Organic light-emitting devices

Abstract

The present invention provides an organic light emitting device.

Description

[Technical Field]

[0001] [CROSS-REFERENCE TO RELATED APPLICATIONS] This application claims the benefit of priority based on Korean Patent Application No. 10-2021-0026796, filed February 26, 2021, and Korean Patent Application No. 10-2022-0023070, filed February 22, 2022, and all contents disclosed in the documents of said Korean patent applications are incorporated herein by reference.

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

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

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

[0005] There is a continuing demand for the development of new organic materials for use in 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 provides an organic light emitting device. [Means for solving the problem]

[0008] The present invention provides A positive electrode and a negative electrode provided opposite the positive electrode; a light-emitting layer provided between the positive electrode and the negative electrode, The light-emitting layer includes a first compound represented by the following Chemical Formula 1 and a second compound represented by the following Chemical Formula 2: [Chemical formula 1] [ka] In the above Chemical Formula 1, A is a substituted or unsubstituted carbazolyl; L1 is a single bond or a substituted or unsubstituted arylene having 6 to 60 carbon atoms; X1, X2, and X3 are each independently N or CH, provided that at least one selected from the group consisting of X1, X2, and X3 is N; Ar1 and Ar2 each independently represent a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms and containing one or more heteroatoms selected from the group consisting of N, O, and S; [Chemical formula 2] [ka] In the above Chemical Formula 2, B is a benzene ring fused with two adjacent five-membered rings, L'1 and L'2 each independently represent a single bond or a substituted or unsubstituted arylene having 6 to 60 carbon atoms; Ar'1 and Ar'2 each independently represent a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms and containing one or more heteroatoms selected from the group consisting of N, O, and S; R'1, R'2, and R'3 are each independently hydrogen, deuterium, a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms and containing one or more heteroatoms selected from the group consisting of N, O, and S; a is an integer from 0 to 4, b is an integer from 0 to 2, c is an integer of 0 to 4. [Effects of the Invention]

[0009] The organic light emitting device described above includes two host compounds in the light emitting layer, which can improve the efficiency, driving voltage and / or life characteristics of the organic light emitting device. [Brief explanation of the drawings]

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

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

[0012] In this specification, [ka] or [ka] denotes a bond that is connected to another substituent, D denotes deuterium, and Ph denotes a phenyl group.

[0013] As used herein, the term "substituted or unsubstituted" refers to a group selected from the group consisting of deuterium, halogen, nitrile, nitro, hydroxy, carbonyl, ester, imide, amino, phosphine oxide, alkoxy, aryloxy, alkylthioxy, arylthioxy, alkylsulfoxy, arylsulfoxy, silyl, boron, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, aralkenyl, alkylaryl, alkylamine, aralkylamine, heteroarylamine, arylamine, arylphosphine, or a heterocyclic group containing one or more N, O, and S atoms, or a group in which two or more of the above-listed substituents are linked together. For example, a "substituent linked to two or more substituents" may be a biphenyl group. That is, a biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are linked together.

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

[0015] In this specification, the oxygen of the ester group may be substituted with a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a compound having the following structural formula, but is not limited to these. [ka]

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

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

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

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

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

[0021] In this specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but preferably ranges from 2 to 40. According to one embodiment, the number of carbon atoms in the alkenyl group is from 2 to 20. According to yet another embodiment, the number of carbon atoms in the alkenyl group is from 2 to 10. According to yet another embodiment, the number of carbon atoms in the alkenyl group is from 2 to 6. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, and a styrenyl group, but are not limited to these.

[0022] In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to yet 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, cyclooctyl, and adamantyl, but are not limited to these.

[0023] In this specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be, 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 this specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted, [ka] However, the present invention is not limited to these.

[0025] In this specification, heteroaryl refers to a heterocyclic group containing one or more heteroatoms selected from O, N, Si, and S as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably 2 to 60. Examples of heteroaryl groups include, but are not limited to, thiophene, furanyl, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuranyl.

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

[0027] As used herein, the term "deuterated or deuterium-substituted" means that at least one available hydrogen atom in each chemical formula is substituted with deuterium (D). Specifically, in each chemical formula or substituent definition, "deuterium-substituted" means that at least one or more positions capable of intramolecular hydrogen bonding are substituted with deuterium, more specifically, that at least 10% of available hydrogen atoms are substituted with deuterium. For example, each chemical formula may be at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, or 100% deuterated.

[0028] Meanwhile, an organic light emitting device according to one embodiment includes a positive electrode, a negative electrode facing the positive electrode, and an emitting layer between the positive electrode and the negative electrode, wherein the emitting layer includes a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2, and the first compound represented by Chemical Formula 1 and the second compound represented by Chemical Formula 2 are used as host materials of the emitting layer.

[0029] The organic light emitting device according to the present invention contains two compounds having specific structures as host materials in the light emitting layer, and can improve the efficiency, driving voltage and / or life characteristics of the organic light emitting device.

[0030] The present invention will be described in detail below for each component.

