KR20230016901A - Heterocyclic compound, organic light emitting device comprising the same, manufacturing method of the same and composition for organic layer of organic light emitting device - Google Patents

Abstract

The present specification relates to a heterocyclic compound represented by chemical formula 1, an organic light emitting device including the same, a method for manufacturing the same, and a composition for an organic material layer. When the compound represented by chemical formula 1 is used in the organic material layer, the driving voltage of the organic light emitting device can be lowered, and the luminous efficiency and the lifespan characteristics of the organic light emitting device can be improved.

Description

Heterocyclic compound, an organic light emitting device including the same, a method for preparing the same, and a composition for an organic material layer

The present invention relates to a heterocyclic compound, an organic light emitting device including the same, a method for preparing the same, and a composition for an organic material layer.

An organic light emitting device is a type of self-luminous display device, and has advantages such as a wide viewing angle, excellent contrast, and fast response speed.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes are combined in the organic thin film to form a pair, and then emit light while disappearing. The organic thin film may be composed of a single layer or multiple layers as needed.

The material of the organic thin film may have a light emitting function as needed. For example, as the organic thin film material, a compound capable of constituting the light emitting layer by itself may be used, or a compound capable of serving as a host or dopant of the host-dopant type light emitting layer may be used. In addition, as a material for the organic thin film, a compound capable of performing functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.

In order to improve the performance, lifespan or efficiency of organic light emitting devices, the development of materials for organic thin films is continuously required.

US Patent No. 4,356,429

The present invention is to provide a heterocyclic compound, an organic light emitting device including the same, a method for preparing the same, and a composition for an organic layer.

The present invention provides a heterocyclic compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

X1 to X3 are the same as or different from each other, and are each independently CRa or N,

R1 and Ra are the same as or different from each other, and are hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; And -NR101R102, or two or more groups adjacent to each other combine to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and are each independently 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 heteroaryl group, and when R1 or Ra is plural, each R1 or Ra is the same as or different from each other,

Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms,

L1 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; A substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms, l is an integer of 1 to 3, and when l is 2 or more, each L1 is the same as or different from each other,

Ring A and ring B are the same as or different from each other, and are each independently a substituted or unsubstituted aryl ring having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl ring having 5 to 60 carbon atoms,

m is an integer from 0 to 8, and when m is 2 or more, each R1 is the same as or different from each other.

In addition, the present invention, the first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the heterocyclic compound represented by Chemical Formula 1. provides

In addition, the present invention provides an organic light emitting device in which the organic material layer further includes a heterocyclic compound represented by Chemical Formula 2 below.

[Formula 2]

In Formula 2,

X21 and X22 are the same as or different from each other, and are each independently O or S,

R31 to R39 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; And -NR101R102, or two or more groups adjacent to each other combine to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and are each independently 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 heteroaryl group,

L2 is a direct bond, substituted or unsubstituted arylene group having 6 to 60 carbon atoms; A substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms, o is an integer of 1 to 3, and when o is 2 or more, each L2 is the same as or different from each other,

Z is any one of the following formulas 2-1 to 2-5,

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

In Formulas 2-1 to 2-5,

Ar3 to Ar5 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms,

R41 to R58 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; and -NR101R102, wherein R101, R102, and R103 are the same as or different from each other, and each independently 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 heteroaryl group,

p1 and p2 are the same as or different from each other, and are each independently an integer of 0 to 2, when p1 is 2, R49 is the same as or different from each other, and when n2 is 2, R54 is the same as or different from each other.

In addition, the present invention provides a composition for an organic material layer of an organic light emitting device including the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2.

The compounds described in this specification can be used as a material for an organic material layer of an organic light emitting device. The compound may serve as a hole injection layer material, a hole transport layer material, a light emitting layer material, an electron transport layer material, or an electron injection layer material in an organic light emitting device. In particular, the compound may be used as a material for a light emitting layer of an organic light emitting device.

Specifically, the compound may be used alone as a light emitting material, or may be used as a host material or a dopant material of a light emitting layer. When the compound represented by Chemical Formula 1 is used in the organic material layer, the driving voltage of the organic light emitting device can be lowered, the light emitting efficiency can be improved, and the lifetime characteristics can be improved.

1 to 4 are diagrams schematically illustrating a stacked structure of an organic light emitting device according to an exemplary embodiment of the present invention.

Hereinafter, this application will be described in detail.

In the present specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the hydrogen atom is substituted, that is, the position where the substituent is substituted , When two or more substituents are substituted, two or more substituents may be the same as or different from each other.

In the present specification, "substituted or unsubstituted" refers to C1 to C60 straight-chain or branched-chain alkyl; C2 to C60 straight or branched alkenyl; C2 to C60 straight or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P(=O)RR'; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine selected from the group consisting of It means substituted or unsubstituted with one or more substituents, or substituted or unsubstituted with a substituent in which two or more substituents selected from the substituents exemplified above are connected.

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

In the present specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by 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 include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, etc., but is not limited thereto.

In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40, and more specifically, 2 to 20. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1 -butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but is not limited thereto.

In the present specification, the alkynyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted by 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 the present specification, the alkoxy group may be straight chain, branched chain or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It is not limited.

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic means a group in which a cycloalkyl group is directly connected or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, and the like. The number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2 ,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but are not limited thereto.

In the present specification, the heterocycloalkyl group includes O, S, Se, N or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic means a group in which a heterocycloalkyl group is directly connected or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, and the like. The heterocycloalkyl group may have 2 to 60, specifically 2 to 40, and more specifically 3 to 20 carbon atoms.

In the present specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic means a group in which an aryl group is directly connected or condensed with another cyclic group. Here, the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, and the like. The aryl group may include a spiro group. 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 the aryl group include a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, and a pyrene group. Nyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof and the like, but is not limited thereto.

In the present specification, the phosphine oxide group is represented by -P(=0)R ₁₀₁ R ₁₀₂ , R ₁₀₁ and R ₁₀₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. Specifically, it may be substituted with an aryl group, and the above-described examples may be applied to the aryl group. For example, the phosphine oxide group includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.

In the present specification, a silyl group includes Si and is a substituent to which the Si atom is directly connected as a radical, represented by -SiR ₁₀₄ R ₁₀₅ R ₁₀₆ , R ₁₀₄ to R ₁₀₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. Specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. It is not limited.

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

,

,

,

,

,

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

,

,

,

,

,

etc., but is not limited thereto.

In the present specification, the spiro group is a group including a spiro structure, and may have 15 to 60 carbon atoms. For example, the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro bonded to a fluorenyl group. Specifically, the following spiro group may include any one of groups of the following structural formula.

In the present specification, the heteroaryl group includes S, O, Se, N or Si as a hetero atom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic means a group in which a heteroaryl group is directly connected or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, and the like. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40, and more specifically 3 to 25 carbon atoms. Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, and a thiazolyl group. group, isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolilyl group, naphthyridyl group, acridinyl group, phenanthridi Nyl group, imidazopyridinyl group, diazanaphthalenyl group, triazaindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group , Dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilol group, spirobi (dibenzosilol), dihydrophenazinyl group, A phenoxazinyl group, a phenanthridyl group, an imidazopyridinyl group, a thienyl group, an indolo[2,3-a]carbazolyl group, an indolo[2,3-b]carbazolyl group, an indolinyl group, 10, 11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenantrazinyl group, phenothiathiazinyl group, phthalazinyl group, naphthyridinyl group, phenanthrolinyl group, Benzo [c] [1,2,5] thiadiazolyl group, 5,10-dihydrodibenzo [b, e] [1,4] azasilinyl group, pyrazolo [1,5-c] quinazolinyl group , pyrido [1,2-b] indazolyl group, pyrido [1,2-a] imidazo [1,2-e] indolinyl group, 5,11-dihydroindeno [1,2-b ] carbazolyl group and the like, but is not limited thereto.

In the present specification, the amine group is a monoalkylamine group; monoarylamine group; Monoheteroarylamine group; -NH ₂ ; Dialkylamine group; Diaryl amine group; Diheteroarylamine group; an alkyl arylamine group; Alkylheteroarylamine group; And it may be selected from the group consisting of an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorene Examples include a ylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but are not limited thereto.

In the present specification, the arylene group means that the aryl group has two bonding sites, that is, a divalent group. The description of the aryl group described above can be applied except that each is a divalent group. In addition, the heteroarylene group means a heteroaryl group having two bonding sites, that is, a divalent group. The above description of the heteroaryl group may be applied except that each is a divalent group.

As used herein, "adjacent" refers to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. can 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 interpreted as “adjacent” to each other.

