Organic light-emitting device

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 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 using 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 many researches are being conducted on them.

[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 is often a multi-layer structure composed of different materials to improve the efficiency and safety of the organic light-emitting device, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic light-emitting device structure, when a voltage is applied between two electrodes, holes are injected from the positive electrode and electrons are injected from the negative electrode into the organic layer. When the injected holes and electrons come into contact with each other, excitons are formed, and when the excitons fall back to the ground state, light is emitted.

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

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

[0007] The present invention relates to 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 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; Ar3 is a substituted or unsubstituted aryl having 6 to 60 carbon atoms; n is an integer from 1 to 6, R1 is 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; [Chemical formula 2] [ka] In the above Chemical Formula 2, A' is a benzene ring fused to 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 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 60 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; With the proviso that 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 deuterium. Effect of the Invention

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

[0010] [Figure 1] FIG. 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. [Diagram 2] 1 is a diagram showing an example of an organic light-emitting device consisting of 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. [Diagram 3] FIG. 1 is a diagram showing an example of an organic light-emitting element consisting of 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 PREFERRED EMBODIMENTS

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

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

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

[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 thereto. [ka]

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

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

[0018] In this specification, specific examples of the boron group include a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, and a phenyl boron group, but are not limited to these.

[0019] In this specification, 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 of the alkyl group is 1 to 20. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to yet another embodiment, the number of carbon atoms of 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-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, cyclohexylmethyl, 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, 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 of the alkenyl group is 2 to 20. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, and a styrenyl group, but are not limited thereto.

[0022] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and in one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include 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, but are not limited thereto.

[0023] In the present 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, etc., but is not limited thereto. 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, etc., but is not limited thereto.

[0024] In the present 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 of O, N, Si and S as a hetero element, and the number of carbon atoms is not particularly limited, 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.

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

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

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

[0029] The positive electrode material is preferably a material having a large work function so that holes can be easily injected into the organic layer.Specific examples of the positive electrode 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 SnO2:Sb; 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 having a small work function so that electrons can be easily injected 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 multilayered materials such as LiF / Al or LiO2 / Al.

[0031] Emitting layer The light-emitting layer used in the present invention means a layer capable of emitting light in the visible light region by combining holes and electrons transferred from the positive electrode and the negative electrode. In general, the light-emitting layer includes a host material and a dopant material, and in the present invention, the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 are included as hosts.

[0032] In the above Chemical Formula 1, at least one of X1 to X3 is N, and preferably two or more of them 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. Each of Ar1 and Ar2 may 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 5 deuteriums; biphenylyl; biphenylyl substituted with 5 deuteriums; terphenylyl; terphenylyl substituted with 5 deuteriums; terphenylyl substituted with one 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, R1 is each independently hydrogen or deuterium, Ar1 and Ar2 are each independently phenyl; phenyl substituted with 5 deuterium atoms; biphenylyl; biphenylyl substituted with 5 deuterium atoms; terphenylyl; phenanthrenyl; carbazolyl; carbazolyl substituted with 6 deuterium atoms; dibenzofuranyl; or dibenzothiophenyl; triphenylenyl, and Ar3 is an aryl having 6 to 25 carbon atoms, substituted or unsubstituted with deuterium.

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

[0040] In one embodiment, Y is O or S, at least two of X1 to X3 are N, R1 is each independently hydrogen or deuterium, Ar1 and Ar2 are each independently phenyl; phenyl substituted with 5 deuterium atoms; biphenylyl; biphenylyl substituted with 5 deuterium atoms; terphenylyl; phenanthrenyl; carbazolyl; carbazolyl substituted with 6 deuterium atoms; dibenzofuranyl; or dibenzothiophenyl; triphenylenyl, and Ar3 is phenyl; phenyl substituted with 5 deuterium atoms; biphenylyl; biphenylyl substituted with 5 deuterium atoms; terphenylyl; terphenylyl substituted with 5 deuterium atoms; terphenylyl substituted with 1 phenyl; naphthyl; naphthylphenyl; phenanthrenyl; triphenylenyl; triphenylenyl substituted with 9 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 5 deuterium atoms; biphenylyl; biphenylyl substituted with 5 deuterium atoms; terphenylyl; phenanthrenyl; carbazolyl; carbazolyl substituted with 6 deuterium atoms; dibenzofuranyl; or dibenzothiophenyl; triphenylenyl, and Ar3 is phenyl; phenyl substituted with 5 deuterium atoms; biphenylyl; biphenylyl substituted with 5 deuterium atoms; terphenylyl; terphenylyl substituted with 5 deuterium atoms; terphenylyl substituted with 1 phenyl atom; naphthyl; naphthylphenyl; phenanthrenyl; triphenylenyl; triphenylenyl substituted with 9 deuterium atoms; triphenylenylphenyl; 9,9-dimethylfluorenyl; or 9,9'-spirobifluorenyl.

