KR20210054456A - Organic light emitting device - Google Patents

Abstract

The present invention provides an organic light emitting device having increased driving voltage, efficiency, and lifetime. The organic light emitting device comprises an anode, a hole transport layer, an electronic blocking layer, a light emitting layer, an electron transport layer, and a cathode.

Description

Organic light emitting device TECHNICAL FIELD

The present invention relates to an organic light-emitting device having improved driving voltage, efficiency, and lifetime.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.

An organic light-emitting device generally has a structure including an anode and a cathode, and an organic material layer between the anode and the cathode. The organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows.

In the organic light-emitting device as described above, development of an organic light-emitting device with improved driving voltage, efficiency, and life is continuously required.

Korean Patent Publication No. 10-2000-0051826

The present invention relates to an organic light-emitting device having improved driving voltage, efficiency, and lifetime.

The present invention provides the following organic light emitting device:

anode,

Hole transport layer,

Electron blocking layer,

Light emitting layer,

An electron transport layer, and

Including a cathode,

The electron blocking layer includes a compound represented by Formula 1 below,

The emission layer includes a compound represented by the following formula (2),

The electron transport layer comprises a compound represented by the following formula (3),

Organic Light-Emitting Element:

[Formula 1]

In Formula 1,

L ₁₁ and L ₁₂ are each independently a single bond; Or a substituted or unsubstituted C _6-60 arylene,

Ar ₁₁ and Ar ₁₂ are each independently a substituted or unsubstituted C _6-60 aryl,

Each R ₁ is independently hydrogen or deuterium; Or two adjacent _{to form a C 6-60} aromatic ring,

n1 is each independently an integer of 1 to 4,

[Formula 2]

In Chemical Formula 2,

Ar ₂₁ and Ar ₂₂ are each independently a substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl including any one or more selected from the group consisting of N, O and S,

Each R ₂ is independently hydrogen; heavy hydrogen; Or substituted or unsubstituted C _6-60 aryl,

n2 is each independently an integer of 1 to 4,

[Formula 3]

In Chemical Formula 3,

Ar ₃₁ and Ar ₃₂ are each independently substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl including any one or more selected from the group consisting of N, O and S,

L ₃₁ and L ₃₂ are each independently a single bond; Or a substituted or unsubstituted C _6-60 arylene,

Ar ₃₃ is substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl including any one or more selected from the group consisting of N, O and S,

L ₃₃ is a single bond; Or a substituted or unsubstituted C _6-60 arylene,

Each R ₃ is independently hydrogen or deuterium,

n3 is an integer of 1 to 4.

The above-described organic light emitting device is excellent in driving voltage, efficiency, and lifetime.

1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, an electron blocking layer 4, a light emitting layer 5, an electron transport layer 6, and a cathode 7 It is shown.
2 shows a substrate 1, an anode 2, a hole injection layer 8, a hole transport layer 3, an electron blocking layer 4, a light emitting layer 5, a hole blocking layer 9, and an electron transport layer 6 ) And a cathode 7 are shown.

Hereinafter, it will be described in more detail to aid the understanding of the present invention.

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

Means a bond connected to another substituent.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more of N, O, and S atoms, or substituted or unsubstituted with two or more substituents connected among the aforementioned substituents. . For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent to which two phenyl groups are connected.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with a C1-C25 linear, branched or cyclic alkyl group or an aryl group having 6 to 25 carbon atoms in the oxygen of the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cycloheptylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

Can be, etc. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine 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, phenanthroline group, isoxazolyl group, thiiadia There are a zolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

In the present specification, the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group. In the present specification, for heteroaryl among heteroarylamines, the description of the aforementioned heterocyclic group may be applied. In the present specification, the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents. In the present specification, the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are bonded to each other and formed.

Hereinafter, the present invention will be described in detail for each configuration.

Anode and cathode

An anode and a cathode used in the present invention mean an electrode used in an organic light-emitting device.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO _{2 :Sb;} Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multilayered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

Hole injection layer

The organic light-emitting device according to the present invention may further include a hole injection layer between the anode and the hole transport layer, if necessary.

The hole injection layer is a layer that injects holes from the electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and is generated from the light emitting layer. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.

Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

Hole transport layer

The organic light-emitting device according to the present invention may further include a hole transport layer between the electron blocking layer and the anode.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.As a hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility for holes This is suitable.

Specific examples of the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion.

