KR20220113279A - Polycyclic compound and organic light emitting device using the same - Google Patents

Abstract

The present invention relates to a polycyclic compound that can be employed in various organic layers provided in an organic light emitting device and a high-efficiency and long-life organic light-emitting device with significantly improved luminous efficiency. The compound is represented by a chemical formula A or a chemical formula B.

Description

Polycyclic compound and organic light emitting device using the same

The present invention relates to a polycyclic compound and a high-efficiency and long-life organic light-emitting device with remarkably improved luminous efficiency using the same.

In an organic light emitting device, an electron injected from an electron injection electrode (cathode electrode) and a hole injected from a hole injection electrode (anode electrode) combine in a light emitting layer to form an exciton, and the exciton generates energy It is a self-luminous device that emits light while emitting light, and such an organic light-emitting device has a low driving voltage, high luminance, wide viewing angle, and fast response speed, and is in the spotlight as a next-generation light source because of its advantages that it can be applied to a full-color flat panel light emitting display. .

In order for such an organic light emitting device to exhibit the above characteristics, the structure of the organic layer in the device is optimized, and the material constituting each organic layer is a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, an electron blocking material. It should be preceded by a stable and efficient material, but there is still a need for a stable and efficient structure of an organic layer for an organic light emitting device and development of each material.

As such, the structure of the device capable of improving the light emitting characteristics of the organic light emitting device and the development of a new material supporting it are continuously required.

Accordingly, an object of the present invention is to provide a compound capable of implementing a high-efficiency and long-life organic light-emitting device by being employed in the organic layer of the device, and a high-efficiency and long-life organic light-emitting device including the same.

In order to solve the above problems, the present invention is represented by the following [Formula A] or [Formula B], and any one selected from the following [Formula G] and [Formula W] in the following [Formula A] and [Formula B], respectively It provides a compound, characterized in that it has at least one structure of.

[Formula A]

[Formula B]

[Structural formula G] [Structural formula W]

The [Formula A], [Formula B], [Structural Formula G] and [Structural Formula W] and specific compounds implemented accordingly, Q ₁ To Q ₅ Ring, X, Y ₁ To Y ₃ , G ₁ And G ₂ The definition will be described later.

In addition, the present invention includes a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer is [Formula A] or [Formula B] It provides an organic light emitting device comprising at least one compound represented by.

The polycyclic cyclic compound according to the present invention can be employed in the organic layer in the device to realize a high efficiency and long-life organic light emitting device.

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

The present invention is included in an organic light emitting device, is represented by the following [Formula A] or [Formula B], and has at least one structure selected from the following [Structural Formula G] and [Structural Formula W] It is characterized in that it is possible to implement a high-efficiency and long-life organic light emitting device through this.

[Formula A]

[Formula B]

In the [Formula A] and [Formula B],

Q ₁ to Q ₃ are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 50 carbon atoms, and a substituted or unsubstituted carbon number 3 to 30 aliphatic aromatic mixed rings.

X is selected from B, N, CR ₁ , SiR ₂ , P, P=O and P=S.

Y ₁ to Y ₃ are the same as or different from each other, and each independently represent a divalent group selected from structural formulas represented by the following (Y-1) to (Y-11).

In (Y-1) to (Y-11), R ₁ to R ₁₃ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted A alkenyl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted A cyclic cycloalkenyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 1 to 50 carbon atoms group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon number 2 to 30 heteroaryloxy group, substituted or unsubstituted C 1 to C 30 alkylthio group, substituted or unsubstituted C 6 to C 30 arylthio group, substituted or unsubstituted C 3 to C 30 cycloalkylthi a group, a substituted or unsubstituted C2 to C30 heteroarylthio group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a nitro group, a cyano group, a halogen group, and a substituted or unsubstituted C3 to C3 group 30 aliphatic aromatic mixed ring groups.

According to an embodiment of the present invention, R ₁ to R ₁₃ are a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C3-C30 alkyl group, of a cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 50 carbon atoms, and a substituted or unsubstituted It is selected from an aliphatic aromatic mixed ring group having 3 to 30 carbon atoms.

The [Formula A] or [Formula B] according to the present invention is characterized in that it has at least one structure selected from the following [Structural Formula G] and [Structural Formula W], respectively.

According to an embodiment of the present invention, the [Formula A] or [Formula B] may have the [Structural Formula G] and [Structural Formula W] at the same time, respectively.

[Structural formula G] [Structural formula W]

In the [Structural Formula G] and [Structural Formula W],

Q ₄ to Q ₅ is each independently the same as the definitions of Q ₁ to Q ₃ above.

G ₁ is each independently CR ₁₄ R ₁₅ or SiR ₁₆ R ₁₇ , and G ₂ is each independently selected from CR ₁₈ R ₁₉ , SiR ₂₀ R ₂₁ , NR ₂₂ , O, S, Se and BR ₂₃ .

