Organic light-emitting devices

Abstract

The present invention provides an organic light emitting device.

Description

[Technical Field]

[0001] [CROSS-REFERENCE TO RELATED APPLICATIONS] This application claims the benefit of priority based on Korean Patent Application No. 10-2021-0056812, filed April 30, 2021, and Korean Patent Application No. 10-2022-0053540, filed April 29, 2022, and all contents disclosed in the documents of said Korean patent applications are incorporated herein by reference.

[0002] The present invention relates to an organic light-emitting device. [Background technology]

[0003] Generally, organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. Organic light emitting devices utilizing the organic light emitting phenomenon have a wide viewing angle, excellent contrast, and fast response time, and are excellent in brightness, driving voltage, and response speed characteristics, and therefore, much research is being conducted on these devices.

[0004] Organic light-emitting devices generally have a structure including an anode, an anode, and an organic material layer between the anode and the cathode. To enhance the efficiency and safety of organic light-emitting devices, the organic material layer is often a multi-layer structure composed of different materials, such as a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an electron injection layer. In such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected from the anode into the organic material layer. When the injected holes and electrons come into contact, excitons are formed. When the excitons return to their ground state, light is emitted.

[0005] There is a continuing demand for the development of new organic materials for use in the 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 an organic light-emitting device with improved driving voltage, efficiency and lifetime. [Means for solving the problem]

[0008] In order to solve the above problems, the present invention provides: a positive electrode; a negative electrode; and a light-emitting layer between the positive electrode and the negative electrode, The light-emitting layer includes a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2, to provide an organic light-emitting device: [Chemical formula 1] [ka] In the above Chemical Formula 1, Y is O or S; X1 to X3 each independently represent CH or N, provided that at least one of X1 to X3 is N; Ar1 and Ar2 each independently represent a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S; Ar3 is a substituted or unsubstituted aryl having 6 to 60 carbon atoms; n is an integer from 1 to 6, R1 each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms and containing at least one selected from the group consisting of N, O, and S; [Chemical formula 2] [ka] In the above Chemical Formula 2, n' and m' are each independently an integer from 1 to 7; R'1 and R'2 are each independently hydrogen; deuterium; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms and containing at least one selected from the group consisting of N, O, and S; Ar'1 and Ar'2 each independently represent a substituted or unsubstituted aryl having 6 to 12 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms and containing one or more heteroatoms selected from the group consisting of N, O, and S; provided that at least one of R'1 and R'2 is deuterium; and / or at least one of Ar'1 and Ar'2 is substituted with one or more deuterium atoms. [Effects of the Invention]

[0009] The organic light-emitting device described above is excellent in terms of driving voltage, efficiency, and life span. [Brief explanation of the drawings]

[0010] [Figure 1] 1 is a diagram showing an example of an organic light-emitting device composed of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. FIG. [Figure 2] 1 is a diagram showing an example of an organic light-emitting device comprising a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron transport layer 7, an electron injection layer 8, and a negative electrode 4. FIG. [Figure 3] FIG. 1 is a diagram showing an example of an organic light-emitting device comprising a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron inhibiting layer 9, a light-emitting layer 3, a hole inhibiting layer 10, an electron transport layer 7, an electron injection layer 8, and a negative electrode 4. DETAILED DESCRIPTION OF THE INVENTION

[0011] The present invention will now be described in more detail to aid in understanding the invention.

[0012] In the present invention, [ka] or [ka] denotes a bond that is connected to another substituent.

[0013] In the present invention, the term "substituted or unsubstituted" refers to a group selected from the group consisting of deuterium, halogen, nitrile, 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 heterocyclic groups containing one or more N, O, and S atoms, or a group selected from the 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 biphenyl group. That is, a biphenyl group may be an aryl group or may be interpreted as a substituent linked to two phenyl groups.

[0014] In the present invention, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group may have a structure as shown below, but is not limited thereto. [ka]

[0015] In this specification, the oxygen 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 compound having the following structural formula, but is not limited to these. [ka]

[0016] In this specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group may have a structure as shown below, but is not limited thereto. [ka]

[0017] In this specification, specific examples of silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl groups.

[0018] 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.

[0019] As used herein, examples of halogen groups include fluorine, chlorine, bromine or iodine.

[0020] 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, the number of carbon atoms in the alkyl group is 1 to 6. Specific examples of alkyl groups include, but are not limited to, 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, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

[0021] 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 yet 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, a stilbenyl group, and a styrenyl group, but are not limited to these.

[0022] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. 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.

[0023] In this specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited to these. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, or the like, but is not limited to these.

[0024] In this specification, the fluorenyl group may be substituted, and two 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.

[0025] In this specification, the heterocyclic group is a heterocyclic group containing one or more heteroelements selected from O, N, Si and S, and is not particularly limited in number of carbon atoms, but preferably has 2 to 60 carbon atoms. Examples of heterocyclic groups include, but are not limited to, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazine, acridyl, pyridacin, pyrazinyl, quinolinyl, quinazoline, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuranyl groups.

[0026] In this specification, the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is applicable to the aryl group. In this specification, the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is applicable to the alkyl group. In this specification, the heteroaryl among the heteroarylamine group is applicable to the heteroaryl. In this specification, the alkenyl group among the aralkenyl group is applicable to the alkenyl group. In this specification, the aryl group described above is applicable to the arylene, except that it is a divalent group. In this specification, the heterocyclic group described above is applicable to the heteroarylene, except that it is a divalent group. In this specification, the hydrocarbon ring is not a monovalent group, but is formed by the bonding of two substituents, and the aryl group or cycloalkyl group described above is applicable. In this specification, the heterocycle is not a monovalent group, but is formed by the bonding of two substituents, and the heterocyclic group described above is applicable.

[0027] The present invention will be described in detail below for each component.

[0028] Positive and negative electrodes The positive electrode and negative electrode used in the present invention refer to electrodes used in an organic light-emitting device.

[0029] The cathode material preferably has a high work function to facilitate hole injection into the organic layer. Specific examples of the cathode 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.

[0030] The negative electrode material is preferably a material with a small work function so as to facilitate electron injection into the organic layer. Specific examples of the negative electrode 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.

[0031] Light-emitting layer The light-emitting layer used in the present invention refers to a layer that can emit light in the visible light region by combining holes and electrons transferred from the positive electrode and the negative electrode. Generally, the light-emitting layer includes a host material and a dopant material, and in the present invention, the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 are used as hosts.

[0032] In the above Chemical Formula 1, at least one of X1 to X3 is N, and preferably two or more are N. In one embodiment, all of X1 to X3 are N.

[0033] Preferably, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms containing at least one selected from the group consisting of N, O, and S. Ar1 and Ar2 may each be substituted with one or more deuterium atoms.

[0034] Preferably, Ar1 and Ar2 are each independently phenyl; phenyl substituted with five deuteriums; biphenylyl; biphenylyl substituted with five deuteriums; terphenylyl; phenanthrenyl; carbazolyl; carbazolyl substituted with six deuteriums; dibenzofuranyl; or dibenzothiophenyl; triphenylenyl.

[0035] Preferably, Ar3 is a substituted or unsubstituted aryl having a carbon number of 6 to 25. Ar3 may be substituted with one or more deuterium atoms.

