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 one of X is N, and

[0017] Y is O or S, and

[0018] Ar1 and Ar2 are each independently C substituted with one or more deuterium atoms. 6-60 Arilgo,

[0019] L is a substituted or unsubstituted C 6-60 C comprising arylene, or any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S. 2-60 It is heteroarylene, and

[0020] R1 and R2 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 6-60 C comprising one or more heteroatoms selected from the group consisting of aryl, or substituted or unsubstituted N, O, and S. 2-60 It is heteroaryl, and

[0021] R3 is hydrogen, or deuterium, and

[0022] R4 and R5 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 6-60 C comprising one or more heteroatoms selected from the group consisting of aryl, or substituted or unsubstituted N, O, and S. 2-60 It is heteroaryl, and

[0023] a is an integer from 0 to 3, and

[0024] b is an integer from 0 to 6.

[0026] 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

[0028] The compound represented by the chemical formula 1 described above 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. Brief explanation of the drawing

[0030] 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 first hole transport layer (6), a second hole transport layer (7), an electron blocking layer (8), a light-emitting layer (3), a hole blocking layer (9), an electron injection and transport layer (10), and a cathode (4). Specific details for implementing the invention

[0031] The present invention will be described in more detail below to aid in understanding.

[0033] In this specification, and represents a bond connected to another substituent, and "D" represents deuterium.

[0035] 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."

[0037] 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.

[0038]

[0040] 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.

[0041]

[0043] 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.

[0044]

[0046] 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.

[0048] In this specification, boron groups specifically include trimethylboron groups, triethylboron groups, t-butyldimethylboron groups, triphenylboron groups, phenylboron groups, etc., but are not limited thereto.

[0050] In this specification, examples of halogen groups include fluoro, chloro, bromo, or iodo.

[0052] 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.

[0054] 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.

[0056] 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.

[0058] 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.

[0060] 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.

[0062] 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.

[0064] 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.

[0066] 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.

[0068] 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 backbone. However, it is not limited to this.

[0070] 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.

[0072] 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.

[0074] 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.

[0076] 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.

[0078] 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.

[0080] 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.

[0082] 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.

[0083]

[0085] 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.

[0087] 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.

[0089] (compound)

[0090] The present invention provides a compound represented by the above chemical formula 1.

[0092] Preferably, Formula 1 is represented by any one of Formulas 1-1 to 1-3:

[0093] [Chemical Formula 1-1]

[0094]

[0095] [Chemical Formula 1-2]

[0096]

[0097] [Chemical Formula 1-3]

[0098]

[0099] In the above chemical formulas 1-1 to 1-3,

[0100] X, Y, Ar1, Ar2, L, R1 to R5, a and b are as defined in Chemical Formula 1.

[0102] Preferably, X is all N.

[0104] Preferably, L is unsubstituted or phenylene substituted with one or more deuterium atoms.

[0105] Specifically, L is any one selected from the group consisting of the following and their deuteriumized structures:

[0106] .

[0108] Preferably, Ar1 and Ar2 are each independently phenyl, biphenyllyl, or terphenyllyl, and Ar1 and Ar2 are each independently substituted with one or more deuterium atoms.

[0109] For example, the above Ar1 and Ar2 are each independently phenyl, and the above Ar1 and Ar2 are each independently substituted with 1, 2, 3, 4, or 5 deuterium atoms.

[0110] More specifically, Ar1 and Ar2 are each independently the following substituents:

[0111] .

[0113] Preferably, R1 and R2 are each independently hydrogen, deuterium, or phenyl, wherein at least one of R1 and R2 is deuterium, and the phenyl is unsubstituted or substituted with one or more deuteriums.

[0114] More preferably, R1 is all deuterium.

[0115] More preferably, R2 is each independently hydrogen, deuterium, or unsubstituted or substituted with one or more deuterium phenyls, wherein two or more of R2s are deuterium.

[0117] Preferably, substituents is any one of the following:

[0118] .

[0120] Preferably, R4 and R5 are each independently hydrogen or deuterium.

