Organic light-emitting element

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 - 0056811, filed on April 30, 2021, and Korean Patent Application No. 10 - 2022 - 0053538, filed on April 29, 2022, and all of the contents disclosed in the documents of the Korean patent applications are incorporated herein by reference.

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

Background Art

[0003] Generally, the organic light - emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light - emitting devices that utilize the organic light - emitting phenomenon have a wide viewing angle, excellent contrast, and fast response time, and many studies are being conducted due to their excellent luminance, driving voltage, and response speed characteristics.

[0004] An organic light - emitting device generally has a structure including a positive electrode, a negative electrode, and an organic layer between the positive electrode and the negative electrode. The organic layer often has a multi - layer structure composed of different substances in order to improve the efficiency and safety of the organic light - emitting device. For example, it may include a hole injection layer, a hole transport layer, a light - emitting layer, an electron transport layer, an electron injection layer, etc. In such a structure of an organic light - emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the positive electrode and electrons are injected from the negative electrode. When the injected holes and electrons come into contact, an exciton is formed, and when this exciton falls back to the ground state again, light is emitted.

[0005] There is a continuous demand for the development of new materials for the organic substances used in the organic light - emitting devices as described above.

Prior Art Documents

Patent Documents

[0006]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0007] The present invention relates to an organic light-emitting device with improved driving voltage, efficiency, and lifespan.

Means for Solving the Problems

[0008] To solve the above problems, the present invention provides an organic light-emitting device comprising: a positive electrode; a negative electrode; and a light-emitting layer between the positive electrode and the negative electrode, wherein the light-emitting layer contains a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2: [Chemical Formula 1]

Chem.

Chem.

Advantages of the Invention

[0009] The above-described organic light-emitting device is excellent in driving voltage, efficiency, and lifespan.

Brief Description of the Drawings

[0010]

Figure 1

Figure 2

Figure 3

Embodiments for Carrying Out the Invention

[0011] Hereinafter, a more detailed description will be given to assist in understanding the present invention.

[0012] In the present invention,

Chemical formula

[0013] In the present invention, the term "substituted or unsubstituted" means deuterium; a halogen group; a nitrile group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfinyl group; an arylsulfinyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylamine group; an arylphosphine group; or substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more of N, O, and S atoms, or substituted or unsubstituted with two or more of the exemplified substituents linked together. For example, the "substituent with two or more substituents linked together" may be a biphenyl group. That is, the biphenyl group may be an aryl group and may also be interpreted as a substituent with two phenyl groups linked together.

[0014] In the present invention, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, compounds having the following structures may be used, but are not limited thereto.

Chemical formula

[0015] In the present specification, the oxygen of the ester group in 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, compounds having the following structural formulas may be used, but are not limited thereto.

Chemical formula

[0016] In this specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, compounds having the following structures may be used, but are not limited thereto.

Chemical formula

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

[0018] In this specification, specific examples of the boron group include, but are not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, etc.

[0019] In this specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

[0020] In this specification, the alkyl group may be linear or branched, and its carbon number is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to yet another embodiment, the carbon number of the alkyl group is 1 to 10. According to yet another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohectylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc.

[0021] In this specification, the alkenyl group may be linear or branched, and its carbon number is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another embodiment, the carbon number of the alkenyl group is 2 to 10. According to another embodiment, the carbon number 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.

[0022] In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, there are 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., but are not limited thereto.

[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. As the monocyclic aryl group, the aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. As the polycyclic aryl group, the aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc.

[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,

Chemical formula

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

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

[0027] Hereinafter, the present invention will be described in detail for each component.

[0028] Positive electrode and negative electrode The positive electrode and negative electrode used in the present invention mean the electrodes used in the organic light-emitting element.

[0029] As the positive electrode material, a material having a large work function is generally preferred so that hole injection into the organic layer becomes smooth. Specific examples of the positive electrode 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 metals and oxides 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. However, the present invention is not limited thereto.

[0030] As the negative electrode material, a material having a small work function is generally preferred so that electron injection into the organic layer becomes easy. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structured materials such as LiF / Al or LiO2 / Al. However, the present invention is not limited thereto.

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

[0032] In the formula (1), at least one of X1 to X3 is N, preferably two or more of them are N. In one embodiment, X1 to X3 are all 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 any one or more selected from the group consisting of N, O and S. Ar1 and Ar2 may each be substituted with one or more deuteriums.

[0034] Preferably, Ar1 and Ar2 are each independently phenyl; phenyl substituted with 5 deuteriums; biphenylyl; biphenylyl substituted with 5 deuteriums; terphenylyl; phenanthrenyl; carbazolyl; carbazolyl substituted with 6 deuteriums; dibenzofuranyl; or dibenzothiophenyl; triphenylenyl.