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

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[0043] The compound represented by Chemical Formula 1 may be prepared, for example, by the following preparation method.

[0044] [Reaction Scheme 1] [ka] In the above reaction scheme 1, the remainder except for X' are as defined above, and each X' is independently a halogen, more preferably each X' is 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 the above formula 1 will be described in more detail in the Preparation Examples below.

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

[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 of the substituents of Ar'1 and Ar'2 contains one or more deuterium; or, if all of R'1 are not deuterium, at least one of the substituents of Ar'1 and Ar'2 may contain one or more deuterium.

[0049] The above-mentioned Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1 to 2-4: [Chemical formula 2-1] [ka] [Chemical formula 2-2] [ka] [Chemical formula 2-3] [ka] [Chemical formula 2-4] [ka] In the above Chemical Formula 2-1 to Chemical Formula 2-4, n', R'1, Ar'1, and Ar'2 are as defined in Formula 2.

[0050] Preferably, each 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 substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms containing one or more heteroatoms selected from the group consisting of N, O, and S.

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

[0053] Preferably, Ar'1 and Ar'2 are each independently phenyl, unsubstituted or 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.

[0054] In this specification, "methyl-biphenylyl" means biphenylyl substituted with one methyl, and "dimethyl-biphenylyl" means biphenylyl substituted with two methyl. 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 have not been replaced, and "methyl-biphenylyl substituted with 1 to 11 deuterium atoms" means that 1 to 11 of all hydrogens contained in the methyl-biphenylyl have been replaced with deuterium. That is, in "methyl-biphenylyl substituted with one deuterium atom", the deuterium may be contained in biphenylyl or the methyl bonded to the biphenylyl.

[0055] In one embodiment, n' is an integer of 6 to 10, R'1 is deuterium, and Ar'1 and Ar'2 are each independently selected from 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 substituted 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 Chemical Formula 2 is 60 to 100%. The "deuterium substitution rate" refers to the number of deuterium 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.

[0057] Representative examples of the compound represented by Formula 2 are as follows: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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[0058] In the above, the methyl groups in each formula are each independently CH3, CH2D, CHD2, or CD3. For example, [ka] wherein the two methyl groups contained in the dimethylfluorenyl may be independently CH3, CH2D, CHD2, or CD3.

[0059] The compound represented by the above formula 2 may be prepared by the following preparation method. [Reaction Scheme 2] [ka] In the reaction formula 2, the remainder except for X″ is as defined above, and each X″ is independently a halogen, more preferably each X″ is independently bromo or chloro.

[0060] The above reaction scheme 2 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the amine substitution reaction can be varied according to those known in the art.

[0061] The method for preparing the compound represented by the formula 2 will be described in more detail in the Preparation Examples below.

[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] Meanwhile, the compound represented by Formula 1 and the compound represented by Formula 2 may be included in the light-emitting layer as a simple mixture or as an organic alloy. The organic compound is a result of a pre-treatment of two or more single organic compounds, and the single organic compounds may have a chemical interaction due to the pre-treatment. The pre-treatment may be, for example, a heat treatment process such as heating and / or sublimation followed by cooling, but is not limited thereto.

[0064] The organic compounds have different properties from each of the individual organic compounds and from a simple mixture in which no chemical interaction exists between the individual organic compounds, because there is a chemical interaction between two or more individual organic compounds as described above. Here, a simple mixture refers to a mixture in which the individual 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 an organic compound of the first organic compound and the second organic compound can exhibit properties different from the properties of the first organic compound, the second organic compound, or a simple mixture thereof.

