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] Each X is independently N, CH, or CD, wherein at least two of X are N, and

[0017] L1 is represented by the following chemical formula 2, and

[0018] L2 is a single bond, or a substituted or unsubstituted C 6-60 It is Arilen, and

[0019] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Arilgo,

[0020] At least one of Ar1 and Ar2 is replaced with cyano, and

[0021] HAr consists of deuterium, cyano, halogen, and substituted or unsubstituted C. 1-60 Alkyl, and substituted or unsubstituted C 6-60 It is a quinazoline substituted with one or more selected from the group consisting of aryls, and

[0022] [Chemical Formula 2]

[0023]

[0024] In the above chemical formula 2,

[0025] n is an integer from 3 to 5, and

[0026] a is an integer from 0 to 4.

[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 transport and injection 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, and represents a bond connected to another substituent, and "D" represents deuterium.

[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; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy 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 is substituted or unsubstituted with a substituent in which two or more of the exemplified substituents are connected. For example, “a substituent in which two or more substituents are connected” may be a biphenyl group. In other words, a biphenylal group can be an aryl group or can be interpreted as a substituent consisting of two connected phenyl groups. For example, the term "substituted or unsubstituted" refers to "unsubstituted, or deuterium, halogen, cyano, C 1-10 Alkyl, C 1-10 Alkoxy and C 6-20 It may be understood to mean "substituted with one or more substituents selected from the group consisting of aryls"; or "unsubstituted, or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, phenyl, and naphthyl." Additionally, in this specification, the term "substituted with one or more substituents" may be understood to mean "substituted with one to the maximum number of substitutable hydrogens." Alternatively, in this specification, the term "substituted with one or more substituents" may be understood to mean "substituted with one to five substituents" or "substituted with one or two substituents."

[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 substituent 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 substituent 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 substituent having the following structure, but is not limited thereto.

[0046]

[0048] In this specification, the substituted or unsubstituted silyl group refers to -Si(Z1)(Z2)(Z3), where Z1, Z2, and Z3 are each independently hydrogen, deuterium, or substituted or unsubstituted C 1-60 Alkyl, substituted, or unsubstituted C 1-60 Haloalkyl, substituted or unsubstituted C 2-60 Alkenyl, substituted or unsubstituted C 2-60 Haloalkenyl, or substituted or unsubstituted C 6-60 It may be an aryl. According to one embodiment, Z1, Z2 and Z3 are each independently hydrogen, deuterium, substituted or unsubstituted C 1-10 Alkyl, substituted, or unsubstituted C 1-10 Haloalkyl, substituted or unsubstituted C 1-10 haloalkyl, or substituted or unsubstituted C 6-20It may be an aryl group. Specific examples of the above silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl groups.

[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 fluoro, chloro, bromo, or iodo.

[0054] In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another embodiment, 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-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, Examples include 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, but are not limited thereto.

[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 thereto.

[0058] In this specification, the alicyclic group refers to a monovalent substituent derived from a saturated or unsaturated hydrocarbon ring compound that contains only carbon as a ring-forming atom and does not have aromaticity, and is understood to encompass both monocyclic and condensed polycyclic compounds. According to one embodiment, the number of carbon atoms of the alicyclic group is 3 to 60. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to yet another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. Examples of such alicyclic groups include monocyclic groups such as cycloalkyl groups, bridged hydrocarbon groups, spiro hydrocarbon groups, and substituents derived from hydrogenated derivatives of aromatic hydrocarbon compounds.

[0060] Specifically, examples of the cycloalkyl groups include, but are not limited to, 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.

[0062] In addition, examples of the above-mentioned cross-linked hydrocarbon groups include, but are not limited to, bicyclo[1.1.0]butyl, bicyclo[2.2.1]heptyl, bicyclo[4.2.0]octa-1,3,5-trienyl, adamantyl, decalinyl, etc.

[0064] In addition, examples of the above-mentioned spiro-cyclic hydrocarbon groups include spiro[3.4]octyl and spiro[5.5]undecanyl, but are not limited thereto.

[0066] In addition, the substituent derived from the hydrogenated derivative of the above aromatic hydrocarbon compound refers to a substituent derived from a compound in which hydrogen is added to a portion of the unsaturated bonds of a monocyclic or polycyclic aromatic hydrocarbon compound, and an example of such a substituent is 1 H -Indenil, 2 H -Indenil, 4 H -Indenyl, 2,3-Dihydro-1 H -Indenyl, 1,4-Dihydronaphthalenyl, 1,2,3,4-Tetrahydronaphthalenyl, 6,7,8,9-Tetrahydro-5 H -Benzo[7]Anulenyl(6,7,8,9-tetrahydro-5 H -benzo[7]annulenyl), 6,7-dehydro-5 H Examples include benzocycloheptenyl, but are not limited to these.

