KR102223482B1 - Compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

A compound and an organic light-emitting device comprising the same TECHNICAL FIELD

The present application relates to a compound and an organic light emitting device including the same.

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 structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multilayer 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.

Development of a new material for the organic light emitting device as described above is continuously required.

Korean Patent Publication No. 10-2016-0033587

The present application is to provide a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

The present application provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

Any one of X1 and Y1 is a direct bond, and the other is NAr1,

Any one of X2 and Y2 is a direct bond, and the other is NAr2,

Ar1 and Ar2 are each independently hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl group, or substituted or unsubstituted heterocyclic group ego,

R"1 to R"12 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

At least one of R"1, R"4, R"7, R"8, R"11 and R"14 is an isopropyl group.

In addition, the present application is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the aforementioned compound.

The organic light-emitting device using the compound according to the exemplary embodiment of the present application may obtain a low driving voltage, high luminous efficiency, or high color purity.

1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
2 shows an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked. It shows an example.

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

The present specification provides a compound represented by Chemical Formula 1.

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

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

In the present specification, the term "substituted or unsubstituted" refers to hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any 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, 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 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 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, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. Does not.

In the present specification, the alkoxy group may be a straight chain, branched chain, or cyclic chain. Although the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. May be, but is 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. 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, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferably 10 to 24 carbon atoms. Specifically, 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.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

,

및

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

,

,

And

And the like, but is not limited thereto.

In the present specification, the heterocyclic group is an atom other than carbon and includes one or more heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms of the heterocyclic group 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, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, Isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are not limited thereto.

In the present specification, the description of the aryl group described above may be applied except that the aromatic hydrocarbon ring is a divalent group.

In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heterocycle is a divalent group.

In the present specification, an aryl group among an aralkyl group, an aralkylamine group, an aralkenyl group, and an arylamine group may be described above with respect to the aryl group.

In the present specification, the alkyl group among the aralkyl group, aralkylamine group, and alkylamine group may be described above with respect to the alkyl group.

In the present specification, the heteroaryl group may be described with respect to the aforementioned heterocyclic group.

In the present specification, the meaning of forming a ring by bonding with adjacent groups to each other means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Or it means to form a substituted or unsubstituted aromatic heterocycle.

In the present specification, the aliphatic hydrocarbon ring refers to a ring that is not aromatic and includes only carbon and hydrogen atoms.

In the present specification, examples of the aromatic hydrocarbon ring include a phenyl group, a naphthyl group, and an anthracenyl group, but are not limited thereto.

In the present specification, the aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms.

In the present specification, the aromatic heterocycle means an aromatic ring containing at least one heteroatom.

In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic hetero ring and the aromatic hetero ring may be monocyclic or polycyclic.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent located three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted with an ortho position in a benzene ring and two substituents substituted with the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the meaning of adjacent groups being bonded to each other to form a ring means that adjacent groups are bonded to each other as described above to form a 5 to 8 membered hydrocarbon ring or a 5 to 8 membered heterocycle, and , It may be monocyclic or polycyclic, and may be aliphatic, aromatic, or condensed forms thereof, but is not limited thereto.

According to the exemplary embodiment of the present application, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

In addition, according to the exemplary embodiment of the present application, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 60 carbon atoms.

In addition, according to the exemplary embodiment of the present application, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present application, the R"1 to R"14 are each independently hydrogen; heavy hydrogen; It is a substituted or unsubstituted alkyl group or a substituted or unsubstituted silyl group.

In addition, according to an exemplary embodiment of the present application, the R"1 to R"14 are each independently, hydrogen; It is a substituted or unsubstituted C1-C60 alkyl group or a substituted or unsubstituted C1-C60 silyl group.

In addition, according to an exemplary embodiment of the present application, the R"1 to R"14 are each independently, hydrogen; It is a substituted or unsubstituted C1-C30 alkyl group or a substituted or unsubstituted C1-C30 silyl group.

In addition, according to an exemplary embodiment of the present application, the R"1 to R"14 are each independently, hydrogen; It is a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted C1-C10 silyl group.

