Organic light-emitting diodes

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] This application relates to an organic light-emitting element. This application claims the benefit as of the filing date of Korean Patent Application No. 10-2022-0093438, filed with the Korean Intellectual Property Office on 27 July 2022, and all its contents are incorporated herein by reference. [Background technology]

[0002] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices that utilize organic light emission typically have a structure that includes a positive electrode, a negative electrode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made up of different materials to improve the efficiency and safety of the organic light-emitting device, and can consist of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in such an organic light-emitting device, holes are injected from the positive electrode and electrons are injected from the negative electrode into the organic layer. When the injected holes and electrons combine, excitons are formed, and when these excitons fall to the floor state, light is generated.

[0003] There is a continuing demand for the development of new materials for organic light-emitting devices as described above. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Korean Published Patent Document No. 10-2017-0036641 [Overview of the project] [Problems that the invention aims to solve]

[0005] This application aims to provide an organic light-emitting element. [Means for solving the problem]

[0006] One embodiment of the present invention provides an organic light-emitting element comprising an anode; a cathode; and a first organic layer and a second organic layer provided between the anode and the cathode, wherein the first organic layer comprises a compound represented by the following chemical formula 1, and the second organic layer comprises a compound represented by the following chemical formula 2.

[0007] [ka] In the aforementioned chemical formula 1, Ar1 and Ar2 are either identical or different from each other, and independently of each other, are hydrogen; deuterium; or a substituted or unsubstituted aryl group. L1 and L2 are identical or different from each other, and independently, directly bonded; or substituted or unsubstituted arylene groups. X1 to X3 are either identical or different from each other, and each is independent of N; or CR. At least one of X1 to X3 is N, Ra, Rb, and R are either identical or different from each other, and each is independently a hydrogen atom; a deuterium atom; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. a is an integer from 0 to 6, and if a is 2 or greater, then Ra values ​​of 2 or greater are either identical or different from each other. b is an integer from 0 to 8, and if b is 2 or greater, then Rb values ​​of 2 or greater are either identical or different from each other. [ka] In the aforementioned chemical formula 2, R1 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. m is an integer from 0 to 9, and if m is 2 or greater, then R1 values ​​greater than or equal to 2 are either identical or different from each other. D is deuterium, and n is an integer from 0 to 8. R2 to R6 are either identical or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or formula A below. At least one of R2 and R6 is the following chemical formula A:

Chemical formula

Advantages of the Invention

[0008] The organic light-emitting device described in this specification includes 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, thereby achieving the effects of low driving voltage, high efficiency, and / or long lifespan.

Brief Description of the Drawings

[0009] [Figure 1] An example 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 is shown. [Figure 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 sequentially stacked is shown. [Figure 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 sequentially stacked is shown.

Modes for Carrying Out the Invention

[0010] Hereinafter, the present invention will be described in more detail.

[0011] In this specification, when a part "includes" a component, this means that, unless otherwise stated, it may include other components rather than excluding them.

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

[0013] In this specification, the dotted line (---) indicates the position where a chemical formula or compound is bonded.

[0014] In this specification, the deuterium substitution rate of a compound is determined by either calculating the substitution rate 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 by quantitative analysis using NMR, by adding DMF as an internal standard. 1 This can be determined by using the integration ratio on the 1H NMR spectrum and calculating the D-substitution rate from the integrated amount of the total peaks.

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

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

[0017] In this specification, bandgap refers to the difference in energy levels between HOMO and LUMO, i.e., the HOMO-LUMO gap.

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

[0019] Examples of substituents described herein are, but are not limited to, those described below.

[0020] The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The substitution location is not limited to any position where a hydrogen atom can be substituted, i.e., any position where a substituent can be substituted. If two or more substituents are substituted, the two or more substituents may be identical or different.

[0021] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium; halogen groups; cyano groups; alkyl groups; cycloalkyl groups; aryl groups; and heterocycles; substituted with substituents in which two or more substituents from the exemplified substituents are linked; or having no substituents at all.

[0022] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of alkyl groups; aryl groups; and heterocycles, or substituted with substituents in which two or more substituents from the exemplified substituents are linked together, or having no substituents at all.