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

[0036] Preferably, Ar3 is phenyl; phenyl substituted with 5 deuteriums; biphenylyl; biphenylyl substituted with 5 deuteriums; terphenylyl; terphenylyl substituted with 5 deuteriums; terphenylyl substituted with 1 phenyl; naphthyl; naphthylphenyl; phenanthrenyl; triphenylenyl; triphenylenyl substituted with 9 deuteriums; triphenylenylphenyl; 9,9-dimethylfluorenyl; or 9,9'-spirobifluorenyl.

[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, and each of Ar1 and Ar2 is 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 an aryl having 6 to 25 carbon atoms which is substituted or unsubstituted with deuterium.

[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, and each of Ar1 and Ar2 is 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 containing any one or more selected from the group consisting of substituted or unsubstituted N, O, and S, and Ar3 is phenyl; phenyl substituted with five deuteriums; biphenylyl; biphenylyl substituted with five deuteriums; terphenylyl; terphenylyl substituted with five deuteriums; terphenylyl substituted with one phenyl; naphthyl; naphthylphenyl; phenanthrenyl; triphenylenyl; triphenylenyl substituted with nine deuteriums; 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, each of Ar1 and Ar2 is 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 phenyl; phenyl substituted with five deuteriums; biphenylyl; biphenylyl substituted with five deuteriums; terphenylyl; terphenylyl substituted with five deuteriums; terphenylyl substituted with one phenyl; naphthyl; naphthylphenyl; phenanthrenyl; triphenylenyl; triphenylenyl substituted with nine deuteriums; triphenylenylphenyl; 9,9-dimethylfluorenyl; or 9,9'-spirobifluorenyl.

[0041] In one embodiment, Y is O or S, X1 to X3 are all N, each R1 is independently hydrogen or deuterium, each of Ar1 and Ar2 is 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 phenyl; phenyl substituted with five deuteriums; biphenylyl; biphenylyl substituted with five deuteriums; terphenylyl; terphenylyl substituted with five deuteriums; terphenylyl substituted with one phenyl; naphthyl; naphthylphenyl; phenanthrenyl; triphenylenyl; triphenylenyl substituted with nine deuteriums; triphenylenylphenyl; 9,9-dimethylfluorenyl; or 9,9'-spirobifluorenyl.

[0042] Typical examples of the compound represented by Chemical Formula 1 are as follows:

Chemical formula

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[0043] The compound represented by the above Chemical Formula 1 may be produced, for example, by the following production method.

[0044] [Reaction Formula 1]

Chem.

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

[0046] The production method of the compound represented by the above Chemical Formula 1 will be more specifically described in the production examples described later.

[0047] The compound represented by the above Chemical Formula 2 is characterized by having one or more deuteriums.

[0048] That is, in Chemical Formula 2, at least one of R'1 is deuterium; at least one of R'1 is deuterium and at least one substituent of Ar'1 and Ar'2 contains one or more deuteriums; or when not all of R'1 are deuterium, at least one substituent of Ar'1 and Ar'2 may contain one or more deuteriums.

[0049] The above Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1 to 2-4: [Chemical Formula 2-1]

Chemical Structure

Chemical Structure

Chemical Structure

Chemical Structure

[0050] Preferably, each of R'1 is independently hydrogen or deuterium.

[0051] Preferably, Ar'1 and Ar'2 are each independently a substituted or unsubstituted aryl having 6 to 21 carbon atoms; or a heteroaryl having 2 to 20 carbon atoms containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S.

[0052] Preferably, Ar'1 and Ar'2 are each independently phenyl; biphenylyl; terphenylyl; dimethylfluorenyl; dibenzofuranyl; or dibenzothiophenyl, and the phenyl; biphenylyl; terphenylyl; dimethylfluorenyl; dibenzofuranyl; or dibenzothiophenyl may each independently be unsubstituted or substituted with one or more substituents of deuterium, methyl, dimethylfluorenyl, dibenzofuranyl, or dibenzothiophenyl.

[0053] Preferably, Ar'1 and Ar'2 are each independently phenyl which is unsubstituted or substituted with 1 to 5 deuteriums; biphenylyl which is unsubstituted or substituted with 1 to 9 deuteriums; methyl-biphenylyl which is unsubstituted or substituted with 1 to 11 deuteriums; dimethyl-biphenylyl which is unsubstituted or substituted with 1 to 13 deuteriums; terphenylyl which is unsubstituted or substituted with 1 to 13 deuteriums; dimethylfluorenyl which is unsubstituted or substituted with 1 to 13 deuteriums; dibenzofuranyl which is unsubstituted or substituted with 1 to 7 deuteriums; dibenzothiophenyl which is unsubstituted or substituted with 1 to 7 deuteriums; dimethylfluorenyl-phenyl which is unsubstituted or substituted with 1 to 17 deuteriums; dibenzofuranyl-phenyl which is unsubstituted or substituted with 1 to 11 deuteriums; or dibenzothiophenyl-phenyl which is unsubstituted or substituted with 1 to 11 deuteriums.

