KR20220041305A - 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. The heterocyclic compound can be used alone as a light emitting material, or can be used as a host material or a dopant material of the light emitting layer.

Description

Heterocyclic compound, organic light emitting device comprising same, manufacturing method thereof, and composition for organic material layer

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

The organic light emitting device is a type of self-emission type display device, and has 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-based 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.

Korean Patent Publication No. 10-2014-0106631

An object of the present invention is to provide a heterocyclic compound capable of imparting a low driving voltage, excellent luminous efficiency, and excellent lifespan characteristics to an organic light emitting device.

Another object of the present invention is to provide an organic light emitting device including the heterocyclic compound and a method for manufacturing the same.

Another object of the present invention is to provide a composition for an organic material layer comprising the heterocyclic compound.

The present invention provides a heterocyclic compound represented by the following formula (1).

[Formula 1]

In Formula 1,

X is O or S;

R1 to R14 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)R101R202; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other combine with each other 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 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,

R15 is a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or -Si(Ar1) ₃ , wherein each Ar1 included in (Ar1) ₃ is the same as each other. or different, each independently selected from a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C2 to C60 heteroaryl group,

L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted C6 to C60 arylene group or a substituted or unsubstituted C2 to C60 heteroarylene group,

m is an integer of 0 to 3, when m is 0, L1 is a direct bond, when m is 2 or 3, each L1 is the same as or different from each other, and each is independently selected;

n is an integer from 0 to 3, when n is 0, L2 is a direct bond, when n is 2 or 3, each L2 is the same as or different from each other, and each is independently selected;

o is a natural number from 1 to 3, and when o is 2 or 3, each R15 is the same as or different from each other, and each is independently selected;

p is an integer of 0 to 4, and when p is 2 to 4, R5 are the same as or different from each other, and are each independently selected;

q is an integer from 0 to 3, and when q is 2 or 3, R6 are the same as or different from each other, and are each independently selected;

However, -(L1)m-(L2)n-(R15)o is not a phenyl or biphenyl group.

In addition, the present invention,

a first electrode;

a second electrode provided to face the first electrode; and

An organic light-emitting device comprising a; at least one organic material layer provided between the first electrode and the second electrode,

At least one layer of the organic material layer provides an organic light emitting device including the heterocyclic compound represented by Formula 1 above.

In addition, the present invention provides an organic light emitting device in which at least one layer of the organic material layer further comprises a heterocyclic compound represented by the following formula (2).

[Formula 2]

In Formula 2,

X is N, O or S;

R27 and R28 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group,

R29 and R30 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; -SiR201R202R203, -P(=O)R201R202; and 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 selected from the group consisting of an amine group unsubstituted or substituted with each other, Two or more adjacent groups combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 hetero ring,

R201, R202, and R203 are the same as or different from each other, and each independently represents hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted a C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group,

f and g are the same as or different from each other, and are each independently an integer of 0 to 7.

In addition, the present invention,

It provides 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 2 above.

In addition, 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 of the organic light emitting device. A manufacturing method is provided.

The heterocyclic compound of the present invention may be used as an organic material layer of an organic light emitting device. The heterocyclic compound may serve as a hole injection layer material, a hole transport layer material, a light emitting layer material, an electron transport layer material, an electron injection layer material, etc. in the 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 heterocyclic compound may be used alone as a light emitting material, may be used as a host material or a dopant material of the light emitting layer. When the heterocyclic compound of the present invention is used in the organic material layer, it is possible to lower the driving voltage of the organic light emitting device, improve luminous efficiency, and improve lifespan characteristics.

1 to 3 are views schematically showing a stacked structure of an organic light emitting device according to an embodiment of the present invention, respectively.

Hereinafter, the present invention will be described in detail.

In the present invention, 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, the position where the substituent is substitutable, is not limited. , When two or more substituents are substituted, two or more substituents may be the same as or different from each other.

In the present invention, "substituted or unsubstituted" means C1 to C60 straight or branched chain alkyl; C2 to C60 linear or branched alkenyl; C2 to C60 linear 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 that it is substituted or unsubstituted with one or more substituents, or substituted or unsubstituted with a substituent to which two or more substituents selected from the above-exemplified substituents are connected.

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

In the present invention, 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 invention, 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, stilbenyl group, styrenyl group, etc., but are not limited thereto.

In the present invention, 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 invention, 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, benzyloxy, p-methylbenzyloxy, etc. may be It is not limited.

In the present invention, 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 invention, 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 invention, 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 directly connected or condensed with an aryl group or another ring group. Here, the other ring group may be an aryl group, but may be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, and 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 triphenyl 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 invention, the phosphine oxide group is represented by -P(=O)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; 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, a dinaphthylphosphine oxide group, and the like, but is not limited thereto.

In the present invention, the silyl group is a substituent containing Si and the Si atoms are directly connected as a radical, and is represented by -SiR ₁₀₄ R ₁₀₅ R ₁₀₆ , R ₁₀₄ to R ₁₀₆ are the same or different from each other, and each independently hydrogen; heavy hydrogen; halogen; 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, etc. It is not limited.

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

,

,

,

,

,

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

,

,

,

,

,

and the like, but is not limited thereto.

In the present invention, 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 invention, 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 invention, 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.

In the present invention, "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.

In the present invention, "when a substituent is not indicated 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 one embodiment of the present invention, "when a substituent is not indicated in the chemical formula or compound structure" may mean that all positions that can come as a substituent are hydrogen or deuterium. That is, in the case of deuterium, deuterium is an isotope of hydrogen, and some hydrogen atoms may be isotope deuterium, and the content of deuterium may be 0% to 100%.

In one embodiment of the present invention, in "when a substituent is not indicated in the chemical formula or compound structure", "the content of deuterium is 0%", "the content of hydrogen is 100%", "the substituents are all hydrogen", etc. If deuterium is not explicitly excluded, hydrogen and deuterium may be used in combination in the compound.

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

In one embodiment of the present invention, isotopes have the same atomic number (Z), but isotopes meaning atoms having different mass numbers (A) have the same number of protons, but neutrons It can also be interpreted as an element with a different number of (neutron).

In one embodiment of the present invention, the meaning of the content of specific substituents T% is T2 when the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents is defined as T2. It can be defined as /T1×100 = 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 함량 20%라는 것인 하기 구조식으로 표시될 수 있다.That is, in one example,

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

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

In the present invention, the content of deuterium in the heterocyclic compound represented by Formula 1 may be 0 to 100%, more preferably 30 to 100%.

In the present invention, the C6 to C60 aromatic hydrocarbon ring means a compound including an aromatic ring consisting of C6 to C60 carbons and hydrogen, for example, benzene, biphenyl, triphenyl, triphenylene, naphthalene, Anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, etc., but are not limited thereto, and aromatic hydrocarbon ring compounds known in the art as satisfying the above carbon number include all

The present invention provides a heterocyclic compound represented by the following formula (1).

[Formula 1]

In Formula 1,

X is O or S;

R1 to R14 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)R101R202; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other combine with each other 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 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,

R15 is a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or -Si(Ar1) ₃ , wherein each Ar1 included in (Ar1) ₃ is the same as each other. or different, each independently selected from a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C2 to C60 heteroaryl group,

L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted C6 to C60 arylene group or a substituted or unsubstituted C2 to C60 heteroarylene group,

m is an integer of 0 to 3, when m is 0, L1 is a direct bond, when m is 2 or 3, each L1 is the same as or different from each other, and each is independently selected;

n is an integer from 0 to 3, when n is 0, L2 is a direct bond, when n is 2 or 3, each L2 is the same as or different from each other, and each is independently selected;

o is a natural number from 1 to 3, and when o is 2 or 3, each R15 is the same as or different from each other, and each is independently selected;

p is an integer of 0 to 4, and when p is 2 to 4, R5 are the same as or different from each other, and are each independently selected;

q is an integer from 0 to 3, and when q is 2 or 3, R6 are the same as or different from each other, and are each independently selected;

However, -(L1)m-(L2)n-(R15)o is not a phenyl or biphenyl group.

In the compound of Formula 1, when L1 is a direct bond, L2 is a phenylene group, R15 is a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group, and n and o are 1; R15 may be more preferably bonded to the ortho or meta position of the phenylene group.

In the above, even when n is not 1, R15 may be bonded to the ortho or meta position of the phenylene group.

The heterocyclic compound represented by Formula 1 facilitates intramolecular charge transfer, and reduces the energy gap between the singlet energy level (S ₁ ) and the triplet energy level (T ₁ ), thereby exciton (exciton) ) can be well preserved.

