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. 10-2021-0059329 filed on May 7, 2021, and Korean Patent Application No. 10-2022-0056391 filed on May 9, 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 these devices.

[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; 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; Ar3 is a substituent represented by the following chemical formula 1-1 or 1-2: [Chemical formula 1-1] [ka] [Chemical formula 1-2] [ka] In the above Chemical Formulas 1-1 and 1-2, p is an integer from 1 to 8; q is an integer from 1 to 10; R 11 and R 12 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 containing at least one selected from the group consisting of N, O, and S; A is a benzene ring fused to two adjacent pentagonal rings; Ar 12 is a substituted or unsubstituted aryl having 6 to 60 carbon atoms, [Chemical formula 2] [ka] In the above Chemical Formula 2, n' and m' are each independently an integer from 1 to 7; R'1 and R'2 are each independently hydrogen; deuterium; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms 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 17 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 and R'2 is deuterium; and / or at least one of Ar'1 and Ar'2 is substituted with one or more deuterium atoms. Effect of the Invention

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

[0010] [Figure 1] 1 is a diagram showing an example of an organic light-emitting device composed of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. FIG. [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. [Diagram 3] 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, 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 this specification, [ka] denotes a bond that is connected to another substituent.

[0013] In the present specification, 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, nitrile, nitro, hydroxy, carbonyl, ester, imide, amino, phosphine oxide, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfoxy, arylsulfoxy, silyl, boron, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, aralkenyl, alkylaryl, alkylamine, aralkylamine, heteroarylamine, arylamine, arylphosphine, 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-listed substituents. 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 this specification, 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 compound having the following structure, 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] As used herein, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0020] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms 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-methylbutyl, 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, but are not limited to, 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.

[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, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

[0023] In 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, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. The polycyclic 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 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. The present invention will be described in detail below for each component.

[0027] 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.

[0028] 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; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0029] 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 multilayer structures such as LiF / Al or LiO2 / Al.

[0030] 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.

[0031] In one embodiment, the compound represented by Chemical Formula 1 may contain one or more deuterium atoms, i.e., one or more R1 in Chemical Formula 1 may be deuterium atoms, and / or at least one of Ar1 to Ar3 may be substituted with one or more deuterium atoms.

[0032] In the above Chemical Formula 1, at least one of X1 to X3 is N, and preferably all of them 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; carbazolyl; dibenzofuranyl; or dibenzothiophenyl.

[0035] Preferably, each R1 is independently hydrogen or deuterium.

[0036] Ar3 is a carbazole substituent represented by the above formula 1-1 or an indolocarbazole substituent represented by the above formula 1-2. Ar3 may be substituted with one or more deuterium atoms.

[0037] When Ar3 is a substituent represented by the above-mentioned chemical formula 1-1, it is preferably R 11 are each independently hydrogen; deuterium; phenyl; or phenyl substituted with five deuteriums.

[0038] When Ar3 is a substituent represented by the above-mentioned chemical formula 1-1, p is an integer of 1 to 8, and R 11 may be deuterium or phenyl.

[0039] Specifically, when Ar3 is a substituent represented by the above-mentioned formula 1-1, p is 1, and R 11 may be phenyl.

[0040] Or, when Ar3 is a substituent represented by the above-mentioned chemical formula 1-1 and p is 2 to 8, R 11 are all deuterium or R 11 One of the groups may be phenyl and the rest may all be deuterium.

[0041] Or, when Ar3 is a substituent represented by the above-mentioned chemical formula 1-1, p is an integer of 4 to 8 or 6 to 8, and R 11 may be deuterium.

[0042] Preferably, the formula 1-2 can be represented as the following formula 1-2-a: [Chemical formula 1-2-a] [ka] In the above Chemical Formula 1-2-a, q, R 12 , and Ar 12 is as defined in Chemical Formula 1-2. When Ar3 is a substituent represented by the above formula 1-2, R 12 are each independently hydrogen or deuterium, and Ar 12 may be a substituted or unsubstituted aryl having 6 to 20 carbon atoms. 12 are each independently hydrogen or deuterium, and Ar 12 is phenyl.

[0043] When Ar3 is a substituent represented by the above formula 1-2-a, four R 12 is hydrogen, and six R 12 is deuterium, and Ar 12 may be phenyl.

[0044] In one embodiment, X1 to X3 in Chemical Formula 1 are all N, and Ar1 and Ar2 may each independently be phenyl; phenyl substituted with five deuteriums; biphenylyl; biphenylyl substituted with five deuteriums; carbazolyl; dibenzofuranyl; or dibenzothiophenyl.

[0045] In one embodiment, X1 to X3 in Chemical Formula 1 are all N, Ar1 and Ar2 are each independently phenyl; phenyl substituted with 5 deuterium atoms; biphenylyl; biphenylyl substituted with 5 deuterium atoms; carbazolyl; dibenzofuranyl; or dibenzothiophenyl, and R1 may each independently be hydrogen or deuterium.