[0054] As used herein, "methyl-biphenylyl" means biphenylyl substituted with one methyl, and "dimethyl-biphenylyl" means biphenylyl substituted with two methyls. Similarly, "dimethylfluorenyl-phenyl" means phenyl substituted with one dimethylfluorene, "dibenzofuranyl-phenyl" means phenyl substituted with one dibenzofuran, and "dibenzothiophenyl-phenyl" means phenyl substituted with one dibenzothiophene. "Unsubstituted methyl-biphenylyl" means that all hydrogens contained in biphenylyl and the methyl bonded to the biphenylyl are not substituted, and "methyl-biphenylyl substituted with 1 to 11 deuteriums" means that 1 to 11 of all hydrogens contained in the methyl-biphenylyl are substituted with deuteriums. That is, in "methyl-biphenylyl substituted with one deuterium", the deuterium may be contained in biphenylyl or the methyl bonded to biphenylyl.

[0055] In one embodiment, n' is an integer from 6 to 10, R'1 is deuterium, and Ar'1 and Ar'2 are each independently phenyl which is unsubstituted or substituted with 1 to 5 deuteriums; biphenylyl which is unsubstituted or substituted with 1 to 9 deuteriums; methyl-biphenylyl which is unsubstituted or substituted with 1 to 11 deuteriums; dimethyl-biphenylyl which is unsubstituted or substituted with 1 to 13 deuteriums; terphenylyl which is unsubstituted or substituted with 1 to 13 deuteriums; dimethylfluorenyl which is unsubstituted or substituted with 1 to 13 deuteriums; dibenzofuranyl which is unsubstituted or substituted with 1 to 7 deuteriums; dibenzothiophenyl which is unsubstituted or substituted with 1 to 7 deuteriums; dimethylfluorenyl-phenyl which is unsubstituted or substituted with 1 to 17 deuteriums; dibenzofuranyl-phenyl which is unsubstituted or substituted with 1 to 11 deuteriums; or dibenzothiophenyl- which is unsubstituted or substituted with 1 to 11 deuteriums.

[0056] Preferably, the deuterium substitution rate of the chemical formula 2 is 60 to 100%. The "deuterium substitution rate" means the ratio of the total number of hydrogens that can be present in the chemical formula 2 to the number of deuteriums contained in the chemical formula 2. Preferably, the deuterium substitution rate of the chemical formula 3 is 65% or more, 70% or more, 75% or more, 80% or more, 85% or more, 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.

[0057] Typical examples of the compound represented by the chemical formula 2 are as follows:

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

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[0058] In the above, each methyl group contained in each chemical formula is independently CH3, CH2D, CHD2, or CD3. For example, in the chemical formula [Chemistry] the two methyl groups contained in the dimethylfluorenyl may each independently be CH3, CH2D, CHD2, or CD3.

[0059] The compound represented by the above chemical formula 2 may be produced by the following production method. [Reaction Formula 2] [Chemistry] In Reaction Formula 2, the remainder excluding X'' is as defined above, and each X'' is independently a halogen, more preferably each is independently bromo or chloro.

[0060] Reaction Formula 2 is an amine substitution reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reaction groups for the amine substitution reaction can be changed according to those known in the art.

[0061] The method for producing the compound represented by Chemical Formula 2 is further embodied in the production examples described later.

[0062] 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.

[0063] On the other hand, 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 may be included in the light-emitting layer as an organic alloy (organic alloy). The organic alloy is the result obtained by pre-treating two or more single organic compounds, and can have a chemical interaction between the single organic compounds by the pre-treatment. The pre-treatment may be, for example, one cooled after a heat treatment process such as heating and / or sublimation, but is not limited thereto.

[0064] The organic alloySince there is a chemical interaction between two or more single organic compounds as described above, it has characteristics different from those of each single organic compound and a simple mixture in which there is no chemical interaction between the single organic compounds. Here, the simple mixture refers to a mixture obtained by simply physically mixing each single organic compound without any pretreatment. That is, the simple mixture of the first organic compound and the second organic compound exhibits the characteristics of the first organic compound, the second organic compound, or a combination thereof, while the organic alloy can exhibit characteristics different from those of the first organic compound, the second organic compound, or the simple mixture thereof.

[0065] For example, the emission wavelength of the organic alloy may be different from the emission wavelengths of the first organic compound, the second organic compound, and the simple mixture thereof.

[0066] Also, the color of the organic alloy may be different from the colors of the first organic compound, the second organic compound, and the simple mixture thereof.

[0067] Also, the glass transition temperature (Tg) of the organic alloy may be different from the glass transition temperatures (Tg) of the first organic compound, the second organic compound, and the simple mixture thereof. Also, the crystallization temperature (Tc) of the organic alloy may be different from the crystallization temperatures of the first organic compound, the second organic compound, and the simple mixture thereof. Also, the melting temperature (Tm) of the organic alloy may be different from the melting temperatures of the first organic compound, the second organic compound, and the simple mixture thereof.

