Novel compound and organic light-emitting device containing the same

Abstract

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

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of priority based on Korean Patent Application No. 10-2022-0112123, filed September 5, 2022, and all contents disclosed in the documents of said Korean patent application are incorporated herein by reference.

[0002] The present invention relates to a novel compound and an organic light-emitting device containing the compound. [Background technology]

[0003] Generally, organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices utilizing organic light-emitting phenomenon have a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and are the subject of much research.

[0004] Organic light-emitting devices generally have a structure including an anode, a cathode, and an organic material layer between the anode and the cathode. The organic material layer is often a multi-layer structure composed of different materials to enhance the efficiency and stability of the organic light-emitting device, and includes, for example, a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in this organic light-emitting device, holes are injected from the anode and electrons are injected from the cathode into the organic material layer. When the injected holes and electrons meet, excitons are formed, and when the excitons return to their ground state, light is emitted.

[0005] There is a continuous demand for the development of new organic materials for use in such organic light-emitting devices. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Korean Patent Publication No. 10-2000-0051826 Summary of the Invention [Problem to be solved by the invention]

[0007] The present invention relates to a novel compound and an organic light-emitting device containing the compound. [Means for solving the problem]

[0008] The present invention provides a compound represented by the following formula 1: [ka]

[0009] In the above Chemical Formula 1, X's are each independently N, CH, or CD, and at least two of X's are N; L is a single bond or a substituted or unsubstituted C 6-60 is an arylene, Ar1 and Ar2 are each independently a substituted or unsubstituted C 6-60 is aryl, Ar3 and Ar4 are each independently an unsubstituted or substituted phenyl with one or more deuterium atoms; Any one of Ar1 to Ar4 is substituted with cyano; HAr is unsubstituted or deuterium, substituted or unsubstituted C 1-60 Alkyl, and substituted or unsubstituted C 6-60 pyrimidinyl substituted by 1 to 3 substituents independently selected from the group consisting of aryl; substituted or unsubstituted, two C 6-60 aryl-substituted triazinyl; or substituted or unsubstituted, one C 6-60 aryl-substituted quinazolinyl; a and b each independently represent an integer of 0 to 4; n and m are each independently 0 or 1; However, n+m is 1, a+n is an integer from 0 to 4, b+m is an integer from 0 to 4.

[0010] The present invention also provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. [Effects of the Invention]

[0011] The compound represented by Chemical Formula 1 can be used as a material for an organic layer of an organic light-emitting device, and can improve the efficiency, low driving voltage, and / or life characteristics of the organic light-emitting device. In particular, the compound represented by Chemical Formula 1 can be used as a hole injection material, hole transport material, hole injection and transport material, light-emitting material, electron transport material, or electron injection material. [Brief explanation of the drawings]

[0012] [Figure 1] FIG. 1 is a diagram showing an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. [Figure 2] 1 is a diagram showing an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an emitting layer 3, an electron transport and injection layer 7, and a cathode 4. FIG. DETAILED DESCRIPTION OF THE INVENTION

[0013] The present invention will be explained in more detail below for better understanding.

[0014] In this specification, [ka] and [ka] denotes a bond that is connected to another substituent, and "D" denotes deuterium.

[0015] As used herein, the term "substituted or unsubstituted" refers to a group consisting of deuterium, halogen, cyano, nitro, hydroxy, carbonyl, ester, imide, amino, phosphine oxide, alkoxy, aryloxy, alkylthioxy, arylthioxy, alkylsulfoxy, arylsulfoxy, silyl, boron, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, aralkenyl, alkylaryl, alkylamine, aralkylamine, heteroarylamine, arylamine, arylphosphine, or a heterocyclic group containing one or more N, O, and S atoms, or a group consisting of two or more of the above-listed substituents linked together. For example, a "substituent linked to two or more substituents" may be a biphenylyl group. In other words, a biphenylyl group may be an aryl group, and is interpreted as a substituent linked to two phenyl groups. As an example, the term "substituted or unsubstituted" means "unsubstituted or substituted with deuterium, halogen, cyano, C 1-10 Alkyl, C 1-10 Alkoxy and C 6-20 aryl"; or "unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, phenyl, and naphthyl." In addition, in this specification, the term "substituted with one or more substituents" is understood to mean "substituted with from 1 to the maximum number of substitutable hydrogens." Alternatively, in this specification, the term "substituted with one or more substituents" is understood to mean "substituted with 1 to 5 substituents" or "substituted with 1 or 2 substituents."