In one embodiment of the present invention, in the substituent including the hetero atom, the hetero atom may be one or more selected from O, S, Se, N, or Si.

In another embodiment of the present invention, in the substituent including the hetero atom, the hetero atom may be one or more selected from O, S, or N.

In another embodiment of the present invention, in the substituent including the hetero atom, the hetero atom may be O.

In another embodiment of the present invention, in the substituent including the hetero atom, the hetero atom may be S.

In another embodiment of the present invention, in the substituent including the hetero atom, the hetero atom may be N.

In one embodiment of the present invention, X may be O.

In one embodiment of the present invention, X may be S.

In one embodiment of the present invention, R1 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C2 to C10 alkenyl group; a substituted or unsubstituted C2 to C10 alkynyl group; a substituted or unsubstituted C1 to C10 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 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, or two or more groups adjacent to each other 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 C10 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, R1 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C2 to C10 alkenyl group; a substituted or unsubstituted C2 to C10 alkynyl 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, R1 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C5 alkyl group; a substituted or unsubstituted C2 to C5 alkenyl group; a substituted or unsubstituted C2 to C5 alkynyl group; 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, R1 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C5 alkyl group; 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, R1 to R14 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, substituted or unsubstituted phenyl, naphthalenyl, pyridinyl , anthracenyl, carbazole, dibenzothiophene, dibenzofuran, or phenanthrenyl group.

In another embodiment of the present invention, R1 to R14 may be the same as or different from each other, and each independently hydrogen, deuterium, and a substituted or unsubstituted C1 to C5 alkyl group. In the above, the C1 to C5 alkyl group may be methyl, ethyl, a straight or branched propyl group, a straight or branched butyl group, or a straight or branched pentyl group.

In another embodiment of the present invention, R1 to R14 may be the same as or different from each other, and each independently hydrogen or deuterium.

In another embodiment of the present invention, the 'substitution' of R1 to R14 is C1 to C10 alkyl; C2 to C10 alkenyl; C2 to C10 alkynyl; C3 to C15 cycloalkyl; C2 to C20 heterocycloalkyl; C6 to C30 aryl; C2 to C30 heteroaryl; C1 to C10 alkylamine; C6 to C30 arylamine; and one or more substituents selected from the group consisting of a C2 to C30 heteroarylamine group.

In another embodiment of the present invention, the 'substitution' of R1 to R14 is C1 to C10 alkyl; C6 to C30 aryl; One or more substituents selected from the group consisting of a C2 to C30 heteroaryl group may be each independently formed.

In another embodiment of the present invention, the 'substitution' of R1 to R14 is C1 to C5 alkyl; C6 to C20 aryl; and one or more substituents selected from the group consisting of a C2 to C20 heteroaryl group.

In another embodiment of the present invention, the 'substitution' of R1 to R14 is methyl, ethyl, straight-chain or branched propyl, straight-chain or branched butyl, straight-chain or branched pentyl, phenyl, naphthalenyl, pyri Each of at least one substituent selected from the group consisting of dinyl, anthracenyl, carbazole, dibenzothiophene, dibenzofuran, and phenanthrenyl group may be independently formed.

In another embodiment of the present invention, the 'substitution' of R1 to R14 may be each independently made of methyl, ethyl, a straight or branched chain propyl group, a straight or branched chain butyl group, and a straight or branched chain pentyl group. .

In one embodiment of the present invention, R15 may be a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or —Si(Ar1) ₃ , wherein (Ar1 ) each Ar1 included in ₃ is the same as or different from each other, and each may be independently selected from a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C2 to C30 heteroaryl group.

In another embodiment of the present invention, R15 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or —Si(Ar1) ₃ , wherein (Ar1) ₃ Each Ar1 included in is the same as or different from each other, and each may be independently selected from a substituted or unsubstituted C6 to C20 aryl group and a substituted or unsubstituted C2 to C20 heteroaryl group.

In another embodiment of the present invention, R15 is substituted or unsubstituted phenyl, naphthalenyl, pyridinyl, anthracenyl, carbazole, dibenzothiophene, dibenzofuran, fluorenyl, 9,9'-dimethyl fluorenyl, 9,9'-dibenzofluorenyl, 9,9'-spirobifluorenyl, phenanthrenyl, or -Si(Ar1) ₃ , wherein each Ar1 included in (Ar1) ₃ are the same as or different from each other, and each may be independently selected from substituted or unsubstituted phenyl, naphthalenyl, pyridinyl, anthracenyl, and phenanthrenyl.

In another embodiment of the present invention, R15 is substituted or unsubstituted phenyl, dibenzothiophene, dibenzofuran, fluorenyl, 9,9'-dimethylfluorenyl, 9,9'-dibenzofluorene nyl, 9,9'-spirobifluorenyl, or -Si(Ar1) ₃ , wherein each Ar1 included in (Ar1) ₃ may be a phenyl group.

In another embodiment of the present invention, the 'substitution' of R15 is C1 to C10 alkyl; C2 to C10 alkenyl; C2 to C10 alkynyl; C3 to C15 cycloalkyl; C2 to C20 heterocycloalkyl; C6 to C30 aryl; C2 to C30 heteroaryl; C1 to C10 alkylamine; C6 to C30 arylamine; and one or more substituents selected from the group consisting of a C2 to C30 heteroarylamine group.

In another embodiment of the present invention, the 'substitution' of R15 is C1 to C10 alkyl; C6 to C30 aryl; and one or more substituents selected from the group consisting of a C2 to C30 heteroaryl group.

In another embodiment of the present invention, the 'substitution' of R15 is C1 to C5 alkyl; C6 to C20 aryl; C2 to C20 may be each independently composed of one or more substituents selected from the group consisting of heteroaryl.

In another embodiment of the present invention, the 'substitution' of R15 is methyl, ethyl, straight or branched propyl, straight or branched butyl, straight or branched pentyl, phenyl, naphthalenyl, pyridinyl, One or more substituents selected from the group consisting of anthracenyl, carbazole, dibenzothiophene, dibenzofuran, and phenanthrenyl may be each independently formed.

In another embodiment of the present invention, the 'substitution' of R15 is at least one substituent selected from the group consisting of methyl, ethyl, straight or branched propyl, straight or branched butyl, and straight or branched pentyl. each can be done independently.

In one embodiment of the present invention, L1 and L2 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group can

In another embodiment of the present invention, L1 and L2 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted C6 to C20 arylene group or a substituted or unsubstituted C2 to C20 heteroarylene group can

In another embodiment of the present invention, L1 and L2 are the same as or different from each other, and each independently a direct bond, substituted or unsubstituted phenylene, naphthalene, pyridine, anthracene, carbazole, dibenzothiophene, dibenzofuran It may be selected from the group consisting of , phenanthrene, or pyrenyl.

In another embodiment of the present invention, L1 and L2 are the same as or different from each other, and each may be independently selected from the group consisting of a direct bond, substituted or unsubstituted phenylene, naphthalene, and pyridine.

In another embodiment of the present invention, L1 and L2 may be the same as or different from each other, and each independently may be a direct bond or a substituted or unsubstituted phenylene.

In another embodiment of the present invention, the 'substitution' of L1 and L2 is C1 to C10 alkyl; C2 to C10 alkenyl; C2 to C10 alkynyl; C6 to C30 aryl; and one or more substituents selected from the group consisting of C2 to C30 heteroaryl.

In another embodiment of the present invention, the 'substitution' of L1 and L2 is C1 to C5 alkyl; C6 to C20 aryl; and one or more substituents selected from the group consisting of a C2 to C20 heteroaryl group.

In another embodiment of the present invention, the 'substitution' of L1 and L2 is C1 to C5 alkyl; C6 to C12 aryl; and one or more substituents selected from the group consisting of C2 to C12 heteroaryl.

In another embodiment of the present invention, the 'substitution' of L1 and L2 is methyl, ethyl, straight or branched chain propyl, straight or branched chain butyl, straight or branched chain pentyl, phenyl, and naphthalenyl Each may be independently formed by one or more substituents selected from the group consisting of.

In another embodiment of the present invention, the 'substitution' of L1 and L2 is selected from the group consisting of methyl, ethyl, straight or branched chain propyl, straight or branched chain butyl, and straight or branched chain pentyl. Each may be independently formed by one or more substituents.

