KR102399701B1 - Heterocyclic compound, organic light emitting device comprising same and composition for organic layer of organic light emitting device - Google Patents

Abstract

The present application provides a heterocyclic compound, an organic light emitting device in which the heterocyclic compound is included in the organic material layer, and a composition for an organic material layer of the organic light emitting device.

Description

Heterocyclic compound, organic light emitting device containing same, and composition for organic material layer of organic light emitting device {HETEROCYCLIC COMPOUND, ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME AND COMPOSITION FOR ORGANIC LAYER OF ORGANIC LIGHT EMITTING DEVICE}

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

The electroluminescent device is a type of self-emission type display device, and has advantages of 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 a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers, if necessary.

The material of the organic thin film may have a light emitting function if necessary. For example, as the organic thin film material, a compound capable of forming the light emitting layer by itself may be used, or a compound capable of serving as a host or dopant of the host-dopant light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing the roles of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and the like may be used.

In order to improve the performance, lifespan, or efficiency of an organic light emitting diode, the development of a material for an organic thin film is continuously required.

U.S. Patent No. 4,356,429

An object of the present specification is to provide a heterocyclic compound, an organic light emitting device including the same, and a composition for an organic material layer of the organic light emitting device.

An exemplary embodiment of the present application provides a heterocyclic compound represented by the following formula (1).

[Formula 1]

In Formula 1,

L is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroarylene group,

L ₁ And L ₂ Are the same as or different from each other, each independently, a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms,

X ₁ and X ₂ are the same as or different from each other, each independently O or S,

R _p and R _q are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituted or unsubstituted C 6 to C 60 aryl group; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

a is an integer of 1 or 2, and when a is 2, the substituents in parentheses are the same or different from each other,

b and c are each an integer of 0 to 4, and when b and c are each 2 or more, the substituents in parentheses are the same as or different from each other,

m and n are each an integer of 0 to 2, and when m and n are each 2, the substituents in parentheses are the same as or different from each other.

In addition, an exemplary embodiment of the present application, the first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one organic material layer includes the heterocyclic compound represented by Formula 1 above. provides

Finally, an exemplary embodiment of the present application provides a composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound represented by the formula (1) and the heterocyclic compound represented by the following formula (11).

[Formula 11]

In the above formula (11),

L ₁₁ and L ₁₂ are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroarylene group,

X ₁₁ is O; S; or CR _b R _c , wherein R _b and R _c are the same as or different from each other, and each independently represents a substituted or unsubstituted C 1 to C 10 alkyl group,

Y ₁₁ to Y ₁₅ are the same as or different from each other, and each independently represents N or CR _d , and at least one of Y ₁₁ to Y ₁₅ is N,

each R _d is the same as or different from each other, and each independently represents hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted C 2 to C 60 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C 6 to C 60 aromatic hydrocarbon ring or a substituted or unsubstituted C 2 to form a heterocyclic ring of 60;

Ar ₁₁ is hydrogen; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

p and q are respectively 0 or 1.

The heterocyclic compound described herein may be used as an organic material layer of an organic light emitting device. The compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like in the organic light emitting device. In particular, the heterocyclic compound may be used as an electron transport layer material, a hole auxiliary layer material, or a charge generation layer material of an organic light emitting device.

Specifically, when the heterocyclic compound represented by Formula 1 is used in the organic material layer, it is possible to lower the driving voltage of the device, improve the light efficiency, and improve the lifespan characteristics of the device.

1 to 4 are diagrams exemplarily showing a stacked structure of an organic light emitting device according to an exemplary embodiment of the present application.
5 to 7 are diagrams showing PL results when Compound 68 of the present application was used, PL results when n-Host A was used, and PL results when Compound 68 and n-Host A were used simultaneously.
8 to 10 are diagrams showing PL results when Compound 4 of the present application was used, PL results when n-Host B was used, and PL results when Compound 4 and n-Host B were simultaneously used.

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

In the present specification, when a part "includes" a certain component, this means that other components may be further included, rather than excluding other components, unless otherwise stated.

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

In the present specification, "substituted or unsubstituted" refers to a linear or branched alkyl group having 1 to 60 carbon atoms; a linear or branched alkenyl group having 2 to 60 carbon atoms; a linear or branched alkynyl group having 2 to 60 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 60 carbon atoms; a monocyclic or polycyclic heterocycloalkyl group having 2 to 60 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 60 carbon atoms; a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms; silyl group; a phosphine oxide group; And it means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of an amine group, or substituted or unsubstituted with a substituent to which two or more substituents selected from the above-exemplified substituents are connected.

More specifically, In the present specification, "substituted or unsubstituted" means a monocyclic or polycyclic aryl group having 6 to 60 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms; It may mean unsubstituted or substituted with one or more substituents selected from the group.

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 in the alkyl group may be 1 to 60, specifically 1 to 40, 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, and the like, 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 carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20. Specific examples include a vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 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, etc., but are not limited thereto.

In the present specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. 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 and the like may be used, but is not limited thereto.

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted by other substituents. Here, polycyclic means a group in which a cycloalkyl group is directly connected to another ring group or condensed. Here, the other ring group may be a cycloalkyl group, but may be a different type of ring group, for example, a heterocycloalkyl group, an aryl group, a heteroaryl group, or the like. The carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, 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, and the like, but is 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, polycyclic refers to 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 be a different type of ring group, for example, a cycloalkyl group, an aryl group, a heteroaryl group, or the like. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, 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 by other substituents. Here, polycyclic means a group in which an aryl group is directly connected or condensed with another ring group. Here, the other ring group may be an aryl group, but may be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, or the like. The aryl group includes a spiro group. The carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrethyl 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(=O)R101R102, R101 and R102 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. The phosphine oxide group specifically includes, but is not limited to, a diphenylphosphine oxide group, a dinaphthylphosphine oxide, and the like.

In the present specification, the silyl group is a substituent including Si and the Si atom is directly connected as a radical, and is represented by -SiR104R105R106, R104 to R106 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 tert-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 combine with each other to form a ring.