Each of R ₁₄ to R ₂₃ is the same as defined for R ₁ to R ₁₃ .

* in [Formula G] means a site condensed to the ring of Q ₁ to Q ₃ in any one of [Formula A] and [Formula B].

When the [Structural Formula W] is connected to any one of the [Formula A] and [Formula B], it may be connected to Q ₄ , Q ₅ , G ₁ or G ₂ .

The R ₁ to R ₂₃ , Q ₁ to Q ₅ , G ₁ , G ₂ and a substituent thereof may combine with an adjacent substituent to form a substituted or unsubstituted ring.

According to an embodiment of the present invention, the [Formula A] and [Formula B] according to the present invention may have a structure in which at least one of Q ₁ to Q ₃ is condensed with [Formula G].

In addition, [Formula A] and [Formula B] according to the present invention may be a substituted structure in which one or more of each of Y _One to Y ₂ and Q _One to Q ₃ is connected to the [Structural Formula W].

In addition, Q ₁ and Q ₂ in [Formula A] according to the present invention may be connected to each other to form a substituted or unsubstituted aliphatic ring, an aromatic ring or an aliphatic aromatic mixed ring containing a hydrocarbon or a hetero atom.

As such, the characteristic structures of [Formula A] and [Formula B] according to the present invention implemented according to the above definition and the structure forming the ring can be confirmed in specific compounds to be described later.

According to an embodiment of the present invention, the [Formula A] and [Formula B] are each of the following [Formula A-1] to [Formula A-6] and [Formula B-1] to [Formula B-6] It may be any one selected.

[Formula A-1] [Formula A-2]

[Formula A-3] [Formula A-4]

[Formula A-5] [Formula A-6]

[Formula B-1] [Formula B-2]

[Formula B-3] [Formula B-4]

[Formula B-5] [Formula B-6]

In the [Formula A-1] to [Formula A-6] and [Formula B-1] to [Formula B-6],

Z is CR or N, wherein R is the same as defined for each of R ₁ to R ₁₃ , and a plurality of Z and R are the same as or different from each other.

The plurality of R may be bonded to each other or connected to adjacent substituents to form an alicyclic, aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic, aromatic monocyclic or polycyclic ring may be selected from among N, S and O It may be substituted with any one or more selected heteroatoms.

X, Y ₁ to Y ₃ , G ₁ and G ₂ are the same as defined in [Formula A] and [Formula B], respectively.

On the other hand, in the present invention, the term 'substituted or unsubstituted' refers to Q ₁ to Q ₅ rings, R, R ₁ to R ₂₃ , etc., respectively, deuterium, cyano group, halogen group, hydroxyl group, nitro group, amino group, alkyl group, cyclo Alkyl group, halogenated alkyl group, deuterated alkyl group, alkenyl group, cycloalkenyl group, alkynyl group, heteroalkyl group, heterocycloalkyl group, cycloalkyloxy group, aryl group, arylalkyl group, heteroaryl group, heteroarylalkyl group, alkoxy group, A substituent group substituted with one or two or more substituents selected from the group consisting of an amine group, a silyl group, an aryloxy group, a heteroaryloxy group, a cycloalkylthio group, an alkylthio group, an arylthio group, etc., or a substituent to which two or more of the substituents are connected It means that it is substituted with, or does not have any substituents.

In addition, the carbon number range of the alkyl group or aryl group in the 'substituted or unsubstituted alkyl group having 1 to 30 carbon atoms', 'substituted or unsubstituted aryl group having 6 to 50 carbon atoms', etc., considers the portion in which the substituent is substituted. It refers to the total number of carbon atoms constituting the alkyl part or the aryl part when viewed as unsubstituted. For example, a phenyl group substituted with a butyl group at the para position corresponds to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

In addition, in the present invention, the meaning that adjacent groups are bonded to each other to form a ring means that adjacent groups can be bonded to each other to form a substituted or unsubstituted alicyclic or aromatic ring, and 'adjacent substituents' The substituent may refer to a substituent substituted on an atom directly connected to the substituted atom, a substituent sterically closest to the substituent, or another substituent substituted for the atom in which the substituent is substituted. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as 'adjacent substituents'.

In the present invention, the alkyl group may be linear or branched, and specific examples include a methyl group, an ethyl group, a propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1- Methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group , cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1 -ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, etc., but are not limited thereto.

In the present invention, the alkenyl group includes a straight or branched chain, and may be further substituted by other substituents, specifically, a vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-bute Nyl 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) a vinyl-1-yl group, a stilbenyl group, a styrenyl group, and the like, but are not limited thereto.

