CN113039173B - Compound and organic light emitting device using the same - Google Patents

Abstract

The present invention provides novel compounds and organic light-emitting devices utilizing the same.

Description

Compound and organic light-emitting device using the same

Technical Field

This application claims the priority based on Korean Patent Application No. 10-2019-0028864 filed on March 13, 2019, and incorporates all the contents disclosed in the document of the Korean Patent Application as a part of this specification.

The present invention relates to novel compounds and organic light-emitting devices comprising the same.

Background Art

Generally speaking, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light-emitting devices using the organic light-emitting phenomenon have wide viewing angles, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, so a lot of research is being carried out.

An organic light-emitting device generally has a structure including an anode and a cathode and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light-emitting device, the organic layer is usually formed by a multilayer structure composed of different substances, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. For such an organic light-emitting device structure, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons transition back to the ground state, light is emitted.

As for organic substances used for organic light-emitting devices as described above, development of new materials continues to be required.

[Prior art literature]

[Patent Document]

(Patent Document 0001) Korean Patent Publication No. 10-2000-0051826

Summary of the invention

Technical issues

The present invention relates to novel compounds and organic light-emitting devices comprising the same.

Solution to the problem

The present invention provides a compound represented by the following Chemical Formula 1:

[Chemical formula 1]

In the above chemical formula 1,

_L1 and _L2 are each independently a single bond, or a substituted or unsubstituted C _6-60 arylene group,

Ar ₁ and Ar ₂ are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, triphenylene, pyrene, phenyl, tetraphenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl or benzonaphthothiophenyl,

wherein _Ar1 and _Ar2 are unsubstituted or substituted with one or more substituents independently selected from _C1-20 alkyl and _C6-20 aryl groups,

Ar ₃ is a substituted or unsubstituted biphenyl group.

In addition, the present invention provides an organic light-emitting device, which includes: a first electrode; a second electrode arranged opposite to the first electrode; and one or more organic layers arranged between the first electrode and the second electrode, and one or more of the organic layers contains a compound represented by the above chemical formula 1.

Effects of the Invention

The compound represented by the above Chemical Formula 1 may be used as a material of an organic layer of an organic light-emitting device, and may achieve improved efficiency, low driving voltage, and/or improved lifespan characteristics in the organic light-emitting device.

BRIEF DESCRIPTION OF THE DRAWINGS

1 illustrates an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a hole transport layer 3 , a light-emitting layer 4 , an electron injection and transport layer 5 , and a cathode 6 .

2 illustrates an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a hole injection layer 7 , a hole transport layer 3 , an electron suppression layer 8 , a light-emitting layer 4 , a hole blocking layer 9 , an electron injection and transport layer 5 , and a cathode 6 .

DETAILED DESCRIPTION

In the following, the present invention will be described in more detail to help understanding the present invention.

(Definition of terms)

In this manual, and It represents the bond to other substituents.

In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group ( Alkyl thioxy); arylthio ( Aryl thioxy); alkylsulfonyl ( Alkyl sulfoxy); arylsulfonyl ( The present invention may be substituted or unsubstituted with one or more substituents of heteroaryl groups containing one or more N, O and S atoms, or substituted or unsubstituted with a substituent formed by connecting two or more substituents among the substituents exemplified above. For example, "a substituent formed by connecting two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may also be interpreted as a substituent formed by connecting two phenyl groups.

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

In the present specification, in the ester group, the oxygen of the ester group may be substituted by a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but the number of carbon atoms is preferably 1 to 25. Specifically, the compound may have the following structure, but the present invention is not limited thereto.

In the present specification, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited thereto.

In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but the present invention is not limited thereto.

In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 6. 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, and 5-methylhexyl, but are 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 number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are 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-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are 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, etc., but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group having aromaticity. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, Base, etc., but not limited to this.

In the present specification, the heteroaryl group is a heteroaryl group containing one or more of O, N, Si and S as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of the heteroaryl group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridinyl, bipyridinyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl and dibenzofuranyl, but are not limited thereto.