[0023] Examples of the substituents mentioned above are described below, but are not limited to them.

[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. In one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. In another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. In yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of alkyl groups include, but are not limited to, methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n-hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, etc.

[0026] In the present invention, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. In one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include, but are not limited to, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, and cyclooctyl group.

[0027] In the present invention, the aryl group is not particularly limited, but it is preferably one having 6 to 60 carbon atoms, and may be a monocyclic aryl or a polycyclic aryl. In one embodiment, the number of carbon atoms in the aryl is 6 to 30. In another embodiment, the number of carbon atoms in the aryl is 6 to 20. Examples of monocyclic aryl groups include, but are not limited to, phenyl groups, biphenyl groups, terphenyl groups, quaterphenyl groups, etc. Examples of polycyclic aryl groups include, but are not limited to, naphthyl groups, anthracenyl groups, phenanthryl groups, pyrenyl groups, perilenyl groups, chrysenyl groups, fluorenyl groups, triperenyl groups, etc.

[0028] In the present invention, the fluorenyl group may be substituted, or two substituents may bond 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] It can be a substituted fluorenyl group, such as (9,9-diphenylfluorenyl group), but is not limited to this.

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

[0031] In this specification, the description of heterocyclic groups described above may apply to heteroaryl groups, except that they are aromatic.

[0032] In this specification, the description of aryl groups described above may apply to arylene groups, except that they are divalent groups. Examples include phenylene groups, naphthylene groups, biphenylene groups, fluorenylene groups, phenanthrylene groups, terphenylene groups, anthracenylene groups, and pyrenylene groups.

[0033] In this specification, the above-mentioned description of heterocyclic groups may apply to divalent heterocyclic groups, except that they are divalent.

[0034] In this specification, the above-mentioned description of aryl groups may apply to n+1 valent aryl groups, except that they are n+1 valent.

[0035] In this specification, the above-mentioned description of heterocyclic groups may apply to n+1 valent heterocyclic groups, except that they are n+1 valent.

[0036] In this specification, a substituted or unsubstituted ring is formed by the bonding of adjacent groups to each other, where “ring” means a hydrocarbon ring; or a heterocycle.

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

[0038] In this specification, the meaning of bonding with adjacent groups to form a ring means bonding with adjacent groups to form 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 fused ring thereof. The hydrocarbon ring means a ring consisting only of 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, an aliphatic hydrocarbon ring means a non-aromatic ring consisting only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings 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, an aromatic hydrocarbon ring means an aromatic ring consisting only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include, but are not limited to, benzene, naphthalene, anthracene, phenanthrene, perylene, fluorantene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, and spirofluorene. In this specification, an aromatic hydrocarbon ring may be interpreted as having the same meaning as an aryl group.

[0041] In this specification, an aliphatic heterocycle means 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] In this specification, an aromatic heterocycle means an aromatic ring containing 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, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, acridine, phenanthidine, diazanaphthalene, triazaidene, indole, indidine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, phenanthidine, indolocarbazole, and indenocarbazole.

[0043] Preferred embodiments of the present invention will be described in detail below. However, embodiments of the present invention can 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 element 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] The following is a detailed explanation of chemical formula 1.

[0046] [ka]

[0047] In the aforementioned chemical formula 1, Ar1 and Ar2 are either identical or different from each other, and independently of each other, are hydrogen; deuterium; or a substituted or unsubstituted aryl group. L1 and L2 are identical or different from each other, and independently, directly bonded; or substituted or unsubstituted arylene groups. X1 to X3 are either identical or different from each other, and each is independent of N; or CR. At least one of X1 to X3 is N, Ra, Rb, and R are either identical or different from each other, and each is independently a hydrogen atom; a deuterium atom; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. a is an integer from 0 to 6, and if a is 2 or greater, then Ra values ​​of 2 or greater are either identical or different from each other. b is an integer between 0 and 8, and if b is 2 or greater, then Rb values ​​of 2 or greater are either identical or different from each other.

[0048] In one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are independently 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 identical or different from each other and are independently 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 identical or different from each other and are independently 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 identical or different from each other, and are independently hydrogen; deuterium; or deuterium-substituted or unsubstituted aryl groups.

