, materials each having a relatively small work function can be used, and metals, metal oxides, conductive polymers, or 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 structure materials such as LiF/Al or LiO ₂ /Al; and similar materials, but not limited thereto.

As the hole injection layer material, known hole injection layer materials can be used, and for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429; or literature [Advanced Material (Advanced Material ), 6, p. 677 (1994)] star burst amine derivatives described in, for example tris (4-carbazolyl-9-ylphenyl) amine (tris (4-carbazolyl-9-ylphenyl) amine, TCTA), 4,4',4''-tris[phenyl(m-tolyl)amino]triphenylamine (4,4',4''-tris[phenyl(m-tolyl)amino] triphenylamine, m-MTDATA) or 1,3,5-tris[4-(3-methylphenylanilino)phenyl]benzene (1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene , m-MTDAPB); soluble conductive polymers such as polyaniline/dodecylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate), polyaniline /camphorsulfonic acid or polyaniline/poly(4-styrenesulfonate); and similar materials.

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

As materials for the electron transport layer, oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone di Metal complexes of methane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, dibenzoquinone derivatives, 8-hydroxyquinoline and its derivatives and similar materials, and also High-molecular materials as well as low-molecular materials are used.

As an example of the material of the electron injection layer, LiF is generally used in this art, however, the present application is not limited thereto.

As the light emitting layer material, red, green or blue light emitting materials can be used, and two or more kinds of light emitting materials can be mixed and used as needed. Herein, when used, the two or more luminescent materials may be deposited as separate supplies, or may be pre-mixed and deposited as one supply. In addition, a fluorescent material can also be used as the light-emitting layer material, however, a phosphorescent material can also be used. As the light-emitting layer material, a material that emits light alone by combining holes and electrons respectively injected from the positive electrode and the negative electrode can be used, however, a material having a host material and a dopant material that participate in light emission together can also be used .

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

Depending on the materials used, the organic light-emitting device according to an embodiment of the present disclosure may be a top-emission type, a bottom-emission type, or a dual-emission type ).

The heterocyclic compound according to an embodiment of the present disclosure can also be used in organic electronics including organic solar cells, organic photoconductors, organic transistors, and similar components based on principles similar to those in organic light-emitting devices. element.

In the following, preferred examples are provided to help understand the present disclosure, however, the following examples are provided only for easier understanding of the present disclosure, and the present disclosure is not limited thereto. < Preparation example > Preparation example 1. Preparation of compound A Preparation Example 1-1. Preparation of Compound 1-A

Dissolve 1H-1-azadibenzo[g,i,j]naphtho[2,1,8-cde]azulene (30 g, 103 mmol/L (mM)) in chloroform (500 mL ), bromine (Br ₂ ) (5.3 ml, 103 mmol/L) was slowly added dropwise thereto, and then the mixture was stirred for 1 hour.

After the reaction was completed, methanol (300 mL) was added thereto to obtain Compound 1-A (35.1 g, yield 92%). Preparation Example 1-2. Preparation of Compound A

Compound 1-A (20 g, 54 mmol/L), 2-(bromophenyl)boronic acid (14.1 g, 70.2 mmol/L), tris(dibenzylideneacetone)dipalladium (Pd ₂ (dba) ₃ ) (9.9 g, 10.8 mmol/L), tricyclohexylphosphine (P(Cy) ₃ ) (12.1 g, 43.2 mmol/L) and 1,8-diazabicyclo[5.4 .0] Undec-7-ene (1,8-diazabicyclo[5.4.0]undec-7-ene, DBU) (20 ml) was dissolved in dimethylformamide (dimethylformamide, DMF), and then The mixture was refluxed for 8 hours.

Thereafter, after completion of the reaction, the resultant was stirred after introducing water (H ₂ O) (300 mL) thereto at room temperature, and then subjected to vacuum filtration. The reaction material was purified by column chromatography (dichloromethane (DCM):hexane=1:3 (volume ratio)), and recrystallized with methanol to obtain the target Compound A (13.9 g, 70.4% yield). Preparation Example 2. Preparation of Compound B Preparation Example 2-1. Preparation of Compound 5-B

1H-1-Azadibenzo[g,i,j]naphtho[2,1,8-cde]azulene (30 g, 103 mmol/L), di-tert-butyl dicarbonate ( di-tert-butyl dicarbonate) (27 g, 123.6 mmol/L) and 4-dimethylaminopyridine (4-dimethylaminopyridine, DMAP) (12.6 g, 103 mmol/L) were dissolved in acetonitrile (500 mL ), and then the mixture was stirred at room temperature for 1 h.

After the reaction was completed, the resultant was vacuum filtered and washed with water/methanol (H ₂ O/MeOH) to obtain compound 5-B (31.8 g, yield 78.8%). Preparation Example 2-2. Preparation of Compound 4-B

After compound 5-B (31 g, 79.2 mmol/L) was dissolved in chloroform (500 mL), bromine (Br ₂ ) (4.1 mL, 79.2 mmol/L) was slowly added dropwise thereto, And then the mixture was stirred for 1 hour. After the reaction was completed, methanol (300 mL) was added thereto to obtain Compound 4-B (28.1 g, 75.4%). Preparation Example 2-3. Preparation of Compound 3-B

Compound 4-B (28 g, 59.5 mmol/L), 2-chloroaniline (9.1 g, 71.4 mmol/L), tris(dibenzylideneacetone) dipalladium (Pd ₂ (dba) ₃ ) (1.7 g, 3 mmol/L), 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, Sphos) (2.5 g , 6 mmol/L) and sodium tert-butoxide (NaOtBu) (11.4 g, 119 mmol/L) were dissolved in toluene (500 mL), and then the mixture was refluxed for 1 hour.

After the reaction was completed, the reaction material was purified by column chromatography (dichloromethane: hexane = 1:3 (volume ratio)) to obtain compound 3-B (28.1 g, yield 91.3%) . Preparation Example 2-4. Preparation of Compound 2-B

Compound 3-B (28 g, 54.2 mmol/L), tris(dibenzylideneacetone) dipalladium (Pd ₂ (dba) ₃ ) (4.9 g, 5.4 mmol/L), tricyclohexyl Phosphine (P(Cy) ₃ ) (6.1 g, 21.7 mmol/L) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (30 ml) were dissolved in di Toluene (400 ml), and then the mixture was refluxed for 24 hours.

After the reaction was completed, the reaction material was purified by column chromatography (dichloromethane:hexane=1:3 (volume ratio)) to obtain compound 2-B (13.5 g, yield 51.8%) . Preparation Example 2-5. Preparation of Compound 1-B

Compound 2-B (13.5 g, 28.1 mmol/L), iodobenzene (6.9 g, 33.7 mmol/L), tris(dibenzylideneacetone) dipalladium (Pd ₂ (dba) ₃ ) ( 0.8 g, 1.4 mmol/L), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (Sphos) (1.1 g, 2.8 mmol/L) and sodium tert-butoxide (NaOtBu) (5.4 g, 56.2 mmol/l) was dissolved in xylene (500 ml), and the mixture was then refluxed for 1 hour.

After the reaction was completed, the reaction material was purified by column chromatography (dichloromethane:hexane=1:3 (volume ratio)) to obtain compound 1-B (13.1 g, yield 83.6%) . Preparation Example 2-6. Preparation of Compound B

Compound 1-B (13.1 g, 23.5 mmol/L) and trifluoroacetic acid (16 mL) were dissolved in dichloromethane (DCM) (150 mL), and then the mixture was stirred for 1 hr.

After the reaction was completed, the reaction material was purified by column chromatography (dichloromethane:hexane=1:3 (volume ratio)) to obtain the target compound B (9.8 g, yield 88.5%). Preparation Example 3. Preparation of Compound C Preparation Example 3-1. Preparation of Compound 3-C

After dissolving 1H-1-azadibenzo[g,i,j]naphtho[2,1,8-cde]azulene (30 g, 103 mmol/L) in chloroform (500 mL) , bromine (Br ₂ ) (5.3 ml, 103 mmol/L) was slowly added dropwise thereto, and then the mixture was stirred for 1 hour.

After the reaction was completed, methanol (300 mL) was added thereto to obtain Compound 3-C (35.1 g, yield 92.0%). Preparation Example 3-2. Preparation of Compound 2-C

Compound 3-C (35 grams, 94.5 mmol/liter), (2-(methylthio) phenyl) boronic acid (17.5 grams, 104 mmol/liter), tetrakis(triphenylphosphine) palladium ( 0) (Pd(PPh ₃ ) ₄ ) (5.4 g, 4.7 mmol/L) and potassium carbonate (K ₂ CO ₃ ) (26.1 g, 189 mmol/L) were dissolved in toluene (400 mL) and water (H ₂ O) (80 ml), and then the mixture was refluxed for 8 hours.

After the reaction was completed, the resultant was stirred after adding water (H ₂ O) (300 mL) thereto at room temperature, and then extracted. The reaction material was purified by column chromatography (dichloromethane:hexane=1:3 (volume ratio)) to obtain compound 2-C (31.2 g, yield 79.8%). Preparation Example 3-3. Preparation of Compound 1-C

Compound 2-C (31 g, 75 mmol/L) was dissolved in glacial acetic acid (400 mL), and then the mixture was stirred. After that, hydrogen peroxide (H ₂ O ₂ ) (2.5 g, 75 mmol/L) dissolved in acetic acid was slowly added dropwise thereto, and then the resultant was stirred for 12 hours.

After the reaction was completed, the resultant was concentrated at room temperature, and then vacuum-filtered to obtain Compound 1-C (30.5 g, yield 94.7%). Preparation Example 3-4. Preparation of Compound C

Compound 1-C (30 g, 69.8 mmol/L) was dissolved in dichloromethane (DCM) (600 mL), and after slowly introducing trifluoromethanesulfonic acid (120 mL) thereto, the mixture was stirred for 24 hours. After that, the reaction material was added to a solution (3000 mL) obtained by mixing water (H ₂ O) and pyridine at a volume ratio of 8:1, and then the resultant was refluxed for 30 minutes.

The resultant was vacuum filtered at room temperature, and then purified by column chromatography (dichloromethane:hexane=1:5 (volume ratio)) to obtain the target compound C (14.2 g, Yield 51.1%). Preparation Example 4. Preparation of Compound D Preparation Example 4-1. Preparation of Compound 2-D

Compound 4-B (25 g, 53.1 mmol/L), 2-chlorophenol (7.5 g, 58.4 mmol/L) and cesium carbonate (Cs ₂ CO ₃ ) (34.6 g, 106.2 mmol/L l) was dissolved in dimethylamine (DMA) (300 ml), and then the mixture was refluxed for 1 hour.

After the reaction was completed, the reaction material was purified by column chromatography (dichloromethane:hexane=1:4 (volume ratio)) to obtain compound 2-D (17.9 g, yield 65.2%) . Preparation Example 4-2. Preparation of Compound 1-D

Compound 2-D (17.9 g, 34.6 mmol/L), palladium acetate (Pd(OAc) ₂ ) (0.8 g, 3.5 mmol/L), tricyclohexylphosphine tetrafluoroborate (PCy ₃ · HBF ₄ ) (2.5 g, 6.9 mmol/L) and potassium carbonate (K ₂ CO ₃ ) (19.1 g, 138.4 mmol/L) were dissolved in dimethylamine (DMA) (200 ml), and then The mixture was refluxed for 12 hours.

After the reaction was completed, the reaction material was purified by column chromatography (dichloromethane:hexane=1:3 (volume ratio)) to obtain compound 1-D (12.5 g, yield 75.1%) . Preparation Example 4-3. Preparation of Compound D

Compound 1-D (12.5 g, 26.0 mmol/L) and trifluoroacetic acid (20 mL) were dissolved in dichloromethane (DCM) (150 mL), and then the mixture was stirred for 1 hr.

After the reaction was completed, the reaction material was purified by column chromatography (dichloromethane:hexane=1:1 (volume ratio)) to obtain the target compound D (7.4 g, yield 74.6%). Preparation Example 5. Preparation of Compound E Preparation Example 5-1. Preparation of Compound 2-E

Compound 4-B (20.0 g, 42.5 mmol/L), 2-chlorobenzenethiol (7.4 g, 51.0 mmol/L), copper iodide (CuI) (8.1 g, 42.5 mmol/L l), cyclohexane-1,2-diamine (4.9 g, 42.5 mmol/L) and potassium phosphate (K ₃ PO ₄ ) (18 g, 85.0 mmol/L) were dissolved in 1,4- dioxane (250 ml), and then the mixture was refluxed for 1 hour.

After the reaction was completed, the reaction material was purified by column chromatography (dichloromethane:hexane=1:4 (volume ratio)) to obtain compound 2-E (16.2 g, yield 71.3%) . Preparation Example 5-2. Preparation of Compound 1-E

Compound 2-E (16 g, 30 mmol/L), palladium acetate (Pd(OAc) ₂ ) (0.7 g, 3 mmol/L), tricyclohexylphosphine tetrafluoroborate (PCy ₃ · HBF ₄ ) (2.2 g, 6 mmol/L) and potassium carbonate (K ₂ CO ₃ ) (16.6 g, 120 mmol/L) were dissolved in dimethylamine (DMA) (200 ml), and then The mixture was refluxed for 12 hours.

After the reaction was completed, the reaction material was purified by column chromatography (dichloromethane:hexane=1:3 (volume ratio)) to obtain compound 1-E (10.7 g, yield 71.7%) . Preparation Example 5-3. Preparation of Compound E

Compound 1-E (10.7 g, 21.5 mmol/L) and trifluoroacetic acid (16 mL) were dissolved in dichloromethane (DCM) (150 mL), and then the mixture was stirred for 1 hr.

After the reaction was completed, the reaction material was purified by column chromatography (dichloromethane:hexane=1:1 (volume ratio)) to obtain the target compound E (7.5 g, yield 87.9%). Preparation Example 6. Preparation of Compound 1-1-3

2,4-Dichloroquinazoline (20 g, 100.5 mmol/L), [1,1'-biphenyl]-3-ylboronic acid (29.9 g, 150.8 mmol/L), tetrakis(tri Phenylphosphine) palladium(0) (Pd(PPh ₃ ) ₄ ) (5.8 g, 5.0 mmol/L) and sodium carbonate (Na ₂ CO ₃ ) (21.3 g, 201 mmol/L) dissolved in THF (tetrahydrofuran, THF) (250 ml) and water (H ₂ O) (50 ml), and then the mixture was refluxed.

After that, water (H ₂ O) (200 ml) was added thereto, and the resultant was subjected to vacuum filtration to obtain compound 1-1-3 (22.3 g, yield 70%).

