Organic light-emitting device

Abstract

The present specification provides an organic light-emitting device including a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2.

Description

[Technical field]

[0001] The present application relates to organic light emitting devices. This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0093438, filed with the Korean Intellectual Property Office on July 27, 2022, the entire contents of which are incorporated herein by reference. [Background technology]

[0002] In general, organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon usually has a structure including a positive electrode, a negative electrode, and an organic material layer between them. Here, the organic material layer is often a multi-layer structure composed of different materials to improve the efficiency and safety of the organic light emitting device, and may be composed of, 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 material layer, and the injected holes and electrons are combined to form excitons, and when the excitons fall to a floor state, light is generated.

[0003] There is a continuing demand for the development of new materials for such organic light emitting devices. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Korean Patent Publication No. 10-2017-0036641 Summary of the Invention [Problem to be solved by the invention]

[0005] The present application aims to provide an organic light-emitting device. [Means for solving the problem]

[0006] One embodiment of the present invention provides an organic light-emitting device comprising: an anode; a cathode; and a first organic layer and a second organic layer disposed between the anode and the cathode, the first organic layer comprising a compound represented by Chemical Formula 1 below, and the second organic layer comprising a compound represented by Chemical Formula 2 below:

[0007] [ka] In the above Chemical Formula 1, Ar1 and Ar2 are the same or different and each independently represents hydrogen; deuterium; or a substituted or unsubstituted aryl group; L1 and L2 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted arylene group; X1 to X3 are the same or different and each independently represents N or CR; At least one of X1 to X3 is N; Ra, Rb and R are the same or different and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; a is an integer of 0 to 6, and when a is 2 or more, 2 or more Ra are the same or different, b is an integer of 0 to 8, and when b is 2 or more, two or more Rb's are the same or different, [ka] In the above Chemical Formula 2, R1 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; m is an integer of 0 to 9, and when m is 2 or more, two or more R1's are the same or different, D is deuterium and n is an integer from 0 to 8; R2 to R6 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a group represented by the following formula A: At least one of R2 and R6 is represented by the following chemical formula A: [ka] In the above chemical formula A, R7 to R11 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring; The dotted line (---) indicates the site of connection to Chemical Formula 2. Effect of the Invention

[0008] The organic light-emitting device described in this specification exhibits the effects of low driving voltage, high efficiency, and / or long life by including a compound represented by Chemical Formula 1 in the first organic layer and a compound represented by Chemical Formula 2 in the second organic layer. [Brief description of the drawings]

[0009] [Figure 1] An example of an organic light-emitting element in which a substrate 1, an anode 2, a second organic layer 22, a first organic layer 21, and a cathode 10 are laminated in this order is shown. [Diagram 2] An example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10 are laminated in this order is shown. [Diagram 3] An example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 11, and a cathode 10 are laminated in this order is shown. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] The present invention will be described in further detail below.

[0011] In this specification, when a part "comprises" a certain component, this means that it may further include other components, not excluding other components, unless specifically stated to the contrary.

[0012] In this specification, when a member is said to be "located on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member is present between the two members.

[0013] As used herein, "dotted lines (---)" refer to points of attachment to a chemical formula or compound.

[0014] In the present specification, the deuterium substitution rate of a compound is calculated based on the maximum value of the molecular weight distribution at the end of the reaction using TLC-MS (Thin-Layer Chromatography / Mass Spectrometry) or a quantitative analysis method using NMR, adding DMF as an internal standard, 1 The D-substitution rate can be determined by calculating the total peak integration amount using the integration ratio on H NMR.

[0015] In this specification, the term "energy level" refers to the magnitude of energy. Therefore, the energy level is interpreted as meaning the absolute value of the energy value. For example, a low or deep energy level means that the absolute value is larger in the negative direction from the vacuum level.

[0016] In this specification, HOMO (highest occupied molecular orbital) refers to the molecular orbital function (highest occupied molecular orbital) in the highest energy region where electrons can participate in bonds, LUMO (lowest unoccupied molecular orbital) refers to the molecular orbital function (lowest unoccupied molecular orbital) in the lowest energy region where electrons can participate in half-bonding regions, and HOMO energy level refers to the distance from the vacuum level to the HOMO. Also, LUMO energy level refers to the distance from the vacuum level to the LUMO.

[0017] In this specification, the term "bandgap" refers to the energy level difference between HOMO and LUMO, that is, the HOMO-LUMO gap.

[0018] In this specification, the HOMO energy level can be measured using an atmospheric photoelectron spectrometer (AC3, manufactured by RIKEN KEIKI Co., Ltd.), and the LUMO energy level can be calculated from the wavelength value measured by photoluminescence (PL).

[0019] In this specification, examples of the substituents will be described below, but the present invention is not limited to these.

[0020] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of the substitution is not limited to the position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0021] In this specification, the term "substituted or unsubstituted" means that the group is substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; an alkyl group; a cycloalkyl group; an aryl group; and a heterocycle, or that the group is substituted with a substituent in which two or more of the above-listed substituents are linked, or that the group has no substituents.

[0022] In this specification, the term "substituted or unsubstituted" means that it is substituted with one or more substituents selected from the group consisting of an alkyl group, an aryl group, and a heterocycle, or that it is substituted with a substituent in which two or more of the substituents exemplified above are linked, or that it has no substituents.

[0023] Examples of the substituents are described below, but are not limited thereto.

[0024] In the present invention, examples of halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).

[0025] In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an n-pentyl group, a hexyl group, an n-hexyl group, a heptyl group, an n-heptyl group, an octyl group, and an n-octyl group.

[0026] In the present invention, 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 another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0027] In the present invention, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl or polycyclic aryl. According to one embodiment, the aryl has 6 to 30 carbon atoms. According to one embodiment, the aryl has 6 to 20 carbon atoms. Examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and a quaterphenyl group. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and a triperylenyl group.

[0028] In the present invention, the fluorenyl group may be substituted, and two of the substituents may be bonded to each other to form a spiro structure.

[0029] When the fluorenyl group is substituted, [ka] Spirofluorenyl groups such as [ka] (9,9-dimethylfluorenyl group), and [ka] (9,9-diphenylfluorenyl group), but is not limited thereto.

[0030] In the present invention, the heterocyclic group is a heterocyclic group containing one or more of N, O, P, S, Si and Se as a hetero element, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of the heterocyclic group include, but are not limited to, a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, and a triazinyl group.

[0031] In this specification, the heteroaryl group may be the same as the heterocyclic group described above, except that the heteroaryl group is aromatic.

[0032] In this specification, the arylene group may be the same as the above-mentioned explanation of the aryl group, except that the arylene group is a divalent group. Examples of the arylene group include a phenylene group, a naphthylene group, a biphenylene group, a fluorenylene group, a phenanthrylene group, a terphenylene group, an anthracenylene group, and a pyrenylene group.

[0033] In this specification, the above-mentioned explanation regarding the heterocyclic group may be applied to the divalent heterocyclic group, except that the heterocyclic group is a divalent group.

[0034] In this specification, the above description of the aryl group may be applied to the n+1 valent aryl group, except that the aryl group has a valence of n+1.

[0035] In this specification, the above description of the heterocyclic group may be applied to the n+1 valent heterocyclic group, except that the heterocyclic group has a valence of n+1.

[0036] As used herein, the term "ring" refers to a substituted or unsubstituted ring formed by bonding adjacent groups together, and may be a hydrocarbon ring or a heterocyclic ring.

[0037] The hydrocarbon ring may be aromatic, aliphatic or a fused aromatic and aliphatic ring, and may be selected from the above-listed cycloalkyl or aryl groups.

[0038] In this specification, the term "forming a ring by bonding with adjacent groups" means forming a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a condensed ring thereof by bonding with adjacent groups. The hydrocarbon ring means a ring consisting of only carbon and hydrogen atoms. The heterocycle means a ring containing one or more selected from N, O, P, S, Si, and Se. In this specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle may be monocyclic or polycyclic.

[0039] In this specification, the term "aliphatic hydrocarbon ring" refers to a non-aromatic ring that is composed only of carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.

[0040] In this specification, aromatic hydrocarbon ring means an aromatic ring consisting of only carbon and hydrogen atoms.Examples of aromatic hydrocarbon ring include, but are not limited to, benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, etc. In this specification, aromatic hydrocarbon ring may be interpreted as having the same meaning as aryl group.