[0052] In one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other, and are independently hydrogen; deuterium; or deuterium-substituted or unsubstituted aryl groups having 6 to 60 carbon atoms.

[0053] In one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other, and are independently hydrogen; deuterium; or deuterium-substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0054] In one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other, and are independently hydrogen; deuterium; or deuterium-substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.

[0055] In one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other, and are independently substituted or unsubstituted aryl groups.

[0056] In one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other, and are independently substituted or unsubstituted aryl groups having 6 to 60 carbon atoms.

[0057] In one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other, and are independently substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0058] In one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other, and are independently substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.

[0059] In one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are independently 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 phenantrenyl group; or a substituted or unsubstituted fluorenyl group.

[0060] In one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are independently 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 identical or different from each other and are independently 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 from each other and are independently 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 identical or different from each other and are independently 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, wherein 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 from each other and are independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group, wherein 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 from each other and are independently 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, wherein 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 from each other and are independently a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; or a deuterium-substituted or unsubstituted naphthyl group, wherein 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 identical or different from each other and are independently a phenyl group; a biphenyl group; or a naphthyl group, wherein at least one of Ar1 and Ar2 is a phenyl group.

[0068] In one embodiment of the present invention, L1 and L2 are identical or different from each other, and independently, directly bonded; or substituted or unsubstituted arylene groups.

[0069] In one embodiment of the present invention, L1 and L2 are identical or different from each other, and independently, directly bonded; or substituted or unsubstituted, carbon-6 to carbon-60 arylene groups.

[0070] In one embodiment of the present invention, L1 and L2 are identical or different from each other, and independently, directly bonded; or substituted or unsubstituted, carbon-6 to carbon-30 arylene groups.

[0071] In one embodiment of the present invention, L1 and L2 are identical or different from each other, and independently, directly bonded; or substituted or unsubstituted, carbon-6 to carbon-20 arylene groups.

[0072] In one embodiment of the present invention, L1 and L2 are identical or different from each other and are independently directly bonded; 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 identical or different from each other and are independently directly bonded; 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 identical or different from each other and are independently directly bonded; substituted or unsubstituted phenylene groups; or substituted or unsubstituted biphenylene groups.

[0075] In one embodiment of the present invention, L1 and L2 are identical or different from each other and independently directly bonded; 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 identical or different from each other and independently of each other, being directly bonded; a phenylene group; or a biphenylene group.

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

[0078] In one embodiment of the present 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 directly bonded; 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 present invention, L1 is a phenylene group; or a biphenylene group.

[0082] In one embodiment of the present invention, L2 is a directly bonded, or substituted or unsubstituted phenylene group.

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

[0084] In one embodiment of the present invention, L2 is a directly bonded; or a phenylene group substituted or unsubstituted with deuterium.

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

[0086] In one embodiment of the present 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 this 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 present invention, X1 is N, and X2 and X3 are CR.

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

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

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

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

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

[0097] In one embodiment of the present invention, Ra, Rb, and R are identical or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted C1-C60 alkyl group; or a substituted or unsubstituted C6-C60 aryl group.

[0098] In one embodiment of the present invention, Ra, Rb, and R are identical or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted C1-C30 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

[0099] In one embodiment of the present invention, Ra, Rb, and R are identical or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted C1-C20 alkyl group; or a substituted or unsubstituted C6-C20 aryl group.

[0100] In one embodiment of the present invention, Ra, Rb, and R are identical or different from each other and are 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 identical or different from each other and are independently hydrogen; deuterium; a C1-C60 alkyl group substituted or unsubstituted with deuterium; or a C6-C60 aryl group substituted or unsubstituted with deuterium.

[0102] In one embodiment of the present invention, Ra, Rb, and R are the same or different from each other and are independently hydrogen; deuterium; a C1-C30 alkyl group substituted or unsubstituted with deuterium; or a C6-C30 aryl group substituted or unsubstituted with deuterium.

