KR102180763B1 - Hetero-cyclic compound and organic light emitting device using the same - Google Patents

Abstract

The present application provides a heterocyclic compound capable of greatly improving the lifespan, efficiency, electrochemical stability, and thermal stability of the organic light-emitting device, and an organic light-emitting device in which the heterocyclic compound is contained in an organic compound layer.

Description

Heterocyclic compound and organic light emitting device using the same {HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME}

The present application relates to a heterocyclic compound and an organic light emitting device using the same.

An electroluminescent device is a type of self-luminous display device, and has advantages in that it has a wide viewing angle, excellent contrast, and a 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 are combined in the organic thin film to form a pair and then emit light while disappearing. The organic thin film may be composed of a single layer or multiple layers as necessary.

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

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

U.S. Patent 4,356,429

A compound having a chemical structure that can satisfy conditions required for materials usable in an organic light-emitting device, such as an appropriate energy level, electrochemical stability, and thermal stability, and can play various roles required in an organic light-emitting device depending on a substituent There is a need for research on an organic light-emitting device including a.

An exemplary embodiment of the present application provides a heterocyclic compound represented by the following Chemical Formula 1:

[Formula 1]

In Formula 1,

X1 is S or O,

At least one of Y1 to Y4 is N, the rest are N or CR6,

At least one of R1 to R6 is represented by -(L)p-(Y)q, and the others are each independently hydrogen; heavy hydrogen; Halogen group; -CN; A substituted or unsubstituted C ₁ to C ₆₀ alkyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; A substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; A substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; A substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group; A substituted or unsubstituted C ₆ to C ₆₀ aryl group; A substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R";-P(=O)RR'; And a C ₁ to C ₂₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a substituted or unsubstituted C ₂ to C ₆₀ Selected from the group consisting of an amine group substituted or unsubstituted with a heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring,

L is a direct bond; A substituted or unsubstituted C ₆ to C ₆₀ arylene group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroarylene group,

Y is hydrogen; heavy hydrogen; Halogen group; -CN; A substituted or unsubstituted C ₁ to C ₆₀ alkyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; A substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; A substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; A substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group; A substituted or unsubstituted C ₆ to C ₆₀ aryl group; A substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R";-P(=O)RR'; And a C ₁ to C ₂₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a substituted or unsubstituted C ₂ to C ₆₀ It is selected from the group consisting of an amine group substituted or unsubstituted with a heteroaryl group,

p is 0 to 10, q is 1 to 10,

R, R'and R" are the same as or different from each other, and each independently hydrogen; deuterium; -CN; substituted or unsubstituted C ₁ to C ₆₀ straight or branched alkyl group; substituted or unsubstituted C ₃ to C ₆₀ monocyclic or polycyclic cycloalkyl group; substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl group; or substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl group.

In addition, another exemplary embodiment of the present application is an organic light emitting device comprising an anode, a cathode, and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers is a heterocyclic compound represented by Formula 1 It provides an organic light emitting device comprising a.

The heterocyclic compound according to an exemplary embodiment of the present application may be used as an organic material layer material of an organic light emitting device. The heterocyclic compound may be used as a material such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer in an organic light emitting device. In particular, the heterocyclic compound represented by Formula 1 may be used as a material for an electron transport layer, a hole transport layer, or a light emitting layer of an organic light emitting device. In addition, when used in the heterocyclic compound organic light-emitting device represented by Formula 1, the driving voltage of the device may be lowered, light efficiency may be improved, and the lifespan characteristics of the device may be improved by thermal stability of the compound.

1 to 3 are diagrams each schematically showing a stacked structure of an organic light emitting diode according to an exemplary embodiment of the present application.
4 shows the LC/MS measurement results of Compound 8.
5 shows the LC/MS measurement results of Compound 9.
6 shows the LC/MS measurement results of Compound 19.
7 shows the LC/MS measurement result of Compound 21.
8 shows the LC/MS measurement results of Compound 23.
9 shows the LC/MS measurement results of Compound 29.
10 shows the LC/MS measurement results of Compound 79.
11 shows the LC/MS measurement result of Compound 83.
12 shows the LC/MS measurement results of Compound 148.
<Explanation of the main symbols in the drawings>
100: substrate
200: anode
300: organic material layer
301: hole injection layer
302: hole transport layer
303: light emitting layer
304: hole blocking layer
305: electron transport layer
306: electron injection layer
400: cathode

Hereinafter, the present application will be described in detail.

The heterocyclic compound according to an exemplary embodiment of the present application is characterized in that it is represented by Formula 1 above. More specifically, the heterocyclic compound represented by Formula 1 may be used as an organic material layer material of an organic light-emitting device due to the structural characteristics of the core structure and substituent as described above.

According to an exemplary embodiment of the present application, Formula 1 may be represented by any one of Formulas 2 to 9 below.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

In Formulas 2 to 9, R1 is represented by -(L)p-(Y)q,

L, Y, p and q are the same as defined in Chemical Formula 1.