As in Table 1 below, except Intermediate A of Table 1 below is used instead of 2,4-dichloroquinazoline and Intermediate B of Table 1 below is used instead of [1,1'-biphenyl]-3-ylboronic acid , The title compound was prepared in the same manner as in Preparation Example 6. The target compounds in Table 1 below are compounds corresponding to R11 of the heterocyclic compound of Chemical Formula 1 of the present disclosure. [Table 1] Compound number Intermediate A Intermediate B target compound yield 1-1-4 69.8% 1-1-20 67.5% 1-1-22 67.1% 1-1-96 67.1% 1-1-115 64.7% 1-1-131 65.2% 1-1-133 64.9% 1-1-184 65.1% 1-1-221 62.5% 1-1-222 61.9% 1-1-365 69.9% 1-1-374 65.5% 1-1-384 66.1% 1-1-436 68.9% 1-1-441 68.5% 1-1-443 60.3% 1-1-448 67.9% 1-1-478 70.5% Preparation Example 7. Preparation of Compound 1-1-483 Preparation Example 7-1. Preparation of Compound 1-3-483

_{Trifluoromethanesulfonic} acid (24.6 mL, 278.9 mmol/L), and then the mixture was stirred for 1 hour.

After the reaction was completed, methanol (300 ml) was introduced thereto to terminate the reaction, and Compound 1-3-483 (9.5 g, yield 91.4%) was obtained. Preparation Example 7-2. Preparation of Compound 1-2-483

Compound 1-3-483 (9.5 g, 39.2 mmol/L), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis( 1,3,2-dioxaborane) (11.9 g, 47.0 mmol/L), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (PdCl ₂ (dppf)) (1.5 g, 2.0 mmol/L) and potassium acetate (KOAc) (7.7 g, 78.4 mmol/L) were dissolved in 1,4-dioxane (100 mL), and then The mixture was refluxed for 1 hour.

The reaction material was purified by column chromatography (dichloromethane:hexane=1:3 (volume ratio)), and recrystallized from methanol to obtain compound 1-2-483 (11 g, Yield 96.9%). Preparation Example 7-3. Preparation of Compound 1-1-483

Compound 1-2-483 (11 g, 38 mmol/L), 2,4-dichloroquinazoline (8.3 g, 41.8 mmol/L), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh ₃ ) ₄ ) (2.2 g, 1.9 mmol/L) and potassium carbonate (K ₂ CO ₃ ) (10.5 g, 76.0 mmol/L) were dissolved in 1,4-dioxane (100 ml) and water (H ₂ O) (20 ml), and then the mixture was refluxed for 1 hour.

The reaction material was vacuum filtered and then recrystallized using methanol to obtain the target compound 1-1-483 (8.9 g, yield 71.3%). Preparation Example 8. Preparation of Compound 1-1-484 Preparation Example 8-1. Preparation of Compound 1-2-484

[1,1'-biphenyl]-3-ylboronic acid (10 g, 50.5 mmol/L), 2,4-dichloroquinazoline (11.1 g, 55.6 mmol/L), tetrakis(tri Phenylphosphine) palladium(0) (Pd(PPh ₃ ) ₄ ) (2.9 g, 2.5 mmol/L) and potassium carbonate (K ₂ CO ₃ ) (14.0 g, 101.0 mmol/L) were dissolved in 1 , 4-dioxane (100 ml) and water (H ₂ O) (20 ml), and then the mixture was refluxed for 1 hour.

The reaction material was vacuum filtered and then recrystallized using methanol to obtain compound 1-2-484 (12.1 g, yield 75.6%). Preparation Example 8-2. Preparation of Compound 1-1-484

After compound 1-2-484 (12 g, 37.9 mmol/L) was dissolved in benzene-d ₆ (120 ml), trifluoromethanesulfonic acid (21.8 ml, 246.4 mmol ears/L), and then the mixture was stirred for 1 hour.

After the reaction was completed, methanol (300 ml) was introduced thereto to terminate the reaction, and the target compound 1-1-484 (11.4 g, yield 91.3%) was obtained. Preparation Example 9. Preparation of Compound 1-1-486 Preparation Example 9-1. Preparation of Compound 1-3-486

1-Bromobenzene-2,3,4,5,6-d ₅ (20 g, 123.4 mmol/L), 4,4,4',4',5,5,5',5'- Octamethyl-2,2'-bis(1,3,2-dioxaborolane) (47 g, 185.1 mmol/L), [1,1'-bis(diphenylphosphine)dicene Fe]palladium(II) chloride ( _PdCl2 (dppf)) (4.5 g, 6.2 mmol/L) and potassium acetate (KOAc) (30.3 g, 308.5 mmol/L) were dissolved in 1,4- dioxane (200 ml), and then the mixture was refluxed for 1 hour.

The reaction material was purified by column chromatography (dichloromethane:hexane=1:3 (volume ratio)), and recrystallized from methanol to obtain compound 1-3-486 (21.9 g, Yield 84.8%). Preparation Example 9-2. Preparation of Compound 1-2-486

2,4,6-trichloro-1,3,5-triazine (8 g, 43.4 mmol/L), compound 1-3-486 (19 g, 91.1 mmol/L), tetra( Triphenylphosphine) palladium(0) (Pd(PPh ₃ ) ₄ ) (2.5 g, 2.2 mmol/L) and potassium carbonate (K ₂ CO ₃ ) (15 g, 108.5 mmol/L) were dissolved in 1,4-Dioxane (100 ml) and water (H ₂ O) (20 ml), and then the mixture was refluxed for 1 hour.

The reaction material was vacuum filtered and then recrystallized using methanol to obtain compound 1-2-486 (9 g, yield 74.7%). Preparation Example 9-3. Preparation of Compound 1-1-486

Compound 1-2-486 (9 g, 32.4 mmol/L), (4-chloronaphthalen-1-yl) boronic acid (6.7 g, 32.4 mmol/L), tetrakis(triphenylphosphine) palladium (0)(Pd(PPh ₃ ) ₄ ) (1.8 g, 1.6 mmol/L) and potassium carbonate (K ₂ CO ₃ ) (11.2 g, 81 mmol/L) were dissolved in 1,4-diox Alkanes (100 ml) and water (H ₂ O) (20 ml), and then the mixture was refluxed for 1 hour.

The reaction material was vacuum filtered and then recrystallized using methanol to obtain the target compound 1-1-486 (11.1 g, yield 84.9%). Preparation Example 10. Preparation of Compound 1-1-487 Preparation Example 10-1. Preparation of Compound 1-2-487

2-Chloro-4,6-diphenyl-1,3,5-triazine (10 g, 37.4 mmol/L), (4-chloronaphthalen-1-yl)boronic acid (7.7 g, 37.4 mol/L), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh ₃ ) ₄ ) (2.2 g, 1.9 mmol/L) and potassium carbonate (K ₂ CO ₃ ) (12.9 g, 93.5 mmol/L) was dissolved in 1,4-dioxane (100 mL) and water (H ₂ O) (20 mL), and then the mixture was refluxed for 1 hour.

The reaction material was vacuum filtered and then recrystallized using methanol to obtain compound 1-2-487 (12.1 g, yield 82.1%). Preparation Example 10-2. Preparation of Compound 1-1-487

After compound 1-2-487 (12 g, 30.5 mmol/L) was dissolved in benzene-d ₆ (120 ml), trifluoromethanesulfonic acid (17.5 ml, 198.3 mmol ears/L), and then the mixture was stirred for 1 hour.

After the reaction was completed, methanol (300 ml) was introduced thereto to terminate the reaction, and Compound 1-1-487 (11.4 g, yield 91.1%) was obtained. Preparation Example 11. Preparation of Compound 1-3

Compound 1-1-3 (10 grams, 31.6 mmol/liter) prepared in Preparation Example 6, Compound B (14.4 grams, 31.6 mmol/liter) prepared in Preparation Example 2 and cesium carbonate ( (Cs ₂ CO ₃ ) (20.6 g, 63.2 mmol/l) was dissolved in dimethylamine (DMA) (140 ml), and the mixture was then refluxed. After that, water (H ₂ O) (200 ml) was added thereto, and the resultant was subjected to vacuum filtration to obtain target compound 1-3 (19.1 g, yield 82%).

As in Table 2 below, in the same manner as in Preparation Example 11, except that Intermediate C of Table 2 below was used instead of Compound 1-1-3 and any one of Compound A to Compound E was used as Intermediate D The target compound was prepared. [Table 2] Compound number Intermediate C Intermediate D target compound yield 1-4 81.9% 1-20 78.5% 1-22 78.7% 1-95 78.1% 1-96 78.2% 1-115 79.1% 1-131 75.1% 1-133 75.4% 1-183 70.5% 1-184 70.6% 1-221 70.7% 1-222 71.5% 1-234 72.1% 1-363 85.3% 1-365 85.5% 1-374 77.1% 1-384 75.9% 1-436 85.9% 1-438 86.3% 1-440 86.5% 1-441 87.1% 1-443 83.5% 1-446 75.1% 1-448 75.3% 1-469 80.1% 1-478 75.3% 1-483 85.8% 1-484 84.9% 1-486 80.1% 1-487 80.3% 1-489 85.5% Preparation Example 12. Preparation of Compound 1-485

After compound 1-438 (10 g, 15.5 mmol/L) was dissolved in benzene-d ₆ (120 mL), trifluoromethanesulfonic acid (8.9 mL, 100.8 mmol/L) was slowly added dropwise thereto. liter), and then the mixture was stirred at a temperature of 80 °C for 1 h.

After the reaction was completed, methanol (300 mL) was introduced thereto to terminate the reaction, and the target compound 1-485 (9.6 g, yield 91.3%) was obtained.

As in Table 3 below, the target compound was prepared in the same manner as in Preparation Example 12, except that Intermediate E of Table 3 below was used instead of Compound 1-483. [table 3] Compound number Intermediate E target compound yield 1-240 93.1% 1-488 92.1% 1-490 91.8%

The synthesis results of the compounds described in Preparation Example 1 to Preparation Example 12 and Table 2 and Table 3 are shown in Table 4 and Table 5 below. In addition, the synthesis results of compounds corresponding to the heterocyclic compound of Chemical Formula 1 of the present disclosure are also shown in Table 4 and Table 5 below.