[0016] In this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but preferably is 1 to 40. Specifically, the carbonyl group may be a substituent having the structure shown below, but is not limited thereto. [ka]

[0017] In this specification, the oxygen atom of the ester group may be substituted with a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a substituent having the following structural formula, but is not limited thereto. [ka]

[0018] In this specification, the number of carbon atoms of the imide group is not particularly limited, but preferably is 1 to 25. Specifically, the imide group may have a substituent having the following structure, but is not limited thereto. [ka]

[0019] As used herein, a substituted or unsubstituted silyl group refers to -Si(Z1)(Z2)(Z3), where Z1, Z2, and Z3 are each independently hydrogen, deuterium, 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 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 C6-20 Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0020] In this specification, specific examples of the boron group include, but are not limited to, a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group.

[0021] As used herein, examples of halogen groups include fluoro, chloro, bromo, or iodo.

[0022] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethylpropyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethyl ... butyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, and the like.

[0023] In this specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms in 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, and styrenyl group, but are not limited to these.

[0024] In this specification, the term "alicyclic group" refers to a monovalent substituent derived from a saturated or unsaturated hydrocarbon ring compound that contains only carbon atoms as ring-forming atoms and has no aromaticity, and is understood to encompass all monocyclic and condensed polycyclic compounds. According to one embodiment, the aliphatic ring group has 3 to 60 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. Examples of such aliphatic ring groups include monocyclic groups such as cycloalkyl groups, bridged hydrocarbon groups, spiro hydrocarbon groups, and substituents derived from hydrogenated derivatives of aromatic hydrocarbon compounds.

[0025] Specific examples of the cycloalkyl group 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, and cyclooctyl.

[0026] Examples of the bridged hydrocarbon group 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, and decalinyl.

[0027] Examples of the spirocyclic hydrocarbon group include, but are not limited to, spiro[3.4]octyl and spiro[5.5]undecanyl.

[0028] Furthermore, the substituent derived from a hydrogenated derivative of an aromatic hydrocarbon compound refers to a substituent derived from a compound in which hydrogen has been added to part of the unsaturated bond of a monocyclic or polycyclic aromatic hydrocarbon compound. Examples of such a substituent include, but are not limited to, 1H-indenyl, 2H-indenyl, 4H-indenyl, 2,3-dihydro-1H-indenyl, 1,4-dihydronaphthalenyl, 1,2,3,4-tetrahydronaphthalenyl, 6,7,8,9-tetrahydro-5H-benzo[7]annulenyl, and 6,7-dihydro-5H-benzocycloheptenyl.

[0029] In this specification, the term "aryl group" refers to a substituent derived from a monocyclic or fused polycyclic compound containing only carbon atoms as ring-forming atoms and having aromaticity. The number of carbon atoms is not particularly limited, but preferably ranges from 6 to 60. According to one embodiment, the number of carbon atoms in the aryl group is from 6 to 30. According to one embodiment, the number of carbon atoms in the aryl group is from 6 to 20. The monocyclic aryl group may be, for example, a phenyl group, a biphenylyl group, or a terphenylyl group, but is not limited thereto. The polycyclic aryl group may be, for example, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, or a fluorenyl group, but is not limited thereto.

[0030] In this specification, the fluorenyl group may be substituted, and two of the substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted, [ka] However, the present invention is not limited to these.

[0031] As used herein, the term "heterocyclic group" refers to a monovalent substituent derived from a monocyclic or fused polycyclic compound containing, in addition to carbon, one or more heteroatoms selected from O, N, Si, and S as ring-forming atoms, and is understood to encompass both aromatic and non-aromatic substituents. According to one embodiment, the heterocyclic group has 2 to 60 carbon atoms. According to another embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to another embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of such heterocyclic groups include heteroaryl groups and substituents derived from hydrogenated derivatives of heteroaromatic compounds.