[0068] The organic alloy is pretreated in various ways. For example, it is obtained from the steps of 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. Also, the organic alloyAn additional step of physically pulverizing using a mixer or the like may further be performed.

[0069] The organic alloy is the result obtained by the pretreatment as described above, and can be supplied using one source during thin film formation. Thereby, since the process control step required when supplying two or more substances from separate sources is not necessary, the process can be simplified.

[0070] Also, since the organic alloy is the result obtained by the pretreatment as described above, the uniformity and consistency of the deposited substance can be ensured as compared with the case where two or more single organic compounds are respectively supplied from separate sources or 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 a continuous process, thin films having substantially the same ratio of components can be continuously produced, thereby enhancing the reproducibility and reliability of the thin films.

[0071] The dopant material is not particularly limited as long as it is a substance used in an organic light emitting device. For example, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, as aromatic amine derivatives, there are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periflanthene having an arylamino group, and as styrylamine compounds, compounds in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, and a substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but are not limited thereto. Also, as metal complexes, there are iridium complexes, platinum complexes, etc., but are not limited thereto.

[0072] 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.

[0073] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. As the hole transport material, a material that can receive hole transport from the positive electrode or the hole injection layer and transfer it to the light-emitting layer, and a material with high mobility for holes is preferable.

[0074] Specific examples of the hole transport material include arylamine-based organic substances, conductive polymers, and block copolymers that exist together with a conjugated part and a non-conjugated part, but are not limited thereto.

[0075] Hole injection layer The organic light-emitting device according to the present invention may further include a hole injection layer between the positive electrode and the hole transport layer as needed.

[0076] The hole injection layer is a layer that injects holes from the electrode. As the hole injection material, a compound having the ability to transport holes, having an excellent hole injection effect from the positive electrode, an excellent hole injection effect on the light-emitting layer or the light-emitting material, preventing the transfer of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material, and having excellent thin film forming ability is preferable. Further, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the peripheral organic layer.

[0077] Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, and conductive polymers such as polyaniline and polythiophene, but are not limited thereto.

[0078] Electron blocking layer The organic light-emitting device according to the present invention may include an electron blocking layer between the hole transport layer and the light-emitting layer as needed.

[0079] The electron blocking layer prevents electrons injected from the negative electrode from passing to the hole transport layer without recombination in the light-emitting layer, and is also called an electron blocking layer. A substance having a smaller electron affinity than the electron transport layer is preferable for the electron blocking layer.

[0080] 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.

[0081] The electron transport layer receives electrons from the negative electrode or an electron injection layer formed on the negative electrode and transports the electrons to the light-emitting layer, and also suppresses the transfer of holes from the light-emitting layer. As the electron transport material, a material that can favorably receive injection of electrons from the negative electrode and transfer them to the light-emitting layer and has a high mobility with respect to electrons is preferable.

[0082] Specific examples of the electron transport material include an Al complex of 8-hydroxyquinoline; a complex containing Alq3; an organic radical compound; a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer is used together with any desired cathode material as in the prior art. In particular, examples of suitable cathode materials are normal materials having a low work function followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.

[0083] 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 as needed.

[0084] The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an excellent electron injection effect from the negative electrode and on the light-emitting layer or light-emitting material, prevents the excitons generated in the light-emitting layer from moving to the hole injection layer, and preferably uses a compound with excellent thin film forming ability.

[0085] Specific examples of the substances used in the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but are not limited thereto.

[0086] Examples of the metal complex compounds include lithium 8-hydroxyquinolinate, zinc bis(8-hydroxyquinolinate), copper bis(8-hydroxyquinolinate), manganese bis(8-hydroxyquinolinate), aluminum tris(8-hydroxyquinolinate), aluminum tris(2-methyl-8-hydroxyquinolinate), gallium tris(8-hydroxyquinolinate), beryllium bis(10-hydroxybenzo[h]quinolinate), zinc bis(10-hydroxybenzo[h]quinolinate), gallium bis(2-methyl-8-quinolinato)chloride, gallium bis(2-methyl-8-quinolinato)(o-cresolato), aluminum bis(2-methyl-8-quinolinato)(1-naphtholato), gallium bis(2-methyl-8-quinolinato)(2-naphtholato), etc., but are not limited thereto.

[0087] Hole suppression layer The organic light-emitting device according to the present invention may include a hole suppression layer between the electron transport layer and the light-emitting layer as required.

[0088] The hole suppression layer prevents the holes injected from the positive electrode from passing to the electron transport layer without recombining in the light-emitting layer, and a substance with a large ionization energy is preferably used for the hole suppression layer.

[0089] Organic light-emitting device The structure of the 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 including a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. Further, FIG. 2 is a diagram showing an example of an organic light-emitting device including 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. Further, FIG. 3 is a diagram showing an example of an organic light-emitting device including a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light-emitting layer 3, a hole blocking layer 10, an electron transport layer 7, an electron injection layer 8, and a negative electrode 4.