Table 4 below shows ¹H nuclear magnetic resonance (nuclear magnetic resonance, NMR) (CDCl ₃, 300 megahertz), and Table 5 below shows the measured values of field desorption (FD)-mass spectrometry (MS) (FD-MS: field desorption mass spectrometry). [Table 4] compound ¹ H NMR (CDCl ₃ , 300 MHz) 1-3 δ=8.42~8.40(m, 2H), 8.13~8.10(m, 4H), 7.94~7.88(m, 3H), 7.73~7.65(m, 8H), 7.61~7.49(m, 8H), 7.24~7.10 (m, 6H), 7.00~6.99(t, 1H) 1-4 δ=8.46~8.42(m, 3H), 8.13~8.03(m, 7H), 7.93~7.85(m, 5H), 7.72~7.48(m, 8H), 7.24~7.10(m, 6H), 7.00~6.99 (t, 1H) 1-20 δ=8.86~8.85(d, 1H), 8.45~8.42(m, 3H), 8.19~8.10(m, 5H), 7.94~7.93(d, 1H), 7.89~7.88(d, 1H), 7.80~7.72 (m 3H), 7.67~7.50(m, 8H), 7.45~7.30(m, 8H), 7.20~7.00(m, 5H) 1-22 δ=8.44~8.39(m, 4H), 8.11~8.09(m, 3H), 7.98~7.80(m, 10H), 7.54~7.53(d, 1H), 7.39~7.33(m, 6H), 7.25~7.14 (m, 5H), 7.00~6.99(t, 1H) 1-95 δ=8.51~8.45(m, 4H), 8.16~8.13(m, 3H), 7.95~7.84(m, 4H), 7.72~7.49(m, 8H), 7.33~7.31(m, 1H), 7.19~7.15 (m, 3H) 1-96 δ=8.50~8.44(m, 4H), 8.15~8.13(m, 3H), 7.94~7.84(m, 6H), 7.72~7.49(m, 10H), 7.33~7.31(m, 1H), 7.19~7.15 (m, 3H) 1-115 δ=8.91~8.90(d, 2H), 8.45~8.42(m, 2H), 8.13~8.11(m, 2H), 7.94~7.80(m, 5H), 7.72~7.67(m, 6H), 7.49~7.35 (m, 7H), 7.19~7.15(m, 3H), 1-131 δ=8.85~8.84(d, 2H), 8.45~8.42(m, 2H), 8.25~8.23(d, 1H), 8.15~8.11(m, 3H), 7.95~7.88(m, 4H), 7.72~7.55 (m, 6H), 7.41~7.33(m, 3H), 7.22~7.15(m, 4H), 1-133 δ=8.89(s, 1H), 8.45~8.42(m, 2H), 8.26~8.25(d, 1H), 8.13~8.10(m, 2H), 7.95~7.88(m, 4H), 7.75~7.65(m , 8H), 7.49~7.35(m, 5H), 7.23~7.15(m, 4H), 1-183 δ=8.50~8.42(m, 4H), 8.15~8.11(m, 3H), 7.94~7.84(m, 5H), 7.74~7.53(m, 10H), 7.41~7.33(m, 5H) 1-184 δ=8.49(s, 1H), 8.45~8.42(m, 2H), 8.15~8.11(m, 3H), 7.94~7.84(m, 6H), 7.74~7.53(m, 10H), 7.41~7.33(m , 5H) 1-221 δ=8.55~8.54(d, 2H), 8.42~8.41(m, 2H), 8.15~8.08(m, 3H), 7.94~7.83(m, 5H), 7.75~7.49(m, 10H), 7.35~7.24 (m, 5H) 1-222 δ=8.57~8.55(d, 2H), 8.42~8.41(m, 2H), 8.15~8.11(m, 5H), 7.98~7.85(m, 6H), 7.75~7.54(m, 9H), 7.33~7.24 (m, 5H) 1-224 δ=8.87~8.85(m, 4H), 8.41~8.40(m, 2H), 8.10~8.08(d, 2H), 7.94~7.80(m, 2H), 7.75~7.57(m, 10H), 7.33~7.24 (m, 4H) 1-363 δ=8.42~8.41(m, 2H), 8.13~8.10(m, 3H), 7.94~7.73(m, 9H), 7.61~7.41(m, 8H), 7.33~7.24(m, 5H) 1-365 δ=8.42~8.41(m, 2H), 8.26~8.25(d, 1H), 8.20~8.19(d, 1H), 8.13~8.10(m, 4H), 7.94~7.83(m, 5H), 7.62~7.42 (m, 12H), 7.33~7.20(m, 5H) 1-374 δ=8.51~8.50(m, 2H), 8.42~8.41(m, 2H), 8.10~8.09(m, 2H), 7.95~7.94(d, 1H), 7.80~7.71(m, 6H), 7.67~7.57 (m, 5H), 7.49~7.42(m, 6H), 7.33~7.29(m, 3H) 1-384 δ=8.42~8.41(m, 2H), 8.11~8.10(m, 2H), 8.04~8.03(d, 1H), 7.98~7.82(m, 4H), 7.76(s, 1H), 7.70~7.57(m , 7H), 7.42~7.27(m, 8H) 1-436 δ=8.42~8.40(m, 4H), 8.13~8.10(m, 5H), 7.94~7.80(m, 8H), 7.65~7.58(m, 3H), 7.49~7.47(m, 2H), 7.34~7.33 (t, 1H) 1-438 δ=8.42~8.40(m, 4H), 8.13~8.10(m, 5H), 7.94~7.84(m, 7H), 7.80~7.73(m, 5H), 7.61~7.41(m, 6H), 1-440 δ=8.42~8.40(m, 4H), 8.25~8.24(d, 1H), 8.20~8.19(d, 1H), 8.13~8.10(m, 6H), 8.94~8.80(m, 6H), 7.62~7.50 (m, 10H), 7.34~7.33(t, 1H), 7.24~7.23(t, 1H) 1-441 δ=8.42~8.40(m, 4H), 8.13~8.10(m, 5H), 7.98~7.80(m, 10H), 7.58~7.48(m, 3H), 7.39~7.33(m, 3H) 1-443 δ=8.54~8.53(d, 1H), 8.42~8.40(m, 4H), 8.13~8.10(m, 5H), 8.03(d, 1H), 7.99~7.82(m, 9H), 7.60~7.48(m , 6H), 7.33~7.32(t, 1H) 1-447 δ=8.51~8.50(m, 2H), 8.43~8.81(m, 4H), 8.11~8.10(m, 4H), 7.86~7.75(m, 10H), 7.67~7.65(m, 2H), 7.49~7.41 (m, 4H), 7.34~7.33(t, 1H) 1-449 δ=8.77~8.76(d, 1H), 8.66~8.65(d, 1H), 8.45~8.43(m, 4H), 8.30(s, 1H), 8.19~8.18(d, 1H), 8.10~8.08(m , 4H), 7.94~7.80(m, 6H), 7.67~7.48(m, 10H), 7.33~7.32(t, 1H), 7.20~7.19(t, 1H) 1-469 δ=8.80~8.78(d, 2H), 8.42~8.36(m, 5H), 8.11~8.10(m, 4H), 7.94~7.88(m, 4H), 7.80~7.73(m, 4H), 7.61~7.60 (t, 1H), 7.50~7.47(m, 7H), 7.33~7.32(t, 1H) 1-478 δ=8.97~8.96(d, 1H), 8.81~8.80(m, 4H), 8.42~8.40(m, 4H), 8.24~8.23(d, 1H), 8.12~8.10(m, 5H), 7.94~7.88 (m, 3H), 7.80~7.78(m, 2H), 7.59~7.48(m, 9H), 7.32~7.31(t, 1H) 1-483 δ=8.45~8.40(m, 4H), 8.13~8.10(m, 5H), 7.94~7.88(m, 3H), 7.83~7.80(m, 3H), 7.58~7.56(m, 1H), 7.48~7.47 (d, 1H), 7.33~7.31(t, 1H) 1-484 δ=8.44~8.40(m, 4H), 8.11~8.09(m, 4H), 7.94~7.88(m, 3H), 7.81~7.80(d, 1H), 7.48~7.47(d, 1H), 7.33~7.31 (t, 1H) 1-486 δ=8.97~8.96(d, 1H), 8.41~8.38(m, 4H), 8.24~8.23(d, 1H), 8.12~8.09(m, 5H), 7.94~7.89(m, 3H), 7.80~7.78 (m, 2H), 7.55~7.48(m, 3H), 7.32~7.30(t, 1H) 1-487 δ=8.42~8.40(m, 4H), 8.12~8.10(m, 4H), 7.95~7.90(m, 3H), 7.81~7.80(d, 1H), 7.49~7.48(d, 1H), 7.33~7.32 (t, 1H) 1-489 δ=8.45~8.43(m, 2H), 8.13~8.10(m, 3H), 7.94~7.90(m, 2H), 7.88~7.86(m, 2H), 7.58~7.56(m, 4H), 7.43~7.42 (d, 1H), 7.33~7.30(m, 3H), 7.24~7.22(t, 1H) [table 5] compound FD-Mass compound FD-Mass 1-1 m/z=660.7800 (C ₄₈ H ₂₈ N ₄ , 660.2314) 1-2 m/z=736.8780 (C ₅₄ H ₃₂ N ₄ , 736.2627) 1-3 m/z=736.8780 (C ₅₄ H ₃₂ N ₄ , 736.2627) 1-4 m/z=710.8400 (C ₅₂ H ₃₀ N ₄ , 710.2470) 1-5 m/z=825.9750 (C ₆₀ H ₃₅ N ₄ , 825.2892) 1-6 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-7 m/z=766.9220 (C ₅₄ H ₃₀ N ₄ S, 766.2191) 1-8 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2756) 1-9 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2756) 1-10 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2756) 1-11 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2756) 1-12 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2756) 1-13 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2756) 1-14 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2756) 1-15 m/z=660.7800 (C ₄₈ H ₂₈ N ₄ , 660.2314) 1-16 m/z=710.8400 (C ₅₂ H ₃₀ N ₄ , 710.2470) 1-17 m/z=736.8780 (C ₅₄ H ₃₂ N ₄ , 736.2627) 1-18 m/z=736.8780 (C ₅₄ H ₃₂ N ₄ , 736.2627) 1-19 m/z=786.9380 (C ₅₈ H ₃₄ N ₄ , 786.2783) 1-20 m/z=825.9750 (C ₆₀ H ₃₅ N ₄ , 825.2892) 1-21 m/z=825.9750 (C ₆₀ H ₃₅ N ₄ , 825.2892) 1-22 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-23 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-24 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-25 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2576) 1-26 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2576) 1-27 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2576) 1-28 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2576) 1-29 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2576) 1-30 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2576) 1-31 m/z=816.9820 (C ₅₈ H ₃₂ N ₄ S, 816.2348) 1-32 m/z=816.9820 (C ₅₈ H ₃₂ N ₄ S, 816.2348) 1-33 m/z=700.8010 (C ₅₀ H ₂₈ N ₄ O, 700.2263) 1-34 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-35 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-36 m/z=776.8990 (C ₅₆ H ₃₂ N ₄ O, 776.2576) 1-37 m/z=776.8990 (C ₅₆ H ₃₂ N ₄ O, 776.2576) 1-38 m/z=852.9970 (C ₆₂ H ₃₆ N ₄ O, 852.2889) 1-39 m/z=826.9590 (C ₆₀ H ₃₄ N ₄ O, 826.2733) 1-40 m/z=865.9960 (C ₆₂ H ₃₅ N ₅ O, 865.2842) 1-41 m/z=865.9960 (C ₆₂ H ₃₅ N ₅ O, 865.2842) 1-42 m/z=790.8820 (C ₅₆ H ₃₀ N ₄ O ₂ , 790.2369) 1-43 m/z=790.8820 (C ₅₆ H ₃₀ N ₄ O ₂ , 790.2369) 1-44 m/z=806.9430 (C ₅₆ H ₃₀ N ₄ OS, 806.2140) 1-45 m/z=840.9420 (C ₆₀ H ₃₂ N ₄ O ₂ , 840.2525) 1-46 m/z=840.9420 (C ₆₀ H ₃₂ N ₄ O ₂ , 840.2525) 1-47 m/z=857.0030 (C ₆₀ H ₃₂ N ₄ OS, 856.2297) 1-48 m/z=857.0030 (C ₆₀ H ₃₂ N ₄ OS, 856.2297) 1-49 m/z=716.8620 (C ₅₀ H ₂₈ N ₄ S, 716.2035) 1-50 m/z=766.9220 (C ₅₄ H ₃₀ N ₄ S, 766.2191) 1-51 m/z=766.9220 (C ₅₄ H ₃₀ N ₄ S, 766.2191) 1-52 m/z=792.9600 (C ₅₆ H ₃₂ N ₄ S, 792.2348) 1-53 m/z=792.9600 (C ₅₆ H ₃₂ N ₄ S, 792.2348) 1-54 m/z=843.0200 (C ₆₀ H ₃₄ N ₄ S, 842.2504) 1-55 m/z=882.0570 (C ₆₂ H ₃₅ N ₅ S, 881.2613) 1-56 m/z=882.0570 (C ₆₂ H ₃₅ N ₅ S, 881.2613) 1-57 m/z=806.9430 (C ₅₆ H ₃₀ N ₄ OS, 806.2140) 1-58 m/z=806.9430 (C ₅₆ H ₃₀ N ₄ OS, 806.2140) 1-59 m/z=823.0040 (C ₅₆ H ₃₀ N ₄ S ₂ , 822.1912) 1-60 m/z=823.0040 (C ₅₆ H ₃₀ N ₄ S ₂ , 822.1912) 1-61 m/z=857.0030 (C ₆₀ H ₃₂ N ₄ OS, 856.2297) 1-62 m/z=857.0030 (C ₆₀ H ₃₂ N ₄ OS, 856.2297) 1-63 m/z=857.0030 (C ₆₀ H ₃₂ N ₄ OS, 856.2297) 1-64 m/z=857.0030 (C ₆₀ H ₃₂ N ₄ OS, 856.2297) 1-65 m/z=687.8060 (C ₄₉ H ₂₉ N ₅ , 687.2423) 1-66 m/z=737.8660 (C ₅₃ H ₃₁ N ₅ , 737.2579) 1-67 m/z=737.8660 (C ₅₃ H ₃₁ N ₅ , 737.2579) 1-68 m/z=787.9260 (C ₅₇ H ₃₃ N ₅ , 787.2736) 1-69 m/z=787.9260 (C ₅₇ H ₃₃ N ₅ , 787.2736) 1-70 m/z=787.9260 (C ₅₇ H ₃₃ N ₅ , 787.2736) 1-71 m/z=763.9040 (C ₅₅ H ₃₃ N ₅ , 787.2736) 1-72 m/z=840.0020 (C ₆₁ H ₃₇ N ₅ , 839.3049) 1-73 m/z=813.9640 (C ₅₉ H ₃₅ N ₅ , 813.2892) 1-74 m/z=777.8870 (C ₅₅ H ₃₁ N ₅ O, 777.2529) 1-75 m/z=777.8870 (C ₅₅ H ₃₁ N ₅ O, 777.2529) 1-76 m/z=793.8480 (C ₅₅ H ₃₁ N ₅ S, 793.2300) 1-77 m/z=827.9470 (C ₅₉ H ₃₃ N ₅ O, 827.2685) 1-78 m/z=686.8180 (C ₅₀ H ₃₀ N ₄ , 686.2470) 1-79 m/z=736.8780 (C ₅₄ H ₃₂ N ₄ , 736.2627) 1-80 m/z=762.9160 (C ₅₆ H ₃₄ N ₄ , 762.2783) 1-81 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-82 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-83 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2576) 1-84 m/z=826.9590 (C ₆₀ H ₃₄ N ₄ O, 826.2733) 1-85 m/z=762.9160 (C ₅₆ H ₃₄ N ₄ , 762.2783) 1-86 m/z=812.9760 (C ₆₀ H ₃₆ N ₄ , 812.2940) 1-87 m/z=839.0140 (C ₆₂ H ₃₈ N ₄ , 838.3096) 1-88 m/z=762.9160 (C ₅₆ H ₃₄ N ₄ , 762.2783) 1-89 m/z=813.9640 (C ₅₉ H ₃₅ N ₅ , 813.2892) 1-90 m/z=864.0240 (C ₆₃ H ₃₇ N ₅ , 863.3049) 1-91 m/z=786.9380 (C ₅₈ H ₃₄ N ₄ , 786.2783) 1-92 m/z=826.9590 (C ₆₀ H ₃₄ N ₄ O, 826.2733) 1-93 m/z=833.0799 (C ₅₉ H ₁₆ D ₁₉ N ₅ , 832.4085) 1-94 m/z=741.0231 (C ₅₂ H ₃₀ N ₄ , 740.4353) 1-95 m/z=585.6660 (C ₄₂ H ₂₃ N ₃ O, 585.1841) 1-96 m/z=661.7640 (C ₄₈ H ₂₇ N ₃ O, 661.2154) 1-97 m/z=661.7640 (C ₄₈ H ₂₇ N ₃ O, 661.2154) 1-98 m/z=635.7260 (C ₄₆ H ₂₅ N ₃ O, 635.1998) 1-99 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-100 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-101 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2576) 1-102 