[0032] Specifically, the heteroaryl group refers to a substituent derived from a monocyclic or fused polycyclic compound containing, in addition to carbon, one or more heteroatoms selected from N, O, and S as ring-forming atoms, and refers to a substituent having aromaticity. According to one embodiment, the heteroaryl group has 2 to 60 carbon atoms. According to another embodiment, the heteroaryl group has 2 to 30 carbon atoms. According to another embodiment, the heteroaryl group has 2 to 20 carbon atoms. Examples of the heteroaryl group include, but are not limited to, a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridinyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, an isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuranyl group, a dibenzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, and a phenothiazinyl group.

[0033] Furthermore, the substituent derived from a hydrogenated derivative of a heteroaromatic compound refers to a substituent derived from a compound in which hydrogen has been added to part of the unsaturated bond of a monocyclic or polycyclic heteroaromatic compound. Examples of such a substituent include, but are not limited to, 1,3-dihydroisobenzofuranyl, 2,3-dihydrobenzofuranyl, 1,3-dihydrobenzo[c]thiophenyl, and 2,3-dihydro[b]thiophenyl.

[0034] Herein, the aryl groups in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl group are as exemplified above for the aryl group. Herein, the alkyl groups in the aralkyl group, alkylaryl group, and alkylamine group are as exemplified above for the alkyl group. Herein, the heteroaryl in the heteroarylamine is as exemplified above for the heteroaryl. Herein, the alkenyl group in the aralkenyl group is as exemplified above for the alkenyl group. Herein, the aryl group is as exemplified above for the arylene, except that it is a divalent group. Herein, the heteroaryl is as exemplified above for the heteroarylene, except that it is a divalent group. Herein, the hydrocarbon group is as exemplified above for the aryl group or cycloalkyl group, except that it is not a monovalent group but is formed by the bonding of two substituents. Herein, the heterocycle is as exemplified above for the heteroaryl, except that it is not a monovalent group but is formed by the bonding of two substituents.

[0035] As used herein, the term "deuterated or substituted with deuterium" means that at least one substitutable hydrogen atom in a compound, a divalent linking group, or a monovalent substituent is substituted with deuterium.

[0036] Furthermore, the terms "unsubstituted or substituted with deuterium" or "substituted or unsubstituted with deuterium" mean "unsubstituted, or one to the maximum number of substitutable hydrogen atoms are substituted with deuterium." For example, the term "unsubstituted or deuterium-substituted phenanthryl" can be understood to mean "unsubstituted or substituted with one to nine deuterium atoms," considering that the maximum number of hydrogen atoms that can be substituted with deuterium in the phenanthryl structure is nine.

[0037] Furthermore, the term "deuterated structure" encompasses all compounds, divalent linking groups, or monovalent substituents in which at least one hydrogen atom has been replaced with deuterium. For example, a deuterated structure of phenyl is understood to refer to all monovalent substituents in which at least one substitutable hydrogen atom in the phenyl group has been replaced with deuterium, as shown below. [ka]

[0038] Furthermore, the "deuterium substitution rate" or "degree of deuteration" of a compound refers to the ratio, calculated as a percentage, of the number of substituted deuterium atoms to the total number of hydrogen atoms that can be present in the compound (the sum of the number of hydrogen atoms in the compound that can be substituted with deuterium and the number of substituted deuterium atoms). Therefore, when the "deuterium substitution rate" or "degree of deuteration" of a compound is "K%," it means that K% of the hydrogen atoms in the compound that can be substituted with deuterium have been substituted with deuterium.

[0039] In this case, the "deuterium substitution rate" or "degree of deuteration" can be measured by MALDI-TOF MS (Matrix-Assisted Laser Desorption / Ionization Time-of-Flight Mass Spectrometer), nuclear magnetic resonance spectroscopy ( 1 The deuterium content can be measured by a commonly known method using 1H NMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), GC / MS (Gas Chromatography / Mass Spectrometry), etc. More specifically, when MALDI-TOF MS is used, the "deuterium substitution rate" or "degree of deuteration" can be determined by determining the number of deuterium atoms substituted in a compound by MALDI-TOF MS analysis, and then calculating the ratio of the number of substituted deuterium atoms to the total number of hydrogen atoms that can be present in the compound as a percentage.

