KR20230010573A - Organic light-emitting device - Google Patents

Abstract

The present invention relates to a long-life, high-efficiency organic light emitting device with remarkably improved lifespan characteristics by employing a polycyclic compound having a characteristic structure and a substituent as a dopant of a light emitting layer, and an anthracene derivative compound having a characteristic structure and a substituent as a host of the light emitting layer, respectively.

Description

Organic light-emitting device {Organic light-emitting device}

The present invention relates to a long-life, high-efficiency organic light-emitting device having improved luminous efficiency and lifetime characteristics by employing a boron-containing polycyclic compound as a dopant and an anthracene derivative compound having a structure containing deuterium in an anthracene skeleton as a host in an emission layer.

In the organic light emitting device, electrons injected from the electron injection electrode (cathode electrode) and holes injected from the hole injection electrode (anode electrode) are combined in the light emitting layer to form excitons, and the excitons generate energy. It is a self-luminous device that emits light while emitting, 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 limelight as a next-generation light source due to the advantages of being applicable to full-color flat light emitting displays. .

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 materials constituting each organic layer, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and an electron blocking material Although it should be preceded that the etc. be supported by stable and efficient materials, there is still a need to develop a stable and efficient structure of an organic layer for an organic light emitting device and each material.

In particular, in order to obtain maximum efficiency in the light emitting layer, the energy bandgap of the host and the dopant must be properly combined so that holes and electrons can move to the dopant through a stable electrochemical path and form excitons.

Accordingly, an object of the present invention is to provide a long-life, high-efficiency organic light emitting device having improved light emitting efficiency and excellent lifetime characteristics by employing characteristic host materials and dopant materials for the light emitting layer in the organic light emitting device.

In order to solve the above problems, the present invention is an organic light emitting device including a first electrode, a second electrode opposite to the first electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer A light emitting layer including a host and a dopant, wherein the dopant includes at least one of compounds represented by [Formula 1] and [Formula 2], and the host is an organic anthracene compound represented by [Formula 3] A light emitting device is provided.

[Formula 1] [Formula 2]

[Formula 3]

The compound represented by [Formula 3] is characterized in that it has a structure containing deuterium, that is, at least one or more of R ₁₁ to R ₁₈ is deuterium, and additional Ar ₁ to Ar ₄ hydrogen is replaced by deuterium. can

The characteristic structures of [Formula 1], [Formula 2] and [Formula 3], definitions of each substituent, and specific compounds realized thereby will be described later.

The organic light-emitting device according to the present invention employs a boron-containing polycyclic compound having a silyl group as a substituent as a dopant and an anthracene derivative compound having a structure containing deuterium in an anthracene skeleton as a host in the light-emitting layer to implement a long-life and high-efficiency organic light-emitting device. Therefore, it can be usefully used for various display devices such as flat, flexible, and wearable displays as well as lighting devices.

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

The present invention relates to an organic light emitting device composed of 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 includes a light emitting layer including a host and a dopant, , The dopant includes at least one compound represented by [Formula 1] and [Formula 2], and the host relates to an organic light emitting device comprising an anthracene compound represented by [Formula 3].

[Formula 1] [Formula 2]

In [Formula 1] and [Formula 2],

X is B, P=O, P=S or Al, Y ₁ and Y ₂ are each independently NR ₁ , O, S, CR ₂ R ₃ or SiR ₄ R ₅ , Y ₃ is O or S .

According to an embodiment of the present invention, X may be B (boron).

A ₁ to A ₃ rings are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 5 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 50 carbon atoms, or a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms. and substituted or unsubstituted aliphatic aromatic mixed rings having 3 to 30 carbon atoms.

According to one embodiment of the present invention, the A ₂ ring is characterized in that it has a substituted or unsubstituted amine group having 0 to 30 carbon atoms as a substituent.

According to one embodiment of the present invention, the amine group may be a diarylamine group, at least one of the aryl groups of the diarylamine group may be a substituted or unsubstituted phenyl group, and the substituent of the phenyl group may be substituted at an ortho position may be an aryl group having 6 to 20 carbon atoms.

In addition, R, R ₁ to R ₅ are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 2 to 30 carbon atoms. Or an 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 heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted hetero group having 2 to 50 carbon atoms Aryl group, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted carbon atoms An arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 30 carbon atoms, a substituted or unsubstituted silyl group having 0 to 30 carbon atoms, a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, Any one selected from a nitro group, a cyano group, and a halogen group, except that the plurality of R's consist of only a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

According to one embodiment of the present invention, at least one of the plurality of Rs may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In addition, R ₁ to R ₅ may be connected to the A ₁ to A ₃ rings to further form an alicyclic or aromatic monocyclic or polycyclic ring.