In this specification, the aryl group in aralkyl, aralkenyl, alkylaryl, arylamine, and arylsilyl is the same as the examples of the above-mentioned aryl group. In this specification, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the examples of the above-mentioned alkyl group. In this specification, the heteroaryl group in heteroarylamine can be applied to the above-mentioned description of the heteroaryl group. In this specification, the alkenyl group in aralkenyl is the same as the examples of the above-mentioned alkenyl group. In this specification, the arylene group is a divalent group, and the above-mentioned description of the aryl group can be applied. In this specification, the heteroarylene group is a divalent group, and the above-mentioned description of the heteroaryl group can be applied. In this specification, the hydrocarbon ring is not a monovalent group, but is formed by combining two substituents, and the above-mentioned description of the aryl group or the cycloalkyl group can be applied. In this specification, the heterocycle is not a monovalent group, but is formed by combining two substituents, and the above-mentioned description of the heteroaryl group can be applied.

(Compound)

In another aspect, the present invention provides a compound represented by the above Chemical Formula 1.

Specifically, the compound represented by the above chemical formula 1 is an amine compound in which the Ar ₃ substituent is connected to the N atom through a biphenyl-1,4-diyl linking group (ortho-biphenyl linking group). At this time, the above Ar ₃ substituents are substituted or unsubstituted biphenyls, preferably having a monocyclic substituent structure formed by connecting more than two phenyl groups. Therefore, the above compound can show improved hole transport ability and improved thermal stability compared with the compound without the above linking group or the monocyclic substituent structure formed by connecting more than two phenyl groups. Thus, the organic light-emitting device using the above compound can show characteristics such as high efficiency, low driving voltage and long life.

In the above Chemical Formula 1, preferably, _L1 and _L2 are each independently a single bond, a phenylene group, a biphenyldiyl group or a naphthylene group.

More preferably, _L1 and _L2 are a single bond or a 1,4-phenylene group.

Preferably, Ar ₁ and Ar ₂ are phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl or benzonaphthothiophenyl, wherein the above Ar ₁ and Ar ₂ are unsubstituted or substituted with C _6-20 aryl.

More preferably, Ar ₁ and Ar ₂ are each independently selected from any one of the following groups:

In the above groups,

R is hydrogen or phenyl.

In this case, Ar ₁ and Ar ₂ may be identical to each other. Preferably, the case where both Ar ₁ and Ar ₂ are phenyl groups is excluded because the glass transition temperature (Tg) of the above compound may become low.

In addition, Ar ₁ and Ar ₂ may be different from each other.

Preferably, Ar ₃ is unsubstituted or is a biphenyl substituted with a phenyl, biphenyl or terphenyl group.

More preferably, Ar ₃ is a biphenyl group, a terphenyl group or a quaterphenyl group.

Most preferably, Ar ₃ is any one selected from the following groups:

Preferably, the compound is represented by any one of the following Chemical Formulas 1-1 to 1-3: [Chemical Formula 1-1]

[Chemical formula 1-2]

[Chemical formula 1-3]

In the above chemical formulas 1-1 to 1-3,

The explanations for Ar ₁ and Ar ₂ are the same as those in the above chemical formula 1.

Ph means phenyl,

n is 0 or 1,

m is 0, 1 or 2.

Representative examples of the compound represented by the above Chemical Formula 1 are shown below:

On the other hand, as an example, the compound represented by the above Chemical Formula 1 can be produced by the production method shown in the following Reaction Formula 1. The above production method can be further embodied in the production examples described below.

[Reaction 1]

In the above reaction formula 1, the description of each substituent is the same as the above definition. The above step 1-1 is a step of introducing a bromine group into the starting material S-1 to produce the intermediate compound I-1, the above step 1-2 is a step of introducing a substituent Ar ₃ at a position substituted with bromine by Suzuki coupling reaction to produce the intermediate compound I-2, preferably in the presence of a palladium catalyst and a base, and the above step 1-3 is a reaction of introducing a substituent into the intermediate compound I-2 as a secondary amine to produce a compound represented by the above chemical formula 1 as a tertiary amine compound, preferably under a palladium catalyst. Such a production method can be more specific in the production examples described later.

(Organic Light Emitting Devices)

On the other hand, the present invention provides an organic light-emitting device including the compound represented by the above Chemical Formula 1. As an example, the present invention provides an organic light-emitting device, which includes: a first electrode; a second electrode disposed opposite to the above first electrode; and one or more organic layers disposed between the above first electrode and the above second electrode, wherein one or more of the organic layers includes the compound represented by the above Chemical Formula 1.