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 spiro group may include any one of the 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 ring having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic refers to 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 be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, an aryl group, or the like. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, 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, 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, deoxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinazolylyl group, naphthyridyl group, acridinyl group, phenanthridyl group 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, Phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10, 11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiazinyl group, phthalazinyl group, naphthylidinyl group, phenanthrolinyl group, Benzo[c][1,2,5]thiadiazolyl group, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, 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 ] a 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; diarylamine group; diheteroarylamine group; an alkylarylamine group; an alkyl heteroarylamine group; And it may be selected from the group consisting of an aryl heteroarylamine group, 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, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorene There is a nylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but is not limited thereto.

In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied. In addition, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.

As used herein, the "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. can For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.

An exemplary embodiment of the present application provides a heterocyclic compound represented by the following formula (1).

[Formula 1]

In Formula 1,

L is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroarylene group,

L ₁ And L ₂ Are the same as or different from each other, each independently, a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms,

X ₁ and X ₂ are the same as or different from each other, each independently O or S,

R _p and R _q are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituted or unsubstituted C 6 to C 60 aryl group; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

a is an integer of 1 or 2, and when a is 2, the substituents in parentheses are the same or different from each other,

b and c are each an integer of 0 to 4, and when b and c are each 2 or more, the substituents in parentheses are the same as or different from each other,

m and n are each an integer of 0 to 2, and when m and n are each 2, the substituents in parentheses are the same as or different from each other.

The heterocyclic compound represented by Formula 1 has a structure in which benzothiophene or benzofuran is substituted at positions 2, 3 and 4 and 5 of the pyrrole compound, respectively, and has an amine group as a specific substituent. Accordingly, it is possible to delocalize the HOMO (Highest Occupied Molecular Orbital) energy level, thereby increasing the hole transport ability and stabilizing the HOMO energy. This is because when the material of Formula 1 is used as a material for the light emitting layer or hole auxiliary layer in the organic light emitting device, an appropriate energy level and a band gap are formed, thereby increasing excitons in the light emitting region. An increase in excitons in the light emitting region means that the driving voltage and efficiency of the device are increased.

In an exemplary embodiment of the present application, L in Formula 1 is a substituted or unsubstituted arylene group; Or it may be a substituted or unsubstituted heteroarylene group.

In another exemplary embodiment, L is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or it may be a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

In another exemplary embodiment, L is a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or it may be a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

In another exemplary embodiment, L is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or it may be a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

In another exemplary embodiment, L is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted fluorenylene group; a substituted or unsubstituted carbazolnylene group; A substituted or unsubstituted dibenzofurannylene group; Or it may be a substituted or unsubstituted dibenzothiophennylene group.

In another exemplary embodiment, L is a phenylene group; biphenylene group; naphthylene group; a fluorenylene group substituted with an alkyl group having 1 to 10 carbon atoms; a carbazolnylene group substituted with an aryl group having 6 to 20 carbon atoms; dibenzofurannylene group; Or it may be a dibenzothiophennylene group.

In another exemplary embodiment, L is a phenylene group; biphenylene group; naphthylene group; a fluorenylene group substituted with a methyl group; a carbazolnylene group substituted with a phenyl group; dibenzofurannylene group; Or it may be a dibenzothiophennylene group.

In another exemplary embodiment, L is a phenylene group; biphenylene group; naphthylene group; 9,9-dimethyl-9H-(9,9-dimethyl-9H-)fluorenylene group; 9-phenyl-9H-(9-phenyl-9H-)carbazolnylene group; dibenzofurannylene group; Or it may be a dibenzothiophennylene group.

In another exemplary embodiment, L is a phenylene group.

In another exemplary embodiment, L is a biphenylene group.

In another exemplary embodiment, L is a naphthylene group.

In another exemplary embodiment, L is a 9,9-dimethyl-9H-(9,9-dimethyl-9H-)fluorenylene group.

In another exemplary embodiment, L is a 9-phenyl-9H-(9-phenyl-9H-)carbazolnylene group.

In another exemplary embodiment, L is a dibenzofurannylene group.

In another exemplary embodiment, L is a dibenzothiophennylene group.

In an exemplary embodiment of the present application, L ₁ and L ₂ of Formula 1 are the same as or different from each other, and each independently, a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or it may be a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present application, L ₁ and L ₂ of Formula 1 are the same as or different from each other, and each independently, a direct bond; It may be a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

In another exemplary embodiment, the L ₁ and L ₂ are the same as or different from each other, and each independently, a direct bond; Or it may be a substituted or unsubstituted phenylene group.

In an exemplary embodiment of the present application, X ₁ and X ₂ of Formula 1 are the same as or different from each other, and each independently O; or S.

In the exemplary embodiment of the present application, both X ₁ and X ₂ are O.

In an exemplary embodiment of the present application, X ₁ and X ₂ are both S.

In an exemplary embodiment of the present application, X ₁ and X ₂ of Formula 1 are different from each other, and each independently O; or S.

In an exemplary embodiment of the present application, X ₁ is O, and X ₂ is S.

In an exemplary embodiment of the present application, X ₁ is S, and X ₂ is O.

In an exemplary embodiment of the present application, R _p and R _q of Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present application, R _p and R _q are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted C 6 to C 40 aryl group; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

In an exemplary embodiment of the present application, R _p and R _q are both hydrogen.

In the exemplary embodiment of the present application, in Formula 1, b and c are each an integer of 0 to 4, and when b and c are each 2 or more, the substituents in parentheses may be the same or different from each other.

In the exemplary embodiment of the present application, b is 4.

In an exemplary embodiment of the present application, b is 3.

In the exemplary embodiment of the present application, b is 2.

In the exemplary embodiment of the present application, b is 1.

In the exemplary embodiment of the present application, b is 0.

When b is 2 or more, the substituents in parentheses are the same as or different from each other.

In the exemplary embodiment of the present application, c is 4.

In the exemplary embodiment of the present application, c is 3.