Further, according to an exemplary embodiment of the present application, when X1 is NAr1, R''7 or R''8 is an isopropyl group, when Y1 is NAr1, R''11 is an isopropyl group, and X2 is NAr2. When, R''1 or R''14 is an isopropyl group, and when Y2 is NAr2, R''4 is an isopropyl group. According to an exemplary embodiment of the present application, Formula 1 is represented by the following structural formulas. It is chosen from among.

In addition, the present application provides an organic light-emitting device including the above-described compound.

In the exemplary embodiment of the present application, the first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

In the present application, when a member is positioned "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member exists between the two members.

In the present application, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless specifically stated to the contrary.

The organic material layer of the organic light emitting device of the present application may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In the exemplary embodiment of the present application, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or the hole injection and transport layer includes the compound. The hole injection and transport layer is a layer that simultaneously performs hole injection and transport.

In the exemplary embodiment of the present application, the organic material layer includes an emission layer, and the emission layer includes the compound.

In the exemplary embodiment of the present application, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound. The electron injection and transport layer is a layer that simultaneously performs electron injection and transport.

In the exemplary embodiment of the present application, the organic light emitting device is a hole injection layer and a hole transport layer. It further includes one or two or more layers selected from the group consisting of an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

In the exemplary embodiment of the present application, the organic material layer includes an emission layer, and the emission layer includes the compound as a blue dopant.

The emission layer may include a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include compounds, dibenzofuran derivatives, and ladder furan compounds. , Pyrimidine derivatives, and the like, but are not limited thereto.

In the exemplary embodiment of the present application, the emission layer further includes a compound containing anthracene as a host.

In the exemplary embodiment of the present application, the host is represented by the following formula (2).

[Formula 2]

In Formula 2,

R1 to R10 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In addition, in the exemplary embodiment of the present application, the R1 to R10 are hydrogen; heavy hydrogen; It is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

In addition, in the exemplary embodiment of the present application, the R1 to R10 are hydrogen; heavy hydrogen; It is a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C3-C60 heterocyclic group.

In addition, in the exemplary embodiment of the present application, the R1 to R10 are hydrogen; heavy hydrogen; It is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms.

In addition, in the exemplary embodiment of the present application, the R1 to R10 are hydrogen; It is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms.

In addition, in the exemplary embodiment of the present application, Formula 2 is selected from the following structural formulas.

In the exemplary embodiment of the present application, the thickness of the organic material layer including the compound of Formula 1 is 10 Å to 500 Å.

In the exemplary embodiment of the present application, the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. Two or more organic material layers are provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, and at least one of the two or more organic material layers includes the compound. In the exemplary embodiment of the present application, two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and injects electrons, and a hole blocking layer.

In the exemplary embodiment of the present application, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound. Specifically, in the exemplary embodiment of the present application, the compound may be included in one of the two or more electron transport layers, and may be included in each of two or more electron transport layers.

In addition, in the exemplary embodiment of the present application, when the compound is included in each of the two or more electron transport layers, materials other than the compound may be the same or different from each other.

In the exemplary embodiment of the present application, the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamino group, carbazole group, or benzocarbazole group in addition to the organic material layer including the compound.

In another exemplary embodiment, the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In another exemplary embodiment, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

For example, the structure of an organic light-emitting device according to an exemplary embodiment of the present application is illustrated in FIGS. 1 and 2.

1 illustrates a structure of an organic light-emitting device in which a substrate 1, an anode 2, an emission layer 3, and a cathode 4 are sequentially stacked. In such a structure, the compound may be included in the emission layer 3.

2 shows an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (3), an electron transport layer (7), and a cathode (4) are sequentially stacked. The structure is illustrated. In such a structure, the compound may be included in one or more of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.

The organic light-emitting device of the present application may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound of the present application, that is, the compound.

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

The organic light-emitting device of the present application may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound, that is, the compound represented by Formula 1.

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

In addition, the compound of Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, ink jet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to such a method, an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

In the exemplary embodiment of the present application, the first electrode is an anode, and the second electrode is a cathode.

In another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

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 anode material that can be used in the present invention 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); A combination of a metal and an oxide such as ZnO:Al or SNO2: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 multi-layered materials such as LiF/Al or LiO2/Al, but are not limited thereto.