In addition, the plurality of R's may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

In addition, R ₂ and R ₃ and R ₄ and R ₅ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

In addition, at least one of the hydrogens of the compound represented by [Formula 1] or [Formula 2] according to the present invention is characterized in that it is substituted with deuterium.

According to one embodiment of the present invention, the [Formula 1] is represented by the following [Formula 1-1], and the [Formula 2] may be a polycyclic compound represented by the following [Formula 2-1].

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

In [Formula 1-1] and [Formula 2-1], the definitions of A ₁ , A ₂ , X, Y ₁ to Y ₃ and R are the same as those defined in [Formula 1] and [Formula 2], At least one of the plurality of Rs is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[Formula 3]

In the above [Formula 3],

R ₁₁ to R ₁₈ are the same as or different from each other, and each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted Aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted Or an 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 alkylthio group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkylthio group having 5 to 30 carbon atoms. Arylthioxy group, substituted or unsubstituted amine group having 0 to 30 carbon atoms, substituted or unsubstituted silyl group having 0 to 30 carbon atoms, substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, nitro group, cyano group It is selected from a furnace group and a halogen group.

However, at least one of R ₁₁ to R ₁₈ is characterized in that deuterium, and according to an embodiment of the present invention, at least 4 of R ₁₁ to R ₁₈ may be deuterium.

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 are each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted 3 carbon atoms. to 30 heterocycloalkyl groups, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, and substituted or unsubstituted aliphatic aromatic mixed ring groups having 3 to 30 carbon atoms.

D _n means the number of hydrogens in Ar ₁ to Ar ₄ replaced with deuterium, and n is an integer from 0 to 50.

As such, the compound represented by [Formula 3] according to the present invention is a compound in which at least one deuterium is introduced into anthracene, and may further include additional deuterium.

Meanwhile, in [Formula 1], [Formula 2], and [Formula 3], the term 'substituted or unsubstituted' means that A ₁ to A ₃ , R, R ₁ to R ₅ , etc. are deuterium and cyano groups, respectively. , A halogen group, a hydroxyl group, a nitro group, an amino group, an alkyl group, a cycloalkyl group, a halogenated alkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, a heterocycloalkyl group, an aryl group, an arylalkyl group, a heteroaryl group, a heteroarylalkyl group, an alkoxy group, substituted with one or two or more substituents selected from the group consisting of an alkylamine group, an arylamine group, a heteroarylamine group, an alkylsilyl group, an arylsilyl group, and an aryloxy group, or substituted with a substituent in which two or more substituents are connected; or without any substituent.

In addition, the carbon number range of the alkyl 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 part where the substituent is substituted It means the total number of carbon atoms constituting the alkyl part or the aryl part when viewed as unsubstituted without being unsubstituted. For example, a phenyl group in which a butyl group is substituted 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 of forming a ring by combining with adjacent groups means that a substituted or unsubstituted alicyclic or aromatic ring can be formed by combining with adjacent groups, and 'adjacent substituents' refer to the corresponding It may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the 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 a straight chain or branched chain, and specific examples include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a 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 is not limited to these.

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

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

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, spirundecyl , adamantyl, etc., but is 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, other types of ring groups such as heterocycloalkyl groups, aryl groups, and heteroaryl groups may also be used.

In the present invention, heterocycloalkyl groups refer to aromatic and non-aromatic cyclic radicals containing one or more heteroatoms, one or more heteroatoms being O, S, N, P, B, Si, and Se, preferably It is selected from O, N or S, specifically, when N is included, it may be aziridine, pyrrolidine, piperidine, azepane, azocan, etc., which also includes monocyclic or polycyclic, and may be added by other substituents. It may be substituted with, and polycyclic refers to a group in which a heterocycloalkyl group is directly connected or condensed with another ring group, and the other ring group may be a heterocycloalkyl group, but other types of rings such as cycloalkyl groups, aryl groups, and heteroaryl groups it could be a flag

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, and includes cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, 1, 3-cyclohexadienyl group, 1,4-cyclohexadienyl group, 2,4-cycloheptadienyl group, 1,5-cyclooctadienyl group, and the like, 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, acenaphthacennyl group, triphenylene group, fluoranthene group, etc., but the scope of the present invention It is not limited to only these examples.

In the present invention, the aromatic heterocycle or heteroaryl group is an aromatic ring containing at least one of hetero atoms, examples of which include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, and an oxadia group. sol 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 , pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzooxazole 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, it is not limited to these.

