KR102280866B1 - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a heterocyclic compound of Formula 1 and an organic light emitting device including the same.

Description

Heterocyclic compound and organic light emitting device comprising the same {HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2018-000024543 filed with the Korean Intellectual Property Office on February 28, 2018, the entire contents of which are incorporated herein by reference.

The present specification relates to a heterocyclic compound, and an organic light emitting device formed using the heterocyclic compound.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and these excitons are When it falls back to the ground state, it lights up.

The development of new materials for the organic light emitting device as described above is continuously required.

US Patent Application Publication No. 2004-0251816

The present specification provides a heterocyclic compound and an organic light emitting device including the same.

According to an exemplary embodiment of the present specification, there is provided a heterocyclic compound represented by the following Chemical Formula 1.

[Formula 1]

In Formula 1 above

이고, Q is

ego,

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

At least one of X1 to X3 is N,

R and R1 to R4 are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, A substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents may combine with each other to form a substituted or unsubstituted ring,

L1 is a direct bond, or a substituted or unsubstituted arylene group,

A1 and A2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

a and b are each an integer of 0 to 5, and when a and b are each 2 or more, R1 is the same as or different from each other, R2 is the same as or different from each other,

c is an integer from 0 to 3, and when c is 2 or more, R3 are the same as or different from each other,

d is an integer from 0 to 8, and when d is 2 or more, R4 is the same as or different from each other.

In addition, the present specification is a first electrode; 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 includes the heterocyclic compound.

The heterocyclic compound according to an exemplary embodiment of the present specification may be used as a material for an organic material layer of an organic light emitting device, and by using the same, it is possible to improve efficiency, low driving voltage and/or lifespan characteristics in an organic light emitting device.

1 illustrates an organic light emitting diode according to an exemplary embodiment of the present specification.
2 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.

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

The present specification provides a heterocyclic compound represented by Formula 1 above.

The present specification provides a compound characterized in that the N-containing heterocyclic ring and the condensed ring core are bonded.

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

Examples of substituents in the present specification are described below, but are not limited thereto.

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, and the like.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are limited thereto it is not

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

In the present specification, the phosphine oxide group specifically includes, but is not limited to, a diphenylphosphine oxide group, a dinaphthyl phosphine oxide, and the like.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a phenalenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc., but is not limited thereto no.

In the present specification, the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.

,

,

,

,

및

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

,

,

,

,

and

etc. can be However, the present invention is not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, a triazinyl group Jolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, pe Nonthrolinyl group (phenanthroline), isoxazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are not limited thereto.

In the present specification, the arylene group is the same as the definition of the aryl group, except that it is divalent.

In the present specification, the heteroarylene group is the same as the definition of the heteroaryl group, except that it is divalent.

In the present specification, Q is any one of 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, R4 and d are as defined in Formula 1,

The dotted line is a site binding to the core of Formula 1 above.

In the present specification, Chemical Formula 1 is represented by Chemical Formula 2 below.

[Formula 2]

In Formula 2, R1 to R4, X1 to X3, A1, A2, L1, and a to d are the same as defined in Formula 1 above.

In the present specification, X1 to X3 are N.

In the present specification, X1 and X2 are N, and X3 is CR.

In the present specification, X1 and X3 are N, and X2 is CR.

In the present specification, X2 and X3 are N, and X1 is CR.

In the present specification, L1 is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In the present specification, L1 is a direct bond, or an arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.

In the present specification, L1 is a direct bond, or a monocyclic arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.

In the present specification, L1 is a direct bond, or a polycyclic arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.

In the present specification, L1 is a direct bond, a phenylene group, a biphenylene group, a terphenylene group, a quarterphenylene group, a naphthylene group, a phenanthrenylene group, a dimethylfluorenylene group, a pyrenylene group, a triphenylene group, or It is an anthracenylene group.

In the present specification, L1 is a direct bond, a phenylene group, a biphenylrylene group, a naphthylene group, or an anthracenylene group.

In the present specification, L1 is any one of the following substituents.