The hole injection material is a layer that injects holes from the electrode, and the hole injection material has the ability to transport holes, 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 in the light emitting layer. A compound that prevents the excitons from moving to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferable. 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.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer.The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The electron transport material is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. The electron transport material is a material that can transfer electrons to the emission layer by receiving electrons from the cathode. This is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or light emitting material, and injects holes of excitons generated in the light emitting layer. A compound that prevents migration to the layer and is excellent in thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. 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.

The hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but are not limited thereto.

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

The preparation of the compound represented by Formula 1 and the organic light-emitting device including the same will be described in detail in the following Examples. However, the following examples are for illustrative purposes only, and the scope of the present specification is not limited thereto.

[Synthesis Example]

<Synthesis Example 1> Synthesis of Compound 1

(Synthesis Example 1-a) Synthesis of Compound 1-a

[Compound 1-a]

Dissolve 1,6-dibromo-3,8-diisopropylpyrene (20.0g, 45.0mmol), (2-nitrophenyl)boronic acid (15.8g, 94.5mmol) in THF 300ml in a 3-neck flask, and K2CO3 (24.9g, 180.1mmol) Dissolved in 150ml of H2O. Pd(PPh3)4 (1.6g, 1.4mmol) was added thereto, and the mixture was stirred for 8 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the mixture was cooled to room temperature, and the reaction solution was transferred to a separatory funnel, and extracted with ethyl acetate. The extract was dried over MgSO 4, filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 20.2 g of compound 1-a. (Yield 85%, MS[M+H]+= 529)

(Synthesis Example 1-b) Synthesis of Compound 1-b

[Compound 1-a] [Compound 1-b]

Compound 1-a (20.0g, 37.8mmol), Triphenylphosphine (13.1g, 94.6mmol), and 200ml of o-dichlorobenzene were added to a two necked flask and stirred for 12 hours under reflux conditions. When the reaction was completed, the mixture was cooled to room temperature, distilled under reduced pressure to remove the solvent, and extracted with water and CH2Cl2. The extract was dried over MgSO 4, filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 12.5 g (71% yield) of compound 1-b. (MS[M+H]+= 465)

(Synthesis Example 1-c) Synthesis of Compound 1

[Compound 1-b] [Compound 1]

Dissolve compound 1-b (12.0g, 25.8mmol) and bromodobenzene (8.5g, 54.2mmol) in 300ml xylene in a 3-neck flask, sodium tert-butoxide (7.4g, 77.5mmol), Bis (tri-tert-butylphosphine) palladium After (0) (0.5g, 1.0mmol) was added, the mixture was stirred for 6 hours under reflux conditions in an argon atmosphere. When the reaction was completed, the mixture was cooled to room temperature, 200 ml of H2O was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO 4, filtered and concentrated, and the sample was purified by silica gel column chromatography, and then 6.7 g of Compound 1 was obtained through sublimation purification. (Yield 42%, MS[M+H]+= 617)

<Synthesis Example 2> Synthesis of Compound 2

(Synthesis Example 2-a) Synthesis of Compound 2

[화합물 1-b] [화합물 2]

[Compound 1-b] [Compound 2]

In a 3-neck flask, compound 1-b (12.0g, 25.8mmol), 1-bromo-4-(tert-butyl)benzene (11.6g, 54.2mmol) was dissolved in xylene 300ml and sodium tert-butoxide (7.4g, 77.5mmol). ), Bis(tri-tert-butylphosphine)palladium(0)(0.5g, 1.0mmol) was added, followed by stirring for 6 hours under reflux conditions in an argon atmosphere. When the reaction was completed, the mixture was cooled to room temperature, 200 ml of H2O was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO 4, filtered and concentrated, the sample was purified by silica gel column chromatography, and then 6.0 g of Compound 2 was obtained through sublimation purification. (Yield 32%, MS[M+H]+= 729)

<Synthesis Example 3> Synthesis of Compound 3

(Synthesis Example 3-a) Synthesis of Compound 3-a

[Compound 3-a]