[0122] When the above compound contains deuterium, the deuterium substitution rate of the compound may be 5% to 100%. Specifically, the deuterium substitution rate of the above compound may be 5% or more, 6% or more, 7% or more, 8% or more, 9% or more, 10% or more, 12% or more, 15% or more, 16% or more, 17% or more, 18% or more, 19% or more, or 20% or more, and may be 100% or less, 80% or less, 60% or less, 40% or less, or 20% or less.

[0124] For example, the above compound may contain one or more deuterium atoms. More specifically, it may contain two or more, three or more, four or more, five or more, six or more, seven or more, eight or more, nine or more, or ten or more deuterium atoms, and may contain 30 or fewer, 20 or fewer, 15 or fewer, 10 or fewer, nine or fewer, eight or fewer, or seven or fewer deuterium atoms.

[0126] Representative examples of compounds represented by the above chemical formula 1 are as follows:

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135] .

[0137] Meanwhile, the compound represented by the above chemical formula 1 can be prepared, for example, by a manufacturing method such as the following reaction scheme 1:

[0138] [Reaction Equation 1]

[0139]

[0140] In the above reaction scheme 1, X, Y, Ar1, Ar2, L, R1 to R5, a and b are as defined in formula 1, and Z1 and Z2 are each independently halogens, preferably Z1 and Z2 are each independently fluoro or chloro.

[0142] Each step of the above reaction scheme 1 is a Suzuki coupling reaction and an amine substitution reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactor for each reaction can be modified as known in the art. The above manufacturing method can be further specified in the manufacturing examples to be described later.

[0144] (Organic light-emitting diode)

[0145] 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.

[0147] 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.

[0149] 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.

[0151] 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.

[0153] 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.

[0155] FIG. 2 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a hole injection layer (5), a first hole transport layer (6), a second hole transport layer (7), an electron blocking layer (8), a light-emitting layer (3), a hole blocking layer (9), an electron injection and transport layer (10), and a cathode (4).

[0157] 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.

[0159] 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.

[0161] 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.

[0163] 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.

[0165] 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.

[0167] 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.

[0169] 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.

[0171] 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.

[0173] 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.

[0175] 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.

[0177] 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.

[0179] 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.

[0181] 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.

[0183] 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.

[0185] 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 that can effectively receive electrons from the cathode and transfer them to the light-emitting layer, and materials with high electron mobility are suitable. 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.

[0187] 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.

[0189] 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-hydroxyquinolinato)chlorogallium, bis(2-methyl-8-hydroxyquinolinato)(o-cresolato)gallium, Bis(2-methyl-8-hydroxyquinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-hydroxyquinolinato)(2-naphtolato)gallium, etc., are included but are not limited thereto.

[0191] In one embodiment, the light-emitting layer of the organic light-emitting device may include a compound represented by Formula 1 and a dopant. In this case, the light-emitting layer may include the compound represented by Formula 1 and the dopant 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.

[0193] The organic light-emitting device according to the present invention may be a bottom-emission device, a top-emission device, or a double-sided light-emitting device, and in particular may be a bottom-emission device for which relatively high light-emitting efficiency is required.

[0195] 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.

[0197] The preparation of the compound represented by Chemical Formula 1 above and the organic light-emitting device containing the same 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.

[0199] [Synthetic Example]

[0200] Synthesis Example 1: Synthesis of GH1

[0201]

[0202] <1-1> Manufacture of GH1-1

[0203] Under a nitrogen atmosphere, 2-chloro-4,6-bis(phenyl-2,3,5,6-d4)-1,3,5-triazine (30 g, 108.8 mmol) and (5'-chloro-2'-fluoro-[1,1'-biphenyl]-3-yl)boronic acid (27.2 g, 108.8 mmol) were added to 600 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (45.1 g, 326.4 mmol) dissolved in 45 ml of water was added and stirred thoroughly, after which tetracitriphenyl-phosphinopalladium (3.8 g, 3.3 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 2426 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 GH1-1 (34 g, 70%) was prepared by recrystallizing the concentrated compound with chloroform and ethyl acetate.