[0031] Positive and negative electrodes The cathode material preferably has a high work function to facilitate hole injection into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SNO:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0032] The negative electrode material is preferably a material with a small work function so as to facilitate electron injection into the organic layer. Specific examples of the negative electrode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO / Al.

[0033] hole injection layer The organic light-emitting device according to the present invention may optionally include a hole injection layer between the anode and a hole transport layer described below.

[0034] The hole injection layer is located on the cathode and injects holes from the cathode. It contains a hole injection material. The hole injection material preferably has the ability to transport holes, has excellent hole injection effects from the cathode, and has excellent hole injection effects for the light-emitting layer or light-emitting material. It also preferably prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material. It is also preferable that the HOMO (highest occupied molecular orbital) of the hole injection material be between the work function of the cathode material and the HOMO of the surrounding organic layer.

[0035] Specific examples of the hole injection material 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.

[0036] hole transport layer The organic light-emitting device according to the present invention may include a hole transport layer between the anode and the light-emitting layer. The hole transport layer receives holes from the anode or a hole injection layer formed on the anode and transports them to the light-emitting layer, and includes a hole transport material. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and is preferably a material with high hole mobility. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0037] electron blocking layer The organic light emitting device according to the present invention may optionally include an electron blocking layer between the hole transport layer and the light emitting layer. The electron blocking layer is formed on the hole transport layer, preferably in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by controlling hole mobility and preventing excessive electron movement, thereby increasing the hole-electron binding probability. The electron blocking layer includes an electron blocking material, and examples of such electron blocking materials include, but are not limited to, arylamine-based organic compounds.

[0038] Light-emitting layer The organic light-emitting device according to the present invention includes an emissive layer between an anode and an anode, the emissive layer including the first compound and the second compound as host compounds. Specifically, the combination of the first compound and the second compound can maintain an appropriate hole-to-electron ratio in the emissive layer. In particular, when the first compound and the second compound are used simultaneously, holes and electrons are smoothly transferred to the dopant, improving the efficiency and lifetime of the device. As a result, the device can exhibit lower voltage and longer lifetime characteristics than devices using only one of the first compound or the second compound, or a combination of the first compound and the second compound with other compounds.

[0039] The first compound and the second compound will be described below in order.

[0040] (1st compound) The first compound is represented by the following Chemical Formula 1. Specifically, the first compound is a compound containing carbazolyl and triazine-based (pyridine, pyrimidine) substituents on triphenylenyl, and the compound has excellent electron transport ability as a host material, and can be used in combination with the second compound described below to increase the probability of recombination of holes and electrons in the light-emitting layer. [Chemical formula 1] [ka]

[0041] In the above Chemical Formula 1, A is a substituted or unsubstituted carbazolyl; L1 is a single bond or a substituted or unsubstituted arylene having 6 to 60 carbon atoms; X1, X2, and X3 are each independently N or CH, provided that at least one selected from the group consisting of X1, X2, and 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 and containing one or more heteroatoms selected from the group consisting of N, O, and S.

[0042] Meanwhile, in the above Chemical Formula 1, the carbon represented by * means that only hydrogen is substituted, and the carbon does not contain any additional substituents.

[0043] The second compound is represented by the following Chemical Formula 1-1 or Chemical Formula 1-2 depending on the substitution position of A: [Chemical formula 1-1] [ka] [Chemical formula 1-2] [ka] In the above Chemical Formula 1-1 or Chemical Formula 1-2, L1, X1, X2, X3, Ar1, and Ar2 are as defined above; R1's each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 60 carbon atoms, 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 one or more heteroatoms selected from the group consisting of N, O, and S; R2 is a substituted or unsubstituted alkyl having 1 to 60 carbon atoms or a substituted or unsubstituted aryl having 6 to 60 carbon atoms; R3 each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 60 carbon atoms, a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl having 5 to 60 carbon atoms and containing one or more heteroatoms selected from the group consisting of N, O, and S; m is an integer from 0 to 8, n is an integer from 0 to 7.

[0044] In this case, m, which means the number of R1, is 0, 1, 2, 3, 4, 5, 6, 7, or 8, and n, which means the number of R3, is 0, 1, 2, 3, 4, 5, 6, or 7.

[0045] Preferably, L1 is a single bond, phenylene or biphenylylene, wherein said phenylene and biphenylylene may each independently be substituted or unsubstituted with one or more deuterium atoms.

[0046] Preferably, Ar1 and Ar2 are each independently phenyl, biphenylyl, terphenylyl, dimethylfluorenyl, naphthyl, phenanthrenyl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, 9-phenyl-9H-carbazolyl, benzoxazolyl, benzothiazolyl, 2-phenylbenzoxazolyl, or 2-phenylbenzothiazolyl, each of which may be independently substituted or unsubstituted with one or more deuterium atoms.

[0047] Preferably, each R1 is independently hydrogen, deuterium, phenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl, wherein the phenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl may each independently be substituted or unsubstituted with one or more deuterium atoms.

[0048] Preferably, each R2 can be independently phenyl unsubstituted or substituted with one or more deuterium atoms.

[0049] Preferably, each R3 is independently hydrogen, deuterium, phenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl, wherein the phenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl may be unsubstituted or substituted with one or more deuterium atoms.