In a three-neck flask, 1,6-dibromo-3,8-diisopropylpyrene (20.0g, 45.0mmol), (4-(tert-butyl)-2-nitrophenyl)boronic acid (21.1g, 94.5mmol) was dissolved in 300ml of THF. Dissolve K2CO3 (24.9g, 180.1mmol) in 150ml of H2O. Pd(PPh3)4 (1.6g, 1.4mmol) was added thereto, and the mixture was stirred for 8 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the mixture was cooled to room temperature, and the reaction solution was transferred to a separatory funnel, and extracted with ethyl acetate. The extract was dried over MgSO 4, filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 22.5 g of compound 1-a. (Yield 78%, MS[M+H]+= 641)

(Synthesis Example 3-b) Synthesis of Compound 3-b

[Compound 3-a] [Compound 3-b]

Compound 3-a (22.0g, 34.3mmol), Triphenylphosphine (11.9g, 85.8mmol), and 220ml of o-dichlorobenzene were added to a two-necked flask and stirred for 12 hours under reflux conditions. When the reaction was completed, the mixture was cooled to room temperature, distilled under reduced pressure to remove the solvent, and extracted with water and CH2Cl2. The extract was dried over MgSO 4, filtered and concentrated, and the sample was purified by silica gel column chromatography to give 12.9 g (yield 65%) of compound 3-b. (MS[M+H]+= 577)

(Synthesis Example 3-c) Synthesis of Compound 3

[Compound 3-b] [Compound 3]

In a 3-neck flask, compound 3-b (12.0g, 20.8mmol), (4-bromophenyl)trimethylsilane (10.0g, 43.7mmol) was dissolved in xylene 300ml, sodium tert-butoxide (6.0g, 62.4mmol), Bis (tri- After tert-butylphosphine)palladium(0) (0.4g, 0.8mmol) was added, the mixture was stirred for 8 hours under reflux conditions in an argon atmosphere. When the reaction was completed, the mixture was cooled to room temperature, 200 ml of H2O was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO 4, filtered and concentrated, the sample was purified by silica gel column chromatography, and then 6.4 g of Compound 3 was obtained through sublimation purification. (Yield 35%, MS[M+H]+= 874)

<Synthesis Example 4> Synthesis of Compound 4

(Synthesis Example 4-a) Synthesis of Compound 4

[Compound 3-b] [Compound 4]

In a three-neck flask, dissolve the compound 3-b (12.0g, 20.8mmol) and 5-bromo-1,2,3-trifluorobenzene (9.2g, 43.7mmol) in 300ml xylene and sodium tert-butoxide (6.0g, 62.4mmol) , Bis(tri-tert-butylphosphine)palladium(0)(0.4g, 0.8mmol) was added, followed by stirring for 6 hours under reflux conditions in an argon atmosphere. When the reaction was completed, the mixture was cooled to room temperature, 200 ml of H2O was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO 4, filtered and concentrated, and the sample was purified by silica gel column chromatography, and then 6.4 g of compound 4 was obtained through sublimation purification. (Yield 41%, MS[M+H]+= 781)

<Synthesis Example 5> Synthesis of Compound 5

(Synthesis Example 5-a) Synthesis of Compound 5-a

[Compound 5-a]

In a three-necked flask, 1,6-dibromopyrene (20.0g, 55.5mmol), Bis(pinacolato)diboron (31.0g, 122.2mmol) were dissolved in 300ml of Toluene, and K2CO3 (30.7g, 222.2mmol) was dissolved in 150ml of H2O. Pd(dppf)Cl2 (1.2g, 1.7mmol) was added thereto, and the mixture was stirred for 12 hours under reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, and washed twice with 100 ml of water. After extracting the organic layer, the extract was dried over MgSO 4, filtered, and recrystallized using CH 2 Cl 2 and hexnae to obtain 21.9 g of compound 5-a. (Yield 87%, MS[M+H]+= 454)

(Synthesis Example 5-b) Synthesis of Compound 5-b

[Compound 5-a] [Compound 5-b]