[0036] Preferably, Ar3 is phenyl, phenyl substituted with five deuterium atoms, biphenylyl, biphenylyl substituted with five to nine deuterium atoms, terphenylyl, terphenylyl substituted with five deuterium atoms, terphenylyl substituted with one phenyl atom, naphthyl, naphthylphenyl, phenanthrenyl, triphenylenyl, triphenylenyl substituted with one to nine deuterium atoms, triphenylenylphenyl, 9,9-dimethylfluorenyl, or 9,9'-spirobifluorenyl. In particular, when Ar3 is triphenylenyl or triphenylenyl substituted with one to nine deuterium atoms, the efficiency and lifetime of the organic light-emitting device can be more excellent.

[0037] Preferably, each R1 is independently hydrogen or deuterium.

[0038] In one embodiment, Y is O or S, two or more of X1 to X3 are N, each R1 is independently hydrogen or deuterium, Ar1 and Ar2 are independently phenyl; phenyl substituted with five deuterium atoms; biphenylyl; biphenylyl substituted with five deuterium atoms; terphenylyl; phenanthrenyl; carbazolyl; carbazolyl substituted with six deuterium atoms; dibenzofuranyl; or dibenzothiophenyl; triphenylenyl, and Ar3 is an aryl having 6 to 25 carbon atoms, substituted or unsubstituted with deuterium atoms.

[0039] In one embodiment, Y is O or S, two or more of X1 to X3 are N, each R1 is independently hydrogen or deuterium, Ar1 and Ar2 are independently an aryl having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, or a heteroaryl having 2 to 20 carbon atoms which is substituted or unsubstituted with deuterium and which contains one or more selected from the group consisting of N, O, and S, and Ar3 is phenyl; phenyl substituted with five deuterium atoms; biphenylyl; biphenylyl substituted with 5 to 9 deuterium atoms; terphenylyl; terphenylyl substituted with five deuterium atoms; terphenylyl substituted with one phenyl atom; naphthyl; naphthylphenyl; phenanthrenyl; triphenylenyl; triphenylenyl substituted with 1 to 9 deuterium atoms; triphenylenylphenyl; 9,9-dimethylfluorenyl; or 9,9'-spirobifluorenyl.

[0040] In one embodiment, Y is O or S, two or more of X1 to X3 are N, each R1 is independently hydrogen or deuterium, Ar1 and Ar2 are independently phenyl; phenyl substituted with five deuteriums; biphenylyl; biphenylyl substituted with five deuteriums; terphenylyl; phenanthrenyl; carbazolyl; carbazolyl substituted with six deuteriums; dibenzofuranyl; or dibenzothiophenyl; triphenylenyl, and Ar 3 is phenyl; phenyl substituted with five deuterium atoms; biphenylyl; biphenylyl substituted with five to nine deuterium atoms; terphenylyl; terphenylyl substituted with five deuterium atoms; terphenylyl substituted with one phenyl atom; naphthyl; naphthylphenyl; phenanthrenyl; triphenylenyl; triphenylenyl substituted with one to nine deuterium atoms; triphenylenylphenyl; 9,9-dimethylfluorenyl; or 9,9'-spirobifluorenyl.

[0041] In one embodiment, Y is O or S, X1 to X3 are all N, R1 is each independently hydrogen or deuterium, Ar1 and Ar2 are each independently phenyl; phenyl substituted with five deuteriums; biphenylyl; biphenylyl substituted with five deuteriums; terphenylyl; phenanthrenyl; carbazolyl; carbazolyl substituted with six deuteriums; dibenzofuranyl; or dibenzothiophenyl; triphenylenyl, and Ar3 is triphenylenyl; or triphenylenyl substituted with one to nine deuteriums.

[0042] Representative examples of the compound represented by Formula 1 are as follows: [ka] [ka] [ka] [ka]

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[0043] The compound represented by Chemical Formula 1 may be prepared by a method such as the following Reaction Scheme 1. [Reaction Scheme 1] [ka]

[0044] In the above reaction scheme 1, the remainder except for X' are as defined above, and X' are each independently a halogen, more preferably each independently bromo or chloro.

[0045] The above Reaction Scheme 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the Suzuki coupling reaction can be changed according to those known in the art.

[0046] The method for preparing the compound represented by Chemical Formula 1 will be more specifically described in the Preparation Examples below.

[0047] The compound represented by the chemical formula 2 is characterized by having one or more deuterium atoms.

[0048] That is, in Chemical Formula 2, at least one of R'1 and R'2 is deuterium; at least one of R'1 and R'2 is deuterium and at least one substituent of Ar'1 and Ar'2 contains one or more deuterium; or when neither R'1 nor R'2 is deuterium, at least one substituent of Ar'1 and Ar'2 may contain one or more deuterium.

[0049] The compound represented by Chemical Formula 2 is represented by the following Chemical Formula 2-1. [Chemical formula 2-1] [ka]

[0050] In the formula 2-1, n', m', R'1, R'2, Ar'1 and Ar'2 are as defined in the formula 2.

[0051] Preferably, R'1 and R'2 are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl having 6 to 12 carbon atoms, wherein the aryl may be substituted with one or more deuterium atoms.

[0052] Preferably, R'1 and R'2 are each independently hydrogen; deuterium; phenyl; or phenyl substituted with 1 to 5 deuterium atoms.

[0053] Preferably, Ar'1 and Ar'2 are each independently phenyl which is unsubstituted or substituted with 1 to 5 deuteriums; biphenyl which is unsubstituted or substituted with 1 to 9 deuteriums; naphthyl which is unsubstituted or substituted with 1 to 7 deuteriums; dimethylfluorenyl which is unsubstituted or substituted with 1 to 13 deuteriums; dibenzofuranyl which is unsubstituted or substituted with 1 to 7 deuteriums; or dibenzothiophenyl which is unsubstituted or substituted with 1 to 7 deuteriums.

[0054] In one embodiment, Chemical Formula 2 is represented by Chemical Formula 2-1, wherein R'1 and R'2 are each independently hydrogen; deuterium; phenyl; or phenyl substituted with 1 to 5 deuteriums, and Ar'1 and Ar'2 are each independently unsubstituted or substituted with 1 to 5 deuteriums; biphenyl unsubstituted or substituted with 1 to 9 deuteriums; naphthyl unsubstituted or substituted with 1 to 7 deuteriums; dimethylfluorenyl unsubstituted or substituted with 1 to 13 deuteriums; dibenzofuranyl unsubstituted or substituted with 1 to 7 deuteriums; or dibenzothiophenyl unsubstituted or substituted with 1 to 7 deuteriums.

[0055] Preferably, the deuterium substitution rate of Chemical Formula 2 is 60 to 100%. The "deuterium substitution rate" refers to the number of deuterium atoms contained in Chemical Formula 2 relative to the total number of hydrogen atoms that can be present in Chemical Formula 2. Preferably, the deuterium substitution rate of Chemical Formula 3 is 65% or more, 70% or more, 75% or more, 80% or more, 85% or more, or 90% or more, and 99% or less, 98% or less, 97% or less, 96% or less, 95% or less, 94% or less, 93% or less, or 92% or less.

[0056] Representative examples of the compound represented by Formula 2 are as follows: [ka] [ka] [ka] [ka] [ka] In the above, the methyl groups contained in each chemical formula are each independently CH3, CH2D, CHD2, or CD3. For example, the chemical formula [ka] wherein the two methyl groups contained in the dimethylfluorenyl may each independently be CH3, CH2D, CHD2, or CD3.