[0050] Representative examples of the first compound represented by Chemical Formula 1 are as follows: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] .

[0051] Meanwhile, the first compound can be prepared, for example, by the following reaction scheme 1. [Reaction Scheme 1-A] [ka] [Reaction Scheme 1-B] [ka]

[0052] In the reaction schemes 1-A and 1-B, each X is independently a halogen, preferably bromine or chlorine, and the other substituents are as defined above.

[0053] Specifically, the compound represented by Chemical Formula 1 is prepared by Suzuki coupling reaction and amine substitution reaction, which are preferably carried out in the presence of a palladium catalyst and a base, respectively. The reactive groups for the reactions can be appropriately changed, and the preparation method for the compound represented by Chemical Formula 1 is further exemplified in the Preparation Examples described below.

[0054] (Second Compound) The second compound is represented by the following Chemical Formula 2. Specifically, the second compound is an indolocarbazole compound, which serves as a host compound and a dopant material and has excellent hole transporting ability, and can be used in combination with the above-mentioned first compound to increase the recombination probability of holes and electrons in the light-emitting layer. [Chemical formula 2] [ka]

[0055] In the above Chemical Formula 2, B is a benzene ring fused with two adjacent five-membered rings, L'1 and L'2 each independently represent a single bond or a substituted or unsubstituted arylene having 6 to 60 carbon atoms; Ar'1 and Ar'2 each independently represent a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms and containing one or more heteroatoms selected from the group consisting of N, O, and S; R'1, R'2, and R'3 are each independently hydrogen, deuterium, a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms and containing one or more heteroatoms selected from the group consisting of N, O, and S; a is an integer from 0 to 4, b is an integer from 0 to 2, c is an integer of 0 to 4. The second compound is represented by any one of the following chemical formulas 2-1 to 2-5 depending on the condensation position of B: [Chemical formula 2-1] [ka] [Chemical formula 2-2] [ka] [Chemical formula 2-3] [ka] [Chemical formula 2-4] [ka] [Chemical formula 2-5] [ka] In the chemical formulas 2-1 to 2-5, L'1, L'2, Ar'1, Ar'2, R'1, R'2, R'3, a, b and c are as defined above.

[0056] Preferably, L'1 and L'2 are each independently a single bond, phenylene or biphenylylene, each of which may be independently substituted or unsubstituted with one or more deuterium atoms.

[0057] Preferably, Ar'1 and Ar'2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl, and Ar'1 and Ar'2 may each independently be substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, alkyl having 1 to 10 carbon atoms, and aryl having 6 to 20 carbon atoms.

[0058] Preferably, R'1, R'2 and R'3 are each independently hydrogen, deuterium, phenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl, wherein the phenyl, dibenzofuranyl, carbazol-9-yl, and 9-phenyl-9H-carbazolyl may each independently be substituted or unsubstituted with one or more deuterium atoms.

[0059] In this case, a representing the number of R'1 is 0, 1, 2, 3 or 4, b representing the number of R'2 is 0, 1 or 2, and c representing the number of R'3 is 0, 1, 2, 3 or 4.

[0060] Representative examples of the second compound represented by Chemical Formula 2 are as follows: [ka] [ka] [ka] [ka]

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[0061] Meanwhile, the second compound can be prepared, for example, by the following reaction scheme 2.

[0062] [Reaction Scheme 2] [ka]

[0063] In the above reaction scheme 2, each X is independently a halogen, preferably bromine or chlorine, and the other substituents are as defined above.

[0064] Specifically, the compound represented by Chemical Formula 2 is prepared by combining starting materials SM'1 and SM'2 through an amine substitution reaction. The amine substitution reaction is preferably carried out in the presence of a palladium catalyst and a base. The reactive groups for the amine substitution reaction may be appropriately changed, and the method for preparing the compound represented by Chemical Formula 2 is further exemplified in the Preparation Examples below.

[0065] The first compound and the second compound are contained in the light-emitting layer in a weight ratio of 1:9 to 9:1. If the second compound is contained in the light-emitting layer in an amount too small compared to the first compound, electron transport within the light-emitting layer is hindered, resulting in an imbalance between holes and electrons throughout the device, resulting in problems with the voltage, efficiency, and lifespan of the fabricated device. If the second compound is contained in an amount too large, the lifespan may be reduced. For example, the weight ratio of the first compound to the second compound in the light-emitting layer may be 2:8 to 8:2, 3:7 to 7:3, 4:6 to 6:4, or 4:6 to 5:5.

[0066] Meanwhile, the light-emitting layer may further include a dopant in addition to the two host materials. Examples of such dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include fused aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periflanthene. Styrylamine compounds include substituted or unsubstituted arylamines substituted with at least one arylvinyl group, and may be substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamino groups. Specific examples include, but are not limited to, styrylamines, styryldiamines, styryltriamines, and styryltetraamines. Metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0067] In this case, the dopant material is contained in the light-emitting layer in an amount of 1 to 25 wt % based on the total weight of the host material and the dopant material.