m/z=675.7470 (C ₄₈ H ₂₅ N ₃ O ₂ , 675.1947) 1-103 m/z=675.7470 (C ₄₈ H ₂₅ N ₃ O ₂ , 675.1947) 1-104 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2576) 1-105 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2576) 1-106 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2576) 1-107 m/z=725.8070 (C ₅₂ H ₂₇ N ₃ O ₂ , 725.2103) 1-108 m/z=725.8070 (C ₅₂ H ₂₇ N ₃ O ₂ , 725.2103) 1-109 m/z=801.9050 (C ₅₈ H ₃₁ N ₃ O ₂ , 801.2416) 1-110 m/z=725.8070 (C ₅₂ H ₂₇ N ₃ O ₂ , 725.2103) 1-111 m/z=725.8070 (C ₅₂ H ₂₇ N ₃ O ₂ , 725.2103) 1-112 m/z=741.8680 (C ₅₂ H ₂₇ N ₃ OS, 741.1875) 1-113 m/z=585.6660 (C ₄₂ H ₂₃ N ₃ O, 585.1841) 1-114 m/z=635.7260 (C ₄₆ H ₂₅ N ₃ O, 635.1998) 1-115 m/z=661.7640 (C ₄₈ H ₂₇ N ₃ O, 661.2154) 1-116 m/z=661.7640 (C ₄₈ H ₂₇ N ₃ O, 661.2154) 1-117 m/z=711.8240 (C ₅₂ H ₂₉ N ₃ O, 711.2311) 1-118 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-119 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-120 m/z=675.7470 (C ₄₈ H ₂₅ N ₃ O ₂ , 675.1947) 1-121 m/z=751.8450 (C ₅₄ H ₂₉ N ₃ O ₂ , 751.2260) 1-122 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2576) 1-123 m/z=725.8070 (C ₅₂ H ₂₇ N ₃ O ₂ , 725.2103) 1-124 m/z=725.8070 (C ₅₂ H ₂₇ N ₃ O ₂ , 725.2103) 1-125 m/z=725.8070 (C ₅₂ H ₂₇ N ₃ O ₂ , 725.2103) 1-126 m/z=725.8070 (C ₅₂ H ₂₇ N ₃ O ₂ , 725.2103) 1-127 m/z=725.8070 (C ₅₂ H ₂₇ N ₃ O ₂ , 725.2103) 1-128 m/z=801.9050 (C ₅₈ H ₃₁ N ₃ O ₂ , 801.2416) 1-129 m/z=741.8680 (C ₅₂ H ₂₇ N ₃ OS, 741.1875) 1-130 m/z=625.6870 (C ₄₄ H ₂₃ N ₃ O ₂ , 625.1790) 1-131 m/z=675.7470 (C ₄₈ H ₂₅ N ₃ O ₂ , 675.1947) 1-132 m/z=701.7850 (C ₅₀ H ₂₇ N ₃ O ₂ , 701.2103) 1-133 m/z=701.7850 (C ₅₀ H ₂₇ N ₃ O ₂ , 701.2103) 1-134 m/z=751.8450 (C ₅₄ H ₂₉ N ₃ O ₂ , 751.2260) 1-135 m/z=731.8290 (C ₅₀ H ₂₅ N ₃ O ₂ S, 731.1667) 1-136 m/z=840.9420 (C ₆₀ H ₃₂ N ₄ O ₂ , 840.2525) 1-137 m/z=765.8280 (C ₅₄ H ₂₇ N ₃ O ₃ , 765.2052) 1-138 m/z=765.8280 (C ₅₄ H ₂₇ N ₃ O ₃ , 765.2052) 1-139 m/z=641.7480 (C ₄₄ H ₂₃ N ₃ OS, 641.1562) 1-140 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-141 m/z=717.8460 (C ₅₀ H ₂₇ N ₃ OS, 717.1875) 1-142 m/z=717.8460 (C ₅₀ H ₂₇ N ₃ OS, 717.1875) 1-143 m/z=806.9430 (C ₅₆ H ₃₀ N ₄ OS, 806.2140) 1-144 m/z=806.9430 (C ₅₆ H ₃₀ N ₄ OS, 806.2140) 1-145 m/z=731.8290 (C ₅₀ H ₂₅ N ₃ O ₂ S, 731.1667) 1-146 m/z=731.8290 (C ₅₀ H ₂₅ N ₃ O ₂ S, 731.1667) 1-147 m/z=781.8890 (C ₅₄ H ₂₇ N ₃ O ₂ S, 781.1824) 1-148 m/z=781.8890 (C ₅₄ H ₂₇ N ₃ O ₂ S, 781.1824) 1-149 m/z=781.8890 (C ₅₄ H ₂₇ N ₃ O ₂ S, 781.1824) 1-150 m/z=781.8890 (C ₅₄ H ₂₇ N ₃ O ₂ S, 781.1824) 1-151 m/z=781.8890 (C ₅₄ H ₂₇ N ₃ O ₂ S, 781.1824) 1-152 m/z=797.9500 (C ₅₄ H ₂₇ N ₃ OS ₂ , 797.1596) 1-153 m/z=611.7040 (C ₄₄ H ₂₅ N ₃ O, 611.1998) 1-154 m/z=661.7640 (C ₄₈ H ₂₇ N ₃ O, 661.2154) 1-155 m/z=711.8240 (C ₅₂ H ₂₉ N ₃ O, 711.2311) 1-156 m/z=687.8020 (C ₅₀ H ₂₉ N ₃ O, 687.2311) 1-157 m/z=611.7040 (C ₄₄ H ₂₅ N ₃ O, 611.1998) 1-158 m/z=687.8020 (C ₅₀ H ₂₉ N ₃ O, 687.2311) 1-159 m/z=612.6920 (C ₄₃ H ₂₄ N ₄ O, 612.1950) 1-160 m/z=688.7900 (C ₄₉ H ₂₈ N ₄ O, 688.2263) 1-161 m/z=662.7520 (C ₄₇ H ₂₆ N ₄ O, 662.2107) 1-162 m/z=712.8120 (C ₅₁ H ₂₈ N ₄ O, 712.2263) 1-163 m/z=701.7890 (C ₄₉ H ₂₇ N ₅ O, 701.2216) 1-164 m/z=777.8870 (C ₅₅ H ₃₁ N ₅ O, 777.2529) 1-165 m/z=702.7730 (C ₄₉ H ₂₆ N ₄ O ₂ , 702.2056) 1-166 m/z=778.8710 (C ₅₅ H ₃₀ N ₄ O ₂ , 778.2369) 1-167 m/z=752.8330 (C ₅₃ H ₂₈ N ₄ O ₂ , 752.2212) 1-168 m/z=828.9310 (C ₅₉ H ₃₂ N ₄ O ₂ , 828.2525) 1-169 m/z=752.8330 (C ₅₃ H ₂₈ N ₄ O ₂ , 752.2212) 1-170 m/z=768.8940 (C ₅₃ H ₂₈ N ₄ OS, 768.1984) 1-171 m/z=688.7900 (C ₄₉ H ₂₈ N ₄ O, 688.2263) 1-172 m/z=688.7900 (C ₄₉ H ₂₈ N ₄ O, 688.2263) 1-173 m/z=738.8500 (C ₅₃ H ₃₀ N ₄ O, 738.2420) 1-174 m/z=788.9100 (C ₅₇ H ₃₂ N ₄ O, 788.2576) 1-175 m/z=711.8240 (C ₅₂ H ₂₉ N ₃ O, 711.2311) 1-176 m/z=761.8840 (C ₅₆ H ₃₁ N ₃ O, 761.2467) 1-179 m/z=737.8620 (C ₅₄ H ₃₁ N ₃ O, 737.2467) 1-178 m/z=787.9220 (C ₅₈ H ₃₃ N ₃ O, 787.2624) 1-179 m/z=675.8494 (C ₄₈ H ₁₃ D ₁₄ N ₃ O, 675.3033) 1-180 m/z=688.9287 (C ₄₈ D ₂₇ N ₃ O, 688.3849) 1-181 m/z=752.9354 (C ₅₃ H ₁₆ D ₁₄ N ₄ O, 752.3298) 1-182 m/z=601.7270 (C ₄₂ H ₂₃ N ₃ S, 601.1613) 1-183 m/z=677.8250 (C ₄₈ H ₂₇ N ₃ S, 677.1926) 1-184 m/z=677.8250 (C ₄₈ H ₂₇ N ₃ S, 677.1926) 1-185 m/z=651.7870 (C ₄₆ H ₂₅ N ₃ S, 651.1769) 1-186 m/z=766.9220 (C ₅₄ H ₃₀ N ₄ S, 766.2191) 1-187 m/z=766.9220 (C ₅₄ H ₃₀ N ₄ S, 766.2191) 1-188 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-189 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-190 m/z=707.8690 (C ₄₈ H ₂₅ N ₃ S ₂ , 707.1490) 1-191 m/z=741.8680 (C ₅₂ H ₂₇ N ₃ OS, 741.1875) 1-192 m/z=741.8680 (C ₅₂ H ₂₇ N ₃ OS, 741.1875) 1-193 m/z=741.8680 (C ₅₂ H ₂₇ N ₃ OS, 741.1875) 1-194 m/z=741.8680 (C ₅₂ H ₂₇ N ₃ OS, 741.1875) 1-195 m/z=757.9290 (C ₅₂ H ₂₇ N ₃ S ₂ , 757.1646) 1-196 m/z=601.7270 (C ₄₂ H ₂₃ N ₃ S, 601.1613) 1-197 m/z=651.7870 (C ₄₆ H ₂₅ N ₃ S, 651.1769) 1-198 m/z=677.8250 (C ₄₈ H ₂₇ N ₃ S, 677.1926) 1-199 m/z=677.8250 (C ₄₈ H ₂₇ N ₃ S, 677.1926) 1-200 m/z=766.9220 (C ₅₄ H ₃₀ N ₄ S, 766.2191) 1-201 m/z=766.9220 (C ₅₄ H ₃₀ N ₄ S, 766.2191) 1-202 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-203 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-204 m/z=816.9820 (C ₅₈ H ₃₂ N ₄ S, 816.2348) 1-205 m/z=741.8680 (C ₅₂ H ₂₇ N ₃ OS, 741.1875) 1-206 m/z=741.8680 (C ₅₂ H ₂₇ N ₃ OS, 741.1875) 1-207 m/z=641.7480 (C ₄₄ H ₂₃ N ₃ OS, 641.1562) 1-208 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-209 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-210 m/z=717.8460 (C ₅₀ H ₂₇ N ₃ OS, 717.1875) 1-211 m/z=806.9430 (C ₅₆ H ₃₀ N ₄ OS, 806.2140) 1-212 m/z=806.9430 (C ₅₆ H ₃₀ N ₄ OS, 806.2140) 1-213 m/z=731.8290 (C ₅₀ H ₂₅ N ₃ O ₂ S, 731.1667) 1-214 m/z=747.8900 (C ₅₀ H ₂₅ N ₃ OS ₂ , 747.1439) 1-215 m/z=747.8900 (C ₅₀ H ₂₅ N ₃ OS ₂ , 747.1439) 1-216 m/z=781.8890 (C ₅₄ H ₂₇ N ₃ O ₂ S, 781.1824) 1-217 m/z=781.8890 (C ₅₄ H ₂₇ N ₃ O ₂ S, 781.1824) 1-218 m/z=657.8090 (C ₄₄ H ₂₃ N ₃ S ₂ , 657.1333) 1-219 m/z=707.8690 (C ₄₈ H ₂₅ N ₃ S ₂ , 707.1490) 1-220 m/z=707.8690 (C ₄₈ H ₂₅ N ₃ S ₂ , 707.1490) 1-221 m/z=733.9070 (C ₅₀ H ₂₇ N ₃ S ₂ , 733.1646) 1-222 m/z=783.9670 (C ₅₄ H ₂₉ N ₃ S ₂ , 783.1803) 1-223 m/z=823.0040 (C ₅₆ H ₃₀ N ₄ S ₂ , 822.1912) 1-224 m/z=747.8900 (C ₅₀ H ₂₅ N ₃ OS ₂ , 747.1439) 1-225 m/z=747.8900 (C ₅₀ H ₂₅ N ₃ OS ₂ , 747.1439) 1-226 m/z=797.9500 (C ₅₄ H ₂₇ N ₃ OS ₂ , 797.1596) 1-227 m/z=797.9500 (C ₅₄ H ₂₇ N ₃ OS ₂ , 797.1596) 1-228 m/z=797.9500 (C ₅₄ H ₂₇ N ₃ OS ₂ , 797.1596) 1-229 m/z=814.0110 (C ₅₄ H ₂₇ N ₃ S ₃ , 813.1367) 1-230 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-231 m/z=767.9060 (C ₅₄ H ₂₉ N ₃ O _S , 767.2031) 1-232 m/z=767.9060 (C ₅₄ H ₂₉ N ₃ OS, 767.2031) 1-233 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-234 m/z=628.7530 (C ₄₃ H ₂₄ N ₄ S, 628.1722) 1-235 m/z=704.8510 (C ₄₉ H ₂₈ N ₄ S, 704.2035) 1-236 m/z=754.9110 (C ₅₃ H ₃₀ N ₄ S, 754.2191) 1-237 m/z=754.9110 (C ₅₃ H ₃₀ N ₄ S, 754.2191) 1-238 m/z=642.8384 (C ₄₃ H ₁₀ D ₁₄ N ₄ S, 642.2600) 1-239 m/z=768.9964 (C ₅₃ H ₁₆ D ₁₄ N ₄ S, 768.3070) 1-240 m/z=652.8994 (C ₄₃ D ₂₄ N ₄ S, 652.3228) 1-241 m/z=611.7480 (C ₄₅ H ₂₉ N ₃ , 611.2361) 1-242 m/z=687.8460 (C ₅₁ H ₃₃ N ₃ , 687.2674) 1-243 m/z=687.8460 (C ₅₁ H ₃₃ N ₃ , 687.2674) 1-244 m/z=661.8080 (C ₄₉ H ₃₁ N ₃ , 661.2518) 1-245 m/z=776.9430 (C ₅₇ H ₃₆ N ₄ , 776.2940) 1-246 m/z=776.9430 (C ₅₇ H ₃₆ N ₄ , 776.2940) 1-247 m/z=701.8290 (C ₅₁ H ₃₁ N ₃ O, 701.2467) 1-248 m/z=701.8290 (C ₅₁ H ₃₁ N ₃ O, 701.2467) 1-249 m/z=611.7480 (C ₄₅ H ₂₉ N ₃ , 611.2361) 1-250 m/z=661.8080 (C ₄₉ H ₃₁ N ₃ , 661.2518) 1-251 m/z=687.8460 (C ₅₁ H ₃₃ N ₃ , 687.2674) 1-252 m/z=687.8460 (C ₅₁ H ₃₃ N ₃ , 687.2674) 1-253 m/z=776.9430 (C ₅₇ H ₃₆ N ₄ , 776.2940) 1-254 m/z=701.8290 (C ₅₁ H ₃₁ N ₃ O, 701.2467) 1-255 m/z=701.8290 (C ₅₁ H ₃₁ N ₃ O, 701.2467) 1-256 m/z=717.8900 (C ₅₁ H ₃₁ N ₃ S, 717.2239) 1-257 m/z=751.8890(C ₅₅ H ₃₃ N ₃ O, 751.2624) 1-258 m/z=751.8890(C ₅₅ H ₃₃ N ₃ O, 751.2624) 1-259 m/z=751.8890(C ₅₅ H ₃₃ N ₃ O, 751.2624) 1-260 m/z=751.8890(C ₅₅ H ₃₃ N ₃ O, 751.2624) 1-261 m/z=651.7690(C ₄₇ H ₂₉ N ₃ O, 651.2311) 1-262 m/z=701.8290(C ₅₁ H ₃₁ N ₃ O, 701.2467) 1-263 m/z=727.8670(C ₅₃ H ₃₃ N ₃ O, 727.2624) 1-264 m/z=777.9270(C ₅₇ H ₃₅ N ₃ O, 777.2780) 1-265 m/z=638.7740(C ₄₆ H ₃₀ N ₄ , 638.2470) 1-266 m/z=714.8720(C ₅₂ H ₃₄ N ₄ , 714.2783) 1-267 m/z=688.8340(C ₅₀ H ₃₂ N ₄ , 688.2627) 1-268 m/z=738.8940(C ₅₄ H ₃₄ N ₄ , 738.2783) 1-269 m/z=803.9690(C ₅₈ H ₃₇ N ₅ , 803.3049) 1-270 m/z=727.8710(C ₅₂ H ₃₃ N ₅ , 727.2736) 1-271 m/z=714.8720(C ₅₂ H ₃₄ N ₄ , 714.2783) 1-272 m/z=764.9320(C ₅₆ H ₃₆ N ₄ , 764.2940) 1-273 m/z=660.7800 (C ₄₈ H ₂₈ N ₄ , 660.2314) 1-274 m/z=660.7800 (C ₄₈ H ₂₈ N ₄ , 660.2314) 1-275 m/z=660.7800 (C ₄₈ H ₂₈ N ₄ , 660.2314) 1-276 m/z=710.8400 (C ₅₂ H ₃₀ N ₄ , 710.2470) 1-277 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-278 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-279 m/z=766.9220 (C ₅₄ H ₃₀ N ₄ S, 766.2191) 1-280 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2756) 1-281 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2756) 1-282 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2756) 1-283 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2756) 1-284 m/z=816.9820 (C ₅₈ H ₃₂ N ₄ S, 816.2348) 1-285 m/z=660.7800 (C ₄₈ H ₂₈ N ₄ , 660.2314) 1-286 m/z=710.8400 (C ₅₂ H ₃₀ N ₄ , 710.2470) 1-287 m/z=736.8780 (C ₅₄ H ₃₂ N ₄ , 736.2627) 1-288 m/z=825.9750 (C ₆₀ H ₃₅ N ₄ , 825.2892) 1-289 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-290 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2756) 1-291 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2756) 1-292 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2756) 1-293 m/z=700.8010 (C ₅₀ H ₂₈ N ₄ O, 700.2263) 