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

In the present specification, "when no substituent is shown in the chemical formula or compound structure" may mean that all positions where the substituent can come are hydrogen or deuterium. That is, deuterium is an isotope of hydrogen, and some hydrogen atoms may be an isotope of deuterium, and in this case, the content of deuterium may be 0% to 100%.

In the present specification, in "when no substituent is shown in the chemical formula or compound structure", deuterium is explicitly specified, such as "the content of deuterium is 0%", "the content of hydrogen is 100%", and "all substituents are hydrogen" If not excluded, hydrogen and deuterium may be mixed and used in the compound.

In the present specification, deuterium is one of the isotopes of hydrogen, and is an element having a deuteron composed of one proton and one neutron as an atomic nucleus, and is represented by hydrogen-2. The element symbol can also be written as D or 2H.

In the present specification, isotopes, which mean atoms having the same atomic number (Z) but different mass numbers (A), have the same number of protons, but have the same number of neutrons. It can also be interpreted as elements with different numbers.

In the present specification, the meaning of the content T% of a specific substituent is defined as T1 for the total number of substituents that the base compound may have, and when the number of specific substituents among them is defined as T2, T2/T1× It can be defined as 100 = T%.

로 표시되는 페닐기에 있어서 중수소의 함량 20%라는 것은 페닐기가 가질 수 있는 치환기의 총 개수는 5(식 중 T1)개이고, 그 중 중수소의 개수가 1(식 중 T2)인 경우를 의미할 수 있다. 즉, 페닐기에 있어서 중수소의 함량이 20%인 것은 하기 구조식과 같이 표시될 수 있다.That is, in one example,

In the phenyl group represented by 20% of the deuterium content 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 is 1 (T2 in the formula) . That is, in the phenyl group, the deuterium content of 20% can be represented by the following structural formula.

In addition, in the present specification, in the case of "a phenyl group having a deuterium content of 0%", it may mean a phenyl group that does not contain deuterium atoms, that is, has 5 hydrogen atoms.

In the present invention, the C6 to C60 aromatic hydrocarbon ring means a compound containing an aromatic ring composed of C6 to C60 carbons and hydrogen, for example, benzene, biphenyl, triphenyl, triphenylene, naphthalene, Anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, etc. may be mentioned, but is not limited thereto, and an aromatic hydrocarbon ring compound known in the art as having the above number of carbon atoms may be used. All inclusive.

The present invention provides a heterocyclic compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

X1 to X3 are the same as or different from each other, and are each independently CRa or N,

R1 and Ra are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; -P(=0)R101R102; -SiR101R102R103; And -NR101R102, or two or more groups adjacent to each other combine to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and are each independently 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 heteroaryl group, and when R1 or Ra is plural, each R1 or Ra is the same as or different from each other,

Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms,

L1 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms, l is an integer of 1 to 3, and when l is 2 or more, each L1 is the same as or different from each other,

Ring A and ring B are the same as or different from each other, and are each independently a substituted or unsubstituted aryl ring having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl ring having 5 to 60 carbon atoms,

m is an integer from 0 to 8, and when m is 2 or more, each R1 is the same as or different from each other.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 may include 1 or more and 50 or less deuterium as a substituent.

In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 may include 1 or more and 40 or less deuterium atoms as substituents.

In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 may include 5 or more and 40 or less deuterium atoms as substituents.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 may have a deuterium content of 1 to 100% with respect to the total number of hydrogen atoms and deuterium atoms in the substituents.

In another embodiment of the present invention, the heterocyclic compound represented by Formula 1 may have a deuterium content of 20 to 90% based on the total number of hydrogen atoms and deuterium atoms in the substituents.

In another embodiment of the present invention, in the heterocyclic compound represented by Formula 1, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituents may be 40 to 80%. The represented hetero compound may have a deuterium content of 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, 50% or more, relative to the total number of hydrogen atoms and deuterium atoms in the substituent, 100% or less, It may be 90% or less, 80% or less, 70% or less, or 60% or less.

(이하, '화학식 1-1'이라고 함)은 하기 화학식 1-1-1 내지 화학식 1-1-2 중 어느 하나일 수 있다. In one embodiment of the present invention, in Formula 1

(Hereinafter, referred to as 'Formula 1-1') may be any one of the following Chemical Formulas 1-1-1 to 1-1-2.

[Formula 1-1-1]

[Formula 1-1-2]

[Formula 1-1-3]

In Formulas 1-1-1 to Formulas 1-1-3,

Ar1, Ar2, X1 and X3 are the same as defined in Formula 1 above.

In one embodiment of the present invention, Chemical Formulas 1-1-1 to Chemical Formulas 1-1-3 may include 0 or more and 20 or less deuterium atoms as substituents.

In another embodiment of the present invention, Chemical Formulas 1-1-1 to Chemical Formulas 1-1-3 may include 0 or more and 18 or less deuterium atoms as substituents.

In another embodiment of the present invention, Formula 1-1-1 to Formula 1-1-3 may include 5 or more and 18 or less deuterium atoms as substituents.

In one embodiment of the present invention, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituents in Chemical Formulas 1-1-1 to 1-1-3 may be 0 to 100%.

In another embodiment of the present invention, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituents in Chemical Formulas 1-1-1 to 1-1-3 may be 20 to 90%.

In another embodiment of the present invention, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituents in Chemical Formulas 1-1-1 to 1-1-3 may be 40 to 80%.

For example, in Chemical Formulas 1-1-1 to 1-1-3, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituent is 0% or more, 1% or more, 10% or more, 20% or more, It may be 30% or more, 40% or more, 50% or more, 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

In one embodiment of the present invention, L1 is a substituted or unsubstituted C6 to C30 arylene group; Or it may be a substituted or unsubstituted C6 to C30 heteroarylene group, and when l is 2 or more, each L1 may be the same as or different from each other.

In another embodiment of the present invention, L1 is a substituted or unsubstituted C6 to C20 arylene group; Or it may be a substituted or unsubstituted C6 to C20 heteroarylene group, and when l is 2 or more, each L1 may be the same as or different from each other.

In another embodiment of the present invention, L1 is a substituted or unsubstituted phenylene group; Or it may be a naphthylene group, and when l is 2 or more, each L 1 may be the same as or different from each other.

Specific examples of L1 are shown below, but are not limited to these examples.

In one embodiment of the present invention, the L1 may include 0 or more and 20 or less deuterium as a substituent.

In another embodiment of the present invention, the L1 may include 0 or more and 10 or less deuterium as a substituent.

In one embodiment of the present invention, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituent L1 may be 0 to 100%.

In another embodiment of the present invention, the L1 may have a deuterium content of 20 to 90% with respect to the total number of hydrogen atoms and deuterium atoms in the substituent.

In another embodiment of the present invention, the L1 may have a deuterium content of 40 to 80% with respect to the total number of hydrogen atoms and deuterium atoms in the substituent.

For example, in L1, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituent may be 0% or more, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more. and may be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

(이하, '화학식 1-2'라 함)은 하기 화학식 1-2-1 내지 화학식 1-2-3 중 어느 하나일 수 있다. In one embodiment of the present invention, in Formula 1

(Hereinafter referred to as 'Formula 1-2') may be any one of the following Chemical Formulas 1-2-1 to 1-2-3.

[Formula 1-2-1]

[Formula 1-2-2]

[Formula 1-2-3]

In Formulas 1-2-1 to Formulas 1-2-3,

R11 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; and -NR101R102, wherein R101, R102, and R103 are the same as or different from each other, and each independently 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 heteroaryl group,

n1 and n2 are the same as or different from each other, and are each independently an integer of 0 to 2, when n1 is 2, R19 is the same as or different from each other, and when n2 is 2 or more, R24 is the same as or different from each other.

In one embodiment of the present invention, the heterocyclic compound represented by any one of Formulas 1-2-1 to 1-2-3 in Formula 1-2 contains 0 or more and 20 or less deuterium atoms as substituents. can do.

In another embodiment of the present invention, the heterocyclic compound represented by any one of Formulas 1-2-1 to 1-2-3 in Formula 1-2 contains 0 or more and 12 or less deuterium atoms as substituents. can do.

In another embodiment of the present invention, the heterocyclic compound represented by any one of Formulas 1-2-1 to 1-2-3 in Formula 1-2 contains 8 or more and 12 or less deuterium atoms as substituents. can do.

In one embodiment of the present invention, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituents in Chemical Formula 1-2 may be 0 to 100%.

In another embodiment of the present invention, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituents in Chemical Formula 1-2 may be 20 to 90%.

In another embodiment of the present invention, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituents in Chemical Formula 1-2 may be 40 to 80%.