[0103] In one embodiment of the present invention, Ra, Rb, and R are identical or different from each other and are independently hydrogen; deuterium; a C1-C20 alkyl group substituted or unsubstituted with deuterium; or a C6-C20 aryl group substituted or unsubstituted with deuterium.

[0104] In one embodiment of the present invention, Ra, Rb, and R are identical or different from each other and are independently hydrogen; deuterium; a C1-C10 alkyl group substituted or unsubstituted with deuterium; or a C6-C20 aryl group substituted or unsubstituted with deuterium.

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

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

[0107] In one embodiment of the present invention, a is an integer from 0 to 6, and if a is 2 or greater, then Ra values ​​of 2 or greater are either the same or different from each other. In one embodiment of the present invention, a is an integer from 0 to 6. In one embodiment of the present invention, a is an integer from 1 to 6. In one embodiment of the present invention, a is 6. In one embodiment of the present invention, a is 5. In one embodiment of the present invention, a is 4. In one embodiment of the present invention, a is 3. In one embodiment of the present invention, a is 2. In one embodiment of the present invention, a is 1. In one embodiment of the present invention, a is 0.

[0108] In one embodiment of this specification, b is an integer from 0 to 8, and if b is 2 or greater, then 2 or more Rb are identical or different from each other. In one embodiment of the present invention, b is an integer from 0 to 8. In one embodiment of the present invention, b is an integer from 1 to 8. In one embodiment of the present invention, b is 8. In one embodiment of the present invention, b is 7. In one embodiment of the present invention, b is 6. In one embodiment of the present invention, b is 5. In one embodiment of the present invention, b is 4. In one embodiment of the present invention, b is 3. In one embodiment of the present invention, b is 2. In one embodiment of the present invention, b is 1. In one embodiment of the present invention, b is 0.

[0109] In one embodiment of the present invention, the 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-X3, Ra, Rb, a, and b are the same as those in Chemical Formula 1 above.

[0112] In one embodiment of this specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-A to 1-D.

[0113] [ka] [ka]

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

[0115] In one embodiment of this specification, the chemical formula 1 is represented by the following chemical formula 1-1-1.

[0116] [ka]

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

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

[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 yet another embodiment, the compound represented by chemical formula 1 contains 60% to 80% deuterium. In yet another embodiment, the compound represented by chemical formula 1 contains 80% to 100% deuterium.

[0120] In one embodiment of the present invention, the chemical formula 1 is represented by any one of the following compounds.

[0121] [ka]

[0122] [ka]

[0123] [ka]

[0124] [ka]

[0125] The following provides a detailed explanation of chemical formula 2. [ka]

[0126] In the aforementioned chemical formula 2, R1 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. m is an integer from 0 to 9, and if m is 2 or greater, then R1 values ​​greater than or equal to 2 are either identical or different from each other. D is deuterium, and n is an integer from 0 to 8. R2 to R6 are either identical or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or formula A below. At least one of R2 and R6 has the following chemical formula A: [ka] In the aforementioned chemical formula A, R7~R11 are either identical or different from each other, and each is independently a hydrogen atom; a deuterium atom; 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 (---) indicate the parts that connect to chemical formula 2.

[0127] In one embodiment of the present invention, R1 is hydrogen; deuterium; a substituted or unsubstituted C1-C60 alkyl group; or a substituted or unsubstituted C6-C60 aryl group.

[0128] In one embodiment of the present invention, R1 is hydrogen; deuterium; a substituted or unsubstituted C1-C30 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

[0129] In one embodiment of the present invention, R1 is hydrogen; deuterium; a substituted or unsubstituted C1-C20 alkyl group; or a substituted or unsubstituted C6-C20 aryl group.

[0130] In one embodiment of the present 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; a C1-C60 alkyl group substituted or unsubstituted with deuterium; or a C6-C60 aryl group substituted or unsubstituted with deuterium.

[0132] In one embodiment of the present invention, R1 is hydrogen; deuterium; a C1-C30 alkyl group substituted or unsubstituted with deuterium; or a C6-C30 aryl group substituted or unsubstituted with deuterium.

