KR102568228B1 - Organic light emitting device - Google Patents

Abstract

The present invention provides an organic light emitting device with improved driving voltage, efficiency and lifetime.

Description

Organic light emitting device {Organic light emitting device}

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

In general, an organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, and a 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, a cathode, and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of this 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 when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.

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

Korean Patent Publication No. 10-2000-0051826

The present invention relates to an organic light emitting diode 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

contains a cathode,

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

The light emitting layer includes a compound represented by Formula 2 below,

The electron transport layer includes a compound represented by Formula 3 below,

Organic Light-Emitting Elements:

[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;

R ₁ is each independently hydrogen or deuterium; or two adjacent ones combine to form a C _6-60 aromatic ring;

n1 is each independently an integer from 1 to 4;

[Formula 2]

In Formula 2,

Ar ₂₁ and Ar ₂₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or a C _2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S,

R ₂ are each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C _6-60 aryl;

n2 is each independently an integer from 1 to 4;

[Formula 3]

In Formula 3,

Ar ₃₁ and Ar ₃₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or a C _2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted 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 a substituted or unsubstituted C _6-60 aryl; Or a C _2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S,

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

R ₃ is each independently hydrogen or deuterium;

n3 is an integer from 1 to 4;

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

1 shows an example of an organic light emitting device composed of 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 depicted
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, an electron transport layer 6 ) and an example of an organic light emitting device composed of a cathode 7 is shown.

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

In this specification, means a bond connected to another substituent.

In this specification, the term "substituted or unsubstituted" means 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; an alkyl sulfoxy group; aryl sulfoxy groups; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; Aralkenyl group; Alkyl aryl group; Alkylamine group; Aralkylamine group; heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing at least one of N, O, and S atoms, or substituted or unsubstituted with two or more substituents linked to each other among the substituents exemplified above. . For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in 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 an aryl group having 6 to 25 carbon atoms or a straight-chain, branched-chain or cyclic chain alkyl group having 1 to 25 carbon atoms in 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 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 a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. but not limited to

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, but is not limited thereto.

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

In the present specification, the alkyl group may be straight-chain or branched-chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. 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, cyclohexylmethyl, 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, etc., but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one 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, etc., but is 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 number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. 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 preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

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, 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 heterogeneous elements, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, and an acridyl group. , pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl 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, thiadia A zolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

In the present specification, an aralkyl group, an aralkenyl group, an alkylaryl group, and an aryl group among arylamine groups are the same as the examples 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 examples of the above-mentioned alkyl group. In the present specification, the description of the heterocyclic group described above may be applied to the heteroaryl of the heteroarylamine. In the present specification, the alkenyl group among the aralkenyl groups is the same as the examples 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 heterocyclic group described above 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 combining two substituents. In the present specification, the heterocyclic group is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that it is formed by combining two substituents.

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 refer to electrodes used in an organic light emitting device.

As the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic 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; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function so as to easily inject electrons into the organic material layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

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

Specific examples of the hole injection material include metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic matter, anthraquinone, and 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 the holes to the light emitting layer. As a hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer is a material having high hole mobility. this is suitable

Specific examples of the hole transport material include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

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 preventing electrons injected from the cathode from being transferred to the anode without recombination in the light emitting layer. In the present invention, the compound represented by Formula 1 is used as a material constituting the electron blocking layer.

Preferably, Formula 1 is represented by Formula 1-1, 1-2 or 1-3 below:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Chemical Formulas 1-1, 1-2 and 1-3, except for R' ₁ and n' ₁ , the same as defined in Chemical Formula 1 above, R' ₁ is hydrogen or deuterium, and n' ₁ is 1 to 10 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 selected from phenyl, biphenylyl, terphenylyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, naphthyl, phenylnaphthyl, naphthyl phenyl, anthracenyl, or triphenylenyl; 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). At this time, the meaning of being substituted with deuterium means that at least one of the substitutable hydrogen 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 the compound represented by Formula 1, as shown in Reaction Scheme 1 below.

[Scheme 1]

In Reaction Scheme 1, the definitions except for X' are as defined above, and X' is halogen, preferably bromo or chloro. The above 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 can be changed as known in the art. The manufacturing method may be more specific in Preparation Examples to be described later.

light emitting layer

The light emitting layer used in the present invention means a layer capable of emitting light in the visible ray region by combining holes and electrons transferred from the anode and the cathode. In general, the light emitting layer includes a host material and a dopant material, and in the present invention, the compound represented by Chemical 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 atoms. At this time, the meaning of being substituted with deuterium means that at least one of the substitutable hydrogen present in each substituent is substituted with deuterium.

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

Preferably, one of R ₂ is phenyl, phenyl substituted with 1 to 5 deuterium, naphthyl or naphthyl substituted with 1 to 7 deuterium, and the other is 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 the compound represented by Formula 2, as shown in Reaction Scheme 2 below.