[0057] The compound represented by Chemical Formula 2 may be prepared, for example, by a preparation method as shown in Reaction Scheme 2 below. [Reaction Scheme 2] [ka]

[0058] In the above reaction scheme 2, the remainder except for X'' are as defined above, and X'' is a halogen, more preferably bromo or chloro.

[0059] The above Reaction Scheme 2 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the Suzuki coupling reaction can be changed according to those known in the art.

[0060] The method for preparing the compound represented by Chemical Formula 2 will be more specifically described in the Preparation Examples below.

[0061] In the light-emitting layer, the weight ratio of the compound represented by Chemical Formula 1 to the compound represented by Chemical Formula 2 is 1:99 to 99:1, 5:95 to 95:5, or 10:90 to 90:10.

[0062] Meanwhile, the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 may be included in the light-emitting layer as a simple mixture, or Organic Alloy The light-emitting layer may contain the organic compound (organic alloy). Organic Alloy is a result of pre-treatment of two or more single organic compounds, which may result in chemical interaction between the single organic compounds, and may be, but is not limited to, a thermal treatment process such as heating and / or sublimation followed by cooling.

[0063] The aforementioned Organic Alloy As mentioned above, because there is a chemical interaction between two or more single organic compounds, the mixture has different properties from each single organic compound and a simple mixture in which there is no chemical interaction between the single organic compounds. Here, a simple mixture refers to a mixture in which the single organic compounds are simply physically mixed without any pretreatment. That is, a simple mixture of a first organic compound and a second organic compound exhibits the properties of the first organic compound, the second organic compound, or a combination thereof, while a simple mixture of a first organic compound and a second organic compound exhibits the properties of the first organic compound, the second organic compound, or a combination thereof. Organic Alloy can exhibit properties that differ from the first organic compound, the second organic compound, or a simple mixture thereof.

[0064] For example, Organic Alloy The emission wavelength of the first organic compound may be different from the emission wavelength of the second organic compound, and a simple mixture thereof.

[0065] In addition, the above Organic Alloy The color of the first organic compound may be different from the color of the second organic compound, and the color of the simple mixture thereof.

[0066] In addition, the above Organic AlloyThe glass transition temperature (Tg) of the first organic compound, the second organic compound, and a simple mixture thereof may be different from the glass transition temperature (Tg) of the first organic compound, the second organic compound, and a simple mixture thereof. Organic Alloy The crystallization temperature (Tc) of the first organic compound may be different from the crystallization temperatures of the first organic compound, the second organic compound, and the simple mixture thereof. Organic Alloy The melting temperature (Tm) of the first organic compound may be different from the melting temperatures of the first organic compound, the second organic compound, and simple mixtures thereof.

[0067] The aforementioned Organic Alloy can be pretreated in various ways, for example, by heat treating the first organic compound and the second organic compound to liquefy or vaporize them, and then cooling the heat-treated compounds to solidify them. Organic Alloy may be subjected to an additional step of physical pulverization using a mixer or the like.

[0068] The aforementioned Organic Alloy is the result of the pretreatment as described above, and can be supplied using one source during thin film formation. This simplifies the process because it eliminates the need for process control steps that are required when supplying two or more materials from separate sources.

[0069] In addition, the above Organic Alloy is a result of the pretreatment described above, which ensures uniformity and consistency of the deposited material compared to when two or more single organic compounds are supplied from separate sources or when a simple mixture of two or more single organic compounds is supplied from a single source. Therefore, when forming a plurality of thin films in successive processes, thin films having substantially the same ratio of components can be continuously produced, thereby improving the reproducibility and reliability of the thin films.

[0070] The dopant material is not particularly limited as long as it is a material used in organic light-emitting devices. Examples include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include fused aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periflanthene, each of which has an arylamino group. Styrylamine compounds include substituted or unsubstituted arylamines substituted with at least one arylvinyl group, and these substituted or unsubstituted groups are 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. Furthermore, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0071] hole transport layer The organic light-emitting device according to the present invention may include a hole transport layer between the light-emitting layer and the positive electrode.

[0072] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. As the hole transport material, a material that can receive holes from the positive electrode or the hole injection layer and move them to the light emitting layer and has high mobility for holes is preferred.

[0073] Specific examples of the hole transport material include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers having conjugated and non-conjugated portions.

[0074] hole injection layer The organic light-emitting device according to the present invention may further include a hole-injection layer between the anode and the hole-transport layer, if necessary.

[0075] The hole injection layer is a layer that injects holes from the electrode, and the hole injection material preferably has the ability to transport holes, has an excellent hole injection effect from the cathode, has an excellent hole injection effect on the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material, and has excellent thin-film forming ability. Furthermore, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the cathode material and the HOMO of the surrounding organic layer.

[0076] Specific examples of hole injection materials include, but are not limited to, metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers.

[0077] electron suppression layer The organic light-emitting device according to the present invention may include an electron-blocking layer between the hole-transporting layer and the light-emitting layer, if necessary.

[0078] The electron inhibiting layer prevents electrons injected from the anode from passing to the hole transporting layer without being recombined in the light emitting layer, and is also called an electron blocking layer. The electron inhibiting layer is preferably made of a material having a smaller electron affinity than the electron transporting layer.

[0079] electron transport layer The organic light-emitting device according to the present invention may include an electron transport layer between the light-emitting layer and the negative electrode.

[0080] The electron transport layer receives electrons from the anode or the electron injection layer formed on the anode, transports the electrons to the light-emitting layer, and inhibits the transfer of holes from the light-emitting layer. As the electron transport material, a material that can efficiently receive electrons injected from the anode and transfer them to the light-emitting layer and has high electron mobility is preferred.

[0081] Specific examples of the electron transport material include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material, as used in the prior art. In particular, suitable cathode materials include those with low work functions, typically followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0082] electron injection layer The organic light-emitting device according to the present invention may further include an electron injection layer between the electron transport layer and the negative electrode, if necessary.

[0083] The electron injection layer is a layer that injects electrons from the electrode, and it is preferable to use a compound that has the ability to transport electrons, has an excellent electron injection effect from the negative electrode, has an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from moving to the hole injection layer, and has excellent thin-film formation ability.

[0084] Specific examples of materials used in the electron injection layer include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0085] 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-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtholato)gallium.

[0086] hole blocking layer The organic light-emitting device according to the present invention may include a hole-blocking layer between the electron-transporting layer and the light-emitting layer, if necessary.

[0087] The hole blocking layer prevents holes injected from the anode from being recombined in the light emitting layer and passing to the electron transport layer, and is preferably made of a material having a large ionization energy.

[0088] Organic light-emitting devices The structure of an organic light-emitting device according to the present invention is illustrated in Fig. 1. Fig. 1 is a diagram showing an example of an organic light-emitting device comprising a substrate 1, a positive electrode 2, an emitting layer 3, and a negative electrode 4. Fig. 2 is a diagram showing an example of an organic light-emitting device comprising a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an emitting layer 3, an electron transport layer 7, an electron injection layer 8, and a negative electrode 4. Fig. 3 is a diagram showing an example of an organic light-emitting device comprising a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron inhibiting layer 9, an emitting layer 3, a hole inhibiting layer 10, an electron transport layer 7, an electron injection layer 8, and a negative electrode 4.