In the exemplary embodiment of the present application, Y in Formula 1 is hydrogen; heavy hydrogen; A substituted or unsubstituted C ₆ to C ₆₀ aryl group; Or it may be a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group.

In the exemplary embodiment of the present application, R2 to R5 in Formula 1 may each independently be hydrogen or deuterium.

In the present application, the substituents of Formulas 1 to 9 will be described in more detail as follows.

In the present specification, "substituted or unsubstituted" means deuterium; Halogen group; -CN; A C ₁ to C ₆₀ alkyl group; C ₂ to C ₆₀ alkenyl group; Alkynyl group of C ₂ to C ₆₀ ; C ₃ to C ₆₀ cycloalkyl group; C ₂ to C ₆₀ heterocycloalkyl group; C ₆ to C ₆₀ aryl group; C ₂ to C ₆₀ heteroaryl group; -SiRR'R"; -P(=O)RR'; C ₁ to C ₂₀ alkylamine group; C ₆ to C ₆₀ arylamine group; And C ₂ to C ₆₀ substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroarylamine group, or substituted or unsubstituted with a substituent to which two or more of the substituents are bonded, or two or more substituents selected from the substituents are connected. It means substituted or unsubstituted with a substituent. For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected. The additional substituents may be further substituted. The R, R'and R" are the same as or different from each other, and each independently hydrogen; deuterium; -CN; a substituted or unsubstituted C ₁ to C ₆₀ alkyl group; a substituted or unsubstituted C ₃ to C ₆₀ cyclo Alkyl group; A substituted or unsubstituted C ₆ to C ₆₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group.

According to an exemplary embodiment of the present application, the "substituted or unsubstituted" means deuterium, a halogen group, -CN, SiRR'R", P(=O)RR', a straight or branched alkyl group of C ₁ to C ₂₀ It is unsubstituted or substituted with one or more substituents selected from the group consisting of a C ₆ to C ₆₀ aryl group, and a C ₂ to C ₆₀ heteroaryl group,

The R, R'and R" are the same as or different from each other, and each independently hydrogen; deuterium; -CN; deuterium, halogen group, -CN, a C ₁ to C ₂₀ alkyl group, a C ₆ to C ₆₀ aryl group, and C ₂ to C ₆₀ substituted heteroaryl or unsubstituted alkyl group of C ₁ to C _60; an aryl group of deuterium, halogen, -CN, C ₁ to C ₂₀ alkyl group, C ₆ to C ₆₀ a, and C ₂ to a substituted or unsubstituted group of the C ₆₀ heteroaryl C ₃ to C ₆₀ cycloalkyl group; a deuterium, a halogen, -CN, an alkyl group of C ₁ to C _20, C ₆ to C ₆₀ aryl, and C ₂ to C ₆₀ substituted or unsubstituted group heteroaryl C ₆ to C ₆₀ aryl group; or an alkyl group of deuterium, halogen, -CN, C ₁ to C _20, C ₆ to C ₆₀ aryl, and C ₂ to C ₆₀ It is a C ₂ to C ₆₀ heteroaryl group unsubstituted or substituted with a heteroaryl group of.

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

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

In the present specification, the alkyl group includes a straight chain or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, 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 are not limited thereto.

In the present specification, the alkenyl group includes a linear or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically, 2 to 20. Specific examples include 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, and styrenyl group, but are not limited thereto.

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

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic having 3 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic refers to a group in which a cycloalkyl group is directly connected or condensed with another ring group. Here, the other cyclic group may be a cycloalkyl group, but may be a different type of cyclic group, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specifically, a 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 are not limited thereto.

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

In the present specification, the aryl group includes monocyclic or polycyclic having 6 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic means a group in which an aryl group is directly connected or condensed with another ring group. Here, the other cyclic group may be an aryl group, but may be another type of cyclic group such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, and the like. The aryl group includes a spiro group. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group include phenyl group, biphenyl group, triphenyl group, naphthyl group, anthryl group, chrysenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenalenyl group, pyre Nyl group, tetrasenyl 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 are not limited thereto.

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

In the present specification, the heteroaryl group includes S, O, Se, N or Si as a hetero atom, and includes a monocyclic or polycyclic having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic means a group in which a heteroaryl group is directly connected or condensed with another ring group. Here, the other cyclic group may be a heteroaryl group, but may be another type of cyclic group such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, and the like. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heteroaryl group include a pyridyl group, pyrrolyl group, pyrimidyl group, pyridazinyl group, furanyl group, thiophene group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl Group, isothiazolyl group, triazolyl group, furazinyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , Thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolilyl group, naphthyridyl group, acridinyl group, phenanthridyl Nyl group, imidazopyridinyl group, diazanaphthalenyl group, triazaindenyl 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, phenothiathiazinyl 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 ] Carbazolyl group, and the like, but are not limited thereto.