[Scheme 2]

In Reaction Scheme 2, the definitions except for 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 an anthraquinone-based compound with each aryl halide compound as a starting material. When Ar ₂₁ and Ar ₂₂ are the same, one reaction may be performed. The second step of the reaction is to prepare an anthracene-based compound, which can be prepared by refluxing potassium iodide and sodium hypophosphite in acetic acid. The manufacturing method may be more specific in Preparation 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. For example, there are aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periplanthene, etc. having an arylamino group, and styrylamine compounds include substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, wherein one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but is not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

hole blocking layer

The organic light emitting device according to the present invention, if necessary, includes a hole blocking layer between the light emitting layer and the electron transport layer. 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 suppressing the transfer of holes injected from the anode to the cathode without recombination in the light emitting layer. Specific examples of materials that can be used as materials 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 cathode or an electron injection layer formed on the cathode, transports electrons to the light emitting layer, and suppresses the transfer of holes in the light emitting layer. As an electron transport material, electrons are well injected from the cathode. As a material that can be transferred to the light emitting layer, the compound represented by Formula 3 is used in the present invention.

Preferably, Chemical Formula 3 is represented by Chemical Formulas 3-1, 3-2, 3-3, 3-4 or 3-5.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[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 at least one deuterium; 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 the compound represented by Formula 3, as shown in Reaction Scheme 3 below.

[Scheme 3]

The above reaction is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and a reactor for the Suzuki coupling reaction can be changed as known in the art. The manufacturing method may be more specific in Preparation 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 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)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. 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 for injecting electrons from an electrode, has the ability to transport electrons, has an excellent electron injection effect from a cathode, an excellent electron injection effect for a light emitting layer or a light emitting material, and injects holes of excitons generated in the light emitting layer. It is preferable to use a compound that prevents migration to a layer and has excellent 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 nylidene methane, anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., 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)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.

organic light emitting device

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 composed of 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 depicted 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, an electron transport layer (6) and an example of an organic light emitting element composed of a cathode (7) is shown.

The organic light emitting device according to the present invention can be manufactured by sequentially stacking the above-described components. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, depositing a metal or a metal oxide having conductivity or an alloy thereof on the substrate to form an anode And, after forming each of the above-described layers thereon, it can be manufactured 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 and an anode material in the reverse order of the above 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 means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

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

Hereinafter, a preferred embodiment is presented to aid understanding of the present invention. However, the following examples are only provided to more easily understand the present invention, and the content of the present invention is not limited thereby.

[Production Example]

Preparation Example 1-1: Preparation of Compound EBL-1

After completely dissolving compound 1-1' (14.34 g, 29.51 mmol) and compound 1-1" (8.29 g, 26.83 mmol) in tetrahydrofuran (240 mL) in a 500 mL round bottom flask under a nitrogen atmosphere, 2 M potassium carbonate Aqueous solution (120 mL) was added, Pd(t-Bu ₃ P) ₂ (0.25 g, 0.49 mmol) was added and heated and stirred for 5 hours.The temperature was lowered to room temperature, the water layer was removed, and dried over anhydrous magnesium sulfate. After concentrating under reduced pressure and recrystallizing with ethyl acetate (370 mL), compound EBL-1 (11.69 g, yield: 61%) was prepared.

MS[M+H] ⁺ = 715

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

After completely dissolving compound 1-2' (8.61 g, 20.95 mmol) and compound 1-2" (7.56 g, 19.04 mmol) in tetrahydrofuran (240 mL) in a 500 mL round bottom flask under a nitrogen atmosphere, 2 M potassium carbonate Aqueous solution (120 mL) was added, and Pd(t-Bu ₃ P) ₂ (0.19 g, 0.38 mmol) was added and heated and stirred for 5 hours.The temperature was lowered to room temperature, the water layer was removed, and dried over anhydrous magnesium sulfate. After concentrating under reduced pressure and recrystallizing with ethyl acetate (350 mL), compound EBL-2 (10.88 g, yield: 71%) was prepared.