The dotted line is a portion bonded to the core and the N-containing monocyclic ring.

In the present specification, L1 is a direct bond.

In the present specification, L1 is a phenylene group.

In the present specification, L1 is a biphenylrylene group.

In the present specification, L1 is a naphthylene group.

In the present specification, L1 is an anthracenylene group.

According to an exemplary embodiment of the present specification, R1 to R4 and R are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, Or a substituted or unsubstituted heteroaryl group, or adjacent substituents may combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, R1 to R4 and R are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted A cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, the R1 to R4 and R are hydrogen.

According to an exemplary embodiment of the present specification, A1 and A2 are the same as each other, and are a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, A1 and A2 are the same as each other and are substituted or unsubstituted aryl groups.

According to an exemplary embodiment of the present specification, A1 and A2 are the same as each other and are a heteroaryl group including any one or more of substituted or unsubstituted N, O, and S.

According to an exemplary embodiment of the present specification, A1 and A2 are different from each other and each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, A1 and A2 are different from each other and each independently represent a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, A1 and A2 are different from each other and each independently represent a heteroaryl group including at least one of substituted or unsubstituted N, O, and S.

According to an exemplary embodiment of the present specification, A1 is a substituted or unsubstituted aryl group, and A2 is a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, A2 is a substituted or unsubstituted aryl group, and A1 is a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently any one of a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted N, O, and S It is a heteroaryl group having 3 to 20 carbon atoms including one or more,

The substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms including any one or more of substituted or unsubstituted N, O, and S is deuterium, a nitrile group, a halogen group, an alkyl group , an aryl group, or may be unsubstituted or substituted with a heteroaryl group including any one or more of N, O, and S.

According to an exemplary embodiment of the present specification, A1 and A2 are the same as each other, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted N, O, and S carbon number including any one or more It is a heteroaryl group of 3 to 20,

The substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms including any one or more of substituted or unsubstituted N, O, and S is deuterium, a nitrile group, a halogen group, an alkyl group , an aryl group, or may be unsubstituted or substituted with a heteroaryl group including any one or more of N, O, and S.

According to an exemplary embodiment of the present specification, A1 and A2 are different from each other, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted carbon number including any one or more of N, O, and S It is a heteroaryl group of 3 to 20,

The substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms including any one or more of substituted or unsubstituted N, O, and S is deuterium, a nitrile group, a halogen group, an alkyl group , an aryl group, or may be unsubstituted or substituted with a heteroaryl group including any one or more of N, O, and S.

In the present specification, A1 and A2 are the same as each other, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted N, O, and S having 3 to 20 carbon atoms including any one or more It may be selected from the group consisting of a heteroaryl group,

The substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and the heteroaryl group having 3 to 20 carbon atoms including any one or more of substituted or unsubstituted N, O, and S are deuterium, a nitrile group, a halogen group, a carbon number It may be unsubstituted or substituted with a 1 to 10 alkyl group, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms including any one or more of N, O, and S.

In the present specification, A1 and A2 are the same as each other, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted N, O, and S having 3 to 20 carbon atoms including any one or more It may be selected from the group consisting of a heteroaryl group,

The substituted or unsubstituted C 6 to C 30 aryl group, and the substituted or unsubstituted C 3 to C 20 heteroaryl group including any one or more of N, O, and S are deuterium, a nitrile group, a methyl group, terbutyl a phenyl group unsubstituted or substituted with a phenyl group, a trimethylsilyl group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, an anthracene group, a naphthyl group, a triphenylene group, or a dimethylfluorene group; a biphenyl group unsubstituted or substituted with a nitrile group; terphenyl group; naphthyl group; anthracene group; phenanthrene group; triphenylene group; a fluorene group unsubstituted or substituted with a methyl group or a phenyl group; spirobifluorene group; pyridine group; a carbazole group unsubstituted or substituted with a phenyl group; a dibenzofuran group unsubstituted or substituted with a phenyl group; a dibenzothiophene group substituted or unsubstituted with a phenyl group; benzonaphthofuran group; or a benzonaphthothiophene group.