[0068] hole-blocking layer The organic light-emitting device according to the present invention may optionally include a hole-blocking layer between the light-emitting layer and the electron-transporting layer (described later). The hole-blocking layer is formed on the light-emitting layer, preferably in contact with the light-emitting layer, and serves to improve the efficiency of the organic light-emitting device by controlling electron mobility and preventing excessive hole migration, thereby increasing the hole-electron coupling probability. The hole-blocking layer includes a hole-blocking material. Examples of such hole-blocking materials include, but are not limited to, compounds having an electron-withdrawing group introduced therein, such as azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; and phosphine oxide derivatives.

[0069] electron transport layer The electron transport layer is formed between the light-emitting layer and the anode and serves to receive electrons from the electron injection layer and transport them to the light-emitting layer. The electron transport layer includes an electron transport material, and the electron transport material is preferably a material that can efficiently receive electrons injected from the anode and transfer them to the light-emitting layer, and has high electron mobility.

[0070] Specific examples of electron injection and transport materials include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavone-metal complexes, triazine derivatives, etc. Alternatively, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthrone, etc., and their derivatives, metal complex compounds, or nitrogen-containing five-membered ring derivatives can be used in combination with these, but are not limited to these.

[0071] electron injection layer The organic light-emitting device according to the present invention may include an electron injection layer between the electron transport layer and the negative electrode, if necessary.

[0072] The electron injection layer is located between the electron transport layer and the negative electrode and serves to inject electrons from the negative electrode. The electron injection layer includes an electron injection material, and the electron injection material preferably has the ability to transport electrons, has an excellent electron injection effect on the light-emitting layer or light-emitting material, and is excellent in thin film formation ability.

[0073] Specific examples of the electron injection material include, but are not limited to, LiF, NaCl, CsF, LiO, BaO, 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.

[0074] Examples of the metal complex compounds include, but are not limited to, 8-hydroxyquinolinatolithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholate)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtholate)gallium.

[0075] Organic light-emitting devices The structure of an organic light-emitting device according to the present invention is shown in Figures 1 and 2. Figure 1 shows an example of an organic light-emitting device comprising a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. In this structure, the first compound and the second compound can be contained in the light-emitting layer.

[0076] 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, an electron blocking layer 7, an emitting layer 3, a hole blocking layer 8, an electron transport and injection layer 9, and a negative electrode 4. In this structure, the first compound and the second compound can be contained in the emitting layer.

[0077] The organic light emitting device according to the present invention can be fabricated by sequentially stacking the above-described components. Here, a metal, conductive metal oxide, or alloy thereof can be deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a cathode, and then the above-described layers can be formed thereon, followed by deposition of a material to be used as an anode. Alternatively, an organic light emitting device can be fabricated by sequentially depositing an anode material, an organic material layer, and a cathode material on a substrate. The light emitting layer can be formed by vacuum deposition of a host and a dopant, or by solution coating. Solution coating methods include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, and roll coating.

[0078] In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate (WO 2003 / 012890), but the manufacturing method is not limited to this.

[0079] Meanwhile, the organic light emitting device according to the present invention may be a top-emitting type, a back-emitting type, or a double-sided emitting type depending on the materials used.

[0080] Hereinafter, the preparation of an organic light-emitting device including the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 will be described in detail with reference to Examples. However, the following Examples are merely illustrative of the present invention, and the scope of the present invention is not limited thereto.

[0081] [Synthesis example] Synthesis Example 1: Synthesis of Compound 1-1 [ka]

[0082] Step 1) Synthesis of Compound 1-1-a Under a nitrogen atmosphere, 4-bromo-chloro-2-iodoaniline (50 g, 150.4 mmol) and [1,1'-biphenyl]-2-ylboronic acid (29.8 g, 150.4 mmol) were added to 1000 mL of tetrahydrofuran and stirred under reflux. Sodium carbonate (47.8 g, 451.3 mmol) dissolved in 48 mL of water was then added and thoroughly stirred. Tetrakistriphenylphosphinopalladium (5.2 g, 4.5 mmol) was then added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This mixture was then dissolved in 1079 mL of 20x chloroform and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, and the mixture was stirred. The filtrate was then distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and hexane to give brown solid compound 1-1-a (43.2 g, 80%, MS: [M+H] + =359.7) was produced.

[0083] Step 2) Synthesis of Compound 1-1-b Compound 1-1-a (40 g, 111.5 mmol) was added to hydrochloric acid (2 M, 700 mL) and stirred at 0°C for approximately 15 minutes. Sodium nitrite (8.5 g, 122.6 mmol) was then slowly added. After 1 hour, the mixture was heated at 60°C for 3 hours and cooled to room temperature. The organic and aqueous layers were separated and the organic layer was distilled. This was then dissolved in 800 mL of 20x chloroform and washed twice with aqueous sodium bicarbonate. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and hexane to give dark brown solid compound 1-1-b (27.4 g, 72%, MS: [M+H] + =342.0) was produced.