The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which two or more organic 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, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or the layer that simultaneously injects and transports holes includes the compound represented by Chemical Formula 1.

In addition, the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1.

The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure that includes, in addition to the light-emitting layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number or a larger number of organic layers.

In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device of a structure (normal type) in which the first electrode is an anode, the second electrode is a cathode, and an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device of an inverted structure (inverted type) in which the first electrode is a cathode, the second electrode is an anode, and a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to one embodiment of the present invention is illustrated in FIGS. 1 and 2.

1 illustrates an example of an organic light emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron injection and transport layer 5, and a cathode 6. In the structure described above, the compound represented by the above Chemical Formula 1 may be included in the above hole transport layer.

2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6. In the structure described above, the compound represented by the above Chemical Formula 1 may be contained in the above hole injection layer, hole transport layer, or electron suppression layer.

The organic light-emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers contains the compound represented by the above Chemical Formula 1. In addition, when the organic light-emitting device includes a plurality of organic layers, the organic layers can be formed of the same substance or different substances.

For example, the organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, it can be manufactured as follows: a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation is used to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode substance, an organic layer, and an anode substance on a substrate.

In addition, the compound represented by the above chemical formula 1 can be used not only by vacuum evaporation method but also by solution coating method to form an organic layer when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating method, dip coating method, blade coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited to these.

In addition to these methods, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited to this.

As an example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

In order to smoothly inject holes into the organic layer, the anode material is preferably a material with a large work function. Specific examples of the anode 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 with a small work function in order to facilitate electron injection into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF/Al or _LiO2 /Al, but are not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode. As a hole injection material, it is preferably a compound having the ability to transport holes, the effect of injecting holes from the anode, an excellent hole injection effect for the light-emitting layer or the light-emitting material, and a compound having excellent film forming ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyanilines, and polythiophene conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. A material with a large mobility of holes is suitable. As the hole transport material, a compound represented by the above chemical formula 1 is used, or an arylamine-based organic substance, a conductive polymer, and a block copolymer having both a conjugated portion and a non-conjugated portion can be used, but it is not limited thereto.

The electron suppression layer is a layer formed on the hole transport layer, preferably in contact with the light-emitting layer, and improves the efficiency of the organic light-emitting device by adjusting the hole mobility and preventing the excessive migration of electrons to increase the probability of hole-electron bonding. The electron suppression layer includes an electron blocking substance. As an example of such an electron blocking substance, a compound represented by the above chemical formula 1 is used, or an arylamine organic substance or the like can be used, but it is not limited thereto.

The luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine them to emit light in the visible light region. It is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complex (Alq ₃ ); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo azole, benzothiazole and benzimidazole compounds; poly(p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

As described above, the light-emitting layer may include a host material and a dopant material. The host material may also include an aromatic fused ring derivative or a heterocyclic compound. Specifically, as aromatic fused ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited thereto.

As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamino groups, and there are pyrene, anthracene, The styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but not limited thereto.

The hole blocking layer is a layer formed on the light-emitting layer, preferably in contact with the light-emitting layer, and improves the efficiency of the organic light-emitting device by adjusting the electron mobility and preventing the excessive migration of holes to increase the probability of hole-electron bonding. The hole blocking layer contains a hole blocking substance. Examples of such a hole blocking substance include azine derivatives containing triazine, triazole derivatives, Compounds into which an electron-withdrawing group is introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, phosphine oxide derivatives, and the like.

The electron injection and transport layer is a layer that injects electrons from the electrode and transports the received electrons to the light-emitting layer, and acts as an electron transport layer and an electron injection layer at the same time, and is formed on the light-emitting layer or the hole blocking layer. As such an electron injection and transport substance, a substance that can well inject electrons from the cathode and transfer them to the light-emitting layer is suitable for substances with high electron mobility. Specific examples of electron injection and transport substances include Al complexes of 8-hydroxyquinoline, complexes containing Alq ₃ , organic free radical compounds, hydroxyflavone-metal complexes, triazine derivatives, etc., but are not limited to these. Alternatively, it can also be combined with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone and the like, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives and the like can be used together, but are not limited thereto.

Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

In addition, the compound represented by the above Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to being included in an organic light emitting device.