In the present specification, A1 and A2 are the same as or different from each other and each independently a deuterium, a methyl group, a nitrile group, a terbutyl group, a phenyl group, a trimethylsilyl group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, an anthracene a phenyl group unsubstituted or substituted with a group, a naphthyl group, a triphenylene group, or a dimethylfluorene group; a biphenyl group unsubstituted or substituted with a nitrile group; terphenyl group; naphthyl group; anthracene group; phenanthrene group; triphenylene group; dimethyl fluorene group; diphenylfluorene group; spirobifluorene group; pyridine group; pyrimidine group; triazine group; a carbazole group unsubstituted or substituted with a phenyl group; a dibenzofuran group unsubstituted or substituted with a phenyl group; a dibenzothiophene group substituted or unsubstituted with a phenyl group; benzonaphthofuran group; or a benzonaphthothiophene group.

In the present specification, A1 and A2 are the same as each other and deuterium, methyl group, nitrile group, terbutyl group, phenyl group, trimethylsilyl group, dibenzothiophene group, dibenzofuran group, carbazole group, anthracene group, naphthyl group, tri a phenyl group unsubstituted or substituted with a phenylene group or a dimethylfluorene group; a biphenyl group unsubstituted or substituted with a nitrile group; terphenyl group; naphthyl group; anthracene group; phenanthrene group; triphenylene group; dimethyl fluorene group; diphenylfluorene group; spirobifluorene group; pyridine group; pyrimidine group; triazine group; a carbazole group unsubstituted or substituted with a phenyl group; a dibenzofuran group unsubstituted or substituted with a phenyl group; a dibenzothiophene group substituted or unsubstituted with a phenyl group; benzonaphthofuran group; or a benzonaphthothiophene group.

In the present specification, A1 and A2 are different from each other and each independently a deuterium, a methyl group, a nitrile group, a terbutyl group, a phenyl group, a trimethylsilyl group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, an anthracene group, a phenyl group unsubstituted or substituted with a naphthyl group, a triphenylene group, or a dimethylfluorene group; a biphenyl group unsubstituted or substituted with a nitrile group; terphenyl group; naphthyl group; anthracene group; phenanthrene group; triphenylene group; dimethyl fluorene group; diphenylfluorene group; spirobifluorene group; pyridine group; pyrimidine group; triazine group; a carbazole group unsubstituted or substituted with a phenyl group; a dibenzofuran group unsubstituted or substituted with a phenyl group; a dibenzothiophene group substituted or unsubstituted with a phenyl group; benzonaphthofuran group; or a benzonaphthothiophene group.

In the present specification, A1 and A2 are the same as or different from each other and each independently represent a phenyl group unsubstituted or substituted with deuterium, a methyl group, a terbutyl group, a phenyl group, a trimethylsilyl group, or a nitrile group; a biphenyl group substituted or unsubstituted with a nitrile group; naphthyl group; phenanthrene group; dimethyl fluorene group; diphenylfluorene group; pyridine group; a carbazole group unsubstituted or substituted with a phenyl group; a dibenzofuran group unsubstituted or substituted with a phenyl group; or a dibenzothiophene group unsubstituted or substituted with a phenyl group.

In the present specification, A1 and A2 are the same as or different from each other and each independently represent a phenyl group unsubstituted or substituted with deuterium, a methyl group, a terbutyl group, a phenyl group, a trimethylsilyl group, or a nitrile group; a biphenyl group substituted or unsubstituted with a nitrile group; naphthyl group; a fluorene group unsubstituted or substituted with a methyl group or a phenyl group; pyridine group; a carbazole group unsubstituted or substituted with a phenyl group; a dibenzofuran group unsubstituted or substituted with a phenyl group; Or a dibenzothiophene group unsubstituted or substituted with a phenyl group; phenanthrene group; or a terphenyl group.

In the present specification, A1 and A2 may be the same as or different from each other and may each independently represent any one of the following substituents.