[0068] In this specification, an aryl group is understood to mean a substituent derived from a monocyclic or condensed polycyclic compound having aromaticity and containing only carbon as a ring-forming atom, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60. 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.

[0070] 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.

[0072] In this specification, a heterocyclic group refers to a monovalent substituent derived from a monocyclic or condensed polycyclic compound comprising, in addition to carbon as a ring-forming atom, one or more heteroatoms selected from O, N, Si, and S, and is understood to encompass both aromatic and non-aromatic substituents. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 60. According to another embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. According to yet another embodiment, the number of carbon atoms in the heterocyclic group is 2 to 20. Examples of such heterocyclic groups include heteroaryl groups and substituents derived from hydrogenated derivatives of heteroaromatic compounds.

[0074] Specifically, the heteroaryl group refers to a substituent derived from a monocyclic or condensed polycyclic compound comprising one or more heteroatoms selected from N, O, and S in addition to carbon as a ring-forming atom, and refers to a substituent having aromaticity. According to one embodiment, the number of carbon atoms in the heteroaryl group is 2 to 60. According to another embodiment, the number of carbon atoms in the heteroaryl group is 2 to 30. According to yet another embodiment, the number of carbon atoms in the heteroaryl group is 2 to 20. Examples of the above heteroaryl groups include thiophenyl group, furanyl group, pyrroleyl group, imidazoleyl group, thiazoleyl group, oxazoleyl group, oxadiazoleyl group, triazoleyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, triazinyl group, acrridinyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, isoquinolinyl group, indoleyl group, carbazoleyl group, benzoxazoleyl group, benzimidazoleyl group, benzothiazoleyl group, benzocarbazoleyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, dibenzofuranyl group, phenanthrolinyl group, isooxazoleyl group, There are thiadiazole groups and phenothiazinyl groups, but are not limited to these.

[0076] In addition, the substituent derived from the hydrogenated derivative of the above heteroaromatic compound refers to a substituent derived from a compound in which hydrogen is added to a portion of the unsaturated bonds of a monocyclic or polycyclic heteroaromatic compound, and examples of such substituents include 1,3-dihydroisobenzofuranyl, 2,3-dihydrobenzofuranyl, 1,3-dihydrobenzo[ c ]thiophenyl(1,3-dihydrobenzo[ c ]thiophenyl), 2,3-dehydro[ b ]thiophenyl(2,3-dihydro[ b ]thiophenyl, etc., are included, but are not limited to these.

[0078] In this specification, the aryl group among the aralkyl group, ar alkenyl group, alkylaryl group, arylamine group, and arylsilyl 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 of the heteroaryl group described above may be applied to the heteroaryl group among the heteroaryl amines. 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 of the aryl group described above may be applied to the arylene group except that it is a divalent group. In this specification, the description of the heteroaryl group described above may be applied to the heteroaryl group except that the heteroarylene group is a divalent group. In this specification, the description of the aryl group or cycloalkyl group described above may be applied except that the hydrocarbon ring is not monovalent and is formed by the combination of two substituents. In this specification, the description of the aforementioned heteroaryl may apply except that the heterocycle is not monovalent and is formed by the combination of two substituents.

[0080] In this specification, the meaning of “deuterated or deuterated substituted” is that at least one of the substitutable hydrogens in the compound, the divalent linker, or the monovalent substituent is substituted with deuteration.

[0082] In addition, the meaning of “unsubstituted or substituted with deuterium” or “substituted with deuterium or unsubstituted” is “one to a maximum number of unsubstituted or substitutable hydrogens are substituted with deuterium.” For example, the term “unsubstituted or substituted with deuterium phenanthrile” can be understood to mean “unsubstituted or substituted with 1 to 9 deuterium phenanthrile,” considering that the maximum number of hydrogens that can be substituted with deuterium in the phenanthrile structure is 9.

[0084] In addition, the term "deuterated structure" means encompassing compounds of all structures in which at least one hydrogen is substituted with deuterium, divalent linkers, or monovalent substituents. For example, the deuterated structure of phenyl can be understood to refer to monovalent substituents of all structures in which at least one substitutable hydrogen within the phenyl group is substituted with deuterium, as follows.