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

In the present specification, an 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 refers to a heteroaryl group having two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aforementioned heteroaryl group may be applied.

이고, 상기 X3 및 X4는 치환 또는 비치환된 C₆ 내지 C₆₀의 방향족 탄화수소 고리; 또는 치환 또는 비치환된 C₂ 내지 C₆₀의 방향족 헤테로 고리일 수 있다.According to an exemplary embodiment of the present application, Y in Formula 1 is

And, X3 and X4 are substituted or unsubstituted C ₆ to C ₆₀ aromatic hydrocarbon rings; Or it may be a substituted or unsubstituted C ₂ to C ₆₀ aromatic hetero ring.

는 하기 구조식들 중 어느 하나로 표시될 수 있으나, 이에만 한정되는 것은 아니다.remind

May be represented by any one of the following structural formulas, but is not limited thereto.

In the above structural formulas, Z ₁ to Z ₃ are the same as or different from each other, and each independently S or O,

Z ₄ to Z ₁₀ are the same as or different from each other, and each independently CR'R",NR', S or O,

R′ and R” are the same as or different from each other, and each independently hydrogen; substituted or unsubstituted C ₁ to C ₆₀ alkyl; or substituted or unsubstituted C ₆ to C ₆₀ aryl.

According to an exemplary embodiment of the present application, Formula 1 may be represented by any one of the following compounds, but is not limited thereto.

In addition, by introducing various substituents into the structure of Formula 1, a compound having the inherent characteristics of the introduced substituent can be synthesized. For example, by introducing a substituent mainly used for the hole injection layer material, the hole transport material, the light emitting layer material and the electron transport layer material used in the manufacture of the organic light emitting device into the core structure, it is possible to synthesize a material that satisfies the conditions required by each organic material layer. I can.

In addition, by introducing various substituents to the structure of Chemical Formula 1, the energy band gap can be finely adjusted, while the properties at the interface between organic substances can be improved, and the use of the material can be varied.

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

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

More specifically, the heterocyclic compound according to an exemplary embodiment of the present application may be prepared from the following Schemes 1 to 4, but is not limited thereto.

[Scheme 1]

[Scheme 2]

[Scheme 3]

[Scheme 4]

In the above Schemes 1 to 4, X is S or O.

Another exemplary embodiment of the present application provides an organic light-emitting device including the heterocyclic compound represented by Chemical Formula 1.

The organic light-emitting device according to the exemplary embodiment of the present application may be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except for forming one or more organic material layers using the aforementioned heterocyclic compound.

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

Specifically, the organic light-emitting device according to the exemplary embodiment of the present application includes an anode, a cathode, and one or more organic material layers provided between the anode and the cathode, and at least one of the organic material layers is a heterocycle represented by Formula 1 Contains compounds.

1 to 3 illustrate a stacking sequence of an electrode and an organic material layer of an organic light emitting device according to an exemplary embodiment of the present application. However, it is not intended that the scope of the present application be limited by these drawings, and the structure of an organic light emitting device known in the art may 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 shown. However, it is not limited to such a structure, and as shown in FIG. 2, an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.

3 illustrates a case in which the organic material layer is a multilayer. 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 lamination structure, and other layers other than the light emitting layer may be omitted, or other necessary functional layers may be further added as necessary.

The organic light-emitting device according to the present specification may be manufactured by materials and methods known in the art, except for including the heterocyclic compound represented by Formula 1 in at least one of the organic material layers.

The heterocyclic compound represented by Formula 1 may constitute one or more of the organic material layers of the organic light-emitting device alone. However, if necessary, the organic material layer may be formed by mixing with other materials.

The heterocyclic compound represented by Formula 1 may be used as a material for an electron transport layer, a hole blocking layer, and a light emitting layer in an organic light emitting device. As an example, the heterocyclic compound represented by Formula 1 may be used as a material for an electron transport layer, a hole transport layer, or a light emitting layer of an organic light emitting device.

In addition, the heterocyclic compound represented by Formula 1 may be used as a material for a light emitting layer in an organic light emitting device. As an example, the heterocyclic compound represented by Formula 1 may be used as a material for a phosphorescent host of an emission layer in an organic light emitting device.

In the organic light-emitting device according to the exemplary embodiment of the present application, materials other than the heterocyclic compound of Formula 1 are exemplified below, but these are for illustration only, and are not intended to limit the scope of the present application. It can be replaced with materials known in.

Materials having a relatively large work function may be used as the cathode material, and transparent conductive oxides, metals, or conductive polymers may be used. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

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

As the hole injection material, a known hole injection material may be used. For example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a phthalocyanine compound disclosed in Advanced Material, 6, p.677 (1994) is described. Starburst type amine derivatives, such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine (m- MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/dodecylbenzenesulfonic acid (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)) can be used.