In the present invention, an aliphatic hydrocarbon ring is a non-aromatic ring and means a ring composed of only carbon and hydrogen atoms, and includes monocyclic or polycyclic as an example, and may be further substituted by other substituents, and polycyclic means other This means a group directly linked to or condensed with a ring group, and other ring groups may be aliphatic hydrocarbon rings, but may also be other types of ring groups, such as aliphatic heterocycles, aryl groups, and heteroaryl groups. 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, cyclohexyl group cycloalkanes such as pentane, and cyclocycloalkenes such as cyclohexene and cyclobutene, but are not limited thereto.

In the present invention, an aliphatic heterocycle means an aliphatic ring containing at least one of heteroatoms, and includes a heteroatom such as O, S, Se, N, or Si, and also includes a monocyclic or polycyclic ring, and other substituents It 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 heterocyclic ring, Other types of ring groups such as aliphatic hydrocarbon rings, aryl groups, heteroaryl groups, and the like may also be used.

In the present invention, the aliphatic aromatic mixed ring group means a ring in which two or more rings are connected and condensed, and the aliphatic ring and the aromatic ring are condensed to have non-aromaticity as a whole, and also a polycyclic aliphatic aromatic mixture. In addition to carbon, the ring may contain heteroatoms 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, etc., 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 In An alkylsilyl group means an amine in which one or two or three hydrogens are substituted with an aryl group, and an alkylsilyl group in -SiH ₃ means an amine in which one or two or three hydrogens are substituted with an alkyl group. In -SiH ₃ , 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 aryl groups corresponding thereto, and the arylheteroarylsilyl group is -SiH ₃ In, each 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 heteroaryl group corresponding thereto, and the heteroarylsilyl group is -SiH ₃ , which means a silyl group in which one or two or three hydrogens are substituted with a heteroaryl group, and 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 heteroarylsilyl group.

Here, each of the aryl groups 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, the heteroarylsilyl group, and the 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 , 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 represents an alkyl group and the other hydrogen represents an amine substituted with an aryl group, and the arylheteroarylamine group in -NH ₂ represents an amine in which one hydrogen is substituted with an aryl group and the other hydrogen is substituted with a heteroaryl group. The heteroarylamine group in -NH ₂ means an amine in which one or two hydrogens are substituted with a heteroaryl group, and 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 alkylamine group and heteroarylamine group also correspond to the same.

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

In the present invention, a cycloalkyloxy group, an aryloxy group, a heteroaryloxy group, a cycloalkylthio group, an arylthio group, and a cycloaryl group among heteroarylthio groups, aryl groups, and heteroaryl groups are the aforementioned cycloaryl groups, aryl groups, and the like. It is the same as an example of a group, a heteroaryl group, and specifically, for example, an aryloxy group, a 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. Examples of the arylthioxy group include, but are not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, and a 4-tert-butylphenylthioxy group.

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

According to one embodiment of the present invention, the dopant compound represented by [Formula 1] or [Formula 2] may be any one selected from the following compounds, but the range is not limited thereby.

In addition, according to one embodiment of the present invention, the anthracene host compound represented by [Formula 3] may be any one selected from the following compounds, but the range is not limited thereby.

In this case, the content of the dopant in the light emitting layer may be typically selected in the range of 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 various hosts and various dopant materials in addition to the dopant and host compound according to the present invention. In particular, the light emitting layer host may be used by mixing or stacking two or more different compounds.

The organic layer of the organic light emitting device according to the present invention may have a single-layer structure, or may have a multi-layer 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, it is not limited thereto and may include a smaller or larger number of organic layers, and an organic material layer structure of a preferable organic light emitting device according to the present invention will be described in more detail in the embodiments to be described later.

Hereinafter, an embodiment of the organic light emitting device according to the present invention will be described in more detail.

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 may further include a hole injection layer between the anode and the hole transport layer, if necessary, and electron transport layer between the electron transport layer and the cathode. It may further include an injection layer, and in addition to that, it is possible to further form one or two intermediate layers, and a hole blocking layer or an electron blocking layer may be further formed. An organic layer having various functions may be further included according to characteristics.

Meanwhile, a detailed structure of an organic light emitting device according to an embodiment of the present invention, a manufacturing method thereof, and materials for each organic layer are 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 having excellent transparency, surface smoothness, ease of handling, and water resistance is preferable. In addition, as materials 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 top of the anode electrode, and then a hole transport layer is formed by vacuum thermal evaporation or spin coating of a hole transport layer material on top of the hole injection layer. .