[0133] In one embodiment of the present invention, R1 is hydrogen; deuterium; a C1-C20 alkyl group substituted or unsubstituted with deuterium; or a C6-C20 aryl group substituted or unsubstituted 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 from 0 to 9. In one embodiment of the present invention, m is an integer from 1 to 9. In one embodiment of the present invention, m is 0. In one embodiment of the present invention, m is 1. In one embodiment of the present invention, m is 2. In one embodiment of the present invention, m is 3. In one embodiment of the present invention, m is 4. In one embodiment of the present invention, m is 5. In one embodiment of the present invention, m is 6. In one embodiment of the present invention, m is 7. In one embodiment of the present invention, m is 8. In one embodiment of the present invention, m is 9.

[0136] In one embodiment of the present invention, m is 9 and R1 is entirely deuterium. In one embodiment of the present invention, m is 9, and 8 of the 9 R1 atoms are deuterium. In one embodiment of the present invention, m is 9, and 7 of the 9 R1 atoms are deuterium. In one embodiment of the present invention, m is 9, and 6 of the 9 R1 atoms are deuterium. In one embodiment of the present invention, m is 9, and 5 of the 9 R1 atoms are deuterium. In one embodiment of the present invention, m is 9, and 4 of the 9 R1 atoms are deuterium. In one embodiment of the present invention, m is 9, and 3 of the 9 R1 atoms are deuterium. In one embodiment of the present invention, m is 9, and two of the nine R1 atoms are deuterium. In one embodiment of the present invention, m is 9, and one of the nine R1 atoms is deuterium.

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

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

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

[0140] In one embodiment of the present invention, R2 to R6 are the same or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; or the following formula A.

[0141] In one embodiment of the present invention, R2 to R6 are the same or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted C1 to C30 alkyl group; or the following formula A.

[0142] In one embodiment of the present invention, R2 to R6 are the same or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; or the following formula A.

[0143] In one embodiment of the present invention, R2 to R6 are the same or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted C1 to C10 alkyl group; or the following formula A.

[0144] In one embodiment of the present invention, R2 to R6 are the same or different from each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted alkyl group; or the following formula A.

[0145] In one embodiment of the present invention, R2 to R6 are the same or different from each other and are independently hydrogen; deuterium; a C1 to C60 alkyl group substituted or unsubstituted with deuterium; or the following formula A.

[0146] In one embodiment of the present invention, R2 to R6 are the same or different from each other and are independently hydrogen; deuterium; a C1 to C30 alkyl group substituted or unsubstituted with deuterium; or the following formula A.

[0147] In one embodiment of the present invention, R2 to R6 are the same or different from each other and are independently hydrogen; deuterium; a C1 to C20 alkyl group substituted or unsubstituted with deuterium; or the following formula A.

[0148] In one embodiment of the present invention, R2 to R6 are the same or different from each other and are independently hydrogen; deuterium; a C1 to C10 alkyl group substituted or unsubstituted with deuterium; or the following formula A.

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

[0150] In one embodiment of the present invention, at least one of R2 and R6 is given by the following formula A.

[0151] In one embodiment of the present invention, one of R2 and R6 is given by the following formula A.

[0152] In one embodiment of the present invention, R2 is given by the following formula A.

[0153] In one embodiment of the present invention, R6 is given by the following formula A.

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

[0155] In one embodiment of the present invention, R2 is of the following formula A, and R3 to R6 are identical or different from each other, and each is independently hydrogen; or deuterium.

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

[0157] In one embodiment of the present invention, R6 is of the following formula A, and R2 to R5 are identical or different from each other, and each is independently hydrogen; or deuterium.

[0158] [ka] In the aforementioned chemical formula A, R7~R11 are either identical or different from each other, and each is independently a hydrogen atom; a deuterium atom; 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 (---) indicate the sites where chemical formula 2 is bonded.

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

[0161] In one embodiment of the present invention, R7 to R11 are identical or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted C1-C60 alkyl group; or a substituted or unsubstituted C6-C60 aryl group, or bonded to adjacent groups to form a substituted or unsubstituted ring.

[0162] In one embodiment of the present invention, R7 to R11 are identical or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted C1-C30 alkyl group; or a substituted or unsubstituted C6-C30 aryl group, or bonded to adjacent groups to form a substituted or unsubstituted ring.