[0084] Step 3) Synthesis of Compound 1-1-c Under a nitrogen atmosphere, 1-1-b (25 g, 73.3 mmol) and bis(pinacolurato)diboron (18.6 g, 73.3 mmol) were added to 500 mL of 1,4-dioxane and stirred under reflux. Potassium phosphate (46.7 g, 219.9 mmol) was then added and thoroughly stirred. Palladium dibenzylideneacetone palladium (1.3 g, 2.2 mmol) and tricyclohexylphosphine (1.2 g, 4.4 mmol) were then added. After reacting for 3 hours, the mixture was cooled to room temperature and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. The mixture was dissolved in 285 mL of 10x chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to give brown solid compound 1-1-c (22.8 g, 80%, MS: [M+H] + =389.7) was produced.

[0085] Step 4) Synthesis of Compound 1-1-d In a nitrogen atmosphere, 1-1-c (20 g, 51.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (13.8 g, 51.5 mmol) were added to 400 mL of tetrahydrofuran and stirred under reflux. Then, sodium carbonate (16.4 g, 154.4 mmol) dissolved in 16 mL of water was added and thoroughly stirred, followed by the addition of tetrakistriphenylphosphinopalladium (1.8 g, 1.5 mmol). After reacting for 1 hour, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved again in 554 mL of 20x chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain yellow solid compound 1-1-d (19.1 g, 69%, MS: [M+H] + =494.8) was produced.

[0086] Step 5) Synthesis of Compound 1-1 In a nitrogen atmosphere, 1-1-d (30 g, 55.7 mmol) and 9H-carbazole (9.3 g, 55.7 mmol) were added to 600 mL of xylene and stirred under reflux. Then, sodium tert-butoxide (16.1 g, 167.1 mmol) was added and thoroughly stirred, followed by the addition of bis(tri-tert-butylphosphine)palladium (0.9 g, 1.7 mmol). After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. This was dissolved again in 351 mL of 10x chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified using a silica column with chloroform and ethyl acetate to obtain a yellow solid, compound 1-1 (19 g, 54%, MS: [M+H] + =625.7) was produced.

[0087] Synthesis Example 2: Synthesis of Compound 1-2 [ka]

[0088] Compound 1-2 (MS: [M+H]) was prepared in the same manner as in Synthesis Example 1, except that 9H-carbazole was replaced with 9H-carbazole-1,3,4,5,6,8-d6. + =631.8) was produced.

[0089] Synthesis Example 3: Synthesis of Compound 1-3 [ka]

[0090] Compound 1-3 (MS [M+H]) was prepared in the same manner as in Synthesis Example 1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine and 9H-carbazole were replaced with 2-chloro-4,6-bis(phenyl-d5-1,3,5-triazine) and 9H-carbazole-1,2,3,4,5,6,7,8-d8, respectively.+ =643.8) was produced.

[0091] Synthesis Example 4: Synthesis of Compound 1-4 [ka]

[0092] Compound 1-4 (MS [M+H]) was prepared in the same manner as in Synthesis Example 1 for Compound 1-1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was replaced with 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. + =701.8) was produced.

[0093] Synthesis Example 5: Synthesis of Compound 1-5 [ka]

[0094] Compound 1-5 (MS [M+H]) was prepared in the same manner as in Synthesis Example 1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine and 9H-carbazole-1,3,4,5,6,8-d6 were used instead of 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine and 9H-carbazole-1,3,4,5,6,8-d6, respectively. + =663.2) was produced.

[0095] Synthesis Example 6: Synthesis of Compound 1-6 [ka]

[0096] Compound 1-6 (MS [M+H]) was prepared in the same manner as in Synthesis Example 1 for Compound 1-1, except that 9H-carbazole was replaced with 4-(dibenzo[b,d]thiophen-4-yl)-9H-carbazole. + =807.8) was produced.

[0097] Synthesis Example 7: Synthesis of Compound 1-7 [ka]

[0098] Compound 1-7 (MS [M+H]) was prepared in the same manner as in Synthesis Example 1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was replaced with 2-chloro-4,6-diphenylpyrimidine. + =624.7) was produced.

[0099] Synthesis Example 8: Synthesis of Compound 1-8 [ka]

[0100] Under a nitrogen atmosphere, 1-1-d (30 g, 60.7 mmol) and (9-(phenyl-d5)-9H-carbazol-3-yl-1,2,4,5,6,7,8-d7)boronic acid (18.2 g, 60.7 mmol) were added to 600 mL of 1,4-dioxane and stirred under reflux. Then, tripotassium phosphate (38.7 g, 182.2 mmol) dissolved in 39 mL of water was added and stirred thoroughly. Then, dibenzylideneacetone palladium (1 g, 1.8 mmol) and tricyclohexylphosphine (1 g, 3.6 mmol) were added. After 9 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1299 mL of 30x chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give a yellow solid compound 1-8 (28.1 g, 65%, MS: [M+H] + =713.9) was produced.

[0101] Synthesis Example 9: Synthesis of Compound 1-9 [ka]

[0102] Compound 1-9 (MS [M+H]) was prepared in the same manner as in Synthesis Examples 1 and 8, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine. + =804.2) was manufactured.

[0103] Synthesis Example 10: Synthesis of Compound 1-10 [ka]

[0104] Compound 1-10 (MS [M+H]) was prepared in the same manner as in Synthesis Example 1, except that 9H-carbazole was replaced with 4-(phenyl-d5)-9H-carbazole-1,2,3,5,6,7,8-d7. + =713.9) was produced.