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

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

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

[0068] The organic compound can be pretreated in various ways, for example, by liquefying or vaporizing the first and second organic compounds through heat treatment and then cooling the heat-treated compounds to solidify them. In addition, the organic compound obtained in a lump-like solid form may be subjected to an additional step of physically pulverizing it using a mixer or the like.

[0069] The organic compound is the result of the pretreatment as described above, and can be supplied using one source during thin film formation, which simplifies the process since it does not require the process control steps required when supplying two or more materials from separate sources.

[0070] In addition, since the organic compounds are the result of the pretreatment as described above, the uniformity and consistency of the deposited material can be ensured 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.

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

[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 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 preferable.

[0074] Specific examples of the hole transport material include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having conjugated and non-conjugated portions.

[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, if necessary.

[0076] The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has a hole injection effect from the positive electrode, has an excellent hole injection effect on the light emitting layer or light emitting material, prevents the movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material, and has excellent thin film forming ability. In addition, 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 surrounding organic layer.

[0077] 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.

[0078] electron suppression layer The organic light-emitting device according to the present invention may include an electron inhibiting layer between the hole transport layer and the light-emitting layer, if necessary.

[0079] The electron inhibiting layer prevents electrons injected from the anode from being recombined in the light emitting layer and passing to the hole transporting 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.

[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 is a layer that receives electrons from the negative electrode or the electron injection layer formed on the negative electrode, transports the electrons to the light-emitting layer, and suppresses the transmission of holes from the light-emitting layer. As the electron transport material, a material that can efficiently receive electrons injected from the negative electrode and transfer them to the light-emitting layer and has high mobility for electrons is preferable.

[0082] Specific examples of the electron transport material include, but are not limited to, Al complex of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are those that have a low work function and are usually followed by an aluminum or silver layer. In particular, cesium, barium, calcium, ytterbium and samarium, each followed by an aluminum or silver layer.

[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, if necessary.

[0084] The electron injection layer is a layer that injects electrons from an 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 forming ability.

[0085] Specific examples of the substance 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.

[0086] Examples of the metal complex compound include, but are not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtholato)gallium.

[0087] 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.

[0088] 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. The hole blocking layer is preferably made of a material having a large ionization energy.

[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 consisting of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. Fig. 2 is a diagram showing an example of an organic light-emitting device consisting of 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. 3 is a diagram showing an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron inhibition layer 9, a light-emitting layer 3, a hole inhibition 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 may be manufactured by sequentially stacking the above-mentioned components. In this case, a metal, a conductive metal oxide, or an alloy thereof may be deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a positive electrode, and the above-mentioned layers may be formed thereon, and a material to be used as a negative electrode may be deposited thereon.

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

[0092] The organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a dual emission device, and may be a bottom emission device which is particularly required to have a relatively high light emitting efficiency.

[0093] 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.

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

[0095] Synthesis Example 1: Synthesis of Compound 1-1 [ka]

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

[0097] 2) Synthesis of Compound B-1 A-1 (30g, 84.5mmol) and bis(pinacolato)diboron (21.5g, 84.5mmol) were added to 600ml of dioxane under a nitrogen atmosphere and stirred and refluxed. Then, potassium acetate (24.9g, 253.6mmol) was added and thoroughly stirred, and then palladium dibenzylideneacetone palladium (1.5g, 2.5mmol) and tricyclohexylphosphine (1.4g, 5.1mmol) were added. After 8 hours of reaction, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was further dissolved in 1132mL of chloroform (30 times the volume), washed twice with water, and 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 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 (15g, 33.6mmol) and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (12g, 33.6mmol) were added to 300ml of THF and stirred and refluxed. Then, potassium carbonate (13.9g, 100.8mmol) was dissolved in 14ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium (0.5g, 1mmol) and 0 (0.6g, 2mmol) were added. After 4 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 647mL of 1,2-dichlorobenzene (30 times the volume), washed twice with water, and 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 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 [ka] Compound 1-2 was prepared in the same manner as in Compound 1-1, except that in Synthesis Example 1, 1-bromo-6-chlorodibenzo[b,d]furan was replaced with 8-bromo-1-chlorodibenzo[b,d]furan, [1,1'-biphenyl]-4-ylboronic acid was replaced with [1,1':4',1''-terphenyl]-4-ylboronic 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 (MS[M+H]+=628.23).