As long as the hole injection layer material is commonly used in the art, it may be used without particular limitation, 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 ] etc. can be used.

In addition, the hole transport layer material is 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 (α-NPD) or the like can be used.

Subsequently, a hole auxiliary layer and a light emitting layer may be sequentially stacked on top of the hole transport layer, and a hole blocking layer may be selectively formed on top of the light emitting layer by a vacuum deposition method or a spin coating method. 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 lifespan and efficiency of the device are reduced when holes pass through the organic light emitting layer and flow into the cathode. . At this time, the hole-blocking material used is not particularly limited, but should have electron transport ability and higher ionization potential than the light emitting compound, and typically BAlq, BCP, TPBI, and the like may be used.

As a material used for the hole blocking layer, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq ₂ , OXD-7, Liq, etc. 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 thermally depositing a metal for forming a cathode on top of the electron injection layer to form a cathode electrode. An organic light emitting device according to an embodiment of is completed.

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

As the material for the electron transport layer, a known electron transport material may be used to stably transport electrons injected from the cathode. Examples of known electron transport materials are quinoline derivatives, in particular tris(8-quinolinolate)aluminum (Alq3), TAZ, BAlq, beryllium bis(benzoquinolin-10-noate) (beryllium bis(benzoquinolin-10- olate: Bebq2) and oxadiazole derivatives (PBD, BMD, BND, etc.) can also be used.

In addition, each of the organic layers may be formed by a single molecule deposition method or a solution process, wherein the deposition method evaporates a material used as a material for forming each layer through heating or the like 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 inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, and spin coating. It means a method of forming a thin film through the same method.

In addition, the organic light emitting device according to the present invention may be used for 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, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are intended to explain the present invention in more detail, and it will be apparent to those skilled in the art that the scope of the present invention is not limited thereto.

synthesis example One : [ 1] synthesis

synthesis example 1-1: Synthesis of A-1

<A-1a> <A-1>

After putting 50 g of <A-1a> and 50 mL of tetrahydrofuran into the reactor, 140 mL of a 2.0 M lithium diasopropylamide solution was added dropwise at -78 °C. After stirring at -78 °C for 3 hours, hexachloroethane was slowly added thereto, the temperature was raised to room temperature, and the mixture was stirred for 16 hours. After adding ethyl acetate and water, the organic layer was separated. Purification was performed by silica gel chromatography to obtain <A-1>. (42.5 g, 78.9%)

synthesis example 1-2: Synthesis of A-2

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

<A-1> 37.5 g, <A-2a> 12.7 g, tris (dibenzylideneacetone) dipalladium (0) 1.42 g, bis (diphenylphosphino) -1,1'-binaphthyl 0.96 g, 14.9 g of sodium tert-butoxide, and 375 mL of toluene were added, followed by reflux stirring for 3 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. Purification was performed by silica gel chromatography to obtain <A-2>. (24 g, 56%)

synthesis example 1-3: Synthesis of A-3

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

After adding 24 g of <A-2>, 16.3 g of <A-3a>, 0.4 g of bis(tri-tert-butylphosphine)palladium(0), 8.3 g of sodium tert-butoxide, and 240 mL of toluene to the reactor, , and stirred under reflux for 6 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. Purification was performed by silica gel chromatography to obtain <A-3>. (31.4 g, 97.5%)

synthesis example 1-4: Synthesis of A-4

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

After adding 41.2 g of <A-3>, 14.76 g of <A-4a>, 0.8 g of bis(tri-tert-butylphosphine)palladium(0), 10 g of sodium tert-butoxide, and 412 mL of toluene to the reactor, , and stirred under reflux for 6 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. Purification was performed by silica gel chromatography to obtain <A-4>. (50.2 g, 97.2%)

synthesis example 1-5: [ 1] synthesis

<A-4> [One]

After putting 50.2 g of <A-4> and 500 mL of tert-butylbenzene into the reactor, 71.9 mL of a 1.7 M tertiary butyllithium pentane solution was added dropwise at -78 °C. After raising the temperature to 60 ° C., stirring for 2 hours, pentane was completely removed by blowing nitrogen at 60 ° C. After cooling to -78 °C, 4.8 mL of boron tribromide was added dropwise. After raising the temperature to room temperature, the mixture was stirred for 2 hours, cooled to 0° C., and 8.9 mL of N,N-diisopropylethylamine was added dropwise. After raising the temperature to 120 ° C., the mixture was stirred for 16 hours. After cooling to room temperature, a 10% sodium acetate aqueous solution and ethyl acetate were added, and then the organic layer was separated and concentrated under reduced pressure. It was purified by silica gel chromatography to obtain [1]. (8.58 g, 14.9%)

