Novel compound and organic light emitting device comprising the same

Abstract

The present invention provides a novel compound and an organic light-emitting device comprising the same.

Description

Technology Field

[0001] The present invention relates to a novel compound and an organic light-emitting device containing the same. Background Technology

[0003] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting diodes (OLEDs) utilizing this phenomenon possess wide viewing angles, excellent contrast, and fast response times, and are being extensively researched due to their superior characteristics in terms of brightness, driving voltage, and response speed.

[0005] Organic light-emitting diodes generally have a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode. To increase the efficiency and stability of the organic light-emitting diode, the organic layer is often composed of a multilayer structure made of different materials, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light-emitting diode, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed, and light is emitted when this exciton falls back to the ground state.

[0007] There is a continuous demand for the development of new materials for organic materials used in organic light-emitting devices as described above. Prior art literature

[0009] Korean Patent Publication No. 10-2000-0051826 The problem to be solved

[0010] The present invention relates to a novel compound and an organic light-emitting device containing the same. means of solving the problem

[0012] The present invention provides a compound represented by the following chemical formula 1:

[0013] [Chemical Formula 1]

[0014]

[0015] In the above chemical formula 1,

[0016] L is a substituted or unsubstituted biphenyldiyl, terphenyldiyl, or quarterphenyldiyl, and

[0017] X are each independently N or CR1, wherein at least one of X is N, and

[0018] R1 is hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 Arilgo,

[0019] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 It is an aryl, wherein at least one of Ar1 and Ar2 is substituted with one or more cyanos, and

[0020] Ar3 is a monovalent substituent of the structure represented by the following chemical formula 2, and

[0021] [Chemical Formula 2]

[0022]

[0023] In the above chemical formula 2,

[0024] Y1 are each independently N or CR2, wherein at least one of Y1 is N, and

[0025] Y2 is NR2, O, or S, and

[0026] R2 each independently represents hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 C that is aryl, or substituted or unsubstituted by two adjacent R2s combining with each other 6-60 It forms an aryl.

[0028] In addition, the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound represented by Chemical Formula 1. Effects of the invention

[0030] The compound represented by the above-described chemical formula 1 can be used as a material for the organic layer of an organic light-emitting device, and can improve efficiency, low driving voltage, and / or lifespan characteristics in the organic light-emitting device. In particular, the compound represented by the above-described chemical formula 1 can be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection. Brief explanation of the drawing

[0032] FIG. 1 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4). FIG. 2 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (3), an electron injection and transport layer (7), and a cathode (4). Specific details for implementing the invention

[0033] The present invention will be described in more detail below to aid in understanding.

[0035] In this specification, or means a bond connected to another substituent.

[0037] In this specification, the term “substituted or unsubstituted” means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; aryl thiooxy group; alkyl sulfoxy group; aryl sulfoxy group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamine group; aralkylamine group; heteroarylamine group; arylamine group; arylphosphine group; or heterocyclic groups comprising one or more of N, O, and S atoms, or that it is substituted or unsubstituted with two or more of the exemplified substituents connected. For example, “substituents connected with two or more substituents” may be a biphenyl group. That is, the biphenyl group can be an aryl group, or it can be interpreted as a substituent in which two phenyl groups are connected.

[0039] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but it is preferred to have 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

[0040]

[0042] In the present specification, the oxygen of the ester group may be substituted with a straight-chain, branched-chain, or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

[0043]

[0045] In the present specification, the number of carbon atoms in the imide group is not particularly limited, but it is preferred to have 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

[0046]

[0048] In this specification, the silyl groups specifically include, but are not limited to, trimethylsilyl groups, triethylsilyl groups, t-butyldimethylsilyl groups, vinyldimethylsilyl groups, propyldimethylsilyl groups, triphenylsilyl groups, diphenylsilyl groups, phenylsilyl groups, etc.

[0050] In this specification, boron groups specifically include trimethylboron groups, triethylboron groups, t-butyldimethylboron groups, triphenylboron groups, phenylboron groups, etc., but are not limited thereto.

[0052] In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0054] In the present specification, the alkyl group may be a straight chain or a branched chain, and while the number of carbon atoms is not particularly limited, it is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of alkyl groups 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, cyclohectylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, Examples include 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0056] In the present specification, the alkenyl group may be a straight chain or a branched chain, 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 yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited to these.