Electron blocking layer

The organic light emitting device according to the present invention includes an electron blocking layer between the hole transport layer and the light emitting layer. Preferably, the electron blocking layer is in contact with the light emitting layer.

The electron blocking layer serves to improve the efficiency of the organic light-emitting device by inhibiting transfer of electrons injected from the cathode to the anode without recombining in the emission layer. In the present invention, a compound represented by Formula 1 is used as a material constituting the electron blocking layer.

Preferably, the formula 1 is represented by the following formulas 1-1, 1-2 or 1-3:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

Was in the formula 1-1, 1-2 and 1-3, with the exception of the R _'1 and n' ₁ is as defined above in formula 1, R _'1 is hydrogen or deuterium, n' is from 1 to ₁ It is an integer of 6.

Preferably, L ₁₁ and L ₁₂ are each independently a single bond, phenylene, or dimethylfluorenylene.

Preferably, Ar ₁₁ and Ar ₁₂ are each independently, phenyl, biphenylyl, terphenylyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, naphthyl, phenylnaphthyl, naphthyl Phenyl, anthracenyl, or triphenylenyl; Each of Ar ₁₁ and Ar ₁₂ is independently unsubstituted or substituted with a substituent selected from the group consisting of deuterium, halogen, cyano, and Si(C _{1-4 alkyl).} At this time, the meaning of being substituted with deuterium means that at least one of the replaceable hydrogens present in each substituent is substituted with deuterium.

Preferably _{, at least one of Ar 11} and Ar ₁₂ is phenyl, biphenylyl, phenylnaphthyl or naphthylphenyl.

Representative examples of the compound represented by Formula 1 are as follows:

In addition, the present invention provides a method for preparing a compound represented by Chemical Formula 1, such as the following Scheme 1.

[Scheme 1]

In Reaction Scheme 1, the definitions other than X'are as defined above, and X'is halogen, preferably bromo or chloro. The reaction is an amine substitution reaction, and is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction may be changed as known in the art. The manufacturing method may be more specific in the manufacturing examples to be described later.

Light emitting layer

The light emitting layer used in the present invention refers to a layer capable of emitting light in a visible light region by combining holes and electrons transmitted from an anode and a cathode. In general, the light emitting layer includes a host material and a dopant material, and in the present invention, the compound represented by Formula 2 is included as a host.

Preferably, Ar ₂₁ and Ar ₂₂ are each independently phenyl, biphenylyl, naphthyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, (phenyl)dibenzofuranyl, or benzonaphthofuranyl. , Ar ₂₁ and Ar ₂₂ are unsubstituted or substituted with one or more deuterium. At this time, the meaning of being substituted with deuterium means that at least one of the replaceable hydrogens present in each substituent is substituted with deuterium.

Preferably, R ₂ is hydrogen, deuterium, phenyl, phenyl substituted with 1 to 5 deuterium, naphthyl or naphthyl substituted with 1 to 7 deuterium.

Preferably _{, one of R 2} is phenyl, phenyl substituted with 1 to 5 deuterium, naphthyl or naphthyl substituted with 1 to 7 deuterium, the other being hydrogen or deuterium.

Representative examples of the compound represented by Formula 2 are as follows:

In addition, the present invention provides a method for preparing a compound represented by Chemical Formula 2, such as the following Scheme 2.

[Scheme 2]

In Reaction Scheme 2, the definitions other than X'are as defined above, and X'is halogen, preferably bromo or chloro. The first step of the reaction is a step of sequentially reacting with each aryl halide compound using an anthraquinone compound as a starting material, and when Ar ₂₁ and Ar ₂₂ are the same, it may proceed in one reaction. The second step of the reaction is a step of preparing an anthracene-based compound, which may be prepared by refluxing potassium iodide and sodium hypophosphite in acetic acid. The manufacturing method may be more specific in the manufacturing examples to be described later.

Meanwhile, the dopant material is not particularly limited as long as it is a material used in an organic light-emitting device. Examples include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamino group, and the styrylamine compound is substituted or unsubstituted As a compound in which at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto. In addition, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

Hole blocking layer

The organic light-emitting device according to the present invention includes a hole blocking layer between the light-emitting layer and the electron transport layer, if necessary. Preferably, the hole blocking layer is in contact with the light emitting layer.