[0041] In this specification, the term "aliphatic heterocycle" refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocane, and thiocane.

[0042] As used herein, aromatic heterocycle means an aromatic ring that contains one or more heteroatoms. Examples of aromatic heterocycles include, but are not limited to, pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxine, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, diazanaphthalene, triazindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, phenanthridine, indolocarbazole, and indenocarbazole.

[0043] DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described in detail below with reference to preferred embodiments thereof. However, the present invention may be modified in various ways, and the scope of the present invention is not limited to the embodiments described below.

[0044] The organic light-emitting device of the present invention is characterized by containing both the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2, and exhibits the effects of low voltage, high efficiency, and / or long life.

[0045] Chemical formula 1 will be described in detail below.

[0046] [ka]

[0047] In the above Chemical Formula 1, Ar1 and Ar2 are the same or different and each independently represents hydrogen; deuterium; or a substituted or unsubstituted aryl group; L1 and L2 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted arylene group; X1 to X3 are the same or different and each independently represents N or CR; At least one of X1 to X3 is N; Ra, Rb and R are the same or different and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; a is an integer of 0 to 6, and when a is 2 or more, 2 or more Ra are the same or different, b is an integer of 0 to 8, and when b is 2 or more, two or more Rbs are the same or different.

[0048] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represents hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0049] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represents hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0050] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represents hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0051] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently is hydrogen; deuterium; or an aryl group unsubstituted or substituted with deuterium.

[0052] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represents hydrogen; deuterium; or an aryl group having 6 to 60 carbon atoms which is unsubstituted or substituted with deuterium.

[0053] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represents hydrogen; deuterium; or an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with deuterium.

[0054] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represents hydrogen; deuterium; or an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with deuterium.

[0055] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently a substituted or unsubstituted aryl group.

[0056] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0057] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0058] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0059] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; or a substituted or unsubstituted fluorenyl group.

[0060] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; or a substituted or unsubstituted naphthyl group.

[0061] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0062] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represent a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; or a deuterium-substituted or unsubstituted naphthyl group.

[0063] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthryl group; or a substituted or unsubstituted fluorenyl group, and at least one of Ar1 and Ar2 is a substituted or unsubstituted phenyl group.

[0064] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group, and at least one of Ar1 and Ar2 is a substituted or unsubstituted phenyl group.

[0065] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represent a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; a deuterium-substituted or unsubstituted terphenyl group; a deuterium-substituted or unsubstituted naphthyl group; a deuterium-substituted or unsubstituted phenanthryl group; or a deuterium-substituted or unsubstituted fluorenyl group, and at least one of Ar1 and Ar2 is a deuterium-substituted or unsubstituted phenyl group.

[0066] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represent a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; or a deuterium-substituted or unsubstituted naphthyl group, and at least one of Ar1 and Ar2 is a deuterium-substituted or unsubstituted phenyl group.

[0067] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represent a phenyl group; a biphenyl group; or a naphthyl group, and at least one of Ar1 and Ar2 is a phenyl group.

[0068] In one embodiment of the present invention, L1 and L2 are the same or different and each independently a direct bond; or a substituted or unsubstituted arylene group.

[0069] In one embodiment of the present invention, L1 and L2 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

[0070] In one embodiment of the present invention, L1 and L2 are the same or different and each independently represents a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0071] In one embodiment of the present invention, L1 and L2 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0072] In one embodiment of the present invention, L1 and L2 are the same or different and each independently represent a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group.

[0073] In one embodiment of the present invention, L1 and L2 are the same or different and each independently represent a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0074] In one embodiment of the present invention, L1 and L2 are the same or different and each independently represent a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0075] In one embodiment of the present invention, L1 and L2 are the same or different and each independently represent a direct bond; a deuterium-substituted or unsubstituted phenylene group; or a deuterium-substituted or unsubstituted biphenylene group.

[0076] In one embodiment of the present invention, L1 and L2 are the same or different and each independently is a direct bond; a phenylene group; or a biphenylene group.

[0077] In one embodiment of the invention, L1 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group.

[0078] In one embodiment of the invention, L1 is a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0079] In one embodiment of the present invention, L1 is a direct bond; a deuterium-substituted or unsubstituted phenylene group; a deuterium-substituted or unsubstituted biphenylene group; a deuterium-substituted or unsubstituted terphenylene group; or a deuterium-substituted or unsubstituted naphthylene group.

[0080] In one embodiment of the present invention, L1 is a deuterium-substituted or unsubstituted phenylene group; or a deuterium-substituted or unsubstituted biphenylene group.

[0081] In one embodiment of the invention, L1 is a phenylene group; or a biphenylene group.

[0082] In one embodiment of the invention, L2 is a direct bond; or a substituted or unsubstituted phenylene group.

[0083] In one embodiment of the invention, L2 is a substituted or unsubstituted phenylene group.

[0084] In one embodiment of the invention, L2 is a direct bond; or a deuterium-substituted or unsubstituted phenylene group.

[0085] In one embodiment of the invention, L2 is a deuterium-substituted or unsubstituted phenylene group.

[0086] In one embodiment of the invention, L2 is a phenylene group.

[0087] In one embodiment of the present invention, at least one of X1 to X3 is N.

[0088] In one embodiment of the present invention, one of X1 to X3 is N.

[0089] In one embodiment of the present specification, two of X1 to X3 are N.

[0090] In one embodiment of the present invention, X1 to X3 are N.

[0091] In one embodiment of the invention, X1 is N, and X2 and X3 are CR.

[0092] In one embodiment of the invention, X2 is N, and X1 and X3 are CR.

[0093] In one embodiment of the invention, X3 is N, and X1 and X2 are CR.

[0094] In one embodiment of the invention, X1 and X2 are N and X3 is CR.

[0095] In one embodiment of the invention, X1 and X3 are N and X2 is CR.

[0096] In one embodiment of the invention, X2 and X3 are N and X1 is CR.

[0097] In one embodiment of the present invention, Ra, Rb and R are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0098] In one embodiment of the present invention, Ra, Rb and R are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0099] In one embodiment of the present invention, Ra, Rb and R are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0100] In one embodiment of the present invention, Ra, Rb and R are the same or different and are each independently hydrogen; deuterium; a deuterium-substituted or unsubstituted alkyl group; or a deuterium-substituted or unsubstituted aryl group.

[0101] In one embodiment of the present invention, Ra, Rb and R are the same or different and each independently represents hydrogen; deuterium; an alkyl group having 1 to 60 carbon atoms which is substituted or unsubstituted with deuterium; or an aryl group having 6 to 60 carbon atoms which is substituted or unsubstituted with deuterium.

[0102] In one embodiment of the present invention, Ra, Rb and R are the same or different and each independently represents hydrogen; deuterium; an alkyl group having 1 to 30 carbon atoms which is substituted or unsubstituted with deuterium; or an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium.

[0103] In one embodiment of the present invention, Ra, Rb and R are the same or different and each independently represents hydrogen; deuterium; an alkyl group having 1 to 20 carbon atoms which is substituted or unsubstituted with deuterium; or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium.

[0104] In one embodiment of the present invention, Ra, Rb and R are the same or different and each independently represents hydrogen; deuterium; an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with deuterium; or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium.

[0105] In one embodiment of the present invention, Ra, Rb and R are the same or different from each other and are each independently hydrogen; or deuterium.

[0106] In one embodiment of the invention, Ra, Rb and R are all hydrogen. In one embodiment of the invention, Ra, Rb and R are all deuterium.

[0107] In one embodiment of the present invention, a is an integer of 0 to 6, and when a is 2 or more, 2 or more Ra are the same or different from each other. In one embodiment of the present invention, a is an integer of 0-6. In one embodiment of the present invention, a is an integer of 1-6. In one embodiment of the invention, a is 6. In one embodiment of the invention, a is 5. In one embodiment of the invention, a is 4. In one embodiment of the invention, a is 3. In one embodiment of the invention, a is 2. In one embodiment of the invention, a is 1. In one embodiment of the invention, a is 0.

[0108] In one embodiment of the present specification, b is an integer of 0 to 8, and when b is 2 or more, two or more Rb's are the same or different from each other. In one embodiment of the present invention, b is an integer of 0-8. In one embodiment of the present invention, b is an integer of 1-8. In one embodiment of the invention, b is 8. In one embodiment of the invention, b is 7. In one embodiment of the invention, b is 6. In one embodiment of the invention, b is 5. In one embodiment of the invention, b is 4. In one embodiment of the invention, b is 3. In one embodiment of the invention, b is 2. In one embodiment of the invention, b is 1. In one embodiment of the invention, b is 0.