[0058] In the present specification, the cycloalkyl group is not particularly limited, but it is preferable that it has 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc. are used, but are not limited thereto.

[0060] In this specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. As a monocyclic aryl group, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. As a polycyclic aryl group, the aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

[0062] In this specification, the fluorenyl group may be substituted, and two substituents may combine to form a spiro structure. When the fluorenyl group is substituted, It can be the back. However, it is not limited to this.

[0064] In the present specification, the heterocyclic group is a heterocyclic group comprising one or more of O, N, Si, and S as heterogeneous elements, and although the number of carbon atoms is not particularly limited, it is preferable that the number of carbon atoms be 2 to 60. Examples of heterocyclic groups include thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazine, acryl, pyridazine, pyrazinyl, quinolinyl, quinazolin, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophen, dibenzothiophen, benzofuranyl, phenanthroline, isooxazolyl, thiadiazole, phenothiazinyl, and There are dibenzofuranyl groups, etc., but are not limited to these.

[0066] In this specification, the aryl group among the aralkyl group, ar alkenyl group, alkylaryl group, and arylamine group is the same as the examples of aryl groups described above. In this specification, the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the examples of alkyl groups described above. In this specification, the description regarding the heterocyclic group described above may be applied to the heteroaryl group among the heteroaryl amine. In this specification, the alkenyl group among the ar alkenyl group is the same as the examples of alkenyl groups described above. In this specification, the description regarding the aryl group described above may be applied to the arylene except that it is a divalent group. In this specification, the description regarding the heterocyclic group described above may be applied to the heteroarylene except that it is a divalent group. In this specification, the description regarding the aryl group or cycloalkyl group described above may be applied to the hydrocarbon ring except that it is not a monovalent group and is formed by the combination of two substituents. In this specification, the description of the aforementioned heterocyclic ring may apply except that the heterocyclic ring is not monovalent and is formed by the combination of two substituents.

[0068] (compound)

[0069] The present invention provides a compound represented by the above chemical formula 1.

[0071] Preferably, L is any one selected from the group consisting of:

[0073]

[0075] Preferably, at least two of X are N.

[0077] Preferably, R1 is hydrogen, deuterium, methyl, tertbutyl, or phenyl.

[0079] Preferably, Ar1 and Ar2 are each independently phenyl, phenyl substituted with one or more deuterium groups, biphenyllyl, or terphenyllyl.

[0081] Preferably, Ar1 is phenyl or phenyl substituted with one or more deuterium groups, Ar2 is phenyl, biphenylyl, or terphenylyl, and Ar2 is substituted with one or more cyano groups.

[0083] Preferably, the monovalent substituent of the structure represented by Chemical Formula 2 is represented by the following Chemical Formula 2-1:

[0084] [Chemical Formula 2-1]

[0085]

[0086] In the above chemical formula 2-1,

[0087] R3 is substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 It is Aril.

[0088] More preferably, R3 is a substituted or unsubstituted ethyl, tertbutyl, phenyl, naphthyl, or biphenylyl.

[0090] Preferably, the monovalent substituent of the structure represented by the above chemical formula 2 is represented by the following chemical formula 2-2:

[0091] [Chemical Formula 2-2]

[0092]

[0093] In the above chemical formula 2-2,

[0094] Z is O or S, and

[0095] R4 combine with each other to form substituted or unsubstituted C 6-60 It forms an aryl.

[0096] More preferably, the R4s combine with each other to form substituted or unsubstituted benzene or naphthalene.

[0098] Preferably, the monovalent substituent of the structure represented by Chemical Formula 2 is represented by the following Chemical Formula 2-3:

[0099] [Chemical Formula 2-3]

[0100]

[0101] In the above chemical formula 2-3,

[0102] Z is O or S, and

[0103] R5 is substituted or unsubstituted C 6-60 It is Aril.

[0104] More preferably, the R5 is a substituted or unsubstituted phenyl.

[0106] Preferably, the monovalent substituent of the structure represented by Chemical Formula 2 is represented by the following Chemical Formula 2-4:

[0107] [Chemical Formula 2-4]

[0108]

[0109] In the above chemical formula 2-4,

[0110] Z is O or S, and

[0111] R6 is substituted or unsubstituted C 6-60 It is Aril.

[0112] More preferably, the R6 is a substituted or substituted phenyl.