[0089] The organic light emitting device according to the present invention can be fabricated by sequentially stacking the above-described components. In this case, a metal, a conductive metal oxide, or an alloy thereof is deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a cathode, and the above-described layers are then formed thereon, followed by the deposition of a material to be used as a cathode.

[0090] In addition to this method, organic light-emitting devices can be fabricated by sequentially depositing cathode and cathode materials on a substrate in the reverse order of the above-described structure (WO 2003 / 012890). Furthermore, the light-emitting layer can be formed by vacuum deposition of the host and dopant, as well as by solution coating. Here, solution coating includes, but is not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, and roll coating.

[0091] 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.

[0092] The preparation of the organic light emitting device according to the present invention will be described in detail in the following examples. However, the following examples are merely for the purpose of illustrating the present invention, and the scope of the present invention is not limited thereto.

[0093] [Synthesis Example 1: Preparation of Compound of Formula 1] Synthesis Example 1-1: Synthesis of intermediate A-4 [ka]

[0094] 1) Preparation of Compound A-1 1-Bromo-3-fluoro-2-iodobenzene (75 g, 249.3 mmol) and (5-chloro-2-methoxyphenyl)boronic acid (51.1 g, 249.3 mmol) were dissolved in 550 mL of tetrahydrofuran. To this solution, 2M sodium carbonate (NaCO) solution (350 mL) and tetrakis(triphenylphosphine)palladium(0) (2.88 g, 2.49 mmol) were added and refluxed for 11 hours. After the reaction was completed, the mixture was cooled to room temperature, and the aqueous layer was separated and removed. The mixture was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The mixture was recrystallized using chloroform and ethanol to obtain Compound A-1 (63.2 g, 80% yield; MS: [M+H] + =314).

[0095] 2) Preparation of Compound A-2 Compound A-1 (63.2 g, 200.3 mmol) was dissolved in 750 mL of dichloromethane and cooled to 0°C. Boron tribromide (20.0 mL, 210.3 mmol) was slowly added dropwise and stirred for 12 hours. After the reaction was completed, the mixture was washed with water three times, dried over magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure and purified by column chromatography to give compound A-2 (57.9 g, yield 96%; MS: [M+H] + =300).

[0096] 3) Preparation of Compound A-3 Compound A-2 (57.9 g, 192.0 mmol) and calcium carbonate (79.6 g, 576.0 mol) were dissolved in 350 mL of N-methyl-2-pyrrolidone and stirred for 2 hours. The mixture was cooled to room temperature, and the mixture was then inverted and precipitated in water and filtered. The mixture was completely dissolved in dichloromenthane, washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized using ethanol, and dried to obtain compound A-3 (42.1 g, yield 78%; MS: [M+H]). + =280).

[0097] 4) Preparation of Compound A-4 Compound A-3 (42.1 g, 149.5 mmol) was dissolved in tetrahydrofuran (330 mL). The temperature was lowered to -78 °C, and 2.5 M tertiary butyl lithium (t-BuLi) (60.4 mL, 151.0 mmol) was slowly added. After stirring at the same temperature for 1 hour, triisopropyl borate (51.8 mL, 224.3 mmol) was added, and the mixture was stirred at room temperature for 3 hours while gradually increasing the temperature. 2 N aqueous hydrochloric acid (300 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed successively with water and ethyl ether, and then dried under vacuum to obtain intermediate A-4 (34.3 g, yield 93%; MS: [M+H] + =247) was manufactured.

[0098] Synthesis Example 1-2: Synthesis of Intermediate B-5 [ka]

[0099] 1) Preparation of Compound B-1 1-Bromo-3-chloro-2-methoxybenzene (100.0 g, 451.5 mmol) was dissolved in tetrahydrofuran (1000 mL) and cooled to -78 °C. 2.5 M tertiary butyl lithium (t-BuLi) (182.4 mL, 456.0 mmol) was slowly added dropwise. After stirring at the same temperature for 1 hour, triisopropyl borate (B(OiPr)3) (156.3 mL, 677.3 mmol) was added and the mixture was stirred at room temperature for 3 hours while gradually increasing the temperature. 2 N aqueous hydrochloric acid (150 mL) was added to the reaction mixture and stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed sequentially with water and ethyl ether, and then vacuum dried. After drying, the precipitate was recrystallized from chloroform and ethyl acetate and dried to obtain compound B-1 (84.2 g, yield 90%; MS: [M+H] + =230) was produced.

[0100] 2) Preparation of Compound B-2 Compound B-2 (74.6 g, 52% yield; MS: [M+H]) was prepared in the same manner as in Synthesis Example 3-1, except that compound B-1 (84.2 g, 451.7 mmol) was used instead of (5-chloro-2-methoxyphenyl)boronic acid. + =314) was manufactured.

[0101] 3) Preparation of Compound B-3 Compound B-3 (60.3 g, 85% yield; MS: [M+H]) was obtained in the same manner as compound A-2, except that compound B-2 (74.6 g, 236.4 mmol) was used instead of compound A-1. + =300) was produced.

[0102] 4) Preparation of Compound B-4 Compound B-4 (48.1 g, 85% yield; MS: [M+H]) was obtained in the same manner as compound A-3, except that compound B-3 (60.3 g, 199.9 mmol) was used instead of compound A-2. + =280) was produced.

[0103] 5) Preparation of Compound B-5 Compound B-5 (40.1 g, 95% yield; MS: [M+H]) was obtained in the same manner as compound A-4, except that compound B-3 (48.1 g, 170.9 mmol) was used instead of compound A-3. + =247) was manufactured.

[0104] Synthesis Example 1-3: Synthesis of intermediate C-4 compound [ka]

[0105] 1) Preparation of Compound C-1 Compound C-1 (60.1 g, 76% yield; MS: [M+H]) was prepared in the same manner as in Synthesis Example 1 to prepare Compound A-1, except that (4-chloro-2-methoxyphenyl)boronic acid (51.1 g, 249.3 mmol) was used instead of (5-chloro-2-methoxyphenyl)boronic acid.+ =314) was manufactured.

[0106] 2) Preparation of Compound C-2 Compound C-2 (54.0 g, 94% yield; MS: [M+H]) was obtained in the same manner as compound A-2, except that compound C-1 (60.1 g, 190.4 mmol) was used instead of compound A-1. + =300) was produced.

[0107] 3) Preparation of Compound C-3 Compound C-4 (42.2 g, 83% yield; MS: [M+H]) was obtained in the same manner as compound A-3, except that compound C-2 (54.0 g, 179.1 mmol) was used instead of compound A-2. + =280) was produced.

[0108] 4) Preparation of Compound C-4 Compound C-4 (34.1 g, 92% yield; MS: [M+H]) was obtained in the same manner as compound A-4, except that compound C-3 (42.2 g, 170.9 mmol) was used instead of compound A-3. + =247) was manufactured.

[0109] Synthesis Example 1.4: Synthesis of intermediate D-4 [ka]

[0110] 1) Preparation of Compound D-1 Compound D-1 (63.5 g, 81% yield; MS: [M+H]) was prepared in the same manner as in Synthesis Example 1 to prepare Compound A-1, except that (2-chloro-6-methoxyphenyl)boronic acid (51.1 g, 249.3 mmol) was used instead of (5-chloro-2-methoxyphenyl)boronic acid. + =314) was manufactured.