MS[M+H] ⁺ = 803

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

After completely dissolving compound 1-3' (5.78 g, 17.95 mmol) and compound 1-3" (9.60 g, 20.64 mmol) in tetrahydrofuran (240 mL) in a 500 mL round bottom flask under a nitrogen atmosphere, 2 M potassium carbonate Aqueous solution (120 mL) was added, tetrakis-(triphenylphosphine)palladium (0.62 g, 0.54 mmol) was added and heated and stirred 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

After completely dissolving compound 1-4' (6.11 g, 18.98 mmol) and compound 1-4" (12.37 g, 21.82 mmol) in tetrahydrofuran (240 mL) in a 500 mL round bottom flask under a nitrogen atmosphere, 2 M potassium carbonate Aqueous solution (120 mL) was added, and 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

After completely dissolving compound 1-5' (6.53 g, 20.28 mmol) and compound 1-5" (12.66 g, 23.32 mmol) in tetrahydrofuran (240 mL) in a 500 mL round bottom flask under a nitrogen atmosphere, 2 M potassium carbonate Aqueous solution (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.70 g, 0.61 mmol) was added and heated and stirred for 3 hours.The temperature was lowered to room temperature, the water layer was removed, and anhydrous magnesium sulfate 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 min 2-naphthylanthraquinone (1 eq) was added. When the reaction was completed after raising the temperature to room temperature, the mixture was extracted with ethyl acetate and washed with water. The above method was performed once more using phenyl bromide. After completion of the reaction, the mixture was extracted with ethyl acetate and washed with water. All ethyl acetate was evaporated and precipitated using hexane to obtain 2-naphthalene-9,10-phenyl-9,10-dihydroanthracene-9,10-diol as a solid in a yield of 50%.

2-naphthalene-9,10-phenyl-9,10-dihydroanthracene-9,10-diol (1 eq), KI (3 eq), and NaPO ₂ H ₂ (5 eq) were put in acetic acid and the temperature was 120 It was raised to °C and refluxed. After completion of the reaction, an excess amount of water was poured and the resulting solid was filtered. 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

9-(naphthalen-1-yl)-10-(naphthalen-2-yl)anthracene (20 g) and trifluoromethanesulfonic acid (2 g) were added to C ₆ D ₆ (500 mL) and stirred at 70 ° C for 2 Stir for an hour. After completion of the reaction, D ₂ O (60 mL) was added, 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. After drying the extract with MgSO ₄ , it was 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, 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. After drying the extract with MgSO ₄ , it was recrystallized with ethyl acetate to obtain 2-chloroanthraquinone-d7 (yield: 44%).

MS[M+H] ⁺ = 250.7

2-Chloroanthraquinone-d7 (10 g) and 1-naphthaleneboronic acid (7.6 g) were placed in a round bottom flask and dissolved in dioxane (500 mL). K ₂ CO ₃ (20 g) dissolved in distilled water (30 mL) was added, and bis(tri-tert-butylphosphine)palladium(0) (40 mg) was added. It was refluxed for 2 hours and filtered after cooling. 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-naphthylbromide (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. When the reaction was completed after raising the temperature to room temperature, the mixture was extracted with ethyl acetate and washed with water. The method was carried out once more using 2-naphthyl bromide. After completion of the reaction, the mixture was extracted with ethyl acetate and washed with water. All ethyl acetate was evaporated and precipitated using hexane to obtain a solid, and the next reaction proceeded without purification.

The previously obtained compound (1 eq), KI (3 eq), and NaPO ₂ H ₂ (5 eq) were put into acetic acid, and the temperature was raised to 120° C. and refluxed. After completion of the reaction, an excess amount of water was poured and the resulting solid was filtered. After dissolving in ethyl acetate, extracting, washing with water, and recrystallizing with toluene, compound HOST-3 was obtained (yield: 70%).

MS[M+H] ⁺ = 564.7

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

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

MS: [M+H]+ = 507.7

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

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, tribasic potassium phosphate (31.1 g, 146.6 mmol) was dissolved in water (31 mL), added, and sufficiently stirred, followed by dibenzylideneacetone palladium (0.8 g, 1.5 mmol) and tricyclohexylphosphine (0.8 g, 2.9 g). mmol) was added. After reacting for 9 hours, cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in chloroform (801 mL), washed twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a greenish powder solid compound Host-5 (19.8 g, yield: 74%).

MS: [M+H]+ = 547.7

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

2-(10-(naphthalen-2-yl)anthracen-9-yl)dibenzo[b,d]furan (20 g), trifluoromethanesulfonic acid (2 g) was added to C ₆ D ₆ (500 mL) Put and stirred for 2 hours at 70 ℃. 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 with 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 to 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), it was heated and stirred for 8 hours. After the reaction was terminated by lowering the temperature to room temperature, the potassium carbonate solution was removed to The white solid was filtered, and the filtered white solid was washed twice each with THF and ethyl acetate to prepare compound ETL-1 (11.9 g, 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 for using each starting material as 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 preparation method of Compound ETL-1 of Preparation Example 3-1, except that each starting material was used as 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 preparation method of compound ETL-1 of Preparation Example 3-1, except that each starting material was used as in the above reaction scheme.