The hole blocking layer serves to improve the efficiency of the organic light-emitting device by inhibiting the holes injected from the anode from being transferred to the cathode without being recombined in the emission layer. Specific examples of materials that can be used as the material for the hole blocking layer include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

Electron transport layer

The organic light emitting device according to the present invention may include an electron transport layer between the light emitting layer (or hole blocking layer) and the cathode.

The electron transport layer is a layer that receives electrons from the electron injection layer formed on the cathode or the cathode, transports electrons to the emission layer, and inhibits the transfer of holes from the emission layer. As an electron transport material, electrons are well injected from the cathode. As a material that can be received and transferred to the emission layer, the compound represented by Chemical Formula 3 is used in the present invention.

Preferably, the formula 3 is represented by the following formulas 3-1, 3-2, 3-3, 3-4 or 3-5.

[Chemical Formula 3-1]

[Chemical Formula 3-2]

[Chemical Formula 3-3]

[Chemical Formula 3-4]

[Formula 3-5]

Preferably, Ar ₃₁ and Ar ₃₂ are each independently phenyl, biphenylyl, naphthylphenyl, phenylnaphthyl, or pyridinylphenyl, and Ar ₃₁ and Ar ₃₂ are unsubstituted or one or more deuterium, It is substituted with cyano, or C _{1-10 alkyl.}

Preferably, L ₃₁ and L ₃₂ are each independently a single bond, or phenylene.

Preferably, Ar ₃₃ is phenyl, biphenylyl, dimethylfluorenyl, naphthyl, triphenylenyl, fluoranthenyl, diphenylfluorenyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl , Imidazolyl, furanyl, pyridazinyl, dibenzofuranyl, carbazol-9-yl; Ar ₃₃ is unsubstituted or substituted with one or more cyano, C _1-10 alkyl, or C _6-20 aryl.

Preferably, L ₃₃ is a single bond, phenylene, furandiyl, or pyridinylene.

Preferably, R ₃ is hydrogen, deuterium, or phenyl.

Representative examples of the compound represented by Formula 3 are as follows:

In addition, the present invention provides a method for preparing a compound represented by Chemical Formula 3, such as the following Scheme 3.

[Scheme 3]

The reaction is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed as known in the art. The manufacturing method may be more specific in the manufacturing examples to be described later.

In addition, the electron transport layer may further include a metal complex compound. Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

Electron injection layer

The organic light-emitting device according to the present invention may further include an electron injection layer between the electron transport layer and the cathode, if necessary.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer It is preferable to use a compound that prevents migration to the layer and is excellent in thin film forming ability.

Specific examples of materials that can be used as the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preore And derivatives thereof such as nilidene methane, anthrone, and the like, metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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

Organic light emitting element

The structure of the organic light emitting device according to the present invention is illustrated in FIG. 1. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, an electron blocking layer 4, a light emitting layer 5, an electron transport layer 6, and a cathode 7 It is shown. In addition, FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 8, a hole transport layer 3, an electron blocking layer 4, a light emitting layer 5, a hole blocking layer 9, and an electron transport layer. An example of an organic light-emitting device comprising (6) and a cathode (7) is shown.

The organic light emitting device according to the present invention can be manufactured by sequentially stacking the above-described configurations. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate. And, after forming each of the above-described layers thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material on a substrate to an anode material in the reverse order of the above-described configuration (WO 2003/012890). In addition, the light emitting layer may be formed by a solution coating method as well as a vacuum deposition method of a host and a dopant. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

Meanwhile, the organic light-emitting device according to the present invention may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

Hereinafter, a preferred embodiment is presented to aid the understanding of the present invention. However, the following examples are provided for easier understanding of the present invention, and the contents of the present invention are not limited thereto.

[Production Example]

Preparation Example 1-1: Preparation of compound EBL-1

Compound 1-1' (14.34 g, 29.51 mmol) and compound 1-1" (8.29g, 26.83 mmol) were completely dissolved in tetrahydrofuran (240 mL) in a 500 mL round bottom flask in a nitrogen atmosphere, and then 2 M potassium carbonate. An aqueous solution (120 mL) was added, and Pd(t-Bu ₃ P) ₂ (0.25 g, 0.49 mmol) was added, followed by heating and stirring for 5 hours, the temperature was lowered to room temperature, the water layer was removed, and dried over anhydrous magnesium sulfate. Then, it was concentrated under reduced pressure and recrystallized with ethyl acetate (370 mL) to prepare compound EBL-1 (11.69 g, yield: 61%).