MS (MALDI-TOF): m/z 958.49 [M ⁺ ]

synthesis example 2 : [ 2] of synthesis

synthesis example 2-1: Synthesis of B-1

<A-4a> <B-1a> <B-1>

50 g of <A-4a>, 75.4 g of <B-1a>, 0.8 g of palladium acetate, 2.05 g of Xantphos, 25.6 g of sodium tertiary butoxide, and 500 mL of toluene were added to the reactor, followed by refluxing and stirring for 6 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. Purification was performed by silica gel chromatography to obtain <B-1>. (55 g, 71.0%)

synthesis example 2-2: Synthesis of B-2

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

<B-1> 55 g, <A-2a> 20.6 g, tris(dibenzylideneacetone)dipalladium(0) 2.3 g, sodium tertiary butoxide 24.2 g, bis(diphenylphosphino)-1 After adding 1.5 g of 1'-binaphthyl and 550 mL of toluene, the mixture was refluxed and stirred for 6 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. Purification was performed by silica gel chromatography to obtain <B-2>. (46.8 g, 84.7%)

synthesis example 2-3: Synthesis of B-3

<A-3> <B-2> <B-3>

<B-3> was obtained in the same manner as in Synthesis Example 1-4, using <B-2> instead of <A-4a>. (Yield 98%)

synthesis example 2-4: [ 2] of synthesis

<B-3> [2]

[2] was obtained in the same manner as in Synthesis Example 1-5, using <B-3> instead of <A-4>. (Yield 13.1%)

MS (MALDI-TOF): m/z 1181.62 [M ⁺ ]

synthesis example 3: [ 6] of synthesis

synthesis example 3-1: Synthesis of C-1

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

<C-1> was obtained in the same manner as in Synthesis Example 2-2, using <C-1a> instead of <B-1>. (Yield 85.1%)

synthesis example 3-2: Synthesis of C-2

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

<C-2> was obtained in the same manner as in Synthesis Example 2-1, using <C-1> instead of <A-4a>. (Yield 46.2%)

synthesis example 3-3: Synthesis of C-3

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

In Synthesis Example 2-2, <C-2> was used instead of <B-1>, and <C-3a> was used instead of <A-2a> to obtain <C-3> in the same manner. (Yield 89.4%)

synthesis example 3-4: Synthesis of C-4

<A-3> <C-3> <C-4>

<C-4> was obtained in the same manner as in Synthesis Example 1-4, using <C-3> instead of <A-4a>. (Yield 98.9%)

synthesis example 3-5: [ 6] of synthesis

<C-4> [6]

[6] was obtained in the same manner as in Synthesis Example 1-5, using <C-4> instead of <A-4>. (Yield 13.8%)

MS (MALDI-TOF): m/z 1277.62 [M ⁺ ]

synthesis example 4 : [ 18] synthesis

synthesis example 4-1: Synthesis of D-1

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

<D-1> was obtained in the same manner as in Synthesis Example 2-3, using <D-1a> instead of <A-3>. (Yield 95.3%)

synthesis example 4-2: [ 18] synthesis

<D-1> [18]

[18] was obtained in the same manner as in Synthesis Example 1-5, using <D-1> instead of <A-4>. (Yield 12.4%)

MS (MALDI-TOF): m/z 1161.66 [M ⁺ ]

synthesis example 5: [ 21] synthesis

synthesis example 5-1: Synthesis of E-1

<E-1a> <E-1b> <E-1>

After putting 50 g of <E-1b> and 250 mL of tetrahydrofuran into the reactor, 98.5 mL of a 1.6 M n-butyllithium solution was added dropwise at -78 °C. After stirring at -78 °C for 2 hours, <E-1a> was dissolved in 250 mL of tetrahydrofuran and slowly added thereto, followed by raising the temperature to room temperature and stirring for 16 hours. After adding ethyl acetate and water, the organic layer was separated. It was purified by silica gel chromatography to obtain <E-1>. (46.8 g, 72.6%)

synthesis example 5-2: Synthesis of E-2

<E-1> <E-2>

<E-2> was obtained in the same manner as in Synthesis Example 1-1, using <E-1> instead of <A-1a>. (Yield 68.4%)

synthesis example 5-3: Synthesis of E-3

<E-2> <C-3a> <E-3>

In Synthesis Example 1-2, <E-2> was used instead of <A-1>, and <C-3a> was used instead of <A-2a> to obtain <E-3> in the same manner. (Yield 52.3%)

synthesis example 5-4: Synthesis of E-4

<E-3> <B-2> <E-4>

<E-4> was obtained in the same manner as in Synthesis Example 2-3, using <E-3> instead of <A-3>. (Yield 97.7%)

synthesis example 5-5: [ 21] synthesis

<E-4> [21]