[0040] (compound) The present invention provides a compound represented by Chemical Formula 1.

[0041] Preferably, the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3: [ka] [ka]

[0042] In the above chemical formulas 1-1 to 1-3, X, L, Ar1, Ar2, Ar3, Ar4, a, b, n and m are as defined above; Y is N or CR' and at least two of Y are N; R' is hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 is aryl, R1 and R2 are each independently a substituted or unsubstituted C 6-60 is aryl, c is an integer of 0 to 4.

[0043] Preferably, the chemical formula 1 is represented by any one of the following chemical formulas 1-4 to 1-9: [ka] [ka] [ka]

[0044] In the chemical formulas 1-4 to 1-9, X, L, Ar1, Ar2, Ar3, Ar4, HAr, a, and b are as defined above.

[0045] Preferably, L is a single bond, phenylene, or biphenyldiyl; The phenylene and biphenyldiyl are unsubstituted or substituted with one or more deuterium atoms.

[0046] Preferably, Ar1 is phenyl which is unsubstituted or substituted with one or more deuterium atoms.

[0047] Preferably, Ar2 is phenyl, biphenylyl, or naphthyl, said Ar2 being unsubstituted or substituted with one or more deuterium atoms.

[0048] Preferably, L is phenylene or biphenyldiyl, wherein said L is unsubstituted or substituted with one or more deuterium atoms; Ar2 is cyano-substituted phenyl or cyano-substituted naphthyl, wherein said Ar2 is deuterium-substituted or unsubstituted.

[0049] More preferably, L is unsubstituted or substituted with one or more deuterium atoms in phenylene, or unsubstituted or substituted with one or more deuterium atoms in biphenyldiyl; and Ar2 is phenyl substituted with one cyano and 0 to 4 deuterium atoms, or naphthyl substituted with one cyano and 0 to 6 deuterium atoms.

[0050] Preferably, L is a single bond; Ar2 is phenyl or biphenylyl, wherein said Ar2 is unsubstituted or substituted with one or more deuterium atoms; Ar3 is phenyl substituted with cyano, wherein said Ar3 is deuterium substituted or unsubstituted.

[0051] More preferably, L is a single bond; Ar2 is unsubstituted or substituted with one or more deuterium atoms in phenyl, or unsubstituted or substituted with one or more deuterium atoms in biphenylyl; and Ar3 is phenyl substituted with one cyano and 0 to 4 deuterium atoms.

[0052] Preferably, R' is hydrogen, deuterium, or methyl which is unsubstituted or substituted with one or more deuterium atoms.

[0053] Preferably, R1 and R2 are each independently phenyl, biphenylyl, or naphthyl, and said R1 and R2 are unsubstituted or substituted with one or more deuterium atoms.

[0054] Representative examples of the compound represented by Chemical Formula 1 are as follows: [ka] [ka] [ka] [ka] [ka] [ka] [ka] .

[0055] The present invention also provides a method for preparing the compound represented by Chemical Formula 1, such as the following Reaction Scheme 1: [ka] In the above reaction scheme 1, X, L, Ar1, Ar2, Ar3, Ar4, HAr, a, b, n, and m are as defined above, and Y is a halogen, preferably bromo or chloro.

[0056] The compound represented by Formula 1 can be prepared by Suzuki-coupling reaction. Preferably, the Suzuki-coupling reaction is carried out in the presence of a palladium catalyst and a base, and the reactive group for the reaction can be changed to a reactive group known in the art. This preparation method will be further exemplified in the preparation examples described below.

[0057] (organic light-emitting element) The present invention also provides an organic light-emitting device comprising a compound represented by Chemical Formula 1. As an 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 material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1.

[0058] The organic material layer of the organic light-emitting device of the present invention may have a single-layer structure or a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, an electron transport layer, an electron injection layer, etc. as the organic material layer. However, the structure of the organic light-emitting device is not limited thereto and may include fewer organic layers.