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

Electron transport materials include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone Derivatives, diphenyl dicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like may be used, and not only low-molecular substances but also high-molecular substances may be used.

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

Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. Further, a fluorescent material may be used as the light emitting material, but may also be used as a phosphorescent material. As the light-emitting material, a material that emits light by combining holes and electrons respectively injected from an anode and a cathode may be used alone, but materials in which a host material and a dopant material are both involved in light emission may be used.

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

The heterocyclic compound according to the exemplary embodiment of the present application may function in an organic electronic device including an organic solar cell, an organic photoreceptor, an organic transistor, etc. in a similar principle to that applied to an organic light emitting device.

Hereinafter, the present specification will be described in more detail through examples, but these are only intended to illustrate the present application and are not intended to limit the scope of the present application.

< Example >

< Synthesis example 1> Preparation of compound 1-1

Preparation of compound 1-3

Compound benzo[b]thiophene-2-ylboronic acid 30g (138 mmol), 2-chloropyridin-3-amine 20g (153 mmol), Pd (PPh ₃ ) ₄ 8.85 g (7.70 mmol), NaHCO ₃ 25.7 g (306 mmol), 600 mL of toluene, 120 mL of EtOH, and 120 mL of H ₂ O were added, followed by nitrogen substitution. reflux It was reacted for 5 hours under conditions and extracted with distilled water, MC and NaCl. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed by a rotary evaporator, and then purified by column chromatography using MC to obtain 27 g (78%) of the title compound 1-3 .

Preparation of compound 1-2

Compound 1-3 12g (53.02 mmol), compound 3-bromobenzoyl chloride 12.8g (58.33 mmol), TEA 8.15 mL (58.33 mmol) and MC 200 mL were added and substituted with nitrogen. After reacting at room temperature for 3 hours, extraction was performed using distilled water and MC. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the mixture was slurried with methanol and filtered to obtain 17 g (80%) of the title compound 1-2 .

Preparation of compound 1-1

Compound 1-2 8.7 g (21.25 mmol), POCl ₃ 2 mL (21.25 mmol), and nitrobenzene 70 mL were added, followed by nitrogen substitution. After reacting at 150° C. for 12 hours, extraction was performed using distilled water, MC and NaCl. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and then Celite, silica gel and florisil were filled, and then filtered with MC to obtain 8 g (96%) of the target compound 1-1 .

< Synthesis example 2> Preparation of compound 2-1

Compound 1-1 15g (38.3 mmol), bis (pinacorato) diboron 14.6g (57.5 mmol), PdCl ₂ (dppf) 1.4g (1.92 mmol), KOAc 7.52g (76.6 mmol) and di 150 mL of oxane was added at 85° C. and reacted for 12 hours, followed by extraction using distilled water, MC and ammonium chloride. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and purified by column chromatography using MC to obtain 16 g (97%) of the title compound 2-1 .

< Synthesis example 3> Preparation of compound 3-1

Preparation of compound 3-3

Compound benzo[b]thiophene-2-ylboronic acid 11.5g (64.6 mmol), 3-bromopyridin-4-amine 12.3g (71.1 mmol), Pd (PPh ₃ ) ₄ 3.73g (3.23 mmol) , NaHCO ₃ 10.8 g (129 mmol), 200 mL of toluene, 40 mL of EtOH and 40 mL of H ₂ O were added, followed by nitrogen substitution. reflux After reacting for 12 hours under conditions, extraction was performed using distilled water, MC and NaCl. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed by a rotary evaporator, and then purified by column chromatography using MC to obtain 13.7 g (78%) of the title compound 3-3 .

Preparation of compound 3-2

Compound 3-3 13.7g (60.5 mmol), compound 3-bromobenzoyl chloride 13.3g (60.5 mmol), TEA 8.45 mL (60.5 mmol) and MC 200 mL were added and substituted with nitrogen. After reacting at room temperature for 3 hours, extraction was performed using distilled water and MC. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the mixture was slurried with methanol and filtered to obtain 19.2 g (77%) of the title compound 3-2 .

Preparation of compound 3-1

Compound 3-2 19.2g (46.9 mmol), POCl ₃ 4.38 mL (46.9 mmol), and nitrobenzene 150 mL were added, followed by nitrogen substitution. After reaction at 150° C. for 24 hours, extraction was performed using distilled water, MC and NaCl. The organic layer was dried over anhydrous MgSO _4, and then the solvent was removed by a rotary evaporator and purified by column chromatography using MC:EA=1:1 to obtain 13.7 g (75%) of the title compound 3-1 .

< Synthesis example 4> Preparation of compound 4-1

Preparation of compound 4-3

Compound benzo[b]thiophene-2-ylboronic acid 40g (224 mmol), 3-bromopyridin-2-amine 26.2g (204 mmol), Pd (PPh ₃ ) ₄ 11.8g (10.2 mmol), NaHCO ₃ 34.3g (408 mmol), 700 mL of toluene, 140 mL of EtOH, and 140 mL of H ₂ O were added, followed by nitrogen substitution. reflux After reacting for 12 hours under conditions, extraction was performed using distilled water, MC and NaCl. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and then purified by column chromatography using MC to obtain 37.7 g (81%) of the title compound 4-3 .