For example, in Formula 1-2, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituent is 0% or more, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, 50% or more % or more, 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

In one embodiment of the present invention, the R11 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C2 to C30 alkenyl group; A substituted or unsubstituted C2 to C30 alkynyl group; A substituted or unsubstituted C1 to C30 alkoxy group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C2 to C30 heterocycloalkyl group; A substituted or unsubstituted C6 to C30 aryl group; A substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; and -NR101R102, wherein R101, R102, and R103 are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.

In another embodiment of the present invention, the R11 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.

In another embodiment of the present invention, the R11 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.

In another embodiment of the present invention, the R11 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; It may be a substituted or unsubstituted phenyl group, biphenyl group, or naphthyl group.

In one embodiment of the present invention, the compound represented by Formula 1-2-2 may be a compound represented by any one of Formulas 1-2-2-a to Formula 1-2-2-c.

[Formula 1-2-2-a]

[Formula 1-2-2-b]

[Formula 1-2-2-c]

In Formulas 1-2-2-a to Formulas 1-2-2-c,

R11 to R14, R19 to R23 and n1 have the same definitions as in Formula 1-2-2.

In one embodiment of the present invention, Chemical Formulas 1-2-2-a to Chemical Formulas 1-2-2-c may include 0 or more and 20 or less deuterium atoms as substituents.

In another embodiment of the present invention, Formula 1-2 and Formula 1-2-2-a to Formula 1-2-2-c may include 1 or more and 18 or less deuterium atoms as substituents.

In one embodiment of the present invention, in Formula 1-2-2-a to Formula 1-2-2-c, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituents may be 0 to 100%. .

In another embodiment of the present invention, in Formula 1-2-2-a to Formula 1-2-2-c, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituents may be 20 to 90%. .

In another embodiment of the present invention, in Formula 1-2-2-a to Formula 1-2-2-c, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituents may be 40 to 80%. .

For example, in Formula 1-2-2-a to Formula 1-2-2-c, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituent is 0% or more, 1% or more, 10% or more, It may be 20% or more, 30% or more, 40% or more, 50% or more, 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

In one embodiment of the present invention, R11 to R14 and R19 to R23 in Formulas 1-2-2-a to Formula 1-2-2-c are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C2 to C30 alkenyl group; A substituted or unsubstituted C2 to C30 alkynyl group; A substituted or unsubstituted C1 to C30 alkoxy group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C2 to C30 heterocycloalkyl group; A substituted or unsubstituted C6 to C30 aryl group; A substituted or unsubstituted C2 to C30 heteroaryl group; -P(=0)R101R102; -SiR101R102R103; and -NR101R102, wherein R101, R102, and R103 are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group, n1 may be an integer of 0 to 2, and when n1 is 2, R19 may be the same as or different from each other.

In another embodiment of the present invention, R11 to R14 and R19 to R23 in Formulas 1-2-2-a to Formula 1-2-2-c are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group, n1 may be an integer of 0 to 2, and when n1 is 2, R19 may be the same as or different from each other.

In another embodiment of the present invention, R11 to R14 and R19 to R23 in Formulas 1-2-2-a to Formula 1-2-2-c are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group, n1 may be an integer of 0 to 2, and when n1 is 2, R19 may be the same as or different from each other.

In another embodiment of the present invention, R11 to R14 and R19 to R23 in Formulas 1-2-2-a to Formula 1-2-2-c are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; It may be a substituted or unsubstituted phenyl group, biphenyl group, or naphthyl group, n1 may be an integer of 0 to 2, and when n1 is 2, R19 may be the same as or different from each other.

In one embodiment of the present invention, the compound represented by Formula 1-2-3 may be a compound represented by any one of Formulas 1-2-3-a to Formula 1-2-3-e.

[Formula 1-2-3-a]

[Formula 1-2-3-b]

[Formula 1-2-3-c]

[Formula 1-2-3-d]

[Formula 1-2-3-e]

In Formulas 1-2-3-a to Formulas 1-2-3-e,

R19 to R28, n1 and n2 have the same definitions as in Formula 1-2-3 above.

In one embodiment of the present invention, Chemical Formulas 1-2-3-a to Chemical Formulas 1-2-3-e may include 0 or more and 30 or less deuterium atoms as substituents.

In another embodiment of the present invention, Chemical Formulas 1-2-3-a to Chemical Formulas 1-2-3-e may include 1 or more and 10 or less deuterium atoms as substituents.

In one embodiment of the present invention, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituents in Formulas 1-2-3-a to Formula 1-2-3-e may be 0 to 100%. .

In another embodiment of the present invention, in Formula 1-2-3-a to Formula 1-2-3-e, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituents may be 20 to 90%. .

In another embodiment of the present invention, in Formula 1-2-3-a to Formula 1-2-3-e, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituents may be 40 to 80%. .

For example, in Formula 1-2-3-a to Formula 1-2-3-e, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituent is 0% or more, 1% or more, 10% or more, It may be 20% or more, 30% or more, 40% or more, 50% or more, 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

In one embodiment of the present invention, R19 to R28 in Formulas 1-2-3-a to Formula 1-2-3-e are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C2 to C30 alkenyl group; A substituted or unsubstituted C2 to C30 alkynyl group; A substituted or unsubstituted C1 to C30 alkoxy group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C2 to C30 heterocycloalkyl group; A substituted or unsubstituted C6 to C30 aryl group; A substituted or unsubstituted C2 to C30 heteroaryl group; -P(=0)R101R102; -SiR101R102R103; and -NR101R102, wherein R101, R102, and R103 are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group, n1 and n2 may be integers of 0 to 2, when n1 is 2, R19 may be the same as or different from each other, and when n2 is 2, R24 may be the same as or different from each other.

In another embodiment of the present invention, R19 to R28 in Formulas 1-2-3-a to Formula 1-2-3-e are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group, n1 may be an integer of 0 to 2, n1 and n2 may be an integer of 0 to 2, and when n1 is 2, R19 is the same as or different from each other. and when n2 is 2, R24 may be the same as or different from each other.

In another embodiment of the present invention, R19 to R28 in Formulas 1-2-3-a to Formula 1-2-3-e are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group, n1 may be an integer of 0 to 2, n1 and n2 may be an integer of 0 to 2, and when n1 is 2, R19 is the same as or different from each other. and when n2 is 2, R24 may be the same as or different from each other.

In another embodiment of the present invention, R19 to R28 in Formulas 1-2-3-a to Formula 1-2-3-e are the same as or different from each other, and each independently hydrogen; heavy hydrogen; It may be a substituted or unsubstituted phenyl group, biphenyl group, or naphthyl group, n1 and n2 may be integers from 0 to 2, when n1 is 2, R19 may be the same as or different from each other, and when n2 is 2 , R24 may be the same as or different from each other.

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

In addition, by introducing various substituents into the structure of Chemical Formula 1, compounds having unique characteristics of the introduced substituents can be synthesized. For example, by introducing a substituent mainly used in the hole injection layer material, the hole transport layer material, the light emitting layer material, the electron transport layer material, and the charge generation layer material used in the manufacture of an organic light emitting device into the core structure, the conditions required by each organic layer are met. substances can be synthesized.

In addition, by introducing various substituents into the structure of Chemical Formula 1, it is possible to finely control the energy band gap, while improving the properties of the interface between organic materials and diversifying the use of the material.

Meanwhile, the heterocyclic compound has a high glass transition temperature (Tg) and excellent thermal stability. This increase in thermal stability is an important factor in providing driving stability to the device.

The heterocyclic compound according to an exemplary embodiment of the present application may be prepared through a multi-step chemical reaction. Some intermediate compounds are prepared first, and the compound of Formula 1 can be prepared from the intermediate compounds. More specifically, the heterocyclic compound according to an exemplary embodiment of the present application may be prepared based on Preparation Examples described below.

Another exemplary embodiment of the present application provides an organic light emitting device including the heterocyclic compound represented by Formula 1 above. The “organic light emitting device” may be expressed in terms such as “organic light emitting diode”, “organic light emitting diodes (OLED)”, “OLED device”, and “organic light emitting device”.

In addition, in one embodiment of the present invention, the second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the heterocyclic compound represented by Chemical Formula 1. provide a small

In one embodiment of the present invention, the first electrode may be an anode, and the second electrode may be a cathode.

In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

In one embodiment of the present invention, 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 for the blue organic light emitting device.

In one embodiment of the present invention, 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 for the green organic light emitting device.

In one embodiment of the present invention, 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 for the red organic light emitting device.

In one embodiment of the present invention, 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 for a light emitting layer of the blue organic light emitting device.

In one embodiment of the present invention, 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 for an emission layer of the green organic light emitting device.

In one embodiment of the present invention, 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 for an emission layer of the red organic light emitting device.

Details of the heterocyclic compound represented by Formula 1 are the same as described above.

The organic light emitting diode of the present invention may be manufactured by conventional organic light emitting diode manufacturing methods and materials, except for forming one or more organic material layers using the aforementioned heterocyclic compound.