In the exemplary embodiment of the present application, c is 2.

In an exemplary embodiment of the present application, c is 1.

In the exemplary embodiment of the present application, c is 0.

When c is 2 or more, the substituents in parentheses are the same as or different from each other.

In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of Chemical Formulas 1-1 to 1-3 below.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3, the definition of each substituent is the same as in Formula 1 above.

In the exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of Chemical Formulas 2 to 6 below.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

In Formulas 2 to 6, the definition of each substituent is the same as in Formula 1 above.

In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of Chemical Formulas 7 to 10 below.

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

In Formulas 7 to 10,

X ₁ , X ₂ , L ₁ , L ₂ , n, m, Ar ₁ , and Ar ₂ have the same definitions as in Formula 1,

Y ₁ is O; S; CR ₁ R ₂ or NR _a ,

The R ₁ and R ₂ are the same as or different from each other, and each independently is an alkyl group having 1 to 10 carbon atoms,

Wherein R _a is an aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present application, Y ₁ of Formulas 7 to 10 is O; S; CR ₁ R ₂ or NR _a .

In an exemplary embodiment of the present application, R ₁ and R ₂ may be the same as or different from each other, and each independently may be an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present application, R ₁ and R ₂ are both methyl groups.

In an exemplary embodiment of the present application, R _a may be an aryl group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present application, R _a is a phenyl group.

In an exemplary embodiment of the present application, Y ₁ is is O.

In an exemplary embodiment of the present application, Y ₁ is is S.

In an exemplary embodiment of the present application, Y ₁ is CR ₁ R ₂ and R ₁ and R ₂ are both methyl groups.

In an exemplary embodiment of the present application, Y ₁ is CR _a , wherein R _a is a phenyl group.

In an exemplary embodiment of the present application, Ar ₁ and Ar ₂ of Formula 1 are the same as or different from each other, and each independently a substituted or unsubstituted C 6 to C 60 aryl group; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present application, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

In an exemplary embodiment of the present application, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or it may be a substituted or unsubstituted spiro [fluorene-9,9-xanthene] (spiro [fluorene-9,9'-xanthene]) group.

In another exemplary embodiment, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently represents a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a cyano group (-CN). a phenyl group unsubstituted or substituted with one or more selected from the group consisting of; a biphenyl group unsubstituted or substituted with one or more selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a cyano group (-CN); a terphenyl group unsubstituted or substituted with one or more selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a cyano group (-CN); a naphthyl group unsubstituted or substituted with one or more selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a cyano group (-CN); spirobifluorenyl group; a fluorenyl group unsubstituted or substituted with one or more selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 10 tins; a substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or it may be a substituted or unsubstituted spiro [fluorene-9,9-xanthene] (spiro [fluorene-9,9'-xanthene]) group.

In the exemplary embodiment of the present application, Ar ₁ may be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and Ar ₂ may be a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

In another exemplary embodiment of the present application, Ar ₁ may be a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, and Ar ₂ may be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

When a compound in which one of Ar ₁ and Ar ₂ of Formula 1 is an aryl group and the other is a heteroaryl group is used in the organic material layer of the organic light emitting device, the driving and efficiency of the organic light emitting device are more excellent.

In the exemplary embodiment of the present application, both Ar ₁ and Ar ₂ may be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

When the compound in which both Ar ₁ and Ar ₂ of Formula 1 are aryl groups is used in the organic material layer of the organic light emitting device, the lifespan of the organic light emitting device is more excellent.

In the exemplary embodiment of the present application, both Ar ₁ and Ar ₂ may be a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

When the compound in which both Ar ₁ and Ar ₂ of Formula 1 are heteroaryl groups is used in the organic material layer of the organic light emitting device, the driving and efficiency of the organic light emitting device are more excellent.

In the exemplary embodiment of the present application, in Formula 1, a is an integer of 1 or 2, and when a is 2, the substituents in parentheses may be the same or different from each other.

In the exemplary embodiment of the present application, a is 1.

In the exemplary embodiment of the present application, a is 2. When a is 2, the substituents in parentheses are the same as or different from each other.

In the exemplary embodiment of the present application, in Formula 1, m and n are each an integer of 0 to 2, and when m and n are each 2, the substituents in parentheses may be the same or different from each other.

In the exemplary embodiment of the present application, m is 0.

In an exemplary embodiment of the present application, m is 1.

In an exemplary embodiment of the present application, m is 2. When m is 2, the substituents in parentheses are the same as or different from each other.

In the exemplary embodiment of the present application, n is 0.

In the exemplary embodiment of the present application, n is 1.

In an exemplary embodiment of the present application, n is 2. When n is 2, the substituents in parentheses are the same as or different from each other.

In an exemplary embodiment of the present application, Chemical Formula 1 provides a heterocyclic compound represented by any one of the following compounds.

In addition, by introducing various substituents into the structure of Formula 1, a heterocyclic compound having intrinsic properties of the introduced substituents can be synthesized. For example, by introducing into the core structure a substituent mainly used for 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 manufacturing an organic light emitting device, the conditions required for each organic material layer are satisfied. substances can be synthesized.

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

On the other hand, 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 by a multi-step chemical reaction. Some intermediate compounds are prepared first, and a heterocyclic 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 to be described later.

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", "OLED (Organic Light Emitting Diodes)", "OLED device", and "organic electroluminescent device".

In an exemplary embodiment of the present application, the first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one organic material layer includes the heterocyclic compound represented by Formula 1 above. provides

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

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

In the exemplary embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the blue organic light emitting device.

In another exemplary embodiment of the present application, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the green organic light emitting device.

In another exemplary embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the red organic light emitting device.

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

The organic light emitting device of the present application may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described 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 refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present application may have a single-layer structure, but 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 hole auxiliary layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. 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 application, the organic material layer may include an electron transport layer, and the electron transport layer may include the heterocyclic compound. When the heterocyclic compound is used in the electron transport layer, an appropriate energy level and a band gap are formed, so that excitons in the light emitting region are increased, thereby improving the driving voltage and efficiency of the device. In addition, since it has a high T1 value, it is possible to realize a device having a long lifespan with excellent hole transport ability and thermal stability.