Preparation of compound 4-2

Compound 4-3 37.7 g (166 mmol), compound 3-bromobenzoyl chloride 40.1 g (182 mmol), TEA 25.5 mL (182 mmol) and MC 550 mL were added and substituted with nitrogen. After reacting at room temperature for 3 hours, extraction was performed using distilled water and MC. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed by a rotary evaporator, followed by slurrying with methanol, and then filtered to obtain 49.8 g (73%) of the title compound 4-2 .

Preparation of compound 4-1

Compound 4-2 49.8g (121 mmol), POCl ₃ 11.4 mL (121 mmol), and nitrobenzene 400 mL were added, followed by nitrogen substitution. After reaction at 150° C. for 24 hours, extraction was performed using distilled water, MC, and NaCl. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed by a rotary evaporator, and then purified by column chromatography using MC:EA=1:1 to obtain 39 g (82%) of the title compound 4-1 .

< Synthesis example 5> Preparation of compound 5-1

Preparation of compound 5-4

Compound benzo[b]thiophene-2-ylboronic acid 40g (224 mmol), 2-chloropyridin-3-amine 26.2g (204 mmol), Pd (PPh ₃ ) ₄ 11.8g (10.2 mmol), NaHCO ₃ 34.3 g (408 mmol), 700 mL of toluene, 140 mL of EtOH, and 140 mL of H ₂ O were added, followed by nitrogen substitution. reflux After reacting for 12 hours under conditions, extraction was performed using distilled water, MC and NaCl. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and purified by column chromatography using MC to obtain 37.7 g (81%) of the title compound 5-4 .

Preparation of compound 5-3

Compound 5-4 37.7g (166 mmol), compound ethyl carbonochloridate 19.8g (182 mmol), NaHCO ₃ 52.3g (498 mmol) and 550 mL of chloroform were added thereto, followed by nitrogen substitution. After reacting at room temperature for 3 hours, extraction was performed using distilled water and MC. The organic layer was dried over anhydrous MgSO _4, and then the solvent was removed by a rotary evaporator, and the mixture was slurried with methanol and filtered to obtain 36.2 g (73%) of the title compound 5-3 .

Preparation of compound 5-2

Compound 5-3 36.1g (121 mmol), H ₃ PO ₄ 360 mL and nitrobenzene 400 mL were added, reacted at 150° C. for 17 hours, and extracted with distilled water, MC, and NaCl. The organic layer was dried with anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and then slurry with methanol and filtered to obtain 12.3 g (40%) of the title compound 5-2 .

Preparation of compound 5-1

Compound 5-2 12.1g (48 mmol), POCl3 37g (240 mmol), and DMA 240 mL were added, reacted for 17 hours under reflux, and extracted using distilled water, MC, and NaCl. The organic layer was dried over anhydrous MgSO ₄ and then purified by column chromatography using MC/Hexane from which the solvent was removed by a rotary evaporator to obtain 2.6 g (20%) of the title compound 5-1 .

< Manufacturing example 1> Preparation of compound 8

Compound 2-1 5g (11.4 mmol), Compound 2-bromo-4,6-diphenylpyrimidine 3.55g (11.4 mmol), Pd (PPh ₃ ) ₄ 660 mg (0.57 mmol), K ₂ CO ₃ 4.73g (34.22mmol), 50mL of toluene, 10mL of EtOH, and 10mL of H ₂ O were added, followed by nitrogen substitution. After refluxing and reacting for 12 hours, extraction was performed using distilled water, MC, and NaCl. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed by a rotary evaporator, and then purified by column chromatography using MC:ethyl acetate=10:1 to obtain 4.5 g (81%) of the title compound 8 .

< Manufacturing example 2> Preparation of compound 9

Compound 2-1 5g (11.4 mmol), Compound 2-bromo-4,6-diphenylpyrimidine 3.55g (11.4 mmol), Pd (PPh ₃ ) ₄ 660 mg (0.57 mmol), K ₂ CO ₃ 4.73g (34.22mmol), 50mL of toluene, 10mL of EtOH, and 10mL of H ₂ O were added, followed by nitrogen substitution. After refluxing and reacting for 12 hours, extraction was performed using distilled water, MC, and NaCl. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed by a rotary evaporator, and then purified by column chromatography using MC:ethyl acetate=10:1 to obtain 4.2 g (81%) of the title compound 9 .