The heterocyclic compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

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

In the organic light emitting device of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound. When the heterocyclic compound is used in the light emitting layer, strong charge transfer is possible by spatially separating homo (HOMO, Highest Occupied Molecular Orbital) and LUMO (LUMO, HOMO, Lowest ighest Unoccupied Molecular Orbital) organic light emission The driving efficiency and lifespan of the device can be improved. Driving, efficiency, and lifespan of the organic light emitting device may be improved.

In the organic light-emitting device according to an embodiment of the present invention, the organic material layer including the heterocyclic compound represented by Formula 1 provides an organic light-emitting device that further includes a heterocyclic compound represented by Formula 2 below. .

[Formula 2]

In Formula 2,

X21 and X22 are the same as or different from each other, and are each independently O or S,

R31 to R39 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; -P(=0)R101R102; -SiR101R102R103; And -NR101R102, or two or more groups adjacent to each other combine to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and are each independently 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 heteroaryl group,

L2 is a direct bond, substituted or unsubstituted arylene group having 6 to 60 carbon atoms; A substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms, o is an integer of 0 to 3, and when o is 2 or more, each L2 is the same as or different from each other,

Z is any one of the following formulas 2-1 to 2-5,

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

In Formulas 2-1 to 2-5,

Ar3 to Ar5 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms,

R41 to R58 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; and -NR101R102, wherein R101, R102, and R103 are the same as or different from each other, and each independently 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 heteroaryl group,

p1 and p2 are the same as or different from each other, and are each independently an integer of 0 to 2, when p1 is 2, R49 is the same as or different from each other, and when n2 is 2, R54 is the same as or different from each other.

In one embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 2 may include at least one deuterium as a substituent.

In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 2 may include 1 or more and 50 or less deuterium atoms as substituents.

In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 2 may include 1 or more and 30 or less deuterium atoms as substituents.

In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 2 may include 9 or more and 40 or less deuterium atoms as substituents.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 2 may have a deuterium content of 0 to 100% based on the total number of hydrogen atoms and deuterium atoms in the substituents.

In another embodiment of the present invention, the heterocyclic compound represented by Formula 2 may have a deuterium content of 20 to 90% based on the total number of hydrogen atoms and deuterium atoms in the substituents.

In another embodiment of the present invention, the heterocyclic compound represented by Formula 2 may have a deuterium content of 40 to 80% based on the total number of hydrogen atoms and deuterium atoms in the substituents.

For example, in the heterocyclic compound represented by Formula 2, the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms in the substituent is 0% or more, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more It may be % or more, 50% or more, 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

In one embodiment of the present invention, the X21 and X22 are the same as or different from each other, and each independently may be O or S.

In another embodiment of the present invention, the X21 may be O, and the X22 may be S.

In another embodiment of the present invention, the X21 may be S, and the X22 may be O.

In one embodiment of the present invention, the R31 to R39 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C2 to C30 alkenyl group; A substituted or unsubstituted C2 to C30 alkynyl group; A substituted or unsubstituted C1 to C30 alkoxy group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C2 to C30 heterocycloalkyl group; A substituted or unsubstituted C6 to C30 aryl group; A substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; And it is selected from the group consisting of -NR101R102, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102, and R103 are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.

In another embodiment of the present invention, R31 to R39 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.

In another embodiment of the present invention, R31 to R39 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.

In another embodiment of the present invention, R31 to R39 are the same as or different from each other, and each independently hydrogen; or deuterium.

In one embodiment of the present invention, the L2 is a direct bond; A substituted or unsubstituted C6 to C30 arylene group; Or it may be a substituted or unsubstituted C6 to C30 heteroarylene group, and when o is 2 or more, each L2 may be the same as or different from each other.

In another embodiment of the present invention, L2 is a direct bond; A substituted or unsubstituted C6 to C20 arylene group; Or it may be a substituted or unsubstituted C6 to C20 heteroarylene group, and when o is 2 or more, each L2 may be the same as or different from each other.

In another embodiment of the present invention, L2 is a direct bond; A substituted or unsubstituted phenylene group, naphthylene group; Or it may be a substituted or unsubstituted dibenzofuranylene group, and when o is 2 or more, each L2 may be the same as or different from each other.

In one embodiment of the present invention, Ar3 and Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms. can

In another embodiment of the present invention, Ar3 and Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms. can

Ar3 and Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group, biphenyl group, naphthyl group or fluorenyl group; It may be a substituted or unsubstituted dibenzofuranyl group or dibenzothiophenyl group.

In one embodiment of the present invention, the R41 to R58 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C2 to C30 alkenyl group; A substituted or unsubstituted C2 to C30 alkynyl group; A substituted or unsubstituted C1 to C30 alkoxy group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C2 to C30 heterocycloalkyl group; A substituted or unsubstituted C6 to C30 aryl group; A substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; and -NR101R102, wherein R101, R102, and R103 are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C30 alkyl group; A substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.

In another embodiment of the present invention, R41 to R58 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.

In another embodiment of the present invention, R41 to R58 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.

In another embodiment of the present invention, R41 to R58 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; Or it may be a substituted or unsubstituted C2 to C30 carbazolyl group.

In one embodiment of the present invention, p1 and p2 are the same as or different from each other, each independently may be an integer of 0 to 2, when p1 is 2, R49 may be the same as or different from each other, and n2 is In the case of 2, R54 may be the same as or different from each other.

When the compound represented by Formula 1 and the compound represented by Formula 2 are included at the same time, better efficiency and lifespan effect are exhibited. From this, it can be expected that an exciplex phenomenon occurs when the two compounds are included at the same time.

The exciplex phenomenon is a phenomenon in which energy of the size of the HOMO energy level of a donor (p-host) and the LUMO energy level of an acceptor (n-host) is released by electron exchange between two molecules. When an exciplex between two molecules occurs, reverse intersystem crossing (RISC) occurs, and as a result, the internal quantum efficiency of fluorescence can be increased to 100%. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as the host of the light emitting layer, holes are injected into the p-host and electrons are injected into the n-host. Since it is injected, the driving voltage can be lowered, thereby helping to improve the lifespan. That is, when the compound represented by Chemical Formula 1 is used as the acceptor and the compound represented by Chemical Formula 2 is used as the donor, excellent device characteristics are exhibited.

In one embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 2 may be one or more selected from the following compounds.

In addition, one embodiment of the present invention provides a composition for an organic material layer of an organic light emitting device including the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2.

Details of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 are the same as described above.

In one embodiment of the present invention, the weight ratio of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 in the composition for the organic layer of the organic light emitting device may be 1:9 to 9:1, , 1: 9 to 5: 5, 2: 8 to 5: 5, but is not limited thereto.

The composition for the organic material layer of the organic light emitting device can be used when forming the organic material of the organic light emitting device, and in particular, can be more preferably used when forming the host of the light emitting layer.

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

As the phosphorescent dopant material, those known in the art may be used. For example, phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L ₂ MX' and L ₃ M may be used, but the scope of the present invention is not limited by these examples. .

The M may be iridium, platinum, osmium, or the like.

L is an anionic bidentate ligand coordinated to M by sp ² carbon and a hetero atom, and X may function to trap electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole), (7,8 -benzoquinoline), (thiophene pyrizine), phenylpyridine, benzothiophene pyrizine, 3-methoxy-2-phenylpyridine, thiophene pyrizine, tolylpyridine, and the like. Non-limiting examples of X' and X" include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.

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

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

In one embodiment of the present invention, (piq) ₂ (Ir) (acac) may be used as a red phosphorescent dopant as the iridium-based dopant.

In one embodiment of the present invention, the content of the dopant may have a content of 1 wt% to 15 wt%, preferably 3 wt% to 10 wt% based on the entire light emitting layer.

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

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

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

In the organic light emitting device according to another embodiment, the organic material layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound.

An organic light emitting device according to an embodiment of the present invention includes a light emitting layer, a hole injection layer, and a hole transport layer. It may further include one layer or two or more layers selected from the group consisting of an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

1 to 4 illustrate the stacking order of the electrode and the organic material layer of the organic light emitting device according to an embodiment of the present invention. However, it is not intended that the scope of the present application be limited by these drawings, and structures of organic light emitting devices known in the art may be applied to the present application as well.

According to FIG. 1 , an organic light emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is shown. However, it is not limited to such a structure, and as shown in FIG. 2, an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.

3 illustrates a case where the organic material layer is multi-layered. The organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, an emission 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 be omitted as necessary, and other necessary functional layers may be further added.

As an organic light emitting device according to an exemplary embodiment of the present application, an organic light emitting device having a 2-stack tandem structure is schematically shown in FIG. 4 below.