In the organic light emitting device of the present application, the organic material layer may include a hole auxiliary layer, and the hole auxiliary layer may include the heterocyclic compound. When the heterocyclic compound is used in the hole auxiliary layer, it is possible to more effectively tune the energy level and the emission wavelength between the light emitting layer and the hole transport layer by preventing electrons from passing from the light emitting layer to the hole transport layer, so that the color purity of the device is reduced is improved

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

1 to 3 illustrate the stacking order of the electrode and the organic material layer of the organic light emitting device according to an exemplary embodiment of the present application. However, it is not intended that the scope of the present application be limited by these drawings, and the structure of an organic light emitting device known in the art may also be applied to the present application.

Referring 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 illustrated. 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 in which the organic material layer is multi-layered. The organic light emitting diode according to FIG. 3 includes a hole injection layer 301 , a hole transport layer 302 , a light emitting layer 303 , a hole blocking layer 304 , an electron transport layer 305 , and an electron injection layer 306 . However, the scope of the present application is not limited by such a laminated structure, and if necessary, the remaining layers except for the light emitting layer may be omitted, and other necessary functional layers may be further added.

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

In addition, an organic light emitting device according to an exemplary embodiment of the present application includes a first electrode; a first stack provided on the first electrode and including a first light emitting layer; a charge generation layer provided on the first stack; a second stack provided on the charge generation layer and including a second light emitting layer; and a second electrode provided on the second stack.

In this case, the charge generating layer may include a heterocyclic compound represented by Formula 1 above. When the heterocyclic compound is used in the charge generating layer, driving, efficiency, and lifespan of the organic light emitting diode may be improved.

In addition, the first stack and the second stack may each independently further include one or more of the aforementioned hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer, and the like.

As an organic light emitting device according to an exemplary embodiment of the present application, an organic light emitting device having a two-stack tandem structure is exemplarily 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 the organic light emitting device according to an exemplary embodiment of the present application, materials other than the compound of Formula 1 are exemplified below, but these are for illustration only and not to limit the scope of the present application, and are known in the art. materials can be substituted.

Materials having a relatively large work function may be used as the anode material, and transparent conductive oxides, metals, conductive polymers, or the like may be used. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as 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.

Materials having a relatively low work function may be used as the anode material, and a metal, metal oxide, conductive polymer, or the like 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; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

As the hole injection material, a known hole injection material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or Advanced Material, 6, p.677 (1994). starburst-type amine derivatives such as tris(4-carbazolyl-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 or poly( 3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), polyaniline/Camphor sulfonic acid or polyaniline/ poly(4-styrenesulfonate) (Polyaniline/Poly(4-styrenesulfonate)) and the like can be used.

As the hole transport material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, etc. may be used, and a low molecular weight or high molecular material may be used.

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

As the electron injection 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 the light emitting material, and if necessary, two or more light emitting materials may be mixed and used. In this case, two or more light emitting materials may be deposited and used as individual sources, or may be premixed and deposited as a single source for use. In addition, although a fluorescent material can be used as a light emitting material, it can also be used as a phosphorescent material. As the light-emitting material, a material that emits light by combining holes and electrons respectively injected from the anode and the cathode may be used, but materials in which the host material and the dopant material together participate in light emission may be used.

When mixing and using a host of a light emitting material, a host of the same series may be mixed and used, or a host of different series may be mixed and used. For example, any two or more types of n-type host material and p-type host material may be selected and used as the host material of the light emitting layer.

In the organic light emitting device of the present application, the organic material layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound.

In the organic light emitting device of the present application, the organic material layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound as a host material of the light emitting material.

In the organic light emitting device of the present application, the light emitting layer may include two or more host materials, and at least one of the two or more host materials may include the heterocyclic compound as a host material of the light emitting material.

In the organic light emitting device of the present application, the light emitting layer may be used by pre-mixing two or more host materials, and at least one of the two or more host materials uses the heterocyclic compound as a host material of the light emitting material may include

The pre-mixed means that the light emitting layer is mixed with two or more host materials before depositing them on the organic material layer and put it in one park.

In the organic light emitting device of the present application, the light emitting layer may include two or more host materials, each of the two or more host materials includes one or more p-type host materials and n-type host materials, and at least one of the host materials One may include the heterocyclic compound as a host material of the light emitting material. In this case, driving, efficiency, and lifespan of the organic light emitting diode may be improved.

In the organic light emitting device of the present application, the light emitting layer may include the heterocyclic compound and the heterocyclic compound represented by Chemical Formula 11 below.

[Formula 11]

In the above formula (11),

L ₁₁ and L ₁₂ are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroarylene group,

X ₁₁ is O; S; or CR _b R _c , wherein R _b and R _c are the same as or different from each other, and each independently represents a substituted or unsubstituted C 1 to C 10 alkyl group,

Y ₁₁ to Y ₁₅ are the same as or different from each other, and each independently represents N or CR _d , and at least one of Y ₁₁ to Y ₁₅ is N,

each R _d is the same as or different from each other, and each independently represents hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted C 2 to C 60 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C 6 to C 60 aromatic hydrocarbon ring or a substituted or unsubstituted C 2 to form a heterocyclic ring of 60;

Ar ₁₁ is hydrogen; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

p and q are respectively 0 or 1.

When the heterocyclic compound represented by Formula 11 is used together with the heterocyclic compound represented by Formula 1 in the light emitting layer, an exciplex may be formed to improve device performance.

In an exemplary embodiment of the present application, L ₁₁ and L ₁₂ of Formula 11 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted C 2 to C 20 heteroarylene group.

In an exemplary embodiment of the present application, L ₁₁ and L ₁₂ are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

In an exemplary embodiment of the present application, L ₁₁ and L ₁₂ are the same as or different from each other, and each independently a direct bond; phenylene group; or a naphthylene group.