< Manufacturing example 3> Preparation of compound 19

Compound 1-1 5g (12.8 mmol), Compound 9-phenyl-9H,9'H-3,3'-bicarbazole 5.27g (12.9 mmol), CuI 2.45g (12.9 mmol), K ₃ PO ₄ 5.48g (25.8mmol), 1.5mL (12.9mmol) of 1,2-cyclohexanediamine, and 50mL of 1,4-dioxane were added, followed by nitrogen substitution. The reaction was performed under reflux for 12 hours, and extraction was performed using distilled water, MC and NaCl. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed by a rotary evaporator, and then purified by column chromatography using MC:ethyl acetate=10:1 to obtain 7g (86%) of the title compound 19 .

< Manufacturing example 4> Preparation of compound 21

Compound 1-1 5g (12.8 mmol), compound dibenzo[b,d]thiophen-4-ylboronic acid 2.92g (12.8 mmol), Pd (PPh ₃ ) ₄ 740 mg (0.64 mmol), K ₂ CO ₃ 5.3 g (38.4 mmol), 50 mL of toluene, 10 mL of EtOH, and 10 mL of H ₂ O were added, followed by nitrogen substitution. The reaction was performed under reflux for 12 hours, and extraction was performed using distilled water, MC and NaCl. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed by a rotary evaporator, and then purified by column chromatography using MC:ethyl acetate=10:1 to obtain 5.6 g (91%) of the title compound 21 .

< Manufacturing example 5> Preparation of compound 23

Compound 1-1 5g (12.8mmol), Compound 7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole 3.75g (12.8mmol), CuI 2.43g (12.8mmol) ), K ₃ PO ₄ 5.42 g (25.55 mmol), 1,2-cyclohexanediamine 1.5 mL (12.8 mmol), and 1,4-dioxane 50 mL were added, followed by nitrogen substitution. The reaction was performed under reflux for 12 hours, and extraction was performed using distilled water, MC and NaCl. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed by a rotary evaporator, and then purified by column chromatography using MC:ethyl acetate=10:1 to obtain 6g (86%) of the title compound 23 .

< Manufacturing example 6> Preparation of compound 29

Compound 2-1 5g(11.4mmol), 9-(4-bromophenyl)-9H-carbazole 3.65g(11.4mmol), Pd(PPh ₃ ) ₄ 660mg(0.57mmol), K ₂ CO ₃ 4.73g (34.22mmol), 50mL of toluene, 10mL of EtOH, and 10mL of H ₂ O were added, followed by nitrogen substitution. After refluxing and reacting for 12 hours, extraction was performed using distilled water, MC, and NaCl. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed by a rotary evaporator, and then purified by column chromatography using MC:ethyl acetate=20:1 to obtain 5.4 g (78%) of the title compound 29 .

< Manufacturing example 7> Preparation of compound 79

Compound 3-1 5g (12.8 mmol), Compound 9-phenyl-9H,9'H-3,3'-biscarbazole 5.27g (12.9 mmol), CuI 2.45g (12.9 mmol), K ₃ PO ₄ 5.48g (25.8mmol), 1.5mL (12.9mmol) of 1,2-cyclohexanediamine, and 50mL of 1,4-dioxane were added, followed by nitrogen substitution. The reaction was performed under reflux for 12 hours, and extraction was performed using distilled water, MC and NaCl. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed by a rotary evaporator, and then purified by column chromatography using MC:ethyl acetate=1:1 to obtain 6.5g (70%) of the title compound 79 .

< Manufacturing example 8> Preparation of compound 83

Compound 3-1 5g(12.8mmol), Compound 5H-benzo[4,5]thieno[3,2-c]carbazole 3.49g(12.8mmol), CuI 2.45g(12.8mmol), K ₃ PO ₄ 5.48 g (25.8 mmol), trans-1,2-diaminocyclohexane 1.5 mL (12.8 mmol), and 1,4-dioxane 50 mL were added, followed by nitrogen substitution. The reaction was performed under reflux for 12 hours, and extraction was performed using distilled water, MC and NaCl. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed by a rotary evaporator, and then purified by column chromatography using MC:ethyl acetate=1:1 to obtain 6g (80%) of the title compound 83 .

< Manufacturing example 9> Preparation of compound 148

Compound 4-1 8 g (20.4 mmol), Compound 7,7-dimethyl-5,7-dihydroindeto [2,1-b] carbazole 5.79 g (20.4 mmol), CuI 3.84 g (20.4 mmol) ), K ₃ PO ₄ 8.56 g (40.3 mmol), trans-1,2-diaminocyclohexane 2.42 mL (20.4 mmol), and 1,4-dioxane 70 mL were added, followed by nitrogen substitution. The reaction was performed under reflux for 12 hours, and extraction was performed using distilled water, MC and NaCl. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed by a rotary evaporator, and then purified by column chromatography using MC:ethyl acetate=1:1 to obtain 5.35 g (44%) of the title compound 148 .