[0046] In one embodiment, X1 to X3 in Formula 1 are all N, R1 is each independently hydrogen or deuterium, Ar3 is a substituent represented by Formula 1-1, p is an integer from 1 to 8, and R 11 may each independently be hydrogen; deuterium; phenyl; or phenyl substituted with five deuteriums.

[0047] In one embodiment, X1 to X3 in Chemical Formula 1 are all N, Ar1 and Ar2 are each independently phenyl; phenyl substituted with 5 deuterium atoms; biphenylyl; biphenylyl substituted with 5 deuterium atoms; carbazolyl; dibenzofuranyl; or dibenzothiophenyl, R1 is each independently hydrogen or deuterium, Ar3 is a substituent represented by Chemical Formula 1-1, p is an integer of 1 to 8, R 11 may each independently be hydrogen; deuterium; phenyl; or phenyl substituted with five deuteriums.

[0048] In one embodiment, X1 to X3 in Chemical Formula 1 are all N, Ar1 and Ar2 are each independently phenyl; phenyl substituted with 5 deuterium atoms; biphenylyl; biphenylyl substituted with 5 deuterium atoms; carbazolyl; dibenzofuranyl; or dibenzothiophenyl, R1 is each independently hydrogen or deuterium, Ar3 is a substituent represented by Chemical Formula 1-1, p is an integer of 1 to 8, R 11 may be deuterium or phenyl.

[0049] In one embodiment, X1 to X3 in Chemical Formula 1 are all N, Ar1 and Ar2 are each independently phenyl; phenyl substituted with 5 deuterium atoms; biphenylyl; biphenylyl substituted with 5 deuterium atoms; carbazolyl; dibenzofuranyl; or dibenzothiophenyl, R1 is each independently hydrogen or deuterium, Ar3 is a substituent represented by Chemical Formula 1-1, p is an integer of 6 to 8, R 11 may be deuterium.

[0050] In one embodiment, X1 to X3 in Formula 1 are all N, R1 is each independently hydrogen or deuterium, Ar3 is a substituent represented by Formula 1-2, q is an integer from 1 to 10, and R 12 are each independently hydrogen or deuterium, and Ar 12 may be phenyl.

[0051] In one embodiment, X1 to X3 in Chemical Formula 1 are all N, Ar1 and Ar2 are each independently phenyl; phenyl substituted with 5 deuterium atoms; biphenylyl; biphenylyl substituted with 5 deuterium atoms; carbazolyl; dibenzofuranyl; or dibenzothiophenyl, R1 is each independently hydrogen or deuterium, Ar3 is a substituent represented by Chemical Formula 1-2, q is an integer of 1 to 10, R 12 are each independently hydrogen or deuterium, and Ar 12 may be phenyl.

[0052] In one embodiment, X1 to X3 in Formula 1 are all N, R1 is each independently hydrogen or deuterium, Ar3 is a substituent represented by Formula 1-2-a, q is an integer from 1 to 10, and R 12 are each independently hydrogen or deuterium, and Ar 12 may be phenyl.

[0053] In one embodiment, X1 to X3 in Chemical Formula 1 are all N, Ar1 and Ar2 are each independently phenyl; phenyl substituted with 5 deuterium atoms; biphenylyl; biphenylyl substituted with 5 deuterium atoms; carbazolyl; dibenzofuranyl; or dibenzothiophenyl, R1 is each independently hydrogen or deuterium, Ar3 is a substituent represented by Chemical Formula 1-2-a, q is an integer of 1 to 10, R 12 are each independently hydrogen or deuterium, and Ar 12 may be phenyl.

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

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[0055] The compound represented by Chemical Formula 1 can be prepared, for example, by the following reaction scheme 1. [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.

[0056] The first step of the 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 varied according to those known in the art.

[0057] The second step of the above Reaction Scheme 1 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.

[0058] When the compound represented by Chemical Formula 1 contains deuterium, it can be prepared from a precursor containing deuterium, or it can be prepared from a precursor not containing deuterium, and then finally deuterium can be contained through a hydrogen / deuterium exchange reaction.

[0059] The method for preparing the compound represented by Formula 1 will be described in more detail in the Preparation Examples below.

[0060] The compound represented by the above formula 2 is characterized by having one or more deuterium atoms.

[0061] That is, in chemical formula 2, at least one of R'1 and R'2 is deuterium; at least one of R'1 and R'2 is deuterium and at least one substituent of Ar'1 and Ar'2 contains one or more deuterium; or, if neither R'1 nor R'2 is deuterium, at least one substituent of Ar'1 and Ar'2 can contain one or more deuterium.

[0062] Preferably, R'1 and R'2 are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl having 6 to 12 carbon atoms, wherein the aryl may be substituted with one or more deuterium atoms.

[0063] Preferably, R'1 and R'2 are each independently hydrogen; deuterium; phenyl; or phenyl substituted with 1 to 5 deuteriums.

[0064] Preferably, at least one of R'1 and R'2 is deuterium.

[0065] Preferably, n' and m' are each independently an integer of 5 to 7, or 6 to 7, and R'1 and R'2 are both deuterium.