는 코어와 연결되는 부위이다.in the above substituent

is the part that connects to the core.

According to another exemplary embodiment of the present specification, the heterocyclic compound of Formula 1 may be represented by any one selected from the following structural formulas.

According to an exemplary embodiment of the present specification, the heterocyclic compound of Formula 1 may be prepared according to the following reaction scheme, but is not limited thereto. In the following reaction scheme, various types of intermediates can be synthesized according to the appropriate selection of known starting materials by those skilled in the art for the type and number of substituents. As the reaction type and reaction conditions, those known in the art may be used.

In the above reaction scheme, X1 to X3, L, A1 and A2 are as defined in Formula 1 above.

All of the heterocyclic compounds of Formula 1 described herein can be prepared by appropriately combining the preparation formulas described in the Examples of the present specification and the intermediates based on common technical knowledge.

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

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 addition, the organic layer may include at least one of an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons, and at least one of the layers may include the compound.

In the organic light emitting device of the present invention, a first electrode, an organic material layer, and a second electrode are sequentially stacked on a substrate.

In the organic light emitting device of the present invention, a first electrode, a light emitting layer, a hole blocking layer, and a second electrode are sequentially stacked on a substrate.

In the organic light emitting device of the present invention, a first electrode, a hole transport layer, a light emitting layer, a hole blocking layer, and a second electrode are sequentially stacked on a substrate.

In the organic light emitting device of the present invention, a first electrode, a light emitting layer, a hole blocking layer, an electron injection and transport layer, and a second electrode are sequentially stacked on a substrate.

In the organic light emitting device of the present invention, a first electrode, a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron injection and transport layer, and a second electrode are sequentially stacked on a substrate.

In the organic light emitting device of the present invention, a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron injection and transport layer, and a second electrode are sequentially stacked on a substrate.

1 illustrates a structure of an organic light emitting device in which a first electrode 2 , an organic material layer 3 , and a second electrode 4 are sequentially stacked on a substrate 1 .

2 shows a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 8, a hole blocking layer 9, an electron injection and The structure of the organic light emitting device in which the transport layer 10 and the second electrode 4 are sequentially stacked is illustrated.

1 and 2 illustrate an organic light emitting device, but is not limited thereto.

In an exemplary embodiment of the present invention, the organic material layer may include a light emitting layer, and the heterocyclic compound of Formula 1 may be included in the light emitting layer.

In an exemplary embodiment of the present invention, the organic material layer includes a hole injection layer, a hole transport layer or an electron blocking layer, and the hole injection layer, the hole transport layer or the electron blocking layer may include a heterocyclic compound of Formula 1 .

In an exemplary embodiment of the present invention, the organic material layer includes an electron injection layer, an electron transport layer or a hole blocking layer, and the electron injection layer, the electron transport layer or the hole blocking layer may include the heterocyclic compound of Formula 1 above. .

In an exemplary embodiment of the present invention, the organic material layer may include a hole blocking layer, and the hole blocking layer may include the heterocyclic compound of Formula 1 above.

For example, the organic light emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal or a conductive metal oxide or an alloy thereof on a substrate. to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an organic material layer including the heterocyclic compound of Formula 1 thereon, a material that can be used as a cathode thereon It can be prepared by vapor deposition. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

As the anode material, a material having a large work function is generally preferable to facilitate hole injection into the organic material layer. Specific examples of the anode material that can be used in the present invention 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 : a combination of a metal such as Sb and an oxide; poly(3-methyl compound), poly[3,4-(ethylene-1,2-dioxy) compound] (PEDT), polypyrrole and conductive polymers such as polyaniline, and the like, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. 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; and a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, and conductive polymers based on polyaniline and polycompounds, but is not limited thereto.

As the hole transport material, a material capable of transporting holes from an anode or a hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic compounds include heterocyclic compounds, dibenzofuran derivatives, ladder type compounds. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer is formed using the heterocyclic compound.