< Manufacturing example 10> Preparation of compound 206

1) Preparation of compound 10-2

2-bromodibenzo[b,d]thiophene 5.0g(19.0mmol), 7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole 4.5g(15.8mmol) , CuI 3.0g (15.8 mmol), trans-1,2-diaminocyclohexane 1.9 mL (15.8 mmol) and K ₃ PO ₄ 3.3 g (31.6 mmol) dissolved in 100 mL of 1,4-oxane 24 Refluxed for time. After the reaction was completed, distilled water and DCM were added and extracted at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed with a rotary evaporator. The reaction was purified by column chromatography (DCM:Hex=1:3) and recrystallized with methanol to obtain 7.3 g (85%) of the target compound 10-2.

2) Preparation of compound 10-1

To a mixed solution containing 6.7 g (14.3 mmol) of compound 10-2 and 100 mL of THF was added dropwise to 7.4 mL (18.6 mmol) of 2.5M n-BuLi at -78°C, and stirred at room temperature for 1 hour. Trimethyl borate (B(OMe) ₃ ) 4.8 mL (42.9 mmol) was added dropwise to the reaction mixture, followed by stirring at room temperature for 2 hours. After the reaction was completed, distilled water and DCM were added and extracted at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed with a rotary evaporator. The reaction was purified by column chromatography (DCM:MeOH=100:3) and recrystallized with DCM to obtain 5.1 g (70%) of the target compound 8-1.

3) Preparation of compound 206

Compound 10-1 9.7 g (19.0 mmol), compound 5-1 5.1 g (19.0 mmol), Pd (PPh ₃ ) ₄ 1.1 g (0.95 mmol) and K ₂ CO ₃ 5.2 g (38.0 mmol) After dissolving in toluene/EtOH/H ₂ O 100/20/20mL, it was refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added and extracted at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed with a rotary evaporator. The reaction was purified by column chromatography (DCM:Hex=1:3) and recrystallized with methanol to obtain 9.3 g (70%) of the target compound 206.

A compound was prepared in the same manner as in Preparation Examples, and the results of the synthesis confirmation are shown in Tables 1 to 12 below.

[Table 1]

[Table 2]

[Table 3]

[Table 4]

[Table 5]

[Table 6]

[Table 7]

[Table 8]

[Table 9]

[Table 10]

[Table 11]

[Table 12]

Table 11 shows the NMR values, and Table 12 shows the molecular weights of compounds 8, 9, 19, 21, 23, 29, 79, 83 and 148.

4 shows the LC/MS measurement results of Compound 8.

5 shows the LC/MS measurement results of Compound 9.

6 shows the LC/MS measurement results of Compound 19.

7 shows the LC/MS measurement result of Compound 21.

8 shows the LC/MS measurement results of Compound 23.

9 shows the LC/MS measurement results of Compound 29.

10 shows the LC/MS measurement results of Compound 79.

11 shows the LC/MS measurement result of Compound 83.

12 shows the LC/MS measurement results of Compound 148.

LC/MS was measured using Agilent's 6530 Accurate-Mass Q-TOF LC/MS equipment. In more detail, 1 mg of each of the compounds 8, 9, 19, 21, 23, 29, 79, 83 and 148 was dissolved in 1 mL of THF, and the target molecular weight was confirmed using the above equipment. When 1 is added to the molecular weight measured by the equipment, it is the actual molecular weight, and by looking at the results, it was confirmed that the target compound was properly synthesized.

< Experimental example >

1) Fabrication of organic light emitting device

A glass substrate coated with a thin film of ITO to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as acetone, methanol, and isopropyl alcohol, dried, and UVO treated for 5 minutes using UV in a UV scrubber. After the substrate was transferred 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 the thermal evaporation equipment for organic deposition.

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

The light emitting layer was thermally vacuum deposited thereon as follows. The light-emitting layer was formed by doping 7% of a phosphorescent dopant on the host using the compound described in the following table as a host and a green phosphorescent dopant, Ir(ppy) ₃ (tris(2-phenylpyridine)iridium). After that, 60Å of BCP was deposited as a hole blocking layer, and Alq ₃ as an electron transport layer thereon. Was deposited at 200 Å.

Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1200 Å to form a cathode. A light emitting device was manufactured.

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

2) organic Electric field Driving voltage and luminous efficiency of light-emitting elements

For the organic electroluminescent device manufactured as described above, electroluminescence (EL) characteristics were measured with the M7000 of McScience, and the reference luminance was 6,000 through the life equipment measuring equipment (M6000) manufactured by McScience. When cd/m ² , T ₉₀ was measured. The characteristics of the organic electroluminescent device of the present invention are shown in Table 13 below.

[Table 13]

As can be seen from the results of Table 13, the organic electroluminescent device using the organic electroluminescent device emitting layer material of the present invention has a lower driving voltage, improved luminous efficiency, and significantly improved lifespan compared to Comparative Example 1.