[0109] In one embodiment of the present invention, the above-mentioned Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.

[0110] [ka] [ka]

[0111] In the above Chemical Formulas 1-1 to 1-4, The definitions of Ar1, Ar2, L1, L2, X1 to X3, Ra, Rb, a, and b are the same as those in Chemical Formula 1.

[0112] In one embodiment of the present specification, the above-mentioned Chemical Formula 1 is represented by any one of the following Chemical Formulae 1-A to 1-D.

[0113] [ka] [ka]

[0114] In the above Chemical Formula 1-A to Chemical Formula 1-D, The definitions of Ar1, Ar2, L1, L2, X1 to X3, Ra, Rb, a, and b are the same as those in Chemical Formula 1.

[0115] In one embodiment of the present specification, the above-mentioned Chemical Formula 1 is represented by the following Chemical Formula 1-1-1.

[0116] [ka]

[0117] In the above Chemical Formula 1-1-1, The definitions of Ar1, Ar2, L1, L2, X1 to X3, Ra, Rb, a, and b are the same as those in Chemical Formula 1.

[0118] In one embodiment of the present invention, the compound represented by Chemical Formula 1 is at least 40% substituted with deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 is 50% or more substituted with deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 is 60% or more substituted with deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 is 70% or more substituted with deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 is 80% or more substituted with deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 is 90% or more substituted with deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 is 100% substituted with deuterium.

[0119] In one embodiment of the present invention, the compound represented by Chemical Formula 1 contains 40% to 60% deuterium. In another embodiment, the compound represented by Chemical Formula 1 contains 40% to 80% deuterium. In another embodiment, the compound represented by Chemical Formula 1 contains 60% to 80% deuterium. In another embodiment, the compound represented by Chemical Formula 1 contains 80% to 100% deuterium.

[0120] In one embodiment of the present invention, the above-mentioned Chemical Formula 1 is represented by any one of the following compounds:

[0121] [ka]

[0122] [ka]

[0123] [ka]

[0124] [ka]

[0125] Chemical formula 2 will be described in detail below. [ka]

[0126] In the above Chemical Formula 2, R1 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; m is an integer of 0 to 9, and when m is 2 or more, two or more R1's are the same or different, D is deuterium and n is an integer from 0 to 8; R2 to R6 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a group represented by the following formula A: At least one of R2 and R6 is represented by the following chemical formula A: [ka] In the above chemical formula A, R7 to R11 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring; The dotted line (---) indicates the site of connection to Chemical Formula 2.

[0127] In one embodiment of the present invention, R1 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0128] In one embodiment of the present invention, R1 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0129] In one embodiment of the present invention, R1 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0130] In one embodiment of the invention, R1 is hydrogen; deuterium; a deuterium-substituted or unsubstituted alkyl group; or a deuterium-substituted or unsubstituted aryl group.

[0131] In one embodiment of the present invention, R1 is hydrogen; deuterium; an alkyl group having 1 to 60 carbon atoms which is unsubstituted or substituted with deuterium; or an aryl group having 6 to 60 carbon atoms which is unsubstituted or substituted with deuterium.

[0132] In one embodiment of the present invention, R1 is hydrogen; deuterium; an alkyl group having 1 to 30 carbon atoms which is unsubstituted or substituted with deuterium; or an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with deuterium.

[0133] In one embodiment of the present invention, R1 is hydrogen; deuterium; an alkyl group having 1 to 20 carbon atoms which is unsubstituted or substituted with deuterium; or an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with deuterium.

[0134] In one embodiment of the present invention, R1 is hydrogen; or deuterium.

[0135] In one embodiment of the present invention, m is an integer of 0-9. In one embodiment of the present invention, m is an integer from 1 to 9. In one embodiment of the invention, m is 0. In one embodiment of the invention, m is 1. In one embodiment of the invention, m is 2. In one embodiment of the invention, m is 3. In one embodiment of the invention, m is 4. In one embodiment of the invention, m is 5. In one embodiment of the invention, m is 6. In one embodiment of the invention, m is 7. In one embodiment of the invention, m is 8. In one embodiment of the invention, m is 9.

[0136] In one embodiment of the invention, m is 9 and R1 are all deuterium. In one embodiment of the invention, m is 9 and 8 of the 9 R1 are deuterium. In one embodiment of the invention, m is 9 and 7 of the 9 R1 are deuterium. In one embodiment of the invention, m is 9 and 6 of the 9 R1 are deuterium. In one embodiment of the invention, m is 9 and five of the nine R1 are deuterium. In one embodiment of the invention, m is 9 and 4 of the 9 R1 are deuterium. In one embodiment of the invention, m is 9 and three of the nine R1 are deuterium. In one embodiment of the present invention, m is 9 and two of the nine R1 are deuterium. In one embodiment of the invention, m is 9 and one of the nine R1 is deuterium.

[0137] In one embodiment of the invention, D is deuterium.

[0138] In one embodiment of the present invention, n is an integer of 0-8. In one embodiment of the present invention, n is an integer from 1 to 8. In one embodiment of the invention, n is 0. In one embodiment of the invention, n is 1. In one embodiment of the invention, n is 2. In one embodiment of the invention, n is 3. In one embodiment of the invention, n is 4. In one embodiment of the invention, n is 5. In one embodiment of the invention, n is 6. In one embodiment of the invention, n is 7. In one embodiment of the invention, n is 8.

[0139] In one embodiment of the present invention, R2 to R6 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a substituted or unsubstituted alkyl group; or a group represented by formula A below.

[0140] In one embodiment of the present invention, R2 to R6 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; or a group represented by the following formula A.

[0141] In one embodiment of the present invention, R2 to R6 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a group represented by the following formula A.

[0142] In one embodiment of the present invention, R2 to R6 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a group represented by the following formula A.

[0143] In one embodiment of the present invention, R2 to R6 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a group represented by the following formula A.

[0144] In one embodiment of the present invention, R2 to R6 are the same or different and each independently represent a hydrogen atom; a deuterium atom; an alkyl group unsubstituted or substituted with a deuterium atom; or a group represented by the following formula A:

[0145] In one embodiment of the present invention, R2 to R6 are the same or different and each independently represent a hydrogen atom; a deuterium atom; an alkyl group having 1 to 60 carbon atoms which is unsubstituted or substituted with deuterium; or the following formula A.

[0146] In one embodiment of the present invention, R2 to R6 are the same or different and each independently represent a hydrogen atom; a deuterium atom; an alkyl group having 1 to 30 carbon atoms which is unsubstituted or substituted with deuterium; or the following formula A.

[0147] In one embodiment of the present invention, R2 to R6 are the same or different and each independently represent a hydrogen atom; a deuterium atom; an alkyl group having 1 to 20 carbon atoms which is unsubstituted or substituted with deuterium; or the following formula A.

[0148] In one embodiment of the present invention, R2 to R6 are the same or different and each independently represent a hydrogen atom; a deuterium atom; an alkyl group having 1 to 10 carbon atoms which is unsubstituted or substituted with deuterium; or the following formula A.

[0149] In one embodiment of the present invention, R2 to R6 are the same or different and each independently represent hydrogen; deuterium; or formula A below.

[0150] In one embodiment of the present invention, at least one of R2 and R6 is of formula A:

[0151] In one embodiment of the invention, one of R2 and R6 is of formula A:

[0152] In one embodiment of the invention, R2 is of formula A:

[0153] In one embodiment of the present invention, R6 is of formula A:

[0154] In one embodiment of the present invention, R2 is represented by the following formula A, and R3 to R6 are the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0155] In one embodiment of the present invention, R2 is represented by the following formula A, and R3 to R6 are the same or different and each independently represent hydrogen or deuterium.

[0156] In one embodiment of the present invention, R6 is represented by the following formula A, and R2 to R5 are the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0157] In one embodiment of the present invention, R6 is represented by the following formula A, and R2 to R5 are the same or different and each independently represent hydrogen or deuterium.

[0158] [ka] In the above chemical formula A, R7 to R11 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring; The dotted lines (---) are the sites of attachment to Chemical Formula 2.