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. and forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The present specification also provides a method of manufacturing an organic light emitting device formed using the heterocyclic compound.

Specifically, in one embodiment of the present specification, preparing a substrate; forming a cathode or an anode on the substrate; forming one or more organic material layers on the cathode or anode; and forming an anode or a cathode on the organic material layer, wherein at least one layer of the organic material layer is formed using the heterocyclic compound.

Examples of the dopant material include an aromatic heterocyclic compound, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic heterocyclic compound is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene, and the like, having an arylamino group. As the styrylamine compound, a substituted or unsubstituted A compound in which at least one arylvinyl group is substituted with a cyclic arylamine, wherein one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. As an electron transport material, a material that can receive electrons from the cathode and transfer them to the light emitting layer is suitable. do. Specific examples include Al complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer A compound which prevents movement to a layer and is excellent in the ability to form a thin film is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. It is not limited to this.

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

A method of preparing the heterocyclic compound of Formula 1 and manufacturing an organic light emitting device using the same will be described in detail in Examples below. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

Preparation Example 1

Compound A (7.50 g, 15.12 mmol) and compound a1 (5.87 g, 16.63 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (120 mL) was added. , tetrakis-(triphenylphosphine)palladium (0.52 g, 0.45 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220 mL of ethyl acetate to prepare Compound 1 (7.56 g, 69%).

MS[M+H] ⁺ = 726

Preparation 2

Compound A (7.50 g, 15.12 mmol) and compound a2 (5.87 g, 16.63 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (120 mL) was added. , tetrakis-(triphenylphosphine)palladium (0.52 g, 0.45 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220 mL of ethyl acetate to prepare Compound 2 (6.82 g, 62%).

MS[M+H] ⁺ = 726

Preparation 3

Compound A (7.50 g, 15.12 mmol) and compound a3 (5.87 g, 16.63 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (120 mL) was added. , tetrakis-(triphenylphosphine)palladium (0.52 g, 0.45 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220 mL of ethyl acetate to prepare compound 3 (6.28 g, 57%).

MS[M+H] ⁺ = 725

Preparation 4

Compound A (7.50 g, 15.12 mmol) and compound a4 (7.14 g, 16.63 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (120 mL) was added. , tetrakis-(triphenylphosphine)palladium (0.52 g, 0.45 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from tetrahydrofuran 220 mL to prepare compound 4 (9.54 g, 79%).

MS[M+H] ⁺ = 802

Preparation 5

Compound A-1 (10.01 g, 18.44 mmol) and compound a5 (5.50 g, 16.03 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added. After addition, tetrakis-(triphenylphosphine)palladium (0.56 g, 0.48 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 310 mL of ethyl acetate to prepare compound 5 (8.82 g, 76%).

MS[M+H] ⁺ = 726

Preparation 6

Compound A-1 (9.33 g, 17.19 mmol) and compound a6 (5.50 g, 14.95 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added. After addition, tetrakis-(triphenylphosphine)palladium (0.52 g, 0.45 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 210 mL of ethyl acetate to prepare compound 6 (5.49 g, 49%).

MS[M+H] ⁺ = 751

Preparation 7

Compound A-1 (9.33 g, 17.19 mmol) and compound a7 (5.50 g, 14.95 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (120 mL) was added. After addition, tetrakis-(triphenylphosphine)palladium (0.52 g, 0.45 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 210 mL of ethyl acetate to prepare compound 7 (5.49 g, 49%).

MS[M+H] ⁺ = 751

Preparation 8

Compound B-1 (10.01 g, 18.44 mmol) and compound a5 (5.50 g, 16.03 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added. After addition, tetrakis-(triphenylphosphine)palladium (0.56 g, 0.48 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 230 mL of ethyl acetate to prepare compound 8 (7.12 g, 61%).

MS[M+H] ⁺ = 726

Preparation 9

Compound B (7.50 g, 15.12 mmol) and compound a1 (6.31 g, 17.39 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (120 mL) was added. , tetrakis-(triphenylphosphine)palladium (0.52 g, 0.45 mmol) was added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 230 mL of ethyl acetate to prepare compound 9 (7.12 g, 61%).