[0085]

[0087] In addition, the "deuterium substitution rate" or "deuteriumization" of a compound refers to the ratio of the number of substituted deuterium atoms to the total number of hydrogen atoms that may exist in the compound (the sum of the number of hydrogen atoms that can be substituted for deuterium in the compound and the number of substituted deuterium atoms), calculated as a percentage. Therefore, when the "deuterium substitution rate" or "deuteriumization" of a compound is "K%", it means that K% of the hydrogen atoms that can be substituted for deuterium in the compound have been substituted with deuterium.

[0089] At this time, the above "deuterium substitution rate" or "deuterium degree" is MALDI-TOF MS (Matrix-Assisted Laser Desorption / Ionization Time-of-Flight Mass Spectrometer), nuclear magnetic resonance spectroscopy ( 1 It can be measured according to commonly known methods using 1H NMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry). More specifically, when using MALDI-TOF MS, the "deuterium substitution rate" or "deuteriumization" can be obtained by determining the number of substituted deuterium atoms in the compound through MALDI-TOF MS analysis, and then calculating the ratio of the number of substituted deuterium atoms to the total number of hydrogen atoms that may exist in the compound as a percentage.

[0091] (compound)

[0092] The present invention provides a compound represented by the above chemical formula 1.

[0094] Preferably, the above chemical formula 1 is represented by the following chemical formula 1-1:

[0095] [Chemical Formula 1-1]

[0096]

[0097] In the above chemical formula 1-1,

[0098] X, L2, Ar1, Ar2, and HAr are as defined in Chemical Formula 1 above, and

[0099] m is 2 or 3, and

[0100] a1 and a2 are each independently integers from 0 to 4.

[0102] Preferably, the above formula 1 is represented by the following formula 1-2 or formula 1-3:

[0103] [Chemical Formula 1-2]

[0104]

[0105] [Chemical Formula 1-3]

[0106]

[0107] In the above chemical formulas 1-2 and 1-3,

[0108] X, L2, Ar1, and Ar2 are as defined in Chemical Formula 1 above, and

[0109] R is substituted or unsubstituted C 6-60 Arilgo,

[0110] m is 2 or 3, and

[0111] a1, a2, b1 and b2 are each independently integers from 0 to 4.

[0112] More preferably, R is unsubstituted or cyano-substituted C 6-20 It is Aril.

[0114] More preferably, R is unsubstituted or cyano-substituted phenyl, or unsubstituted or cyano-substituted biphenylyl, and said phenyl and biphenylyl are substituted or unsubstituted with deuterium.

[0116] More preferably, R may be unsubstituted or substituted with 1 cyano and 0 to 5 deuterium phenyl, or unsubstituted or substituted with 1 cyano and 0 to 7 deuterium biphenyl.

[0118] Preferably, L1 is any one selected from the group consisting of the following and their deuteriumized structures:

[0119]

[0120] .

[0122] Preferably, L2 is a single bond, or phenylene, and said phenylene is unsubstituted or substituted with one or more deuterium atoms.

[0124] Preferably, Ar1 is unsubstituted or is a phenyl substituted with one or more deuterium atoms.

[0126] Preferably, Ar2 is phenyl or naphthyl, and said Ar2 is unsubstituted or substituted with one or more deuterium atoms.

[0128] Preferably, L2 is unsubstituted or substituted with one or more deuterium phenylenes, Ar2 is cyano-substituted phenyl or cyano-substituted naphthyl, and said Ar2 is substituted with deuterium or unsubstituted.

[0130] More preferably, L2 is unsubstituted or phenylene substituted with one or more deuterium groups; Ar2 is phenyl substituted with one cyano group or naphthyl substituted with one cyano group, and said Ar2 may be substituted with or unsubstituted with deuterium groups.

[0132] Representative examples of compounds represented by the above chemical formula 1 are as follows:

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140] .

[0142] In addition, the present invention provides a method for preparing a compound represented by Chemical Formula 1, such as the following reaction formula 1.

[0143] [Reaction Equation 1]

[0144]

[0145] In the above reaction scheme 1, X, L1, L2, Ar1, Ar2, and HAr are as previously defined, Y is a halogen, preferably bromo or chloro, and L 1a and L 1b It combines to form L1.