1-294 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-295 m/z=776.8990 (C ₅₆ H ₃₂ N ₄ O, 776.2576) 1-296 m/z=865.9960 (C ₆₂ H ₃₅ N ₅ O, 865.2842) 1-297 m/z=790.8820 (C ₅₆ H ₃₀ N ₄ O ₂ , 790.2369) 1-298 m/z=806.9430 (C ₅₆ H ₃₀ N ₄ OS, 806.2140) 1-299 m/z=840.9420 (C ₆₀ H ₃₂ N ₄ O ₂ , 840.2525) 1-300 m/z=840.9420 (C ₆₀ H ₃₂ N ₄ O ₂ , 840.2525) 1-301 m/z=716.8620 (C ₅₀ H ₂₈ N ₄ S, 716.2035) 1-302 m/z=766.9220 (C ₅₄ H ₃₀ N ₄ S, 766.2191) 1-303 m/z=792.9600 (C ₅₆ H ₃₂ N ₄ S, 792.2348) 1-304 m/z=792.9600 (C ₅₆ H ₃₂ N ₄ S, 792.2348) 1-305 m/z=687.8060 (C ₄₉ H ₂₉ N ₅ , 687.2423) 1-306 m/z=763.9040 (C ₅₅ H ₃₃ N ₅ , 787.2736) 1-307 m/z=737.8660 (C ₅₃ H ₃₁ N ₅ , 737.2579) 1-308 m/z=787.9260 (C ₅₇ H ₃₃ N ₅ , 787.2736) 1-309 m/z=777.8870 (C ₅₅ H ₃₁ N ₅ O, 777.2529) 1-310 m/z=777.8870 (C ₅₅ H ₃₁ N ₅ O, 777.2529) 1-311 m/z=827.9470 (C ₅₉ H ₃₃ N ₅ O, 827.2685) 1-312 m/z=686.8180 (C ₅₀ H ₃₀ N ₄ , 686.2470) 1-313 m/z=763.9040 (C ₅₅ H ₃₃ N ₅ , 787.2736) 1-314 m/z=813.9640 (C ₅₉ H ₃₅ N ₅ , 813.2892) 1-315 m/z=585.6660 (C ₄₂ H ₂₃ N ₃ O, 585.1841) 1-316 m/z=661.7640 (C ₄₈ H ₂₇ N ₃ O, 661.2154) 1-317 m/z=661.7640 (C ₄₈ H ₂₇ N ₃ O, 661.2154) 1-318 m/z=635.7260 (C ₄₆ H ₂₅ N ₃ O, 635.1998) 1-319 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-320 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-321 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-322 m/z=675.7470 (C ₄₈ H ₂₅ N ₃ O ₂ , 675.1947) 1-323 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2576) 1-324 m/z=800.9210 (C ₅₈ H ₃₂ N ₄ O, 800.2576) 1-325 m/z=725.8070 (C ₅₂ H ₂₇ N ₃ O ₂ , 725.2103) 1-326 m/z=725.8070 (C ₅₂ H ₂₇ N ₃ O ₂ , 725.2103) 1-327 m/z=741.8680 (C ₅₂ H ₂₇ N ₃ OS, 741.1875) 1-328 m/z=585.6660 (C ₄₂ H ₂₃ N ₃ O, 585.1841) 1-329 m/z=635.7260 (C ₄₆ H ₂₅ N ₃ O, 635.1998) 1-330 m/z=661.7640 (C ₄₈ H ₂₇ N ₃ O, 661.2154) 1-331 m/z=750.8610 (C ₅₄ H ₃₀ N ₄ O, 750.2420) 1-332 m/z=675.7470 (C ₄₈ H ₂₅ N ₃ O ₂ , 675.1947) 1-333 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-334 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-335 m/z=725.8070 (C ₅₂ H ₂₇ N ₃ O ₂ , 725.2103) 1-336 m/z=725.8070 (C ₅₂ H ₂₇ N ₃ O ₂ , 725.2103) 1-337 m/z=725.8070 (C ₅₂ H ₂₇ N ₃ O ₂ , 725.2103) 1-338 m/z=625.6870 (C ₄₄ H ₂₃ N ₃ O ₂ , 625.1790) 1-339 m/z=701.7850 (C ₅₀ H ₂₇ N ₃ O ₂ , 701.2103) 1-340 m/z=701.7850 (C ₅₀ H ₂₇ N ₃ O ₂ , 701.2103) 1-341 m/z=790.8820 (C ₅₆ H ₃₀ N ₄ O ₂ , 790.2369) 1-342 m/z=715.7680 (C ₅₀ H ₂₅ N ₃ O ₃ , 715.1896) 1-343 m/z=731.8290 (C ₅₀ H ₂₅ N ₃ O ₂ S, 731.1667) 1-344 m/z=765.8280 (C ₅₄ H ₂₇ N ₃ O ₃ , 765.2052) 1-345 m/z=765.8280 (C ₅₄ H ₂₇ N ₃ O ₃ , 765.2052) 1-346 m/z=765.8280 (C ₅₄ H ₂₇ N ₃ O ₃ , 765.2052) 1-347 m/z=641.7480 (C ₄₄ H ₂₃ N ₃ OS, 641.1562) 1-348 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-349 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-350 m/z=717.8460 (C ₅₀ H ₂₇ N ₃ OS, 717.1875) 1-351 m/z=612.6920 (C ₄₃ H ₂₄ N ₄ O, 612.1950) 1-352 m/z=662.7520 (C ₄₇ H ₂₆ N ₄ O, 662.2107) 1-353 m/z=738.8500 (C ₅₃ H ₃₀ N ₄ O, 738.2420) 1-354 m/z=702.7730 (C ₄₉ H ₂₆ N ₄ O ₂ , 702.2056) 1-355 m/z=611.7040 (C ₄₄ H ₂₅ N ₃ O, 611.1998) 1-356 m/z=611.7040 (C ₄₄ H ₂₅ N ₃ O, 611.1998) 1-357 m/z=661.7640 (C ₄₈ H ₂₇ N ₃ O, 661.2154) 1-358 m/z=688.7900 (C ₄₉ H ₂₈ N ₄ O, 688.2263) 1-359 m/z=738.8500 (C ₅₃ H ₃₀ N ₄ O, 738.2420) 1-360 m/z=661.7640 (C ₄₈ H ₂₇ N ₃ O, 661.2154) 1-361 m/z=601.7270 (C ₄₂ H ₂₃ N ₃ S, 601.1613) 1-362 m/z=677.8250 (C ₄₈ H ₂₇ N ₃ S, 677.1926) 1-363 m/z=677.8250 (C ₄₈ H ₂₇ N ₃ S, 677.1926) 1-364 m/z=651.7870 (C ₄₆ H ₂₅ N ₃ S, 651.1769) 1-365 m/z=766.9220 (C ₅₄ H ₃₀ N ₄ S, 766.2191) 1-366 m/z=766.9220 (C ₅₄ H ₃₀ N ₄ S, 766.2191) 1-367 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-368 m/z=707.8690 (C ₄₈ H ₂₅ N ₃ S ₂ , 707.1490) 1-369 m/z=741.8680 (C ₅₂ H ₂₇ N ₃ OS, 741.1875) 1-370 m/z=741.8680 (C ₅₂ H ₂₇ N ₃ OS, 741.1875) 1-371 m/z=757.9290 (C ₅₂ H ₂₇ N ₃ S ₂ , 757.1646) 1-372 m/z=601.7270 (C ₄₂ H ₂₃ N ₃ S, 601.1613) 1-373 m/z=651.7870 (C ₄₆ H ₂₅ N ₃ S, 651.1769) 1-374 m/z=677.8250 (C ₄₈ H ₂₇ N ₃ S, 677.1926) 1-375 m/z=727.8850 (C ₅₂ H ₂₉ N ₃ S, 727.2082) 1-376 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-377 m/z=741.8680 (C ₅₂ H ₂₇ N ₃ OS, 741.1875) 1-378 m/z=741.8680 (C ₅₂ H ₂₇ N ₃ OS, 741.1875) 1-379 m/z=641.7480 (C ₄₄ H ₂₃ N ₃ OS, 641.1562) 1-380 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-381 m/z=691.8080 (C ₄₈ H ₂₅ N ₃ OS, 691.1718) 1-382 m/z=717.8460 (C ₅₀ H ₂₇ N ₃ OS, 717.1875) 1-383 m/z=806.9430 (C ₅₆ H ₃₀ N ₄ OS, 806.2140) 1-384 m/z=731.8290 (C ₅₀ H ₂₅ N ₃ O ₂ S, 731.1667) 1-385 m/z=781.8890 (C ₅₄ H ₂₇ N ₃ O ₂ S, 781.1824) 1-386 m/z=657.8090 (C ₄₄ H ₂₃ N ₃ S ₂ , 657.1333) 1-387 m/z=733.9070 (C ₅₀ H ₂₇ N ₃ S ₂ , 733.1646) 1-388 m/z=747.8900 (C ₅₀ H ₂₅ N ₃ OS ₂ , 747.1439) 1-389 m/z=763.9510 (C ₅₀ H ₂₅ N ₃ S ₃ , 763.1211) 1-390 m/z=797.9500 (C ₅₄ H ₂₇ N ₃ OS ₂ , 797.1596) 1-391 m/z=704.8510 (C ₄₉ H ₂₈ N ₄ S, 704.2035) 1-392 m/z=754.9110 (C ₅₃ H ₃₀ N ₄ S, 754.2191) 1-393 m/z=718.9364 (C ₄₉ H ₁₄ D ₁₄ N ₄ S, 718.2913) 1-394 m/z=611.7480 (C ₄₅ H ₂₉ N ₃ , 611.2361) 1-395 m/z=687.8460 (C ₅₁ H ₃₃ N ₃ , 687.2674) 1-396 m/z=687.8460 (C ₅₁ H ₃₃ N ₃ , 687.2674) 1-397 m/z=661.8080 (C ₄₉ H ₃₁ N ₃ , 661.2518) 1-398 m/z=776.9430 (C ₅₇ H ₃₆ N ₄ , 776.2940) 1-399 m/z=701.8290 (C ₅₁ H ₃₁ N ₃ O, 701.2467) 1-400 m/z=717.8900 (C ₅₁ H ₃₁ N ₃ S, 717.2239) 1-401 m/z=827.0030 (C ₆₁ H ₃₈ N ₄ , 826.3096) 1-402 m/z=751.8890(C ₅₅ H ₃₃ N ₃ O, 751.2624) 1-403 m/z=751.8890(C ₅₅ H ₃₃ N ₃ O, 751.2624) 1-404 m/z=751.8890(C ₅₅ H ₃₃ N ₃ O, 751.2624) 1-405 m/z=611.7480 (C ₄₅ H ₂₉ N ₃ , 611.2361) 1-406 m/z=661.8080 (C ₄₉ H ₃₁ N ₃ , 661.2518) 1-407 m/z=687.8460 (C ₅₁ H ₃₃ N ₃ , 687.2674) 1-408 m/z=776.9430 (C ₅₇ H ₃₆ N ₄ , 776.2940) 1-409 m/z=701.8290 (C ₅₁ H ₃₁ N ₃ O, 701.2467) 1-410 m/z=777.9270 (C ₅₇ H ₃₅ N ₃ O, 777.2780) 1-411 m/z=777.9270 (C ₅₇ H ₃₅ N ₃ O, 777.2780) 1-412 m/z=651.7690(C ₄₇ H ₂₉ N ₃ O, 651.2311) 1-413 m/z=701.8290(C ₅₁ H ₃₁ N ₃ O, 701.2467) 1-414 m/z=727.8670(C ₅₃ H ₃₃ N ₃ O, 727.2624) 1-415 m/z=757.9110(C ₅₃ H ₃₁ N ₃ OS, 757.2188) 1-416 m/z=791.9100(C ₅₇ H ₃₃ N ₃ O ₂ , 791.2573) 1-417 m/z=791.9100(C ₅₇ H ₃₃ N ₃ O ₂ , 791.2573) 1-418 m/z=667.8300(C ₄₇ H ₂₉ N ₃ S, 667.2082) 1-419 m/z=717.8900(C ₅₁ H ₃₁ N ₃ S, 717.2239) 1-420 m/z=717.8900(C ₅₁ H ₃₁ N ₃ S, 717.2239) 1-421 m/z=743.9280(C ₅₃ H ₃₃ N ₃ S, 743.2395) 1-422 m/z=833.0250(C ₅₉ H ₃₆ N ₄ S, 832.2661) 1-423 m/z=757.9110(C ₅₃ H ₃₁ N ₃ OS, 757.2188) 1-424 m/z=757.9110(C ₅₃ H ₃₁ N ₃ OS, 757.2188) 1-425 m/z=807.9710(C ₅₇ H ₃₃ N ₃ OS, 807.2344) 1-426 m/z=638.7740(C ₄₆ H ₃₀ N ₄ , 638.2470) 1-427 m/z=688.8340(C ₅₀ H ₃₂ N ₄ , 688.2627) 1-428 m/z=714.8720(C ₅₂ H ₃₄ N ₄ , 714.2783) 1-429 m/z=727.8710(C ₅₂ H ₃₃ N ₅ , 727.2736) 1-430 m/z=728.8550(C ₅₂ H ₃₂ N ₄ O, 728.2576) 1-431 m/z=714.8720(C ₅₂ H ₃₄ N ₄ , 714.2783) 1-432 m/z=764.9320(C ₅₆ H ₃₆ N ₄ , 764.2940) 1-433 m/z=687.8460(C ₅₁ H ₃₃ N ₃ , 687.2674) 1-434 m/z=658.8960(C ₄₆ H ₁₀ D ₂₀ N ₄ , 658.3726) 1-435 m/z=785.0540(C ₅₆ H ₁₆ D ₂ 0N ₄ , 784.4195) 1-436 m/z=569.6670(C ₄₂ H ₂₃ N ₃ , 569.1892) 1-437 m/z=645.7650(C ₄₈ H ₂₇ N ₃ , 645.2205) 1-438 m/z=645.7650(C ₄₈ H ₂₇ N ₃ , 645.2205) 1-439 m/z=619.7270(C ₄₆ H ₂₅ N ₃ , 619.2048) 1-440 m/z=734.8620(C ₅₄ H ₃₀ N ₄ , 734.2470) 1-441 m/z=659.7480(C ₄₈ H ₂₅ N ₃ O, 659.1998) 1-442 m/z=784.9220(C ₅₈ H ₃₂ N ₄ , 784.2627) 1-443 m/z=709.8080(C ₅₂ H ₂₇ N ₃ O, 709.2154) 1-444 m/z=569.6670(C ₄₂ H ₂₃ N ₃ , 569.1892) 1-445 m/z=619.7270(C ₄₆ H ₂₅ N ₃ , 619.2048) 1-446 m/z=645.7650(C ₄₈ H ₂₇ N ₃ , 645.2205) 1-447 m/z=695.8250(C ₅₂ H ₂₉ N ₃ , 695.2361) 1-448 m/z=734.8620(C ₅₄ H ₃₀ N ₄ , 734.2470) 1-449 m/z=675.8090(C ₄₈ H ₂₅ N ₃ S, 675.1769) 1-450 m/z=675.8090(C ₄₈ H ₂₅ N ₃ S, 675.1769) 1-451 m/z=709.8080(C ₅₂ H ₂₇ N ₃ O, 709.2154) 1-452 m/z=609.6880(C ₄₄ H ₂₃ N ₃ O, 609.1841) 1-453 m/z=659.7480(C ₄₈ H ₂₅ N ₃ O, 659.1998) 1-454 m/z=659.7480(C ₄₈ H ₂₅ N ₃ O, 659.1998) 1-455 m/z=685.7860(C ₅₀ H ₂₇ N ₃ O, 685.2154) 1-456 m/z=774.8830(C ₅₆ H ₃₀ N ₄ O, 774.2420) 1-457 m/z=699.7690(C ₅₀ H ₂₅ N ₃ O ₂ , 699.1947) 1-458 m/z=699.7690(C ₅₀ H ₂₅ N ₃ O ₂ , 699.1947) 1-459 m/z=824.9430(C ₆₀ H ₃₂ N ₄ O, 824.2576) 1-460 m/z=749.8290(C ₅₄ H ₂₇ N ₃ O ₂ , 749.2103) 1-461 m/z=749.8290(C ₅₄ H ₂₇ N ₃ O ₂ , 749.2103) 1-462 m/z=749.8290(C ₅₄ H ₂₇ N ₃ O ₂ , 749.2103) 1-463 m/z=625.7490(C ₄₄ H ₂₃ N ₃ S, 625.1613) 1-464 m/z=675.8090(C ₄₈ H ₂₅ N ₃ S, 675.1769) 1-465 m/z=701.8470(C ₅₀ H ₂₇ N ₃ S, 701.1926) 1-466 m/z=731.8910(C ₅₀ H ₂₅ N ₃ S ₂ , 731.1490) 1-467 m/z=731.8910(C ₅₀ H ₂₅ N ₃ S ₂ , 731.1490) 1-468 m/z=596.6930(C ₄₃ H ₂₄ N ₄ , 596.2001) 1-469 m/z=672.7910(C ₄₉ H ₂₈ N ₄ , 672.2314) 1-470 m/z=672.7910(C ₄₉ H ₂₈ N ₄ , 672.2314) 1-471 m/z=646.7530(C ₄₇ H ₂₆ N ₄ , 646.2157) 1-472 m/z=696.8130(C ₅₁ H ₂₈ N ₄ , 696.2314) 1-473 m/z=686.7740(C ₄₉ H ₂₆ N ₄ O, 686.2107) 1-474 m/z=672.7910(C ₄₉ H ₂₈ N ₄ , 672.2314) 1-475 m/z=672.7910(C ₄₉ H ₂₈ N ₄ , 672.2314) 1-476 m/z=722.8510(C ₅₃ H ₃₀ N ₄ , 722.2470) 1-477 m/z=772.9110(C ₅₇ H ₃₂ N ₄ , 772.2627) 1-478 m/z=722.8510(C ₅₃ H ₃₀ N ₄ , 722.2470) 1-479 m/z=772.9110(C ₅₇ H ₃₂ N ₄ , 772.2627) 1-480 m/z=798.9490(C ₅₉ H ₃₄ N ₄ , 798.2783) 1-481 m/z=715.9324(C ₅₀ H ₁₃ N ₃ S, 715.2804) 1-482 m/z=736.9364(C ₅₃ H ₁₆ D ₁₄ N ₄ , 736.3349) 1-483 m/z=654.8199 (C ₄₈ H ₁₈ D ₉ N ₃ , 654.2770) 1-484 m/z=658.8443 (C ₄₈ H ₁₄ D ₁₃ N ₃ , 658.3021) 1-485 m/z=672.9297 (C ₄₈ D ₂₇ N ₃ , 672.3900) 1-486 m/z=732.9120 (C ₅₃ H ₂₀ D ₁₀ N ₄ , 732.3098) 1-487 m/z=738.9486 (C ₅₃ H ₁₄ D ₁₆ N ₄ , 738.3475) 1-488 m/z=753.0341 (C ₅₃ D ₃₀ N ₄ , 752.4353) 1-489 m/z=686.8799 (C ₄₈ H ₁₈ D ₉ N ₃ S, 686.2491) 1-490 m/z=704.9897 (C ₄₈ D ₂₇ N ₃ S, 704.3620) Preparation example 13. compound 2-102 preparation of Preparation example 13-1. compound 2-1-102 preparation of