[0105] Synthesis Example 11: Synthesis of Compound 2-1 [ka]

[0106] Step 1) Synthesis of Compound 2-1-a Under a nitrogen atmosphere, 5,8-dihydroindolo[2,3-c]carbazole (30 g, 117 mmol) and 4-bromo-1,1'-biphenyl (27.3 g, 117 mmol) were added to 600 mL of xylene and stirred under reflux. Sodium tert-butoxide (33.8 g, 351.1 mmol) was then added and thoroughly stirred, followed by the addition of bis(tri-tert-butylphosphine)palladium (1.8 g, 3.5 mmol). After reacting for 2 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. This was dissolved again in 478 mL of 10x toluene and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified using a silica column with toluene and ethyl acetate to obtain a white solid compound 2-1-a (31.6 g, 66%, MS: [M+H] + =409.5) was produced.

[0107] Step 2) Synthesis of Compound 2-1 In a nitrogen atmosphere, 2-1-a (30 g, 73.4 mmol) and 3-bromo-1,1'-biphenyl (17.1 g, 73.4 mmol) were added to 600 mL of xylene and stirred under reflux. Sodium tert-butoxide (21.2 g, 220.3 mmol) was then added and thoroughly stirred, followed by the addition of bis(tri-tert-butylphosphine)palladium (1.1 g, 2.2 mmol). After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. This was dissolved again in 412 mL of 10x toluene and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified using a silica column with toluene and ethyl acetate to obtain a white solid compound 2-1 (31.3 g, 76%, MS: [M+H] + =561.7) was produced.

[0108] Synthesis Example 12: Synthesis of Compound 2-2 [ka]

[0109] Compound 2-2 (MS [M+H]) was prepared in the same manner as in the preparation of Compound 2-1, except that in Synthesis Example 11, 5,8-dihydroindolo[2,3-c]carbazole, 4-bromo-1,1′-biphenyl, and 3-bromo-1,1′-biphenyl were used instead of 5,8-dihydroindolo[2,3-c]carbazole-1,2,3,4,6,7,9,10,11,12-d10, 4-bromo-1,1′-biphenyl-2,3′,4′-d3, and 3-bromo-1,1′-biphenyl-2,4′,6-d3, respectively. + =577.8) was produced.

[0110] Synthesis Example 13: Synthesis of Compound 2-3 [ka]

[0111] Compound 2-3 (MS [M+H]) was prepared in the same manner as in the preparation of Compound 2-1, except that 3-bromo-1,1'-biphenyl was replaced with 3-bromo-1,1'-biphenyl-2,2',3',4',5,5',6,6'-d8 in Synthesis Example 11. + =582.8) was produced.

[0112] Synthesis Example 14: Synthesis of Compound 2-4 [ka]

[0113] Compound 2-4 (MS [M+H]) was prepared in the same manner as in Synthesis Example 11, except that 3-bromo-1,1'-biphenyl was replaced with 4-bromo-1,1'-biphenyl. + =561.7) was produced.

[0114] Synthesis Example 15: Synthesis of Compound 2-5 [ka]

[0115] Compound 2-5 (MS [M+H]) was prepared in the same manner as in the preparation of Compound 2-1, except that in Synthesis Example 11, 5,8-dihydroindolo[2,3-c]carbazole-1,2,4,6,7,9,11,12-d8 and 4-bromo-1,1'-biphenyl-2',3,4',5,6'-d5 were used instead of 5,8-dihydroindolo[2,3-c]carbazole, 4-bromo-1,1'-biphenyl, and 3-bromo-1,1'-biphenyl, respectively. + =579.8) was produced.

[0116] Synthesis Example 16: Synthesis of Compound 2-6 [ka]

[0117] Compound 2-6 (MS [M+H]) was prepared in the same manner as in the preparation of Compound 2-1, except that in Synthesis Example 11, 5,8-dihydroindolo[2,3-c]carbazole, 4-bromo-1,1′-biphenyl, and 3-bromo-1,1′-biphenyl were used instead of 5,8-dihydroindolo[2,3-c]carbazole-1,2,3,4,6,7,9,10,11,12-d10, 3-bromo-1,1′-biphenyl-4′,6-d2, and 3-bromo-1,1′-biphenyl-2′,4,4′,6,6′-d5, respectively. + =578.8) was produced.

[0118] Synthesis Example 17: Synthesis of Compound 2-7 [ka]

[0119] Compound 2-7 (MS [M+H]) was prepared in the same manner as in the preparation of Compound 2-1, except that in Synthesis Example 11, 5,8-dihydroindolo[2,3-c]carbazole and 3-bromo-1,1′-biphenyl were replaced with 5,8-dihydroindolo[2,3-c]carbazole-1,2,3,4,6,7,9,10,11,12-d10 and 5′-bromo-1,1′:3′,1″-terphenyl, respectively. + =647.8) was produced.