[0159] In one embodiment of the present invention, R7 to R11 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring.

[0160] In one embodiment of the present invention, R7 to R11 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or are bonded to adjacent groups to form a substituted or unsubstituted ring.

[0161] In one embodiment of the present invention, R7 to R11 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or are bonded to adjacent groups to form a substituted or unsubstituted ring.

[0162] In one embodiment of the present invention, R7 to R11 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or are bonded to adjacent groups to form a substituted or unsubstituted ring.

[0163] In one embodiment of the present invention, R7 to R11 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or are bonded to adjacent groups to form a substituted or unsubstituted ring.

[0164] In one embodiment of the present invention, R7 to R11 are the same or different and each independently represent hydrogen; deuterium; an alkyl group substituted or unsubstituted with deuterium; or an aryl group substituted or unsubstituted with deuterium, or are bonded to adjacent groups to form a substituted or unsubstituted ring.

[0165] In one embodiment of the present invention, R7 to R11 are the same or different and each independently represent hydrogen; deuterium; an alkyl group having 1 to 60 carbon atoms which is substituted or unsubstituted with deuterium; or an aryl group having 6 to 60 carbon atoms which is substituted or unsubstituted with deuterium, or adjacent groups are bonded to each other to form a ring which is substituted or unsubstituted with deuterium.

[0166] In one embodiment of the present invention, R7 to R11 are the same or different and each independently represent hydrogen; deuterium; an alkyl group having 1 to 30 carbon atoms which is substituted or unsubstituted with deuterium; or an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium, or adjacent groups are bonded to each other to form a ring which is substituted or unsubstituted with deuterium.

[0167] In one embodiment of the present invention, R7 to R11 are the same or different and each independently represent hydrogen; deuterium; an alkyl group having 1 to 20 carbon atoms which is substituted or unsubstituted with deuterium; or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium, or adjacent groups are bonded to each other to form a ring which is substituted or unsubstituted with deuterium.

[0168] In one embodiment of the present invention, R7 to R11 are the same or different and each independently is hydrogen or deuterium.

[0169] In one embodiment of the present invention, among R1 to R11, the remaining ones other than those of the chemical formula A are the same or different, and each independently is hydrogen or deuterium.

[0170] In one embodiment of the present invention, the formula 2 contains at least one deuterium.

[0171] In one embodiment of the present invention, the above-mentioned formula 2 is represented by the following formula 2-1. [ka] In the above Chemical Formula 2-1, the definitions of R1, m, D, n, and R3 to R11 are the same as those in the above Chemical Formula 2.

[0172] In one embodiment of the present invention, the compound represented by Chemical Formula 2 is at least 40% substituted with deuterium. In yet another embodiment, the compound represented by Chemical Formula 2 is 50% or more substituted with deuterium. In yet another embodiment, the compound represented by Chemical Formula 2 is 60% or more substituted with deuterium. In yet another embodiment, the compound represented by Chemical Formula 2 is 70% or more substituted with deuterium. In yet another embodiment, the compound represented by Chemical Formula 2 is 80% or more substituted with deuterium. In yet another embodiment, the compound represented by Chemical Formula 2 is 90% or more substituted with deuterium. In yet another embodiment, the compound represented by Chemical Formula 2 is 100% substituted with deuterium.

[0173] In one embodiment of the present invention, the compound represented by chemical formula 2 contains 40% to 60% deuterium. In another embodiment, the compound represented by chemical formula 2 contains 40% to 80% deuterium. In another embodiment, the compound represented by chemical formula 2 contains 60% to 80% deuterium. In another embodiment, the compound represented by chemical formula 2 contains 80% to 100% deuterium.

[0174] In one embodiment of the present invention, the formula 2 is represented by any one of the following compounds:

[0175] [ka]

[0176] In the compounds represented by Chemical Formula 1 and Chemical Formula 2 according to an embodiment of the present invention, the core structure may be prepared as in the preparation examples described below. Substituents may be attached by methods known in the art, and the type, position or number of substituents may be changed by techniques known in the art.

[0177] In the present invention, compounds having various energy band gaps can be synthesized by incorporating various substituents into the core structures of the compounds represented by Chemical Formula 1 and Chemical Formula 2. In addition, in the present specification, the HOMO and LUMO energy levels of the compounds can also be adjusted by incorporating various substituents into the core structures of the above-mentioned structures.

[0178] The organic light-emitting device will now be described.

[0179] In this specification, when a member is said to be located "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member is present between the two members.

[0180] In this specification, when a part "comprises" a certain component, this does not mean to exclude other components, but means that it may further include other components, unless specifically stated to the contrary.

[0181] The organic light emitting device according to the present invention comprises an anode; a cathode; and a first organic layer and a second organic layer disposed between the anode and the cathode, the first organic layer comprising a compound represented by the following Chemical Formula 1, and the second organic layer comprising a compound represented by the following Chemical Formula 2:

[0182] The organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that the organic material layer is formed using the compound represented by the above-mentioned Chemical Formula 1 and the compound represented by the above-mentioned Chemical Formula 2.

[0183] In manufacturing an organic light emitting device, the compound may be formed in an organic layer by a solution coating method as well as a vacuum deposition method, where the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0184] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are laminated.For example, the organic light-emitting device of the present invention may have a structure including one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as the organic layer.However, the structure of the organic light-emitting device of the present specification is not limited thereto, and may include a smaller or larger number of organic layers.

[0185] In one embodiment of the present invention, the first organic layer may be located between the second organic layer and the cathode.

[0186] In one embodiment of the present invention, the first organic layer may be an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, the electron injection layer, or the electron transport and injection layer may contain a compound represented by Chemical Formula 1.

[0187] In one embodiment of the present invention, the second organic layer may be a light-emitting layer, and the light-emitting layer may contain the compound represented by Chemical Formula 2.

[0188] In one embodiment of the present invention, the light emitting layer contains the compound represented by Chemical Formula 2 as a host, and may further contain a dopant.

[0189] In the organic light emitting device according to an embodiment of the present invention, the organic layer may include two or more layers of a hole injection layer, a hole transport layer, or an electron blocking layer.

[0190] In the organic light emitting device according to an embodiment of the present invention, the organic layer may include two or more layers of an electron injection layer, an electron transport layer, or a hole blocking layer.

[0191] In one embodiment of the present invention, the first organic layer containing the compound represented by Chemical Formula 1 and the second organic layer containing the compound represented by Chemical Formula 2 have a thickness of 10 Å to 600 Å, preferably 50 Å to 500 Å, and more preferably 200 Å to 400 Å.

[0192] In another embodiment, the first organic layer and the second organic layer may further contain other organic compounds, metals, or metal compounds in addition to the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

[0193] In another embodiment, the first organic layer and the second organic layer do not contain any other organic compounds, metals or metal compounds other than the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

[0194] In one embodiment of the present invention, the first organic layer and the second organic layer may be provided in contact with each other.

[0195] In one embodiment of the present invention, the first organic layer and the second organic layer do not have to be provided in contact with each other.

[0196] In one embodiment of the present invention, one or more organic layers are located between the first organic layer and the second organic layer.

[0197] In one embodiment of the present invention, a hole blocking layer is located between the first organic layer and the second organic layer.

[0198] In the organic light emitting device according to an embodiment of the present invention, the light emitting layer further comprises a fluorescent dopant or a phosphorescent dopant, wherein the dopant in the light emitting layer is contained in an amount of 1 to 50 parts by weight based on 100 parts by weight of the host.

[0199] In this case, the dopant may be a phosphorescent material such as (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distyrubenzene (DSB), distyrylarylene (DSA), a PFO-based polymer, a PPV-based polymer, an anthracene-based compound, a pyrene-based compound, or a boron-based compound, but is not limited thereto.

[0200] In one embodiment of the present invention, the organic light-emitting device includes an anode; a cathode; and two or more organic layers provided between the anode and the cathode, and at least one of the two or more organic layers includes a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2.

[0201] In one embodiment of the present invention, the two or more organic layers may be two or more selected from the group consisting of a light-emitting layer, a hole-transporting layer, a hole-injecting layer, a hole-transporting and injection layer, and an electron-blocking layer.

[0202] In one embodiment of the present invention, the two or more organic layers may be two or more selected from the group consisting of an emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron modulating layer and a hole blocking layer.