[0111] 2) Preparation of Compound D-2 Compound D-2 (55.1 g, 91% yield; MS: [M+H]) was obtained in the same manner as compound A-2, except that compound D-1 (63.5 g, 201.2 mmol) was used instead of compound A-1. + =300) was produced.

[0112] 3) Preparation of Compound C-3 Compound C-3 (42.0 g, 82% yield; MS: [M+H]) was obtained in the same manner as compound A-3, except that compound C-2 (55.1 g, 182.7 mmol) was used instead of compound A-2. + =280) was produced.

[0113] 4) Preparation of Compound C-4 Compound C-4 (35.7 g, 85% yield; MS: [M+H]) was obtained in the same manner as compound A-4, except that compound C-3 (42.0 g, 149.2 mmol) was used instead of compound A-3. + =247) was manufactured.

[0114] Synthesis Example 1-5: Synthesis of intermediate E-4 [ka]

[0115] Compound E-4 was prepared in the same manner as in Synthesis Example 1-1, except that 1-bromo-3-fluoro-2-iodobenzene was replaced with 4-bromo-2-fluoro-1-iodobenzene. (MS: [M+H] + =247)

[0116] Synthesis Example 1-6: Synthesis of intermediate F-4 [ka]

[0117] Compound F-4 was prepared in the same manner as in Synthesis Example 1-1, except that 1-bromo-3-fluoro-2-iodobenzene was replaced with 4-bromo-1-fluoro-2-iodobenzene. (MS: [M+H] + =247)

[0118] Synthesis Example 1-7: Synthesis of intermediate G-4 [ka]

[0119] Compound G-4 was prepared in the same manner as in Synthesis Example 1-1, except that 1-bromo-3-fluoro-2-iodobenzene was used instead of 1-bromo-2-fluoro-3-iodobenzene and (5-chloro-2-methoxyphenyl)boronic acid was used instead of (4-chloro-2-methoxyphenyl)boronic acid. (MS: [M+H] + =247)

[0120] Synthesis Example 1-8: Synthesis of intermediate H-4 compound [ka]

[0121] Compound H-4 was prepared in the same manner as in Synthesis Example 1-1, except that 1-bromo-3-fluoro-2-iodobenzene was replaced with 4-bromo-2-fluoro-1-iodobenzene and (5-chloro-2-methoxyphenyl)boronic acid was replaced with (4-chloro-2-methoxyphenyl)boronic acid. (MS: [M+H] + =247)

[0122] Synthesis Example 1-9: Synthesis of intermediate I-5 [ka]

[0123] Compound I-5 was prepared in the same manner as in Compound 1-1, except that in Synthesis Example 1-1, 1-bromo-3-fluoro-2-iodobenzene was replaced with 1-bromo-2-fluoro-3-iodobenzene and (5-chloro-2-methoxyphenyl)boronic acid was replaced with Compound I-1 prepared in the same manner as in Compound 3-2. (MS: [M+H] + =247)

[0124] Synthesis Example 1-10: Synthesis of intermediate J-4 [ka]

[0125] Compound J-4 was prepared in the same manner as in Synthesis Example 1-1, except that 1-bromo-3-fluoro-2-iodobenzene was used instead of 1-bromo-2-fluoro-3-iodobenzene. (MS: [M+H] + =247)

[0126] Synthesis Example 1-11: Synthesis of Compound 1-1 Step 1) Synthesis of intermediate 1-1-1 [ka]

[0127] Under a nitrogen atmosphere, A-4 (20 g, 81.2 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (21.8 g, 81.2 mmol) were added to 500 mL of tetrahydrofuran and stirred under reflux. Potassium carbonate (33.6 g, 243.5 mmol) dissolved in 34 mL of water was then added and thoroughly stirred. Then, bis(tri-tert-butylphosphine)palladium (1.2 g, 2.4 mmol) was added. After 7 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1781 mL of tetrahydrofuran and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with tetrahydrofuran and ethyl acetate to obtain white solid compound 1-1-1 (32.4 g, 92% yield; MS: [M+H] + =434)) was manufactured.

[0128] Step 2) Synthesis of Compound 1-1 [ka]

[0129] Under a nitrogen atmosphere, 1-1-1 (10 g, 22.8 mmol) and triphenylen-2-ylboronic acid (6.2 g, 22.8 mmol) were added to 200 mL of dioxane and stirred under reflux. Then, tripotassium phosphate (14.5 g, 68.3 mmol) dissolved in 15 mL of water was added and thoroughly stirred. Then, dibenzylideneacetone palladium (0.4 g, 0.7 mmol) and tricyclohexylphosphine (0.4 g, 1.4 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 431 mL of dichlorobenzene and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from dichlorobenzene and ethyl acetate to obtain solid compound 1-1 (10.5 g, 73%, MS: [M+H] + =626)) was manufactured.

[0130] Synthesis Example 1-12: Synthesis of Compound 1-2 [ka]

[0131] Compound 1-2 was synthesized in the same manner as in Synthesis Example 1-11, except that 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (MS: [M+H] + =631).

[0132] Synthesis Example 1-13: Synthesis of Compound 1-3 [ka]

[0133] Compound 1-3 was synthesized in the same manner as in Synthesis Example 1-11, except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine and [1,1':4',1''-terphenyl]-4-ylboronic acid were used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and triphenylen-2-ylboronic acid (MS: [M+H] + =704).

[0134] Synthesis Example 1-14: Synthesis of Compound 1-4 [ka]

[0135] Compound 1-4 was synthesized in the same manner as in Synthesis Example 1-11, except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine and [1,1'-biphenyl]-4-ylboronic acid were used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and triphenylen-2-ylboronic acid (MS: [M+H] + =642).

[0136] Synthesis Example 1-15: Synthesis of Compound 1-5 [ka]

[0137] Step 1) Synthesis of intermediate 1-1-5 Under a nitrogen atmosphere, B-4 (22.1 g, 78.5 mmol) and [1,1':3',1''-terphenyl]-5'-ylboronic acid (21.5 g, 78.5 mmol) were added to 553 mL of tetrahydrofuran and stirred under reflux. Potassium carbonate (32.5 g, 235.5 mmol) dissolved in 33 mL of water was then added and thoroughly stirred, followed by the addition of bis(tri-tertiarybutylphosphine)palladium (1.2 g, 2.4 mmol). After 7 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1688 mL of tetrahydrofuran and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with tetrahydrofuran and ethyl acetate to obtain white solid compound 1-1-5 (27 g, 80%, MS: [M+H] + =431) was manufactured.

[0138] Step 2) Synthesis of intermediate 1-1-6 Under a nitrogen atmosphere, 1-1-5 (27 g, 62.8 mmol) and bis(pinacolato)diboron (19.1 g, 75.3 mmol) were added to 540 mL of dioxane and stirred under reflux. Potassium acetate (18.1 g, 188.3 mmol) was then added and thoroughly stirred. Palladium dibenzylideneacetone palladium (1.1 g, 1.9 mmol) and tricyclohexylphosphine (1.1 g, 3.8 mmol) were then added. After 6 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 984 mL of chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. The filtrate was then distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to give white solid compound 1-1-6 (25.3 g, 77%, MS: [M+H] + =523.5) was produced.