[0066] Preferably, Ar'1 and Ar'2 are each independently phenyl which is unsubstituted or substituted with 1 to 5 deuteriums; biphenyl which is unsubstituted or substituted with 1 to 9 deuteriums; naphthyl which is unsubstituted or substituted with 1 to 7 deuteriums; dimethylfluorenyl which is unsubstituted or substituted with 1 to 13 deuteriums; dibenzofuranyl which is unsubstituted or substituted with 1 to 7 deuteriums; or dibenzothiophenyl which is unsubstituted or substituted with 1 to 7 deuteriums.

[0067] In one embodiment, n' and m' are each independently an integer from 6 to 7, R'1 and R'2 are both deuterium, and Ar'1 and Ar'2 are each independently an unsubstituted or substituted phenyl with 1 to 5 deuteriums; an unsubstituted or substituted biphenyl with 1 to 9 deuteriums; an unsubstituted or substituted naphthyl with 1 to 7 deuteriums; an unsubstituted or substituted dimethylfluorenyl with 1 to 13 deuteriums; an unsubstituted or substituted dibenzofuranyl with 1 to 7 deuteriums; or an unsubstituted or substituted dibenzothiophenyl with 1 to 7 deuteriums.

[0068] Preferably, the deuterium substitution rate of Chemical Formula 2 is 40 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 2 is 60% or more, 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.

[0069] Representative examples of the compound represented by Formula 2 are as follows: [ka] [ka] [ka] [ka] [ka]

[0070] 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.

[0071] The compound represented by Chemical Formula 2 can be prepared, for example, by the following reaction scheme 2. [Reaction Scheme 2] [ka]

[0072] In the above reaction scheme 2, the remainder except for X″ is as defined above, and X″ is a halogen, more preferably bromo or chloro.

[0073] The above reaction scheme 2 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the Suzuki coupling reaction can be varied according to those known in the art.

[0074] The compound represented by Chemical Formula 2 may be prepared from a precursor containing deuterium, or may be prepared from a precursor not containing deuterium and then finally contain deuterium through a hydrogen / deuterium exchange reaction.

[0075] The method for preparing the compound represented by the formula 2 will be described in more detail in the Preparation Examples below.

[0076] 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.

[0077] 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 may be included in the light-emitting layer as an organic compound. Alloy The organic alloy may be contained in the light-emitting layer. Alloy is the result of a pre-treatment of two or more single organic compounds, which may result in chemical interactions between the single organic compounds, such as, but not limited to, a thermal treatment process, such as heating and / or sublimation, followed by cooling.

[0078] The organic Alloy As mentioned above, since there is a chemical interaction between two or more single organic compounds, it has different properties from each single organic compound and a simple mixture in which there is no chemical interaction between the single organic compounds. Here, a simple mixture refers to a simple physical mixture of each single organic compound without any pretreatment. In other words, 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 of these, while a simple mixture of a first organic compound and a second organic compound exhibits the properties of the first organic compound, the second organic compound, or a combination of these. Alloy can exhibit properties that are distinct from the first organic compound, the second organic compound, or a simple mixture thereof.

[0079] For example, the organic Alloycan be different from the emission wavelengths of the first organic compound, the second organic compound, and simple mixtures thereof.

[0080] In addition, the organic Alloy The color of the first organic compound can be different from the color of the second organic compound, and from simple mixtures thereof.

[0081] In addition, the organic Alloy The glass transition temperature (Tg) of the first organic compound may be different from the glass transition temperature (Tg) of the second organic compound and the simple mixture thereof. Alloy The crystallization temperature (Tc) of the first organic compound may be different from the crystallization temperatures of the first organic compound, the second organic compound, and the simple mixture thereof. Alloy The melting temperature (Tm) of the first organic compound can be different from the melting temperatures of the first organic compound, the second organic compound, and simple mixtures thereof.

[0082] The organic Alloy 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. Alloy may be subjected to an additional step of physical grinding using a mixer or the like.

[0083] The organic Alloy As mentioned above, the result of pretreatment can be supplied using one source during thin film formation, which simplifies the process since there is no need for process control steps that are required when supplying two or more materials from separate sources.

[0084] In addition, the organic AlloySince the above-mentioned is a result obtained by the pretreatment, the uniformity and consistency of the deposited material can be ensured compared with the case where two or more single organic compounds are 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 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.

[0085] 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 available. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, chrysene, and periplanthene, which have 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 available, but are not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0086] 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.

[0087] 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.

[0088] Specific examples of the hole transport material include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0089] 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.

[0090] 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.

[0091] 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.

[0092] electron suppression layer The organic light-emitting device according to the present invention may optionally include an electron-blocking layer between the hole-transporting layer and the light-emitting layer.

[0093] 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.

[0094] 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. The electron transport layer 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 inhibits the transfer of holes from the light-emitting layer. The electron transport material is a material that can effectively receive electrons injected from the negative electrode and transfer them to the light-emitting layer, and is preferably a material that has high mobility for electrons.

[0095] 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.

[0096] 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.