In this case, the first electron blocking layer, the first hole blocking layer, and the second hole blocking layer described in FIG. 4 may be omitted in some cases.

In one embodiment of the present invention, preparing a 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 organic material layer, wherein the forming of the organic material layer comprises forming one or more organic material layers using the composition for an organic material layer according to an embodiment of the present invention. It provides a method for manufacturing an organic light emitting device comprising the step of doing.

In one embodiment of the present invention, the forming of the organic material layer is performed by pre-mixing the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2, and using a thermal vacuum deposition method. It may be formed using

The pre-mixing means that the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 are first mixed and mixed in one source before depositing the heterocyclic compound represented by Chemical Formula 2 on the organic layer.

The premixed material may be referred to as a composition for an organic layer according to an exemplary embodiment of the present application.

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 2 may further include other materials as needed.

In the organic light-emitting device according to an embodiment of the present invention, materials other than the heterocyclic compound represented by Formula 1 or the heterocyclic compound represented by Formula 2 are exemplified below, but these are for illustrative purposes only. It is not intended to limit the scope of, and may be replaced with materials known in the art.

As the anode material, materials having a relatively large work function may be used, and transparent conductive oxides, metals, or conductive polymers may be used. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); 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] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

As the anode material, materials having a relatively low work function may be used, and metal, metal oxide, or conductive polymer may be used. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

As the hole injection layer material, a known hole injection layer material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a phthalocyanine compound disclosed in Advanced Material, 6, p.677 (1994). Starburst amine derivatives described, such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4″-tri[phenyl(m-tolyl)amino]triphenylamine ( m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/dodecylbenzenesulfonic acid, a soluble conductive polymer, or Poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), polyaniline/camphor sulfonic acid, or Polyaniline/Poly(4-styrene-sulfonate) and the like can be used.

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

Materials for the electron transport layer include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, and fluorenone. Derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc. may be used, and high molecular materials as well as low molecular materials may be used.

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

A red, green or blue light emitting material may be used as a material for the light emitting layer, and if necessary, two or more light emitting materials may be mixed and used. At this time, two or more light emitting materials may be deposited and used as separate sources or may be pre-mixed and deposited as one source. In addition, a fluorescent material may be used as a material for the light emitting layer, but it may also be used as a phosphorescent material. As the material for the light emitting layer, a single material that emits light by combining holes and electrons injected from the anode and the cathode may be used, but materials in which a host material and a dopant material are involved in light emission may also be used.

In the case of mixing and using hosts of the light emitting layer material, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, at least two materials selected from among n-type host materials and p-type host materials may be used as host materials for the light emitting layer.

An organic light emitting device according to an embodiment of the present invention may be a top emission type, a bottom emission type, or a double side emission type depending on the material used.

The heterocyclic compound according to an embodiment of the present invention may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoreceptor, and an organic transistor.

Hereinafter, preferred embodiments are presented to aid understanding of the present invention, but the following examples are provided to more easily understand the present invention, but the present invention is not limited thereto.

<Production Example>

<Preparation Example 1-1> Preparation of intermediates C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19 and C20

1) Preparation of Intermediate C1

(4-chlorophenyl) boronic acid ((4-chlorophenyl) boronic acid) (A1) 16.2 g (104 mmol), 2-chloro-4- (naphthalen-2-yl) -6-phenyl-1,3, 5-triazine (2-chloro-4- (naphthalen-2-yl) -6-phenyl-1,3,5-triazine) (B1) 30.0 g (94.4 mmol), tetrakis (triphenylphosphine) palladium (0) (tetrakis(triphenylhosphine)palladium(0), Pd(PPh ₃ ) ₄ ) 5.45 g (4.72 mmol), K ₂ CO ₃ 26.1 g (189 mmol), 90 mL of distilled water and 1,4-dioxane (1,4-dioxane) 300mL of 4-dioxane) was added to a 1 L round bottom flask, and stirred at 130°C for 2 hours (h). After the reaction was completed, it was cooled to room temperature and washed with distilled water and methanol (Methonol). The dried solid was dissolved in hot DCB ((1,2-dichlorobenzene), and then separated by a column under DCB conditions to obtain 35.0 g of intermediate C1 (yield: 94%).

2) Preparation of intermediates C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19 and C20

In the preparation of Intermediate C1, Intermediate C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19 and C20 were synthesized.

[Table 1]

<Preparation Example 1-2> Preparation of intermediates D1, D2, D3, D4, D5, D6, D7 and D8

1) Preparation of Intermediate D1

30.0 g (179 mmol) of carbazole as intermediate E1 and 300 mL of benzene-d6 were put into a 1L round bottom flask, and 60 mL of TfOH (Triflic acid) was slowly added dropwise thereto. It was stirred at 80 °C for 1 hour (h). After the reaction was completed, it was cooled to room temperature and washed with an excess of distilled water and methanol (Methonol). After dissolving the dried solid in hot DCB, it was separated by a column under DCB conditions to obtain 25.3 g of intermediate D1 (yield: 80%).

2) Preparation of intermediates D2, D3, D4, D5, D6, D7 and D8

Intermediates D2, D3, D4, D5, D6, D7 and D8 were synthesized in the same manner as in the preparation of Intermediate D1, except that Intermediate E in Table 2 was used instead of Intermediate E1 in the preparation of Intermediate D1.

[Table 2]

<Preparation Example 1-3> Compound 2, 8, 11, 33, 35, 40, 42, 43, 73, 75, 82, 83, 105, 153, 154, 408, 411, 425, 430, 432, 433, Preparation of 455, 462, 463 and 485

1) Preparation of Compound 2

Intermediate D1 2.24 g (12.7 mmol), Intermediate C1 5.00 g (12.7 mmol), Tris (dibenzylideneacetone) dipalladium (Tris (dibenzylideneacetone) dipalladium, Pd ₂ (dba) ₃ ) 0.58 g (0.63 mmol), dicyclo Hexyl (2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (Dicyclohexyl(2',4',6'-triisopropyl-[1,1' -biphenyl] -2-yl) phosphine, Xphos) 0.61 g (1.27 mmol), NaOtBu 2.44 g (25.4 mmol), and 50 mL of xylene were injected into a 250 mL round bottom flask, and incubated at 130 ° C for 2 hours (h). ) while stirring. After the reaction was completed, the mixture was cooled to room temperature and filtered through Celite with methylene chloride (MC). After concentrating the obtained organic layer, it was separated by a column under MC:Hexane=1:2 conditions to obtain 4.6 g of Compound 2 (yield: 68%).

2) Compounds 8, 11, 33, 35, 40, 42, 43, 73, 75, 82, 83, 105, 153, 154, 408, 411, 425, 430, 432, 433, 455, 462, 463 and 485 manufacture of

Compounds 8, 11, 33, 35, 40, 42, 43, 73, 75, 82, 83, 105, 153, 154, 408, 411, 425, 430, 432, 433, 455, 462, 463 and 485 were synthesized.

[Table 3]

<Preparation Example 1-4> Preparation of intermediates F1, F2, F3, F4, F5, F6, F7, F8, F9 and F10

1) Preparation of Intermediate F1

Intermediate E1 1.89 g (11.3 mmol), Intermediate C2 5.00 g (11.3 mmol), Tris (dibenzylideneacetone) dipalladium (Tris (dibenzylideneacetone) dipalladium, Pd ₂ (dba) ₃ ) 0.52 g (0.56 mmol), dicyclo Hexyl (2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (Dicyclohexyl(2',4',6'-triisopropyl-[1,1' -biphenyl] -2-yl) phosphine, Xphos) 0.54 g (1.13 mmol), NaOtBu 2.17 g (22.6 mmol), and 50 mL of xylene were added to a 250 mL round bottom flask, and incubated at 130 ° C for 2 hours (h). ) while stirring. After the reaction was completed, the mixture was cooled to room temperature and filtered through Celite using MC. After concentrating, the mixture was separated through a column under MC:Hexane=1:2 conditions to obtain 4.6 g of intermediate F1 (yield: 71%).

2) Preparation of intermediates F2, F3, F4, F5, F6, F7, F8, F9 and F10

Intermediates F2, F3, F4, F5, F6, F7, F8, F9 and F10 were synthesized.

[Table 4]

<Preparation Example 1-5> Preparation of intermediates H1, H2, H3, H4, H5, H6, H7, H8, H9, H10, H11, H12, H13, H14 and H15

1) Preparation of Intermediate H1

10.0 g (5.7 mmol) of intermediate D3 and 15.1 g (3.6 mmol) of intermediate L1, 0.40 g (1.79 mmol) of palladium (II) acetate, (5-diphenylphosphanyl-9,9-dimethyl Xanthen-4-yl) -dibenzylphosphane ((5-diphenylphosphanyl-9,9-dimethylxanthen-4-yl) -diphenylphosphane, Xantphos) 2.06g (3.57 mmol), NaOtBu 6.85g (71.3 mmol), Toluene ) into a 250 mL round bottom flask, and stirred at 70 °C for 4 hours. After the reaction was completed, the mixture was cooled to room temperature and filtered through Celite using MC. After dissolving the concentrated solid in hot DCB, it was separated by a column under DCB conditions to obtain 11.2 g of intermediate G1 (yield: 72%).