[0059] The organic material layer may include an emitting layer, and the emitting layer may include the compound represented by Chemical Formula 1. In particular, the compound according to the present invention may be used as a dopant in the emitting layer.

[0060] Furthermore, the organic layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the electron transport layer, electron injection layer, or layer that simultaneously performs electron transport and electron injection may include a compound represented by Chemical Formula 1.

[0061] Furthermore, the organic layer may include a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport and injection layer, and in this case, the organic layer containing the compound may be an electron transport and injection layer.

[0062] The organic light-emitting device according to the present invention may also be a normal-type organic light-emitting device having an anode, one or more organic material layers, and a cathode stacked in sequence on a substrate. The organic light-emitting device according to the present invention may also be an inverted-type organic light-emitting device having an anode, one or more organic material layers, and an anode stacked in sequence on a substrate. For example, the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.

[0063] FIG. 1 is a diagram showing an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

[0064] In this structure, the compound represented by Chemical Formula 1 is contained in the light-emitting layer.

[0065] 2 is a diagram showing 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, an emitting layer 3, an electron transport and injection layer 7, and a cathode 4. In this structure, the compound represented by Chemical Formula 1 is contained in the electron transport and injection layer.

[0066] The organic light emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic material layers contains the compound represented by Chemical Formula 1. Furthermore, when the organic light emitting device includes multiple organic material layers, the organic material layers may be formed of the same material or different materials.

[0067] For example, an organic light-emitting device according to the present invention can be fabricated by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. Here, a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation can be used to deposit a metal, conductive metal oxide, or alloy thereof on a substrate to form an anode, followed by forming organic layers including a hole injection layer, a hole transport layer, an emissive layer, and an electron transport layer, and then depositing a material usable as a cathode on the organic layer. Alternatively, an organic light-emitting device can be fabricated by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0068] In addition, the compound represented by Chemical Formula 1 can be formed into an organic layer by a solution coating method as well as a vacuum deposition method during the manufacture of an organic light emitting device, where the solution coating method includes, but is not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc.

[0069] In addition to this method, an organic light emitting device can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (WO2003 / 012890), but the manufacturing method is not limited to this.

[0070] As an example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

[0071] The anode material is preferably a material with a high work function to facilitate hole injection into the organic layer. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0072] The cathode material is preferably a material with a small work function so as to facilitate electron injection into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO / Al.

[0073] The hole injection layer is a layer that injects holes from the electrode. The hole injection material preferably has the ability to transport holes, thereby providing excellent hole injection from the anode and hole injection into the light-emitting layer or light-emitting material. It also preferably prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material. It is also preferable that the HOMO (highest occupied molecular orbital) of the hole injection material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile hexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinone, and polyaniline and polythiophene-based conductive polymers.

[0074] The hole transport layer receives holes from the hole injection layer and transports them to the light emitting layer. The hole transport material is preferably a material that can transport holes from the anode or the hole injection layer to the light emitting layer and has high hole mobility. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0075] The light-emitting material is preferably a material that can emit light in the visible light range by combining holes and electrons transported from the hole transport layer and electron transport layer, and has good quantum efficiency for fluorescence or phosphorescence. Specific examples include, but are not limited to, 8-hydroxyquinoline aluminum complex (Alq3), carbazole compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole, and benzimidazole compounds, poly(p-phenylenevinylene) (PPV) polymers, spiro compounds, polyfluorene, and rubrene.

[0076] The light-emitting layer may include a host material and a dopant material. The host material may be a fused aromatic ring derivative or a heterocyclic ring-containing compound. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocyclic ring-containing compound include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives.