In one embodiment of the present invention,

The compound represented by Chemical Formula 1 may be a compound represented by the following Chemical Formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

The definitions of X, R1 to R14, m, p, and q are the same as in Formula 1 above,

Y is C, O, or S;

R16 to R26 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; And a substituted or unsubstituted C2 to C60 heteroaryl group; selected from the group consisting of, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to to form a C60 heterocyclic ring,

r and s are the same as or different from each other and are each independently an integer of 0 to 4,

t, v, and b are the same as or different from each other and are each independently an integer from 0 to 4,

u, w, c, d, and e are the same as or different from each other and are each independently an integer from 0 to 5;

a is a natural number from 1 to 3,

When each of R16, R22, and R23 to R26 is two or more, they are the same as or different from each other, and are each independently selected;

At least one of m, r and s is non-zero.

In Formula 1-2, when m is 1, it is more preferable that the substituted or unsubstituted dibenzofuranyl group or the substituted or unsubstituted dibenzothiophenyl group bonded to the phenylene group is bonded to the ortho or meta position of the phenylene group. can do.

In the above, even when m is 2 or 3, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group bonded to the phenylene group may be bonded to the ortho or meta position of the phenylene group.

In one embodiment of the present invention, Y may be C.

In one embodiment of the present invention, Y may be O.

In one embodiment of the present invention, Y may be S.

In one embodiment of the present invention, R6 to R26 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C2 to C10 alkenyl group; a substituted or unsubstituted C2 to C10 alkynyl group; a substituted or unsubstituted C1 to C10 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; and a substituted or unsubstituted C2 to C30 heteroaryl group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 group It can form a hetero ring.

In another embodiment of the present invention, R16 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C2 to C10 alkenyl group; a substituted or unsubstituted C2 to C10 alkynyl group; a substituted or unsubstituted C6 to C30 aryl group; A substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 hetero ring selected from the group consisting of a substituted or unsubstituted C2 to C30 heteroaryl group, or two or more adjacent groups are bonded to each other rings can be formed.

In another embodiment of the present invention, R16 to R26 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C5 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; It may be selected from the group consisting of a substituted or unsubstituted C2 to C20 heteroaryl group.

In another embodiment of the present invention, R16 to R26 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, substituted or unsubstituted phenyl, naphthalenyl, pyridinyl , anthracenyl, carbazole, dibenzothiophene, dibenzofuran, and phenanthrenyl, or two or more groups adjacent to each other may combine with each other to form a substituted or unsubstituted fluorenyl group.

In another embodiment of the present invention, R16 to R19 and R22 to R26 may be the same as or different from each other, and each independently hydrogen, deuterium, or a substituted or unsubstituted C1 to C5 alkyl group.

In another embodiment of the present invention, R16 to R19 and R22 to R26 may be the same as or different from each other, and each independently hydrogen or deuterium.

In another embodiment of the present invention, R21 and R22 are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C5 alkyl group or a substituted or unsubstituted phenyl group, or a substituted or unsubstituted flu It can form an orenyl group.

In another embodiment of the present invention, the 'substitution' of R16 to R26 is C1 to C10 alkyl; C2 to C10 alkenyl; C2 to C10 alkynyl; C3 to C15 cycloalkyl; C2 to C20 heterocycloalkyl; C6 to C30 aryl; and one or more substituents selected from the group consisting of C6 to C30 heteroaryl, each independently.

In another embodiment of the present invention, the 'substitution' of R16 to R26 is C1 to C10 alkyl; C6 to C20 aryl; C2 to C20 may be each independently composed of one or more substituents selected from the group consisting of heteroaryl.

In another embodiment of the present invention, the 'substitution' of R16 to R26 is C1 to C5 alkyl, phenyl, naphthalenyl, pyridinyl, anthracenyl, carbazole, dibenzothiophene, dibenzofuran, and phenane One or more substituents selected from the group consisting of threnyl may be each independently formed.

In another embodiment of the present invention, the 'substitution' of R16 to R26 is at least one selected from the group consisting of methyl, ethyl, straight or branched propyl, straight or branched butyl, and straight or branched pentyl groups. Each of the substituents may be independently formed.

In one embodiment of the present invention, the R16 to R19 and R22 to R26 are the same as or different from each other, and each independently represent hydrogen, deuterium, a C1 to C5 alkyl group,

R21 and R22 may be the same as or different from each other and each independently represent a C1 to C5 alkyl or substituted or unsubstituted phenyl group, or it may be more preferable to combine with each other to form a substituted or unsubstituted fluorenyl group.

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

The compound of Formula 1 may synthesize a compound having the intrinsic properties of the introduced substituent by introducing various substituents into the corresponding structure. For example, by introducing 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 electron injection layer material used in manufacturing the organic light emitting device into the core structure, 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.

The heterocyclic compound is a hole injection layer material, a hole transport layer material, an electron blocking layer material, a light emitting layer material, a hole blocking layer material, an electron transport layer material and an electron injection layer material used in the organic material layer of the organic light emitting device at least one use selected from can be used, and in particular, it can be preferably used as a light emitting layer material.

In addition, the present invention,

a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises a heterocyclic compound represented by Formula 1 above. will be.

In one embodiment of the present invention, the organic material layer includes at least one layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, the at least one layer may include a heterocyclic compound represented by Formula 1 above.

In one 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 the electron transport layer may include a heterocyclic compound represented by Formula 1 above.

In another embodiment, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include a heterocyclic compound represented by Formula 1 above.

In another embodiment, the organic layer includes 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 a heterocyclic compound represented by Formula 1 above.

In another embodiment, the organic material layer may include an emission layer, and the emission layer may include a heterocyclic compound represented by Formula 1 above.

In addition, the light emitting layer includes a host material, and the heterocyclic compound represented by Formula 1 may be used as the host material.

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 green organic light emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material of the green 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 Formula 1 may be used as a material of the blue 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 Formula 1 may be used as a material of the red 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 Formula 1 may be used as a light emitting layer material of the green 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 Formula 1 may be used as a light emitting layer material of the blue 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 Formula 1 may be used as a material for the emission layer 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 invention 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 invention 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 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 according to an embodiment of the present invention, the organic material layer including the heterocyclic compound represented by Formula 1 may further include a heterocyclic compound represented by Formula 2 below.

[Formula 2]

In Formula 2,

X is N, O or S;

R27 and R28 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group,

R29 and R30 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; -SiR201R202R203, -P(=O)R201R202; and 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 selected from the group consisting of an amine group substituted or unsubstituted, or each other Two or more adjacent groups combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 hetero ring,

R201, R202, and R203 are the same as or different from each other, and each independently represents hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted a C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group,

f and g are the same as or different from each other, and are each independently an integer of 0 to 7.

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. That is, when both compounds are included at the same time, an exciplex phenomenon may occur, thereby further increasing the efficiency.

The exciplex phenomenon is a phenomenon in which energy having the size of the HOMO energy level of the donor (p-host) and the LUMO energy level of the acceptor (n-host) is emitted through electron exchange between two molecules. When an exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) occurs, and thus the internal quantum efficiency of fluorescence can be increased to 100%. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as hosts of the emission layer, holes are injected into the p-host and electrons are transferred to the n-host Since it is injected into That is, when the compound (P-type) represented by the formula (2) is used as the donor and the compound (N-type) represented by the formula (1) is used as the acceptor, an excellent device indicates characteristics.

In the organic light emitting diode according to an embodiment of the present invention, R29 and R30 may be hydrogen.

In the organic light-emitting device according to an embodiment of the present invention, R27 and R28 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In the organic light-emitting device according to another embodiment, R27 and R28 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In the organic light emitting device according to another embodiment, R27 and R28 are the same as or different from each other, and each independently selected from the group consisting of a C1 to C40 alkyl group, a C6 to C40 aryl group, a cyano group, and -SiR201R202R203 a C6 to C40 aryl group unsubstituted or substituted with one or more substituents; Alternatively, it may be a C2 to C40 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a C6 to C40 aryl group and a C2 to C40 heteroaryl group.

In the organic light emitting device according to another embodiment, R27 and R28 are the same as or different from each other, and each independently selected from the group consisting of a C1 to C40 alkyl group, a C6 to C40 aryl group, a cyano group, and -SiR201R202R203 It may be a C6 to C40 aryl group unsubstituted or substituted with one or more substituents.

In the organic light-emitting device according to another embodiment, R27 and R28 are the same as or different from each other, and each independently a phenyl group, a cyano group, or a phenyl group unsubstituted or substituted with -SiR201R202R203; a biphenyl group unsubstituted or substituted with a phenyl group; naphthyl group; a fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; spirobifluorenyl group; Or it may be a triphenylenyl group.

In the organic light emitting diode according to an embodiment of the present invention, 201, R202, and R203 may be a phenyl group.