[21] was obtained in the same manner as in Synthesis Example 1-5, using <E-4> instead of <A-4>. (Yield 10.5%)

MS (MALDI-TOF): m/z 1217.72 [M ⁺ ]

synthesis example 6: [ 27] synthesis

synthesis example 6-1: Synthesis of F-1

<C-2> <F-1a> <F-1>

<F-1> was obtained in the same manner as in Synthesis Example 3-3, using <F-1a> instead of <C-3a>. (Yield 90.4%)

synthesis example 6-2: Synthesis of F-2

<A-3> <F-1> <F-2>

<F-2> was obtained in the same manner as in Synthesis Example 1-4, using <F-1> instead of <A-4a>. (Yield 95.2%)

synthesis example 6-3: [ 27] synthesis

<F-2> [27]

[27] was obtained in the same manner as in Synthesis Example 1-5, using <F-2> instead of <A-4>. (Yield 10.5%)

MS (MALDI-TOF): m/z 1235.54 [M ⁺ ]

synthesis example 7: [ 31] synthesis

synthesis example 7-1: Synthesis of G-1

<B-1> <G-1a> <G-1>

<G-1> was obtained in the same manner as in Synthesis Example 2-2, using <G-1a> instead of <A-2a>. (Yield 82.7%)

synthesis example 7-2: Synthesis of G-2

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

<G-2> was obtained in the same manner as in Synthesis Example 1-2, using <G-2a> instead of <A-2a>. (Yield 86.2%)

synthesis example 7-3: Synthesis of G-3

<G-2> <A-3a> <G-3>

<G-3> was obtained in the same manner as in Synthesis Example 1-3, using <G-2> instead of <A-2>. (Yield 94.7%)

synthesis example 7-4: Synthesis of G-4

<G-3> <G-1> <G-4>

In Synthesis Example 1-4, <G-3> was used instead of <A-3>, and <G-1> was used instead of <A-4a> to obtain <G-4> in the same manner. (Yield 87.6%)

synthesis example 7-5: [ 31] synthesis

<G-4> [31]

[31] was obtained in the same manner as in Synthesis Example 1-5, using <G-4> instead of <A-4>. (Yield 11.6%)

MS (MALDI-TOF): m/z 1159.51 [M ⁺ ]

synthesis example 8 : [ 32] synthesis

synthesis example 8-1: Synthesis of H-1

<C-1a> <G-1a> <H-1>

<H-1> was obtained in the same manner as in Synthesis Example 3-1, using <G-1a> instead of <A-2a>. (Yield 86.2%)

synthesis example 8-2: Synthesis of H-2

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

<H-2> was obtained in the same manner as in Synthesis Example 2-1, using <H-1> instead of <A-4a>. (Yield 49.3%)

synthesis example 8-3: Synthesis of H-3

<H-2> <H-3a> <H-3>

In Synthesis Example 2-2, <H-2> was used instead of <B-1>, and <H-3a> was used instead of <A-2a> to obtain <H-3> in the same manner. (Yield 87.8%)

synthesis example 8-4: Synthesis of H-4

<A-3> <H-3> <H-4>

<H-4> was obtained in the same manner as in Synthesis Example 1-4, using <H-3> instead of <A-4a>. (Yield 91.1%)

synthesis example 8-5: [ 32] synthesis

<H-4> [32]

[32] was obtained in the same manner as in Synthesis Example 1-5, using <H-4> instead of <A-4>. (Yield 12.1%)

MS (MALDI-TOF): m/z 1195.46 [M ⁺ ]

synthesis example 9: [ 33] synthesis

synthesis example 9-1: Synthesis of I-1

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

<I-1> was obtained in the same manner as in Synthesis Example 1-3, using <I-1a> instead of <A-3a>. (Yield 96.8%)

synthesis example 9-2: Synthesis of I-2

<I-1> <F-1> <I-2>

<I-2> was obtained in the same manner as in Synthesis Example 6-2, using <I-1> instead of <A-3>. (Yield 94.1%)

synthesis example 9-3: [ 33] synthesis

<I-2> [33]

[33] was obtained in the same manner as in Synthesis Example 1-5, using <I-2> instead of <A-4>. (Yield 12.1%)

MS (MALDI-TOF): m/z 1204.48 [M ⁺ ]