[0204] MS: [M+H] + = 447

[0206] <1-2> Manufacture of GH1-2

[0207] Under a nitrogen atmosphere, GH1-1 (20 g, 44.8 mmol) and dibenzo[b,d]thiophen-2-ylboronic acid (10.2 g, 44.8 mmol) were added to 400 ml of Diox and stirred and refluxed. Subsequently, tripotassium phosphate (28.6 g, 134.5 mmol) dissolved in 29 ml of water was added and stirred thoroughly, after which dibenzylideneacetone palladium (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol) were added. After reacting for 8 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 799 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. The concentrated compound was used to produce a yellow solid compound GH1-2 (18.1 g, 68%) through recrystallization with chloroform and ethyl acetate.

[0208] MS: [M+H] + = 594.8

[0210] <1-3> Manufacturing of GH1

[0211] Under a nitrogen atmosphere, GH1-2 (30 g, 50.5 mmol) and 9H-carbazole-1,2,3,4,5,6,8-d7 (8.8 g, 50.5 mmol) were added to 600 ml of dimethylformamide and stirred and refluxed. Subsequently, potassium triphosphate (32.2 g, 151.6 mmol) was added and stirred thoroughly. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. This was dissolved in 378 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. The concentrated compound was purified using chloroform and ethyl acetate via a silica column to produce the yellow solid compound GH1 (27.6 g, 73%).

[0212] MS: [M+H] += 749

[0214] Synthesis Example 2: Synthesis of GH2

[0215]

[0216] <2-1> Manufacture of GH2-1

[0217] Compound GH2-1 was prepared in the same manner as <1-2> of Synthesis Example 1, except that dibenzo[b,d]furan-3-ylboronic acid was used instead of dibenzo[b,d]thiophen-2-ylboronic acid.

[0218] MS: [M+H] + = 578

[0220] <2-2> Manufacturing of GH2

[0221] Compound GH2 was prepared in the same manner as <1-3> of Synthesis Example 1, except that compound GH2-1 was used instead of compound GH1-2.

[0222] MS: [M+H] + = 733

[0224] Synthesis Example 3: Synthesis of GH3

[0225]

[0226] <3-1> Manufacture of GH3-1

[0227] Compound GH3-1 was prepared in the same manner as <1-1> of Synthesis Example 1, except that (2'-chloro-6'-fluoro-[1,1'-biphenyl]-3-yl)boronic acid was used instead of (5'-chloro-2'-fluoro-[1,1'-biphenyl]-3-yl)boronic acid.

[0228] MS: [M+H] + = 447

[0230] <3-2> Manufacturing of GH3-2

[0231] Compound GH3-2 was prepared in the same manner as <1-2> of Synthesis Example 1, except that compound GH3-1 was used instead of compound GH1-1 and dibenzo[b,d]furan-3-ylboronic acid was used instead of dibenzo[b,d]thiophen-2-ylboronic acid.

[0232] MS: [M+H] + = 579

[0234] <3-3> Manufacturing of GH3

[0235] Compound GH3 was prepared in the same manner as <1-3> of Synthesis Example 1, except that compound GH3-2 was used instead of compound GH1-2.

[0236] MS: [M+H] + = 733

[0238] Synthesis Example 4: Synthesis of GH4

[0239]

[0240] <4-1> Manufacture of GH4-1

[0241] Compound GH4-1 was prepared in the same manner as <1-1> of Synthesis Example 1, except that (3-fluoro-[1,1'-biphenyl]-4-yl)boronic acid was used instead of (5'-chloro-2'-fluoro-[1,1'-biphenyl]-3-yl)boronic acid.

[0242] MS: [M+H] + = 447

[0244] <4-2> Manufacturing of GH4-2

[0245] Compound GH4-2 was prepared in the same manner as <1-2> of Synthesis Example 1, except that compound GH4-1 was used instead of compound GH1-1 and dibenzo[b,d]thiophen-3-ylboronic acid was used instead of dibenzo[b,d]thiophen-2-ylboronic acid.