[0147] The compound represented by Chemical Formula 1 above can be prepared by a Suzuki-coupling reaction. In this case, it is preferable that the Suzuki-coupling reaction be carried out under a palladium catalyst and a base, and the reactor for the reaction can be changed to a reactor known in the art. This method of preparation can be further specified in the preparation examples described below.

[0149] (Organic light-emitting diode)

[0150] 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.

[0152] 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.

[0154] 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.

[0156] Additionally, the organic layer may include an electron transport layer, an electron injection layer, or a layer that performs electron transport and injection simultaneously, and the electron transport layer, the electron injection layer, or the layer that performs electron transport and injection simultaneously may include a compound represented by Chemical Formula 1.

[0158] In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron injection and transport layer, wherein the organic layer containing the compound may be an electron injection and transport layer.

[0160] 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.

[0162] 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.

[0164] 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 transport and injection layer (7), and a cathode (4). In such a structure, a compound represented by the chemical formula 1 may be included in the electron transport and injection layer.

[0166] 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.

[0168] 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.

[0170] 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.

[0172] 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.

[0174] 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.

[0176] 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.

[0178] 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.

[0180] 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.

[0182] 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.

[0184] The electron blocking layer is formed on the hole transport layer and, preferably, is provided in contact with the light-emitting layer. It refers to a layer that improves the efficiency of an organic light-emitting device by controlling hole mobility and preventing excessive movement of electrons, thereby increasing the probability of hole-electron coupling. The electron blocking layer includes an electron blocking material, and examples of such electron blocking materials may include arylamine-based organic materials, but are not limited thereto.

[0186] 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.

[0188] 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.

[0190] 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.

[0192] The hole blocking layer is formed on the light-emitting layer, preferably in contact with the light-emitting layer, and refers to a layer that improves the efficiency of an organic light-emitting device by controlling electron mobility and preventing excessive movement of holes, thereby increasing the probability of hole-electron coupling. The hole blocking layer comprises a hole blocking material, and examples of such hole blocking materials may include compounds with electron-absorbing groups such as azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; and phosphine oxide derivatives, but are not limited thereto.

[0194] The electron injection and transport layer is a layer that simultaneously performs the roles of an electron transport layer and an electron injection layer, injecting electrons from the electrode and transporting the received electrons to the light-emitting layer, and is formed on the light-emitting layer or the hole blocking layer. Suitable electron injection and transport materials are those capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, and materials with high electron mobility are suitable. Compounds represented by Chemical Formula 1 can be used as such electron injection and transport layer materials. Additional examples of electron injection and transport materials include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes; and triazine derivatives. Alternatively, it may be used with fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, etc., their derivatives, metal complex compounds, or nitrogen-containing five-membered ring derivatives, but is not limited thereto.

[0196] The electron injection and transport layer may also be formed as separate layers, such as an electron injection layer and an electron transport layer. In such cases, the electron transport layer is formed on the light-emitting layer or the hole-blocking layer, and the electron injection and transport material described above may be used as the electron transport material included in the electron transport layer. Additionally, the electron injection layer is formed on the electron transport layer, and the electron injection material included in the electron injection layer may be LiF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, etc., and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0198] 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.

[0200] In one embodiment, the electron transport layer, electron injection layer, or electron injection and transport layer of the organic light-emitting device may include the compound represented by Formula 1 and the metal complex compound together. In this case, the electron transport layer, electron injection layer, or electron injection and transport layer may include the compound represented by Formula 1 and the metal complex compound in a weight ratio of 10:90 to 90:10, a weight ratio of 30:70 to 70:30, or a weight ratio of 50:50.

[0202] The organic light-emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided emission device, and in particular may be a bottom emission device for which relatively high luminous efficiency is required.

[0204] 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.

[0206] 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.

[0208] [Example]

[0209] Example 1: Preparation of Compound E1

[0210]

[0211] Under a nitrogen atmosphere, E1-A (20 g, 38.4 mmol) and E1-B (15.7 g, 38.4 mmol) were added to 400 ml of 1,4-Dioxane and stirred and refluxed. Subsequently, tripotassium phosphate (24.4 g, 115.2 mmol) dissolved in 24 ml of water was added and stirred thoroughly, after which dibenzylideneacetone palladium (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.6 g, 2.3 mmol) were added. After reacting for 6 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 883 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. A white solid compound E1 (4.4 g, 15%) was prepared by recrystallizing the concentrated compound with chloroform and ethyl acetate.

[0212] MS: [M+H] + = 767

[0214] Example 2: Preparation of Compound E2

[0215]

[0216] 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.