MS[M+H] ⁺ = 726

Preparation 10

Compound B (7.50 g, 15.12 mmol) and compound a3 (5.87 g, 16.63 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (120 mL) was added. , tetrakis-(triphenylphosphine)palladium (0.52 g, 0.45 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220 mL of ethyl acetate to prepare compound 10 (5.37 g, 49%).

MS[M+H] ⁺ = 725

Preparation 11

Compound A-1 (13.14 g, 24.16 mmol) and compound a6 (7.50 g, 21.01 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added. After addition, tetrakis-(triphenylphosphine)palladium (0.73 g, 0.63 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 mL of ethyl acetate to prepare compound 11 (10.44 g, 68%).

MS[M+H] ⁺ = 726

Preparation 12

Compound A-1 (12.58 g, 23.12 mmol) and compound a7 (7.50 g, 20.11 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (120 mL) was added. After addition, tetrakis-(triphenylphosphine)palladium (0.70 g, 0.60 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 mL of ethyl acetate to prepare compound 12 (9.36 g, 62%).

MS[M+H] ⁺ = 756

Preparation 13

Compound B-1 (14.80 g, 27.21 mmol) and compound a8 (7.50 g, 23.66 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added. After addition, tetrakis-(triphenylphosphine)palladium (0.82 g, 0.71 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 230 mL of ethyl acetate to prepare compound 13 (10.75 g, 65%).

MS[M+H] ⁺ = 700

Example 1-1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermal vacuum deposition of a compound of the following compound HI1 and a compound of the following compound HI2 to a thickness of 100 Å in a ratio of 98:2 (molar ratio) on the prepared anode, ITO transparent electrode. A hole transport layer was formed by vacuum-depositing a compound (1150 Å) represented by the following formula HT1 on the hole injection layer. Then, a compound of EB1 was vacuum-deposited to a thickness of 50 Å on the hole transport layer to form an electron blocking layer. Then, the compound represented by the following formula BH and the compound represented by the following formula BD to a thickness of 200 Å on the electron blocking layer were vacuum-deposited in a weight ratio of 25:1 to form a light emitting layer. Compound 1 was vacuum-deposited to a film thickness of 50 Å on the light emitting layer to form a hole blocking layer. Then, on the hole blocking layer, the compound represented by the formula ET1 and the compound represented by the formula LiQ were vacuum-deposited in a weight ratio of 1:1 to form an electron injection and transport layer to a thickness of 310 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4~0.7Å/sec, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3Å/sec, and the deposition rate of aluminum was maintained at 2Å/sec, and the vacuum degree during deposition was 2X10 ^-7 ~ By ^{maintaining 5X10 -6} torr, an organic light emitting device was manufactured.

Example 1-2 to Example 1-13

An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1.

Comparative Examples 1-1 to 1-8

An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1. The compounds of HB1 to HB8 used in Table 1 are as follows.

Experimental Example 1

When a current was applied to the organic light emitting diodes prepared in Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 means the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