In an exemplary embodiment of the present application, X ₁₁ of Formula 11 is O; S; or CR _b R _c , wherein R _b and R _c may be the same as or different from each other, and may each independently be a substituted or unsubstituted C 1 to C 10 alkyl group.

In an exemplary embodiment of the present application, the X ₁₁ is O; S; or CR _b R _c , wherein R _b and R _c are all methyl groups.

In an exemplary embodiment of the present application, X ₁₁ is O.

In the exemplary embodiment of the present application, X ₁₁ is S.

In an exemplary embodiment of the present application, X ₁₁ is CR _b R _c , and R _b and R _c are all methyl groups.

In an exemplary embodiment of the present application, the Y ₁₁ , Y ₁₃ and At least one of Y ₁₅ is N, wherein Y ₁₂ and Y ₁₄ is is CR _d .

In an exemplary embodiment of the present application, the Y ₁₁ , Y ₁₃ and At least one of Y ₁₅ is N, the remainder other than N and Y ₁₂ and Y ₁₄ is is CR _d .

In an exemplary embodiment of the present application, the Y ₁₁ , Y ₁₃ and At least one of Y ₁₅ is N and the remainder other than N is CH, wherein Y ₁₂ and Y ₁₄ is is CR _d .

In an exemplary embodiment of the present application, R _d Is hydrogen; heavy hydrogen; a substituted or unsubstituted C6-C20 aryl group; and a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to a substituted or unsubstituted C6 to C10 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to form a heterocyclic ring of 10.

In an exemplary embodiment of the present application, R _d Is hydrogen; heavy hydrogen; a substituted or unsubstituted C6-C20 aryl group; and a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to a substituted or unsubstituted C6 to C10 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to form a heterocyclic ring of 10.

In an exemplary embodiment of the present application, R _d Is hydrogen; heavy hydrogen; And two or more groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or adjacent to each other are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 10 carbon atoms.

In an exemplary embodiment of the present application, R _d Is hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; And two or more groups selected from the group consisting of a substituted or unsubstituted biphenyl group, or adjacent to each other are bonded to each other to form a substituted or unsubstituted benzene ring.

In an exemplary embodiment of the present application, R _d Is hydrogen; heavy hydrogen; phenyl group; And two or more groups selected from the group consisting of a biphenyl group, or adjacent to each other are bonded to each other to form a benzene ring.

In the exemplary embodiment of the present application, Ar ₁₁ of Formula 11 is hydrogen; a substituted or unsubstituted C 6 to C 40 aryl group; Or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

In the exemplary embodiment of the present application, Ar ₁₁ of Formula 11 is hydrogen; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C 2 to C 20 heteroaryl group.

In an exemplary embodiment of the present application, Ar ₁₁ is hydrogen; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted pyridine group.

In an exemplary embodiment of the present application, Ar ₁₁ is hydrogen; phenyl group; biphenyl group; or a pyridine group.

In an exemplary embodiment of the present application, Chemical Formula 11 provides a heterocyclic compound represented by any one of the following compounds.

In an exemplary embodiment of the present application, the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 11 may be used as a host material.

In an exemplary embodiment of the present application, in an exemplary embodiment of the present application, there is provided a composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 11 .

The weight ratio of the heterocyclic compound represented by Formula 1 in the composition to the heterocyclic compound represented by Formula 11 may be 1: 10 to 10: 1, 1: 8 to 8: 1, and 1: 5 to 5: 1 may be, and may be 1: 2 to 2: 1, but is not limited thereto.

The organic light emitting device according to the exemplary embodiment of the present application may be a top emission type, a back emission type, or a double side emission type depending on a material used.

The heterocyclic compound according to an exemplary embodiment of the present application 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, the present specification will be described in more detail through examples, but these are only for illustrating the present application and not for limiting the scope of the present application.

[Production Example 1]

<Preparation of compound 4>

1) Preparation of Intermediate 4-3

4-4 (40.0 g, 298 mmol) was placed in Et ₂ O (400 mL). n-BuLi (143 mL, 358 mmol) was slowly added under a nitrogen atmosphere, followed by stirring at room temperature for 20 minutes. The mixture was stirred at 40 °C for 6 hours and cooled to room temperature. CuCl ₂ (40.1 g, 298 mmol) was added in 4 portions, followed by stirring at 40 °C for 6 hours. After cooling half of the solution to room temperature, it was filtered. The filtrate was washed with HCl, H ₂ O, and dried over MgSO ₄ . After concentration under reduced pressure, it was recrystallized and purified with toluene to obtain Intermediate 4-3 (25.4 g, 64%).

2) Preparation of Intermediate 4-2

Intermediate 4-3 (20.0 g, 75.1 mmol) was dissolved in AcOH at room temperature, and then the temperature was raised to 60 °C. After adding HNO ₃ :AcOH (6.5/26 mL) solution, the mixture was stirred at 60° C. for 1 hour. It was cooled to room temperature, filtered, and washed with H ₂ O and MeOH to obtain Intermediate 4-2 (22.5 g, 96%).

3) Preparation of Intermediate 4-1

Intermediate 4-2 (22.5 g, 72.3 mmol) and PPh ₃ (47.4 g, 181 mmol) were added to 1,2-DCB (230 mL), followed by stirring at 200 °C for 14 hours. After cooling to room temperature and filtering with silica gel, it was washed with Toluene and Hexane to obtain Intermediate 4-1. (12.1 g, 60%)

4) Preparation of compound 4

Intermediate 4-1 (4.15 g, 14.9 mmol), N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine ( 7.08 g, 14.9 mmol), Pd ₂ dba ₃ (0.68 g, 0.75 mmol), P(t-Bu) ₃ (0.75 mL, 1.49 mmol), t-BuONa (2.86 g, 29.8 mmol) in xylene at 160 °C was stirred for 4 hours. After cooling to room temperature, it was allowed to stand for 12 hours and the resulting solid was filtered. After silica gel filter, the resulting solid was concentrated under reduced pressure and filtered to obtain compound 4 (7.59 g, 75%).