[0139] Step 3) Synthesis of Compounds 1-5 Under a nitrogen atmosphere, 1-1-6 (25 g, 47.9 mmol) and 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (13.3 g, 47.9 mmol) were added to 625 mL of tetrahydrofuran and stirred under reflux. Potassium carbonate (19.8 g, 143.6 mmol) dissolved in 20 mL of water was then added and thoroughly stirred. Bis(tri-tertiarybutylphosphine)palladium (0.7 g, 1.4 mmol) was then added. After 7 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1526 mL of tetrahydrofuran and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with tetrahydrofuran and ethyl acetate to obtain a white solid, compound 1-5 (20.4 g, 67%, MS: [M+H] + =638.8) was produced.

[0140] Synthesis Example 1-16: Synthesis of Compound 1-6 [ka]

[0141] Compound 1-6 was synthesized in the same manner as in Synthesis Example 1-11, except that [1,1'-biphenyl]-3-ylboronic acid was used instead of triphenylen-2-ylboronic acid (MS: [M+H] + =552).

[0142] Synthesis Example 1-17: Synthesis of Compound 1-7 [ka]

[0143] Compound 1-7 was synthesized in the same manner as in Synthesis Example 1-15, except that (triphenylen-2-yl-1,3,6,7,8,9,10,11-d8)boronic acid and 2-chloro-4,6-diphenyl-1,3,5-triazine were used instead of [1,1':3',1''-terphenyl]-5'-ylboronic acid and 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (MS: [M+H] + =634).

[0144] Synthesis Example 1-18: Synthesis of Compound 1-8 [ka]

[0145] Compound 1-6 was synthesized in the same manner as in Synthesis Example 1-11, except that ([1,1':4',1''-diphenyl]-4-yl-2'',3'',4'',5'',6''-d5)boronic acid was used instead of triphenylen-2-ylboronic acid (MS: [M+H] + =633).

[0146] Synthesis Example 1-19: Synthesis of Compound 1-9 [ka]

[0147] Compound 1-9 was synthesized in the same manner as in Synthesis Example 1-11, except that [1,1':4',1''-terphenyl]-3-ylboronic acid was used instead of triphenylen-2-ylboronic acid (MS: [M+H] + =628).

[0148] Synthesis Example 1-20: Synthesis of Compound 1-10 [ka]

[0149] Compound 1-10 was synthesized in the same manner as in Synthesis Example 1-15, except that phenylboronic acid and 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole-1,3,4,5,6,8-d6 were used instead of [1,1':3',1''-terphenyl]-5'-ylboronic acid and 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (MS: [M+H] + =571).

[0150] Synthesis Example 1-21: Synthesis of Compound 1-11 [ka]

[0151] Compound 1-11 was synthesized in the same manner as in Synthesis Example 1-11, except that phenanthren-2-ylboronic acid was used instead of triphenylen-2-ylboronic acid (MS: [M+H] + =576).

[0152] Synthesis Example 1-22: Synthesis of Compound 1-12 [ka]

[0153] Compound 1-12 was synthesized in the same manner as in Synthesis Example 1-11, except that 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine and [1,1'-biphenyl]-4-ylboronic acid were used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and triphenylen-2-ylboronic acid (MS: [M+H] + =642).

[0154] Synthesis Example 1-23: Synthesis of Compound 1-13 [ka]

[0155] Compound 1-13 was synthesized in the same manner as in Synthesis Example 1-15, except that ([1,1'-biphenyl]-3-yl-2',3',4,4',5,5',6,6'-d8)boronic acid and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine were used instead of [1,1':3',1''-terphenyl]-5'-ylboronic acid and 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (MS: [M+H] + =636).

[0156] Synthesis Example 1-24: Synthesis of Compound 1-14 [ka]

[0157] Compound 1-12 was synthesized in the same manner as in Synthesis Example 1-11, except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine and (phenyl-d5)boronic acid were used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and triphenylen-2-ylboronic acid (MS: [M+H]+ =557).

[0158] Synthesis Example 1-25: Synthesis of Compound 1-15 [ka]

[0159] Compound 1-15 was synthesized in the same manner as in Synthesis Example 1-11, except that [1,1':3',1''-terphenyl]-4-ylboronic acid was used instead of triphenylen-2-ylboronic acid (MS: [M+H] + =628).

[0160] Synthesis Example 1-26: Synthesis of Compound 1-16 [ka]

[0161] Compound 1-16 was synthesized in the same manner as in Synthesis Example 1-15, except that (phenyl-d5)boronic acid and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine were used instead of [1,1':3',1''-terphenyl]-5'-ylboronic acid and 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (MS: [M+H] + =571).

[0162] Synthesis Example 1-27: Synthesis of Compound 1-17 [ka]

[0163] Compound 1-17 was synthesized in the same manner as in Synthesis Example 1-11, except that J-4 was used instead of A-4 (MS: [M+H] + =626)

[0164] [Synthesis Example 2: Preparation of Compound of Chemical Formula 2] Synthesis Example 2-1: Synthesis of Compound 2-1 Step 1) Synthesis of compound 2-1-a [ka]

[0165] Under a nitrogen atmosphere, 9-([1,1'-biphenyl]-4-yl)-3-bromo-9H-carbazole (15.0 g, 37.7 mmol) and 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (15.3 g, 41.4 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.8 g, 150.6 mmol) dissolved in 62 mL of water was then added and stirred thoroughly, followed by the addition of tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.1 mmol). After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.5 g of compound 2-1-a (yield 64%, MS: [M+H] + =562)

[0166] Step 2) Synthesis of Compound 2-1 [ka]

[0167] Compound 2-1-a (10.0 g, 17.8 mmol), PtO2 (1.2 g, 5.4 mmol), and 89 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over anhydrous magnesium sulfate, concentrated, and the sample was purified by silica gel column chromatography. 3.9 g of compound 2-1 was produced by sublimation purification. (Yield 38%, MS: [M+H] + =580)

[0168] Synthesis Example 2-2: Synthesis of Compound 2-2 Step 1) Synthesis of compound 2-2-a [ka]

[0169] 9-([1,1'-biphenyl]-4-yl)-3-bromo-9H-carbazole (10 g, 25.1 mmol), PtO2 (1.7 g, 7.5 mmol), and 126 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over anhydrous magnesium sulfate, concentrated, and the sample was purified by silica gel column chromatography to produce 7.9 g of compound 2-2-a. (Yield 77%, MS: [M+H] + =409)

[0170] Step 2) Synthesis of Compound 2-2 [ka]

[0171] Under a nitrogen atmosphere, compound 2-2-a (15.0 g, 36.7 mmol) and 9-([1,1'-biphenyl]-2-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (18.0 g, 40.4 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.3 g, 146.9 mmol) dissolved in 61 mL of water was then added and stirred thoroughly, followed by the addition of tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.1 mmol). After 12 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform and washed twice with water. The organic layer was then separated, added to anhydrous magnesium sulfate, and stirred. The filtrate was then filtered and distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography and then purified by sublimation to produce 11.6 g of compound 2-2. (Yield: 49%, MS: [M+H] + =648)

[0172] Synthesis Example 2-3: Synthesis of Compound 2-3 Step 1) Synthesis of compound 2-2-b [ka]

[0173] Under a nitrogen atmosphere, 2-2-a (11 g, 26.9 mmol) and bis(pinacolato)diboron (8.2 g, 32.3 mmol) were added to 220 mL of dioxane and stirred under reflux. Potassium acetate (7.8 g, 80.8 mmol) was then added and thoroughly stirred. Palladium dibenzylideneacetone palladium (0.5 g, 0.8 mmol) and tricyclohexylphosphine (0.5 g, 1.6 mmol) were then added. After 6 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 368 mL of chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. The filtrate was then distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to give white solid compound 2-2-b (9.7 g, 79%, MS: [M+H] + =456.4) was produced.