MS[M+H] ⁺ = 715

Preparation Example 1-2: Preparation of compound EBL-2

Compound 1-2' (8.61 g, 20.95 mmol) and compound 1-2" (7.56 g, 19.04 mmol) were completely dissolved in tetrahydrofuran (240 mL) in a 500 mL round bottom flask in a nitrogen atmosphere, and then 2 M potassium carbonate An aqueous solution (120 mL) was added, and Pd(t-Bu ₃ P) ₂ (0.19 g, 0.38 mmol) was added, followed by heating and stirring for 5 hours. Then, it was concentrated under reduced pressure and recrystallized with ethyl acetate (350 mL) to prepare compound EBL-2 (10.88 g, yield: 71%).

MS[M+H] ⁺ = 803

Preparation Example 1-3: Preparation of compound EBL-3

Compound 1-3' (5.78 g, 17.95 mmol) and compound 1-3" (9.60 g, 20.64 mmol) were completely dissolved in tetrahydrofuran (240 mL) in a 500 mL round bottom flask in a nitrogen atmosphere, and then 2 M potassium carbonate An aqueous solution (120 mL) was added, tetrakis-(triphenylphosphine)palladium (0.62 g, 0.54 mmol) was added, followed by heating and stirring for 5 hours, the temperature was lowered to room temperature, the water layer was removed, and anhydrous magnesium sulfate was used. After drying, it was concentrated under reduced pressure and recrystallized with ethyl acetate (350 mL) to prepare compound EBL-3 (7.78 g, yield: 65%).

MS[M+H] ⁺ = 663

Preparation Example 1-4: Preparation of compound EBL-4

Compound 1-4' (6.11 g, 18.98 mmol) and compound 1-4" (12.37 g, 21.82 mmol) were completely dissolved in tetrahydrofuran (240 mL) in a 500 mL round bottom flask in a nitrogen atmosphere, and then 2 M potassium carbonate. An aqueous solution (120 mL) was added, tetrakis-(triphenylphosphine)palladium (0.66 g, 0.57 mmol) was added, followed by heating and stirring for 4 hours, the temperature was lowered to room temperature, the water layer was removed, and anhydrous magnesium sulfate was used. After drying, it was concentrated under reduced pressure and recrystallized with ethyl acetate (350 mL) to prepare compound EBL-4 (8.95 g, yield: 62%).

MS[M+H] ⁺ = 765

Preparation Example 1-5: Preparation of compound EBL-5

Compound 1-5' (6.53 g, 20.28 mmol) and compound 1-5" (12.66 g, 23.32 mmol) were completely dissolved in tetrahydrofuran (240 mL) in a 500 mL round bottom flask in a nitrogen atmosphere, and then 2 M potassium carbonate. An aqueous solution (120 mL) was added, tetrakis-(triphenylphosphine)palladium (0.70 g, 0.61 mmol) was added, followed by heating and stirring for 3 hours, the temperature was lowered to room temperature, the water layer was removed, and anhydrous magnesium sulfate was used. After drying, it was concentrated under reduced pressure and recrystallized with ethyl acetate (280 mL) to prepare compound EBL-5 (9.98 g, yield: 67%).

MS[M+H] ⁺ = 739

Preparation Example 2-1: Preparation of compound HOST-1

After dissolving phenyl bromide (1 eq) in tetrahydrofuran under a nitrogen atmosphere, n-BuLi (1.1 eq) was slowly added dropwise at -78°C. After 30 minutes 2-naphthylanthraquinone (1 eq) was added. After raising the temperature to room temperature, when the reaction was terminated, extraction was performed with ethyl acetate and washed with water. The above and the method were carried out once more using phenyl bromide. After completion of the reaction, extraction was performed with ethyl acetate and washed with water. All ethyl acetate was evaporated and precipitated with hexane to obtain 2-naphthalene-9,10-phenyl-9,10-dihydroanthracene-9,10-diol in 50% yield as a solid.

2-Naphthalene-9,10-phenyl-9,10-dihydroanthracene-9,10-diol (1 eq), KI (3 eq), and NaPO ₂ H ₂ (5 eq) were added to acetic acid and the temperature was set at 120 It was raised to °C and refluxed. After the reaction was completed, an excess of water was poured to filter the resulting solid. Dissolved in ethyl acetate, extracted, washed with water, and recrystallized with toluene to obtain compound HOST-1 in a yield of 70%.