[0097] The electron injection layer is a layer that injects electrons from an electrode, and is capable of transporting electrons, has an excellent electron injection effect from a negative electrode, an excellent electron injection effect for 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 is preferably a compound with excellent thin-film forming ability. Specific examples of the substance used in the electron injection layer include, but are not limited to, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preolenylidene methane, anthrone, etc., and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0098] 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.

[0099] Hole Blocking Layer The organic light-emitting device according to the present invention may optionally include a hole-blocking layer between the electron-transporting layer and the light-emitting layer.

[0100] The hole blocking layer prevents holes injected from the positive electrode from passing to the electron transport layer without being recombined in the light emitting layer, and the hole blocking layer is preferably made of a material having a large ionization energy.

[0101] 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.

[0102] 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 or 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 cathode, and the above-mentioned layers may be formed thereon, and a material to be used as an anode may be deposited thereon.

[0103] In addition to these methods, organic light-emitting devices can be fabricated by sequentially depositing the negative electrode material on a substrate through the positive electrode material in the reverse order of the above-mentioned configuration (WO2003 / 012890). Furthermore, the light-emitting layer may be formed by a solution coating method as well as a vacuum deposition method of the host and dopant. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc.

[0104] The organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided emission device, and may be a bottom emission device which is particularly required to have a relatively high light emitting efficiency.

[0105] 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 for illustrating the present invention, and the scope of the present invention is not limited thereto.

[0106] [Production Example 1: Production of Compound of Formula 1]

[0107] Preparation Example 1-1: Synthesis of Compound 1-1

[0108] Step 1) Synthesis of intermediate 1-1-1 [ka]

[0109] In a nitrogen atmosphere, 6-bromo-3-chlorodibenzo[b,d]furan (20g, 71mmol) and bis(pinacolato)diboron (18g, 71mmol) were added to 400ml of dioxane and stirred and refluxed. Then, anhydrous potassium acetate (20.9g, 213.1mmol) was added and thoroughly stirred, and palladium dibenzylideneacetone palladium (0.8g, 1.4mmol) and tricyclohexylphosphine (0.8g, 2.8mmol) were added. After reacting for 7 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 further dissolved in 233mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain intermediate 1-1-1 (15.2 g, 65%, MS: [M+H] + =329.6) was produced.

[0110] Step 2) Synthesis of intermediate 1-1-2 [ka]

[0111] In a nitrogen atmosphere, 1-1-1 (20g, 60.9mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-(phenyl-d5)-1,3,5-triazine (23.1g, 60.9mmol) were added to 400ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (25.2g, 182.6mmol) was dissolved in 75ml of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (2.1g, 1.8mmol) was added. After reacting for 2 hours, it was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 664mL of chloroform and 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 with chloroform and ethyl acetate to give a white solid compound 1-1-2 (24.5 g, 74%, MS: [M+H] + =546.1) was produced.

[0112] Step 3) Synthesis of compound 1-1 [ka]

[0113] In a nitrogen atmosphere, 1-1-2 (15 g, 27.5 mmol) and 9H-carbazole (4.6 g, 27.5 mmol) were added to 300 ml of toluene and stirred and refluxed. Then, sodium tertiary-butoxide (7.9 g, 82.6 mmol) was added and thoroughly stirred, and then bis(tritertiary-butylphosphine)palladium (0.4 g, 0.8 mmol) was added. After reacting for 2 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 further added to 185 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, and then sublimation purification was performed to obtain compound 1-1 (10 g, 54%, MS: [M+H] + =671.8) was produced.

[0114] Preparation Example 1-2: Synthesis of Compound 1-2

[0115] Step 1) Synthesis of intermediate 1-2-1 [ka]

[0116] In a nitrogen atmosphere, 6-bromo-3-chlorodibenzo[b,d]furan (15g, 53.3mmol) and 9H-carbazole-d8 (9.3g, 53.3mmol) were added to 300ml of toluene and stirred and refluxed. Then, sodium tertiary-butoxide (15.4g, 159.8mmol) was added and thoroughly stirred, and then bis(tritertiary-butylphosphine)palladium (0.8g, 1.6mmol) was added. After reacting for 3 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 further added to 200mL of chloroform and dissolved, washed twice with water, and 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 purified by silica gel column chromatography to obtain intermediate 1-2-1 (10.8g, 54%, MS: [M+H] + =376.9) was produced.

[0117] Step 2) Synthesis of intermediate 1-2-2 [ka]

[0118] In a nitrogen atmosphere, 1-2-1 (20 g, 53.2 mmol) and bis(pinacolato)diboron (13.5 g, 53.2 mmol) were added to 400 mL of dioxane and stirred and refluxed. Then, anhydrous potassium acetate (15.7 g, 159.6 mmol) was added and thoroughly stirred, and then palladium dibenzylideneacetone palladium (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.1 mmol) were added. After reacting for 3 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 further added to 249 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain intermediate 1-2-2 (18.4 g, 74%, MS: [M+H] + =468.4).