N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-4-amine (15 g, 37.5 mmol/L) and trifluoromethanesulfonic acid (22.2 mL, 251.3 mmol/l) was dissolved in d ₆ -benzene (150 ml), and then the mixture was stirred at 60°C for 1 hour.

After that, methanol (MeOH) (200 mL) was added thereto, and the resultant was subjected to vacuum filtration to obtain Compound 2-1-102 (12.9 g, yield 82.1%). Preparation Example 13-2. Preparation of Compound 2-102

Compound 1-1-582 (12.9 g), compound A (10.0 g, 27.4 mmol/L) prepared in Preparation Example 1, tris(dibenzylideneacetone) dipalladium (Pd ₂ (dba) ₃ ) (1.3 g, 1.4 mmol/L), dicyclohexyl (2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (dicyclohexyl(2 ',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine, Xphos) (1.3 g, 1.4 mmol/L) and sodium tertiary butoxide (NaOtBu) (7.9 g , 82.2 mmol/l) was dissolved in xylene (140 ml), and then the mixture was refluxed for 1 hour.

After that, methanol (MeOH) (200 mL) was added thereto, and the resultant was subjected to vacuum filtration to obtain target compound 2-102 (yield 80.7%). Preparation Example 14. Preparation of Compound 2-103 Preparation Example 14-1. Preparation of Compound 2-3-103

_{Trifluoromethanesulfonic} acid (24.6 mL, 278.9 mmol/L), and then the mixture was stirred for 1 hour.

After the reaction was completed, methanol (200 mL) was introduced thereto to terminate the reaction, and Compound 2-3-103 (9.8 g, yield 94.4%) was obtained. Preparation Example 14-2. Preparation of Compound 2-2-103

Compound 2-3-103 (9.5 g, 39.2 mmol/L), aniline (3.7 g, 39.2 mmol/L), tris(dibenzylideneacetone) dipalladium (0) (Pd ₂ dba ₃ ) (1.8 g, 2.0 mmol/L), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (Sphos) (1.6 g, 3.9 mmol/L) and butyl Sodium alkoxide (NaOtBu) (7.5 g, 78.4 mmol/L) was dissolved in toluene (100 mL), and the mixture was then refluxed for 1 hour.

After the reaction was completed, the reaction material was purified by column chromatography (dichloromethane:hexane=1:3 (volume ratio)), and recrystallized with methanol to obtain compound 2-2- 103 (8.5 g, 85.2% yield). Preparation Example 14-3. Preparation of Compound 2-1-103

Compound 2-2-103 (8.5 g, 33.4 mmol/L), 1-bromo-4-iodobenzene (10.4 g, 36.7 mmol/L), palladium acetate (Pd(OAc) ₂ ) (0.4 g, 1.7 mmol/L), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene, Xantphos) (1.9 g, 3.3 mmol/L) and sodium tert-butoxide (NaOtBu) (6.4 g, 66.8 mmol/L) were dissolved in toluene (100 ml), and then the mixture was refluxed for 1 hour.

After the reaction was completed, the reaction material was purified by column chromatography (dichloromethane:hexane=1:4 (volume ratio)), and recrystallized with methanol to obtain compound 2-1- 103 (12.2 g, 89.2% yield). Preparation Example 14-4. Preparation of Compound 2-103

Compound A (10 g, 27.4 mmol/L), compound 2-1-103 (11.2 g, 27.4 mmol/L), tris(dibenzylideneacetone) dipalladium (0) (Pd ₂ dba ₃ ) (1.3 g, 1.4 mmol/L), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (Xphos) (1.3 g, 2.7 mmol/L) and sodium tert-butoxide (NaOtBu) (7.9 g, 82.2 mmol/L) were dissolved in xylene (120 ml), and then the mixture was refluxed for 1 hour.

After that, methanol (MeOH) (200 mL) was introduced thereto, and the resultant was subjected to vacuum filtration to obtain the target compound 2-103 (16.7 g, yield 88%). Preparation Example 15. Preparation of Compound 2-95

Compound A (10 g, 27.4 mmol/L), 3-iodo-1,1'-biphenyl (9.2 g, 32.9 mmol/L) prepared in Preparation Example 1, tri(dibenzyl Dipalladium (Pd ₂ (dba) ₃ ) (1.3 g, 1.4 mmol/L), dicyclohexyl (2',4',6'-triisopropyl-[1,1'- Phenyl]-2-yl)phosphine (Xphos) (1.3 g, 1.4 mmol/L) and sodium tert-butoxide (NaOtBu) (7.9 g, 82.2 mmol/L) were dissolved in xylene (140 mL) , and then the mixture was refluxed for 1 hour.

After that, methanol (MeOH) (200 mL) was added thereto, and the resultant was subjected to vacuum filtration to obtain Compound 2-95 (11.8 g, yield 83.2%).

As in Table 6 below, the target compound was prepared in the same manner as in Preparation Example 15, except that Intermediate E of Table 6 below was used instead of 3-iodo-1,1′-biphenyl. [Table 6] Compound number Intermediate E target compound yield 2-100 80.3% 2-105 87.5% Preparation Example 16. Preparation of Compound 2-104

After compound 2-105 (8.5 g, 13.2 mmol/L) was dissolved in benzene-d ₆ (90 mL), trifluoromethanesulfonic acid (7.6 mL, 85.8 mmol/L) was slowly added dropwise thereto liter), and then the mixture was stirred at a temperature of 80 °C for 1 h. After the reaction was completed, methanol (100 mL) was introduced thereto to terminate the reaction, and the target compound 2-104 (8.3 g, yield 93.2%) was obtained.

The synthesis results of the compounds described in Preparation Example 13 to Preparation Example 16 and Table 6 are shown in Table 7 and Table 8 below. In addition, the synthesis results of compounds corresponding to the heterocyclic compound of Chemical Formula 5 in the present disclosure are also shown in Table 7 and Table 8 below.