MS[M+H] ⁺ = 456.5

Preparation Example 2-2: Preparation of compound HOST-2

Add 9-(naphthalen-1-yl)-10-(naphthalen-2-yl)anthracene (20 g), and trifluoromethanesulfonic acid (2 g) to C ₆ D ₆ (500 mL) and 2 at 70°C. Stir for hours. After completion of the reaction, D ₂ O (60 mL) was added and stirred for 30 minutes, and then trimethylamine (6 mL) was added dropwise. The reaction solution was transferred to a separatory funnel, and extracted with water and toluene. The extract _{was dried over MgSO 4} and then recrystallized with ethyl acetate to obtain compound HOST-2 in a yield of 64%.

MS[M+H] ⁺ = 448 ~ 452

Preparation Example 2-3: Preparation of compound HOST-3

2-chloroanthraquinone (20 g), and trifluoromethanesulfonic acid (2 g) were added to C ₆ D ₆ (500 mL) and stirred at 70° C. for 2 hours. After completion of the reaction, D ₂ O (60 mL) was added and stirred for 30 minutes, and then trimethylamine (6 mL) was added dropwise. The reaction solution was transferred to a separatory funnel, and extracted with water and toluene. The extract _{was dried over MgSO 4} and then recrystallized with ethyl acetate to give 2-chloroanthraquinone-d7 (yield: 44%).

MS[M+H] ⁺ = 250.7

2-Chloroanthraquinone-d7 (10 g) and 1-naphthaleneboronic acid (7.6 g) were added to a round bottom flask and dissolved in dioxane (500 mL). K ₂ CO ₃ (20 g) was dissolved in distilled water (30 mL) and added, and bis (tri-tert-butylphosphine) palladium (0) (40 mg) was added. Refluxed for 2 hours, cooled, and filtered. The filtered solid was recrystallized from toluene to obtain 2-(naphthalen-1-yl)anthracene-9,10-dione-d7 (yield: 78%).

MS[M+H] ⁺ = 342.4

After dissolving 2-naphthyl bromide (1 eq) in tetrahydrofuran under a nitrogen atmosphere, n-BuLi (1.1 eq) was slowly added dropwise at -78°C. After 30 minutes 2-(naphthalen-1-yl)anthracene-9,10-dione-d7 (1 eq) was added. After raising the temperature to room temperature, when the reaction was terminated, extraction was performed with ethyl acetate and washed with water. The method was carried out once more using 2-naphthyl bromide. After completion of the reaction, extraction was performed with ethyl acetate and washed with water. All ethyl acetate was evaporated and precipitated with hexane to obtain a solid, and the next reaction proceeded immediately without purification.

The previously obtained compound (1 eq), KI (3 eq), and NaPO ₂ H ₂ (5 eq) were added to acetic acid, and the temperature was raised to 120° C. and refluxed. After the reaction was completed, an excess of water was poured to filter the resulting solid. Dissolved in ethyl acetate, extracted, washed with water, and recrystallized with toluene to obtain compound HOST-3 (yield: 70%).

MS[M+H] ⁺ = 564.7

Preparation Example 2-4: Preparation of compound HOST-4

In a nitrogen atmosphere, 1-(10-bromoanthracene-9-yl)-7-chlorodibenzofuran (20 g, 43.7 mmol) and phenylboronic acid-d5 (11.0 g, 87.4 mmol) were added to dioxane (400 mL). Then, it was stirred and refluxed. Thereafter, the third potassium phosphate (27.8 g, 131.1 mmol) was dissolved in water (28 mL) and added thereto, and after sufficiently stirring, dibenzylideneacetonepalladium (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.7 g, 2.6) mmol) was added. After reacting for 5 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in chloroform (664 mL), washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized in chloroform and ethyl acetate to prepare a solid compound Host-4 (10 g, yield: 45%) of greenish powder.

MS: [M+H]+ = 507.7

Preparation Example 2-5: Preparation of compound HOST-5

In a nitrogen atmosphere, 9-([1,1'-biphenyl]-3-yl)-10-bromoanthracene (20 g, 48.9 mmol) and naphtho[b]benzofuran-2-ylboronic acid (12.8 g, 48.9 mmol) was added to dioxane (400 mL), stirred and refluxed. Thereafter, the third potassium phosphate (31.1 g, 146.6 mmol) was dissolved in water (31 mL) and added thereto, and after sufficiently stirring, dibenzylideneacetonepalladium (0.8 g, 1.5 mmol) and tricyclohexylphosphine (0.8 g, 2.9 mmol) was added. After reaction for 9 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in chloroform (801 mL), washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized in chloroform and ethyl acetate to prepare a solid compound Host-5 (19.8 g, yield: 74%) as greenish powder.