[0163] In one embodiment of the present invention, R7 to R11 are identical or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted C1-C20 alkyl group; or a substituted or unsubstituted C6-C20 aryl group, or bonded to adjacent groups to form a substituted or unsubstituted ring.

[0164] In one embodiment of the present invention, R7 to R11 are identical or different from each other, and each is independently a hydrogen; deuterium; a deuterium-substituted or unsubstituted alkyl group; or a deuterium-substituted or unsubstituted aryl group, or bonded to adjacent groups to form a substituted or unsubstituted ring.

[0165] In one embodiment of the present invention, R7 to R11 are identical or different from each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted C1-C60 alkyl group; or a deuterium-substituted or unsubstituted C6-C60 aryl group, or bonded to adjacent groups to form a deuterium-substituted or unsubstituted ring.

[0166] In one embodiment of the present invention, R7 to R11 are identical or different from each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted C1-C30 alkyl group; or a deuterium-substituted or unsubstituted C6-C30 aryl group, or bonded to adjacent groups to form a deuterium-substituted or unsubstituted ring.

[0167] In one embodiment of the present invention, R7 to R11 are identical or different from each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted C1-C20 alkyl group; or a deuterium-substituted or unsubstituted C6-C20 aryl group, or bonded to adjacent groups to form a deuterium-substituted or unsubstituted ring.

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

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

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

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

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

[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 yet another embodiment, the compound represented by chemical formula 2 contains 60% to 80% deuterium. In yet another embodiment, the compound represented by chemical formula 2 contains 80% to 100% deuterium.

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

[0175] [ka]

[0176] Compounds represented by chemical formulas 1 and 2 according to one embodiment of the present invention may have their core structures manufactured by the method described in the production example below. Substituents may be attached by methods known in the art, and the type, position, or number of substituents may be modified by techniques known in the art.

[0177] In the present invention, compounds having diverse energy band gaps can be synthesized by incorporating diverse substituents into the core structures of the compounds represented by chemical formulas 1 and 2. Furthermore, in this specification, the HOMO and LUMO energy levels of the compounds can also be adjusted by incorporating diverse substituents into the core structures of the aforementioned structures.

[0178] The following explains organic light-emitting devices.

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

[0180] In this specification, when a part is said to "include" a component, it means that, unless otherwise stated to the contrary, it may include other components rather than excluding them.

[0181] The organic light-emitting element according to the present invention comprises an anode; a cathode; a first organic layer and a second organic layer provided between the anode and the cathode, wherein the first organic layer contains a compound represented by the following chemical formula 1, and the second organic layer contains a compound represented by the following chemical formula 2.

[0182] The organic light-emitting element of the present invention can be manufactured by conventional methods and materials for manufacturing organic light-emitting elements, except that an organic layer is formed using the compound represented by chemical formula 1 and the compound represented by chemical formula 2 described above.

[0183] The aforementioned compound may be formed on the organic layer during the manufacture of the organic light-emitting element not only by vacuum deposition but also by a solution coating method. Here, the solution coating method includes, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spray coating, and roll coating.

[0184] The organic layer of the organic light-emitting element of the present invention may have a single-layer structure, or it may have a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure in which the organic layer includes one or more layers: a hole injection layer, a hole transport layer, an electron barrier layer, an emitting layer, a hole injection and transport layer, an electron transport layer, an electron injection layer, a hole barrier layer, and an electron transport and injection layer. However, the structure of the organic light-emitting element described herein is not limited thereto and may include fewer or more 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, electron injection layer, or electron transport and injection layer may contain the 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 the chemical formula 2.

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

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

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

[0191] In one embodiment of the present invention, the thickness of 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 is 10 Å to 600 Å, preferably 50 Å to 500 Å, and more preferably 200 Å to 400 Å.

[0192] In one 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 described above.

[0193] In one 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 described above.

[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 necessarily have to be 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 an organic light-emitting element according to one embodiment of the present invention, the light-emitting layer further comprises a fluorescent dopant or a phosphorescent dopant. In this case, the dopant in the light-emitting layer is included in an amount of 1 to 50 parts by weight per 100 parts by weight of the host.