[0119] Step 3) Synthesis of Compound 1-2 [ka]

[0120] In a nitrogen atmosphere, 1-2-2 (20 g, 42.8 mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (14.7 g, 42.8 mmol) were added to 400 ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (17.7 g, 128.4 mmol) was dissolved in 54 ml of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 555 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, and then compound 1-2 (21.4 g, 77%, MS: [M+H] + =649.8).

[0121] Preparation Example 1-3: Synthesis of Compound 1-3 [ka]

[0122] Compound 1-3 was produced in the same manner as compound 1-1, except that in preparation example 1-1, 6-bromo-3-chlorodibenzo[b,d]furan was replaced with 1-bromo-7-chlorodibenzo[b,d]furan-2,3,4,6,8,9-d6, 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-(phenyl-d5)-1,3,5-triazine was replaced with 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine, and 9H-carbazole was replaced with 9H-carbazole-d8. (MS: [M+H] + =669.8)

[0123] Preparation Example 1-4: Synthesis of Compound 1-4 [ka]

[0124] Compound 1-4 was prepared in the same manner as compound 1-2, except that in preparation example 1-2, 6-bromo-3-chlorodibenzo[b,d]furan was replaced with 1-bromo-7-chlorodibenzo[b,d]furan-2,3,4,6,8,9-d6, 9H-carbazole-d8 was replaced with 9H-carbazole-, and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine was replaced with 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine. (MS: [M+H] + =661.8)

[0125] Preparation Example 1-5: Synthesis of Compound 1-5 [ka]

[0126] Compound 1-5 was produced in the same manner as compound 1-1, except that in preparation example 1-1, 6-bromo-3-chlorodibenzo[b,d]furan was replaced with 2-bromo-6-chlorodibenzo[b,d]furan, 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-(phenyl-d5)-1,3,5-triazine was replaced with 2-chloro-4,6-diphenyl-1,3,5-triazine, and 9H-carbazole was replaced with 2-(phenyl-d5)-9H-carbazole. (MS: [M+H] + =646.8)

[0127] Preparation Example 1-6: Synthesis of Compound 1-6 [ka]

[0128] Compound 1-6 was prepared in the same manner as compound 1-2, except that in preparation example 1-2, 6-bromo-3-chlorodibenzo[b,d]furan was replaced with 2-bromo-6-chlorodibenzo[b,d]furan and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine was replaced with 2-chloro-4,6-diphenyl-1,3,5-triazine. (MS: [M+H] + =573.7)

[0129] Preparation Example 1-7: Synthesis of Compound 1-7 [ka]

[0130] Compound 1-7 was produced in the same manner as compound 1-1, except that in preparation example 1-1, 6-bromo-3-chlorodibenzo[b,d]furan was replaced with 1-bromo-6-chlorodibenzo[b,d]furan, 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-(phenyl-d5)-1,3,5-triazine was replaced with 2-chloro-4,6-diphenyl-1,3,5-triazine, and 9H-carbazole was replaced with 4-phenyl-9H-carbazole-1,2,3,5,6,7,8-d7. (MS: [M+H] + =648.8)

[0131] Preparation Example 1-8: Synthesis of Compound 1-8 [ka]

[0132] Compound 1-8 was produced in the same manner as compound 1-2, except that in preparation example 1-2, 6-bromo-3-chlorodibenzo[b,d]furan was replaced with 1-bromo-6-chlorodibenzo[b,d]furan, 9H-carbazole-d8 was replaced with 9H-carbazole, and 2-([1,1'-biphenyl]-3-yl)-4-chloro-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] + =646.8)

[0133] Preparation Example 1-9: Synthesis of Compound 1-9 [ka]

[0134] Compound 1-9 was produced in the same manner as Compound 1-1, except that in Preparation Example 1-1, 6-bromo-3-chlorodibenzo[b,d]furan was replaced with 8-bromo-1-chlorodibenzo[b,d]furan, 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-(phenyl-d5)-1,3,5-triazine was replaced with 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine, and 9H-carbazole was replaced with 3-phenyl-9H-carbazole. (MS: [M+H] + =651.8)

[0135] Preparation Example 1-10: Synthesis of Compound 1-10 [ka]

[0136] Compound 1-10 was prepared in the same manner as compound 1-2, except that in preparation example 1-2, 6-bromo-3-chlorodibenzo[b,d]furan was replaced with 2-bromo-7-chlorodibenzo[b,d]furan and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine was replaced with 2-chloro-4,6-diphenyl-1,3,5-triazine. (MS: [M+H] + =573.7)

[0137] Preparation Example 1-11: Synthesis of Compound 1-11 [ka]

[0138] Compound 1-11 was produced in the same manner as in Compound 1-1, except that in Preparation Example 1-1, 6-bromo-3-chlorodibenzo[b,d]furan was replaced with 4-bromo-6-chlorodibenzo[b,d]thiophene, 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-(phenyl-d5)-1,3,5-triazine was replaced with 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-(phenyl-d5)-1,3,5-triazine, and 9H-carbazole was replaced with 4-phenyl-9H-carbazole-1,2,3,5,6,7,8-d7. (MS: [M+H] + =746.0)

[0139] Preparation Example 1-12: Synthesis of Compound 1-12 [ka]