MS: [M+H]+ = 547.7

Preparation Example 2-6: Preparation of compound HOST-6

2-(10-(naphthalen-2-yl)anthracene-9-yl)dibenzo[b,d]furan (20 g), trifluoromethanesulfonic acid (2 g) was added to C ₆ D ₆ (500 mL). And stirred at 70° C. for 2 hours. After completion of the reaction, D ₂ O (60 mL) was added, stirred for 30 minutes, and trimethylamine (6 mL) was added dropwise. The reaction solution was transferred to a separatory funnel, and extracted with water and toluene. The extract _{was dried over MgSO 4} and recrystallized with ethyl acetate to obtain HOST-6 in a yield of 52%.

cal. m/s: 492.71; exp. m/s (M ⁺ ) 458 ~ 492

Preparation Example 3-1: Preparation of compound ETL-1

After completely dissolving compound 3-1' (20 g, 27.3 mmol) and compound 3-1" (6.1 g, 27.3 mmol) in THF (200 mL), potassium carbonate (11.3 g, 81.8 mmol) was added to water (50 mL). After adding tetrakistriphenyl-phosphinopalladium (0.95 g, 0.818 mmol), the mixture was heated and stirred for 8 hours, the temperature was lowered to room temperature, the reaction was terminated, and the potassium carbonate solution was removed. The white solid was filtered, and the filtered white solid was washed twice with THF and ethyl acetate, respectively, to prepare compound ETL-1 (11.9g, yield 71%).

MS[M+H] ⁺ = 613

Preparation Example 3-2: Preparation of compound ETL-2

Compound ETL-2 was prepared in the same manner as in the preparation method of Compound ETL-1 of Preparation Example 3-1, except that each starting material was used in the above reaction scheme.

MS[M+H] ⁺ = 639

Preparation Example 3-3: Preparation of compound ETL-3

Compound ETL-3 was prepared in the same manner as in the method of preparing compound ETL-1 of Preparation Example 3-1, except that each starting material was used in the above reaction scheme.

MS[M+H] ⁺ = 663

Preparation Example 3-4: Preparation of compound ETL-4

Compound ETL-4 was prepared in the same manner as in the method of preparing compound ETL-1 of Preparation Example 3-1, except that each starting material was as shown in the above reaction formula.

MS[M+H] ⁺ = 712

Preparation Example 3-5: Preparation of compound ETL-5

Compound ETL-5 was prepared in the same manner as in the method of preparing compound ETL-1 of Preparation Example 3-1, except that each starting material was as shown in the above reaction formula.

MS[M+H] ⁺ = 679

Preparation Example 3-6: Preparation of compound ETL-6

In a nitrogen atmosphere, compound 3-6' (20 g, 27.6 mmol) and compound 3-6" (24 g, 55.2 mmol) were added to tetrahydrofuran (400 mL), stirred and refluxed. After that, potassium carbonate (11.4 g) , 82.8 mmol) was dissolved in water (11 mL), stirred sufficiently, tetrakistriphenyl-phosphinopalladium (1 g, 0.8 mmol) was added, reacted for 1 hour, cooled to room temperature, and the organic layer and the aqueous layer were mixed After separation, the organic layer was distilled, dissolved in chloroform (410 mL), washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. Recrystallized from ethyl acetate to prepare a white solid compound ETL-6 (11.9 g, yield: 58%).

MS[M+H] ⁺ = 743

Preparation Example 3-7: Preparation of compound ETL-7

Compound ETL-7 was prepared in the same manner as in the method of preparing compound ETL-1 of Preparation Example 3-1, except that each starting material was as shown in the above reaction formula.

MS[M+H] ⁺ = 653

Preparation Example 3-8: Preparation of compound ETL-8

Compound ETL-8 was prepared in the same manner as in the method of preparing compound ETL-1 of Preparation Example 3-1, except that each starting material was used in the above reaction scheme.