[0114] Representative examples of compounds represented by the above chemical formula 1 are as follows:

[0115]

[0116]

[0117]

[0120]

[0122] In addition, the present invention provides a method for preparing a compound represented by Chemical Formula 1, such as the following reaction formula 1.

[0123] [Reaction Equation 1]

[0124]

[0125] In the above reaction scheme 1, the remaining definitions excluding A are as previously defined, and A is a halogen, preferably bromo or chloro.

[0127] The above reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the reaction can be modified as known in the art. The above manufacturing method can be further specified in the manufacturing examples described below.

[0129] (Organic light-emitting diode)

[0130] In addition, the present invention provides an organic light-emitting device comprising a compound represented by Chemical Formula 1. For example, the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound represented by Chemical Formula 1.

[0132] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as 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, an electron suppression 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.

[0134] Additionally, the organic layer may include a hole injection layer, a hole transport layer, or a layer that performs both hole injection and transport simultaneously, and the hole injection layer, the hole transport layer, or the layer that performs both hole injection and transport simultaneously may include a compound represented by Chemical Formula 1.

[0136] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer may include a compound represented by Chemical Formula 1. In particular, the compound according to the present invention may be used as a dopant of the light-emitting layer.

[0138] Additionally, the organic layer may include an electron transport layer, an electron injection layer, or a layer that performs electron transport and electron injection simultaneously, and the electron transport layer, the electron injection layer, or the layer that performs electron transport and electron injection simultaneously may include a compound represented by Chemical Formula 1.

[0140] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device of a normal type structure in which 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 type structure in which 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.

[0142] FIG. 1 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4). In such a structure, a compound represented by Chemical Formula 1 may be included in the light-emitting layer.

[0144] FIG. 2 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (3), an electron injection and transport layer (7), and a cathode (4). In such a structure, a compound represented by the chemical formula 1 may be included in the electron injection and transport layer.

[0146] The organic light-emitting device according to the present invention may be manufactured using materials and methods known in the art, except that one or more of the organic layers comprise a compound represented by Chemical Formula 1. Additionally, when the organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0148] For example, an 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. At this time, a physical vapor deposition (PVD) method, such as sputtering or electron beam evaporation, can be used to form an anode by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate, and then forming an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer thereon, and finally depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0150] In addition, the compound represented by Chemical Formula 1 above can be formed as an organic layer by vacuum deposition as well as solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0152] In addition to this method, an organic light-emitting diode can be manufactured by sequentially depositing an organic layer and an anode material from a cathode material onto a substrate (WO 2003 / 012890). However, the manufacturing method is not limited to this.

[0154] For example, the first electrode is a positive electrode and the second electrode is a negative electrode, or the first electrode is a negative electrode and the second electrode is a positive electrode.

[0156] As for the anode material, a material with a large work function is generally preferred so that hole injection into the organic layer can be facilitated. 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 metal and oxide such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0158] The above-mentioned cathode material is preferably a material with a small work function to facilitate electron injection into an organic layer. Specific examples of the above-mentioned cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0160] The hole injection layer above is a layer that injects holes from an electrode, and as the hole injection material, a compound having the ability to transport holes, having an excellent hole injection effect on the anode, the emissive layer, or the emissive material, preventing the movement of excitons generated in the emissive layer to the electron injection layer or the electron injection material, and also having excellent thin film formation ability is preferred. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile-hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and conductive polymers of polyaniline and polythiophene series, but are not limited to these.

[0162] The hole transport layer described above is a layer that receives holes from the hole injection layer and transports the holes to the emissive layer. As a hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the emissive layer is suitable, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions, but are not limited to these.

[0164] The above-mentioned luminescent material is a material capable of emitting light in the visible light region by receiving and combining holes and electrons from a hole transport layer and an electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzthiazole, and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0166] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material may include condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0168] Dopant materials include aromatic amine derivatives, styramine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, chrysene, and periplantene having arylamino groups; styramine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, wherein one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamino groups are substituted or unsubstituted. Specifically, styramine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. In addition, metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0170] The electron transport layer described above is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. As an electron transport material, it is a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, and a material with high electron mobility is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes, but are not limited to these. The electron transport layer can be used with any desired cathode material as in the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum layer or a silver layer. Specifically, these are cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum layer or a silver layer.

[0172] The electron injection layer is a layer that injects electrons from an electrode and has the ability to transport electrons, has an excellent electron injection effect from the cathode, an excellent electron injection effect on the emitting layer or emitting material, prevents the movement of excitons generated in the emitting layer to the hole injection layer, and also has excellent thin film formation ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, etc., their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives are included, but are not limited thereto.