Example 1 to 4: Manufacture of organic light emitting device

After the ITO glass was patterned so that the light emitting area had a size of 2 mm × 2 mm, it was washed. After the ITO glass is mounted in a vacuum chamber, and the base pressure is 1 × 10 ^-7 torr, as a hole injection layer on the ITO, the deposition ratio of [Acceptor-1] electron acceptor and [Formula F] is [ Acceptor-1]: [Formula F] = 2: 98 to form a film (100 Å). [Formula F] was formed as a hole transport layer (550 Å), and then [Formula G] was formed as a film (50 Å) as an electron blocking layer. The light emitting layer is formed by mixing a host [BH-1] according to the present invention described below and a compound (2 wt%) according to [Formula 1] or [Formula 2] of the present invention (200 Å), and then hole [Formula H] is formed as a blocking layer (50 Å), [Formula E-1] and [Formula E-2] are used as an electron transport layer in a ratio of 1: 1 to form 250 Å, and as an electron injection layer [Formula E-2] ] was formed in the order of 10 Å and Al (1000 Å), respectively, to prepare an organic light emitting device. The emission characteristics of the organic light emitting device were measured at 0.4 mA.

[Formula F] [Formula G] [Formula H]

[Formula E-1] [Formula E-2] [Acceptor-1]

[BH-1]

comparative example 1 to 4

An organic light emitting device was manufactured in the same manner except for using the following [BH-2] instead of the host compound [BH-1] in the light emitting layer used in Examples 1 to 4, and the emission characteristics of the organic light emitting device were measured at 0.4 mA did The structure of [BH-2] is as follows.

[BH-2]

division host dopant Voltage (V) Efficiency (EQE, %) Life (T97, hr) Example 1 BH-1 [6] 3.5 10.7 384 Example 2 BH-1 [27] 3.5 11.1 422 Example 3 BH-1 [32] 3.5 10.9 401 Example 4 BH-1 [33] 3.5 11.2 425 Comparative Example 1 BH-2 [6] 3.5 10.3 227 Comparative Example 2 BH-2 [27] 3.5 10.4 243 Comparative Example 3 BH-2 [32] 3.5 10.3 236 Comparative Example 4 BH-2 [33] 3.5 10.6 249

As shown in Examples 1 to 4 of [Table 1], when a boron-containing polycyclic compound according to the present invention is used as a dopant and a derivative compound having an anthracene skeleton is used as a host in the light emitting layer of a device, improved light emitting efficiency and long lifespan An organic light emitting device having characteristics may be implemented.

In addition, compared to Comparative Examples 1 to 4, when deuterium is substituted for anthracene in the anthracene derivative structure, more improved device characteristics can be implemented.

Example 5 to 8: Manufacture of organic light emitting device

An organic light emitting device was manufactured in the same manner except for using the following [BH-3] instead of the host compound [BH-1] in the light emitting layer used in Examples 1 to 4, and the emission characteristics of the organic light emitting device were measured at 0.4 mA did The structure of [BH-3] is as follows.

[BH-3]

comparative example 5 to 8

An organic light emitting device was manufactured in the same manner except for using the following [BH-4] instead of the host compound [BH-3] in the light emitting layer used in Examples 5 to 8, and the emission characteristics of the organic light emitting device were measured at 0.4 mA did The structure of [BH-4] is as follows.

[BH-4]

division host dopant Voltage (V) Efficiency (EQE, %) Life (T97, hr) Example 5 BH-3 [6] 4.0 10.6 241 Example 6 BH-3 [27] 4.1 10.8 257 Example 7 BH-3 [32] 4.0 10.9 267 Example 8 BH-3 [33] 4.1 11.1 272 Comparative Example 5 BH-4 [6] 4.0 10.5 220 Comparative Example 6 BH-4 [27] 4.0 10.8 234 Comparative Example 7 BH-4 [32] 4.0 10.8 232 Comparative Example 8 BH-4 [33] 4.0 11.0 245

As shown in Examples 5 to 8 of [Table 2], the boron-containing polycyclic compound according to the present invention is used as a dopant and the anthracene derivative compound containing deuterium is used as a host to improve luminous efficiency and Together, it is possible to implement an organic light emitting device having a long lifespan characteristic.

In addition, when compared with Comparative Examples 5 to 8, it can be confirmed that the lifespan characteristics are further improved due to the difference in the presence or absence of deuterium in the structure of the anthracene derivative compound.