MS[M+H] ⁺ = 763

[Example]

Example 1

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

On the ITO transparent electrode prepared as described above, the following HT1 compound and HI1 compound were vacuum-deposited to a thickness of 100 Å at a weight ratio of 100:6 to form a hole injection layer. On the hole injection layer, the following HI1 compound was vacuum-deposited to a thickness of 1150 Å to form a hole transport layer. On the hole transport layer, the previously prepared EBL-1 compound was vacuum deposited to a thickness of 50 Å to form an electron blocking layer. On the electron blocking layer, the previously prepared HOST-1 compound and the following BD compound were vacuum-deposited to a thickness of 200 Å at a weight ratio of 96:4 to form a light emitting layer. On the emission layer, the following HBL compound was vacuum deposited to a thickness of 50 Å to form a hole blocking layer. On the hole blocking layer, the previously prepared ETL-1 compound and the following LiQ compound were vacuum-deposited to a thickness of 310 Å at a weight ratio of 1:1 to form an electron transport layer. On the electron transport layer, magnesium and silver were deposited to a thickness of 120 Å in a weight ratio of 9:1, and then aluminum having a thickness of 1,000 Å was deposited to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 2 Å/sec, the deposition rate of magnesium was 1 Å/sec, silver (Ag) was 0.1 Å/sec, and aluminum was 2 Å/sec. When the vacuum degree was maintained at 2×10 ^-7 to 5×10 ^-6 torr, an organic light-emitting device was manufactured.

Examples 2 to 17

In Example 1, an organic light-emitting device was manufactured in the same manner as the EBL-1 compound, the HOST-1 compound, and/or the ETL-1 compound, except that the compounds shown in Table 1 were used instead.

Comparative Examples 1 and 2

In Example 1, an organic light-emitting device was manufactured in the same manner as the EBL-1 compound, the HOST-1 compound, and/or the ETL-1 compound, except that the compounds shown in Table 1 were used instead. The EBL' compound, HOST' compound, and ETL' compound described in Table 1 are as follows.

Experimental example

^{When a current of 10 mA/cm 2} was applied to the organic light emitting device prepared in the above Examples and Comparative Examples, the driving voltage, luminous efficiency, and lifetime were measured, and the results are shown in Table 1 below. Life (T95) refers to the time it takes for the initial luminance to decrease to 95%.

Electron blocking layer Light emitting layer
(Host) Electron transport layer Driving voltage
(V) Luminous efficiency
(lm/W) Life (T95)
(hr) Example 1 EBL-1 HOST-1 ETL-1 4.18 5.75 431 Example 2 EBL-2 HOST-1 ETL-1 4.15 5.94 453 Example 3 EBL-1 HOST-2 ETL-1 3.97 5.93 510 Example 4 EBL-1 HOST-1 ETL-2 3.95 6.33 360 Example 5 EBL-3 HOST-1 ETL-1 3.72 6.21 452 Example 6 EBL-4 HOST-1 ETL-1 3.83 6.14 508 Example 7 EBL-5 HOST-1 ETL-1 3.78 6.03 488 Example 8 EBL-1 HOST-1 ETL-3 3.71 6.38 401 Example 9 EBL-1 HOST-1 ETL-4 4.07 5.85 440 Example 10 EBL-1 HOST-1 ETL-5 4.22 5.70 508 Example 11 EBL-1 HOST-1 ETL-6 3.65 6.41 389 Example 12 EBL-1 HOST-1 ETL-7 3.75 6.27 415 Example 13 EBL-1 HOST-1 ETL-8 3.89 6.16 422 Example 14 EBL-1 HOST-3 ETL-1 3.85 5.88 458 Example 15 EBL-1 HOST-4 ETL-1 3.48 6.24 430 Example 16 EBL-1 HOST-5 ELT-1 3.61 6.18 422 Example 17 EBL-1 HOST-6 ETL-1 3.52 6.17 502 Comparative Example 1 EBL' HOST' ETL' 3.69 5.95 306 Comparative Example 2 EBL' HOST' ETL'' 3.87 6.13 290

1: substrate 2: anode
3: hole transport layer 4: electron blocking layer
5: light emitting layer 6: electron transport layer
7: cathode 8: hole injection layer
9: hole blocking layer

Claims (16)

anode,
Hole transport layer,
Electron blocking layer,
Light emitting layer,
An electron transport layer, and
Including a cathode,
The electron blocking layer includes a compound represented by Formula 1 below,
The emission layer includes a compound represented by the following formula (2),
The electron transport layer comprises a compound represented by the following formula (3),
Organic Light-Emitting Element:
[Formula 1]