In the present invention, the alkynyl group also includes a straight or branched chain, and may be further substituted by other substituents, and may include ethynyl, 2-propynyl, and the like, but is limited thereto. it doesn't happen

In the present invention, the cycloalkyl group is not particularly limited, but specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, spirodecyl, spirodecyl group , adamantyl, etc., but are not limited thereto, and may be further substituted by other substituents, and polycyclic refers to a group in which a cycloalkyl group is directly connected or condensed with another ring group, and the other ring group may be a cycloalkyl group. However, it may be another type of ring group such as a heterocycloalkyl group, an aryl group, or a heteroaryl group.

In the present invention, heterocycloalkyl groups refer to aromatic and non-aromatic cyclic radicals containing one or more heteroatoms, wherein one or more heteroatoms are O, S, N, P, B, Si, and Se, preferably It is selected from O, N or S, and specifically, when N is included, it may be aziridine, pyrrolidine, piperidine, azepane, azocan, etc., which also include monocyclic or polycyclic, and additionally by other substituents may be substituted with, and polycyclic refers to a group in which a heterocycloalkyl group is directly connected or condensed with another ring group. it may be a gimmick

In the present invention, the cycloalkenyl group is a cyclic unsaturated hydrocarbon group that has one or more carbon double bonds and is not an aromatic ring, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, 1, 3-cyclohexadienyl group, 1,4-cyclohexadienyl group, 2,4-cycloheptadienyl group, 1,5-cyclooctadienyl group, etc., but are not limited thereto.

In the present invention, the aromatic hydrocarbon ring or aryl group may be monocyclic or polycyclic, and examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, a stilbene group, and the like, and examples of the polycyclic aryl group include a naphthyl group. , anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group, chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthene group, etc., but the scope of the present invention is not limited It is not limited only to these examples.

In the present invention, the aromatic heterocyclic or heteroaryl group is an aromatic ring containing at least one heteroatom, for example, a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, and an oxadia group. Zol group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group , pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group , dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, etc. However, the present invention is not limited thereto.

In the present invention, the aliphatic hydrocarbon ring is a non-aromatic ring and means a ring consisting only of carbon and hydrogen atoms, and includes, for example, monocyclic or polycyclic, and may be further substituted by other substituents, and polycyclic means other As meaning a group directly connected to or condensed with a ring group, the other ring group may be an aliphatic hydrocarbon ring, but may be a different type of ring group, for example, an aliphatic heterocycle, an aryl group, a heteroaryl group, or the like. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, adamantyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclo Cycloalkyl such as hexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, and cyclohexane, cyclo cycloalkanes such as pentane, and cyclocycloalkenes such as cyclohexene and cyclobutene, but are not limited thereto.

In the present invention, the aliphatic heterocycle refers to an aliphatic ring including at least one of heteroatoms, and includes heteroatoms such as O, S, Se, N or Si, and also includes monocyclic or polycyclic, other substituents may be further substituted by, and polycyclic refers to a group in which a heterocycloalkyl, heterocycloalkane, heterocycloalgen group, etc. is directly connected or condensed with another ring group, and the other ring group may be an aliphatic heterocycle, It may be another type of cyclic group, such as an aliphatic hydrocarbon ring, an aryl group, a heteroaryl group, and the like.

In the present invention, the aliphatic aromatic mixed ring group means a ring in which two or more rings are connected to each other and condensed, and an aliphatic ring and an aromatic ring are condensed to have non-aromaticity as a whole, and also polycyclic aliphatic aromatic mixture In addition to carbon in the ring, it may contain a hetero atom selected from N, O, P and S.

In the present invention, the alkoxy group may be specifically methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like, but is not limited thereto.

In the present invention, the silyl group may include -SiH ₃ , an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, an arylheteroarylsilyl group, a heteroarylsilyl group, and the like, and the arylsilyl group is -SiH ₃ , means a silyl group in which one or two or three hydrogens are substituted with an aryl group, and the alkylsilyl group in -SiH ₃ means an amine in which one, two or three hydrogens are substituted with alkyl, and the alkylarylsilyl group In -SiH ₃ , each of at least one hydrogen is substituted with an alkyl group and an aryl group to mean a silyl group including one or two alkyl groups and two or one corresponding aryl group, and the arylheteroarylsilyl group is -SiH ₃ In, each of at least one hydrogen is substituted with an aryl group and a heteroaryl group to mean a silyl group including one or two aryl groups and two or one corresponding heteroaryl group, and the heteroarylsilyl group is -SiH ₃ In the present invention, as a silyl group in which one, two, or three hydrogens are substituted with a heteroaryl group, examples of the arylsilyl group include a substituted or unsubstituted monoarylsilyl group, a substituted or unsubstituted diarylsilyl group, Or there is a substituted or unsubstituted triarylsilyl group, the same applies to the alkylsilyl group and the heteroarylsilyl group.