[0140] Compound 1-12 was produced in the same manner as in Compound 1-1, except that in Preparation Example 1-1, 6-bromo-3-chlorodibenzo[b,d]furan was replaced with 6-bromo-1-chlorodibenzo[b,d]thiophene, 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-(phenyl-d5)-1,3,5-triazine was replaced with 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine, and 9H-carbazole was replaced with 9H-carbazole-1,2,3,4,5,6,7,8-d8. (MS: [M+H] + =665.9)

[0141] [Production Example 2: Production of Compound of Formula 2]

[0142] Preparation Example 2-1: Synthesis of Compound 2-1

[0143] Step 1) Synthesis of intermediate 2-1-1 [ka]

[0144] In a nitrogen atmosphere, 9-([1,1'-biphenyl]-4-yl)-3-bromo-9H-carbazole (20g, 50.4mmol) and (9-phenyl-9H-carbazol-3-yl)boronic acid (14.5g, 50.4mmol) were added to 400ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (20.9g, 151.1mmol) was dissolved in 63ml of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (1.7g, 1.5mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 565mL of chloroform and 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 with chloroform and ethyl acetate to give a white solid compound 2-1-1 (19.2 g, 68%, MS: [M+H] + =561.7) was produced.

[0145] Step 2) Synthesis of compound 2-1 [ka]

[0146] Compound 2-1-1 (10.0 g, 17.8 mmol), PtO2 (1.2 g, 5.4 mmol), and 89 ml of D2O were placed in a shaker tube, which was then sealed and heated at 250 °C and 600 psi for 12 hours. After the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with anhydrous magnesium sulfate, and the sample was purified by silica gel column chromatography, followed by sublimation purification to produce 3.9 g of compound 2-1 (yield 38%, MS: [M+H] + =579.8).

[0147] Preparation Example 2-2: Synthesis of Compound 2-2

[0148] Step 1) Synthesis of intermediate 2-2-1 [ka]

[0149] Compound 9-([1,1'-biphenyl]-4-yl)-3-bromo-9H-carbazole (20g, 50.4mmol) was added to 200ml of Benzen-D6 in a nitrogen atmosphere and stirred. Then, trifluoromethanesulfonic acid (3.8g, 25.1mmol) was added and heated and stirred. After reacting for 4 hours, it was cooled to room temperature, ethanol was added, and the resulting solid was filtered. The solid was dissolved in 886mL of chloroform and washed twice with water, and 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 purified through a silica column to obtain a white solid compound 2-2-1 (11.3g, 55%, MS: [M+H] + =409.4).

[0150] Step 2) Synthesis of compound 2-2 [ka]

[0151] In a nitrogen atmosphere, 2-2-1 (20 g, 49 mmol) and (9-([1,1'-biphenyl]-2-yl)-9H-carbazol-3-yl)boronic acid (17.8 g, 49 mmol) were added to 400 ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (20.3 g, 146.9 mmol) was dissolved in 60 ml of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.7 g, 1.5 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 634 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography and then purified by sublimation to obtain compound 2-2 (24.7 g, 78%, MS: [M+H] + =647.9).

[0152] Preparation Example 2-3: Synthesis of Compound 2-3

[0153] Step 1) Synthesis of intermediate 2-3-1 [ka]

[0154] In a nitrogen atmosphere, 9-([1,1'-biphenyl]-3-yl)-3-bromo-9H-carbazole (20g, 50.2mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (18.2g, 50.2mmol) were added to 400ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (20.8g, 150.6mmol) was dissolved in 21ml of water and added, and after stirring thoroughly, tetrakistriphenyl-phosphinopalladium (1.7g, 1.5mmol) was added. After reacting for 5 hours, it was cooled to room temperature and the generated solid was filtered. The solid was dissolved in 640mL of chloroform and 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 with chloroform and ethyl acetate to give a white solid compound 2-3-1 (24.3 g, 76%, MS: [M+H] + =637.8) was produced.

[0155] Step 2) Synthesis of Compound 2-3 [ka]

[0156] Compound 2-3-1 (10.0 g, 15.7 mmol), PtO2 (1.1 g, 4.8 mmol), and 89 ml of D2O were placed in a shaker tube, which was then sealed and heated at 250 °C and 600 psi for 12 hours. After the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with anhydrous magnesium sulfate, and the sample was purified by silica gel column chromatography, followed by sublimation purification to produce 5.7 g of compound 2-3 (yield 55%, MS: [M+H] + =657.9).

[0157] Preparation Example 2-4: Synthesis of Compound 2-4

[0158] Step 1) Synthesis of intermediate 2-4-1 [ka]

[0159] In a nitrogen atmosphere, 3-bromo-9H-carbazole (20g, 81.3mmol) and (9-phenyl-9H-carbazol-3-yl)boronic acid (23.3g, 81.3mmol) were added to 400ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (33.7g, 243.8mmol) was dissolved in 102ml of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (2.8g, 2.4mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 664mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain white solid compound 2-4-1 (21.6g, 65%, MS: [M+H] + =409.5).