In the organic light-emitting device according to an embodiment of the present invention, the compound represented by Formula 2 may be a heterocyclic compound represented by Formula 2-1 below.

[Formula 2-1]

In Formula 2-1,

R31 and R32 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C60 aryl group and a substituted or unsubstituted C2 to C60 heteroaryl group,

h is an integer from 0 to 4, i is an integer from 0 to 2,

L3 is a direct bond, a substituted or unsubstituted C1 to C60 arylene group, or a substituted or unsubstituted C2 to C60 heteroarylene group,

Ar2 and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted C1 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group,

The definitions of R29 and R30, f and g are the same as those in Formula 2 above.

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

In one embodiment of the present invention, the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer is a heterocyclic compound represented by the formula (1) and a heterocyclic compound represented by the formula (2) may include

In another embodiment, the organic material layer includes an electron blocking layer or a hole blocking layer, the electron blocking layer or the hole blocking layer is a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2 may include

In another embodiment, the organic material layer comprises an electron transport layer, a light emitting layer or a hole blocking layer, wherein the electron transport layer, the light emitting layer or the hole blocking layer is a heterocyclic compound represented by Formula 1 and a heterocyclic ring represented by Formula 2 compounds may be included.

In another embodiment, the organic material layer may include a light emitting layer, and the light emitting layer may include a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2 above.

In addition, the light emitting layer may include a host material, and the host material may include a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2 above.

Also, the present invention

It relates to 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 2 above.

In one embodiment of the present invention, the composition for the organic material layer may be used as an electron injection layer or an electron transport layer material.

In another embodiment, the composition for the organic material layer may be used as an electron blocking layer or a hole blocking layer material.

In another embodiment, the composition for the organic material layer may be used as an electron transport layer, a light emitting layer or a hole blocking layer material.

In another embodiment, the composition for an organic material layer may be used as a light emitting layer material.

In addition, the light emitting layer includes a host, and the composition for an organic material layer may be used as a host material.

Specific 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 Formula 1 and the heterocyclic compound represented by Formula 2 in the composition for an organic material layer of the organic light emitting device may be 1:10 to 10:1, and , 1: 8 to 8: 1, may be 1: 5 to 5: 1, may be 1: 2 to 2: 1, but is not limited thereto.

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

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

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", L2MX' and L3M may be used, but the scope of the present invention is not limited by these examples.

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

The L is an anionic bidentate ligand coordinated to the 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), (thiophenepyrizine), phenylpyridine, benzothiophenepyrizine, 3-methoxy-2-phenylpyridine, thiophenepyrizine, 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 thereto.

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

In one embodiment of the present invention, Ir(ppy) ₃ may be used as the green 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% to 15%, preferably 3% to 10%, more preferably 5% to 10% based on the entire emission 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 embodiment of the present invention. 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.

In addition, 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

A method of manufacturing an organic light emitting device comprising the step of forming a second electrode on the organic material layer, wherein the forming of the organic material layer uses the composition for an organic material layer according to an embodiment of the present invention to form one or more organic material layers It relates to a method of manufacturing an organic light emitting device comprising the steps.

In one embodiment of the present invention, the step of forming the organic material layer is a pre-mixed (pre-mixed) heterocyclic compound represented by the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 included in the composition for an organic layer. Forming a composition for an organic material layer, and applying it by a vacuum deposition method or a solution coating method may be to form an organic material layer.

The pre-mixed (pre-mixed), the heterocyclic compound represented by the formula (1) and the heterocyclic compound represented by the formula (2) are first mixed with the materials before deposition on the organic material layer means to put in one source and mix.

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

The organic material layer including the heterocyclic compound represented by Chemical Formula 1 and Chemical Formula 2 at the same time may further include another material if necessary.

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 Formula 2 are exemplified below, but these are for illustration only and to limit the scope of the present application is not, and may be substituted with materials known in the art.

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 layer material, a known hole injection layer material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in US Pat. No. 4,356,429 or Advanced Material, 6, p.677 (1994). Starburst-type amine derivatives described, 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), soluble conductive polymer 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-styrene-sulfonate) (Polyaniline/Poly(4-styrene-sulfonate)) and the like may be used.

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

Examples of the electron transport layer material include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanogianthraquinodimethane and its derivatives, and fluorenone. Derivatives, diphenyldicyano group ethylene 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 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 the light emitting layer 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 layer material, it can also be used as a phosphorescent material. As the material of the light emitting layer, a material that emits light by combining holes and electrons respectively injected from the anode and the cathode may be used alone, but materials in which the host material and the dopant material together participate in light emission may be used.

When a host of the light emitting layer material is mixed and used, a host of the same type may be mixed and used, or a host of a different type 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.

The organic light emitting diode according to an embodiment of the present invention 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 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 examples are presented to help the understanding of the present invention, but the following examples are provided for easier understanding of the present invention, and the present invention is not limited thereto.

<Preparation Example 1> Preparation of compound 1-5

1) Preparation of compound 1-5-1

2,4-dichloro-6-(dibenzo[b,d]furan-1-yl)-1,3,5-triazine (2,4-dichloro-6-(dibenzo[b,d]furan-1 -yl)-1,3,5-triazine) 18.1 g (57.1 mM), [1,1':3',1''-terphenyl]-3-yl boronic acid ([1,1':3',1''-terphenyl]-3-ylboronic acid) 14.2 g (51.9 mM), Pd(PPh3) 4 3.0 g (2.6 mM) and K2CO3 14.5 g (105.0 mM) 1,4-dioxane (1,4) -dioxane)/H2O was dissolved in 400mL/80mL and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hexane=1:3) and recrystallized from methanol to obtain 21.2 g (80%) of the target compound 1-5-1.

2) Preparation of compound 1-5

Compound 1-5-1 19.1 g (37.4 mM), triphenylen-2-yl-boronic acid 11.2 g (41.1 mM), Pd (PPh ₃ ) 4 2.2 g (1.9 mM), K ₂ CO ₃ 10.3 g (74.8 mM) was dissolved in 1,4-dioxane (1,4-dioxane)/H ₂ O 400 mL/80 mL and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:2) and recrystallized from methanol to obtain the target compound 1-5, 22.3 g (85%).

In Preparation Example 1, 2,4-dichloro-6- (dibenzo [b, d] furan-1-yl) -1,3,5-triazine (2,4-dichloro-6- (dibenzo [b, d]furan-1-yl)-1,3,5-triazine) using Intermediate A of Table 1 below and [1,1':3',1''-terphenyl]-3-yl boronic acid ( [1,1':3',1''-terphenyl]-3-ylboronic acid) was prepared in the same manner as in Preparation Example 1, except that Intermediate B of Table 1 was used, and the target compound was synthesized.

compound
number Intermediate A Intermediate B target compound 1-1

1-6

1-8

1-40

1-43

1-45

1-46

1-47

1-53

1-64

1-67

1-69

1-70

1-71

1-74

1-75

1-79

1-95

1-103

1-114

1-167

1-205

1-282

2-1

2-5

2-8

2-77

<Preparation Example 2> Synthesis of compound 3-2

1) Preparation of compound 3-2-2

2-bromodibenzo [b, d] thiophene (2-bromodibenzo [b, d] thiophene) 4.2 g (15.8 mM), 9-phenyl-9H, 9'H-3,3'-bicarbazole (9 -phenyl-9H,9'H-3,3'-bicarbazole) 6.5g (15.8mM), CuI 3.0g (15.8mM), trans-1,2-diaminocyclohexane (trans-1,2-diaminocyclohexane) 1.9 mL (15.8 mM), 3.3 g (31.6 mM) of K ₃ PO ₄ were dissolved in 100 mL of 1,4-dioxane and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain the target compound 3-2-2, 7.9 g (85%).

2) Preparation of compound 3-2-1

A mixed solution of compound 3-2-2, 8.4 g (14.3 mmol) and 100 mL of tetrahydrofuran (THF) was added at -78 ° C. to 7.4 mL (18.6 mmol) of 2.5M n-butyllithium (n-BuLi). It was added dropwise and stirred at room temperature for 1 hour. 4.8 mL (42.9 mmol) of trimethyl borate was added dropwise to the reaction mixture, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:methanol (MeOH)=100:3) and recrystallized from DCM to obtain the target compound 3-2-1, 3.9g (70%).

3) Preparation of compound 3-2

Compound 2-2-1, 6.7g (10.5mM), iodobenzene (iodobenzene) 2.1g (10.5mM), Pd(PPh ₃ ) ₄ 606mg (0.52mM), K ₂ CO ₃ 2.9g (21.0mM) It was dissolved in toluene/ethanol (EtOH)/H ₂ O 100/20/20 mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain 4.9 g (70%) of the target compound 3-2.