[0203] In one embodiment of the present invention, the organic layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2. Specifically, in one embodiment of the present specification, the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 may be included in one of the two or more electron transport layers, or may be included in each of the two or more electron transport layers.

[0204] In addition, in one embodiment of the present invention, when the compound is contained in each of the two or more electron transport layers, materials other than the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 may be the same as or different from each other.

[0205] When the organic layer containing the compound represented by Chemical Formula 1 or the compound represented by Chemical Formula 2 is an electron transport layer, an electron injection layer, or an electron transport and injection layer, the electron transport layer, the electron injection layer, or the electron transport and injection layer may further contain an n-type dopant. The n-type dopant may be one known in the art, for example, a metal or a metal complex. For example, the electron transport layer containing the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 may further contain LiQ (Lithium Quinolate). According to one example, the total of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 and the n-type dopant may be contained in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.

[0206] According to an example, the total of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 and the n-type dopant may be included in a weight ratio of 1:1.

[0207] According to an embodiment of the present invention, the organic light-emitting device further includes one or more organic layers between the anode and the cathode, and the organic layers may further include one or more of a hole transport layer, a hole injection layer, a hole transport and injection layer, an electron blocking layer, an emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, and a hole blocking layer.

[0208] The organic light emitting device according to an embodiment of the present invention may further comprise one or more light emitting layers.

[0209] The organic light emitting device according to an embodiment of the present invention further includes one or more light emitting layers in addition to the light emitting layer, and each light emitting layer may include the host compound described above.

[0210] According to an embodiment of the present invention, the organic light emitting device further comprises one or more light emitting layers in addition to the light emitting layer, and each light emitting layer further comprises a fluorescent dopant or a phosphorescent dopant, wherein the dopant in the light emitting layer is contained in an amount of 1 to 50 parts by weight based on 100 parts by weight of the host.

[0211] The organic light emitting device according to an embodiment of the present invention may include two or more light emitting layers.

[0212] An organic light-emitting device according to one embodiment of the present invention comprises two or more light-emitting layers, at least one of which comprises a fluorescent dopant and at least one of which comprises a phosphorescent dopant.

[0213] The organic light-emitting device according to an embodiment of the present invention may include three or more light-emitting layers.

[0214] In the organic light-emitting device according to one embodiment of the present invention, the maximum emission peak of the light-emitting layer is from 400 nm to 500 nm.

[0215] An organic light-emitting device according to one embodiment of the present invention includes two or more light-emitting layers, and the maximum emission peak of each of the two or more light-emitting layers is 400 nm to 500 nm.

[0216] The organic light-emitting device according to one embodiment of the present invention further comprises one or more light-emitting layers, each of which exhibits a different wavelength band.

[0217] An organic light-emitting device according to one embodiment of the present invention includes three or more light-emitting layers, in which one light-emitting layer (light-emitting layer 1) has a maximum emission peak of 400 nm to 500 nm, another light-emitting layer (light-emitting layer 2) may have a maximum emission peak of 510 nm to 580 nm or 610 nm to 680 nm, and another light-emitting layer (light-emitting layer 3) may have a maximum emission peak of 400 nm to 500 nm.

[0218] According to one embodiment of the present invention, the two or more light-emitting layers may be positioned vertically or horizontally between the anode and the cathode.

[0219] According to one embodiment of the present invention, the three or more light-emitting layers are positioned in a vertical direction from the anode to the cathode, and all of the three or more light-emitting layers may be blue fluorescent layers.

[0220] When the organic light-emitting device according to an embodiment of the present invention includes a plurality of light-emitting layers, one or more organic layers may be further provided between the plurality of light-emitting layers, and the organic layers may further include one or more of a hole transport layer, a hole injection layer, a hole transport and injection layer, an electron blocking layer, a charge generation layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, and a hole blocking layer.

[0221] In one embodiment of the present invention, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially laminated on a substrate.

[0222] In one embodiment of the present invention, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0223] The organic light emitting device may have, for example, the following laminated structure, but is not limited thereto. (1) Anode / hole transport layer / light emitting layer / cathode (2) Anode / hole injection layer / hole transport layer / light emitting layer / cathode (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode (4) Anode / hole transport layer / light emitting layer / electron transport layer / cathode (5) Anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode (6) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode (7) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode (10) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode (11) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode (14) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode (15) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode (16) Anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode (17) Anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode (18) Anode / hole injection layer / first hole transport layer / second hole transport layer / light emitting layer / electron transport and injection layer / cathode

[0224] The structure of the organic light-emitting device of the present invention may have the same structures as those shown in FIGS. 1 to 3, but is not limited to these.

[0225] 1 illustrates an example of a structure of an organic light-emitting device in which a substrate 1, an anode 2, a second organic layer 22, a first organic layer 21, and a cathode 10 are sequentially stacked. In this structure, the compound represented by Chemical Formula 1 may be included in the first organic layer 21, and the compound represented by Chemical Formula 2 may be included in the second organic layer 22.

[0226] 2 illustrates an example of a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, an emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10 are sequentially stacked. In this structure, the compound represented by Chemical Formula 1 may be included in the electron transport layer 8 or the electron injection layer 9, and the compound represented by Chemical Formula 2 may be included in the emitting layer 6.

[0227] 3 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, an emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 11, and a cathode 10 are sequentially stacked. In this structure, the compound represented by Chemical Formula 1 may be included in the electron injection and transport layer 11, and the compound represented by Chemical Formula 2 may be included in the emitting layer 6.

[0228] According to one embodiment of the present invention, the organic light emitting device may have a tandem structure in which two or more independent devices are connected in series. In one embodiment, the tandem structure may be a form in which each organic light emitting device is joined to a charge generation layer. Since a device having a tandem structure can be driven with a lower current than a unit device based on the same luminance, it has an advantage that the life characteristics of the device are greatly improved.

[0229] In one embodiment of the present invention, the electron transport and injection layer and the light emitting layer may be provided adjacent to each other. For example, the electron transport and injection layer and the light emitting layer may be provided so as to be physically adjacent to each other.

[0230] In one embodiment of the present invention, the electron transport layer and the light emitting layer may be provided adjacent to each other. For example, the electron transport layer and the light emitting layer may be provided physically adjacent to each other.

[0231] In one embodiment of the present invention, the hole blocking layer and the light emitting layer may be provided adjacent to each other. For example, the hole blocking layer and the light emitting layer may be provided physically adjacent to each other.

[0232] The organic light-emitting device of the present invention may be manufactured using materials and methods known in the art, except that at least one of the organic layers contains the above-mentioned compounds, i.e., the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

[0233] When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0234] For example, the organic light emitting device according to the present disclosure may be manufactured by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form an anode, forming organic layers including a hole injection layer, a hole transport layer, an emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon. Alternatively, the organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0235] The organic layer may further include one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

[0236] The organic layer may have a multi-layer structure including, but not limited to, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, or an electron transport and injection layer, etc. Also, the organic layer may be manufactured in a smaller number of layers by a solvent process other than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method, using various polymer materials.

[0237] The anode is an electrode that injects holes, and the anode material is preferably a material with a large work function so that holes can be easily injected into the organic layer. Specific examples of the anode material used in the present invention 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.

[0238] The cathode is an electrode that injects electrons, and the cathode material is preferably a material with a small work function so that electrons can be easily injected into the organic layer. Specific examples of the cathode 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 materials with a multilayer structure such as LiF / Al or LiO2 / Al.

[0239] The hole injection layer is a layer that facilitates the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can smoothly inject holes from the anode at a low voltage, and the HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include the above-mentioned compounds or 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, but are not limited thereto.

[0240] The thickness of the hole injection layer may be 1 Å to 150 Å. When the thickness of the hole injection layer is 1 Å or more, it is advantageous in that it is possible to prevent a decrease in hole injection characteristics, and when it is 150 Å or less, it is advantageous in that it is possible to prevent an increase in driving voltage due to an increase in the mobility of holes caused by the hole injection layer being too thick.

[0241] In one embodiment of the present invention, the hole injection material may include an arylamine compound containing a carbazole group and a tetrafluorobenzonitrile compound. According to one example, the amine compound is represented as Het101-L101-N(Ar101)(Ar102), where Het101 is a substituted or unsubstituted carbazole group, L101 is a direct bond or a substituted or unsubstituted arylene group, and Ar101 and Ar102 may be the same or different and each independently be a substituted or unsubstituted aryl group. The amine compound and the tetrafluorobenzonitrile compound may be included in a suitable molar ratio, and according to one example, the amine compound and the tetrafluorobenzonitrile compound may be included in a molar ratio of 99.9:0.1 to 90:10.