[0246] MS: [M+H] + = 596

[0248] <4-3> Manufacturing of GH4

[0249] Compound GH4 was prepared in the same manner as <1-3> of Synthesis Example 1, except that compound GH4-2 was used instead of compound GH1-2, and 4-(phenyl-2,4,6-d3)-9H-carbazole-1,3,5,6,7,8-d6 was used instead of 9H-carbazole-1,2,3,4,5,6,8-d7.

[0250] MS: [M+H] + = 828

[0252] Synthesis Example 5: Synthesis of GH5

[0253]

[0254] <5-1> Manufacturing of GH5-1

[0255] Compound GH5-1 was prepared in the same manner as <1-1> of Synthesis Example 1, except that (3'-chloro-2'-fluoro-[1,1'-biphenyl]-3-yl)boronic acid was used instead of (5'-chloro-2'-fluoro-[1,1'-biphenyl]-3-yl)boronic acid.

[0256] MS: [M+H] + = 447

[0258] <5-2> Manufacturing of GH5-2

[0259] Compound GH5-2 was prepared in the same manner as <1-2> of Synthesis Example 1, except that compound GH5-1 was used instead of compound GH1-1 and dibenzo[b,d]furan-3-ylboronic acid was used instead of dibenzo[b,d]thiophen-2-ylboronic acid.

[0260] MS: [M+H] + = 579

[0262] <5-3> Manufacturing of GH5

[0263] Compound GH5 was prepared in the same manner as <1-3> of Synthesis Example 1, except that compound GH5-2 was used instead of compound GH1-2.

[0264] MS: [M+H] + = 733

[0266] [Example]

[0267] Example 1

[0268] A glass substrate coated with an indium tin oxide (ITO) thin film to a thickness of 1,000 Å was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. products were used as the detergent, and distilled water that had been filtered twice using a Millipore Co. filter was used. After cleaning the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol as solvents, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes and then transported to a vacuum deposition machine.

[0270] 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 first hole transport layer with a thickness of 50 Å was formed by vacuum deposition of the following compound HAT on the hole injection layer, and a second hole transport layer with a thickness of 500 Å was formed by vacuum deposition of the following compound HT-A on the first hole transport layer. An electron blocking layer was formed by thermal vacuum deposition of the following compound HT-B to a thickness of 450 Å on the hole transport layer.

[0272] On the electron blocking layer above, the previously prepared compound GH1 was mixed with the following compound GH-P in a 1:1 weight ratio, and then vacuum-deposited with the following compound GD in a 90:10 weight ratio to form a emitting layer with a thickness of 400 Å. On the emitting layer above, the following compound ET-A was vacuum-deposited to a thickness of 50 Å to form a hole blocking layer. On the hole blocking layer below, the following compound ET-B and the following compound LiQ were vacuum-deposited in a 1:1 weight ratio to form an electron injection and transport layer with a thickness of 350 Å.

[0274] An organic light-emitting diode was manufactured by depositing lithium fluoride (LiF) to a thickness of 10 Å on the electron injection and transport layer, and then depositing aluminum to a thickness of 1000 Å to form a cathode.

[0275]

[0277] In the above process, the deposition rate of the organic material was maintained between 0.4 Å / sec and 0.9 Å / sec, the deposition rate of lithium fluoride was maintained at 0.3 Å / sec, and the deposition rate of aluminum was maintained at 0.2 nm / sec. The vacuum level during deposition was 1 × 10⁻⁶ -7 torr to 5*10 -5 maintained torr.

[0279] Examples 2 to 5 and Comparative Examples 1 to 6

[0280] An organic light-emitting diode was prepared in the same manner as in Example 1, except that the compound listed in Table 1 below was used instead of compound GH1 in Example 1. In Table 1 below, the structures of compounds GH6 to GH11 are as follows.

[0281]

[0283] [Experimental Example]

[0284] Current was applied to the organic light-emitting diodes fabricated in Examples 1 to 5 and Comparative Examples 1 to 6 above to measure voltage, efficiency, emission color, and lifetime (T95), and the results are shown in Table 1 below. At this time, the voltage and efficiency were 10 mA / cm² 2 Measurements were taken by applying a current density of , and T95 has a current density of 10 mA / cm² 2 It refers to the time (hr) until the initial brightness drops to 95%.