Intermediate G1 11.2 g (25.8 mmol) and bis (pinacolato) diboron (Bis (pinacolato) diboron, B2pin2) 6.87 g (27.1 mmol), [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II)([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), Pd(dppf)Cl2) 0.99g(1.35mmol), KOAc 5.31g(54.1mmol), 250mL of 110mL of dioxane It was added to a round bottom flask and refluxed for 4 hours. After the reaction was completed, the mixture was filtered while hot to remove salt. The concentrated compound was separated through a column under MC;Hexane=1:4 conditions to obtain 10.7 g of intermediate H1 (yield: 86%).

2) Preparation of intermediates H2, H3, H4, H5, H6, H7, H8, H9, H10, H11, H12, H13, H14 and H15

In the preparation of Intermediate H1, Intermediate H2, H3, Intermediate H2, H3, H4, H5, H6, H7, H8, H9, H10, H11, H12, H13, H14 and H15 were synthesized.

[Table 5]

<Preparation Example 1-6> Compound 602, 608, 611, 623, 630, 632, 633, 653, 685, 689, 811, 823, 832, 1002, 1008, 1023, Intermediate F11, F12, F13, F14, F15 , preparation of F16, F17, F18 and F19

1) Preparation of compound 602

5.00 g (10.4 mmol) of intermediate H1, 2-chloro-4- (naphthalen-2-yl) -6-phenyl-1,3,5-triazine (2-chloro-4- (naphthalen-2- yl)-6-phenyl-1,3,5-triazine) 3.23g (10.2 mmol), tetrakis(triphenylphosphine)palladium(0) (tetrakis(triphenylhosphine)palladium(0), Pd(PPh ₃ ) ₄ ) 0.60 g (0.52 mmol), K ₂ CO ₃ 2.87 g (20.8 mmol), 15 mL of distilled water and 50 mL of 1,4-dioxane (1,4-dioxane) were added to a 250 mL round bottom flask, and incubated at 130 ° C. for 2 hours ( h). After the reaction was completed, the mixture was cooled to room temperature and filtered through Celite using MC. The concentrated compound was separated through a column under MC;Hexane=1:2 conditions to obtain 5.9 g of Compound 602 (yield: 89%).

and Manufacture of F19

Compounds 608, 611, 623, 630, 632, 633, 653 were prepared in the same manner as in the preparation of compound 602, except that Intermediate H and Intermediate B in Table 6 were used instead of Intermediate H1 and Intermediate B1 in the preparation of Compound 602. , 685, 689, 811, 823, 832, 1002, 1008, 1023, intermediates F11, F12, F13, F14, F15, F16, F17, F18, F19 were synthesized.

[Table 6]

<Preparation Example 1-7> Preparation of compounds 232, 240, 249, 266, 306, 517, 532, 540, 556, 566, 707, 717, 725, 732, 740, 940, 976, 1117 and 1132

1) Preparation of compound 232

4.6g (8.0 mmol) of intermediate F1 and 46mL of benzene-d6 were put into a 1L round bottom flask, and 9.2mL of TfOH (Triflic acid) was slowly added dropwise thereto. It was stirred at 80 °C for 1 hour. After the reaction was completed, it was cooled to room temperature and washed with an excess of distilled water and methanol (Methonol). After dissolving the dried solid in hot DCB, it was separated by a column under DCB conditions to obtain 4.0 g of Compound 232 (yield: 83%).

2) Preparation of compounds 240, 249, 266, 306, 517, 532, 540, 556, 566, 707, 717, 725, 732, 740, 940, 976, 1117 and 1132

Compounds 240, 249, 266, 306, 517, 532, 540, 556, 566, 707 were prepared in the same manner as in the preparation of Compound 232, except that Intermediate F in Table 7 was used instead of Intermediate F1 in the preparation of Compound 232. , 717, 725, 732, 740, 940, 976, 1117 and 1132 were synthesized.

[Table 7]

The remaining compounds other than the compounds described in Preparation Examples 1-1 to 1-7 and Tables 1 to 7 were also prepared in the same manner as described in the above Preparation Examples, and the synthesis results are shown in Tables 8 and 9 below. . Table 8 below is ¹ H NMR (CDCl ₃ , 300 Mz), and Table 9 below is the measured value of FD-mass spectrometer (FD-MS: Field desorption mass spectrometry).

[Table 8]

[Table 9]

<Production Example 2>

<Preparation Example 2-1> Preparation of Intermediates J1 and J2

1) Preparation of Intermediate J1

30.0 g (84.9 mmol) of Intermediate I1 and 300 mL of benzene-d6 were placed in a 1 L round bottom flask, and 60 mL of TfOH (Triflic acid) was slowly added dropwise thereto. It was stirred at 80 °C for 1 hour (h). After the reaction was completed, it was cooled to room temperature and washed with an excess of distilled water and methanol (Methonol). After dissolving the dried solid in hot DCB, it was separated by a column under DCB conditions to obtain 24 g of intermediate J1 (yield: 78%).

2) Preparation of Intermediate J2

Intermediate J2 was synthesized in the same manner as in the preparation of Intermediate J1, except that Intermediate I2 was used instead of Intermediate I1 in the preparation of Intermediate J1.

<Preparation Example 2-2> Preparation of intermediates M1 and M2

1) Preparation of intermediate M1

Intermediate I1 10.0 g (28.3 mmol), di ([1,1'-biphenyl] -4-yl) amine (di ([1,1'-biphenyl] -4-yl) amine, Intermediate K1) 10.01 g ( 31.1 mmol), Tris (dibenzylideneacetone) dipalladium (Pd ₂ (dba) ₃ ) 1.30 g (1.4 mmol), dicyclohexyl (2', 4', 6'-triisopropyl -[1,1'-biphenyl]-2-yl)phosphine (Dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine, Xphos) 1.35g (2.8 mmol), sodium tert-butoxide (NaOtBu) 5.44 g (56.6 mmol) and xylene (Xylene) 100mL were put into a 500mL round bottom flask, and refluxed at 130 ° C. for 2 hours. After the reaction was completed, the mixture was cooled to room temperature and passed through a Celite filter. After concentrating, the mixture was separated through a column under MC:Hexane=1:4 conditions to obtain 15.6 g (26.3 mmol, yield: 93%) of intermediate M1.

2) Preparation of intermediates M2, M4 and M5

Intermediates M2, M4 and M5 were prepared in the same manner as in the preparation of Intermediate M1, except that Intermediate I in Table 10 was used instead of Intermediate I1 in the preparation of Compound M1, and Intermediate K in Table 10 was used instead of Intermediate K1. synthesized.

[Table 10]

<Preparation Example 2-3> Preparation of Compounds 2027 and 2028 and Intermediate M3

1) Preparation of Compound 2027

Intermediate J2 10.0 g (27.6 mmol), Intermediate N1 17.5 g (29.0 mmol), tetrakis (triphenylphosphine) palladium (0) (tetrakis (triphenylhosphine) palladium (0), Pd (PPh ₃ ) ₄ ) 1.65 g ( 1.43 mmol), K ₂ CO ₃ 7.63 g (55.2 mmol), 30 mL of distilled water and 100 mL of 1,4-dioxane (1,4-dioxane) were added to a 500 mL round bottom flask and refluxed at 130 ° C. for 2 hours. . After the reaction was completed, the mixture was cooled to room temperature and passed through a Celite filter. After concentration, 18.0 g (yield: 86%) of compound 2027 was obtained by separation through a column under MC:Hexane=1:4 conditions.

2) Preparation of Compound 2028 and Intermediate M3

Compound 2028 and Intermediate M3 were prepared in the same manner as in the preparation of Compound 2027, except that Intermediates J and I in Table 11 were used instead of Intermediate J2 in the preparation of Compound 2027, and Intermediate N in Table 11 was used instead of Intermediate N1. was synthesized.

[Table 11]

<Preparation Example 2-4> Preparation of compounds 2002, 2012, 2018, 2054 and 2078

1) Preparation of Compound 2002

10.0 g (16.8 mmol) of intermediate M1 and 100 mL of benzene-d6 (Benzene-d6) were put into a 1L round bottom flask, and 30 mL of TfOH (Triflic acid) was slowly added dropwise. It was stirred for 1 hour (h) at 80°C. After the reaction was completed, the mixture was cooled to room temperature and filtered through Celite with methylene chloride (MC). After concentration, 8.5 g (yield: 81%) of Compound 2002 was obtained by separation through a column under MC:Hexane=1:4 conditions.