Here, each aryl group in the arylsilyl group, the heteroarylsilyl group and the arylheteroarylsilyl group may be a monocyclic aryl group or a polycyclic aryl group, and the arylsilyl group, heteroarylsilyl group and arylheteroarylsilyl group Each heteroaryl group in may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

In addition, specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, and the like. and one or more hydrogen atoms in the silyl group may be substituted with the same substituents as in the case of the aryl group.

In the present invention, the amine group may include -NH ₂ , an alkylamine group, an arylamine group, an alkylarylamine group, an arylheteroarylamine group, a heteroarylamine group, and the like, and the arylamine group is -NH ₂ , Means an amine in which one or two hydrogens are substituted with an aryl group, an alkylamine group in -NH ₂ means an amine in which one or two hydrogens are substituted with an alkyl, and an alkylarylamine group in -NH ₂ , One hydrogen is an alkyl group and the other hydrogen is an amine substituted with an aryl group, and the arylheteroarylamine group is -NH ₂ in which one hydrogen is substituted with an aryl group and the other hydrogen is an amine substituted with a heteroaryl group means, and the heteroarylamine group is -NH ₂ in which one or two hydrogens are substituted with a heteroaryl group. Examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted There is a cyclic diarylamine group, or a substituted or unsubstituted triarylamine group, and the same applies to the alkylamine group and the heteroarylamine group.

Here, each aryl group in the arylamine group, the heteroarylamine group and the arylheteroarylamine group may be a monocyclic aryl group or a polycyclic aryl group, and the arylamine group, heteroarylamine group and arylheteroarylamine group Each heteroaryl group in may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. Alternatively, it may be a polycyclic aryl group, and each heteroaryl group in the arylamine group, the heteroarylamine group and the arylheteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

In the present invention, the cycloalkyloxy group, the aryloxy group, the heteroaryloxy group, the cycloalkylthio group, the arylthio group, the cyclylaryl group, the aryl group, and the heteroaryl group in the heteroarylthio group include the aforementioned cyclylaryl group, aryl The same as the examples of the group and heteroaryl group, specifically, for example, an aryloxy group, phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethyl Phenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl -2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, etc. and the arylthioxy group includes, but is not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group, and the like.

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

More specifically, the compound represented by [Formula A] or [Formula B] according to the present invention may be any one selected from the following compounds, and specific substituents can be clearly identified through this, provided that, by this, in the present invention The range of [Formula A] or [Formula B] is not limited.

As can be seen from the above specific compounds, the compound according to the present invention forms a polycyclic ring structure, and includes a structure represented by [Structural Formula G] and/or [Structural Formula W] here, an organic light emitting material having unique properties can be synthesized, and a material that satisfies the conditions required by each organic layer, preferably a material employed in the light emitting layer, can be manufactured, and through this, an organic light emitting device with high efficiency and long life can be realized.

In addition, another aspect of the present invention relates to an organic light emitting device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer has the [Formula A] Or it may include at least one compound according to the present invention represented by [Formula B].

That is, the organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode and a second electrode and an organic material layer disposed therebetween, and according to the present invention [Formula A] or [Formula B] Except that the compound of the device is used in the organic layer of the device, it can be manufactured using a conventional device manufacturing method and material.

The organic layer of the organic light emitting diode according to the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, and the like. However, the present invention is not limited thereto and may include a smaller number or a larger number of organic layers, and the organic material layer structure of the preferred organic light emitting device according to the present invention will be described in more detail in Examples to be described later.

The organic light emitting device according to the present invention includes an anode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode, and if necessary, may further include a hole injection layer between the anode and the hole transport layer, and also between the electron transport layer and the cathode It may further include an injection layer, in addition to that, it is possible to further form an intermediate layer of one or two layers, and it is also possible to further form a hole blocking layer or an electron blocking layer.

As a preferred embodiment of the present invention, in the present invention, the organic layer interposed between the first electrode and the second electrode includes a light emitting layer, the light emitting layer is made of a host and a dopant, and the [Formula A] according to the present invention Alternatively, the compound represented by [Formula B] may be included as a dopant in the light emitting layer.

In addition, in the organic light emitting device according to the present invention, the host material employed in the light emitting layer may be an anthracene compound represented by the following [Formula 1].

[Formula 1]

In the above [Formula 1],

R ₄₁ to R ₄₈ are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C 6 to C 6 50 aryl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 3 to C 30 heterocycloalkyl group, substituted or unsubstituted C 2 to C 50 heteroaryl group, substituted or unsubstituted an alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms , a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group.

Ar ₁ and Ar ₃ are the same as or different from each other, and each independently represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms.

Ar ₂ and Ar ₄ are the same as or different from each other, and each independently represents hydrogen, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C3 to C3 It is selected from a 30 heterocycloalkyl group, a substituted or unsubstituted C 2 to C 50 heteroaryl group, and a substituted or unsubstituted C 3 to C 30 aliphatic aromatic mixed ring group.