[0160] Step 2) Synthesis of compound 2-4-2 [ka]

[0161] Compound 2-4-1 (10.0 g, 24.5 mmol), PtO2 (1.7 g, 7.5 mmol), and 139 ml of D2O were placed in a shaker tube, which was then sealed and heated at 250 °C and 600 psi for 12 hours. After the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried and concentrated with anhydrous magnesium sulfate, and the sample was purified by silica gel column chromatography, followed by sublimation purification to produce 5.2 g of compound 2-4-2 (yield 50%, MS: [M+H] + =422.6).

[0162] Step 3) Synthesis of Compounds 2-4 [ka]

[0163] In a nitrogen atmosphere, 2-4-2 (15 g, 35.6 mmol) and 2-chloro-9,9-dimethyl-9H-fluorene (8.1 g, 35.6 mmol) were added to 300 ml of toluene and stirred and refluxed. Then, sodium tertiary-butoxide (10.3 g, 106.7 mmol) was added and thoroughly stirred, and then bis(tritertiary-butylphosphine)palladium (0.5 g, 1.1 mmol) was added. After reacting for 1 hour, 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 added to 218 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The sample was concentrated and purified by silica gel column chromatography, and then sublimation purification was performed to obtain compound 2-4 (15.5 g, 71%, MS: [M+H] + =614.8) was produced.

[0164] Preparation Example 2-5: Synthesis of Compound 2-5

[0165] Step 1) Synthesis of Compounds 2-5 [ka]

[0166] In a nitrogen atmosphere, 2-4-2 (15 g, 35.6 mmol) and 2-bromodibenzo[b,d]furan (8.8 g, 35.6 mmol) were added to 300 ml of toluene and stirred and refluxed. Then, sodium tertiary-butoxide (10.3 g, 106.7 mmol) was added and thoroughly stirred, and then bis(tri-tertiary-butylphosphine)palladium (0.5 g, 1.1 mmol) was added. After reacting for 3 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 further added to 209 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The sample was concentrated and purified by silica gel column chromatography, and then sublimation purification was performed to obtain compound 2-5 (16.5 g, 79%, MS: [M+H] + =588.8).

[0167] [Production example 3: Organic Alloy Manufacturing

[0168] Production example 3-1: Organic Alloy Manufacturing 1 Compound 1-1 and compound 2-1 were mixed in a weight ratio of 40:60 and placed in a vacuum chamber for 10 -2 The two mixtures were dissolved by increasing the temperature under a pressure of less than Torr, and then cooled to room temperature after 1 hour to obtain a solid product. The product was then crushed in a mixer to obtain a powdered organic compound. Alloy I got 1.

[0169] Production Examples 3-2 to 3-18, and Production Examples 3-A to 3-D Except for the changes in the mixed materials as shown in Table 1 below, Alloy Using the same manufacturing method as 1, Alloy 2~Organic Alloy 18, and organic Alloy A~Organic Alloy Compounds H-1, H-2 and H-3 in Table 1 below are as follows. [ka]

[0170] [Table 1]

[0171] [Example]

[0172] Example 1: Fabrication of an organic light-emitting device A glass substrate coated with a 1400 Å-thick thin film of ITO (Indium Tin Oxide) was placed in distilled water containing detergent 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 washed for 30 minutes, and then ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning was completed, ultrasonic cleaning was performed with solvents of isopropyl alcohol, acetone, and methanol, and the substrate was 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.

[0173] On the ITO transparent electrode thus prepared, 95% by weight of HT-A and 5% by weight of PD were thermally vacuum deposited to a thickness of 100 Å to form a hole injection layer, and then only the HT-A material was deposited to a thickness of 1150 Å to form a hole transport layer, on which the following HT-B was thermally vacuum deposited to a thickness of 450 Å as an electron inhibiting layer.

[0174] Then, the organic layer prepared in Preparation Example 3-1 was formed on the electron inhibiting layer to a thickness of 350 Å. Alloy The light-emitting layer was formed by vacuum deposition of 1 and the dopant compound GD in a weight ratio of 92:8.

[0175] Next, ET-A was vacuum-deposited to a thickness of 50 Å for the hole blocking layer, ET-B and Liq were thermally vacuum-deposited to a thickness of 300 Å for the electron transport layer in a ratio of 1:1, and then Yb (ytterbium) was vacuum-deposited to a thickness of 10 Å for the electron injection layer.

[0176] Magnesium and silver were deposited on the electron injection layer in a ratio of 1:4 to a thickness of 150 Å to form a negative electrode, thereby completing an organic light emitting device. [ka]

[0177] 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.

[0178] Examples 2 to 22 and Comparative Examples 1-1 to 2-4 Organic light emitting devices of Examples 2 to 22 and Comparative Examples 1-1 to 2-4 were fabricated using the same method as in Example 1, except that the host material was changed as shown in Table 2. In Examples 19 to 22 and Comparative Examples 2-1 to 2-4, a simple mixture of two compounds was used as the host.