<Preparation Example 2-1> Synthesis of compound 3-3

The target compound was prepared in the same manner as in Compound 2-2, except that 4-iodo-1,1'-biphenyl was used instead of iodobenzene in Preparation Example 2 3-3 (83%) was obtained.

<Preparation Example 2-2> Synthesis of compound 3-12

Target Compound 3 was prepared in the same manner as in Compound 2-2, except that 4-iododibenzo[b,d]furan was used instead of iodobenzene in Preparation Example 2 -12 (80%) was obtained.

<Preparation Example 3> Synthesis of compound 4-3

1) Preparation of compound 4-3

3-bromo-1,1'-biphenyl (3-bromo-1,1'-biphenyl) 3.7g (15.8mM), 9-phenyl-9H,9'H-3,3'-bicarbazole ( 9-phenyl-9H,9'H-3,3'-bicarbazole) 6.5 g (15.8 mM), CuI 3.0 g (15.8 mM), trans-1,2-diaminocyclohexane ) 1.9 mL (15.8 mM), 3.3 g (31.6 mM) of K ₃ PO ₄ were dissolved in 100 mL of 1,4-oxane and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain 7.5 g (85%) of the target compound 4-3.

In Preparation Example 3, the intermediate A of Table 2 was used instead of 3-bromo-1,1`-biphenyl and the intermediate of Table 2 instead of 9-phenyl-9H,9'H-3,3'-bicarbazole A target compound was synthesized in the same manner as in Preparation Example 3 except that B was used.

compound
number Intermediate A Intermediate B target compound 4-4

4-7

4-9

4-31

4-32

4-42

The remaining compounds other than the compounds described in Preparation Examples 1 to 3 and Tables 1 to 2 were prepared in the same manner as in the above-described Preparation Examples, and the synthesis confirmation results are shown in Tables 3 and 4 below.

compound
number ¹ H NMR (CDCL3, 200 Mz) 1-1 δ = 9.60 (1H, d), 9.27 (1H, s), 8.33-8.30 (2H, m), 8.15 (1H, d), 7.98-7.96 (5H, m), 7.79-7.31 (21H, m) 1-5 δ = 9.60 (1H, d), 9.27 (1H, s), 8.38-8.30 (3H, m), 8.15 (1H, d), 7.98-7.94 (3H, m), 7.82-7.31 (22H, m) 1-6 δ = 9.60 (1H, d), 9.27 (1H, s), 8.38-8.30 (3H, m), 8.15 (1H, d), 7.98-7.94 (2H, m), 7.82-7.25 (23H, m) 1-8 δ = 9.60 (1H, d), 9.27 (1H, s), 8.33-8.30 (2H, m), 8.15 (1H, d), 7.98-7.96 (3H, m), 7.82-7.25 (23H, m) 1-40 δ = 9.60 (1H, d), 9.27 (1H, s), 8.33-8.30 (2H, m), 8.15 (1H, d), 7.98-7.96 (3H, m), 7.82-7.25 (27H, m) 1-43 δ = 9.60 (1H, d), 9.27 (1H, s), 8.33-8.30 (2H, m), 8.15 (1H, d), 7.98-7.96 (3H, m), 7.82-7.25 (31H, m) 1-45 δ = 9.60 (1H, d), 9.27 (1H, s), 8.55 (1H, d), 8.45 (1H, d), 8.33-8.30 (2H, m), 8.15 (1H, d), 7.98-7.92 ( 3H, m), 7.82 (1H, d), 7.70-7.31 (14H, m) 1-46 δ = 9.60 (1H, d), 9.27 (1H, s), 8.33-8.30 (2H, m), 8.15 (1H, d), 8.03-7.98 (3H, m), 7.82-7.52 (13H, m), 7.39-7.31 (4H, m) 1-47 δ = 9.60 (1H, d), 9.27 (1H, s), 8.45 (1H, d), 8.33-8.15 (5H, m), 7.98-7.93 (3H, m), 7.82 (1H, d), 7.70- 7.31 (13H, m) 1-53 δ = 9.60 (1H, d), 9.27 (1H, s), 8.33-8.30 (2H, m), 8.15 (1H, d), 7.98 (2H, d), 7.82 (2H, m), 7.79-7.52 ( 12H, m), 7.39-7.31 (4H, m) 1-64 δ = 9.60 (1H, d), 9.27 (1H, s), 8.55 (1H, d), 8.45 (1H, d), 8.33-8.30 (3H, m), 8.15 (1H, d), 7.98-7.96 ( 3H, m), 7.82 (1H, d), 7.70-7.25 (16H, m) 1-67 δ = 9.60 (1H, d), 9.27 (1H, s), 8.55 (1H, d), 8.45-8.30 (5H, m), 8.15 (1H, d), 7.98-7.93 (3H, m), 7.82 7.31 (17H, m) 1-69 δ = 9.60 (1H, d), 9.27 (1H, s), 8.38-8.15 (8H, m), 7.98-7.93 (3H, m), 7.82-7.31 (14H, m) 1-70 δ = 9.60 (1H, d), 9.27 (1H, s), 8.38-8.30 (3H, m), 8.15 (1H, d), 7.94-7.52 (19H, m), 7.39-7.31 (4H, m) 1-71 δ = 9.60 (1H, d), 9.27 (1H, s), 8.45-8.30 (4H, m), 8.15-8.12 (3H, m), 7.99-7.93 (4H, m), 7.82-7.31 (16H, m) ) 1-74 δ = 9.60 (1H, d), 9.27 (1H, s), 8.38-8.30 (3H, m), 8.15-8.09 (2H, m), 7.98-7.52 (18H, m), 7.39-7.28 (4H, m) ), 1.69 (6H, s) 1-75 δ= 9.60 (1H, d), 9.27 (1H, s), 8.38-8.30 (3H, m), 8.15-8.09 (2H, m), 7.98-7.52 (18H, m), 7.39-7.18 (14H, m) ) 1-79 δ = 9.60 (1H, d), 9.27 (1H, s), 8.38-8.30 (3H, m), 8.15 (1H, d), 7.98-7.82 (6H, m), 7.73-7.31 (25H, m) 1-95 δ = 9.60 (1H, d), 9.27 (1H, s), 8.55 (1H, d), 8.45-8.30 (5H, m), 8.15 (1H, d), 7.98-7.93 (4H, m), 7.82 7.31 (20H, m) 1-103 δ = 9.60 (1H, d), 9.27 (1H, s), 8.38-8.30 (3H, m), 8.15 (1H, d), 7.98-7.90 (4H, m), 7.82-7.31 (23H, m), 1.69 (6H, s) 1-114 δ = 9.60 (1H, d), 9.27 (1H, s), 8.38-8.30 (3H, m), 8.15 (1H, d), 7.98-7.31 (25H, m) 1-167 δ = 9.60 (1H, d), 9.27 (1H, s), 8.33-8.30 (2H, m), 8.15 (1H, d), 8.03-7.96 (4H, m), 7.82-7.64 (8H, m), 7.54-7.25 (14H, m) 1-205 δ = 9.60 (1H, d), 9.27 (1H, s), 8.33-8.30 (2H, m), 8.15 (1H, d), 8.03-7.98 (4H, m), 7.82-7.52 (12H, m), 7.39-7.31 (4H, m) 1-282 δ = 9.60 (1H, d), 9.27 (1H, s), 8.33-8.30 (2H, m), 8.15-8.08 (3H, m), 7.98 (2H, d), 7.88 (2H, d), 7.70- 7.51 (10H, m), 7.39-7.31 (4H, m) 2-1 δ = 9.60 (1H, d), 9.27 (1H, s), 8.45 (1H, d), 8.33-8.30 (2H, m), 8.15 (1H, d), 8.03-7.93 (7H, m), 7.79- 7.41 (18H, m) 2-5 δ = 9.60 (1H, d), 9.27 (1H, s), 8.45-8.30 (4H, m), 8.15 (1H, d), 8.03 (1H, d), 7.94-7.93 (4H, m), 7.75 7.41 (19H, m) 2-8 δ = 9.60 (1H, d), 9.27 (1H, s), 8.45 (1H, d), 8.33-8.30 (2H, m), 8.15 (1H, d), 8.03-7.93 (5H, m), 7.75 7.41 (14H, m), 7.25 (6H, m) 2-77 δ = 9.60 (1H, d), 9.27 (1H, s), 8.55 (1H, d), 8.45 (1H, d), 8.33-8.30 (3H, m), 8.15 (1H, d), 8.03-7.98 ( 6H, m), 7.70-7.49 (12H, m) 3-2 δ = 8.55(1H, d), 8.45(1H, d), 8.30(1H, d), 8.19(1H, d), 8.13(1H, d), 8.00~7.89(6H, m), 7.77(2H, m), 7.62 to 7.35 (15H, m), 7.20 to 7.16 (2H, m) 3-3 δ = 8.55(1H, d), 8.45(1H, d), 8.30(1H, d), 8.19(1H, d), 8.13(1H, d), 8.00 to 7.89(6H, m), 7.77-7.75( 4H, m), 7.62 to 7.35 (13H, m), 7.25 to 7.16 (6H, m) 3-12 δ = 8.55(1H, d), 8.45(1H, d), 8.30(1H, d), 8.19~7.89(11H, m), 7.77(2H, m), 7.62~7.31(14H, m), 7.20~ 7.16 (2H, m) 4-3 δ = 8.55 (1H, d), 8.30 (1H, d), 8.21-8.13 (3H, m), 7.99-7.89 (4H, m), 7.77-7.35 (17H, m), 7.20-7.16 (2H, m) ) 4-4 δ = 8.55 (1H, d), 8.30 (1H, d), 8.19-8.13 (2H, m), 7.99-7.89 (8H, m), 7.77-7.75 (3H, m), 7.62-7.35 (11H, m) ), 7.20-7.16 (2H, m) 4-7 δ = 8.55 (1H, d), 8.31-8.30 (3H, d), 8.19-8.13 (2H, m), 7.99-7.89 (5H, m), 7.77-7.75 (5H, m), 7.62-7.35 (14H) , m), 7.20-7.16 (2H, m) 4-9 δ = 8.55 (1H, d), 8.30 (1H, d), 8.19-8.13 (2H, m), 8.03-7.77 (9H, m), 7.62-7.50 (9H, m), 7.36-7.35 (2H, m) ), 7.20-7.16 (2H, m) 4-31 δ = 8.55 (1H, d), 8.30 (1H, d), 8.21-8.13 (4H, m), 7.99-7.89 (4H, m), 7.77-7.35 (20H, m), 7.20-7.16 (2H, m) ) 4-32 δ = 8.55 (1H, d), 8.30 (1H, d), 8.21-8.13 (3H, m), 7.99-7.89 (8H, m), 7.77-7.35 (17H, m), 7.20-7.16 (2H, m) ) 4-42 δ = 8.55 (1H, d), 8.30 (1H, d), 8.19 (1H, d), 8.13 (1H, d), 7.99-7.89 (12H, m), 7.77-7.75 (5H, m), 7.58 ( 1H, d), 7.50-7.35 (8H, m), 7.20-7.16 (2H, m)