[0090] The organic light-emitting device according to the present invention can be manufactured by sequentially laminating the above-described configurations. At this time, using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation, a metal, a metal oxide having conductivity, or an alloy thereof is vapor-deposited on a substrate to form a positive electrode, and after forming each of the above-described layers thereon, a substance used as a negative electrode is further vapor-deposited thereon to manufacture the device.

[0091] In addition to this method, an organic light-emitting device can be fabricated by sequentially depositing on a substrate, in reverse order from the negative electrode material to the positive electrode material of the above-described configuration (WO2003 / 012890). Further, the light-emitting layer can be formed by not only vacuum evaporation but also solution coating of a host and a dopant. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

[0092] The organic light-emitting device according to the present invention may be a bottom emission element, a top emission element, or a double-sided emission element, and particularly may be a bottom emission element that requires relatively high luminous efficiency.

[0093] The manufacturing of the organic light-emitting device according to the present invention described above will be specifically described in the following examples. However, the following examples are merely for illustrating the present invention, and the scope of the present invention is not limited thereby.

[0094] [Synthesis Example: Production of the Compound of Chemical Formula 1 and the Compound of Chemical Formula 2]

[0095] Synthesis Example 1: Synthesis of Compound 1-1 [Chemical Formula]

[0096] 1) Synthesis of Compound A-1 Under a nitrogen atmosphere, 1-bromo-6-chlorodibenzo[b,d]furan (20 g, 71 mmol) and [1,1'-biphenyl]-4-ylboronic acid (14.1 g, 71 mmol) were placed in 400 ml of THF, stirred, and refluxed. Then, potassium carbonate (29.5 g, 213.1 mmol) was dissolved in 88 ml of water, added, and stirred thoroughly. Thereafter, tetrakis(triphenylphosphine)palladium(0) (1.1 g, 2.1 mmol) was added. After reacting for 3 hours, it was cooled to room temperature. After separating the organic layer and the aqueous layer, the organic layer was distilled. This was further dissolved by adding 1260 mL of toluene 50 times, 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 purified through a silica column using toluene and ethyl acetate to produce a white solid compound A-1 (15.6 g, 62%, MS: [M+H]+ = 355.8).

[0097] 2) Synthesis of Compound B-1 Under a nitrogen atmosphere, A-1 (30 g, 84.5 mmol) and bis(pinacolato)diboron (21.5 g, 84.5 mmol) were placed in 600 ml of dioxane and stirred and refluxed. Then, potassium acetate (24.9 g, 253.6 mmol) was added and stirred well, followed by the addition of palladium dibenzylideneacetone palladium (1.5 g, 2.5 mmol) and tricyclohexylphosphine (1.4 g, 5.1 mmol). After reacting for 8 hours, it was cooled to room temperature, and the organic layer was filtered to remove salts. Then, the filtered organic layer was distilled. This was further dissolved in 1132 mL of chloroform 30 times and washed twice with water. After separating the organic layer, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a beige solid compound B-1 (23.4 g, 62%, MS: [M+H]+ = 447.4).

[0098] 3) Synthesis of Compound 1-1 Under a nitrogen atmosphere, B-1 (15 g, 33.6 mmol) and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (12 g, 33.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (13.9 g, 100.8 mmol) was dissolved in 14 ml of water and added and stirred well, followed by the addition of bis(tri-tert-butylphosphine)palladium (0.5 g, 1 mmol) and 0 (0.6 g, 2 mmol). After reacting for 4 hours, it was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 647 mL of 1,2-dichlorobenzene 30 times, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from DCB and ethyl acetate to produce a white solid compound 1-1 (10.8 g, 50%, MS: [M+H]+ = 642.7).

[0099] Synthesis Example 2: Synthesis of Compound 1-2

Chemical Structure

[0100] Synthesis Example 3: Synthesis of Compound 1-3

Chemical formula

[0101] Synthesis Example 4: Synthesis of Compound 1-4

Chemical formula

[0102] Synthesis Example 5: Synthesis of Compound 1-5

Chemical formula

[0103] Synthesis Example 6: Synthesis of Compound 1-6

Chemical formula

[0104] Synthesis Example 7: Synthesis of Compound 1-7 [Chemical formula] Compound 1-7 was produced in the same production method as that of Compound 1-1, except that in Synthesis Example 1, 1-bromo-6-chlorodibenzo[b,d]furan was changed to 4-bromo-6-chlorodibenzo[b,d]thiophene, [1,1'-biphenyl]-4-ylboronic acid was changed to [1,1'-biphenyl]-3-ylboronic acid, and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine was changed to 2-chloro-4,6-diphenyl-1,3,5-triazine (MS [M+H]+ = 568.18).

[0105] Synthesis Example 8: Synthesis of Compound 1-8 [Chemical formula] In Synthesis Example 1, 1-bromo-6-chlorodibenzo[b,d]furan was replaced with 2-bromo-6-chlorodibenzo[b,d]thiophene, [1,1'-biphenyl]-4-ylboronic acid was replaced with phenylboronic acid, and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine was replaced with 2-chloro-4,6-diphenyl-1,3,5-triazine. Compound 1-8 was produced in the same production method as that of Compound 1-1 (MS [M+H]+ = 568.18).