In Preparation Example 1, in place of the N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine A in Table 1 Except for using , the following compound was synthesized in the same manner as in the preparation of compound 4.

[Production Example 2]

<Preparation of compound 184>

1) Preparation of Intermediate 184-2

184-3 (20.0 g, 79.9 mmol) was dissolved in AcOH at room temperature, and then the temperature was raised to 60 °C. After adding HNO ₃ :AcOH (7.0/28 mL) solution, the mixture was stirred at 60° C. for 3 hours. It was cooled to room temperature, filtered, and washed with H ₂ O and MeOH to obtain Intermediate 184-2 (17.2 g, 73%).

2) Preparation of Intermediate 184-1

Intermediate 184-2 (17.3 g, 58.6 mmol) and PPh ₃ (38.4 g, 146 mmol) were added to 1,2-DCB (170 mL), followed by stirring at 200 °C for 18 hours. After cooling to room temperature and filtering with silica gel, it was washed with Toluene and Hexane to obtain Intermediate 184-1. (8.49 g, 55%)

3) Preparation of compound 184

Intermediate 184-1 (5.00 g, 19.0 mmol), N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine ( 9.05 g, 19.0 mmol), Pd ₂ dba ₃ (0.87 g, 0.95 mmol), P(t-Bu) ₃ (0.96 mL, 1.90 mmol), t-BuONa (3.65 g, 38.0 mmol) in xylene at 160 ° C. was stirred for 8 hours. After cooling to room temperature, it was allowed to stand for 12 hours and the resulting solid was filtered. The resulting solid was filtered after silica gel filter and concentrated under reduced pressure to obtain compound 184 (8.39 g, 67%).

A of Table 2 below instead of N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine in Preparation Example 2 Except for using , the following compound was synthesized in the same manner as in the preparation of compound 184.

[Production Example 3]

<Preparation of compound 246>

1) Preparation of Intermediate 246-2

246-3 (20.0 g, 85.4 mmol) was dissolved in AcOH at room temperature, and then the temperature was raised to 60 °C. After adding HNO ₃ :AcOH (7.5/30 mL) solution, the mixture was stirred at 60° C. for 18 hours. It was cooled to room temperature, filtered, and washed with H ₂ O and MeOH to obtain Intermediate 246-2 (15.2 g, 64%).

2) Preparation of Intermediate 246-1

Intermediate 246-2 (15.2 g, 54.4 mmol) and PPh ₃ (35.7 g, 136 mmol) were added to 1,2-DCB (150 mL), followed by stirring at 200 °C for 18 hours. After cooling to room temperature and filtering with silica gel, it was washed with Toluene and Hexane to obtain Intermediate 246-1. (6.73 g, 50%)

3) Preparation of compound 246

Intermediate 246-1 (5.00 g, 20.2 mmol), N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine ( 9.63 g, 20.2 mmol), Pd ₂ dba ₃ (0.92 g, 1.01 mmol), P(t-Bu) ₃ (1.02 mL, 1.90 mmol), t-BuONa (3.88 g, 40.4 mmol) in xylene at 160 °C was stirred for 8 hours. After cooling to room temperature, it was allowed to stand for 12 hours and the resulting solid was filtered. The resulting solid was filtered after silica gel filter and concentrated under reduced pressure to obtain compound 246 (9.22 g, 71%).

In Preparation Example 3, in place of the N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine A in Table 3 Except for using , the following compound was synthesized in the same manner as in the preparation of compound 246.

Compounds were prepared in the same manner as in Preparation Examples, and the synthesis confirmation results are shown in Tables 4 and 5 below. Table 4 below is a measurement value of ¹ H NMR (CDCl ₃ , 300Mz), and Table 5 below is a measurement value of an FD-mass spectrometer (FD-MS: Field desorption mass spectrometry).

[Experimental example]

<Experimental Example 1>

1) Fabrication of an organic light emitting device

의 두께로 인듐틴옥사이드(ITO, Indium Tinoxide)가 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 아세톤, 메탄올, 이소프로필 알코올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV(Ultraviolet) 세정기에서 UV를 이용하여 5분간 UVO(Ultraviolet Ozone)처리하였다. 이후 기판을 플라즈마 세정기(PT)로 이송시킨 후, 진공상태에서 ITO 일함수 및 잔막 제거를 위해 플라즈마 처리를 하여, 유기증착용 열증착 장비로 이송하였다.1,500

A glass substrate coated with a thin film of indium tin oxide (ITO, Indium Tinoxide) to a thickness of was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic washing was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., dried, and then UVO (Ultraviolet Ozone) treatment was performed for 5 minutes using UV in a UV (Ultraviolet) washer. After transferring the substrate to a plasma cleaner (PT), plasma treatment was performed to remove the ITO work function and residual film in a vacuum state, and then transferred to a thermal deposition equipment for organic deposition.

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

A light emitting layer was deposited thereon by thermal vacuum deposition as follows. For the light emitting layer, 3 wt% of (piq) ₂ (Ir)(acac) was doped into the host using (piq) ₂ (Ir)(acac) as a red phosphorescent dopant and the compounds shown in Table 6 below as a red host, and 500Å was deposited. Thereafter, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) was deposited at 60 Å as a hole blocking layer, and Alq ₃ was deposited at 200 Å as an electron transport layer thereon. Finally, lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode is deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode. A light emitting device was manufactured (Comparative Examples 1 to 4 and Examples 1 to 20).

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

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 M7000 of McScience, and the reference luminance was 6,000 cd through the life instrumentation measuring device (M6000) manufactured by McScience with the measurement result. When /m ² , T ₉₀ was measured. The T ₉₀ denotes a lifetime (unit: h, time) that is 90% of the initial luminance.

The characteristics of the organic light emitting diode of the present invention are shown in Table 6 below.

As can be seen from Table 6, in the case of Examples 1 to 20, in which the compound corresponding to Chemical Formula 1 was used as the light emitting layer of the organic light emitting device, the lifespan, efficiency, and driving voltage were lower than those of Comparative Examples 1 to 4, which is not the case. It showed an excellent effect in properties. That is, it was confirmed that it can be used as a red host more suitable than the existing carbazole host, and can help improve lifespan efficiency and driving voltage.