compound FD-MS compound FD-MS 1-1 m/z= 701.25 (C ₅₁ H ₃₁ N ₃ O=701.83) 1-5 m/z = 701.25
(C ₅₁ H ₃₁ N ₃ O=701.83) 1-6 m/z= 701.25 (C ₅₁ H ₃₁ N ₃ O=701.83) 1-8 m/z = 701.25
(C ₅₁ H ₃₁ N ₃ O=701.83) 1-40 m/z = 777.28 (C ₅₇ H ₃₅ N ₃ O=777.93) 1-43 m/z= 853.31
(C ₆₃ H ₃₉ N ₃ O=854.02) 1-45 m/z= 655.17 (C ₄₅ H ₂₅ N ₃ OS=655.78) 1-46 m/z = 639.19
(C ₄₅ H ₂₅ N ₃ O ₂ =639.71) 1-47 m/z= 655.17 (C ₄₅ H ₂₅ N ₃ OS=655.78) 1-53 m/z = 639.19
(C ₄₅ H ₂₅ N ₃ O ₂ =639.71) 1-64 m/z= 731.20 (C ₅₁ H ₂₉ N ₃ OS=731.87) 1-67 m/z = 731.20
(C ₅₁ H ₂₉ N ₃ OS=731.87) 1-69 m/z= 731.20 (C ₅₁ H ₂₉ N ₃ OS=731.87) 1-70 m/z = 715.23
(C ₅₁ H ₂₉ N ₃ O ₂ =715.81) 1-71 m/z= 731.20 (C ₅₁ H ₂₉ N ₃ OS=731.87) 1-74 m/z = 741.28
(C ₅₄ H ₃₅ N ₃ O=741.89) 1-75 m/z=865.31 (C ₆₄ H ₃₉ N ₃ O=866.04) 1-79 m/z = 863.29
(C ₆₄ H ₃₇ N ₃ O=864.02) 1-95 m/z = 807.23 (C ₅₇ H ₃₃ N ₃ OS=807.97) 1-103 m/z = 817.31
(C ₆₀ H ₃₉ N ₃ O=817.99) 1-114 m/z= 701.25 (C ₅₁ H ₃₁ N ₃ O=701.83) 1-167 m/z = 701.25
(C ₅₁ H ₃₁ N ₃ O=701.83) 1-205 m/z = 639.19 (C ₄₅ H ₂₅ N ₃ O ₂ =639.71) 1-282 m/z = 639.19
(C ₄₅ H ₂₅ N ₃ O ₂ =639.71) 2-1 m/z= 717.22 (C ₅₁ H ₃₁ N ₃ S=717.89) 2-5 m/z = 717.22
(C ₅₁ H ₃₁ N ₃ S=717.89) 2-8 m/z= 717.22 (C ₅₁ H ₃₁ N ₃ S=717.89) 2-77 m/z = 747.18
(C ₅₁ H ₂₉ N ₃ S ₂ =747.93) 3-2 m/z= 666.21 (C ₄₈ H ₃₀ N ₂ S=666.84) 3-3 m/z = 742.24
(C ₅₄ H ₃₄ N ₂ S=742.94) 3-12 m/z= 756.22 (C ₅₄ H ₃₂ N ₂ OS=756.92) 4-3 m/z = 560.23
(C ₄₂ H ₂₈ N ₂ =560.70) 4-4 m/z = 560.23 (C ₄₂ H ₂₈ N ₂ =560.70) 4-7 m/z = 636.26
(C ₄₈ H ₃₂ N ₂ =636.80) 4-9 m/z = 534.21 (C ₄₀ H ₂₆ N ₂ =534.66) 4-31 m/z = 636.26
(C ₄₈ H ₃₂ N ₂ =636.80) 4-32 m/z = 636.26 (C ₄₈ H ₃₂ N ₂ =636.80) 4-42 m/z = 636.26
(C ₄₈ H ₃₂ N ₂ =636.80)

<Experimental Example 1>

(1) Fabrication of an organic light emitting device

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,500 Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic washing was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., and dried. 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. The emission layer was deposited by depositing 400 Å of the compound of Formula 1 described in Table 5 below as a host, and doping a green phosphorescent dopant [Ir(ppy) ₃ ] by 7% of the deposition thickness of the emission layer. Then, BCP (bathocuproine) was deposited at 60 Å as a hole blocking layer, and Alq3 was deposited as 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. An electroluminescent device was manufactured.

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.

The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured with M7000 of McScience, and the reference luminance was 6,000 through the life instrumentation measuring device (M6000) manufactured by McScience with the measurement result. At cd/m ² , T ₉₀ was measured.

The results of measuring the driving voltage, luminous efficiency, color (EL color), and lifespan of the organic light-emitting device manufactured according to the present invention are shown in Table 5 below.

light emitting layer
compound drive voltage
(V) efficiency
(cd/A) color
EL color life span
(T ₉₀ ) Example 1 1-1 4.78 70.3 green 234 Example 2 1-5 4.35 79.2 382 Example 3 1-6 4.67 72.6 390 Example 4 1-8 4.33 74.2 405 Example 5 1-40 4.67 71.5 356 Example 6 1-45 4.69 70.9 271 Example 7 1-46 4.61 71.6 347 Example 8 1-47 4.67 71.9 277 Example 9 1-53 4.32 71.5 289 Example 10 1-64 4.91 70.1 200 Example 11 1-67 4.35 78.9 239 Example 12 1-69 4.41 75.8 249 Example 13 1-70 4.33 75.2 246 Example 14 1-71 4.13 78.4 242 Example 15 1-74 4.31 79.2 261 Example 16 1-75 4.36 78.9 256 Example 17 1-79 4.69 71.6 251 Example 18 1-95 4.42 75.7 237 Example 19 1-103 4.38 76.4 250 Example 20 1-114 4.66 73.3 360 Example 21 1-167 4.45 72.8 370 Example 22 1-205 4.56 70.3 352 Example 23 1-282 4.60 71.1 271 Example 24 2-1 4.78 70.3 205 Example 25 2-5 4.65 73.6 333 Example 26 2-8 4.53 72.2 356 Example 27 2-77 4.91 69.8 150 Comparative Example 1 Ref. One 5.37 63.5 112 Comparative Example 2 Ref. 2 4.85 59.8 108 Comparative Example 3 Ref. 3 5.33 68.2 93 Comparative Example 4 Ref. 4 5.82 60.8 88 Comparative Example 5 Ref. 5 5.03 48.7 69 Comparative Example 6 Ref. 6 5.47 41.2 57 Comparative Example 7 Ref. 7 5.66 45.8 48 Comparative Example 8 Ref. 8 4.42 45.7 40

As can be seen from the results in Table 5, the organic electroluminescent device using the organic electroluminescent device light emitting layer material of the present invention has a lower driving voltage than Comparative Examples 1 to 8, and not only improved luminous efficiency, but also significantly improved lifespan. .