[0106] Synthesis Example 9: Synthesis of Compound 2-1

Chemical Structure

[0107] Synthesis Example 10: Synthesis of Compound 2-2 [Chemical formula] Compound 2-2 was produced by the same production method as that of compound 2-1, except that 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 was changed to 3-bromo-1,1'-biphenyl in Synthesis Example 9 (MS [M+H]+ = 574.31).

[0108] Synthesis Example 11: Synthesis of Compound 2-3 [Chemical formula] Compound 2-3 was produced by the same production method as that of compound 2-1, except that 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 was changed to 3-bromodibenzo[b,d]furan in Synthesis Example 9 (MS [M+H]+ = 588.29).

[0109] Synthesis Example 12: Synthesis of Compound 2-4 [Chemical formula] Compound 2-4 was produced by the same production method as that of compound 2-1, except that 5-([1,1'-biphenyl]-4-yl-2,3',6-d3)-5,8-dihydroindolo[2,3-c]carbazole-1,2,3,4,6,7,9,10,11,12-d10 was changed to 5-(4'-methyl-[1,1'-biphenyl]-4-yl-2,3',6-d3)-5,8-dihydroindolo[2,3-c]carbazole-2,4,6,7,10,11-d6 and 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 was changed to 4-bromo-1,1'-biphenyl in Synthesis Example 9 (MS [M+H]+ = 584.30).

[0110] Synthesis Example 13: Synthesis of Compound 2-5 [Chemical formula] Compound 2-5 was produced by the same production method as the production method of Compound 2-1, except that 5-([1,1'-biphenyl]-4-yl-2,3',6-d3)-5,8-dihydroindolo[2,3-c]carbazole-1,2,3,4,6,7,9,10,11,12-d10 in Synthesis Example 9 was changed to 5-([1,1'-biphenyl]-4-yl-2,3',6-d3)-5,8-dihydroindolo[2,3-c]carbazole-1,2,4,6,7,9,11-d7, and 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 was changed to 9,9-dimethyl-9H-fluorene-1,3,4,5,6,8-d6 (MS [M+H]+ = 617.36).

[0111] Synthesis Example 14: Synthesis of Compound 2-6 [Chemical formula] Compound 2-6 was produced by the same production method as the production method of Compound 2-1, except that 5-([1,1'-biphenyl]-4-yl-2,3',6-d3)-5,8-dihydroindolo[2,3-c]carbazole-1,2,3,4,6,7,9,10,11,12-d10 in Synthesis Example 9 was changed to 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindolo[2,3-c]carbazole-1,2,4,6,7,9,11-d7, and 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 was changed to 9,9-dimethyl-9H-fluorene-1,3,4,6,8-d5 (MS [M+H]+ = 613.33).

[0112] Synthesis Example 15: Synthesis of Compound 2-7 [Chemical formula] Compound 2-7 was produced in the same production method as that of Compound 2-1, except that in Synthesis Example 9, 5-([1,1'-biphenyl]-4-yl-2,3',6-d3)-5,8-dihydroindolo[2,3-c]carbazole-1,2,3,4,6,7,9,10,11,12-d10 was changed to 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindolo[2,3-c]carbazole-1,2,4,6,7,9,11,12-d8, and 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 was changed to 4'-chloro-3,5-dimethyl-1,1'-biphenyl (MS [M+H]+ = 597.31).

[0113] Synthesis Example 16: Synthesis of Compound 2-8

Chemical formula

[0114] Synthesis Example 17: Synthesis of Compound 2-9

Chemical formula

[0115] Synthesis Example 18: Synthesis of Compound 2-10

Chemical Structure

[0116] [Production Example: Organic alloy Production]

[0117] Production Example 1 Compound 1-1 and Compound 2-1 were mixed in a weight ratio of 40:60 and placed in a vacuum chamber. The temperature was raised under a pressure of 10-2 Torr or less to dissolve the two mixtures. After 1 hour, the mixture was cooled to room temperature to obtain a solid product. This product was pulverized with a mixer to obtain an organic alloy 1 in powder form.

[0118] Production Examples 2 to 10 and Production Examples A to B Except for changing the materials to be mixed as shown in Table 1 below, the same method as the production method of organic alloy 1 was used to produce organic alloy 2 to organic alloy 10, and organic alloy A to organic alloy B. Compounds GH-1 to GH-4 in Table 1 below are as follows.

Chemical Structure

Table 1

[0119] [Examples: Production of Organic Light-Emitting Devices]

[0120] Example 1 A glass substrate with a thin film coating of ITO (Indium Tin Oxide) with a thickness of 1400 Å was placed in distilled water in which a detergent was dissolved and cleaned with ultrasonic waves. At this time, a product of Fischer Co. was used as the detergent, and distilled water that had been secondarily filtered with a filter of Millipore Co. was used as the distilled water. After cleaning the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes each. After the distilled water cleaning was completed, ultrasonic cleaning was performed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaning device. In addition, the substrate was cleaned with oxygen plasma for 5 minutes, and then the substrate was transported to a vacuum evaporation device.