2) Preparation of compounds 2012, 2018, 2054 and 2078

Compounds 2012, 2018, 2054 and 2078 were synthesized in the same manner as in the preparation of Compound 2002, except that Intermediate M in Table 12 was used instead of Intermediate M1 in the preparation of Compound 2002.

[Table 12]

The remaining compounds other than the compounds described in Preparation Examples 2-1 to 2-4 and Tables 10 to 12 were also prepared in the same manner as described in the above Preparation Examples, and the synthesis results are shown in Table 13 below. Table 13 below is a measurement value of FD-mass spectrometry (FD-MS: Field desorption mass spectrometry), ¹ H was omitted because it did not exist, and a measurement value of ¹ H NMR (CDCl ₃ , 300 Mz) was omitted.

[Table 13]

<Experimental Example 1>

(1) Production of organic light emitting device (red host)

A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with solvents such as acetone, methanol, and isopropyl alcohol, and after drying, UVO (Ultraviolet ozone) treatment was performed for 5 minutes using UV in a UV (Ultraviolet) cleaner. Thereafter, the substrate was transferred to a plasma cleaner (PT), plasma treated to increase the work function of ITO and remove residual films in a vacuum state, and then transferred to a thermal evaporation equipment for organic deposition.

A hole injection layer 2-TNATA (4,4′,4′′-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N′-Di) as a common layer on the ITO transparent electrode (anode) (1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed.

A light emitting layer was thermally vacuum deposited thereon as follows. The light emitting layer was deposited with the compound of Formula 1 shown in Table 14 as a host to a thickness of 500 Å, and was doped with a red phosphorescent dopant [(piq) ₂ (Ir) (acac)] at 3% by weight based on the weight of the host. It was deposited. Thereafter, bathocuproine (BCP) was deposited to a thickness of 60 Å as a hole blocking layer, and Alq ₃ was deposited to a thickness of 200 Å as an electron transport layer thereon. Finally, after depositing lithium fluoride (LiF) to a thickness of 10 Å on the electron transport layer to form an electron injection layer, an aluminum (Al) cathode is deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode By doing so, an organic light emitting device was manufactured.

On the other hand, all organic compounds required for OLED device fabrication were purified by vacuum sublimation under 10 -8 to 10 ^-6 torr for each material, respectively, and used for OLED fabrication.

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

The electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured with McSyers' M7000, and the standard luminance was 6,000cd through the lifetime equipment measuring equipment (M6000) manufactured by McScience with the measurement result. /m ² , T ₉₀ was measured. The characteristics of the organic electroluminescent device of the present invention are shown in Table 14 below. The above, T ₉₀ means a lifetime (unit: h, time), which is the time when the initial luminance becomes 90%.

The results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the organic light emitting device manufactured according to the present invention are shown in Table 14 below. In addition, the results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the organic light emitting device manufactured using the comparative compound as the light emitting layer compound are shown in Table 14 below.

[Table 14]

<Experimental Example 2> Fabrication of organic light emitting device

A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with solvents such as acetone, methanol, and isopropyl alcohol, and after drying, UVO (Ultraviolet ozone) treatment was performed for 5 minutes using UV in a UV (Ultraviolet) cleaner. Thereafter, the substrate was transferred to a plasma cleaner (PT), plasma treated to increase the work function of ITO and remove residual films in a vacuum state, and then transferred to a thermal evaporation equipment for organic deposition.

A hole injection layer 2-TNATA (4,4′,4′′-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N′-Di) as a common layer on the ITO transparent electrode (anode) (1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed.

A light emitting layer was thermally vacuum deposited thereon as follows. For the light emitting layer, a mixture of the compound of formula 1 and the compound of formula 2 shown in Table 15 was deposited to a thickness of 500 Å as a host, and a red phosphorescent dopant [(piq) ₂ (Ir)(acac)] was added in an amount of 3 weight relative to the weight of the host. It was deposited by doping with %. Thereafter, bathocuproine (BCP) was deposited to a thickness of 60 Å as a hole blocking layer, and Alq ₃ was deposited to a thickness of 200 Å as an electron transport layer thereon. Finally, after depositing lithium fluoride (LiF) to a thickness of 10 Å on the electron transport layer to form an electron injection layer, an aluminum (Al) cathode is deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode By doing so, an organic light emitting device was manufactured.

On the other hand, all organic compounds required for OLED device fabrication were purified by vacuum sublimation under 10 -8 to 10 ^-6 torr for each material, respectively, and used for OLED fabrication.

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

The electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured with McSyers' M7000, and the standard luminance was 6,000cd through the lifetime equipment measuring equipment (M6000) manufactured by McScience with the measurement result. /m ² , T ₉₀ was measured. The characteristics of the organic electroluminescent device of the present invention are as shown in Table 15 below. The above, T ₉₀ means a lifetime (unit: h, time), which is the time when the initial luminance becomes 90%.

The results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the organic light emitting device manufactured according to the present invention are shown in Table 15 below. In addition, the results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the organic light emitting device manufactured using the comparative compound as the light emitting layer compound are shown in Table 15 below.

[Table 15]

Compounds A to H used in Tables 14 and 15 are as follows.

As can be seen from the results of Table 14, in the case of Examples 1 to 66 in which the heterocyclic compound of Formula 1 of the present invention was used as a host of the organic material layer of the organic light emitting device, particularly the light emitting layer, the organic light emitting device of Comparative Examples 1 to 6 It was confirmed that the efficiency and lifespan were improved.

The biggest difference between the above examples and comparative examples of the present invention is the presence or absence of deuterium substitution, and the effect of deuterium substitution can be explained from the comparison results of Examples 1 to 66 and Comparative Examples 1 to 6 of the present application.

Specifically, deuterium has a lower zero point energy and a lower vibrational energy because it has one more neutron than hydrogen. Since the bond dissociation energy of C-D has a value greater than that of C-H by about 5 kJ/mol, deuterium-substituted compounds (Examples 1 to 66) are replaced with hydrogen-substituted compounds (Comparative Example 1 to 6), it is effective in life and high temperature life. In addition, since the compounds substituted with deuterium (Examples 1 to 66) have higher bond dissociation energy and lower ground state energy than the compounds not substituted with deuterium (Comparative Examples A to C), the efficiency can be effectively improved. can

As can be seen from the results of Table 15, when the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 according to the present invention are used as the host of the organic layer of the organic light emitting device, particularly the light emitting layer, in the ratio shown in Table 15. (Examples 67 to 102) and Comparative Examples 7 to 15, it was confirmed that the efficiency and lifetime were improved.

The cause of this result is determined to be exciplex, a phenomenon in which two molecules emit energy due to a difference in energy. Specifically, the heterocyclic compound represented by Formula 1 according to the present invention has N-type properties than the heterocyclic compound represented by Formula 2, and the heterocyclic compound represented by Formula 2 has P-type properties.

When the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 according to the present invention are used in the device in the ratio shown in Table 15, the LUMO level of the acceptor (N-type host) by electron exchange between the two molecules The exciplex phenomenon, which is a phenomenon of emission due to the energy difference between the HOMO level of the donor and the donor (P-type host), is more likely to occur.

When a donor (P-type host) with good hole transport ability and an acceptor (N-type host) with good electron transport ability are used as the host of the light emitting layer by the exciplex phenomenon, the hole is P Since electrons are injected into the -type host and electrons are injected into the N-type host, it is easy to combine electrons and holes in the light emitting layer. That is, when the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 of the present invention are used in a device, it can be confirmed that the driving voltage, efficiency, and lifespan are improved compared to using a single molecule. there was.

Additionally, HOMO, LUMO, Eg, S1, T1, dipole moment for the molecules of Compound A used in Comparative Example 1 and Compounds 8 and 232 included in the heterocyclic compounds of Formula 1 of the present application, respectively ) values were calculated, and the results are shown in Table 16 below. The Eg, T1 and S1 denote a band gap, a triplet excited state (T1 level) and a singlet excited state (S1 level), respectively.

From the molecular calculation results in Table 16, when hydrogen is replaced with deuterium, HOMO, LUMO, Eg, S1, T1, and dipole moment values are calculated to be the same.

[Table 16]

In addition, for the molecules of Compound A used in Comparative Example 1 and Compounds 8 and 232 included in the heterocyclic compounds of Formula 1 of the present invention, the SOMO values of the radical anion SOMO (singly occupied molecular orbital) and the radical cation It was calculated, and the results are shown in Table 17 below. SOMO refers to a singly occupied molecular orbital, such as HOMO, which is half-filled with radicals.