[0242] The hole transport layer can facilitate the transport of holes. As the hole transport material, a material that can receive holes from the anode or the hole injection layer and transfer them to the light emitting layer and has high mobility for holes is suitable. Specific examples include, but are not limited to, the above-mentioned compounds or arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions. In one embodiment of the present specification, the hole transport material may include an arylamine compound containing a carbazole group.

[0243] A hole buffer layer may further be provided between the hole injection layer and the hole transport layer and may comprise the compounds described above or hole injection or transport materials known in the art.

[0244] An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may be made of the above-mentioned compounds or materials known in the art. Specifically, in one embodiment of the present invention, the electron blocking material may be an arylamine-based compound containing a phenanthrenyl group, but is not limited thereto.

[0245] The light-emitting layer may emit red, green or blue light and may be made of a phosphorescent or fluorescent material. The light-emitting material is a material that can emit light in the visible light range by receiving and combining holes and electrons from the hole transport layer and electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited thereto.

[0246] The host material of the light-emitting layer may be a condensed aromatic ring derivative or a heterocyclic ring-containing compound, etc. Specifically, the condensed aromatic ring derivative may be an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, etc., and the heterocyclic ring-containing compound may be, but is not limited to, a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, etc.

[0247] When the light-emitting layer emits red light, the light-emitting dopant may be, but is not limited to, a phosphorescent material such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), or PtOEP(octaethylporphyrin platinum), or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum). When the light-emitting layer emits green light, the light-emitting dopant may be, but is not limited to, a phosphorescent material such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium), or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum), an anthracene-based compound, a pyrene-based compound, or a boron-based compound. When the light-emitting layer emits blue light, the light-emitting dopant may be, but is not limited to, a phosphorescent material such as (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distyrubenzene (DSB), distyrylarylene (DSA), a PFO-based polymer, a PPV-based polymer, an anthracene-based compound, a pyrene-based compound, or a boron-based compound.

[0248] In one embodiment of the present invention, the light emitting layer material may be a compound according to Formula 2 of the present invention, an anthracene-based compound, or a boron-based compound.

[0249] A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and the hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer.Specific examples of the hole blocking layer include, but are not limited to, oxadiazole derivatives, triazole derivatives, triazine derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0250] In one embodiment of the present invention, the hole blocking material may include a compound represented by the following formula HB:

[0251] [ka] In the formula HB, L is a direct bond; a substituted or unsubstituted arylene group; a substituted or unsubstituted alkylene group; a substituted or unsubstituted divalent alkoxy group; a substituted or unsubstituted divalent alkenyl group; or a substituted or unsubstituted heteroarylene group; X1 is N; or CR11, X2 is N; or CR12, and X3 is N; or CR13; At least one of X1 to X3 is N; R11 to R13 are the same or different and each independently represents hydrogen; deuterium; a cyano group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; Ar3 and Ar4 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted arylalkenyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0252] According to one embodiment of the present invention, L is a direct bond; a substituted or unsubstituted arylene group; a substituted or unsubstituted alkylene group; a substituted or unsubstituted divalent alkoxy group; a substituted or unsubstituted divalent alkenyl group; or a substituted or unsubstituted heteroarylene group.

[0253] According to one embodiment of the present invention, L is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

[0254] According to one embodiment of the present invention, L is a direct bond; or a substituted or unsubstituted arylene group.

[0255] According to one embodiment of the present invention, L is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0256] According to one embodiment of the present invention, L is a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0257] According to one embodiment of the present invention, L is a direct bond; or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0258] According to one embodiment of the present invention, L is a direct bond; or a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.

[0259] According to one embodiment of the invention, L is a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0260] According to one embodiment of the invention, L is a direct bond; a phenylene group; or a biphenylene group.

[0261] According to one embodiment of the invention, L is a direct bond; or a phenylene group.

[0262] According to one embodiment of the invention, L is a direct bond.

[0263] According to one embodiment of the present invention, R11 to R13 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0264] According to one embodiment of the present invention, R11 to R13 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0265] According to one embodiment of the present invention, R11 to R13 are hydrogen or deuterium.

[0266] According to one embodiment of the present invention, R11 to R13 are hydrogen.

[0267] According to one embodiment of the present invention, Ar3 and Ar4 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0268] According to one embodiment of the present invention, Ar3 and Ar4 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0269] According to one embodiment of the present invention, Ar3 and Ar4 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0270] According to one embodiment of the present invention, Ar3 and Ar4 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0271] According to one embodiment of the present invention, Ar3 and Ar4 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group.

[0272] According to one embodiment of the present invention, Ar3 and Ar4 are the same or different and each independently a phenyl group; or a biphenyl group.

[0273] In one embodiment of the present invention, the formula HB is represented by any one of the following chemical formulae HB-A to HB-D.

[0274] [ka] [ka]

[0275] In the chemical formulas HB-A to HB-D, the definitions of L, Ar3, Ar4 and X1 to X3 are the same as those in the chemical formula HB.

[0276] The electron transport layer can facilitate the transport of electrons. As the electron transport material, a material having high mobility for electrons, which can easily receive electrons from the cathode and transfer them to the light emitting layer, is suitable. Specific examples include, but are not limited to, the 8-hydroxyquinoline Al complex; a complex containing Alq3; an organic radical compound; and a hydroxyflavone-metal complex. The thickness of the electron transport layer may be 1 to 500 Å. When the thickness of the electron transport layer is 1 Å or more, it is advantageous in that the electron transport property can be prevented from being deteriorated, and when the thickness is 500 Å or less, it is advantageous in that the driving voltage can be prevented from being increased due to the electron transport layer being too thick to improve the movement of electrons.

[0277] The electron injection layer can facilitate the injection of electrons. As the electron injection material, a compound having the ability to transport electrons, an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or light emitting material, preventing the movement of excitons generated in the light emitting layer to the hole injection layer, and excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives are included, but are not limited thereto.

[0278] 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.

[0279] In one embodiment of the present invention, the electron injection and transport material may include a compound according to Formula 1 of the present invention or a triazine compound, and may further include an n-type dopant or an organometallic compound. According to one example, the n-type dopant or organometallic compound may be LiQ, and the triazole compound and the n-type dopant (or organometallic compound) may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4. The organic light emitting device according to the present invention may be a front emission type, a rear emission type, or a dual emission type, depending on the materials used. EXAMPLES

[0280] In the following, the present invention will be described in detail with reference to examples in order to specifically explain the present invention. However, the examples of the present invention can be modified into various other forms, and the scope of the present application is not to be construed as being limited by the examples detailed below. The examples of the present invention are provided to more completely explain the present specification to those having average knowledge in the art.

[0281] <Production Example 1> [ka]

[0282] In a 500 ml round-bottom flask in a nitrogen atmosphere, the compound 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (5.50 g, 11.84 mmol), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile (6.30 g, 13.03 mmol) were completely dissolved in 240 ml of tetrahydrofuran, and then 2 M potassium carbonate aqueous solution (120 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.41 g, 0.36 mmol) was added, followed by heating and stirring for 8 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 320 ml of toluene to produce compound 1-1 (5.88 g, 73%). MS[M+H] + =741

[0283] <Production Example 2> [ka]

[0284] In a 500ml round-bottom flask under nitrogen atmosphere, compound 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (5.50g, 14.18mmol), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile (7.54g, 15.59mmol) were completely dissolved in 240ml of tetrahydrofuran, 2M potassium carbonate aqueous solution (120ml) was added, tetrakis-(triphenylphosphine)palladium (0.49g, 0.43mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 310ml of toluene to produce compound 1-2 (6.21g, 66%). MS[M+H] + =665

[0285] <Production Example 3> [ka]

[0286] In a 500ml round-bottom flask under nitrogen atmosphere, compound 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (5.50g, 14.18mmol), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile (7.54g, 15.59mmol) were completely dissolved in 260ml of tetrahydrofuran, 2M potassium carbonate aqueous solution (130ml) was added, tetrakis-(triphenylphosphine)palladium (0.49g, 0.43mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280ml of ethyl acetate to produce compound 1-3 (6.41g, 68%). MS[M+H] + =665

[0287] <Production Example 4> [ka]