The preparation of the compound represented by the above Chemical Formula 1 and the organic light-emitting device including the same is specifically described in the following examples. However, the following examples are used to illustrate the present invention, and the scope of the present invention is not limited thereto.

Preparation Example 1: Preparation of Compound 1

Step 1-1: Preparation of N-(biphenyl-4-yl)-5-bromobiphenyl-2-amine

Under nitrogen atmosphere, in a 1000 mL round-bottom flask, the compound N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (100.0 g, 311.52 mmol) and NBS (55.46 g, 310.52 mmol) were completely dissolved in 600 mL of DMF and stirred at room temperature for 5 hours. The substance obtained by filtration was recrystallized with 850 mL of ethyl acetate to produce the title compound (89.91 g, yield 72%).

MS[M+H] ⁺ ＝400

Step 1-2: Preparation of Compound A-1

Under nitrogen atmosphere, in a 500mL round-bottom flask, the compound N-(biphenyl-4-yl)-5-bromobiphenyl-2-amine (15.0g, 37.50mmol) and compound b1 (7.43g, 37.50mmol) prepared in step 1-1 above were completely dissolved in 300mL of tetrahydrofuran (THF), and then 2M potassium carbonate aqueous solution (150mL) was added, and tetrakis(triphenylphosphine)palladium (1.30g, 1.13mmol) was added, and heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure, and recrystallized with 320mL of ethyl acetate to prepare compound A-1 (12.47g, yield 70%).

MS[M+H] ⁺ ＝474

Step 1-3: Preparation of Compound 1

Under nitrogen atmosphere, in a 500mL round-bottom flask, compound A-1 (9.72g, 20.56mmol) and compound a1 (6.50g, 19.58mmol) were completely dissolved in 280mL of xylene, and NaOtBu (2.82g, 29.37mmol) was added, and bis(tri-tert-butylphosphine)palladium (0) (0.20g, 0.39mmol) was added, and heated and stirred for 3 hours. The temperature was lowered to room temperature, and after filtering to remove the base (base), the xylene was concentrated under reduced pressure and recrystallized with 230mL of ethyl acetate, thereby producing compound 1 (7.44g, yield: 52%).

MS[M+H] ⁺ ＝726

Preparation Example 2: Preparation of Compound 2

Compound A-2 was produced by the same method as in Production Example 1, except that Compound b2 was used instead of Compound b1.

Then, in a 500 mL round-bottom flask under a nitrogen atmosphere, compound A-2 (9.69 g, 20.48 mmol) and compound a2 (5.50 g, 19.50 mmol) were completely dissolved in 290 mL of xylene, and NaOtBu (4.22 g, 43.95 mmol) was added, and bis (tri-tert-butylphosphine) palladium (0) (0.15 g, 0.29 mmol) was added, and heated and stirred for 5 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 260 mL of ethyl acetate, thereby producing compound 2 (8.24 g, yield: 62%).

MS[M+H] ⁺ ＝676

Preparation Example 3: Preparation of Compound 3

Compound A-3 was produced by the same method as in Production Example 1, except that Compound b3 was used instead of Compound b1.

Then, in a 500 mL round-bottom flask under a nitrogen atmosphere, compound A-3 (7.93 g, 16.76 mmol) and compound a3 (4.50 g, 15.96 mmol) were completely dissolved in 230 mL of xylene, and NaOtBu (2.30 g, 23.94 mmol) was added, and bis (tri-tert-butylphosphine) palladium (0) (0.16 g, 0.32 mmol) was added, and heated and stirred for 3 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate, thereby producing compound 3 (6.36 g, yield: 59%).

MS[M+H] ⁺ ＝676

Preparation Example 4: Preparation of Compound 4

Compound B-1 was produced by the same method as in Production Example 1, except that Compound b4 was used instead of Compound b1.

Then, in a 500 mL round-bottom flask under a nitrogen atmosphere, compound B-1 (12.24 g, 22.30 mmol) and compound a4 (6.50 g, 21.24 mmol) were completely dissolved in 230 mL of xylene, and NaOtBu (3.06 g, 31.86 mmol) was added, and bis(tri-tert-butylphosphine)palladium (0) (0.22 g, 0.42 mmol) was added, and heated and stirred for 5 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 280 mL of ethyl acetate to produce compound 4 (10.07 g, yield: 61%).