[0179] [Experimental Example] The organic light emitting devices manufactured in Examples 1 to 22 and Comparative Examples 1-1 to 2-4 were heat treated in an oven at 120° C. for 30 minutes, and then removed from the oven. A current was applied to measure the voltage, efficiency, and lifespan (T95). The results are shown in Table 2 below. At this time, the voltage and efficiency were measured at 10 mA / 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%.

[0180] [Table 2] JPEG0007646987000101.jpg81146

[0181] Referring to Table 2, it can be seen that when the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 are used as a host in the light-emitting layer of an organic light-emitting device, they have low voltage and high efficiency characteristics and are excellent in life characteristics, compared to the compounds used in the Comparative Examples. In addition, the organic light-emitting device manufactured using the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 has low voltage and high efficiency characteristics and is excellent in life characteristics, compared to the compounds used in the Comparative Examples. Alloy During use, it can be seen that the efficiency and life span are further increased compared to when the compounds of Chemical Formula 1 and Chemical Formula 2 are simply mixed. [Explanation of symbols]

[0182] 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 an organic alloy of a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2: [Chemical formula 1] 【Chemistry 99】 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 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 at least one selected from the group consisting of N, O, and S, 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; Ar ３ is a substituent represented by the following chemical formula 1-1 or 1-2, [Chemical formula 1-1] 【Chemistry 100】 [Chemical formula 1-2] 【Chemistry 101】 In the above Chemical Formulas 1-1 and 1-2, p is an integer from 1 to 8; q is an integer from 1 to 10; R １１ and R １２ 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; A is a benzene ring fused to two adjacent pentagonal rings; Ar １２ is a substituted or unsubstituted aryl having 6 to 60 carbon atoms; [Chemical formula 2] 【Chemistry 102】 In the above Chemical Formula 2, n' and m' are each independently an integer from 1 to 7; R' １ and R' ２ 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; Ar' 1 and Ar' 2 are each independently phenyl which is unsubstituted or substituted with 1 to 5 deuteriums; biphenyl which is unsubstituted or substituted with 1 to 9 deuteriums; naphthyl which is unsubstituted or substituted with 1 to 7 deuteriums; or dimethylfluorenyl which is unsubstituted or substituted with 1 to 13 deuteriums; However, R' １ and R' ２ At least one of Ar' is deuterium; and / or Ar' １ and Ar' ２ At least one of is substituted with one or more deuterium atoms.

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

3. Ar １ and Ar ２ 2. The organic light-emitting device of claim 1, wherein each independently is phenyl; phenyl substituted with five deuteriums; biphenylyl; biphenylyl substituted with five deuteriums; carbazolyl; dibenzofuranyl; or dibenzothiophenyl.

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

5. R １１ 2. The organic light-emitting device of claim 1, wherein each independently is hydrogen; deuterium; phenyl; or phenyl substituted with five deuteriums.

6. The organic light-emitting device according to claim 1, wherein the chemical formula 1-2 is represented by the following chemical formula 1-2-a: [Chemical formula 1-2-a] 【Chemistry 103】 In the above chemical formula 1-2-a, q, R １２ , and Ar １２ is as defined in claim 1.

7. R １２ are each independently hydrogen or deuterium; Ar １２ The organic light-emitting device of claim 1 , wherein is phenyl.

8. R equal to or greater than 1 １ is deuterium; and / or Ar １ ~Ar ３ The organic light-emitting device according to claim 1 , wherein at least one of

9. Ar ３ is a substituent represented by the above chemical formula 1-1, p is an integer from 4 to 8; R １１ The organic light-emitting device of claim 1 , wherein is deuterium.

10. 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 104】 【Chemistry 105】 【Chemistry 106】 【Chemistry 107】 【Chemistry 108】 【Chemistry 109】 【Chemistry 110】 【Chemistry 111】 【Chemistry 112】 【Chemistry 113】 【Chemistry 114】 【Chemistry 115】 【Chemistry 116】 【Chemistry 117】 【Chemistry 118】 【Chemistry 119】 【Chemistry 120】 【Chemistry 121】 【Chemistry 122】 【Chemistry 123】 【Chemical 124】 【Chemistry 125】 【Chemistry 126】 【Chemistry 127】 【Chemistry 128】 【Chemistry 129】 【Chemistry 130】 【Chemistry 131】 【Chemistry 132】 【Chemistry 133】 【Chemistry 134】 【Chemistry 135】 【Chemistry 136】 【Chemistry 137】 【Chemistry 138】 【Chemistry 139】 【Chemistry 140】 【Chemistry 141】 【Chemistry 142】 【Chemistry 143】 【Chemistry 144】 【Chemistry 145】 【Chemistry 146】 【Chemistry 147】 【Chemistry 148】 【Chemistry 149】 【Chemistry 150】 【Chemistry 151】 【Chemistry 152】 【Chemistry 153】 【Chemistry 154】 【Chemistry 155】 。

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

12. n' and m' are each independently an integer from 6 to 7; R' １ and R' ２ The organic light-emitting device according to claim 1 , wherein each of

13. 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 156】 【Chemistry 157】 【Chemistry 160】 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.

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