Table 7 below shows measured values of ¹ H NMR (CDCl ₃ , 300 MHz), and Table 8 below shows measured values of FD-mass spectrometry (FD-MS: Field Desorption Mass Spectrometry). [Table 7] compound ¹ H NMR (CDCl ₃ , 300 MHz) 2-95 δ=8.43~8.41(m, 4H), 8.21(s, 1H), 8.11~8.10(m, 4H), 7.94~7.88(m, 3H), 7.80~7.68(m, 5H), 7.49~4.45(m , 5H), 7.33~7.31(t, 1H) 2-100 δ=8.43~8.41(m, 4H), 8.11~8.10(m, 4H), 7.90~7.80(m, 6H), 7.69~7.68(d, 2H), 7.48~7.47(d, 1H), 7.33~7.24 (m, 12H), 7.00~6.99(t, 1H), 1.69(s, 6H) 2-103 δ=8.43~8.41(m, 4H), 8.11~8.10(m, 4H), 7.94~7.88(m, 3H), 7.80~7.79(d, 1H), 7.48~7.47(d, 1H), 7.33~7.32 (t, 1H) 2-104 δ=8.40~8.38(m, 4H), 8.05~8.02(m, 4H), 7.95~7.80(m, 4H), 7.69~7.68(d, 2H), 7.38~7.37(d, 1H), 7.33~7.25 (m, 5H), 7.08~7.07(d, 2H), 7.00~6.99(t, 1H) 2-105 δ=8.40~8.38(m, 4H), 8.05~8.02(m, 4H), 7.95~7.80(m, 4H), 7.75~7.65(m, 4H), 7.55~7.37(m, 8H), 7.33~7.25 (m, 5H), 7.08~7.07(d, 2H), 7.00~6.99(t, 1H) [Table 8] compound FD-Mass compound FD-Mass 2-1 m/z=532.6460 (C ₄₀ H ₂₄ N ₂ , 532.1939) 2-2 m/z=608.7440 (C ₄₆ H ₂₈ N ₂ , 608.2252) 2-3 m/z=658.8040 (C ₅₀ H ₃₀ N ₂ , 658.2409) 2-4 m/z=632.7660 (C ₄₈ H ₂₈ N ₂ , 632.2252) 2-5 m/z=638.7880 (C ₄₆ H ₂₆ N ₂ S, 638.1817) 2-6 m/z=622.7270 (C ₄₆ H ₂₆ N ₂ O, 622.2045) 2-7 m/z=697.8410 (C ₅₂ H ₃₁ N ₃ , 697.2518) 2-8 m/z=672.7870 (C ₅₀ H ₂₈ N ₂ O, 672.2202) 2-9 m/z=699.8570 (C ₅₂ H ₃₃ N ₃ , 699.2674) 2-10 m/z=749.9170 (C ₅₆ H ₃₅ N ₃ , 749.2831) 2-11 m/z=816.0200 (C ₆₁ H ₄₁ N ₃ , 815.3300) 2-12 m/z=775.9550 (C ₅₈ H ₃₇ N ₃ , 775.2987) 2-13 m/z=813.1808 (C ₅₈ D ₃₇ N ₃ , 812.5310) 2-14 m/z=835.1359 (C ₆₁ H ₂₂ D ₁₉ N ₃ , 834.4493) 2-15 m/z=457.5320 (C ₃₄ H ₁₉ NO, 457.1467) 2-16 m/z=507.5920 (C ₃₈ H ₂₁ NO, 507.1623) 2-17 m/z=533.6300 (C ₄₀ H ₂₃ NO, 533.1780) 2-18 m/z=609.7280 (C ₄₆ H ₂₇ NO, 609.2093) 2-19 m/z=557.6520 (C ₄₂ H ₂₃ NO, 557.1780) 2-20 m/z=624.7430 (C ₄₆ H ₂₈ N ₂ O, 624.2202) 2-21 m/z=700.8410 (C ₅₂ H ₃₂ N ₂ O, 700.2515) 2-22 m/z=776.9390 (C ₅₈ H ₃₆ N ₂ O, 776.2828) 2-23 m/z=817.0040 (C ₆₁ H ₄₀ N ₂ O, 816.3141) 2-24 m/z=714.8240 (C ₅₂ H ₃₀ N ₂ O ₂ , 714.2307) 2-25 m/z=714.9264 (C ₅₂ H ₁₈ D ₁₄ N ₂ O, 714.3393) 2-26 m/z=733.0363 (C ₅₂ D ₃₂ N ₂ O, 732.4523) 2-27 m/z=799.0732 (C ₅₈ H ₁₄ D ₂₂ N ₂ O, 798.4209) 2-28 m/z=473.5930 (C ₃₄ H ₁₉ NS, 473.1238) 2-29 m/z=549.6910 (C ₄₀ H ₂₃ NS, 549.1551) 2-30 m/z=640.8040 (C ₄₆ H ₂₈ N ₂ S, 640.1973) 2-31 m/z=716.9020 (C ₅₂ H ₃₂ N ₂ S, 716.2286) 2-32 m/z=756.9670 (C ₅₅ H ₃₆ N ₂ S, 756.2599) 2-33 m/z=833.0650 (C ₆₁ H ₄₀ N ₂ S, 832.2912) 2-34 m/z=563.7764 (C ₄₀ H ₉ D ₁₄ NS, 563.2430) 2-35 m/z=730.9874 (C ₅₂ H ₁₈ D ₁₄ N ₂ S, 730.3165) 2-36 m/z=749.0973 (C ₅₂ D ₃₂ N ₂ S, 748.4295) 2-37 m/z=483.6140(C ₃₇ H ₂₅ N, 483.1987) 2-38 m/z=533.6740(C ₄₁ H ₂₇ N, 533.2143) 2-39 m/z=589.7560(C ₄₃ H ₂₇ NS, 589.1864) 2-40 m/z=650.8250(C ₄₉ H ₃₄ N ₂ , 650.2722) 2-41 m/z=726.9230(C ₅₅ H ₃₈ N ₂ , 726.3035) 2-42 m/z=803.0210(C ₆₁ H ₄₂ N ₂ , 802.3348) 2-43 m/z=503.7360(C ₃₇ H ₅ D ₂ N, 503.3242) 2-44 m/z=765.1549(C ₅₅ D ₃₈ N ₂ , 764.5420) 2-45 m/z=532.6460 (C ₄₀ H ₂₄ N ₂ , 532.1939) 2-46 m/z=684.8420 (C ₅₂ H ₃₂ N ₂ , 684.2565) 2-47 m/z=760.9400 (C ₅₈ H ₃₆ N ₂ , 760.2878) 2-48 m/z=632.7660 (C ₄₈ H ₂₈ N ₂ , 632.2252) 2-49 m/z=699.8570 (C ₅₂ H ₃₃ N ₃ , 699.2674) 2-50 m/z=867.0680 (C ₆₄ H ₄₂ N ₄ , 866.3409) 2-51 m/z=775.9550 (C ₅₈ H ₃₇ N ₃ , 775.2987) 2-52 m/z=816.0200 (C ₆₁ H ₄₁ N ₃ , 815.3300) 2-53 m/z=551.7619 (C ₄₀ H ₅ D ₁₉ N ₂ , 551.3132) 2-54 m/z=795.0709 (C ₅₈ H ₁₈ D ₁₉ N ₃ , 794.4180) 2-55 m/z=457.5320 (C ₃₄ H ₁₉ NO, 457.1467) 2-56 m/z=507.5920 (C ₃₈ H ₂₁ NO, 507.1623) 2-57 m/z=563.6740 (C ₄₀ H ₂₁ NOS, 563.1344) 2-58 m/z=597.6730 (C ₄₄ H ₂₃ NO ₂ , 597.1729) 2-59 m/z=673.7710 (C ₅₀ H ₂₇ NO ₂ , 673.2042) 2-60 m/z=622.7270 (C ₄₆ H ₂₆ N ₂ O, 622.2045) 2-61 m/z=624.7430 (C ₄₆ H ₂₈ N ₂ O, 624.2202) 2-62 m/z=700.8410 (C ₅₂ H ₃₂ N ₂ O, 700.2515) 2-63 m/z=740.9060 (C ₅₅ H ₃₆ N ₂ O, 740.2828) 2-64 m/z=730.8850 (C ₅₂ H ₃₀ N ₂ OS, 730.2079) 2-65 m/z=471.6174 (C ₃₄ H ₅ D ₁₄ NO, 471.2345) 2-66 m/z=528.7201 (C ₃₈ D ₂₁ NO, 528.2941) 2-67 m/z=638.8284 (C ₄₆ H ₁₄ D ₁₄ N ₂ O, 638.3080) 2-68 m/z=733.0363 (C ₅₂ D ₃₂ N ₂ O, 732.4523) 2-69 m/z=473.5930 (C ₃₄ H ₁₉ NS, 473.1238) 2-70 m/z=523.6530 (C ₃₈ H ₂₁ NS, 523.1395) 2-71 m/z=623.7730 (C ₄₆ H ₂₅ NS, 623.1708) 2-72 m/z=549.6910 (C ₄₀ H ₂₃ NS, 549.1551) 2-73 m/z=640.8040 (C ₄₆ H ₂₈ N ₂ S, 640.1973) 2-74 m/z=716.9020 (C ₅₂ H ₃₂ N ₂ S, 716.2286) 2-75 m/z=716.9020 (C ₅₂ H ₃₂ N ₂ S, 716.2286) 2-76 m/z=756.9670 (C ₅₅ H ₃₆ N ₂ S, 756.2599) 2-77 m/z=563.7764 (C ₄₀ H ₉ D ₁₄ NS, 563.2430) 2-78 m/z=730.9874 (C ₅₂ H ₁₈ D ₁₄ N ₂ S, 730.3165) 2-79 m/z=749.0973 (C ₅₂ D ₃₂ N ₂ S, 748.4295) 2-80 m/z=483.6140(C ₃₇ H ₂₅ N, 483.1987) 2-81 m/z=559.7120(C ₄₃ H ₂₉ N, 559.2300) 2-82 m/z=589.7560(C ₄₃ H ₂₇ NS, 589.1864) 2-83 m/z=649.7930(C ₄₉ H ₃₁ NO, 649.2406) 2-84 m/z=533.6740(C ₄₁ H ₂₇ N, 533.2143) 2-85 m/z=609.7220(C ₄₇ H ₃₁ N, 609.2457) 2-86 m/z=573.6950(C ₄₃ H ₂₇ NO, 573.2093) 2-87 m/z=699.8530(C ₅₃ H ₃₃ NO, 699.2562) 2-88 m/z=650.8250(C ₄₉ H ₃₄ N ₂ , 650.2722) 2-89 m/z=700.8850(C ₅₃ H ₃₆ N ₂ , 700.2878) 2-90 m/z=726.9230(C ₅₅ H ₃₈ N ₂ , 726.3035) 2-91 m/z=766.9880(C ₅₈ H ₄₂ N ₂ , 766.3348) 2-92 m/z=655.932(C ₄₉ H ₁₃ D ₂₀ N, 655.3868) 2-93 m/z=765.1549(C ₅₅ D ₃₈ N ₂ , 764.5420) 2-94 m/z=441.5330(C ₃₄ H ₁₉ N, 441.1517) 2-95 m/z=517.6310(C ₄₀ H ₂₃ N, 517.1830) 2-96 m/z=606.7280(C ₄₆ H ₂₆ N ₂ , 606.2096) 2-97 m/z=682.8260(C ₅₂ H ₃₀ N ₂ , 682.2409) 2-98 m/z=608.7440(C ₄₆ H ₂₈ N ₂ , 608.2252) 2-99 m/z=760.9400(C ₅₈ H ₃₆ N ₂ , 760.2878) 2-100 m/z=724.9070(C ₅₅ H ₃₆ N ₂ , 724.2878) 2-101 m/z=531.7164(C ₄₀ H ₉ D ₁₄ N, 531.2709) 2-102 m/z=702.9518(C ₅₂ H ₁₄ D ₁₈ N ₂ , 702.3695) 2-103 m/z=693.8969 (C ₅₂ H ₂₃ D ₉ N ₂ , 693.3130) 2-104 m/z=717.0373 (C ₅₂ D ₃₂ N ₂ , 716.4574) 2-105 m/z=684.8420 (C ₅₂ H ₃₂ N ₂ , 684.2565) Experimental example 1. Experimental example 1-1. Production of organic light-emitting element

A glass substrate coated with a 1,500 angstrom thick ITO film was ultrasonically cleaned with distilled water. After cleaning with distilled water, the substrates were ultrasonically cleaned with solvents such as acetone, methanol, and isopropanol, dried, and then subjected to UV exposure in an ultraviolet (UV) cleaner. 5 minutes of ultraviolet ozone (ultraviolet ozone, UVO) treatment. After that, the substrate was transferred to a plasma cleaner (PT), and after undergoing plasma treatment under vacuum for the sake of ITO work function and to remove the residual film, the substrate was transferred to a thermal deposition device for for organic deposition.

Subsequently, the chamber was evacuated until the vacuum degree therein reached 10 ⁻⁶ Torr, and then 4,4′,4′′-tris[2-naphthyl ( phenyl)amino]triphenylamine (4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine, 2-TNATA) to deposit holes with a thickness of 600 angstroms on an ITO substrate Inject layer. The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (N,N'-bis( α-naphthyl)-N,N'-diphenyl-4,4'-diamine, NPB), and evaporated by applying an electric current to the cell to deposit a 300 angstrom thick Hole transport layer.

A light-emitting layer was thermally vacuum deposited thereon as described below. A light-emitting layer with a thickness of 400 angstroms was deposited by depositing the compounds described in Table 9 below as hosts and using (piq) ₂ (Ir)(acac) as the red phosphorescent dopant with 3 of the Ir compound. The host is doped in an amount of % by weight. Herein, as described in Table 9 below, a compound described as compound 1 was deposited, or a compound described as compound 1 was premixed with a compound described as compound 2 and then in a supply to deposit.

After that, 4,7-Diphenyl-1,10-phenanthroline (4,7-Diphenyl-1,10-phenanthroline, Bphen) was deposited with a thickness of 30 Å as a hole blocking layer, and Alq ₃ was deposited to a thickness of 250 angstroms as an electron transport layer. Finally, an electron injection layer was formed on the electron transport layer by depositing lithium fluoride (LiF) in a thickness of 10 Å, and then formed on the electron injection layer by depositing aluminum (Al) in a thickness of 1,200 Å. negative electrode, and thus, an organic electroluminescent (EL) element is manufactured.

Meanwhile, for each material to be used in OLED (Organic Light Emitting Element) manufacture, all organic compounds required for OLED manufacture were subjected to vacuum sublimation purification at 10 ^-8 Torr to 10 ^-6 Torr. Experimental Example 1-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Elements

For each of the organic light-emitting elements manufactured as above, electroluminescence (EL) properties were measured using M7000 manufactured by McScience Inc. The life measurement system (M6000) measures T ₉₀ when the standard luminance is 6,000 candela/square meter (cd/m ² ). The results of measuring the driving voltage, luminous efficiency, color coordinates (Commission Internationale de l´Eclairage, CIE) and lifetime of each of the organic light-emitting elements manufactured according to the present disclosure are shown in Table 9 below .