In a three-necked flask, compound 5-a (21.0g, 46.2mmol) and 1-bromo-3-isopropyl-2-nitrobenzene (23.7g, 97.1mmol) were dissolved in THF 315ml, and K2CO3 (25.6g, 184.9mmol) was dissolved in H2O 158ml. Melt it in. Pd(PPh3)4 (1.6g, 1.4mmol) was added thereto, and the mixture was stirred for 8 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the mixture was cooled to room temperature, and the reaction solution was transferred to a separatory funnel, and extracted with ethyl acetate. The extract was dried over MgSO 4, filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 19.8 g of compound 5-b. (Yield 81%, MS[M+H]+= 529)

(Synthesis Example 5-c) Synthesis of Compound 5-c

[Compound 5-b] [Compound 5-c]

Compound 5-b (19.0g, 35.9mmol), Triphenylphosphine (12.4g, 89.9mmol), and 190ml of o-dichlorobenzene were added to a two-necked flask and stirred for 12 hours under reflux conditions. When the reaction was completed, the mixture was cooled to room temperature, distilled under reduced pressure to remove the solvent, and extracted with water and CH2Cl2. The extract was dried over MgSO 4, filtered and concentrated, and the sample was purified by silica gel column chromatography to give 12.7 g (yield 76%) of compound 5-c. (MS[M+H]+= 465)

(Synthesis Example 5-d) Synthesis of Compound 5

[Compound 5-c] [Compound 5]

In a three-necked flask, the compound 5-c (12.0g, 25.8mmol), 1-bromo-4-(tert-butyl)benzene (11.6g, 54.2mmol) was dissolved in 300ml of xylene and sodium tert-butoxide (7.4g, 77.5mmol). ), Bis(tri-tert-butylphosphine)palladium(0)(0.5g, 1.0mmol) was added, followed by stirring for 6 hours under reflux conditions in an argon atmosphere. When the reaction was completed, the mixture was cooled to room temperature, 200 ml of H2O was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO 4, filtered and concentrated, the sample was purified by silica gel column chromatography, and then 6.8 g of Compound 5 was obtained through sublimation purification. (Yield 36%, MS[M+H]+= 729)

<Synthesis Example 6> Synthesis of Compound 6

(Synthesis Example 6-a) Synthesis of Compound 6

[Compound 5-c] [Compound 6]

In a three-necked flask, compound 5-c (12.0g, 25.8mmol), 4-bromodibenzo[b,d]furan (13.4g, 54.2mmol) was dissolved in xylene 300ml, sodium tert-butoxide (7.4g, 77.5mmol), Bis After (tri-tert-butylphosphine)palladium(0)(0.5g, 1.0mmol) was added, the mixture was stirred for 6 hours under reflux conditions in an argon atmosphere. When the reaction was completed, the mixture was cooled to room temperature, 200 ml of H2O was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO 4, filtered and concentrated, and the sample was purified by silica gel column chromatography, and then 8.2 g of Compound 6 was obtained through sublimation purification. (Yield 40%, MS[M+H]+= 797)

<Synthesis Example 7> Synthesis of Compound 7

(Synthesis Example 7-a) Synthesis of Compound 7-a

[Compound 7-a]

Dissolve 1,6-dibromopyrene (12.0g, 31.6mmol), 2-chloro-6-isopropylaniline (11.2g, 66.3mmol) in 300ml of toluene in a three-necked flask, and sodium tert-butoxide (9.1g, 94.7mmol), Bis( After adding tri-tert-butylphosphine)palladium(0) (0.6g, 1.3mmol), the mixture was stirred for 6 hours under reflux conditions in an argon atmosphere. When the reaction was completed, the mixture was cooled to room temperature, 200 ml of H2O was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO 4, filtered and concentrated, and the sample was purified by silica gel column chromatography, and then 12.1 g of compound 7-a was obtained through sublimation purification. (Yield 71%, MS[M+H]+= 538)

(Synthesis Example 7-b) Synthesis of Compound 7-b

[Compound 7-a] [Compound 7-b]