MS[M+H] ⁺ ＝776

Preparation Example 5: Preparation of Compound 5

Compound B-2 was produced by the same method as in Production Example 1, except that Compound b5 was used instead of Compound b1.

Then, in a 500 mL round-bottom flask under a nitrogen atmosphere, compound B-2 (15.23 g, 27.74 mmol) and compound a5 (6.50 g, 26.42 mmol) were completely dissolved in 260 mL of xylene, and NaOtBu (3.81 g, 39.63 mmol) was added, and bis (tri-tert-butylphosphine) palladium (0) (0.27 g, 0.53 mmol) was added, and heated and stirred for 3 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 210 mL of ethyl acetate, thereby producing compound 5 (9.74 g, yield: 51%).

MS[M+H] ⁺ ＝716

Preparation Example 6: Preparation of Compound 6

Compound B-3 was produced by the same method as in Production Example 1, except that Compound b6 was used instead of Compound b1.

Then, in a 500 mL round-bottom flask under a nitrogen atmosphere, compound B-3 (12.10 g, 22.04 mmol) and compound a6 (5.50 g, 20.99 mmol) were completely dissolved in 240 mL of xylene, and NaOtBu (3.03 g, 31.49 mmol) was added, and bis (tri-tert-butylphosphine) palladium (0) (0.21 g, 0.42 mmol) was added, and heated and stirred for 35 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 230 mL of ethyl acetate, thereby producing compound 6 (9.74 g, yield: 51%).

MS[M+H] ⁺ ＝732

Preparation Example 7: Preparation of Compound 7

Compound C-1 was produced by the same method as in Production Example 1, except that Compound b7 was used instead of Compound b1.

Then, in a 500 mL round-bottom flask under a nitrogen atmosphere, compound C-1 (14.64 g, 26.66 mmol) and compound a7 (6.50 g, 25.39 mmol) were completely dissolved in 230 mL of xylene, and NaOtBu (3.66 g, 38.09 mmol) was added, and bis(tri-tert-butylphosphine)palladium (0) (0.26 g, 0.51 mmol) was added, and heated and stirred for 3 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 230 mL of ethyl acetate, thereby producing compound 7 (6.88 g, yield: 37%).

MS[M+H] ⁺ ＝726

Preparation Example 8: Preparation of Compound 8

Compound C-2 was produced by the same method as in Production Example 1, except that Compound b8 was used instead of Compound b1.

Then, in a 500 mL round-bottom flask under a nitrogen atmosphere, compound C-2 (12.17 g, 22.16 mmol) and compound a8 (6.50 g, 21.10 mmol) were completely dissolved in 250 mL of xylene, and NaOtBu (3.04 g, 31.66 mmol) was added, and bis(tri-tert-butylphosphine)palladium (0) (0.22 g, 0.42 mmol) was added, and heated and stirred for 5 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 230 mL of ethyl acetate, thereby producing compound 8 (11.55 g, yield: 70%).

MS[M+H] ⁺ ＝778

Preparation Example 9: Preparation of Compound 9

Compound D-1 was produced by the same method as in Production Example 1, except that Compound b9 was used instead of Compound b1.

Then, in a 500 mL round-bottom flask under a nitrogen atmosphere, compound D-1 (16.60 g, 27.13 mmol) and compound a9 (7.50 g, 26.60 mmol) were completely dissolved in 230 mL of xylene, and NaOtBu (3.83 g, 39.89 mmol) was added, and bis(tri-tert-butylphosphine)palladium (0) (0.14 g, 0.27 mmol) was added, and heated and stirred for 4 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 230 mL of tetrahydrofuran, thereby producing compound 9 (13.27 g, yield: 61%).

MS[M+H] ⁺ ＝778

Preparation Example 10: Preparation of Compound 10

Compound D-2 was produced by the same method as in Production Example 1, except that Compound b10 was used instead of Compound b1.

Then, in a 500 mL round-bottom flask under a nitrogen atmosphere, compound D-2 (11.21 g, 17.93 mmol) and compound a10 (5.50 g, 17.08 mmol) were completely dissolved in 240 mL of xylene, and NaOtBu (2.46 g, 25.62 mmol) was added, and bis(tri-tert-butylphosphine)palladium (0) (0.17 g, 0.34 mmol) was added, and heated and stirred for 5 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 260 mL of ethyl acetate, thereby producing compound 10 (8.87 g, yield: 60%).