D _n represents the number of hydrogens in [Formula 1] replaced with deuterium, and n is an integer of 0 to 50.

According to an embodiment of the present invention, the compound represented by [Formula 1] may be any one selected from the group consisting of the following compounds.

In this case, the content of the dopant in the light emitting layer may be generally selected from about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

In addition, the light emitting layer may further include a variety of hosts and various dopant materials in addition to the dopant and the host. Accordingly, the dopant in the light emitting layer is a compound other than one compound represented by the [Formula A] or [Formula B] One or more kinds may be mixed or laminated, and the host in the light emitting layer may be used by mixing or stacking one or more other compounds in addition to one compound represented by [Formula 1].

Meanwhile, a detailed structure of an organic light emitting diode according to an embodiment of the present invention, a manufacturing method thereof, and each organic layer material will be described as follows.

First, an anode is formed by coating a material for an anode electrode on a substrate. Here, as the substrate, a substrate used in a conventional organic light emitting device is used, and an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, handling and water resistance is preferable. In addition, as a material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used.

A hole injection layer is formed by vacuum thermal evaporation or spin coating of a hole injection layer material on the anode electrode, and then vacuum thermal evaporation or spin coating of a hole transport layer material on the hole injection layer to form a hole transport layer .

The hole injection layer material may be used without particular limitation as long as it is commonly used in the art, and as a specific example, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD [N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD [N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ] HAT-CN [1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile] and the like can be used.

In addition, the hole transport layer material is also not particularly limited as long as it is commonly used in the art, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1- Biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (?-NPD), etc. can be used.

Subsequently, a hole auxiliary layer and a light emitting layer are sequentially stacked on the hole transport layer, and a hole blocking layer is selectively deposited on the light emitting layer by a vacuum deposition method or a spin coating method to form a thin film. The hole blocking layer serves to prevent this problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level because the lifetime and efficiency of the device are reduced when holes are introduced into the cathode through the organic light emitting layer. . In this case, the hole blocking material used is not particularly limited, but has an electron transport ability and has an ionization potential higher than that of a light emitting compound, and typically BAlq, BCP, TPBI, or the like may be used. As the material used for the hole blocking layer, any one selected from BAlq, BCP, Bphen, TPBI, NTAZ, BeBq ₂ , OXD-7 and Liq may be used, but is not limited thereto.

The present invention by forming an electron injection layer after depositing an electron transport layer on the hole blocking layer through a vacuum deposition method or a spin coating method, and vacuum thermal evaporation of a metal for forming a cathode on the electron injection layer to form a cathode electrode An organic light emitting diode according to an embodiment is completed.

Here, as the metal for forming the cathode, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag) may be used, and in order to obtain a top light emitting device, a transmissive cathode using ITO or IZO may be used.

The electron transport layer material serves to stably transport electrons injected from the cathode, and a known electron transport material may be used. Examples of known electron transport materials include quinoline derivatives, especially tris(8-quinolinolate)aluminum (Alq3), TAZ, BAlq, beryllium bis(benzoquinolin-10- Materials such as olate: Bebq2), oxadiazole derivatives PBD, BMD, BND, etc. may be used.

In addition, each of the organic layers may be formed by a monomolecular deposition method or a solution process, wherein the deposition method evaporates a material used as a material for forming each layer through heating in a vacuum or low pressure state. It refers to a method of forming a thin film, and the solution process mixes a material used as a material for forming each layer with a solvent, and uses it inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating It refers to a method of forming a thin film through a method such as.

In addition, the organic light emitting diode according to the present invention may be used in a flat panel display device, a flexible display device, a monochromatic or white flat panel lighting device, a monochromatic or white flexible lighting device, a vehicle display device, a virtual or augmented reality display device, and the like.

Hereinafter, synthesis examples and device examples of preferred compounds are provided to help the understanding of the present invention. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereby.

Synthesis example One : [ 4] of synthesis

Synthesis example 1-1: Synthesis of A-1

<A-1a> <A-1b> <A-1>

In the reactor, <A-1a> 50 g, <A-1b> (refer to prior patent document JP6023635 synthesis) 55.6 g, palladium acetate 0.99 g, (±)-2,2'bis(diphenylphosphino)-1,1 'Binaphthalene 2.76 g, sodium tert-butoxide 42.5 g, and toluene 500 mL were added, and the mixture was stirred under reflux for 4 hours. After cooling to room temperature, water was added, and the organic layer was separated. After adding magnesium sulfate, it was filtered and then concentrated under reduced pressure. It purified by silica gel column chromatography to obtain <A-1>. (79 g, 90%)