[0199] In this case, the dopant may be a phosphorescent substance such as (4,6-F2ppy)2Irpic, or a fluorescent substance such as spiro-DPVBi, spiro-6P, distylbenzene (DSB), distylyl arylene (DSA), PFO-based polymers, PPV-based polymers, anthracene-based compounds, pyrene-based compounds, or boron-based compounds, but is not limited to these.

[0200] In one embodiment of the present invention, the organic light-emitting element includes an anode; a cathode; and two or more organic layers provided between the anode and the cathode, wherein 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 selected from the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron-blocking layer.

[0202] In one embodiment of the present invention, the two or more organic layers may be selected from the group consisting of an emissive layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron adjustment 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 this 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 in each of the two or more electron transport layers.

[0204] Furthermore, in one embodiment of the present invention, if the compound is included in each of the two or more electron transport layers, the other materials, excluding the compound represented by chemical formula 1 and the compound represented by chemical formula 2, may be the same or different from each other.

[0205] If 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, electron injection layer, or 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). In one example, the total weight ratio of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 to the n-type dopant may be 2:8 to 8:2, for example, 4:6 to 6:4.

[0206] For example, the compounds represented by chemical formula 1 and chemical formula 2 may be present in a total weight ratio of 1:1 to the n-type dopant.

[0207] An organic light-emitting element according to one embodiment of the present invention further comprises one or more organic layers between the anode and the cathode, wherein the organic layers may further include one or more layers of hole transport, hole injection, hole transport and injection, electron barrier, light-emitting layer, electron transport layer, electron injection layer, electron transport and injection layer, and hole barrier layer.

[0208] An organic light-emitting element according to one embodiment of the present invention may further include one or more light-emitting layers.

[0209] An organic light-emitting element according to one 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 contain the host compound described above.

[0210] An organic light-emitting element according to one embodiment of the present invention further includes one or more light-emitting layers in addition to the aforementioned light-emitting layer, and each light-emitting layer further includes a fluorescent dopant or a phosphorescent dopant. In this case, the dopant in the light-emitting layer is included in an amount of 1 to 50 parts by weight per 100 parts by weight of the host.

[0211] An organic light-emitting element according to one embodiment of the present invention may include two or more light-emitting layers.

[0212] An organic light-emitting element 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] An organic light-emitting element according to one embodiment of the present invention may include three or more light-emitting layers.

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

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

[0216] An organic light-emitting element 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 element according to one embodiment of the present invention includes three or more light-emitting layers, wherein the maximum emission peak of one light-emitting layer (light-emitting layer 1) is 400 nm to 500 nm, the maximum emission peak of another light-emitting layer (light-emitting layer 2) can be 510 nm to 580 nm or 610 nm to 680 nm, and the maximum emission peak of another light-emitting layer (light-emitting layer 3) can be 400 nm to 500 nm.

[0218] Furthermore, 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 perpendicular to the direction from the anode to the cathode. In this case, all three or more light-emitting layers may be blue fluorescent light-emitting layers.

[0220] In an organic light-emitting element according to one embodiment of the present invention, if the organic light-emitting element 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 layers of hole transport layer, hole injection layer, hole transport and injection layer, electron barrier layer, charge generation layer, light-emitting layer, electron transport layer, electron injection layer, electron transport and injection layer, and hole barrier layer.

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

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

[0223] The organic light-emitting element may have, for example, a stacked structure as shown below, but is not limited to this. (1) Anode / Hole transport layer / Emitting layer / Cathode (2) Anode / Hole injection layer / Hole transport layer / Emitting layer / Cathode (3) Anode / Hole injection layer / Hole buffer layer / Hole transport layer / Emission layer / Cathode (4) Anode / Hole transport layer / Emitting layer / Electron transport layer / Cathode (5) Anode / Hole transport layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode (6) Anode / Hole injection layer / Hole transport layer / Emitting layer / Electron transport layer / Cathode (7) Anode / Hole injection layer / Hole transport layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode (8) Anode / Hole injection layer / Hole buffer layer / Hole transport layer / Emitting layer / Electron transport layer / Cathode (9) Anode / Hole injection layer / Hole buffer layer / Hole transport layer / 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 structure as shown in FIGS. 1 to 3, but is not limited thereto.