[0288] In a nitrogen atmosphere, compound a (6.50 g, 15.57 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,3-b]benzofuran-1-yl)-1,3,2-dioxaborolane (5.90 g, 17.13 mmol) were completely dissolved in 240 ml of tetrahydrofuran in a 500 ml round-bottom flask, 2 M potassium carbonate aqueous solution (120 ml) was added, tetrakis-(triphenylphosphine)palladium (0.54 g, 0.47 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 320 ml of ethyl acetate to produce compound 2-1 (5.91 g, 68%). MS[M+H] + =555

[0289] <Production Example 5> [ka]

[0290] In a 500ml round-bottom flask under nitrogen atmosphere, compound b (6.50g, 15.26mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,3-b]benzofuran-1-yl)-1,3,2-dioxaborolane (5.78g, 16.78mmol) were completely dissolved in 240ml of tetrahydrofuran, 2M potassium carbonate aqueous solution (120ml) was added, tetrakis-(triphenylphosphine)palladium (0.53g, 0.46mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 340ml of ethyl acetate to produce compound 2-2 (6.67g, 78%). MS[M+H] + =564

[0291] <Production Example 6> [ka]

[0292] In a nitrogen atmosphere, compound c (6.50 g, 15.55 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,3-b]benzofuran-1-yl)-1,3,2-dioxaborolane (5.89 g, 17.11 mmol) were completely dissolved in 220 ml of tetrahydrofuran in a 500 ml round-bottom flask, 2 M potassium carbonate aqueous solution (110 ml) was added, tetrakis-(triphenylphosphine)palladium (0.54 g, 0.47 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 ml of ethyl acetate to produce compound 2-3 (6.34 g, 73%). MS[M+H] + =556

[0293] <Comparative Example 1> A glass substrate coated with a 1,000 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. The distilled water used was distilled water filtered twice with a filter manufactured by Millipore Co. The ITO was washed for 30 minutes, then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After washing with distilled water, the substrate 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 for 5 minutes using oxygen plasma and then transferred to a vacuum deposition chamber.

[0294] On the ITO transparent electrode thus prepared, compounds of the following formula [HI-1] and the following formula [HI-2] were thermally vacuum deposited to a thickness of 100 Å in a ratio of 98:2 (molar ratio) to form a hole injection layer.

[0295] [ka]

[0296] The following compound [HT-1] (1150 Å), which is a material for transporting holes, was vacuum-deposited on the hole injection layer to form a hole transport layer.

[0297] [ka]

[0298] Next, the following compound [EB-1] (150 Å) was vacuum-deposited on the hole transport layer to a thickness of 50 Å to form an electron blocking layer.

[0299] [ka]

[0300] Next, a light-emitting layer was formed on the electron blocking layer by vacuum deposition of BH-1 and BD-1 in a weight ratio of 40:1 to a thickness of 200 Å.

[0301] [ka]

[0302] The compound [HB-1] was vacuum-deposited on the light-emitting layer to a thickness of 50 Å to form a hole-blocking layer.

[0303] Next, the compound [ET-1] and the compound LiQ (lithium quinolate) were vacuum-deposited on the hole blocking layer in a weight ratio of 1:1 to form an electron transport and injection layer having a thickness of 300 Å.

[0304] Lithium fluoride (LiF) was sequentially deposited to a thickness of 12 Å and aluminum to a thickness of 2,000 Å on the electron transport and injection layer to form a negative electrode.

[0305] In this process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of lithium fluoride on the negative electrode was maintained at 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. The degree of vacuum during deposition was 2×10 -7 ~5×10 -6 The organic light-emitting device was fabricated under a constant pressure of 1000 MPa.

[0306] Comparative Examples 2 to 12 An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 1 below were used instead of [ET-1] and [BH-1] in Comparative Example 1.

[0307] Experimental Example 1-1 to Experimental Example 1-9 An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 1 below were used instead of [ET-1] and [BH-1] in Comparative Example 1.

[0308] [ka] [ka]

[0309] Comparative Examples 13 to 15 An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that compounds 1-1, 1-2, and 1-3 were used instead of [ET-1].

[0310] Comparative Examples 16 to 18 Organic light emitting devices were manufactured in the same manner as in Comparative Example 1, except that compounds 2-1, 2-2, and 2-3 were used instead of [BH-1].

[0311] Comparative Examples 19 to 21 An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that compounds 2-1, 2-2, and 2-3 were used instead of [BH-1], and [ET-2] was used instead of [ET-1].

[0312] Comparative Examples 22 to 36 An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 1 below were used instead of [ET-1] and [BH-1] in Comparative Example 1.

[0313] Comparative Examples 37 to 45 An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that compounds 1-1, 1-2, and 1-3 were used instead of [ET-1] in Comparative Example 1, and [BH-7] to [BH-9] were used instead of [BH-1].

[0314] The organic light emitting devices manufactured in the above experimental examples and comparative examples were subjected to a current of 20 mA / cm 2 When a current of 20 mA / cm was applied to the fabricated organic light emitting device, 2 The driving voltage, luminous efficiency, and color coordinates were measured at a current density of 20 mA / cm 2 The time (T95) required for the brightness to decrease to 95% of the initial brightness at a current density of 1,600 nit was measured. The results are shown in Table 1 below. T95 refers to the time it takes for the brightness to decrease to 95% from the initial brightness (1,600 nit).

[0315] [Table 1] [Table 2] [Table 3]

[0316] As shown in Table 1, Experimental Examples 1-1 to 1-9 show the characteristics of devices in which the compounds represented by Chemical Formula 1 and Chemical Formula 2 are used together as materials for the electron transport layer, the electron injection layer, and the light emitting layer, respectively.

[0317] Comparative Examples 1 to 12 show the device characteristics when ET-1 or ET-2 is used as the electron transport and injection layer, and one of BH-1 to BH-6 is used as the light emitting layer.

[0318] Comparative Examples 13 to 36 show the characteristics of elements using the compounds represented by Chemical Formula 1 and Chemical Formula 2 separately, in which the compound represented by Chemical Formula 1 was used in place of ET-1 or ET-2, or the compound represented by Chemical Formula 2 was used in place of any one of BH-1 to BH-6.

[0319] Comparative Examples 37 to 45 show the device characteristics when BH-7 to BH-10 were used in place of the compound of Chemical Formula 2.

[0320] Therefore, compared to the comparative example, the organic light-emitting devices of the experimental examples basically exhibit characteristics of low voltage, high efficiency, and long life. In particular, it can be confirmed that the compound of Chemical Formula 1 has high efficiency characteristics, and the compound of Chemical Formula 2 has long life characteristics.

[0321] Specifically, when comparing Experimental Examples 1-1 to 1-9 with Comparative Examples 16 to 21, Experimental Examples 1-1 to 1-9, which use the compound of Chemical Formula 1 and the compound of Chemical Formula 2, showed results in which the efficiency was increased by up to approximately 12% compared to Comparative Examples 16 to 21, which do not use the compound of Chemical Formula 1.

[0322] Furthermore, when comparing Experimental Examples 1-1 to 1-9 with Comparative Examples 13 to 15 and 22 to 36, Experimental Examples 1-1 to 1-9, which use the compound of Chemical Formula 1 and the compound of Chemical Formula 2, showed results in which the lifespan was increased by up to approximately 72% compared to Comparative Examples 13 to 15 and 22 to 36, which did not use the compound of Chemical Formula 2.

[0323] Comparative Examples 19 to 21 are cases where a compound (ET-2) not containing a cyano group was used. Comparing Experimental Examples 1-1 to 1-9 with Comparative Examples 19 to 21, it can be seen that Experimental Examples 1-1 to 1-9, which use a compound of Chemical Formula 1 containing a cyano group, have lower driving voltages, higher luminous efficiency, and longer lifespans than Comparative Examples 19 to 21.

[0324] Comparative Examples 22 to 24 are cases where a compound (BH-2) in which a phenyl group and a dibenzofuran group are linked to an anthracene core is used. Comparing Experimental Examples 1-1 to 1-9 with Comparative Examples 22 to 24, it can be seen that Experimental Examples 1-1 to 1-9, which use a compound of Chemical Formula 2 in which a naphthobenzofuran group and a biphenyl group are linked to an anthracene core, have a lower driving voltage, a higher luminous efficiency, and a longer life than Comparative Examples 22 to 24.