[0120] Synthesis Example 18: Synthesis of Compound 2-8 [ka]

[0121] Compound 2-8 (MS [M+H]) was prepared in the same manner as in Synthesis Example 11, except that 5,8-dihydroindolo[2,3-c]carbazole, 4-bromo-1,1′-biphenyl, and 3-bromo-1,1′-biphenyl were replaced with 5,7-dihydroindolo[2,3-b]carbazole, bromobenzene, and 4-bromodibenzo[b,d]thiophene, respectively. + =515.6) was produced.

[0122] Synthesis Example 19: Synthesis of Compound 2-9 [ka]

[0123] Compound 2-9 (MS [M+H]) was prepared in the same manner as in Synthesis Example 11, except that 5,8-dihydroindolo[2,3-c]carbazole, 4-bromo-1,1′-biphenyl, and 3-bromo-1,1′-biphenyl were replaced with 5,7-dihydroindolo[2,3-b]carbazole, bromobenzene, and 4-bromodibenzo[b,d]furan, respectively. + =499.6) was produced.

[0124] Synthesis Example 20: Synthesis of Compound 2-10 [ka]

[0125] Compound 2-10 (MS [M+H]) was prepared in the same manner as in Synthesis Example 11, except that 5,8-dihydroindolo[2,3-c]carbazole, 4-bromo-1,1′-biphenyl, and 3-bromo-1,1′-biphenyl were replaced with 5,12-dihydroindolo[3,2-a]carbazole and 4-bromo-1,1′-biphenyl, respectively. + =561.7) was produced.

[0126] [Example] Example 1 A glass substrate coated with a 1,400Å thick ITO (indium tin oxide) thin film was placed in distilled water with detergent and ultrasonically cleaned. The detergent used was a product of Fischer Co., and the distilled water was filtered through a Millipore Co. filter. After cleaning the ITO for 30 minutes, it was ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning, it was ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned using oxygen plasma for 5 minutes and then transferred to a vacuum deposition machine.

[0127] On the ITO transparent electrode thus prepared, a hole injection layer was formed by thermal vacuum deposition of the following HT-A compound and the following PD compound in a weight ratio of 95:5 to a thickness of 100 Å, and then a hole transport layer was formed by thermal vacuum deposition of the following HT-A compound alone to a thickness of 1150 Å. On the hole transport layer, an electron blocking layer (electron inhibiting layer) was formed by thermal vacuum deposition of the following HT-B compound to a thickness of 450 Å.

[0128] On the electron blocking layer, the host compounds, Compound 1-1 and Compound 2-1, prepared above, and the dopant compound, GD, were vacuum-deposited in a weight ratio of 85:15 to form a 400 Å thick light-emitting layer, where the weight ratio of Compound 1-1 to Compound 2-1 was 1:1.

[0129] On the light-emitting layer, the following ET-A compound was vacuum-deposited to a thickness of 50 Å to form a hole-blocking layer. On the hole-blocking layer, the following ET-B compound and the following Liq compound were thermally vacuum-deposited to a thickness of 250 Å in a weight ratio of 2:1, and then LiF and magnesium were vacuum-deposited to a thickness of 30 Å in a weight ratio of 1:1 to form an electron-transporting and injection layer. On the electron-transporting and injection layer, magnesium and silver were vacuum-deposited to a thickness of 160 Å in a weight ratio of 1:4 to form an anode, thereby completing the fabrication of an organic light-emitting device. [ka]

[0130] During the above process, the deposition rate of the organic material was maintained at 0.4-0.7 Å / sec, the deposition rate of lithium fluoride on the negative electrode was maintained at 0.3 Å / sec, and the deposition rates of silver and magnesium were maintained at 2 Å / sec. The vacuum level during deposition was 2×10 -7 ~5×10 -6 The organic light-emitting device was fabricated under a constant pressure of torr.

[0131] Examples 2 to 10 An organic light emitting device was manufactured in the same manner as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound 1-1 and Compound 2-1.

[0132] The structures of the first and second compounds used in the examples are as follows: [ka] [ka] [ka]

[0133] Comparative Examples 1 to 9 An organic light emitting device was manufactured in the same manner as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound 1-1 and Compound 2-1.

[0134] In this case, in Table 1 below, compounds H-2 and C1 to C3 are as follows. [ka]

[0135] Experimental Example A current was applied to the organic light emitting devices prepared in the Examples and Comparative Examples to measure the voltage, efficiency, and lifespan (T95). The results are shown in Table 1 below. At this time, the voltage and efficiency were 10 mA / cm 2 The measurement was performed by applying a current density of 20 mA / cm. In addition, T95 in Table 1 below is the value at a current density of 20 mA / cm. 2 This means the time it takes for the initial brightness to decrease to 95%.

[0136] [Table 1] JPEG0007721860000084.jpg38170

[0137] As shown in Table 1 above, the organic light-emitting devices of Examples in which both the first compound and the second compound of the present invention were used as hosts exhibited superior properties in terms of efficiency and lifespan compared to the organic light-emitting devices of Comparative Examples 1 to 3 in which only the first compound was used and the organic light-emitting devices of Comparative Examples 4 and 7 in which neither the first compound nor the second compound was used.