compound
(hole blocking layer) Voltage
(V@20mA
/cm ² ) efficiency
(cd/A@20mA
/cm ² ) color coordinates
(x,y) T95
(hr) Example 1-1 compound 1 3.52 6.30 (0.140, 0.047) 285 Example 1-2 compound 2 3.54 6.25 (0.141, 0.047) 280 Examples 1-3 compound 3 3.43 6.57 (0.143, 0.047) 290 Examples 1-4 compound 4 3.51 6.28 (0.139, 0.046) 280 Examples 1-5 compound 5 3.55 6.39 (0.140, 0.047) 285 Examples 1-6 compound 6 3.56 6.21 (0.141, 0.047) 275 Examples 1-7 compound 7 3.59 6.25 (0.140, 0.046) 280 Examples 1-8 compound 8 3.58 6.43 (0.139, 0.045) 290 Examples 1-9 compound 9 3.58 6.45 (0.141, 0.046) 285 Examples 1-10 compound 10 3.45 6.54 (0.142, 0.046) 255 Examples 1-11 compound 11 3.57 6.46 (0.140, 0.047) 275 Examples 1-12 compound 12 3.54 6.45 (0.141, 0.045) 280 Examples 1-13 compound 13 3.60 6.47 (0.140, 0.046) 275 Comparative Example 1-1 HB1 4.17 5.71 (0.139, 0.041) 115 Comparative Example 1-2 HB2 3.95 5.93 (0.141, 0.042) 220 Comparative Example 1-3 HB3 4.15 6.03 (0.139, 0.041) 145 Comparative Example 1-4 HB4 3.85 5.95 (0.141, 0.042) 65 Comparative Example 1-5 HB5 4.25 5.68 (0.142, 0.043) 115 Comparative Example 1-6 HB6 3.94 5.82 (0.142, 0.044) 220 Comparative Example 1-7 HB7 4.03 5.93 (0.143, 0.043) 145 Comparative Examples 1-8 HB8 5.11 4.86 (0.143, 0.043) 65

Referring to Table 1, the organic light emitting device using the compound of the present invention as a hole blocking layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.

The compound of Comparative Example 1-1 in which a methyl group is substituted at positions 9 and 10 of the fluorene core of the present invention and in Comparative Examples 1-2 to where triazine and pyridine are connected at positions 2, 3, and 4 of the benzofluorene core It shows characteristics of low voltage, high efficiency and longer life than organic light emitting diodes manufactured using 1-4 as a hole blocking layer.

Whereas Q of the present invention is a phenanthrene group, Comparative Examples 1-5 used a compound in which the part corresponding to Q is benzene. Comparative Examples 1-6 and Comparative Examples 1-7 use a compound in which a methyl group is substituted at the 9th position of the fluorene core, unlike the present invention. Comparative Example 8 used a compound in which only an aryl group was substituted for the core.

The present invention also showed characteristics of low voltage, high efficiency, and long life compared to Comparative Examples 1-5 to 1-8.

As shown in the results of Table 1, it was confirmed that the compound according to the present invention has excellent hole blocking ability and thus can be applied to an organic light emitting device.

Although the preferred embodiment (hole blocking layer) of the present invention has been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and detailed description of the invention, and this belongs to the scope of the invention.

1: substrate
2: first electrode
3: organic layer
4: second electrode
5: hole injection layer
6: hole transport layer
7: Electronic blocking layer
8: light emitting layer
9: hole blocking layer
10: electron injection and transport layer

Claims (8)

A heterocyclic compound represented by the following formula (2):
[Formula 2]

In Formula 2,
X1 to X3 are the same as or different from each other, each independently N or CR,
At least one of X1 to X3 is N,
R and R1 to R4 are the same as or different from each other, and are each independently hydrogen or deuterium;
L1 is a direct bond, a phenylene group, a biphenylrylene group, a naphthylene group or an anthracenylene group,
A1 and A2 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with deuterium, a methyl group, a terbutyl group, a naphthyl group, a trimethylsilyl group, or a nitrile group; a biphenyl group unsubstituted or substituted with a nitrile group; naphthyl group; a fluorene group substituted with a methyl group; pyridine group; a carbazole group substituted with a phenyl group; dibenzofuran group; dibenzothiophene group; phenanthrene group; or a terphenyl group,
a and b are integers of 5, and when a and b are each 2 or more, R1 is the same as or different from each other, R2 is the same as or different from each other,
c is an integer of 3, and when c is 2 or more, R3 are the same as or different from each other,
d is an integer of 8, and when d is 2 or more, R4 is the same as or different from each other. delete delete delete delete The heterocyclic compound according to claim 1, wherein Formula 2 is any one selected from the following structural formulas:

a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the heterocyclic compound of claim 1 or 6 . device. The organic light emitting diode of claim 7, wherein the organic material layer includes a hole blocking layer, and the hole blocking layer includes the heterocyclic compound.

Images