[0325] Comparative Examples 25 to 27 and 43 to 45 are cases where compounds (BH-3 and BH-9) in which the linking position of naphthobenzofuran is different from that of Chemical Formula 2 of the present invention are used. Comparing Experimental Examples 1-1 to 1-9 with Comparative Examples 25 to 27 and 43 to 45, it can be confirmed that Experimental Examples 1-1 to 1-9 in which the compound of Chemical Formula 2 of the present invention is used have a lower driving voltage, a higher luminous efficiency, and a longer lifetime than Comparative Examples 25 to 27 and 43 to 45 in which compounds (BH-3 and BH-9) in which the linking position of naphthobenzofuran is different from that of Chemical Formula 2 of the present invention are used.

[0326] Comparative Examples 28 to 30 are cases where a compound (BH-4) in which a biphenyl group and dibenzofuran are linked to an anthracene core is used. Comparing Experimental Examples 1-1 to 1-9 with Comparative Examples 28 to 30, it can be seen that Experimental Examples 1-1 to 1-9, which use a compound of Chemical Formula 2 in which naphthobenzofuran is linked to an anthracene core, have lower driving voltages, higher luminous efficiency, and longer lifetimes than Comparative Examples 28 to 30.

[0327] Comparative Examples 31 to 34 are cases where a compound (BH-5) in which the condensation position of benzene in naphthobenzofuran is different from that in Chemical Formula 2 of the present invention was used. Comparing Experimental Examples 1-1 to 1-9 with Comparative Examples 31 to 34, it can be confirmed that Experimental Examples 1-1 to 1-9 in which the compound of Chemical Formula 2 of the present invention was used had a lower driving voltage, a higher luminous efficiency, and a longer lifetime than Comparative Examples 31 to 34 in which a compound (BH-5) in which the condensation position of benzene in naphthobenzofuran is different from that in Chemical Formula 2 of the present invention was used.

[0328] Comparative Examples 34 to 36 are cases where a compound (BH-6) in which a naphthyl group is linked to the anthracene core instead of a biphenyl group is used. Comparing Experimental Examples 1-1 to 1-9 with Comparative Examples 34 to 36, it can be seen that Experimental Examples 1-1 to 1-9, which use the compound of Chemical Formula 2 in which a biphenyl group is linked to the anthracene core, have lower driving voltages, higher luminous efficiency, and longer lifetimes than Comparative Examples 34 to 36.

[0329] Comparative Examples 37 to 39 are the cases where a compound (BH-7) is used in which a biphenyl group containing a para-phenyl group is linked to an anthracene core instead of a biphenyl group containing an ortho-phenyl group. Comparing Experimental Examples 1-1 to 1-9 with Comparative Examples 37 to 39, it can be seen that Experimental Examples 1-1 to 1-9, which use a compound of Chemical Formula 2 in which a biphenyl group containing an ortho-phenyl group is linked to an anthracene core, have a lower driving voltage, higher luminous efficiency, and longer life than Comparative Examples 37 to 39.

[0330] Comparative Examples 40 to 42 are cases where a compound (BH-8) in which a phenyl group substituted with deuterium is linked to an anthracene core instead of a biphenyl group is used. Comparing Experimental Examples 1-1 to 1-9 with Comparative Examples 40 to 42, it can be seen that Experimental Examples 1-1 to 1-9, which use a compound of Chemical Formula 2 in which a biphenyl group is linked to an anthracene core, have a lower driving voltage, a higher luminous efficiency, and a longer lifetime than Comparative Examples 40 to 42.

[0331] Through this, it can be confirmed that when the compound of Chemical Formula 1 of the present invention is used as an electron transport and injection layer material and the compound of Chemical Formula 2 of the present invention is used in combination as an emission layer material, the organic light emitting device can have high efficiency characteristics while maintaining long life characteristics.

[0332] Although a preferred embodiment of the present invention (experiment on combination of electron transport and injection layer and light emitting layer) has been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention, which also fall within the scope of the invention. [Explanation of symbols]

[0333] 1. Circuit Board 2 Anode 3. Hole injection layer 4. Hole transport layer 5. Electron blocking layer 6. Emitting layer 7. Hole blocking layer 8...electron transport layer 9...electron injection layer 10 Cathode 11 Electron transport and injection layer 21...first organic layer 22...Second organic layer

Claims

1. anode; A cathode; and a first organic layer and a second organic layer provided between the anode and the cathode; The first organic layer includes a compound represented by the following Chemical Formula 1: The second organic material layer comprises a compound represented by the following Chemical Formula 2: 【Chemistry 1】 In the above Chemical Formula 1, Ar1 and Ar2 are the same or different and each independently represents hydrogen; deuterium; or a substituted or unsubstituted aryl group; L1 and L2 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted arylene group; X1 to X3 are the same or different and each independently represents N; or CR; At least one of X1 to X3 is N; Ra, Rb and R are the same or different and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; a is an integer of 0 to 6, and when a is 2 or more, two or more Ra's are the same or different, b is an integer of 0 to 8, and when b is 2 or more, two or more Rb's are the same or different, 【Chemistry 2】 In the above Chemical Formula 2, R1 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; m is an integer of 0 to 9, and when m is 2 or more, two or more R1's are the same or different, D is deuterium and n is an integer from 0 to 8; R2 to R6 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a group represented by the following formula A: At least one of R2 and R6 is represented by the following chemical formula A: 【Chemistry 3】 In the above chemical formula A, R7 to R11 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring; The dotted line (- - -) indicates the site of connection to Chemical Formula 2.

2. The organic light-emitting device according to claim 1, wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-4: 【Chemistry 4】 【Chemistry 5】 In the above Chemical Formula 1-1 to Chemical Formula 1-4, The definitions of Ar1, Ar2, L1, L2, X1 to X3, Ra, Rb, a, and b are the same as those in Formula 1.

3. The organic light emitting device according to claim 1, wherein the formula 1 is represented by any one of the following formulas 1-A to 1-D. 【Chemistry 6】 【Chemistry 7】 In Chemical Formula 1-A to Chemical Formula 1-D, The definitions of Ar1, Ar2, L1, L2, X1 to X3, Ra, Rb, a, and b are the same as those in Chemical Formula 1.

4. The organic light emitting device according to claim 1, wherein the formula 1 is represented by the following formula 1-1-1: 【Chemistry 8】 In the above Chemical Formula 1-1-1, The definitions of Ar1, Ar2, L1, L2, X1 to X3, Ra, Rb, a, and b are the same as those in Chemical Formula 1.

5. The organic light emitting device according to claim 1, wherein the formula 2 is represented by the following formula 2-1: 【Chemistry 9】 In the formula 2-1, the definitions of R1, m, D, n, and R3 to R11 are the same as those in the formula 2.

6. 2. The organic light-emitting device according to claim 1, wherein Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

7. The organic light-emitting device according to claim 1 , wherein L 1 and L 2 are the same or different and each independently represents a direct bond; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group.

8. The organic light-emitting device according to claim 1 , wherein X1 to X3 are N.

9. The organic light emitting device according to claim 1, wherein R1 to R11, except for A, are the same or different and each independently represents hydrogen or deuterium.

10. The organic light emitting device according to claim 1 , wherein the compound represented by Chemical Formula 2 contains at least one deuterium atom.

11. The organic light-emitting device according to claim 1 , wherein the compound represented by Chemical Formula 1 is any one of the following compounds: 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】

12. The organic light-emitting device according to claim 1 , wherein the compound represented by Chemical Formula 2 is any one of the following compounds: 【Chemistry 14】

13. The organic light emitting device according to claim 1 , wherein the first organic layer is located between the second organic layer and the cathode.

14. The organic light emitting device according to claim 1 , wherein the first organic layer is an electron transport layer, an electron injection layer, or an electron transport and injection layer.

15. The organic light emitting device according to claim 13 or 14, wherein a hole blocking layer is located between the first organic layer and the second organic layer.

16. The organic light emitting device according to claim 1 , wherein the second organic layer is a light emitting layer.

17. The organic light emitting device according to claim 16, wherein the light emitting layer comprises the compound represented by Chemical Formula 2 as a host and further comprises a dopant.

18. 2. The organic light-emitting device according to claim 1, further comprising one or more organic layers between the anode and the cathode, the organic layers including one or more of a hole transport layer, a hole injection layer, a hole transport and injection layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, and a hole blocking layer.

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