<Experimental Example 2>

1) Fabrication of an organic light emitting device (Red N+P mixed host)

A glass substrate coated with a thin film of 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 a solvent such as acetone, methanol, isopropyl alcohol, etc., dried, and UVO-treated for 5 minutes using UV in a UV washer. Thereafter, the substrate was transferred to a plasma cleaner (PT), and then plasma-treated to remove the ITO work function and residual film in a vacuum state, and transferred to a thermal deposition equipment for organic deposition.

A hole injection layer 2-TNATA (4,4′,4′′-Tris[2-naphthyl(phenyl)amino]triphenylamine) 100Å and a hole transport layer NPB (N,N′- Di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine) 1000Å was formed.

A light emitting layer was deposited thereon by thermal vacuum deposition as follows. The light emitting layer was deposited as a red host at 400 Å from one source after preliminary mixing of two types of compounds as shown in Table 7, and a red phosphorescent dopant was deposited by doping 3 wt % of (piq) ₂ (Ir)(acac). After that, 60 Å of BCP was deposited as a hole blocking layer, and 200 Å of Alq ₃ was deposited thereon as an electron transporting layer. Finally, lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode is deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode. Light-emitting devices were manufactured (Examples 21 to 65 and Comparative Examples 5 to 9).

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

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 M7000 of McScience, and the reference luminance was 6,000 cd through the life instrumentation measuring device (M6000) manufactured by McScience with the measurement result. When /m ² , T ₉₀ was measured. The T ₉₀ denotes a lifetime (unit: h, time) that is 90% of the initial luminance.

The characteristics of the organic light emitting diode of the present invention are shown in Table 7 below.

As can be seen from Table 7, when the compound according to the present application was used as the light emitting layer of the organic light emitting device, it was confirmed that the compound exhibited superior effects in terms of lifespan, efficiency, and driving voltage characteristics compared to the case where it was not.

That is, it was found that by using the compound according to the present application in the emission layer of the organic light emitting device, the energy level and the emission wavelength between the emission layer and the hole transport layer can be more effectively tuned.

In addition, as can be seen in Table 7, it was confirmed that when the light emitting layer of the organic light emitting device contains the n-type host material compound and the compound according to the present application at the same time, better efficiency and lifespan effect are exhibited.

From this result, it could be expected that an exciplex phenomenon would occur when the compound as the n-type host material and the compound according to the present application as the p-type host material were simultaneously included. In particular, an exciplex phenomenon (hereinafter referred to as an exciplex phenomenon of an N+P compound) that occurs when a compound that is an n-type host material and a p-type host material is used at the same time is a donor through electron exchange between two molecules It means emitting energy equal to the HOMO level of the p-host, which is the (donor), and the LUMO level, of the n-host, which is the acceptor.

The exciplex phenomenon of this N + P compound is higher than the case of using compound 68 and n-Host A in FIGS. 5 to 7, respectively, when the compound 68 and n-Host A are used at the same time ( Photo Luminescence, PL) results were confirmed by shifting to a longer wavelength.

Specifically, the following FIGS. 5 to 7 show PL results when Compound 68 was used, PL results when n-Host A was used, and PL results when Compound 68 and n-Host A were used simultaneously.

Similarly, the case of using compound 4 and n-Host B at the same time compared to the case of using compound 4 and n-Host B through FIGS. 8 to 10 below due to the exciplex phenomenon of the N+P compound, light It was confirmed that the luminescence (Photo Luminescence, PL) result shifted to a longer wavelength.

Specifically, the following FIGS. 8 to 10 show PL results when Compound 4 was used, PL results when n-Host B was used, and PL results when Compound 4 and n-Host B were used simultaneously.

That is, from FIGS. 5 to 10, when a donor (p-host) having good hole transport ability and an acceptor (n-host) having good electron transport ability are used as hosts of the emission layer, holes are injected into the p-host, and electrons are n Because it is injected into -host, it was found that the driving voltage can be lowered, thereby helping to improve the lifespan.

5 to 10, the horizontal axis means wavelength, and the vertical axis means sensitivity.

<Experimental Example 3>

(1) Fabrication of an organic light emitting device

The transparent electrode ITO thin film obtained from glass for an organic light emitting device (manufactured by Samsung-Corning) was ultrasonically washed for 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water sequentially, and then placed in isopropanol and stored before use. Next, the ITO substrate is installed in the substrate folder of the vacuum deposition equipment, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine ( 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was added.

Then, after evacuating the chamber until the vacuum degree reached 10 ^-6 torr, a current was applied to the cell to evaporate 2-TNATA, and a 600 Å-thick hole injection layer was deposited on the ITO substrate. The following N,N'-bis(α-naphthyl)--N,N'-diphenyl-4,4'-diamine (N,N'-bis(α-naphthyl)-N ,N'-diphenyl-4,4'-diamine: NPB) was put, and a current was applied to the cell to evaporate and deposit a hole transport layer with a thickness of 300 Å on the hole injection layer. Thereafter, a hole auxiliary layer having a thickness of 50 Å was formed on the hole transport layer by using the compounds shown in Table 8 below.

A red light-emitting material having the following structure was deposited as a light-emitting layer thereon. Specifically, a red host material, CBP, was vacuum-deposited to a thickness of 200 Å in one cell in the vacuum deposition equipment, and a red phosphorescent dopant was deposited by doping 3 wt% of (piq) ₂ (Ir)(acac).

Subsequently, Alq ₃ was deposited to a thickness of 200 Å as an electron transport layer thereon. As an electron injection layer, lithium fluoride (LiF) was deposited to a thickness of 10 Å, and an Al cathode had a thickness of 1,000 Å to prepare an organic light emitting device (Comparative Examples 10 to 12 and Examples 66 to 85).