From the molecular calculation results in Table 17, the SOMO of the radical cation of Compound A substituted with hydrogen is limited to one naphthalene portion, whereas the SOMO of the radical cation of Compound 232 substituted with deuterium is both naphthalene It can be confirmed that it is more effective in electron transfer by being distributed in the area. The effect of deuterium substitution is determined to be due to SOMO rather than HOMO, LUMO, Eg, S1, T1, and dipole moment values.

[Table 17]

<Experimental Example 3> Thermal stability of organic electroluminescent device

The temperature measurement point (Ts) and evaluation time were determined as shown in Table 18 for the organic electroluminescent device manufactured as described above, and the purity at 50 ° C, 70 ° C, and 90 ° C was determined based on the temperature measurement point by McSyers. Thermal stability of the organic light emitting device was evaluated by measuring with M7000 of the company.

In addition, the electroluminescence (EL) characteristics at 50 ° C, 70 ° C and 90 ° C based on the temperature measurement point were measured with McSyers' M7000, and the life measurement equipment (M6000) manufactured by McScience with the measurement results When the standard luminance is 6,000 cd/m ² , the lifetime T90 (unit: h, time), which is the time to reach 90% of the initial luminance, was measured.

Accordingly, the results of measuring the purity, driving voltage, luminous efficiency and lifetime of the organic light emitting device are shown in Tables 18 and 19 below.

[Table 18]

[Table 19]

As can be seen from Tables 18 and 19, the compounds of the present invention have excellent thermal stability due to the C-D bond. Deuterium has one more neutron than hydrogen, so it has a lower zero point energy and a lower vibrational energy. In addition, since the bond dissociation energy of C-D has a value greater than the bond dissociation energy of C-H by about 5 kJ / mol, the compound substituted with deuterium (Examples 1 to 66) is a compound substituted with hydrogen ( Compared to Comparative Examples 1 to 6), they have lower ground state energy, and as a result, representative compounds 8, 35, 232, 266, 532, 608 and 732 substituted with deuterium have hydrogen-substituted compounds (Comparative Example A and D) has a higher high temperature lifetime.

In addition, when carbazole and polycyclic carbazole functional groups are not directly bonded and a linker (linker) such as phenyl or naphthyl is inserted in the middle, the molecular weight and structural planarity increase compared to the directly bonded compound. Thus, a compound having better thermal stability can be obtained.

100: substrate
200: anode
300: organic material layer
301: hole injection layer
302: hole transport layer
303: light emitting layer
304: hole blocking layer
305: electron transport layer
306: electron injection layer
400: cathode

Claims (16)

A heterocyclic compound represented by Formula 1 below:
[Formula 1]

In Formula 1,
X1 to X3 are the same as or different from each other, and are each independently CRa or N,
R1 and Ra are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; And -NR101R102, or two or more groups adjacent to each other combine to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and are each independently 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 heteroaryl group, and when R1 or Ra is plural, each R1 or Ra is the same as or different from each other,
Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms,
L1 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms, l is an integer of 1 to 3, and when l is 2 or more, each L1 is the same as or different from each other,
Ring A and ring B are the same as or different from each other, and are each independently a substituted or unsubstituted aryl ring having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl ring having 5 to 60 carbon atoms,
m is an integer from 0 to 8, and when m is 2 or more, each R1 is the same as or different from each other. According to claim 1,
A heterocyclic compound in which Formula 1 contains at least one deuterium as a substituent. According to claim 1,
The heterocyclic compound represented by Formula 1 does not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms is 1% to 90%, the heterocyclic compound. According to claim 1,
in Formula 1 above

Any one of the following formulas 1-1-1 to 1-1-2, a heterocyclic compound.
[Formula 1-1-1]

[Formula 1-1-2]

[Formula 1-1-3]

In Formulas 1-1-1 to Formulas 1-1-3,
Ar1, Ar2, X1 and X3 are the same as defined in Formula 1 above. According to claim 4,
A heterocyclic compound in which Formula 1-1-1 to Formula 1-1-3 contain at least one deuterium as a substituent. According to claim 1,
in Formula 1 above

Any one of the following formulas 1-2-1 to 1-2-3, a heterocyclic compound.
[Formula 1-2-1]

[Formula 1-2-2]

[Formula 1-2-3]

In Formulas 1-2-1 to Formulas 1-2-3,
R11 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; and -NR101R102, wherein R101, R102, and R103 are the same as or different from each other, and each independently 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 heteroaryl group,
n1 and n2 are the same as or different from each other, and are each independently an integer of 0 to 2, when n1 is 2, R19 is the same as or different from each other, and when n2 is 2 or more, R24 is the same as or different from each other. According to claim 6,
A heterocyclic compound in which Formula 1-2-1 to Formula 1-2-3 contain at least one deuterium as a substituent. According to claim 6,
Formula 1-2-2 is any one of Formulas 1-2-2-a to Formula 1-2-2-c, a heterocyclic compound.
[Formula 1-2-2-a]

[Formula 1-2-2-b]

[Formula 1-2-2-c]

In Formulas 1-2-2-a to Formulas 1-2-2-c,
R11 to R14, R19 to R23 and n1 have the same definitions as in Formula 1-2-2. According to claim 6,
Formula 1-2-3 is any one of Formulas 1-2-3-a to Formula 1-2-3-e, a heterocyclic compound.
[Formula 1-2-3-a]

[Formula 1-2-3-b]

[Formula 1-2-3-c]

[Formula 1-2-3-d]

[Formula 1-2-3-e]

In Formulas 1-2-3-a to Formulas 1-2-3-e,
R19 to R28, n1 and n2 have the same definitions as in Formula 1-2-3 above. According to claim 1,
Formula 1 is a heterocyclic compound represented by any one of the following compounds:

a first electrode;
a second electrode provided to face the first electrode; and
An organic light emitting device comprising one or more organic material layers provided between the first electrode and the second electrode,
At least one layer of the organic material layer will include the heterocyclic compound according to any one of claims 1 to 10, an organic light emitting device. According to claim 11,
The organic material layer further comprises a heterocyclic compound represented by Formula 2 below, an organic light emitting device:
[Formula 2]

In Formula 2,
X21 and X22 are the same as or different from each other, and are each independently O or S,
R31 to R39 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; And -NR101R102, or two or more groups adjacent to each other combine to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and are each independently 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 heteroaryl group,
L2 is a direct bond, substituted or unsubstituted arylene group having 6 to 60 carbon atoms; A substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms, o is an integer of 1 to 3, and when o is 2 or more, each L2 is the same as or different from each other,
Z is any one of the following formulas 2-1 to 2-5,
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

In Formulas 2-1 to 2-5,
Ar3 to Ar5 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms,
R41 to R58 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; -P(=0)R101R102; -SiR101R102R103; and -NR101R102, wherein R101, R102, and R103 are the same as or different from each other, and each independently 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 heteroaryl group,
p1 and p2 are the same as or different from each other, and are each independently an integer of 0 to 2, when p1 is 2, R49 is the same as or different from each other, and when n2 is 2, R54 is the same as or different from each other. According to claim 12,
The organic light emitting device, wherein the heterocyclic compound represented by Formula 2 is any one selected from the following compounds:

According to claim 11,
The organic light emitting device includes a light emitting layer, a hole injection layer, and a hole transport layer. An organic light emitting device further comprising one layer or two or more layers selected from the group consisting of an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. A composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound according to any one of claims 1 to 10 and a heterocyclic compound represented by Formula 2 below:
[Formula 2]

In Formula 2,
X21 and X22 are the same as or different from each other, and are each independently O or S,
R31 to R39 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; And -NR101R102, or two or more groups adjacent to each other combine to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and are each independently 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 heteroaryl group,
L2 is a direct bond, substituted or unsubstituted arylene group having 6 to 60 carbon atoms; A substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms, o is an integer of 1 to 3, and when o is 2 or more, each L2 is the same as or different from each other,
Z is any one of the following formulas 2-1 to 2-5,
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

In Formulas 2-1 to 2-5,
Ar3 to Ar5 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms,
R41 to R58 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; A substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C2 to C60 alkenyl group; A substituted or unsubstituted C2 to C60 alkynyl group; A substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C3 to C60 cycloalkyl group; A substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; and -NR101R102, wherein R101, R102, and R103 are the same as or different from each other, and each independently 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 heteroaryl group,
p1 and p2 are the same as or different from each other, and are each independently an integer of 0 to 2, when p1 is 2, R49 is the same as or different from each other, and when n2 is 2, R54 is the same as or different from each other. According to claim 15,
A composition for an organic layer of an organic light emitting device, wherein the weight ratio of the heterocyclic compound represented by Formula 1 to the heterocyclic compound represented by Formula 2 is 1:9 to 9:1.

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