The difference in effectiveness of the present invention and the cited invention from the viewpoint of orbital delocalization is as follows:

As confirmed in Table 6 below, Comparative Example compound Ref. The LUMO orbitals of 1 and 2 are localized from triazine to biphenyl. However, when a terphenyl substituent is introduced as in Compound 1-167 of the present invention, the LUMO orbital is delocalized and the stability and mobility of electrons are improved, thereby improving the lifespan of the device.

As confirmed in Table 7 below, Comparative Example compound Ref. 3 and 4 are adjacent to triazine, and a phenyl group is substituted. Since there is no extended aryl substituent, HOMO and LUMO orbitals are not distributed, and HOMO and LUMO are overlapped on triphenylene and heteroaryl, resulting in lower electron and hole stability and lower efficiency and lifetime.

As confirmed in Table 8 below, Comparative Example compound Ref. 5 and 6 introduced a phenyl linker between triazine and triphenylene to separate LUMO and HOMO orbitals, and relatively localized HOMO orbitals to triphenylene and high HOMO levels were measured. This inhibits the movement of holes transferred from the common layer to the light emitting layer of the device and lowers the efficiency and lifetime.

As confirmed in Table 9 below, Comparative Example compound Ref. 7 and 8 are substituted with triphenylene and aryl based on triazine or substituted with dibenzofuran and aryl. In such a structure, since the overlap of HOMO and LUMO orbitals occurs, stability of electrons and holes is lowered, and efficiency and lifetime are lowered.

As can be seen in Table 10 below, in the compound of Formula 1 of the present invention, triphenylene and heteroaryl are combined with triazine as the center, and an aryl group, a fluorene group, and a heteroaryl group may be bonded as additional substituents. there is.

In the compounds 1-6 and 1-8 of the present invention, the terphenyl group in which the HOMO orbital is distributed is bonded, and the HOMO orbital expansion and the HOMO level increase are measured according to the extension of the phenyl group, which improves hole mobility.

As can be seen in Table 11 below, compounds 1-74, 1-75, and 1-79 of the present invention are bonded to a fluorene group having a HOMO orbital distributed therein, so that methyl-fluorene, phenyl-fluorene, and spiro-fluorene have a HOMO level in the order. Elevation is measured, forming broad LUMO orbitals across triphenylene, triazine, and heteroaryl, stabilizing holes and electrons, and forming an appropriate charge balance.

As can be seen in Table 12 below, the compound 1-205 of the present invention is composed of triphenylene having HOMO orbital distributed, dibenzofuran having LUMO orbital distributed, triazine, and dibenzo which can relatively stabilize electrons. The furan participates in the LUMO orbital to improve the electron stability. In compound 1-67 of the present invention, a meta-phenyl linker is introduced between dibenzothiophene and triazine to form perfect separation of HOMO and LUMO, so a relatively high band gap and T ₁ level are measured. In this regard, 1-64, 2-77 introduces a para-phenyl linker, a smaller band gap and T ₁ level than compound 1-67 is measured.

<Experimental Example 2>

(1) Manufacture of organic light emitting device

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,500 Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic washing was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., and dried. 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. The light emitting layer is, as described in Table 13 below, one type of compound represented by Formula 1 of the present invention as a host (N-type) and one type of compound represented by Formula 13 or 14 of the present invention (P-type) ) or the compound (N-type) represented by Formula 1 of the present invention and one type of comparative compound (P-type) were pre-mixed and then deposited to a thickness of 400 Å in one park, and a green phosphorescent dopant [Ir(ppy) ₃ ] was deposited by doping in an amount of 7 wt% of the thickness of the light emitting layer deposition. Then, BCP (bathocuproine) was deposited as a hole blocking layer at 60 Å, and Alq ₃ as an electron transport layer was deposited thereon to a thickness of 200 Å.

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 (Examples 30 to 54 and Comparative Examples 9 to 20).

Meanwhile, all organic compounds required for manufacturing OLED devices were used by vacuum sublimation purification under 10 ^-8 to 10 ^-6 torr for each material.

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

For the organic light emitting devices of Examples 30 to 54 and Comparative Examples 9 to 20 prepared as described above, electroluminescence (EL) characteristics were measured with M7000 manufactured by McScience, and the lifespan equipment manufactured by McScience based on the measurement results When the reference luminance was 6,000 cd/m ² through a measuring device (M6000), T ₉₀ was measured. Here, T ₉₀ denotes a lifetime (unit: h, time) that is 90% of the initial luminance.

The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light emitting diode manufactured according to the present invention are shown in Table 13 below.

light emitting layer
compound ratio drive voltage
(V) efficiency
(cd/A) color
EL color life span
(T ₉₀ ) Example 28 1-5:
3-2 1:8 4.72 53.8 green 327 Example 29 1: 5 4.70 56.1 433 Example 30 1: 2 4.35 79.2 599 Example 31 1:1 4.41 75.8 591 Example 32 2:1 4.67 71.2 540 Example 33 5 : 1 4.32 68.3 433 Example 34 8:1 4.21 67.0 325 Example 35 1-6:
3-3 1: 2 4.33 75.2 620 Example 36 1:1 4.48 70.2 582 Example 37 2:1 4.69 69.2 543 Example 38 1-8:
3-12 1: 2 4.33 75.2 679 Example 39 1:1 4.48 70.2 546 Example 40 2:1 4.69 69.2 525 Example 41 1-53:
4-4 1: 2 4.33 75.2 569 Example 42 1:1 4.48 70.2 543 Example 43 2:1 4.69 69.2 518 Example 44 1-74:
4-7 1: 2 4.33 74.2 562 Example 45 1:1 4.42 72.2 553 Example 46 2:1 4.66 71.2 528 Example 47 1-205:
4-31 1: 2 4.31 79.2 586 Example 48 1:1 4.42 75.7 558 Example 49 2:1 4.66 71.1 536 Example 50 2-5:
3-2 1: 2 4.45 72.2 545 Example 51 1:1 4.51 70.8 523 Example 52 2:1 4.77 68.2 499 Example 53 2-77:
4-32 1: 2 4.48 71.4 539 Example 54 1:1 4.55 70.8 523 Example 55 2:1 4.75 68.5 480 Comparative Example 9 1-8:
Ref. 9 1: 2 5.72 53.1 305 Comparative Example 10 1:1 5.70 56.1 214 Comparative Example 11 2:1 5.80 58.3 122 Comparative Example 12 1-8:
Ref. 10 1: 2 5.41 54.6 386 Comparative Example 13 1:1 5.20 56.9 301 Comparative Example 14 2:1 5.64 58.1 229 Comparative Example 15 1-8:
Ref. 11 1: 2 5.40 54.7 453 Comparative Example 16 1:1 5.52 54.5 320 Comparative Example 17 2:1 5.57 49.4 300 Comparative Example 18 1-8:
Ref. 12 1: 2 5.31 49.9 127 Comparative Example 19 1:1 5.68 48.1 78 Comparative Example 20 2:1 5.60 41.3 43

In addition, the compounds used in Comparative Examples 9 to 20, Ref. 9 to Ref. 12 is as follows.

Looking at the results of Table 13, when the compound of the compound (N type) represented by Formula 1 of the present invention and the compound represented by Formula 2 or 3 of the present invention (p type) are simultaneously included, better efficiency and A lifetime effect is obtained. This result is considered to be due to the exciplex phenomenon that occurs when both compounds are included at the same time.