[0138] In addition, the organic light-emitting device of the present example used two types of hosts, and it was found that it exhibited higher efficiency and superior lifespan than the organic light-emitting devices of Comparative Examples 8 and 9, which used other host combinations instead of the combination of Compound 1 and Compound 2.

[0139] Considering that the luminous efficiency and lifespan characteristics of organic light-emitting devices generally have a trade-off relationship, this means that the organic light-emitting device employing the compound of the present invention exhibits significantly improved device characteristics compared to the comparative example device. [Explanation of symbols]

[0140] 1 board 2 Positive electrode 3. Light-emitting layer 4 Negative electrode 5. Hole injection layer 6. Hole transport layer 7 Electron blocking layer 8. Hole-blocking layer 9. Electron transport and injection layers

Claims

1. A positive electrode and a negative electrode provided opposite the positive electrode; a light-emitting layer provided between the positive electrode and the negative electrode, The light-emitting layer includes a first compound represented by the following Chemical Formula 1 and a second compound represented by the following Chemical Formula 2: [Chemical formula 1] 【Chemical 1】 In the above Chemical Formula 1, A is a substituted or unsubstituted carbazolyl; L １ is a single bond, phenylene or biphenylylene, the phenylene and biphenylylene are each independently unsubstituted or substituted with one or more deuterium atoms; X １ , X ２ and X ３ are each independently N or CH, provided that X １ , X ２ and X ３ one or more selected from the group consisting of is N; Ar １ and Ar ２ are each independently phenyl, biphenylyl, terphenylyl, dimethylfluorenyl, naphthyl, phenanthrenyl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, 9-phenyl-9H-carbazolyl, benzoxazolyl, benzothiazolyl, 2-phenylbenzoxazolyl, or 2-phenylbenzothiazolyl; each independently substituted or unsubstituted with one or more deuterium atoms; [Chemical formula 2] 【Chemistry 2】 In the above Chemical Formula 2, B is a benzene ring fused with two adjacent 5-membered rings, L' １ and L' ２ each independently represents a single bond, phenylene, or biphenylylene; the phenylene or biphenylylene is each independently unsubstituted or substituted with one or more deuterium atoms; Ar' １ and Ar' ２ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl; The Ar′ １ and Ar' ２ are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, alkyl having 1 to 10 carbon atoms, and aryl having 6 to 20 carbon atoms; R' １ , R' ２ and R' ３ are each independently hydrogen or deuterium, a is an integer from 0 to 4, b is an integer from 0 to 2; c is an integer of 0 to 4.

2. The organic light-emitting device according to claim 1, wherein the first compound is represented by the following Chemical Formula 1-1 or Chemical Formula 1-2: [Chemical formula 1-1] 【Chemistry 3】 [Chemical formula 1-2] 【Chemistry 4】 In the above Chemical Formula 1-1 or Chemical Formula 1-2, L １ , X １ , X ２ , X ３ , Ar １ , and Ar ２ is as defined in claim 1, R １ each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 60 carbon atoms, 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 one or more heteroatoms selected from the group consisting of N, O, and S; R ２ is a substituted or unsubstituted alkyl having 1 to 60 carbon atoms or a substituted or unsubstituted aryl having 6 to 60 carbon atoms, R ３ each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 60 carbon atoms, a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl having 5 to 60 carbon atoms and containing one or more heteroatoms selected from the group consisting of N, O, and S; m is an integer from 0 to 8; n is an integer from 0 to 7.

3. R １ are each independently hydrogen, deuterium, phenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl; The organic light-emitting device of claim 2 , wherein the phenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl are each independently substituted or unsubstituted with one or more deuterium atoms.

4. R ２ The organic light-emitting device of claim 2 , wherein is phenyl unsubstituted or substituted with one or more deuterium atoms.

5. R ３ are each independently hydrogen, deuterium, phenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl; The organic light-emitting device according to claim 2 or 4, wherein the phenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl are each independently substituted or unsubstituted with one or more deuterium atoms.

6. 2. The organic light-emitting device according to claim 1, wherein the first compound is any one selected from the group consisting of: 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 。

7. The organic light-emitting device according to claim 1, wherein the second compound is represented by any one of the following chemical formulas 2-1 to 2-5: [Chemical formula 2-1] 【Chemical 21】 [Chemical formula 2-2] 【Chemical 22】 [Chemical formula 2-3] 【Chemical 23】 [Chemical formula 2-4] 【Chemistry 24】 [Chemical formula 2-5] 【Chemistry 25】 In the chemical formulas 2-1 to 2-5, L' １ , L' ２ , Ar' １ , Ar' ２ , R' １ , R' ２ , R' ３ , a, b and c are as defined in claim 1.

8. 2. The organic light-emitting device according to claim 1, wherein the second compound is any one selected from the group consisting of: 【Chemical 26】 【Chemical 27】 【Chemical Formula 28】 【Chemical 29】 【Chemistry 30】 【Chemical 31】 ​ 【Chemical 33】 【Chemical 34】 【Chemistry 35】 【Chemical 36】 【Chemical 37】 【Chemical 38】 【Chemical Formula 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemical 44】 【Chemistry 45】 【Chemistry 46】 。

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