[0121] On the thus-prepared ITO transparent electrode, 95 wt% of the compound HT-A and 5 wt% of the compound PD were thermally vacuum-deposited to a thickness of 100 Å to form a hole injection layer, and then only the compound HT-A was deposited to a thickness of 1150 Å to form a hole transport layer. On top of that, the following compound HT-B was thermally vacuum-deposited to a thickness of 450 Å as an electron blocking layer.

[0122] Subsequently, on the electron blocking layer, as a host material, the organic alloy 1 prepared in Production Example 1 and the dopant material, compound GD, were vacuum-deposited at a weight ratio of 92:8 to form a light-emitting layer.

[0123] Subsequently, as a hole blocking layer, the following compound ET-A was vacuum-deposited to a thickness of 50 Å. Subsequently, as an electron transport layer, the following compound ET-B and compound Liq were thermally vacuum-deposited at a weight ratio of 1:1 to a thickness of 300 Å, and then as an electron injection layer, Yb (ytterbium) was vacuum-deposited to a thickness of 10 Å.

[0124] On the electron injection layer, magnesium and silver were deposited at a weight ratio of 1:4 to a thickness of 150 Å to form a negative electrode, and an organic light-emitting device was manufactured.

Chemical formula

[0125] In 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 degree of vacuum during deposition was maintained at 2×10 -7 ~5×10 -6 torr to fabricate the organic light-emitting device.

[0126] Examples 2 - 10 and Comparative Examples 1 - 2 Except for changing the host material as shown in Table 2 below, the organic light-emitting devices of Examples 2 - 10 and Comparative Examples 1 - 2 were fabricated using the same method as in Example 1 above.

[0127] [Experimental Example] The organic light-emitting devices fabricated in Examples 1 to 10 and Comparative Examples 1 to 2 were taken out after being heat-treated in an oven at 120°C for 30 minutes, a current was applied, and the voltage, efficiency, and lifetime (T95) were measured. The results are shown in Table 2 below.

[0128] At this time, the voltage and efficiency were measured by applying a current density of 10 mA / cm 2 , and T95 means the time (hr) until the initial luminance decreases to 95% at a current density of 20 mA / cm 2 .

[0129]

Table 2

[0130] Referring to Table 2 above, when the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 are used as the host of the light-emitting layer of the organic light-emitting device, it can be confirmed that they have low voltage and high efficiency characteristics compared to the compounds used in the comparative examples, and are excellent in lifetime characteristics. In addition, when the organic alloy is used, it can be confirmed that the compounds of Chemical Formula 1 and Chemical Formula 2 are superior in terms of voltage, efficiency, and lifetime characteristics compared to the case where the compounds of Chemical Formula 1 and Chemical Formula 2 are simply mixed and used.

Description of Symbols

[0131] 1 Substrate 2 Anode 3 Light-emitting layer 4 Cathode 5 Hole injection layer 6 Hole transport layer 7 Electron transport layer 8 Electron injection layer 9 Electron blocking 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, wherein the light-emitting layer contains a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2: an organic light-emitting device: [Chemical Formula 1] 【Chemical 138】 In Chemical Formula 1, Y is O or S, X １ ~X ３ is each independently CH or N, provided that X １ ~X ３ at least one of which is N, Ar 1 and Ar 2 are each independently phenyl; phenyl substituted with 5 deuteriums; biphenylyl; biphenylyl substituted with 5 deuteriums; terphenylyl; phenanthrenyl; carbazolyl; carbazolyl substituted with 6 deuteriums; dibenzofuranyl; dibenzothiophenyl; or triphenylenyl, Ar ３ is a substituted or unsubstituted aryl having 6 to 60 carbon atoms, n is an integer from 1 to 6, R １ each independently is hydrogen; deuterium; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a heteroaryl having 2 to 60 carbon atoms containing any one or more selected from the group consisting of substituted or unsubstituted N, O, and S, provided that the following compound is excluded from the compound represented by Chemical Formula 1: 【Chemical 247】 [Chemical Formula 2] 【Chemical 139】 In Chemical Formula 2, A' is a benzene ring fused with two adjacent pentagonal rings, n' is an integer from 1 to 10, R' １ is hydrogen; deuterium; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a heteroaryl having 2 to 60 carbon atoms containing any one or more selected from the group consisting of substituted or unsubstituted N, O, and S, Ar' １ and Ar' ２ each independently is a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a heteroaryl having 2 to 60 carbon atoms containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S, However, at least one of R' １ is deuterium; and / or at least one of Ar' １ and Ar' ２ is substituted with one or more deuteriums.