[0100] Synthesis Example 3: Synthesis of Compound 1-3 [ka] Compound 1-3 was prepared in the same manner as in Compound 1-1, except that in Synthesis Example 1, 1-bromo-6-chlorodibenzo[b,d]furan was replaced with 8-bromo-1-chlorodibenzo[b,d]furan-3,4,6,7,9-d5, [1,1'-biphenyl]-4-ylboronic acid was replaced with triphenylen-2-ylboronic 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 (MS[M+H]+=631.25).

[0101] Synthesis Example 4: Synthesis of Compound 1-4 [ka] Compound 1-4 was prepared by the same method as that for compound 1-1, except that in Synthesis Example 1, 1-bromo-6-chlorodibenzo[b,d]furan was replaced with 7-bromo-1-chlorodibenzo[b,d]furan, [1,1'-biphenyl]-4-ylboronic acid was replaced with [1,1'-biphenyl]-3-ylboronic acid, and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine was replaced with 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(phenyl-d5)-1,3,5-triazine (MS[M+H]+=633.26).

[0102] Synthesis Example 5: Synthesis of Compound 1-5 [ka] Compound 1-5 was prepared in the same manner as compound 1-1, except that in Synthesis Example 1, 1-bromo-6-chlorodibenzo[b,d]furan was replaced with 3-bromo-6-chlorodibenzo[b,d]thiophene, [1,1'-biphenyl]-4-ylboronic acid was replaced with (phenyl-d5)boronic 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. (MS[M+H]+=497.18)

[0103] Synthesis Example 6: Synthesis of Compounds 1-6 [ka] Compound 1-6 was prepared by the same method as that for compound 1-1, except that in Synthesis Example 1, 1-bromo-6-chlorodibenzo[b,d]furan was replaced with 7-bromo-1-chlorodibenzo[b,d]thiophene 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 (MS[M+H]+=568.18).

[0104] Synthesis Example 7: Synthesis of Compounds 1-7 [ka] Compound 1-7 was prepared in the same manner as compound 1-1, except that in Synthesis Example 1, 1-bromo-6-chlorodibenzo[b,d]furan was replaced with 4-bromo-6-chlorodibenzo[b,d]thiophene, [1,1'-biphenyl]-4-ylboronic acid was replaced with [1,1'-biphenyl]-3-ylboronic 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 (MS[M+H]+=568.18).

[0105] Synthesis Example 8: Synthesis of Compound 1-8 [ka] Compound 1-8 was prepared in the same manner as in Compound 1-1, except that 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. MS[M+H]+=568.18.

[0106] Synthesis Example 9: Synthesis of Compound 2-1 [ka] Under a nitrogen atmosphere, 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 (20g, 47.4mmol) and 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 (11.5g, 47.4mmol) were added to 400ml of xylene and stirred and refluxed. Then, sodium tert-butoxide (13.7g, 142.3mmol) was added and stirred thoroughly, and bis(tri-tertiarybutylphosphine)palladium (0.7g, 1.4mmol) was added. After reacting for 6 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was dissolved in 1382 mL of 50 times toluene again, washed twice with water, and then the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with toluene and ethyl acetate to produce white solid compound 2-1 (21.3 g, 77%, MS: [M+H]+=583.8).

[0107] Synthesis Example 10: Synthesis of Compound 2-2 [ka] Compound 2-2 was prepared in the same manner as compound 2-1, except that 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 in Synthesis Example 9 was replaced with 3-bromo-1,1'-biphenyl (MS [M+H]+ = 574.31).

[0108] Synthesis Example 11: Synthesis of Compound 2-3 [ka] Compound 2-3 was prepared in the same manner as compound 2-1, except that 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 was replaced with 3-bromodibenzo[b,d]furan in Synthesis Example 9 (MS[M+H]+=588.29).

[0109] Synthesis Example 12: Synthesis of Compound 2-4 [ka] Compound 2-4 was produced by the same method as that for 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 replaced with 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 replaced with 4-bromo-1,1'-biphenyl (MS[M+H]+=584.30).

[0110] Synthesis Example 13: Synthesis of Compound 2-5 [ka] In the 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 is converted to 5-([1,1'-biphenyl]-4-yl-2,3',6-d3)-5,8-dihydroindolo[2,3-c]carbazol Compound 2-5 was produced by the same method as compound 2-1, except that 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 in e-1,2,4,6,7,9,11-d7 (MS[M+H]+=617.36).