T ₉₀ means lifetime (unit: hour), that is, the time it takes for the brightness to become 90% relative to the initial brightness. [Table 9] Compound 1 Compound 2 Ratio (N:P) On (Volts) Driving Voltage (Volts) Efficiency (cd/area) Color coordinates (x, y) Lifetime (T ₉₀ ) Comparative example 1 A - - 3.20 5.38 25.10 (0.684, 0.316) 50 Comparative example 2 B - - 3.60 5.79 19.11 (0.684, 0.316) 100 Comparative example 3 C - - 3.52 5.70 19.88 (0.684.0.316) 110 Comparative example 4 D. - - 3.28 5.49 21.55 (0.685. 0.315) 40 Comparative Example 5 E. - - 3.28 5.50 15.50 (0.685, 0.315) 45 Comparative Example 6 f - - 3.29 5.50 20.50 (0.685, 0.315) 35 Example 1 1-3 - - 2.20 4.25 35.18 (0.685, 0.315) 100 Example 2 1-4 - - 2.21 4.24 35.55 (0.685, 0.315) 115 Example 3 1-20 - - 2.20 4.41 30.51 (0.685, 0.315) 85 Example 4 1-22 - - 2.25 4.35 38.11 (0.685, 0.315) 150 Example 5 1-363 - - 2.30 4.39 42.99 (0.685, 0.315) 210 Example 6 1-365 - - 2.37 4.50 35.10 (0.685, 0.315) 123 Example 7 1-374 - - 2.41 4.52 42.10 (0.685, 0.315) 300 Example 8 1-384 - - 2.45 4.62 35.11 (0.684.0.316) 150 Example 9 1-436 - - 2.61 4.50 43.10 (0.684.0.316) 250 Example 10 1-438 - - 2.59 4.47 45.15 (0.684.0.316) 370 Example 11 1-440 - - 2.65 4.60 35.90 (0.685, 0.315) 175 Example 12 1-441 - - 2.60 4.50 49.10 (0.685, 0.315) 350 Example 13 1-443 - - 2.62 4.54 48.50 (0.685, 0.315) 400 Example 14 1-446 - - 2.69 4.58 43.50 (0.685, 0.315) 510 Example 15 1-448 - - 2.73 4.71 37.20 (0.684.0.316) 280 Example 16 1-469 - - 2.51 4.30 55.15 (0.684.0.316) 150 Example 17 1-478 - - 2.52 4.33 62.50 (0.685, 0.315) 175 Example 18 1-469 2-100 3:1 2.52 4.47 60.15 (0.684.0.316) 210 Example 19 1-469 2-100 1:1 2.53 4.50 65.11 (0.685, 0.315) 410 Example 20 1-469 2-100 1:3 2.70 4.68 58.30 (0.685, 0.315) 305 Example 21 1-374 2-100 1:1 2.43 4.55 45.13 (0.685, 0.315) 640 Example 22 1-448 2-100 1:1 2.73 4.71 40.11 (0.685, 0.315) 400 Example 23 1-469 2-95 1:1 2.61 4.75 53.10 (0.684.0.316) 180 Example 24 1-469 2-102 1:1 2.57 4.59 64.99 (0.684.0.316) 520 Example 25 1-483 - - 2.61 4.48 45.10 (0.684.0.316) 410 Example 26 1-484 - - 2.60 4.48 45.13 (0.684.0.316) 415 Example 27 1-485 - - 2.61 4.49 45.16 (0.684.0.316) 490 Example 28 1-486 - - 2.53 4.35 62.48 (0.685, 0.315) 210 Example 29 1-488 - - 2.53 4.35 62.47 (0.685, 0.315) 250 Example 30 1-489 - - 2.31 4.40 42.89 (0.685, 0.315) 240 Example 31 1-490 - - 2.31 4.42 42.80 (0.685, 0.315) 285 Example 32 1-469 2-105 1:1 2.55 4.55 65.15 (0.684.0.316) 410 Example 33 1-469 2-104 1:1 2.58 4.61 64.85 (0.684.0.316) 580 Example 34 1-488 2-105 - 2.55 4.38 68.11 (0.684.0.316) 460 Example 35 1-488 2-104 1:1 2.58 4.41 67.90 (0.685, 0.315) 620 [compare compound] Experimental example 2. Experimental example 2-1. Manufacture of organic light-emitting element

A glass substrate coated with a 1,500 angstrom thick ITO film was ultrasonically cleaned with distilled water. After cleaning with distilled water, the substrates were ultrasonically cleaned with solvents such as acetone, methanol, and isopropanol, dried, and subjected to 5 minutes of UVO (ultraviolet light) in a UV cleaner. ozone) disposal. After that, the substrate was transferred to a plasma cleaner (PT), and after undergoing plasma treatment under vacuum for the sake of ITO work function and to remove the residual film, the substrate was transferred to a thermal deposition device for for organic deposition.

On the transparent ITO electrode (positive electrode), as a common layer, 4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA) is formed as a hole Injection layer, forming N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) as hole transport layer, and forming cyclohexylene bis [N,N-bis(4-methylphenyl)aniline] (cyclohexylidenebis[N,N-bis(4-methylphenyl)benzonamine], TAPC) acts as an electron blocking layer or forms a tris(4-carbazolyl-9 -ylphenyl)amine (tris(4-carbazoyl-9-ylphenyl)amine, TCTA) was used as the exciton blocking layer.

A light-emitting layer was thermally vacuum deposited thereon as described below. The emissive layer was deposited to a thickness of 400 Angstroms by depositing the compounds described in Table 10 below as the red host in one or two supplies and using (piq) ₂ (Ir)(acac) as the red Phosphorescent dopant doped the host in an amount of 3% by weight of the Ir compound. Herein, as described in Table 10 below, a compound described as compound 1 was deposited, or a compound described as compound 1 was premixed with a compound described as compound 2 and then in a supply to deposit.

After that, Bphen was deposited to a thickness of 30 Å as a hole blocking layer, and 1,3,5-tris(1-phenyl-1H-benzimidazole-2 -yl)benzene (1,3,5-Tris(1-phenyl-1H-benzimidazol-2-yl)benzene, TPBI) as the electron transport layer. Finally, an electron injection layer was formed on the electron transport layer by depositing lithium fluoride (LiF) in a thickness of 10 Å, and then formed on the electron injection layer by depositing aluminum (Al) in a thickness of 1,200 Å. negative electrode, and thus, an organic electroluminescence element was fabricated.

Meanwhile, for each material to be used in OLED (Organic Light Emitting Element) manufacture, all organic compounds required for OLED manufacture were subjected to vacuum sublimation purification at 10 ^-8 Torr to 10 ^-6 Torr. Experimental Example 2-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Devices

For each of the organic light-emitting elements manufactured as above, electroluminescence (EL) properties were measured using M7000 manufactured by Mike Science Corporation, and the measurement results were measured by a lifetime measurement system manufactured by Mike Science Corporation ( M6000) measured T ₉₀ at a standard luminance of 6,000 cd/m². The results of measuring the driving voltage, luminous efficiency, color coordinate (CIE) and lifetime of each of the organic light emitting elements manufactured according to the present disclosure are shown in Table 10 below.

T ₉₀ means lifetime (unit: hour), that is, the time it takes for the brightness to become 90% relative to the initial brightness. [Table 10] Compound 1 Compound 2 Ratio (N:P) On (Volts) Driving Voltage (Volts) Efficiency (cd/area) Color coordinates (x, y) Lifetime (T ₉₀ ) Comparative Example 7 A - - 3.22 5.39 22.30 (0.684, 0.316) 70 Comparative Example 8 B - - 3.67 5.83 23.55 (0.685, 0.315) 122 Comparative Example 9 C - - 3.66 5.78 24.15 (0.684.0.316) 130 Example 36 1-3 - - 2.22 4.40 38.28 (0.685, 0.315) 110 Example 37 1-4 - - 2.22 4.44 38.55 (0.685, 0.315) 130 Example 38 1-363 - - 2.33 4.51 43.85 (0.685, 0.315) 250 Example 39 1-436 - - 2.62 4.61 45.10 (0.684.0.316) 250 Example 40 1-438 - - 2.60 4.58 46.15 (0.684.0.316) 400 Example 41 1-469 - - 2.53 4.50 60.11 (0.684.0.316) 210 Example 42 1-478 - - 2.54 4.55 65.50 (0.685, 0.315) 255 Example 43 1-483 - - 2.63 4.51 48.11 (0.684.0.316) 490 Example 44 1-484 - - 2.64 4.52 47.50 (0.684.0.316) 495 Example 45 1-485 - - 2.66 4.56 46.90 (0.684.0.316) 580 Example 46 1-469 2-100 1:3 2.71 4.70 58.20 (0.685, 0.315) 425 Example 47 1-469 2-100 1:1 2.55 4.55 66.12 (0.685, 0.315) 630 Example 48 1-469 2-100 3:1 2.54 4.52 61.15 (0.684.0.316) 250 Example 49 1-469 2-105 1:1 2.57 4.59 64.55 (0.684.0.316) 680 Example 50 1-469 2-104 1:1 2.58 4.69 63.15 (0.684.0.316) 860 [compare compound]

The heterocyclic compound represented by Chemical Formula 1 of the present disclosure has high thermal stability. In addition, the molecular weight of the heterocyclic compound is easily controlled to a target level due to expansion of aromaticity, and a host material with an appropriate band gap can be easily designed. A proper bandgap of the light emitting layer enables superior hole transport capability and prevents electron loss, which may contribute to efficient formation of recombination zones. Therefore, as seen in the results shown in Tables 9 and 10, it was recognized that the heterocyclic compound represented by Chemical Formula 1 of the present disclosure showed improved potency compared to the comparative example.

Specifically, it is seen that when a donor having desirable hole-transporting ability (compound 2 (p-host) shown in Table 9 and Table 10, the heterocyclic compound of Chemical Formula 5 of the present disclosure) having desirable hole transport ability and a donor having When acceptors with satisfactory electron transport capabilities (compound 1 (n-host) shown in Table 9 and Table 10, the heterocyclic compound of Chemical Formula 1 disclosed in this disclosure) are used as the host of the light-emitting layer, electron injection and hole injection are enhanced, and Organic light emitting devices have enhanced efficiency and lifetime by efficiently forming recombination regions.

In addition, the organic light-emitting device of Experimental Example 2 further includes an electron blocking layer, and compared with the results of Experimental Example 1, better results are obtained, because the inclusion of an electron blocking layer can enhance the device by preventing electron loss nature of life.

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

1 to 3 are diagrams each schematically showing a stacked structure of an organic light emitting element according to an embodiment of the present disclosure.

100: Substrate

200: positive electrode

300: organic material layer

400: negative electrode

Claims (18)

A heterocyclic compound represented by the following Chemical Formula 1: [Chemical Formula 1] Wherein, in Chemical Formula 1, R1 to R10 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; 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 ring Alkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O )R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 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; R11 is the following chemical formula 2; [chemical formula 2] In Chemical Formula 2, L1 is a direct bond; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl; m is an integer of 0 to 5, and when When m is 2 or greater than 2, L1 are the same or different from each other; and N-Het is a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heterocyclic group including two or more Ns; and * is connected to the point of the following chemical formula 3, [chemical formula 3] X1 is NRa; O; S; CRbRc; or a direct bond; and Ra, Rb, Rc, and R21 to R24 are the same or different from each other, and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; 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 alkane Oxygen; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted -P(=O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 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. The heterocyclic compound as claimed in claim 1, wherein, when N-Het has a substituent, the substituent is deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl. The heterocyclic compound as described in Claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formula 1-1 and Chemical Formula 1-2: [Chemical Formula 1-1] [chemical formula 1-2] In Chemical Formula 1-1 and Chemical Formula 1-2, R1 to R10 have the same definition as in Chemical Formula 1; R11 has the same definition as in Chemical Formula 2; and X1 and R21 to R24 have the same definition as in Chemical Formula 3. The heterocyclic compound as described in Claim 1, wherein Chemical Formula 2 is represented by the following Chemical Formula 4: [Chemical Formula 4] In Chemical Formula 4, X11 to X15 are the same or different from each other, and are each independently N; or CRd; at least two or more of X11 to X15 are N; when there are two or more CRd, Rd are the same as each other or different; Rd is selected from the group consisting of hydrogen; deuterium; halogen; 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 heterocycle Alkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)R101R102; -SiR101R102R103; Two or more groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 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; and L1 and m has the same definition as in Chemical Formula 2. The heterocyclic compound as described in Claim 4, wherein Chemical Formula 4 is represented by any one of the following Chemical Formula 4-1 to Chemical Formula 4-4: [Chemical Formula 4-1] [chemical formula 4-2] [chemical formula 4-3] [chemical formula 4-4] In Chemical Formula 4-1 to Chemical Formula 4-4, R31 to R43 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; 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)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or substituted or Unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 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 aromatic or a substituted or unsubstituted C2 to C60 heteroaryl group; and L1 and m have the same definitions as in Chemical Formula 2. The heterocyclic compound as described in Claim 5, wherein Chemical Formula 4-2 is represented by any one of the following Chemical Formula 4-2-1 to Chemical Formula 4-2-3: [Chemical Formula 4-2-1] [Chemical formula 4-2-2] [chemical formula 4-2-3] In Chemical Formula 4-2-1 to Chemical Formula 4-2-3, Y is O; or S; R44 to R56 are the same or different from each other, and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyanogen 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 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 -P(=O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 are the same or different from each other, and are each independently substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; and L1 and m have the same definitions as in Chemical Formula 2. The heterocyclic compound according to claim 1, wherein the compound represented by Chemical Formula 1 does not contain deuterium as a substituent, or has a deuterium content of 1% to 100% based on the total number of hydrogen atoms and deuterium atoms. 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 opposite the first electrode; and one or more layers of organic material disposed between the first electrode and the second electrode, Wherein one or more layers of the organic material layers comprise the heterocyclic compound as described in any one of Claim 1 to Claim 8. The organic light-emitting device according to claim 9, 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 9, 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 element as claimed in item 9, wherein the organic material layer further comprises a heterocyclic compound represented by the following chemical formula 5: [chemical formula 5] In Chemical Formula 5, R61 to R70 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; 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)R101R102 ; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 Heterocyclic ring, wherein R101, R102 and R103 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 Substituted C2 to C60 heteroaryl; R71 is a substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; or the following chemical formula 6; when the heteroaryl When the heteroatom is N, including a heteroatom; [chemical formula 6] In Chemical Formula 6, L2 is a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl; n is an integer from 1 to 5, and when n is 2 or greater than 2, L2 is the same or different from each other; and Ar1 and Ar2 are the same or different from each other, and are each independently substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 hetero aryl; and * is the point of attachment to the following chemical formula 7, [chemical formula 7] X2 is NRe; O; S; CRfRg; or a direct bond; and Re, Rf, Rg, and R81 to R84 are the same or different from each other, and are each independently selected from the group consisting of: hydrogen; deuterium; 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 alkane Oxygen; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted -P(=O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 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. The organic light-emitting device according to claim 12, wherein the heterocyclic compound represented by Chemical Formula 5 does not contain deuterium as a substituent, or has a deuterium content of 1% to 100% based on the sum of hydrogen atoms and deuterium atoms. The organic light-emitting element as claimed in claim 12, wherein at least one of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 does not contain deuterium as a substituent, or a hydrogen atom and The total number of deuterium atoms has a deuterium content of 1% to 100%. The organic light-emitting element as claimed in item 12, wherein the heterocyclic compound represented by Chemical Formula 5 is any one selected from the following compounds: . The organic light-emitting device as claimed in claim 9, 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, two layers, or more layers. A composition for an organic material layer of an organic light-emitting element, the composition comprising: a heterocyclic compound as described in any one of claim 1 to claim 8; and a heterocyclic compound represented by the following chemical formula 5: [chemical formula 5] Wherein, in Chemical Formula 5, R61 to R70 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; 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 ring Alkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O )R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 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; R71 is substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; or the following chemical formula 6; when the hetero When the heteroatom of the aryl group is N, one heteroatom is included; [Chemical Formula 6] In Chemical Formula 6, L2 is a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl; n is an integer from 1 to 5, and when n is 2 or greater than 2, L2 is the same or different from each other; and Ar1 and Ar2 are the same or different from each other, and are each independently substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 hetero aryl; and * is the point of attachment to the following chemical formula 7, [chemical formula 7] X2 is NRe; O; S; CRfRg; or a direct bond; and Re, Rf, Rg, and R81 to R84 are the same or different from each other, and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; 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 alkane Oxygen; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted -P(=O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 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. The composition according to claim 17, wherein the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 have a weight ratio of 1:10 to 10:1.

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