The exciplex phenomenon is a phenomenon in which the energy of the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host) is emitted through electron exchange between two molecules. When an exciplex phenomenon occurs between two molecules, Reverse Intersystem Crossing (RISC) occurs, thereby increasing the internal quantum efficiency of fluorescence to 100%. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as hosts of the emission layer, holes are injected into the p-host and electrons are transferred to the n-host Since it is injected, the driving voltage can be lowered, thereby improving the lifespan.

In the present invention, the donor role is performed by the compound represented by Chemical Formula 2 or 3, and the acceptor role is performed by the compound represented by Chemical Formula 1, and when these are used as the light emitting layer host, excellent device properties indicates.

In this regard, the compound represented by Formula 2 of the present invention (Compound 3-2) and the compound represented by Formula 3 of the present invention (Compound 4-31), Comparative Example compound Ref. 9 to Ref. The HOMO orbitals and LUMO orbitals of 12 are shown in Table 14 below.

As confirmed in Table 14 above, the comparative compound Ref. The HOMO orbital of 9 is localized to the terminal two carbazoles and has a low HOMO level and hole mobility. This causes an imbalance of holes and electrons in the device, thereby reducing the lifespan.

The comparative compound Ref. The HOMO orbital of 10 is delocalized to carbazole and triphenylene, so Ref. Although it has a HOMO level higher than 9 and the hole mobility is improved, it still causes device imbalance.

When there is no aryl substituent at position 4 of the core of dibenzothiophene (DBT) as in Ref 11, which is a comparative compound, dibenzothiophene (DBT) with good reactivity at position 4 of the core Since there is no protective substituent in the compound, molecular stability is lowered, and compared to Compound 3-2, the LUMO orbital is localized in the dibenzothiophene (DBT) core, thereby not effectively stabilizing electrons and reducing the lifespan.

The comparative compound Ref. It can be seen that when p-type is used as an amine such as 12, device imbalance occurs and lifespan is reduced due to too high HOMO level and fast hole mobility.

The HOMO level of compound 3-2 represented by Formula 2 of the present invention and compound 4-31 represented by Formula 3 of the present invention is widely delocalized in two carbazoles. Therefore, when the compound represented by Formula 1 of the present invention is used in an organic light emitting device at the same time as the compound represented by Formula 2 or Formula 3 of the present invention, compared to basic carbazole, HOMO Level, hole mobility, and stability are increased to improve the lifespan of the organic light emitting diode. In particular, a structure such as Compound 3-2 introduces a dibenzothiophene (DBT) core and an aryl group in consideration of electron stability to effectively stabilize electrons and improve the lifespan of the organic light emitting diode.

Claims (15)

Heterocyclic compound represented by Formula 1 below:
[Formula 1]

In Formula 1,
X is O or S;
R1 to R14 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)R101R202; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other combine with each other 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 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,
R15 is a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or -Si(Ar1) ₃ , wherein each Ar1 included in (Ar1) ₃ is the same as each other. or different, each independently selected from a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C2 to C60 heteroaryl group,
L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted C6 to C60 arylene group or a substituted or unsubstituted C2 to C60 heteroarylene group,
m is an integer from 0 to 3, when m is 0, L1 is a direct bond, when m is 2 or 3, each L1 is the same as or different from each other, and each is independently selected;
n is an integer from 0 to 3, when n is 0, L2 is a direct bond, when n is 2 or 3, each L2 is the same as or different from each other, and each is independently selected;
o is a natural number from 1 to 3, and when o is 2 or 3, each R15 is the same as or different from each other, and each is independently selected;
p is an integer of 0 to 4, and when p is 2 to 4, R5 are the same as or different from each other, and are each independently selected;
q is an integer from 0 to 3, and when q is 2 or 3, R6 are the same as or different from each other, and are each independently selected;
However, -(L1)m-(L2)n-(R15)o is not a phenyl or biphenyl group. According to claim 1,
The compound represented by Formula 1 is a heterocyclic compound, characterized in that it is a compound represented by Formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,
The definitions of X, R1 to R14, m, p, and q are the same as in Formula 1 above,
Y is C, O, or S;
R16 to R26 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; And a substituted or unsubstituted C2 to C60 heteroaryl group; selected from the group consisting of, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to to form a C60 heterocyclic ring,
r and s are the same as or different from each other and are each independently an integer of 0 to 4,
t, v, and b are the same as or different from each other and are each independently an integer from 0 to 4,
u, w, c, d, and e are the same as or different from each other and are each independently an integer from 0 to 5;
a is a natural number from 1 to 3,
When each of R16, R22, and R23 to R26 is two or more, they are the same as or different from each other, and are each independently selected;
At least one of m, r and s is non-zero. 3. The method of claim 2,
R16 to R19 and R22 to R26 are the same as or different from each other, and each independently represent hydrogen, deuterium, or a C1 to C5 alkyl group,
R21 and R22 are the same as or different from each other and are each independently a C1 to C5 alkyl or a substituted or unsubstituted phenyl group, or a heterocyclic compound, characterized in that they combine with each other to form a substituted or unsubstituted fluorenyl group. According to claim 1,
The compound represented by Formula 1 is a heterocyclic compound, characterized in that it is a 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 a; at least one organic material layer provided between the first electrode and the second electrode,
The organic material layer is an organic light-emitting device comprising the heterocyclic compound according to any one of claims 1 to 4. 6. The method of claim 5,
The organic material layer includes at least one layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer,
The at least one layer is an organic light-emitting device comprising the heterocyclic compound according to any one of claims 1 to 4. 7. The method of claim 6,
The organic material layer includes a light emitting layer,
The light emitting layer is an organic light emitting device comprising the heterocyclic compound according to any one of claims 1 to 4. 6. The method of claim 5,
The organic material layer is an organic light emitting device comprising the heterocyclic compound according to any one of claims 1 to 4 and the heterocyclic compound represented by the following Chemical Formula 2:
[Formula 2]

In Formula 2,
X is N, O or S;
R27 and R28 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group,
R29 and R30 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; -SiR201R202R203, -P(=O)R201R202; and 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 selected from the group consisting of an amine group substituted or unsubstituted, or each other Two or more adjacent groups combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 hetero ring,
R201, R202, and R203 are the same as or different from each other, and each independently represents hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted a C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group,
f and g are the same as or different from each other, and are each independently an integer of 0 to 7. 9. The method of claim 8,
An organic light-emitting device, characterized in that the compound represented by Formula 2 is a heterocyclic compound represented by Formula 2-1:
[Formula 2-1]

In Formula 2-1,
R31 and R32 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C60 aryl group and a substituted or unsubstituted C2 to C60 heteroaryl group,
h is an integer from 0 to 4, i is an integer from 0 to 2,
L3 is a direct bond, a substituted or unsubstituted C1 to C60 arylene group, or a substituted or unsubstituted C2 to C60 heteroarylene group,
Ar2 and Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted C1 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group,
The definitions of R29 and R30, f and g are the same as those in Formula 2 above. 9. The method of claim 8,
The compound represented by Formula 2 is an organic light emitting device, characterized in that it is represented by any one of the following compounds:

9. The method of claim 8,
The organic material layer includes a light emitting layer,
The light emitting layer includes a host material,
The host material is an organic light emitting device comprising the heterocyclic compound according to any one of claims 1 to 4 and the heterocyclic compound represented by Formula 2 above. 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 4 and the heterocyclic compound represented by the following Chemical Formula 2:
[Formula 2]

In Formula 2,
X is N, O or S;
R27 and R28 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group,
R29 and R30 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; -SiR201R202R203, -P(=O)R201R202; and 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 selected from the group consisting of an amine group substituted or unsubstituted, or each other Two or more adjacent groups combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 hetero ring,
R201, R202, and R203 are the same as or different from each other, and each independently represents hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted a C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group,
f and g are the same as or different from each other, and are each independently an integer of 0 to 7. 13. The method of claim 12,
The composition for an organic material layer of an organic light emitting device, wherein the weight ratio of the heterocyclic compound according to any one of claims 1 to 4: the heterocyclic compound represented by Formula 2 is 1:10 to 10:1. 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;
The forming of the organic material layer is a method of manufacturing an organic light emitting device comprising the step of forming one or more organic material layers using the composition for an organic material layer according to claim 12. 15. The method of claim 14,
In the step of forming the organic layer, the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 included in the composition for the organic layer are pre-mixed to form a composition for the organic layer, and this is a vacuum deposition method or a solution application method A method of manufacturing an organic light-emitting device, characterized in that by coating with an organic material layer is formed.

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