[0286] division light-emitting layer compound Voltage (V) (@10mA / cm²) 2 ) Efficiency (cd / A) (@10mA / cm²) 2 ) luminous color T 95 (hr)(@10mA / cm 2 ) Example 1 Compound GH1 3.68 92.4 green 298 Example 2 Compound GH2 3.64 91.7 green 312 Example 3 Compound GH3 3.75 92.0 green 287 Example 4 Compound GH4 3.73 92.4 green 330 Example 5 Compound GH5 3.70 91.1 green 285 Comparative Example 1 Compound GH6 3.92 87.7 green 240 Comparative Example 2 Compound GH7 3.81 90.5 green 232 Comparative Example 3 Compound GH8 3.73 87.6 green 227 Comparative Example 4 Compound GH9 3.75 89.2 green 205 Comparative Example 5 Compound GH10 3.83 85.5 green 198 Comparative Example 6 Compound GH11 3.89 88.5 green 252 Explanation of the symbols

[0287] 1: Substrate 2: Anode 3: Emitting layer 4: Cathode 5: Hole injection layer 6: 1st Precision Transport Layer 7: 2nd Precision Transport Layer 8: Electromagnetic shielding layer 9: Poison blockade layer 10: Electron injection and transport layer

Claims

Claim 1 Compound represented by the following chemical formula 1: [Chemical Formula 1] In the above Chemical Formula 1, X is each independently N, CH, or CD, wherein at least one of X is N, Y is O or S, and Ar1 and Ar2 are each independently C substituted with one or more deuterium atoms. 6-60 It is an aryl, and L is a substituted or unsubstituted C 6-60 C comprising arylene, or any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S. 2-60 It is a heteroarylene, and R1 and R2 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 6-60 C comprising one or more heteroatoms selected from the group consisting of aryl, or substituted or unsubstituted N, O, and S. 2-60 It is a heteroaryl, R3 is hydrogen or deuterium, and R4 and R5 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 6-60 C comprising one or more heteroatoms selected from the group consisting of aryl, or substituted or unsubstituted N, O, and S. 2-60 It is heteroaryl, a is an integer from 0 to 3, and b is an integer from 0 to 6. Claim 2 In claim 1, the compound is represented by any one of chemical formulas 1-1 to 1-3: [Chemical formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] In the above chemical formulas 1-1 to 1-3, X, Y, Ar1, Ar2, L, R1 to R5, a and b are as defined in claim 1. Claim 3 In paragraph 1, a compound in which X is all N. Claim 4 In paragraph 1, L is a compound that is unsubstituted or substituted with one or more deuterium atoms, which is phenylene. Claim 5 A compound according to claim 1, wherein Ar1 and Ar2 are each independently phenyl, biphenyllyl, or terphenyllyl, and said Ar1 and Ar2 are each independently substituted with one or more deuterium atoms. Claim 6 A compound according to claim 1, wherein R1 and R2 are each independently hydrogen, deuterium, or phenyl, wherein at least one of R1 and R2 is deuterium, and said phenyl is unsubstituted or substituted with one or more deuterium. Claim 7 In paragraph 1, a compound in which R1 is all deuterium. Claim 8 A compound according to claim 1, wherein R2 is each independently hydrogen, deuterium, or unsubstituted or substituted with one or more deuteriums, wherein two or more of R2s are deuteriums. Claim 9 In paragraph 1, the substituent is a compound that is any one of the following: . Claim 10 In paragraph 1, R4 and R5 are each independently compounds of hydrogen or deuterium. Claim 11 In claim 1, the compound represented by the above chemical formula 1 is any one selected from the group consisting of the following: . Claim 12 An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound according to any one of claims 1 to 11. Claim 13 An organic light-emitting device according to claim 12, wherein the organic layer containing the above compound is a light-emitting layer.

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