[0077] Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include fused aromatic ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, chrysene, and periflanthene. Styrylamine compounds include substituted or unsubstituted arylamines substituted with at least one arylvinyl group, which may be substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamino groups. Specific examples include, but are not limited to, styrylamines, styryldiamines, styryltriamines, and styryltetraamines. Metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0078] The electron injection and transport layer functions simultaneously as both an electron transport layer and an electron injection layer, injecting electrons from the cathode and transporting the received electrons to the light-emitting layer. It is formed on the light-emitting layer or the hole-blocking layer. Such electron injection and transport materials are preferably materials that can efficiently inject electrons from the cathode and transfer them to the light-emitting layer, and have high electron mobility. The compound represented by Chemical Formula 1 can be used as the electron injection and transport layer material. Examples of additional electron injection and transport materials include, but are not limited to, 8-hydroxyquinoline Al complexes; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes; and triazine derivatives. Alternatively, the electron injection and transport layer may be used in combination with fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthrone, and their derivatives, metal complex compounds, or nitrogen-containing five-membered ring derivatives.

[0079] The electron injection and transport layers may be formed as separate layers. In this case, the electron transport layer is formed on the light-emitting layer or the hole-blocking layer, and the electron transport material contained in the electron transport layer may be any of the electron injection and transport materials described above. Alternatively, the electron injection layer may be formed on the electron transport layer, and the electron injection material may be LiF, NaCl, CsF, LiO, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthrone, or their derivatives, metal complex compounds, or nitrogen-containing five-membered ring derivatives.

[0080] Examples of the metal complex compounds include, but are not limited to, 8-hydroxyquinolinatolithium, 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-hydroxyquinolinato)chlorogallium, bis(2-methyl-8-hydroxyquinolinato)(o-cresolato)gallium, bis(2-methyl-8-hydroxyquinolinato)(1-naphtholate)aluminum, and bis(2-methyl-8-hydroxyquinolinato)(2-naphtholate)gallium.

[0081] 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 Chemical 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 Chemical 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.

[0082] 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 may be a bottom emission device which requires relatively high luminous efficiency.

[0083] Furthermore, the compound according to the present invention may be contained in an organic solar cell or an organic transistor in addition to the organic light-emitting device.

[0084] The compound represented by Formula 1 and the preparation of an organic light-emitting device including the same will be described in detail in the following examples. However, the following examples are for illustrative purposes only and the scope of the present invention is not limited thereto. [Example]

[0085] [Example] Example 1: Preparation of Compound E1 [ka] Under a nitrogen atmosphere, E1-A (20 g, 38.4 mmol) and E1-B (16.7 g, 38.4 mmol) were added to 400 mL of 1,4-dioxane and stirred under reflux. After this, potassium phosphate tribasic (24.4 g, 115.2 mmol) dissolved in 24 mL of water was added. After thorough stirring, dibenzylideneacetone palladium (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.6 g, 2.3 mmol) were added. After 7 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 914 mL of chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce white solid compound E1 (4.6 g, 15%). MS: [M+H] + =794

[0086] Example 2: Preparation of Compound E2 [ka] The compound E2 was prepared in the same manner as in Example 1, except that the starting materials were used as shown in the reaction scheme. MS: [M+H] + =794

[0087] Example 3: Preparation of Compound E3 [ka] The compound E3 was prepared in the same manner as in Example 1, except that the starting materials were used as shown in the reaction scheme. MS: [M+H] + =794

[0088] Example 4: Preparation of Compound E4 [ka] Compound E4 was prepared in the same manner as in Example 1, except that the starting materials were used as shown in the reaction scheme. MS: [M+H] + =844

[0089] Example 5: Preparation of Compound E5 [ka] Compound E5 was prepared in the same manner as in Example 1, except that the starting materials were used as shown in the reaction scheme. MS: [M+H] + =718

[0090] Example 6: Preparation of Compound E6 [ka] Compound E6 was prepared in the same manner as in Example 1, except that the starting materials were used as shown in the reaction scheme. MS: [M+H] +=718

[0091] Example 7: Preparation of Compound E7 [ka] Compound E7 was prepared in the same manner as in Example 1, except that the starting materials were used as shown in the reaction scheme. MS: [M+H] + =794

[0092] Example 8: Preparation of Compound E8 [ka] Compound E8 was prepared in the same manner as in Example 1, except that the starting materials were used as shown in the reaction scheme. MS: [M+H] + =767

[0093] Example 9: Preparation of Compound E9 [ka] The compound E9 was prepared in the same manner as in Example 1, except that the starting materials were used as shown in the reaction scheme. MS: [M+H] + =767