As described above, as confirmed in [Table 1] and [Table 2], the device employing the characteristic dopant compound and host compound according to the present invention in the light emitting layer in the organic light emitting device is compared with the characteristic structure of the compound according to the present invention. Thus, a long-life, high-efficiency organic light emitting device with improved light emitting efficiency and excellent lifespan characteristics can be implemented compared to devices employing compounds having differences.

Claims (15)

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 layer includes a light emitting layer including a host and a dopant,
The dopant includes at least one compound represented by [Formula 1] and [Formula 2], and the host is an organic light emitting device that is an anthracene compound represented by [Formula 3]:
[Formula 1] [Formula 2]

In [Formula 1] and [Formula 2],
X is B, P = O, P = S or Al,
Y ₁ and Y ₂ are each independently NR ₁ , O, S, CR ₂ R ₃ or SiR ₄ R ₅ ;
Y ₃ is O or S;
A ₁ to A ₃ are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 5 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 50 carbon atoms, a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms, and Any one selected from substituted or unsubstituted aliphatic aromatic mixed rings having 3 to 30 carbon atoms,
R and R ₁ to R ₅ are the same as or different from each other, and each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, 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 heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, Substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted 5 to 30 carbon atoms Any one selected from an arylthioxy group, 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 ego,
However, except that the plurality of R's consist of only substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
The R ₁ to R ₅ may be connected to the A ₁ to A ₃ rings to further form an alicyclic or aromatic monocyclic or polycyclic ring,
The plurality of Rs may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
R ₂ and R ₃ and R ₄ and R ₅ may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring;

[Formula 3]

In the above [Formula 3],
R ₁₁ to R ₁₈ are the same as or different from each other, and each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted Aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted Or an 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 alkylthio group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkylthio group having 5 to 30 carbon atoms. It is any one selected from an arylthioxy group, 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. ,
However, at least one or more of R ₁₁ to R ₁₈ is deuterium,
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 are each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted 3 carbon atoms. to 30 heterocycloalkyl groups, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, and substituted or unsubstituted aliphatic aromatic mixed ring groups having 3 to 30 carbon atoms;
D _n means the number of hydrogens in Ar ₁ to Ar ₄ replaced with deuterium,
n is an integer from 0 to 50; According to claim 1,
The [Formula 1] is represented by the following [Formula 1-1], and the [Formula 2] is an organic light emitting device represented by the following [Formula 2-1]:
[Formula 1-1] [Formula 2-1]

In [Formula 1-1] and [Formula 2-1], the definitions of A ₁ , A ₂ , X, Y ₁ to Y ₃ and R are the same as defined in [Formula 1] and [Formula 2]. According to claim 2,
In [Formula 1] or [Formula 2], X is B (boron), and at least one of the plurality of R is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. According to claim 1,
In [Formula 1] or [Formula 2], the substituent of A ₂ is a substituted or unsubstituted amine group organic light-emitting device. According to claim 1,
In [Formula 1] or [Formula 2], at least one of Y ₁ and Y ₂ is NR ₁ , and R ₁ is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, an organic light-emitting device. According to claim 4,
wherein the substituted or unsubstituted amine group is a substituted or unsubstituted diarylamine group. According to claim 6,
At least one of the aryl groups of the diarylamine group is a substituted or unsubstituted phenyl group. According to claim 7,
The organic light emitting device of claim 1 , wherein the phenyl group is a phenyl group in which an aryl group having 6 to 20 carbon atoms is substituted at an ortho position. According to claim 1,
At least one of the hydrogens of each compound represented by [Formula 1] or [Formula 2] is an organic light emitting device in which deuterium is substituted. According to claim 1,
At least 4 of R ₁₁ to R ₁₈ in [Formula 3] are deuterium organic light emitting devices. According to claim 1,
The organic light emitting device wherein the compound represented by [Formula 1] or [Formula 2] is any one selected from the following [1] to [102]:

According to claim 1,
The compound represented by [Formula 3] is any one organic light emitting device selected from the group consisting of the following compounds:

According to claim 1,
The organic light emitting device, characterized in that the host of the light emitting layer is used by mixing or stacking one or more compounds in addition to one compound represented by [Chemical Formula 3]. According to claim 1,
An organic light emitting device, characterized in that the dopant in the light emitting layer is used in a mixture or stacking of one or more compounds in addition to one compound represented by [Formula 1] or [Formula 2]. According to claim 1,
The organic light emitting diode may include a flat panel display device; flexible display devices; devices for monochromatic or white flat lighting; devices for flexible lighting in monochromatic or white; vehicle display devices; And a display device for virtual or augmented reality; organic light emitting device used in any one device selected from.