[0174] The above metal complex compounds 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-naphtolato)aluminum, Examples include bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, but are not limited thereto.

[0176] The organic light-emitting device according to the present invention may be a bottom-emission device, a top-emission device, or a double-sided light-emitting device, and in particular may be a bottom-emission device for which relatively high light-emitting efficiency is required.

[0177] In addition, the compound according to the present invention may be included in organic solar cells or organic transistors in addition to organic light-emitting devices.

[0179] The preparation of the compound represented by Chemical Formula 1 above and the organic light-emitting device containing it is described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

[0181] [Example]

[0182] Example 1: Preparation of Compound E1

[0183]

[0184] E1-A (20 g, 54.2 mmol) and E1-B (28.3 g, 54.2 mmol) were added to tetrahydrofuran (400 ml) under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.5 g, 162.7 mmol) was dissolved in water (22 ml) and added, and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (1.9 g, 1.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, separated into organic and water layers, and the organic layer was distilled. This was then added to chloroform (790 mL) to dissolve it, washed twice with water, and separated into organic layers. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered and the filtrate distilled under reduced pressure. The concentrated compound was then recrystallized with chloroform and ethyl acetate to produce a white solid compound E1 (23.7 g, 60%).

[0185] MS: [M+H] + = 729

[0187] Example 2: Preparation of Compound E2

[0188]

[0189] Compound E2 was prepared in the same manner as the preparation method of Example 1, except that each starting material was prepared as per the reaction scheme above.

[0190] MS: [M+H] + = 604

[0192] Example 3: Preparation of Compound E3

[0193]

[0194] Compound E3 was prepared in the same manner as the preparation method of Example 1, except that each starting material was prepared as per the above reaction scheme.

[0195] MS: [M+H] + = 631

[0197] Example 4: Preparation of Compound E4

[0198]

[0199] Compound E4 was prepared in the same manner as the preparation method of Example 1, except that each starting material was prepared as in the above reaction scheme.

[0200] MS: [M+H] + = 631

[0202] Example 5: Preparation of Compound E5

[0203]

[0204] Compound E5 was prepared in the same manner as the preparation method of Example 1, except that each starting material was prepared as per the reaction scheme above.

[0205] MS: [M+H] + = 696

[0207] Example 6: Preparation of Compound E6

[0208]

[0209] Compound E6 was prepared in the same manner as the preparation method of Example 1, except that each starting material was prepared as per the reaction scheme above.

[0210] MS: [M+H] + = 730

[0212] Example 7: Preparation of Compound E7

[0213]

[0214] Compound E7 was prepared in the same manner as the preparation method of Example 1, except that each starting material was prepared as per the reaction scheme above.

[0215] MS: [M+H] + = 680

[0217] Example 8: Preparation of Compound E8

[0218]

[0219] Compound E8 was prepared in the same manner as the preparation method of Example 1, except that each starting material was prepared as per the reaction scheme above.

[0220] MS: [M+H] + = 757

[0222] Example 9: Preparation of Compound E9

[0223]

[0224] Compound E9 was prepared in the same manner as the preparation method of Example 1, except that each starting material was prepared as per the reaction scheme above.

[0225] MS: [M+H] + = 755

[0227] Example 10: Preparation of Compound E10

[0228]

[0229] Compound E10 was prepared in the same manner as the preparation method of Example 1, except that each starting material was prepared as per the above reaction scheme.

[0230] MS: [M+H] + = 799

[0232] Example 11: Preparation of Compound E11

[0233]

[0234] Compound E11 was prepared in the same manner as the preparation method of Example 1, except that each starting material was prepared as per the above reaction scheme.

[0235] MS: [M+H] + = 695

[0237] Example 12: Preparation of Compound E12

[0238]

[0239] Compound E12 was prepared in the same manner as the preparation method of Example 1, except that each starting material was prepared as per the reaction scheme above.

[0240] MS: [M+H] + = 782

[0242] Example 13: Preparation of Compound E13

[0243]

[0244] Compound E13 was prepared in the same manner as the preparation method of Example 1, except that each starting material was prepared as per the reaction scheme above.