[0217] MS: [M+H] + = 767

[0219] Example 3: Preparation of Compound E3

[0220]

[0221] 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.

[0222] MS: [M+H] + = 767

[0224] Example 4: Preparation of Compound E4

[0225]

[0226] 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.

[0227] MS: [M+H] + = 817

[0229] Example 5: Preparation of Compound E5

[0230]

[0231] 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.

[0232] MS: [M+H] + = 767

[0234] Example 6: Preparation of Compound E6

[0235]

[0236] 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.

[0237] MS: [M+H] + = 766

[0239] Example 7: Preparation of Compound E7

[0240]

[0241] 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 above reaction scheme.

[0242] MS: [M+H] + = 767

[0244] Example 8: Preparation of Compound E8

[0245]

[0246] 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 above reaction scheme.

[0247] MS: [M+H] + = 767

[0249] Example 9: Preparation of Compound E9

[0250]

[0251] 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 above reaction scheme.

[0252] MS: [M+H] + = 767

[0254] Example 10: Preparation of Compound E10

[0255]

[0256] 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.

[0257] MS: [M+H] + = 767

[0259] Example 11: Preparation of Compound E11

[0260]

[0261] 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 reaction scheme above.

[0262] MS: [M+H] + = 867

[0264] Example 12: Preparation of Compound E12

[0265]

[0266] 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.

[0267] MS: [M+H] + = 772

[0269] [Experimental Example]

[0270] Experimental Example 1

[0271] 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 Millerpore 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.

[0273] A hole injection layer was formed by thermal vacuum deposition of the following compound HI-A to a thickness of 600 Å on the ITO transparent electrode prepared in this way. A hole transport layer was formed by sequentially vacuum depositing hexaazatriphenylene (HAT, 50 Å) of the following chemical formula and the following compound HT-A (600 Å) on the hole injection layer.

[0275] 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 hole transport layer to a film thickness of 200 Å. On the light-emitting layer, an electron transport and injection layer with a thickness of 360 Å was formed by vacuum depositing the compound E1 prepared in Example 1 and the following compound LiQ (Lithium quinolate) in a weight ratio of 1:1. On the electron transport and injection layer, a cathode was formed by sequentially depositing lithium fluoride (LiF) with a thickness of 10 Å and aluminum with a thickness of 1,000 Å.

[0276]

[0278] In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, while the deposition rates for lithium fluoride and aluminum at the cathode were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 1 × 10⁻⁶ -7 ~ 5 × 10 -8 An organic light-emitting diode was fabricated by maintaining torr.

[0280] Experimental Examples 2 to 12

[0281] An organic light-emitting diode was prepared in the same manner as in Experimental Example 1, except that the compound of Table 1 below was used instead of compound E1 of Experimental Example 1.

[0283] Comparative Experiment Examples 1 to 8

[0284] 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 of Experimental Example 1. The compounds ET-1 to ET-8 used in Table 1 below are as follows.

[0285]

[0287] For the organic light-emitting diodes prepared in the above experimental and comparative experimental examples, 10 mA / cm 2 The driving voltage, luminous efficiency, and color coordinates were measured at a current density of 20 mA / cm². 2 The time (T90) to reach 90% of the initial brightness at a current density was measured. The results are shown in Table 1 below.

[0289] Compound (electron transport and injection layer) Voltage (V@10mA / cm²) 2 ) Efficiency (cd / A @ 10mA / cm²) 2 ) Color coordinates (x,y) T90(hr@20mA / cm 2 ) Experimental Example 1 E1 4.02 4.58 (0.136, 0.112) 213 Experimental Example 2 E2 3.98 4.65 (0.136, 0.111) 192 Experimental Example 3 E3 4.06 4.69 (0.136, 0.112) 196 Experimental Example 4 E4 4.14 4.49 (0.136, 0.111) 226 Experimental Example 5 E5 3.98 4.68 (0.136, 0.111) 200 Experimental Example 6 E6 4.12 4.40 (0.136, 0.111) 179 Experimental Example 7 E7 4.14 4.67 (0.136, 0.112) 185 Experimental Example 8 E8 4.18 4.62 (0.136, 0.111) 196 Experimental Example 9 E9 4.14 4.69 (0.136, 0.112) 181 Experimental Example 10 E10 3.94 4.53 (0.136, 0.111) 200 Experimental Example 11 E11 4.26 4.26 (0.136, 0.111) 256 Experimental Example 12 E12 4.02 4.58 (0.136, 0.112) 234 Comparative Experiment Example 1 ET-1 4.34 4.12 (0.136, 0.111) 30 Comparative Experiment Example 2 ET-2 5.17 2.79 (0.136, 0.111) 27 Comparative Experiment Example 3 ET-3 4.42 3.66 (0.136, 0.112) 170 Comparative Experiment Example 4 ET-4 4.38 3.72 (0.136, 0.111) 153 Comparative Experiment Example 5 ET-5 4.47 3.75 (0.136, 0.112) 157 Comparative Experiment Example 6 ET-6 4.55 3.59 (0.136, 0.111) 174 Comparative Experiment Example 7 ET-7 4.33 4.13 (0.136, 0.111) 29 Comparative Experiment Example 8 ET-8 4.30 4.15 (0.136, 0.111) 31