Synthesis example 1-2: Synthesis of A-2

<A-1> <A-2a> <A-2>

15 g of <A-1>, 13.1 g of <A-2a> (synthesis referenced in prior patent document CN 107868109), 0.39 g of bis(tertiarybutylphosphine)palladium, 7.3 g of sodium tert-butoxide, 150 g of <A-2a> in the reactor mL was added, and the mixture was stirred under reflux for 6 hours. After cooling to room temperature, water was added, and the organic layer was separated. After adding magnesium sulfate, it was filtered and then concentrated under reduced pressure. It purified by silica gel column chromatography to obtain <A-2>. (19.9 g, 83.4%)

Synthesis example 1-3: Synthesis of A-3

<A-3a> <A-3b> <A-3>

In Synthesis Example 1-1, <A-3b> was used instead of <A-1a>, and <A-3a> was used instead of <A-1b> to obtain <A-3> in the same manner. (yield 76.3%)

Synthesis example 1-4: Synthesis of A-4

<A-2> <A-3> <A-4>

In Synthesis Example 1-2, <A-3> was used instead of <A-1>, and <A-2> was used instead of <A-2a> to obtain <A-4> in the same manner. (yield 70.5%)

Synthesis example 1-5 : [ 4] of synthesis

<A-4> [4]

15 g of <A-4> and 150 mL of tertiary butylbenzene were added to the reactor, and then 32.9 mL of 1.7M tertiary butyllithium was added dropwise at -78°C. After the temperature was raised to 60 °C, the mixture was stirred for 3 hours, and then nitrogen was blown at 60 °C to completely remove pentane. After cooling to -78 °C, 5 mL of boron tribromide was added dropwise. After raising the temperature to room temperature and stirring for 2 hours, it was cooled to 0 °C, and 4.7 mL of N,N-diisopropylethylamine was added dropwise. After raising the temperature to 120 °C, the mixture was stirred for 12 hours. After cooling to room temperature, 32 mL of a 10% aqueous sodium acetate solution and ethyl acetate were added, and the organic layer was separated. After adding magnesium sulfate, it was filtered and then concentrated under reduced pressure. Purification by silica gel column chromatography gave [4]. (2.4 g, 16.5%)

MS (MALDI-TOF): m/z 848.43 [M ⁺ ]

Synthesis example 2 : [ 10] of synthesis

Synthesis example 2-1: Synthesis of B-1

<B-1a> <A-1b> <B-1>

In Synthesis Example 1-1, <B-1> was obtained in the same manner using <B-1a> instead of <A-1a>. (yield 90.3%)

Synthesis example 2-2: Synthesis of B-2

<B-1> <B-2a> <B-2>

In Synthesis Example 1-2, <B-1> was used instead of <A-1>, and <B-2a> was used instead of <A-2a> to obtain <B-2> in the same manner. (yield 89.3%)

Synthesis example 2-3: Synthesis of B-3

<B-3a> <B-3b> <B-3>

50 g of <B-3a>, 75.4 g of <B-3b>, 0.8 g of palladium acetate, 2.05 g of xanthos, 25.6 g of sodium tertiary butoxide, and 500 mL of toluene were added to the reactor, followed by stirring under reflux for 6 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. It purified by silica gel column chromatography to obtain <B-3>. (55 g, 71%)

Synthesis example 2-4: Synthesis of B-4

<B-3> <A-3a> <B-4>

In Synthesis Example 1-1, <B-3> was used instead of <A-1a>, and <A-3a> was used instead of <A-1b> to obtain <B-4> in the same manner. (Yield 87.7%)

Synthesis example 2-5: Synthesis of B-5

<B-2> <B-4> <B-5>

In Synthesis Example 1-4, <B-2> was used instead of <A-2>, and <B-4> was used instead of <A-3> to obtain <B-5> in the same manner. (yield 82.6%)

Synthesis example 2-6 : [ 10] of synthesis

<B-5> [10]

In Synthesis Example 1-5, [10] was obtained in the same manner using <B-5> instead of <A-4>. (Yield 13.1%)

MS (MALDI-TOF): m/z 1101.62 [M ⁺ ]

Synthesis example 3: [ 58] of synthesis

Synthesis example 3-1: Synthesis of C-1

<C-1a> <A-3a> <C-1>

In Synthesis Example 1-3, <C-1> was obtained in the same manner using <C-1a> instead of <A-3b>. (yield 93.1%)

Synthesis example 3-2: Synthesis of C-2

<A-1a> <C-1> <C-2>

In Synthesis Example 1-1, <C-2> was obtained in the same manner using <C-1> instead of <A-1b>. (Yield 88.8%)

Synthesis example 3-3: Synthesis of C-3

<C-2> <A-3a> <C-3>

In Synthesis Example 1-4, <C-2> was used instead of <A-2>, and <A-3a> was used instead of <A-3> to obtain <C-3> in the same manner. (yield 72.7%)