In Formula 1,
L ₁₁ and L ₁₂ are each independently a single bond; Or a substituted or unsubstituted C _6-60 arylene,
Ar ₁₁ and Ar ₁₂ are each independently a substituted or unsubstituted C _6-60 aryl,
Each R ₁ is independently hydrogen or deuterium; Or two adjacent _{to form a C 6-60} aromatic ring,
n1 is each independently an integer of 1 to 4,
[Formula 2]

In Chemical Formula 2,
Ar ₂₁ and Ar ₂₂ are each independently a substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl including any one or more selected from the group consisting of N, O and S,
Each R ₂ is independently hydrogen; heavy hydrogen; Or substituted or unsubstituted C _6-60 aryl,
n2 is each independently an integer of 1 to 4,
[Formula 3]

In Chemical Formula 3,
Ar ₃₁ and Ar ₃₂ are each independently substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl including any one or more selected from the group consisting of N, O and S,
L ₃₁ and L ₃₂ are each independently a single bond; Or a substituted or unsubstituted C _6-60 arylene,
Ar ₃₃ is substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl including any one or more selected from the group consisting of N, O and S,
L ₃₃ is a single bond; Or a substituted or unsubstituted C _6-60 arylene,
Each R ₃ is independently hydrogen or deuterium,
n3 is an integer of 1 to 4.
The method of claim 1,
L ₁₁ and L ₁₂ are each independently a single bond, phenylene, or dimethylfluorenylene,
Organic light emitting device.
The method of claim 1,
Ar ₁₁ and Ar ₁₂ are each independently, phenyl, biphenylyl, terphenylyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, naphthyl, phenylnaphthyl, naphthylphenyl, anthracenyl , Or triphenylenyl,
The Ar ₁₁ and Ar ₁₂ are each independently, unsubstituted or substituted with a substituent selected from the group consisting of deuterium, halogen, cyano, and Si (C _{1-4 alkyl),}
Organic light emitting device.
The method of claim 1,
At least one of Ar ₁₁ and Ar ₁₂ is phenyl, biphenylyl, phenylnaphthyl or naphthylphenyl,
Organic light emitting device.
The method of claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of the following,
Organic Light-Emitting Element:

The method of claim 1,
Ar ₂₁ and Ar ₂₂ are each independently phenyl, biphenylyl, naphthyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, (phenyl) dibenzofuranyl, or benzonaphthofuranyl,
Ar ₂₁ and Ar ₂₂ are unsubstituted or substituted with one or more deuterium,
Organic light emitting device.
The method of claim 1,
R ₂ is hydrogen, deuterium, phenyl, phenyl substituted with 1 to 5 deuterium, naphthyl or naphthyl substituted with 1 to 7 deuterium,
Organic light emitting device.
The method of claim 1,
One of R ₂ is phenyl, phenyl substituted with 1 to 5 deuterium, naphthyl or naphthyl substituted with 1 to 7 deuterium, and the rest is hydrogen or deuterium,
Organic light emitting device.
The method of claim 1,
The compound represented by Formula 2 is any one selected from the group consisting of,
Organic Light-Emitting Element:

The method of claim 1,
Ar ₃₁ and Ar ₃₂ are each independently phenyl, biphenylyl, naphthylphenyl, phenylnaphthyl, or pyridinylphenyl,
Ar ₃₁ and Ar ₃₂ are unsubstituted or substituted with one or more deuterium, cyano, or C _1-10 alkyl,
Organic light emitting device.
The method of claim 1,
L ₃₁ and L ₃₂ are each independently a single bond, or phenylene,
Organic light emitting device.
The method of claim 1,
Ar ₃₃ is phenyl, biphenylyl, dimethylfluorenyl, naphthyl, triphenylenyl, fluoranthenyl, diphenylfluorenyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, imidazolyl , Furanyl, pyridazinyl, dibenzofuranyl, carbazol-9-yl;
Ar ₃₃ is unsubstituted or substituted with one or more cyano, C _1-10 alkyl, or C _6-20 aryl,
Organic light emitting device.
The method of claim 1,
L ₃₃ is a single bond, phenylene, furandiyl, or pyridinylene,
Organic light emitting device.
The method of claim 1,
R ₃ is hydrogen, deuterium, or phenyl,
Organic light emitting device.
The method of claim 1,
The compound represented by Formula 3 is any one selected from the group consisting of,
Organic Light-Emitting Element:

The method of claim 1,
The electron blocking layer is in contact with the light emitting layer,
Organic light emitting device.

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