[0111] Synthesis Example 14: Synthesis of Compound 2-6 [ka] Compound 2-6 was produced by the same method as that for 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 replaced with 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 replaced with 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 [ka] Compound 2-7 was produced by the same method as 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 replaced with 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 replaced with 4'-chloro-3,5-dimethyl-1,1'-biphenyl (MS[M+H]+=597.31).

[0113] Synthesis Example 16: Synthesis of Compound 2-8 [ka] 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 is replaced with 5-(9,9-dimethyl-9H-fluoren-2-yl-1,3,4,6,8-d5)-5,8-dihydroindolo[2,3-c]carbazole Compound 2-8 was prepared by the same method as compound 2-1, except that ole-2,4,6,7,9,11,12-d7 and 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 were replaced with 2-bromo-9,9-dimethyl-9H-fluorene-1,3,5,6,8-d5 (MS[M+H]+=658.39).

[0114] Synthesis Example 17: Synthesis of Compound 2-9 [ka] Compound 2-9 was produced by the same method as 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 replaced with 5-([1,1'-biphenyl]-4-yl)-5,7-dihydroindolo[2,3-b]carbazole-1,2,4,6,8,10,11,12-d8, and 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 was replaced with 4-bromo-1,1'-biphenyl-3,4',5-d3 (MS[M+H]+=572.29).

[0115] Synthesis Example 18: Synthesis of Compound 2-10 [ka] Compound 2-10 was produced by the same method as 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 replaced with 5-([1,1'-biphenyl]-4-yl-3,4',5-d3)-5,7-dihydroindolo[2,3-b]carbazole-1,2,4,6,8,10,11,12-d8, and 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 was replaced with 3-bromo-1,1'-biphenyl (MS[M+H]+=572.29).

[0116] [Production example: Production of organic compounds]

[0117] Manufacturing Example 1 Compound 1-1 and compound 2-1 were mixed in a weight ratio of 40:60 and placed in a vacuum chamber, and the temperature was raised under a pressure of 10-2 Torr or less to melt the two mixtures, which were then cooled to room temperature after 1 hour to obtain a solid product. This product was pulverized in a mixer to obtain organic compound 1 in powder form.

[0118] Production Examples 2 to 10 and Production Examples A to B Organic compounds 2 to 10 and organic compounds A to B were produced using the same method as that for producing organic compound 1, except that the materials to be mixed were changed as shown in Table 1 below. Compounds GH-1 to GH-4 in Table 1 below are as follows. [ka] [Table 1]

[0119] [Example: Production of organic light-emitting element]

[0120] Example 1 A glass substrate coated with a 1400Å-thick thin film of ITO (Indium Tin Oxide) was placed in distilled water with detergent dissolved therein and ultrasonically cleaned. The detergent used was a product of Fischer Co., and the distilled water used was distilled water that had been filtered a second time with a filter made by Millipore Co. The ITO was cleaned for 30 minutes, then ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning was complete, the substrate 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 for 5 minutes using oxygen plasma, and then transferred to a vacuum deposition device.

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

[0122] Next, a light-emitting layer was formed on the electron inhibiting layer by vacuum-depositing a host material, organic compound 1 prepared in Preparation Example 1, and a dopant material, compound GD, in a weight ratio of 92:8 to a thickness of 350 Å.

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

[0124] Magnesium and silver were deposited on the electron injection layer in a weight ratio of 1:4 to a thickness of 150 Å to form a negative electrode, thereby completing an organic light emitting device. [ka]

[0125] 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 degree during deposition was 2×10 -7 ~5×10 -6 Torr was maintained to fabricate an organic light-emitting device.

[0126] Examples 2 to 10, and Comparative Examples 1 and 2 Organic light emitting devices of Examples 2 to 10 and Comparative Examples 1 and 2 were fabricated using the same method as in Example 1, except that the host material was changed as shown in Table 2 below.

[0127] [Experimental Example] The organic light emitting devices fabricated in Examples 1 to 10 and Comparative Examples 1 and 2 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.

[0128] 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%.