[0245] MS: [M+H] + = 707

[0247] [Experimental Example]

[0248] Experimental Example 1

[0249] A glass substrate coated with an indium tin oxide (ITO) thin film to a thickness of 1,000 Å was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. products were used as the detergent, and distilled water that had been filtered twice using a Millipore Co. filter was used. After cleaning the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol as solvents, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes and then transported to a vacuum deposition machine.

[0251] A hole injection layer was formed by thermal vacuum deposition of the following compound HI-A to a thickness of 600 Å on the prepared ITO transparent electrode. A first hole transport layer and a second hole transport layer were formed by sequentially vacuum depositing the following compound HAT (50 Å) and the following compound HT-A (60 Å) on the hole injection layer.

[0253] Next, a light-emitting layer was formed by vacuum depositing the following compounds BH and BD in a weight ratio of 25:1 on the second hole transport layer with a film thickness of 200 Å.

[0255] An electron injection and transport layer with a thickness of 350 Å was formed by vacuum depositing the previously prepared compound E1 and the following compound LiQ in a weight ratio of 1:1 on the above-mentioned light-emitting layer. A cathode was formed by sequentially depositing lithium fluoride (LiF) with a thickness of 10 Å and aluminum with a thickness of 1000 Å on the above-mentioned electron injection and transport layer.

[0256]

[0258] In the above process, the deposition rate of the organic material was maintained at 0.4 Å / sec to 0.9 Å / sec, while the deposition rates of lithium fluoride and aluminum for the cathode were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 1 x 10⁻⁶ -7 torr to 5 x 10 -5 An organic light-emitting diode was fabricated by maintaining torr.

[0260] Experimental Examples 2 to 13

[0261] An organic light-emitting diode was prepared in the same manner as in Experimental Example 1 above, except that the compound of Table 1 below was used instead of compound E1.

[0263] Comparative Experiment Examples 1 to 14

[0264] An organic light-emitting diode was prepared in the same manner as in Experimental Example 1, except that the compounds in Table 1 below were used instead of compound E1. The compounds ET-1 to ET-14 used in Table 1 below are as follows.

[0265]

[0267] For the organic light-emitting diodes prepared in Experimental Examples 1 to 13 and Comparative Experimental Examples 1 to 14 above, 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm². 2 The time (T90) to reach 90% of the initial brightness at the current density was measured. The results are shown in Table 1 below.

[0269] division compound Driving voltage (V@10mA / cm²) 2 ) Efficiency (cd / A @ 10mA / cm²) 2 ) Color coordinates (x, y) Lifespan (hr) (T90@20mA / cm) 2 ) Experimental Example 1 E1 4.03 5.43 (0.140, 0.094) 189 Experimental Example 2 E2 3.95 5.54 (0.140, 0.096) 170 Experimental Example 3 E3 3.99 5.48 (0.140, 0.095) 180 Experimental Example 4 E4 3.91 5.65 (0.141, 0.094) 163 Experimental Example 5 E5 4.07 5.38 (0.140, 0.094) 208 Experimental Example 6 E6 3.97 5.56 (0.140, 0.094) 168 Experimental Example 7 E7 4.07 5.54 (0.140, 0.094) 174 Experimental Example 8 E8 4.11 5.32 (0.140, 0.096) 219 Experimental Example 9 E9 3.91 5.70 (0.140, 0.095) 151 Experimental Example 10 E10 3.95 5.59 (0.141, 0.094) 153 Experimental Example 11 E11 4.15 5.27 (0.140, 0.094) 170 Experimental Example 12 E12 4.19 5.24 (0.140, 0.094) 174 Experimental Example 13 E13 3.92 5.69 (0.141, 0.094) 150 Comparative Experiment Example 1 ET-1 4.43 4.34 (0.140, 0.096) 132 Comparative Experiment Example 2 ET-2 4.27 4.89 (0.140, 0.095) 113 Comparative Experiment Example 3 ET-3 4.19 4.98 (0.141, 0.094) 102 Comparative Experiment Example 4 ET-4 4.67 2.17 (0.140, 0.094) 76 Comparative Experiment Example 5 ET-5 4.58 2.22 (0.140, 0.094) 68 Comparative Experiment Example 6 ET-6 4.63 2.19 (0.140, 0.094) 72 Comparative Experiment Example 7 ET-7 4.53 2.26 (0.140, 0.096) 65 Comparative Experiment Example 8 ET-8 4.23 4.94 (0.140, 0.095) 38 Comparative Experiment Example 9 ET-9 4.61 2.22 (0.141, 0.094) 67 Comparative Experiment Example 10 ET-10 4.19 4.99 (0.140, 0.094) 36 Comparative Experiment Example 11 ET-11 4.77 2.13 (0.140, 0.094) 88 Comparative Experiment Example 12 ET-12 4.27 4.89 (0.140, 0.094) 42 Comparative Experiment Example 13 ET-13 4.17 5.06 (0.140, 0.094) 34 Comparative Experiment Example 14 ET-14 4.27 5.04 (0.140, 0.094) 35