[0174] Step 2) Synthesis of Compound 2-3 [ka]

[0175] Compound 2-3 was synthesized in the same manner as in Synthesis Example 2-2, except that intermediate 2-2-b was used instead of 9-([1,1'-biphenyl]-2-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (MS: [M+H] + =657).

[0176] Synthesis Example 2-4: Synthesis of Compound 2-4 Step 1) Synthesis of compound 2-4-a [ka]

[0177] Compound 2-4-a was synthesized in the same manner as in Synthesis Example 2-1, except that 9-([1,1'-biphenyl]-3-yl)-3-bromo-9H-carbazole and 9-([1,1'-biphenyl]-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole were used instead of 9-([1,1'-biphenyl]-4-yl)-3-bromo-9H-carbazole and 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (MS: [M+H] + =637).

[0178] Step 2) Synthesis of Compounds 2-4 [ka]

[0179] Compound 2-4 was synthesized in the same manner as in Synthesis Example 2-1, except that compound 2-4-a was used instead of compound 2-1-a (MS: [M+H] + =662).

[0180] Synthesis Example 2-5: Synthesis of Compound 2-5 Step 1) Synthesis of compound 2-5-a [ka]

[0181] Under a nitrogen atmosphere, 3-bromo-9H-carbazole (15.0 g, 60.9 mmol) and 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (24.8 g, 67 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (33.7 g, 243.8 mmol) dissolved in 101 mL of water was then added and stirred thoroughly, followed by the addition of tetrakis(triphenylphosphine)palladium(0) (2.1 g, 1.8 mmol). After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform and washed twice with water. The organic layer was then separated, added to anhydrous magnesium sulfate, and stirred. The filtrate was then filtered and distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.7 g of compound 2-5-a (yield 67%, MS: [M+H] + =410)

[0182] Step 2) Synthesis of compound 2-5-b [ka]

[0183] Compound 2-5-a (10.0 g, 24.5 mmol), PtO2 (1.7 g, 7.3 mmol), and 122 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over anhydrous magnesium sulfate, concentrated, and the sample was purified by silica gel column chromatography to produce 9.1 g of compound 2-5-b. (Yield 88%, MS: [M+H] + =423)

[0184] Step 3) Synthesis of Compounds 2-5 [ka]

[0185] Under a nitrogen atmosphere, compound 2-5-b (15.0 g, 36.7 mmol) and 2-bromo-9,9-dimethyl-9H-fluorene (11.0 g, 40.4 mmol) were added to 300 mL of toluene and stirred under reflux. Sodium tert-butoxide (5.3 g, 55.1 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.1 mmol) were then added. After 6 hours of reaction, the mixture was cooled to room temperature and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was further dissolved in 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 purified by silica gel column chromatography and then purified by sublimation to produce 9.5 g of compound 2-5. (Yield: 42%, MS: [M+H] + =615)

[0186] Synthesis Example 2-6: Synthesis of Compound 2-6 Step 1) Synthesis of compound 2-6-a [ka]

[0187] Under a nitrogen atmosphere, 3-bromo-9H-carbazole (15.0 g, 60.9 mmol) and 9-(phenyl-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (25.1 g, 67 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (33.7 g, 243.8 mmol) dissolved in 101 mL of water was then added and stirred thoroughly, followed by the addition of tetrakis(triphenylphosphine)palladium(0) (2.1 g, 1.8 mmol). After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform and washed twice with water. The organic layer was then separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.1 g of compound 2-6-a (yield 64%, MS: [M+H] + =415)

[0188] Step 2) Synthesis of Compounds 2-6 [ka]

[0189] Under a nitrogen atmosphere, compound 2-6-a (15.0 g, 36.3 mmol) and 3-bromodibenzo[b,d]furan-1,4,6,8,9-d5 (9.9 g, 39.9 mmol) were added to 300 mL of toluene and stirred under reflux. Sodium tert-butoxide (5.2 g, 54.4 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.1 mmol) were then added. After 11 hours of reaction, the mixture was cooled to room temperature and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was further dissolved in 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 purified by silica gel column chromatography and then purified by sublimation to produce 7.9 g of compound 2-6. (Yield: 35%, MS: [M+H] + =585)

[0190] [Manufacturing example: Organic Alloy Manufacturing Manufacturing Example 2-1: Organic Alloy Manufacturing 1 Compound 1-1 and Compound 2-1 were mixed in a weight ratio of 40:60 and placed in a vacuum chamber. -2 The two mixtures were dissolved by increasing the temperature under a pressure of less than Torr, and after 1 hour, the mixture was cooled to room temperature to obtain a solid product. This product was crushed in a mixer to obtain a powder. Organic Alloy I got 1.

[0191] Production Examples 2-2 to 2-18, and Production Examples 2-A to 2-D Except for the fact that the mixed materials were changed as shown in Table 1 below, Organic Alloy Using the same manufacturing method as in 1 Organic Alloy 2~ Organic Alloy 18, and Organic Alloy A~ Organic Alloy Compounds C1 to C4 in Table 1 below are as follows. [ka]

[0192] [Table 1]

[0193] [Example: Production of organic light-emitting element] Example 1: Fabrication of organic light-emitting device A glass substrate coated with a 1400Å-thick thin film of ITO (indium tin oxide) was placed in distilled water with detergent and ultrasonically cleaned. The detergent used was a product of Fischer Co., and the distilled water was distilled water that had been 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 solvents of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaning device. The substrate was then cleaned using oxygen plasma for 5 minutes and then transferred to a vacuum deposition device.

[0194] On the ITO transparent electrode thus prepared, 95 wt% HT-A and 5 wt% PD were thermally vacuum deposited to a thickness of 100 Å to form a hole injection layer, and then HT-A alone was deposited to a thickness of 1150 Å to form a hole transport layer, on which HT-B was thermally vacuum deposited to a thickness of 450 Å as an electron blocking layer.

[0195] Then, a host material prepared in Preparation Example 2-1 was deposited on the electron blocking layer to a thickness of 350 Å. Organic Alloy The light-emitting layer was formed by vacuum deposition of 1 and the dopant GD in a weight ratio of 92:8.

[0196] Next, the following ET-A was vacuum-deposited to a thickness of 50 Å for the hole blocking layer, then the following ET-B and Liq were thermally vacuum-deposited in a 1:1 weight ratio to a thickness of 300 Å for the electron transport layer, and then Yb (ytterbium) was vacuum-deposited to a thickness of 10 Å for the electron injection layer.

[0197] On the electron injection layer, magnesium and silver were deposited in a weight ratio of 1:4 to a thickness of 150 Å to form a cathode, thereby completing an organic light emitting device. [ka]

[0198] During the above process, the deposition rate of the organic material was maintained at 0.4-0.7 Å / sec, the deposition rate of magnesium and silver was maintained at 2 Å / sec, and the vacuum level during deposition was 2×10 -7 ~5×10 -6 The organic light-emitting device was fabricated under a constant pressure of torr.