[0129] [Table 2]

[0130] 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 emission layer of an organic light emitting device, they have low voltage and high efficiency characteristics and are excellent in life characteristics compared to the compounds used in the Comparative Examples. In addition, it can be seen that when an organic compound prepared from the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 is used, it has better voltage, efficiency, and life characteristics than when the compounds of Chemical Formula 1 and Chemical Formula 2 are simply mixed and used. [Explanation of symbols]

[0131] 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 138】 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 phenyl; phenyl substituted with five deuteriums; biphenylyl; biphenylyl substituted with five deuteriums; terphenylyl; phenanthrenyl; carbazolyl; carbazolyl substituted with six 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 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; However, the following compounds are excluded from the compounds represented by Chemical Formula 1: 【Chemical 247】 [Chemical formula 2] 【Chemistry 139】 In the above Chemical Formula 2, A' is a benzene ring fused to 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 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 each independently represents a substituted or unsubstituted aryl having 6 to 60 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 at least one of Ar' is deuterium; and / or １ and Ar' ２ At least one of the groups is substituted with one or more deuterium atoms.

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

3. Ar ３ 2. The organic light-emitting device according to claim 1, wherein: is phenyl; phenyl substituted with five deuterium atoms; biphenylyl; biphenylyl substituted with five deuterium atoms; terphenylyl; terphenylyl substituted with five deuterium atoms; terphenylyl substituted with one phenyl atom; naphthyl; naphthylphenyl; phenanthrenyl; triphenylenyl; triphenylenyl substituted with nine deuterium atoms; triphenylenylphenyl; 9,9-dimethylfluorenyl; or 9,9'-spirobifluorenyl.

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

5. 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 140】 【Chemistry 141】 【Chemistry 142】 【Chemistry 143】 【Chemistry 144】 【Chemistry 145】 【Chemistry 146】 【Chemistry 147】 【Chemistry 148】 【Chemistry 149】 【Chemistry 150】 【Chemistry 151】 【Chemistry 152】 【Chemistry 153】 【Chemistry 154】 【Chemistry 155】 【Chemistry 156】 【Chemistry 157】 【Chemistry 158】 【Chemistry 159】 【Chemistry 160】 【Chemistry 161】 【Chemistry 162】 【Chemistry 163】 【Chemistry 164】 【Chemistry 165】 【Chemistry 166】 【Chemistry 167】 【Chemistry 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】 【Chemistry 186】 【Chemistry 187】 【Chemistry 188】 【Chemistry 189】 【Chemistry 190】 【Chemistry 191】 【Chemistry 192】 【Chemistry 193】 【Chemistry 194】 【Chemistry 195】 【Chemistry 196】 【Chemistry 197】 【Chemistry 198】 【Chemistry 199】 【Chemistry 200】 【Chemistry 201】 【Chemistry 202】 【Chemistry 203】 【Chemistry 204】 【Chemistry 205】 【Chemistry 206】 【Chemistry 207】 【Chemistry 208】 。

6. The organic light-emitting device according to claim 1, wherein the chemical formula 2 is represented by any one of the following chemical formulas 2-1 to 2-4: [Chemical formula 2-1] 【Chemistry 209】 [Chemical formula 2-2] 【Chemistry 210】 [Chemical formula 2-3] 【Chemistry 211】 [Chemical formula 2-4] 【Chemistry 212】 In the above Chemical Formula 2-1 to Chemical Formula 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 the is independently hydrogen or deuterium.

8. Ar' １ and Ar' ２ are each independently phenyl unsubstituted or 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.

9. 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: 【Chemistry 213】 【Chemistry 214】 【Chemistry 215】 【Chemistry 216】 【Chemistry 217】 【Chemistry 218】 【Chemical 219】 【Chemistry 220】 【Chemistry 221】 【Chemical 222】 【Chemical 223】 【Chemical 224】 【Chemistry 225】 【Chemical 226】 【Chemical 227】 【Chemical 228】 【Chemical 229】 【Chemistry 230】 【Chemistry 231】 【Chemistry 232】 【Chemistry 233】 【Chemical 234】 【Chemistry 235】 【Chemistry 236】 【Chemistry 237】 【Chemical 238】 【Chemical 239】 【Chemistry 240】 【Chemical 241】 【Chemical 242】 【Chemical 243】 【Chemical 244】 【Chemistry 245】 【Chemical 246】 In the above, each methyl group in each chemical formula is independently CH ３ , C.H. ２ D, C.H.D. ２ , or CDs ３ It is.

10. 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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