Meanwhile, all organic compounds required for manufacturing an organic light emitting device were vacuum sublimated and purified under 10 ^-6 to 10 ^-8 torr for each material, respectively, and used for manufacturing the organic light emitting device.

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 M7000 of McScience, and the reference luminance was 6,000 cd through the life instrumentation measuring device (M6000) manufactured by McScience with the measurement results. When /m ² , T ₉₀ was measured. Here, T ₉₀ denotes a lifetime (unit: h, time) that is 90% of the initial luminance.

The measured characteristics of the organic light emitting diode of the present invention are shown in Table 8 below.

From Table 8, in the case of the organic light emitting devices of Examples 66 to 85 using the compound according to the present application when forming the hole auxiliary layer, Comparative Examples 10 to 12 without using the compound according to the present application when forming the hole auxiliary layer It was confirmed that the driving voltage, luminous efficiency, and lifespan were superior to organic light emitting devices.

Through this, when the compound according to the present application is used as a hole auxiliary layer, the hole auxiliary layer can more effectively perform a role of preventing electrons from passing from the light emitting layer to the hole transport layer like the electron blocking layer, and also the light emitting layer and the hole transport layer It was found that the color purity was improved by more effectively tuning the energy level and the emission wavelength between them.

100: substrate
200: positive electrode
300: organic 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 (12)

A heterocyclic compound represented by the following formula (1):
[Formula 1]

In Formula 1,
L is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroarylene group,
L ₁ And L ₂ Are the same as or different from each other, each independently, a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms,
X ₁ and X ₂ are the same as or different from each other, each independently O or S,
R _p and R _q are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituted or unsubstituted C 6 to C 60 aryl group; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
a is an integer of 1 or 2, and when a is 2, the substituents in parentheses are the same or different from each other,
b and c are each an integer of 0 to 4, and when b and c are each 2 or more, the substituents in parentheses are the same as or different from each other,
m and n are each an integer of 0 to 2, and when m and n are each 2, the substituents in parentheses are the same as or different from each other. The method according to claim 1,
The "substituted or unsubstituted" refers to a linear or branched alkyl group having 1 to 60 carbon atoms; a linear or branched alkenyl group having 2 to 60 carbon atoms; a linear or branched alkynyl group having 2 to 60 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 60 carbon atoms; a monocyclic or polycyclic heterocycloalkyl group having 2 to 60 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 60 carbon atoms; a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms; silyl group; a phosphine oxide group; and a heterocyclic compound that is substituted or unsubstituted with one or more substituents selected from the group consisting of an amine group, or substituted or unsubstituted with a substituent to which two or more substituents selected from the above exemplified substituents are connected. The method according to claim 1,
The above formula 1 is a heterocyclic compound represented by any one of the following formulas 2 to 6:
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

In Formulas 2 to 6, the definition of each substituent is the same as in Formula 1 above. The method according to claim 1,
The above formula 1 is a heterocyclic compound represented by any one of the following formulas 7 to 10:
[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

In Formulas 7 to 10,
X ₁ , X ₂ , L ₁ , L ₂ , n, m, Ar ₁ , and Ar ₂ have the same definitions as in Formula 1,
Y ₁ is O; S; CR ₁ R ₂ or NR _a ,
The R ₁ and R ₂ are the same as or different from each other, and each independently is an alkyl group having 1 to 10 carbon atoms,
Wherein R _a is an aryl group having 6 to 20 carbon atoms. The method according to claim 1,
Formula 1 is a heterocyclic compound represented by any one of the following compounds:

a first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the heterocyclic compound according to any one of claims 1 to 5 organic light emitting device. 7. The method of claim 6,
The organic material layer includes an emission layer, and the emission layer includes the heterocyclic compound. 8. The method of claim 7
The light emitting layer may be used by pre-mixing two or more host materials, and at least one of the two or more host materials includes the heterocyclic compound as a host material of the light emitting material. 8. The method of claim 7
The light emitting layer is an organic light emitting device including the heterocyclic compound and the heterocyclic compound represented by the following Chemical Formula 11:
[Formula 11]

In the above formula (11),
L ₁₁ and L ₁₂ are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroarylene group,
X ₁₁ is O; S; or CR _b R _c , wherein R _b and R _c is the same as or different from each other, and each independently represents a substituted or unsubstituted C 1 to C 10 alkyl group,
Y ₁₁ to Y ₁₅ are the same as or different from each other, and each independently represents N or CR _d , and at least one of Y ₁₁ to Y ₁₅ is N,
each R _d is the same as or different from each other, and each independently represents hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted C 2 to C 60 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C 6 to C 60 aromatic hydrocarbon ring or a substituted or unsubstituted C 2 to form a heterocyclic ring of 60;
Ar ₁₁ is hydrogen; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
p and q are each 0 or 1. The method according to claim 6, wherein the organic light emitting device comprises: a first electrode; a first stack provided on the first electrode and including a first light emitting layer; a charge generation layer provided on the first stack; An organic light emitting diode comprising: a second stack provided on the charge generation layer and including a second light emitting layer; and a second electrode provided on the second stack. A composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 11 according to claim 1;
[Formula 11]

In the above formula (11),
L ₁₁ and L ₁₂ are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroarylene group,
X ₁₁ is O; S; or CR _b R _c , wherein R _b and R _c is the same as or different from each other, and each independently represents a substituted or unsubstituted C 1 to C 10 alkyl group,
Y ₁₁ to Y ₁₅ are the same as or different from each other, and each independently represents N or CR _d , and at least one of Y ₁₁ to Y ₁₅ is N,
each R _d is the same as or different from each other, and each independently represents hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted C 2 to C 60 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C 6 to C 60 aromatic hydrocarbon ring or a substituted or unsubstituted C 2 to form a heterocyclic ring of 60;
Ar ₁₁ is hydrogen; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
p and q are each 0 or 1. 12. The method of claim 11,
In the composition, the weight ratio of the heterocyclic compound represented by Formula 1 to the heterocyclic compound represented by Formula 11 is 1:10 to 10:1. The composition for an organic material layer of an organic light emitting device.

Images