[0290] As described in Table 1 above, it was confirmed that an organic light-emitting device using a compound represented by Formula 1 of the present invention exhibits excellent characteristics in voltage, efficiency, and / or lifetime (T90).

[0291] When comparing Experimental Examples 1 to 12 of Table 1 above with Comparative Experimental Examples 1, 7, and 8, it was confirmed that the organic light-emitting device containing the compound of Formula 1 of the present invention exhibits significantly superior characteristics in terms of lifespan compared to the organic light-emitting device using a compound in which the cyano group is not substituted.

[0293] When comparing Experimental Examples 1 to 12 and Comparative Experimental Examples 2 to 6 in Table 1 above, it was confirmed that the organic light-emitting device containing the compound of Formula 1 of the present invention exhibits significantly superior characteristics in terms of efficiency compared to the organic light-emitting device using the compound of Formula 2 in which n is 2 or less. Explanation of the symbols

[0295] 1: Substrate 2: Anode 3: Emitting layer 4: Cathode 5: Hole Injection Layer 6: Hole Transport Layer 7: Electron transport and injection layer

Claims

Claim 1 Compound represented by the following chemical formula 1-1: [Chemical Formula 1-1] In the above Chemical Formula 1, X is each independently N, CH, or CD, wherein at least two of X are N, and L2 is a single bond, or a substituted or unsubstituted C 6-60 It is arylene, and Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 It is an aryl, and at least one of Ar1 and Ar2 is substituted with cyano, and HAr is deuterium, cyano, halogen, substituted or unsubstituted C 1-60 Alkyl, and substituted or unsubstituted C 6-60 It is a quinazolin substituted with one or more selected from the group consisting of aryls, m is 2 or 3, and a1 and a2 are each independently integers from 0 to 4. Claim 2 delete Claim 3 In claim 1, the compound: [Chemical Formula 1-2], wherein Chemical Formula 1-1 is represented by the following Chemical Formula 1-2 or Chemical Formula 1-3. [Chemical Formula 1-3] In the above chemical formulas 1-2 and 1-3, X, L2, Ar1, and Ar2 are as defined in claim 1, and R is a substituted or unsubstituted C 6-60 It is an aryl, m is 2 or 3, and a1, a2, b1 and b2 are each independently integers from 0 to 4. Claim 4 In paragraph 1, L1 is a compound selected from the group consisting of the following and any one of their deuteriumized structures: . Claim 5 A compound according to claim 1, wherein L2 is a single bond or phenylene, and said phenylene is unsubstituted or substituted with one or more deuterium atoms. Claim 6 In paragraph 1, Ar1 is a compound of phenyl that is unsubstituted or substituted with one or more deuterium atoms. Claim 7 A compound according to claim 1, wherein Ar2 is phenyl or naphthyl, and said Ar2 is unsubstituted or substituted with one or more deuterium atoms. Claim 8 In claim 1, L2 is unsubstituted or substituted with one or more deuterium phenylene, Ar2 is cyano-substituted phenyl or cyano-substituted naphthyl, and said Ar2 is substituted with or unsubstituted with deuterium, a compound. Claim 9 In paragraph 3, R is an unsubstituted or cyano-substituted phenyl, or an unsubstituted or cyano-substituted biphenylyl, and said phenyl and biphenylyl are substituted or unsubstituted with deuterium, a compound. Claim 10 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 11 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 and 3 to 10. Claim 12 An organic light-emitting device according to claim 11, wherein the organic layer containing the above compound is an electron transport layer, an electron injection layer, or an electron transport and injection layer.

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