MS[M+H] ⁺ ＝868

Example 1: Fabrication of an organic light-emitting device

ITO (indium tin oxide) is used The glass substrate coated with a film of thickness is placed in distilled water dissolved with detergent and washed with ultrasound. At this time, the detergent used is a product of Fischer Co., and the distilled water used is distilled water filtered twice by a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing is repeated twice with distilled water for 10 minutes. After the distilled water washing is completed, ultrasonic washing is performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it is transported to a plasma cleaning machine. In addition, the above substrate is cleaned for 5 minutes using oxygen plasma, and then the substrate is transported to a vacuum evaporation machine.

On the ITO transparent electrode prepared as the anode, the following compound HI1 and the following compound HI2 were mixed in a ratio of 98:2 (molar ratio). A hole injection layer is formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, a compound represented by the following chemical formula HT1 is deposited Then, a film with a thickness of 1000 nm was deposited on the hole transport layer. The compound 1 prepared in the above-mentioned Preparation Example 1 was vacuum-deposited to form an electron suppressing layer.

Next, on the electron suppression layer, a film having a thickness of A compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were vacuum deposited at a weight ratio of 25:1 to form a light-emitting layer.

On the above-mentioned light-emitting layer, the film thickness is A compound represented by the following chemical formula HB1 was vacuum-deposited to form a hole blocking layer. Next, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-deposited on the hole blocking layer at a weight ratio of 1:1, thereby forming a hole blocking layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A thickness of is evaporated to form a cathode.

In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 2×10 ^-7 to 5×10 ^-6 torr, and the vacuum degree is maintained during evaporation, thereby producing an organic light-emitting device.

Example 2 to Example 10

An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the compounds described in Table 1 below were used instead of the compounds in Manufacturing Example 1.

Comparative Examples 1 to 4

An organic light-emitting device was manufactured by the same method as in Example 1, except that the compounds described in Table 1 below were used instead of the compounds in Preparation Example 1. The compounds EB1, EB2, EB3, and EB4 used in Table 1 below are as follows.

Experimental Example 1

When current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in the following Table 1. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.

[Table 1]

As shown in the above Table 1, the organic light emitting device using the compound of the present invention as an electron suppressing layer exhibits excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.

Specifically, it can be seen that in Examples 1 to 10, the organic light-emitting devices using an amine-based substance connecting the "N atom" and the "substituted or unsubstituted biphenyl group" with a biphenyl-1,4-diyl group as an electron suppression layer show the characteristics of low voltage, high efficiency and long life compared to the organic light-emitting devices of Comparative Example 1 using compound EB1 having a fluorenyl group as one of the amino substituents, Comparative Example 2 using compound EB2 having a fluorine group connected to the biphenyl-1,4-diyl group, Comparative Example 4 using compound EB4 having no substituent on the biphenyl-1,4-diyl group, and Comparative Example 3 using compound EB3 having a phenyl group connected to the biphenyl-1,4-diyl group.

[Explanation of symbols]

1: Substrate 2: Anode

3: Hole transport layer 4: Light-emitting layer

5: Electron injection and transport layer 6: Cathode

7: Hole injection layer 8: Electron suppression layer

9: Hole blocking layer.

Claims (6)

1. A compound represented by the following chemical formula 1: Chemical formula 1 In the chemical formula 1, _L1 is phenylene, Ar ₁ is phenyl, _L2 is a single bond or a phenylene group, _Ar2 is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, triphenylene, pyrene, phenyl, tetraphenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl or benzonaphthothiophenyl, Ar ₃ is any one selected from the following groups: 2. The compound according to claim 1, wherein _L2 is a single bond. 3. The compound according to claim 1, wherein Ar ₂ is any one selected from the following groups: In the above groups, R is hydrogen. 4. The compound according to claim 1, wherein the compound is represented by any one of the following chemical formulas 1-1 to 1-3: Chemical formula 1-1 Chemical formula 1-2 Chemical formula 1-3 In the chemical formulas 1-1 to 1-3, Ar ₁ and Ar ₂ are the same as defined in claim 1, Ph means phenyl, n is 1, m is 0. 5. The compound according to claim 1, wherein the compound is any one selected from the following compounds: 6. An organic light-emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound described in any one of claims 1 to 5.