Compound 7-a (12.0g, 22.3mmol), Palladium(II) acetate (0.3g, 1.1mmol), Tricyclohexylphosphine tetrafluoroborate (0.8g, 2.2mmol), K2CO3 (12.3g, 89.3mmol) toluene 300ml And stirred for 18 hours under reflux conditions in an argon atmosphere. When the reaction was completed, the mixture was cooled to room temperature, 200 ml of H2O was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO 4, filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 7.2 g of compound 7-b. (Yield 69%, MS[M+H]+= 465)

(Synthesis Example 7-c) Synthesis of Compound 7

[Compound 7-b] [Compound 7]

In a three-neck flask, compound 7-b (7.0g, 15.1mmol) and 1-bromo-4-(tert-butyl)benzene (6.7g, 31.6mmol) were dissolved in 175ml of xylene and sodium tert-butoxide (4.3g, 45.2mmol). ), Bis(tri-tert-butylphosphine)palladium(0)(0.3g, 0.6mmol) was added, followed by stirring for 8 hours under reflux conditions in an argon atmosphere. When the reaction was completed, after cooling to room temperature, 150 ml of H2O was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO 4, filtered and concentrated, the sample was purified by silica gel column chromatography, and then 4.5 g of Compound 7 was obtained through sublimation purification. (Yield 41%, MS[M+H]+= 729)

<Synthesis Example 8> Synthesis of Compound 8

(Synthesis Example 8-a) Synthesis of Compound 8

[Compound 7-b] [Compound 8]

In a three-necked flask, compound 7-b (7.0g, 15.1mmol) and 4-bromodibenzo[b,d]furan (7.8g, 31.6mmol) were dissolved in 175ml of xylene, and sodium tert-butoxide (4.3g, 45.2mmol), Bis After (tri-tert-butylphosphine)palladium(0)(0.3g, 0.6mmol) was added, the mixture was stirred for 8 hours under reflux conditions in an argon atmosphere. When the reaction was completed, after cooling to room temperature, 150 ml of H2O was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO 4, filtered and concentrated, and the sample was purified by silica gel column chromatography, and then compound 84.0 g was obtained through sublimation purification. (Yield 33%, MS[M+H]+= 797)

[Example]

<Example 1>

A glass substrate coated with a thin film of ITO (Indium Tin Oxide) to a thickness of 1,400Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made 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 prepared ITO transparent electrode, the following [HI-A] and hexaazatriphenylene (HAT) were sequentially thermally vacuum deposited to a thickness of 650Å and 50Å, respectively, to form a hole injection layer.

[HI-A] [HAT]

The hole transport layer [HT-A] was vacuum-deposited to a thickness of 600 Å, and the electron blocking layer [HT-B] was thermally vacuum-deposited to a thickness of 50 Å.

[HT-A] [HT-B]

Subsequently, the following host [BH-A] and a dopant [Compound 1] of 4 wt% compared to 100 wt% of the host were vacuum-deposited to a thickness of 200 Å as a light emitting layer.

[BH-A] [Compound 1]

Subsequently, the following [Compound 2-1] and [Liq] as the electron transport layer and the electron injection layer were thermally vacuum deposited to a thickness of 360Å at a ratio of 1:1 (weight ratio), and then [Liq] was vacuum deposited to a thickness of 5Å .

[ET-A] [Liq]

An organic light-emitting device was manufactured by sequentially depositing magnesium and silver on the electron injection layer to a thickness of 220 Å at a ratio of 10:1 and aluminum to a thickness of 1000 Å to form a cathode.

<Example 1> to <Example 8> and <Comparative Example 1> to <Comparative Example 5>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compounds shown in Table 1 were used instead of the compound as the dopant material of the emission layer in Example 1-1. The device performance when a current density of 10 mA/cm2 was applied to the organic light-emitting device thus fabricated was measured and shown in Table 1. Here, Full With at Half Maximum (FWHM) means the difference between two wavelengths having an intensity of half of the maximum intensity in the emission spectrum of the device.