Synthesis example 3-4: Synthesis of C-4

<C-3> <B-2a> <C-4>

In Synthesis Example 1-2, <C-3> was used instead of <A-1>, and <B-2a> was used instead of <A-2a> to obtain <C-4> in the same manner. (Yield 81.4%)

Synthesis example 3-5 : [ 58] of synthesis

<C-4> [58]

In Synthesis Example 1-5, [58] was obtained in the same manner using <C-4> instead of <A-4>. (Yield 13.9%)

MS (MALDI-TOF): m/z 776.40 [M ⁺ ]

Example 1 to 6: Preparation of organic light emitting device

After patterning so that the light emitting area of the ITO glass has a size of 2 mm × 2 mm, it was washed. After the ITO glass was mounted in a vacuum chamber, the base pressure was set to 1 x 10 ^-7 torr, and then DNTPD (700 Å) and [Formula G] (250 Å) were formed on the ITO in this order. The light emitting layer is formed by mixing the host [BH-1] described below and the compound of the present invention (2 wt%) (250 Å), and then, as an electron transport layer [Formula E-1] and [Formula E-2] An organic light emitting device was prepared by forming a film in the order of 300 Å and [Formula E-1] as an electron injection layer in a 1:1 ratio of 5 Å and Al (1000 Å), and the emission characteristics of the organic light emitting device were at 0.4 mA. measured.

[DNTPD] [Formula G]

[Formula E-1] [Formula E-2] [BH-1]

comparative example One

An organic light emitting device was manufactured in the same manner except that [BD-1] was used instead of the compound of the present invention used in the above example, and the light emitting characteristic of the organic light emitting device was measured at 0.4 mA. The structure of [BD-1] is as follows.

[BD-1]

For the organic light emitting devices manufactured according to Examples 1 to 6 and Comparative Example 1, voltage, external quantum efficiency, and lifetime were measured, and the results are shown in Table 1 below.

division host dopant Voltage (V) Efficiency (EQE, %) Lifetime (T97, hr) Example 1 BH-1 [3] 3.5 9.5 196 Example 2 BH-1 [4] 3.5 9.8 203 Example 3 BH-1 [8] 3.5 10.4 232 Example 4 BH-1 [10] 3.5 10.4 241 Example 5 BH-1 [43] 3.5 10.1 210 Example 6 BH-1 [58] 3.5 9.9 221 Comparative Example 1 BH-1 BD-1 3.5 8.3 133

As can be seen in [Table 1], when the compound implemented by [Formula A] or [Formula B] according to the present invention is employed as a dopant in the light emitting layer of the organic light emitting device, the structural structure of the compound according to the present invention Compared to the device employing the compound of the comparative example in contrast to the characteristics (Comparative Example 1), the external quantum efficiency is improved and the lifespan characteristics are remarkably improved. have.

Claims (18)

A compound represented by the following [Formula A] or [Formula B]:
[Formula A]

[Formula B]

In the [Formula A] and [Formula B],
Q ₁ to Q ₃ are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 50 carbon atoms, and a substituted or unsubstituted carbon number 3 to any one selected from among the aliphatic aromatic mixed rings of 30,
X is any one selected from B, N, CR ₁ , SiR ₂ , P, P=O and P=S,
Y ₁ to Y ₃ are the same as or different from each other, and each independently represent a divalent group, which is any one selected from the structural formulas represented by the following (Y-1) to (Y-11),

Wherein R ₁ To R ₁₃ are the same or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 2 to C 24 alkenyl group, a substituted or unsubstituted An alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, substituted or Unsubstituted C1-C30 heterocycloalkyl group, substituted or unsubstituted C1-C30 heteroalkyl group, substituted or unsubstituted C1-C50 heteroaryl group, substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, substituted or unsubstituted an alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted hetero group having 2 to 30 carbon atoms Any one selected from an arylthio group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a nitro group, a cyano group, a halogen group, and a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms and ,
The [Formula A] and [Formula B] are each characterized in that it has at least one structure selected from the following [Structural Formula G] and [Structural Formula W],
[Formula G] [Formula W]