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

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) and stirred and refluxed. Then, potassium carbonate (11.4 g , 82.8 mmol) was dissolved in water (11 mL), stirred sufficiently, and tetrakistriphenyl-phosphinopalladium (1 g, 0.8 mmol) was added. After separation, the organic layer was distilled, dissolved in chloroform (410 mL), washed twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. Recrystallization from ethyl acetate gave 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 preparation method of Compound ETL-1 of Preparation Example 3-1, except that each starting material was prepared as in the above reaction scheme.

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

MS[M+H] ⁺ = 763

[Example]

Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum deposition machine.

A hole injection layer was formed by vacuum depositing the following HT1 compound and HI1 compound at a weight ratio of 100:6 on the ITO transparent electrode prepared as described above to a thickness of 100 Å. 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 at a weight ratio of 96:4 to a thickness of 200 Å to form an emission layer. On the light emitting 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 at a weight ratio of 1:1 to a thickness of 310 Å to form an electron transport layer. On the electron transport layer, magnesium and silver were deposited to a thickness of 120 Å at a weight ratio of 9:1, and then aluminum was deposited to a thickness of 1,000 Å to form a cathode.

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

Examples 2 to 17

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compounds listed in Table 1 were used instead of the EBL-1 compound, the HOST-1 compound, and/or the ETL-1 compound.

Comparative Examples 1 and 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compounds listed in Table 1 were used instead of the EBL-1 compound, the HOST-1 compound, and/or the ETL-1 compound. EBL' compounds, HOST' compounds and ETL' compounds described in Table 1 below are as follows.

Experimental example

When a current of 10 mA/cm ² was applied to the organic light emitting devices prepared in Examples and Comparative Examples, driving voltage, luminous efficiency, and lifetime were measured, and the results are shown in Table 1 below. The lifetime T95 means the time required for the initial luminance to decrease to 95%.

electron blocking layer light emitting layer
(Host) electron transport layer drive 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
contains a cathode,
The electron blocking layer includes a compound represented by Formula 1 below,
The light emitting layer includes a compound represented by Formula 2 below,
The electron transport layer includes a compound represented by Formula 3-1, 3-2 or 3-3,
Organic Light-Emitting Elements:
[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;
R ₁ is each independently hydrogen or deuterium; or two adjacent ones combine to form a C _6-60 aromatic ring;
n1 is each independently an integer from 1 to 4;
[Formula 2]

In Formula 2,
Ar ₂₁ and Ar ₂₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or a C _2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S,
R ₂ are each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C _6-60 aryl;
n2 is each independently an integer from 1 to 4;
[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

In Formulas 3-1, 3-2 and 3-3,
Ar ₃₁ and Ar ₃₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or a C _2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted 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 phenyl, biphenylyl, dimethylfluorenyl, naphthyl, fluoranthenyl, diphenylfluorenyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, imidazolyl, furanyl; pyridazinyl, or dibenzofuranyl;
Ar ₃₃ is unsubstituted or substituted with one or more cyano or C _1-10 alkyl;
L ₃₃ is a single bond, phenylene, furandiyl, or pyridinylene;
R ₃ is each independently hydrogen or deuterium;
n3 is an integer from 1 to 4;
According to claim 1,
L ₁₁ and L ₁₂ are each independently a single bond, phenylene, or dimethylfluorenylene;
organic light emitting device.
According to claim 1,
Ar ₁₁ and Ar ₁₂ are each independently phenyl, biphenylyl, terphenylyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, naphthyl, phenylnaphthyl, naphthylphenyl, anthracenyl , or triphenylenyl;
Wherein 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.
According to claim 1,
At least one of Ar ₁₁ and Ar ₁₂ is phenyl, biphenylyl, phenylnaphthyl or naphthylphenyl;
organic light emitting device.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of
Organic Light-Emitting Elements:

According to 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 groups;
organic light emitting device.
According to claim 1,
R ₂ is hydrogen, deuterium, phenyl, phenyl substituted with 1 to 5 deuterium atoms, naphthyl or naphthyl substituted with 1 to 7 deuterium atoms;
organic light emitting device.
According to claim 1,
one of R ₂ is phenyl, phenyl substituted with 1 to 5 deuterium atoms, naphthyl or naphthyl substituted with 1 to 7 deuterium atoms and the others are hydrogen or deuterium atoms;
organic light emitting device.
According to claim 1,
The compound represented by Formula 2 is any one selected from the group consisting of
Organic Light-Emitting Elements:

According to 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.
According to claim 1,
L ₃₁ and L ₃₂ are each independently a single bond or phenylene;
organic light emitting device.
delete delete According to claim 1,
R ₃ is hydrogen, deuterium, or phenyl;
organic light emitting device.
According to claim 1,
The compound represented by Formula 3-1, 3-2 or 3-3 is any one selected from the group consisting of
Organic Light-Emitting Elements:

.
According to claim 1,
The electron blocking layer is in contact with the light emitting layer,
organic light emitting device.