[BD-A] [BD-B]

[BD-C] [BD-D]

[BD-E]

Dopant @ 10mA / cm ² Voltage cd/A FWHM
(nm) CIE-x CIE-y Example 1 Compound 1 3.71 6.53 25 0.143 0.056 Example 2 Compound 2 3.81 6.81 26 0.143 0.057 Example 3 Compound 3 3.75 6.82 24 0.142 0.057 Example 4 Compound 4 3.80 6.38 25 0.144 0.058 Example 5 Compound 5 3.78 6.67 28 0.142 0.057 Example 6 Compound 6 3.78 6.67 29 0.143 0.058 Example 7 Compound 7 3.78 6.67 24 0.142 0.058 Example 8 Compound 8 3.78 6.67 29 0.143 0.057 Comparative Example 1 BD-A 3.81 5.83 55 0.138 0.112 Comparative Example 2 BD-B 4.11 5.16 39 0.140 0.091 Comparative Example 3 BD-C 4.18 5.25 41 0.141 0.092 Comparative Example 4 BD-D 4.08 5.81 38 0.140 0.093 Comparative Example 5 BD-E 6.12 0.82 70 0.138 0.189

In the structure in which two amines are substituted, such as BD-A applied in Comparative Example 1 of Table 1, since the bonds connected to the amine are all rotatable bonds, vibration of the material becomes easy. When this structure is used as a light emitting dopant in an organic EL device, a spectrum having an FWHM of 50 nm or more is obtained. For higher color purity, a material with low FWHM should be introduced. The substances of BD-B to BD-D applied in Comparative Examples 2 to 4 have a structure obtained by condensing a phenyl group on one of the amine substituents. In this case, it has a more rigid structure than BD-A, which reduces the FWHM of the emission spectrum, thereby obtaining an organic electroluminescent device having a higher color purity than BD-A. In compound 1, the structure of compound 8 introduced an isopropyl group next to it to prevent the rotation of the rotatable bond connected to the nitrogen element. In the case of BD-E in which a larger substituent t-butyl substituent was introduced, the bond between the nitrogen element and the phenyl group was so prevented that the entire structure was distorted, reducing the luminous efficiency, which was found to deteriorate the performance of the organic electroluminescent device. On the other hand, the organic electroluminescent device made using the structure of Compounds 1 to 8 according to an exemplary embodiment of the present invention exhibited high color purity due to less FWHM than the material of Comparative Example, as shown in Organic Table 1, and at the same time high efficiency Showed.

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

Claims (14)

Compound represented by the following formula (1):
[Formula 1]

In Formula 1,
Any one of X1 and Y1 is a direct bond, and the other is NAr1,
Any one of X2 and Y2 is a direct bond, and the other is NAr2,
When X1 is a direct bond, Y2 is NAr2; When X2 is a direct bond, Y1 is NAr1,
Ar1 and Ar2 are each independently hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted C1-C50 alkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6 To 60 aryl group, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms,
R”1 to R”14 are each independently hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted silyl group having 1 to 60 carbon atoms, substituted or unsubstituted A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms,
Two of R"1, R"4, R"7, R"8, R"11 and R"14 are isopropyl groups. The method according to claim 1,
The compounds Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms. The method according to claim 1,
Each of R"1 to R"14 is independently hydrogen; heavy hydrogen; A compound that is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted silyl group having 1 to 60 carbon atoms. The method according to claim 1,
When X1 is NAr1, R''7 or R''8 is an isopropyl group,
When Y1 is NAr1, R''11 is an isopropyl group,
When X2 is NAr2, R''1 or R''14 is an isopropyl group,
When Y2 is NAr2, R''4 is an isopropyl group. The method according to claim 1,
The compound represented by Formula 1 is a compound selected from the following structural formulas:

. A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound according to claim 1. The organic light-emitting device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer includes the compound. The organic light-emitting device of claim 6, wherein the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound. The organic light-emitting device of claim 6, wherein the organic material layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or a hole injection and transport layer comprises the compound. The organic light-emitting device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer includes the compound as a blue dopant. The organic light-emitting device of claim 10, wherein the emission layer further comprises a compound containing anthracene as a host. The method of claim 11,
The host is an organic light emitting device represented by the following formula (2):
[Formula 2]

In Formula 2,
R1 to R10 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The method of claim 12,
R1 to R10 are hydrogen; heavy hydrogen; An organic light-emitting device that is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group. The method of claim 12,
The compound represented by Formula 2 is an organic light-emitting device selected from the following structural formulas:

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