[0199] Examples 2 to 28 and Comparative Examples 1-1 to 2-4 Organic light-emitting devices of Examples 2 to 28 and Comparative Examples 1-1 to 2-4 were fabricated using the same method as in Example 1, except that the host material was changed as shown in Table 2. In Examples 19 to 28 and Comparative Examples 2-1 to 2-4, a simple mixture of two compounds was used as the host.

[0200] [Experimental Example] The organic light emitting devices fabricated in Examples 1 to 28 and Comparative Examples 1-1 to 2-4 were heat-treated in an oven at 120°C for 30 minutes, then removed from the oven, and a current was applied to measure the voltage, efficiency, and lifetime (T95). The results are shown in Table 2 below.

[0201] At this time, the voltage and efficiency are 10mA / cm 2 The T95 value was measured at a current density of 20 mA / cm. 2 means the time (hr) until the initial brightness decreases to 95%.

[0202] [Table 2]

[0203] Referring to Table 2, it can be seen that when the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 are used as a host in the light-emitting layer of an organic light-emitting device, they have low voltage and high efficiency characteristics and excellent lifespan characteristics compared to the compounds used in the comparative examples. In particular, when Ar3 in the compound represented by Chemical Formula 1 is triphenylene, it can be seen that they exhibit even better efficiency and lifespan characteristics. In addition, the compounds prepared using the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 Organic Alloy It was confirmed that the lifespan was further increased compared to when the compounds of Chemical Formula 1 and Chemical Formula 2 were simply mixed. [Explanation of symbols]

[0204] 1 board 2 Positive electrode 3. Light-emitting layer 4 Negative electrode 5. Hole injection layer 6. Hole transport layer 7 Electron transport layer 8 Electron injection layer 9 Electron suppression layer 10 Hole blocking layer

Claims

1. a positive electrode; a negative electrode; and a light-emitting layer between the positive electrode and the negative electrode, The light-emitting layer includes a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2: [Chemical formula 1] 【Chemistry 130】 In the above Chemical Formula 1, Y is O or S; X １ ~X ３ are each independently CH or N, provided that X １ ~X ３ at least one of is N; Ar １ and Ar ２ are each independently a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S, Ar ３ is an aryl having 6 to 60 carbon atoms substituted with one or more deuterium atoms, or an unsubstituted aryl having 6 to 60 carbon atoms, n is an integer from 1 to 6, R １ are each independently hydrogen or deuterium, [Chemical formula 2] 【Chemistry 131】 In the above Chemical Formula 2, n' and m' are each independently an integer from 1 to 7; R' １ and R' ２ are each independently hydrogen; deuterium; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S, Ar' １ and Ar' ２ are each independently a substituted or unsubstituted aryl having 6 to 12 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing one or more heteroatoms selected from the group consisting of N, O, and S, However, R' １ and R' ２ is deuterium; and / or Ar' １ and Ar' ２ At least one of is substituted with one or more deuterium atoms.

2. X １ ~X ３ The organic light-emitting element according to claim 1 , wherein two or more of

3. Ar １ and Ar ２ are each independently phenyl; phenyl substituted with five deuteriums; biphenylyl; biphenylyl substituted with five deuteriums; terphenylyl; phenanthrenyl; carbazolyl; carbazolyl substituted with six deuteriums; dibenzofuranyl; dibenzothiophenyl; or triphenylenyl.

4. Ar ３ is phenyl; phenyl substituted with five deuterium atoms; biphenylyl; biphenylyl substituted with five to nine deuterium atoms; terphenylyl; terphenylyl substituted with five deuterium atoms; terphenylyl substituted with one phenyl atom; naphthyl; naphthylphenyl; phenanthrenyl; triphenylenyl; triphenylenyl substituted with one to nine deuterium atoms; or triphenylenylphenyl.

5. Ar ３ 2. The organic light-emitting device according to claim 1, wherein is unsubstituted triphenylenyl; or triphenylenyl substituted with 1 to 9 deuterium atoms.

6. 2. The organic light-emitting device according to claim 1, wherein the compound represented by Chemical Formula 1 is any one selected from the group consisting of: 【Chemistry 132】 【Chemistry 133】 【Chemistry 134】 【Chemistry 135】 【Transformation 136】 【Chemistry 137】 【Chemistry 138】 【Chemistry 139】 [Chemistry 140] 【Chemistry 141】 【Chemistry 142】 【Chemistry 143】 【Chemistry 144】 【Chemistry 145】 【Chemistry 146】 【Chemistry 147】 【Chemistry 148】 【Chemistry 149】 [Chemical 150] 【Chemistry 151】 【Chemistry 152】 【Chemistry 153】 【Chemistry 154】 【Chemistry 155】 【Chemistry 156】 【Chemistry 157】 【Chemistry 158】 【Chemistry 159】 [Chemical 160] 【Chemistry 161】 【Chemistry 162】 【Chemical 163】 【Chemistry 164】 【Chemistry 165】 【Chemistry 166】 【Chemistry 167】 【Chemical 168】 【Chemistry 169】 【Chemistry 170】 【Chemistry 171】 【Chemistry 172】 【Chemistry 173】 【Chemistry 174】 【Chemistry 175】 【Chemistry 176】 【Chemistry 177】 【Chemistry 178】 【Chemistry 179】 【Chemistry 180】 【Chemistry 181】 【Chemistry 182】 【Chemistry 183】 【Chemistry 184】 【Chemistry 185】 【Chemical 186】 【Chemistry 187】 【Chemical 188】 【Chemical 189】 【Chemistry 190】 【Chemistry 191】 【Chemistry 192】 【Chemistry 193】 【Chemistry 194】 【Chemistry 195】 【Chemistry 196】 【Chemistry 197】 【Chemistry 198】 【Chemistry 199】 【Chemistry 200】 。

7. The organic light-emitting device according to claim 1, wherein the chemical formula 2 is represented by the following chemical formula 2-1: [Chemical formula 2-1] 【Chemical Engineering 201】 In the above chemical formula 2-1, n', m', R' １ , R' ２ , Ar' １ , and Ar′ ２ is as defined in claim 1.

8. R' １ and R' ２ 2. The organic light-emitting device according to claim 1, wherein each independently represents hydrogen; deuterium; phenyl; or phenyl substituted with 1 to 5 deuterium atoms.

9. Ar' １ and Ar' ２ are each independently phenyl that is unsubstituted or substituted with 1 to 5 deuterium atoms; biphenyl that is unsubstituted or substituted with 1 to 9 deuterium atoms; naphthyl that is unsubstituted or substituted with 1 to 7 deuterium atoms; dimethylfluorenyl that is unsubstituted or substituted with 1 to 13 deuterium atoms; dibenzofuranyl that is unsubstituted or substituted with 1 to 7 deuterium atoms; or dibenzothiophenyl that is unsubstituted or substituted with 1 to 7 deuterium atoms.

10. The organic light-emitting device according to claim 1, wherein the compound represented by Chemical Formula 2 is any one selected from the group consisting of: 【Chemical Engineering 202】 【Chemical 203】 【Chemical 204】 【Chemical 205】 【Chemical 206】 In the above compounds, each methyl group in each chemical formula is independently CH ３ , C.H. ２ D, CHD ２ , or CD ３ is.

11. The organic light-emitting device according to claim 1 , wherein the light-emitting layer comprises an organic alloy of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

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