Claims (11)

Heterocyclic compound represented by the following Formula 1:
[Formula 1]

In Formula 1,
X1 is S or O,
At least one of Y1 to Y4 is N, the rest are N or CR6,
R1 is represented by -(L)p-(Y)q,
R2 to R6 are hydrogen,
L is a direct bond; C ₆ to C ₆₀ arylene group; Or a C ₂ to C ₆₀ heteroarylene group,
Y is a substituted or unsubstituted C ₆ to C ₆₀ aryl group; A substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R";-P(=O)RR'; and C ₆ to C ₆₀ selected from the group consisting of an amine group substituted or unsubstituted with an aryl group,
p is 0 to 10, q is 1 to 10,
R, R'and R" are the same as or different from each other, and each independently a substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl group,
The "substituted or unsubstituted" means deuterium, a halogen group, -CN, a C ₁ to C ₂₀ linear alkyl group, a C ₃ to C ₂₀ branched alkyl group, a C ₆ to C ₆₀ aryl group, and C ₂ to Substituted or unsubstituted with one or more substituents selected from the group consisting of C ₆₀ heteroaryl groups, substituted or unsubstituted with a substituent to which two or more of the substituents are bonded, or substituted or unsubstituted with a substituent to which two or more substituents selected from the above substituents are connected It means bright. The method according to claim 1, wherein the formula 1 is a heterocyclic compound, characterized in that represented by any one of the following formulas 2 to 9:
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

In Formulas 2 to 9,
R1 is the same as the definition in Formula 1. delete The method according to claim 1, wherein Y in Formula 1 is a substituted or unsubstituted C ₆ to C ₆₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,
The "substituted or unsubstituted" means deuterium, a halogen group, -CN, a C ₁ to C ₂₀ linear alkyl group, a C ₃ to C ₂₀ branched alkyl group, a C ₆ to C ₆₀ aryl group, and C ₂ to Substituted or unsubstituted with one or more substituents selected from the group consisting of C ₆₀ heteroaryl groups, substituted or unsubstituted with a substituent to which two or more of the substituents are bonded, or substituted or unsubstituted with a substituent to which two or more substituents selected from the above substituents are connected A heterocyclic compound that means cyclic. The method of claim 1, wherein Y is

And, X3 and X4 are substituted or unsubstituted C ₆ to C ₆₀ aromatic hydrocarbon rings; Or a substituted or unsubstituted C ₂ to C ₆₀ aromatic hetero ring,
The "substituted or unsubstituted" means deuterium, a halogen group, -CN, a C ₁ to C ₂₀ linear alkyl group, a C ₃ to C ₂₀ branched alkyl group, a C ₆ to C ₆₀ aryl group, and C ₂ to Substituted or unsubstituted with one or more substituents selected from the group consisting of C ₆₀ heteroaryl groups, substituted or unsubstituted with a substituent to which two or more of the substituents are bonded, or substituted or unsubstituted with a substituent to which two or more substituents selected from the above substituents are connected A heterocyclic compound that means cyclic. The method of claim 5, wherein

Is a heterocyclic compound represented by any one of the following structural formulas:

In the above structural formulas, Z ₁ to Z ₃ are the same as or different from each other, and each independently S or O,
Z ₄ to Z ₁₀ are the same as or different from each other, and each independently CR'R",NR', S or O,
R′ and R” are the same as or different from each other, and each independently hydrogen; substituted or unsubstituted C ₁ to C ₆₀ alkyl; or substituted or unsubstituted C ₆ to C ₆₀ aryl,
The "substituted or unsubstituted" means deuterium, a halogen group, -CN, a C ₁ to C ₂₀ linear alkyl group, a C ₃ to C ₂₀ branched alkyl group, a C ₆ to C ₆₀ aryl group, and C ₂ to Substituted or unsubstituted with one or more substituents selected from the group consisting of C ₆₀ heteroaryl groups, substituted or unsubstituted with a substituent to which two or more of the substituents are bonded, or substituted or unsubstituted with a substituent to which two or more substituents selected from the above substituents are connected It means bright. The heterocyclic compound of claim 1, wherein the formula 1 is represented by any one of the following compounds:

Organic light emission comprising an anode, a cathode, and at least one organic material layer provided between the anode and the cathode, and at least one of the organic material layers includes the heterocyclic compound according to any one of claims 1, 2, and 4 to 7 device. The method according to claim 8, wherein the organic material layer comprises at least one of a hole blocking layer, an electron injection layer, and an electron transport layer, and at least one of the hole blocking layer, the electron injection layer and the electron transport layer includes the heterocyclic compound. An organic light-emitting device, characterized in that. The organic light-emitting device of claim 8, wherein the organic material layer includes an emission layer, and the emission layer includes the heterocyclic compound. The method according to claim 8, wherein the organic material layer comprises at least one layer of a hole injection layer, a hole transport layer, and a layer that simultaneously injects and transports holes, and one of the layers includes the heterocyclic compound. Organic light emitting device.

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