[0094] Example 10: Preparation of Compound E10 [ka] The compound E10 was prepared in the same manner as in Example 1, except that the starting materials were used as shown in the reaction scheme. MS: [M+H] + =843

[0095] Example 11: Preparation of Compound E11 [ka] The compound E11 was prepared in the same manner as in Example 1, except that the starting materials were used as shown in the reaction scheme. MS: [M+H] + =793

[0096] Example 12: Preparation of Compound E12 [ka] The compound E12 was prepared in the same manner as in Example 1, except that the starting materials were used as shown in the reaction scheme. MS: [M+H] + =767

[0097] Example 13: Preparation of Compound E13 [ka] The compound E13 was prepared in the same manner as in Example 1, except that the starting materials were used as shown in the reaction scheme. MS: [M+H] + =799

[0098] [Experimental Example] Experimental Example 1 A glass substrate coated with a 1,000Å-thick thin film of ITO (indium tin oxide) was ultrasonically cleaned in distilled water containing a detergent. The detergent used was a product of Fischer Co., and the distilled water was filtered through a Millipore Co. filter. After cleaning the ITO for 30 minutes, it was ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning, it was ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned using oxygen plasma for 5 minutes before being transferred to a vacuum deposition machine.

[0099] On the ITO transparent electrode thus prepared, a hole injection layer was formed by thermal vacuum deposition of the following compound HI-A to a thickness of 600 Å. On the hole injection layer, hexaazatriphenylene (HAT, 50 Å) of the following chemical formula and the following compound HT-A (600 Å) were sequentially vacuum deposited to form a hole transport layer.

[0100] Next, on the hole transport layer, the following compounds BH and BD were vacuum-deposited in a weight ratio of 25:1 to form an emitting layer with a thickness of 200 Å. On the emitting layer, compound E1 prepared in Example 1 and the following compound LiQ (lithium quinolate) were vacuum-deposited in a weight ratio of 1:1 to form an electron transport and injection layer with a thickness of 360 Å. On the electron transport and injection layer, lithium fluoride (LiF) was sequentially deposited in a thickness of 10 Å and aluminum in a thickness of 1,000 Å to form a cathode.

[0101] [ka]

[0102] During the above process, the deposition rate of the organic material was maintained at 0.4-0.9 Å / sec, the deposition rate of the cathode lithium fluoride was maintained at 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. The vacuum level during deposition was 1×10 -7 ~5×10 -8 The organic light-emitting device was fabricated while maintaining the pressure of torr.

[0103] Experimental Examples 2-13 An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound in Table 1 below was used instead of Compound E1 in Experimental Example 1.

[0104] Comparative Experimental Examples 1-13 An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compounds in Table 1 below were used instead of Compound E1 in Experimental Example 1. Compounds ET-A to ET-M used in Table 1 below are as follows.

[0105] [ka]

[0106] For the organic light-emitting devices manufactured in the above experimental examples 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 / cm 2 The time (T90) required for the luminance to reach 90% of the initial luminance was measured at a current density of 100 Hz. The results are shown in Table 1 below.

[0107] [Table 1]

[0108] As shown in Table 1, it was confirmed that the organic light emitting device using the compound represented by Chemical Formula 1 of the present invention exhibited excellent characteristics in terms of voltage, efficiency and / or lifetime (T90).

[0109] Comparing Experimental Examples 1 to 13 with Comparative Experimental Examples 1, 2, 4 to 6, 8, 12 and 13 in Table 1, it was confirmed that an organic light-emitting device including the compound of Chemical Formula 1 of the present invention exhibits significantly superior properties in terms of efficiency compared to organic light-emitting devices using compounds with different substituents between heterocyclic groups.

[0110] Comparing Experimental Examples 1 to 13 with Comparative Experimental Examples 3 and 10 in Table 1, it was confirmed that the organic light emitting device containing the compound of Chemical Formula 1 of the present invention exhibits significantly superior properties in terms of efficiency compared to the organic light emitting device using a compound substituted with two cyano groups.