In the [Structural Formula G] and [Structural Formula W],
Q ₄ to Q ₅ is each independently the same as the definition of Q ₁ to Q ₃ above,
G ₁ is each independently CR ₁₄ R ₁₅ or SiR ₁₆ R ₁₇ , and G ₂ is each independently any one selected from CR ₁₈ R ₁₉ , SiR ₂₀ R ₂₁ , NR ₂₂ , O, S, Se, and BR ₂₃ ,
Each of R ₁₄ to R ₂₃ is the same as the definition of R ₁ to R ₁₃ ,
* in [Formula G] means a site condensed to the ring of Q ₁ to Q ₃ in any one of [Formula A] and [Formula B],
When the [Structural Formula W] is connected to any one of the [Formula A] and [Formula B], it may be connected to Q ₄ , Q ₅ , G ₁ or G ₂ ,
The R ₁ to R ₂₃ , Q ₁ to Q ₅ , G ₁ , G ₂ and their substituents may combine with an adjacent substituent to form a substituted or unsubstituted ring. According to claim 1,
[Formula A] or [Formula B] each of Q ₁ to Q ₃ At least one of the [Structural Formula G] is a condensed compound. According to claim 1,
[Formula A] or [Formula B] each Y _One to Y ₂ and Q _One to Q ₃ At least one of the [Structural Formula W] and a substituted structure is a compound. 3. The method of claim 2,
Each of X in [Formula A] and [Formula B] is B, and the [Structural Formula G] is a compound condensed to Q ₂ . According to claim 1,
wherein R ₁ to R ₁₃ are the same or different from each other, and each independently a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C 3 to C 30 of a cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 50 carbon atoms, and a substituted or unsubstituted A compound that is any one selected from an aliphatic aromatic mixed ring group having 3 to 30 carbon atoms. 3. The method of claim 2,
The [Formula A] and [Formula B] each Q ₁ To Q ₃ , Y ₁ And Y ₂ At least one of [Structural Formula W] is a substituted compound. According to claim 1,
The [Structural Formula G] and [Structural Formula W] each of Q ₄ and Q ₅ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms. According to claim 1,
The [Formula A] is any one selected from [Formula A-1] to [Formula A-6], wherein the [Formula B] is any one selected from [Formula B-1] to [Formula B-6] Compounds represented by one:
[Formula A-1] [Formula A-2]

[Formula A-3] [Formula A-4]

[Formula A-5] [Formula A-6]

[Formula B-1] [Formula B-2]

[Formula B-3] [Formula B-4]

[Formula B-5] [Formula B-6]

In the [Formula A-1] to [Formula A-6] and [Formula B-1] to [Formula B-6],
Z is CR or N, wherein R is the same as the definitions of R ₁ to R ₁₃ , respectively (a plurality of Z and R are the same or different from each other),
The plurality of R may be bonded to each other or connected to adjacent substituents to form an alicyclic, aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic, aromatic monocyclic or polycyclic ring may be selected from among N, S and O may be substituted with any one or more heteroatoms selected,
X, Y ₁ to Y ₃ , G ₁ and G ₂ are the same as defined in [Formula A] and [Formula B], respectively. According to claim 1,
The [Formula A] or [Formula B] is any one selected from the compounds represented by the following formula:

A first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode,
The organic light emitting device comprising at least one compound represented by the [Formula A] or [Formula B] according to claim 1, wherein the organic layer. 11. The method of claim 10,
The organic layer includes at least one of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and a light emitting layer,
At least one of the layers is an organic light emitting device comprising a compound represented by the [Formula A] or [Formula B]. 12. The method of claim 11,
The light emitting layer consists of a host and a dopant, and the compound represented by [Formula A] or [Formula B] is an organic light emitting device in which the dopant is in the light emitting layer. 13. The method of claim 12,
The host is an organic light emitting device which is an anthracene compound represented by the following [Formula 1]:
[Formula 1]

In the above [Formula 1],
R ₄₁ to R ₄₈ are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C 6 to C 6 50 aryl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 3 to C 30 heterocycloalkyl group, substituted or unsubstituted C 2 to C 50 heteroaryl group, substituted or unsubstituted an alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms , a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, a nitro group, a cyano group and a halogen group,
Ar ₁ and Ar ₃ are the same as or different from each other, and are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms,
Ar ₂ and Ar ₄ are the same as or different from each other, and each independently represents hydrogen, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C3 to C3 Any one selected from a 30 heterocycloalkyl group, a substituted or unsubstituted C2 to C50 heteroaryl group, and a substituted or unsubstituted C3 to C30 aliphatic aromatic mixed ring group,
D _n means the number of hydrogens in [Formula 1] replaced with deuterium,
n is an integer from 0 to 50; 14. The method of claim 13,
The compound represented by the [Formula 1] is any one selected from the group consisting of the following compounds organic light emitting device:

12. The method of claim 11,
At least one layer selected from each of the layers is an organic light emitting device formed by a deposition process or a solution process. 13. The method of claim 12,
In the light emitting layer, the dopant is an organic light emitting device used by mixing or stacking at least one compound in addition to one compound represented by the above [Formula A] or [Formula B]. 14. The method of claim 13,
In the light emitting layer, the host is an organic light emitting device used by mixing or stacking one or more compounds in addition to one compound represented by [Formula 1]. 11. The method of claim 10,
The organic light emitting device may include a flat panel display device; flexible display devices; devices for flat-panel lighting of monochromatic or white color; devices for flexible lighting, monochromatic or white; vehicle display device; and a display device for virtual or augmented reality; An organic light emitting device, characterized in that it is used in any one selected from.