[0270] As shown in Table 1 above, the compound represented by Formula 1 of the present invention can be used in an organic layer capable of simultaneously performing electron injection and electron transport of an organic light-emitting device.

[0271] When comparing Experimental Examples 1 to 13 and Comparative Experimental Examples 1 to 3 in Table 1 above, it was confirmed that the organic light-emitting device containing the compound represented by Chemical Formula 1 of the present invention exhibits superior characteristics in driving voltage, efficiency, and lifespan compared to the organic light-emitting device containing the compound in which L is naphthylene.

[0273] When comparing Experimental Examples 1 to 13 of Table 1 with Comparative Experimental Examples 4 to 7 and 9, it was confirmed that the organic light-emitting device containing the compound represented by Formula 1 of the present invention exhibits superior characteristics in driving voltage, efficiency, and lifespan compared to the organic light-emitting device containing the compound containing L-substituted or unsubstituted phenylene.

[0275] When comparing Experimental Examples 1 to 13 and Comparative Experimental Examples 8 and 10 to 14 of Table 1 above, it was confirmed that an organic light-emitting device containing a compound represented by Formula 1 of the present invention exhibits superior lifespan characteristics compared to an organic light-emitting device containing a compound in which a cyano group is not substituted. Explanation of the symbols

[0277] 1: Substrate 2: Anode 3: Emitting layer 4: Cathode 5: Hole Injection Layer 6: Hole Transport Layer 7: Electron injection and transport layer

Claims

Claim 1 Compound represented by the following chemical formula 1: [Chemical Formula 1] In the above Chemical Formula 1, L is a substituted or unsubstituted biphenyldiyl, terphenyldiyl, or quadrphenyldiyl, X is each independently N or CR1, wherein at least one of X is N, and R1 is hydrogen, deuterium, or a substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 It is an aryl, and Ar1 and Ar2 are each independently substituted or unsubstituted C 6-20 It is an aryl group, wherein at least one of Ar1 and Ar2 is substituted with one or more cyano groups, and Ar3 is a substituent represented by any one of the following chemical formulas 2-1 to 2-4, [Chemical Formula 2-1] In the above chemical formula 2-1, R3 is a substituted or unsubstituted C 1-10 Alkyl, or substituted or unsubstituted C 6-20 aryl, [Chemical Formula 2-2] In the above chemical formula 2-2, Z is O or S, and R4 are bonded to each other, forming substituted or unsubstituted C 6-20 Forms an aryl group,[Chemical Formula 2-3] In the above chemical formula 2-3, Z is O or S, and R5 is a substituted or unsubstituted C 6-20 aryl, [Chemical Formula 2-4] In the above chemical formula 2-4, Z is O or S, and R6 is a substituted or unsubstituted C 6-20 It is Aril. Claim 2 In paragraph 1, a compound, wherein L is any one selected from the group consisting of: Claim 3 A compound in which at least two of X are N, in paragraph 1. Claim 4 In paragraph 1, R1 is hydrogen, deuterium, methyl, tertbutyl, or phenyl, a compound. Claim 5 In paragraph 1, Ar1 and Ar2 are each independently a compound, which is phenyl, phenyl substituted with one or more deuterium atoms, biphenyllyl, or terphenyllyl. Claim 6 A compound according to claim 1, wherein Ar1 is phenyl or phenyl substituted with one or more deuterium groups, Ar2 is phenyl, biphenylyl, or terphenylyl, and Ar2 is substituted with one or more cyano groups. Claim 7 delete Claim 8 delete Claim 9 delete Claim 10 delete Claim 11 In claim 1, the compound represented by the above chemical formula 1 is any one selected from the group consisting of the following compounds: Claim 12 An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound according to any one of claims 1 to 6 and 11. Claim 13 An organic light-emitting device according to claim 12, wherein the organic layer is an electron injection layer, an electron transport layer, or an electron injection and transport layer.

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