[0111] Comparing Experimental Examples 1 to 13 with Comparative Experimental Examples 7, 9, and 11 in Table 1, it was confirmed that the organic light-emitting device containing the compound of Chemical Formula 1 of the present invention exhibits significantly superior characteristics in terms of lifetime compared to the organic light-emitting device using a compound in which the cyano group is not substituted. [Explanation of symbols]

[0112] 1: Circuit board 2: Anode 3: Light-emitting layer 4: Cathode 5: Hole injection layer 6: Hole transport layer 7: Electron transport and injection layer

Claims

1. A compound represented by the following chemical formula 1: 【Chemical 1】 In the above Chemical Formula 1, X's are each independently N, CH, or CD, and two or more of X's are N; L is a single bond or a substituted or unsubstituted C ６－６０ is an arylene, Ar １ and Ar ２ are each independently a substituted or unsubstituted C ６－６０ is aryl, Ar ３ and Ar ４ are each independently unsubstituted or phenyl substituted with one or more deuterium atoms; Ar １ ~Ar ４ one of which is substituted with cyano; HAr is unsubstituted or deuterium, substituted or unsubstituted C １－６０ Alkyl, and substituted or unsubstituted C ６－６０ pyrimidinyl substituted by 1 to 3 substituents each independently selected from the group consisting of aryl; substituted or unsubstituted, two C ６－６０ aryl-substituted triazinyl; or substituted or unsubstituted, one C ６－６０ aryl-substituted quinazolinyl; D is deuterium, a and b are each independently an integer from 0 to 4; n and m are each independently 0 or 1; where n+m is 1, a+n is an integer from 0 to 4, b+m is an integer of 0 to 4.

2. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3: 【Chemistry 2】 【Chemistry 3】 In the chemical formulas 1-1 to 1-3, X, L, Ar １ , Ar ２ , Ar ３ , Ar ４ , D, a, b, n and m are as defined in claim 1; Y is N or CR', and two or more of the Y's are N; R' is hydrogen, deuterium, substituted or unsubstituted C １－６０ Alkyl, or substituted or unsubstituted C ６－６０ is aryl, R １ and R ２ are each independently a substituted or unsubstituted C ６－６０ is aryl, c is an integer of 0 to 4.

3. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-4 to 1-9: 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 In the chemical formulas 1-4 to 1-9, X, L, Ar １ , Ar ２ , A ３ , Ar ４ , D, HAr, a, and b are as defined in claim 1.

4. L is a single bond, phenylene, or biphenyldiyl; The compound of claim 1 , wherein the phenylene and biphenyldiyl are unsubstituted or substituted with one or more deuterium atoms.

5. Ar １ 2. The compound of claim 1, wherein is phenyl that is unsubstituted or substituted with one or more deuterium atoms.

6. Ar ２ is phenyl, biphenylyl, or naphthyl, and ２ The compound of claim 1 , wherein is unsubstituted or substituted with one or more deuterium atoms.

7. L is phenylene or biphenyldiyl, wherein said L is unsubstituted or substituted with one or more deuterium atoms; Ar ２ is phenyl substituted with cyano, or naphthyl substituted with cyano, wherein said Ar ２ 2. The compound of claim 1, wherein is deuterium substituted or unsubstituted.

8. L is a single bond; Ar ２ is phenyl or biphenylyl, wherein said Ar ２ is unsubstituted or substituted with one or more deuterium atoms; Ar ３ is phenyl substituted with cyano, wherein said Ar ３ 2. The compound of claim 1, wherein is deuterium substituted or unsubstituted.

9. 3. The compound of claim 2, wherein R' is hydrogen, deuterium, or methyl that is unsubstituted or substituted with one or more deuterium atoms.

10. R １ and R ２ are each independently phenyl, biphenylyl, or naphthyl; The R １ and R ２ 3. The compound of claim 2, wherein is unsubstituted or substituted with one or more deuterium atoms.

11. The compound of claim 1, wherein the compound represented by Chemical Formula 1 is any one selected from the group consisting of the following compounds: 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 。

12. 12. An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound according to claim 1.

13. The organic light-emitting device according to claim 12 , wherein the organic layer containing the compound is an electron transport layer, an electron injection layer, or an electron transport and injection layer.

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