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

3. Ar ３ is phenyl; phenyl substituted with five deuteriums; biphenylyl; biphenylyl substituted with five deuteriums; terphenylyl; terphenylyl substituted with five deuteriums; terphenylyl substituted with one phenyl; naphthyl; naphthylphenyl; phenanthrenyl; triphenylenyl; triphenylenyl substituted with nine deuteriums; triphenylenylphenyl; 9,9-dimethylfluorenyl; or 9,9'-spirobifluorenyl, the organic light-emitting device according to claim 1.

4. R １ The organic light-emitting device according to claim 1, wherein each of

5. The compound represented by Chemical Formula 1 is any one selected from the group consisting of the following: the organic light-emitting device according to Claim 1: 【Chemical 140】 【Chemical 141】 【Chemical 142】 【Chemical 143】 【Chemical 144】 【Chemical 145】 【Chemical 146】 【Chemical 147】 【Chemical 148】 【Chemical 149】 【Chemical 150】 【Chemical 151】 【Chemical 152】 【Chemical 153】 【Chemical 154】 【Chemical 155】 【Chemical 156】 【Chemical 157】 【Chemical 158】 【Chemical 159】 【Chemical 160】 【Chemical 161】 【Chemical 162】 【Chemical 163】 【Chemical 164】 【Chemical 165】 【Chemical 166】 【Chemical 167】 【Chemical 168】 【Chemical 169】 【Chemical 170】 【Chemical 171】 【Chemical 172】 【Chemical 173】 【Chemical 174】 【Chemical 175】 【Chemical 176】 【Chemical 177】 【Chemical 178】 【Chemical 179】 【Chemical Formula 180】 【Chemical 181】 【Chemical 182】 【Chemical 183】 【Chemical 184】 【Chemical 185】 【Chemical Formula 186】 【Chemical 187】 【Chemical 188】 【Chemical 189】 【Chemical 190】 【Chemical 191】 【Chemical 192】 【Chemical 193】 【Chemical 194】 【Chemical 195】 【Chemical Formula 196】 【Chemical 197】 【Chemical 198】 【Chemical 199】 【Chemical 200】 【Chemical 201】 【Chemical 202】 【Chemical 203】 【Chemical 204】 【Chemical 205】 【Chemical 206】 【Chemical 207】 【Chemical 208】 。

6. Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1 to 2-4: the organic light-emitting device according to Claim 1: [Chemical Formula 2-1] 【Chemical 209】 [Chemical Formula 2-2] 【Chemical 210】 [Chemical Formula 2-3] 【Chemical 211】 [Chemical Formula 2-4] 【Chemical 212】 In Chemical Formulas 2-1 to 2-4, n', R' １ , Ar' １ , and Ar' ２ is as defined in claim 1.

7. R' １ The organic light-emitting device according to claim 1, wherein each of them is independently hydrogen or deuterium.

8. Ar' １ and Ar' ２ is each independently unsubstituted or phenyl substituted with 1 to 5 deuteriums; biphenylyl unsubstituted or substituted with 1 to 9 deuteriums; methyl-biphenylyl unsubstituted or substituted with 1 to 11 deuteriums; dimethyl-biphenylyl unsubstituted or substituted with 1 to 13 deuteriums; terphenylyl unsubstituted or substituted with 1 to 13 deuteriums; dimethylfluorenyl unsubstituted or substituted with 1 to 13 deuteriums; dibenzofuranyl unsubstituted or substituted with 1 to 7 deuteriums; dibenzothiophenyl unsubstituted or substituted with 1 to 7 deuteriums; dimethylfluorenyl-phenyl unsubstituted or substituted with 1 to 17 deuteriums; dibenzofuranyl-phenyl unsubstituted or substituted with 1 to 11 deuteriums; or dibenzothiophenyl-phenyl unsubstituted or substituted with 1 to 11 deuteriums, the organic light-emitting element according to claim 1.

9. The compound represented by Chemical Formula 2 is any one selected from the group consisting of the following: the organic light-emitting device according to Claim 1: 【Chemical 213】 【Chemical 214】 【Chemical 215】 【Chemical 216】 【Chemical 217】 【Chemical 218】 【Chemical 219】 【Chemical 220】 【Chemical 221】 【Chemical 222】 【Chemical 223】 【Chemical 224】 【Chemical 225】 【Chemical 226】 【Chemical 227】 【Chemical 228】 【Chemical 229】 【Chemical 230】 【Chemical 231】 【Chemical 232】 【Chemical 233】 【Chemical 234】 【Chemical 235】 【Chemical 236】 【Chemical 237】 【Chemical 238】 【Chemical 239】 【Chemical 240】 【Chemical formula 241】 【Chemical 242】 【Chemical 243】 【Chemical 244】 【Chemical 245】 【Chemical Formula 246】 In the above, each methyl group contained in each chemical formula is independently CH ３ , CH ２ D, CHD ２ , or CD ３ .

10. The light-emitting layer contains an organic alloy of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2: the organic light-emitting device according to Claim 1.

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