[0225] FIG. 1 illustrates the 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 such a 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] FIG. 2 illustrates the 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, 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 sequentially stacked. In such a 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 light emitting layer 6.

[0227] Figure 3 illustrates the structure of an organic light-emitting element in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron barrier layer 5, a light-emitting layer 6, a hole barrier layer 7, an electron injection and transport layer 11, and a cathode 10 are sequentially stacked. In such a 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 light-emitting layer 6.

[0228] According to one embodiment of the present invention, the organic light-emitting element may be a tandem structure in which two or more independent elements are connected in series. In one embodiment, the tandem structure may be in a form in which each organic light-emitting element is joined to a charge generation layer. Since the elements in the tandem structure can be driven with a lower current than the unit elements with respect to the same brightness, there is an advantage in that the lifespan characteristics of the elements 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 arranged adjacent to each other. For example, the electron transport layer and the light-emitting layer may be arranged physically adjacent to each other.

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

[0232] The organic light-emitting element of the present invention may be manufactured using materials and methods known in the art, except that one or more layers of the organic material layer contain the aforementioned compounds, i.e., the compound represented by chemical formula 1 and the compound represented by chemical formula 2.

[0233] If the organic light-emitting element includes multiple organic layers, the organic layers may be formed from the same substance or different substances.

[0234] For example, the organic light-emitting element according to this specification can be manufactured by depositing a metal or a conductive metal oxide or an alloy thereof onto a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode, then forming an organic layer on top of the anode that includes a hole injection layer, a hole transport layer, an emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer, and finally depositing a material that can be used as a cathode on top of that. In addition to this method, the organic light-emitting element may also be manufactured by sequentially depositing the cathode material, the organic layer, and the anode material onto a substrate.

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

[0236] The organic layer may be a multilayer structure including a hole injection layer, a hole transport layer, an electron barrier layer, an emissive layer, a hole barrier layer, an electron transport layer, an electron injection layer, or an electron transport and injection layer, but is not limited to this, and may be a single-layer structure. Furthermore, the organic layer may be manufactured in fewer layers using a variety of polymer materials by a solvent process other than vapor deposition, such as spin coating, dip coating, doctor bladeding, screen printing, inkjet printing, or thermal transfer.

[0237] The anode is an electrode into which holes are injected, and as the anode material, a material with a large work function is preferred so that hole injection into the organic layer is smooth. Specific examples of anode materials used in the present invention include, but are not limited to, metals or alloys thereof such as vanadium, chromium, copper, zinc, and gold; 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 into which electrons are injected, and the cathode material is preferably a material with a small work function so that electron injection into the organic layer is easily facilitated. Specific examples of cathode materials include, but are not limited to, metals or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; and multilayer materials 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. The hole injection material is preferably a material that allows for smooth injection of holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, the aforementioned compounds or metal porphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile-hexazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and polyaniline and polythiophene-based conductive polymers.

[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, there is the advantage that a decrease in hole injection characteristics can be prevented, and when it is 150 Å or less, there is the advantage that the drive voltage can be prevented from being increased in order to improve hole movement due to the hole injection layer being too thick.

[0241] In one embodiment of the present invention, the hole-injecting material may include an arylamine compound containing a carbazole group and a tetrafluorobenzonitrile compound. For example, the amine compound is represented as Het101-L101-N(Ar101)(Ar102), where Het101 is a substituted or unsubstituted carbazole group, L101 is a directly bonded or substituted or unsubstituted arylene group, and Ar101 and Ar102 may be identical or different from each other, and each may be independently a substituted or unsubstituted aryl group. The amine compound and the tetrafluorobenzonitrile compound may be included in an appropriate molar ratio, for 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 play a role in facilitating the smooth 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 a high mobility for holes, is suitable. Specific examples include the aforementioned compounds or arylamine-based organic substances, conductive polymers, and block copolymers in which a conjugated part and a non-conjugated part are together, but are not limited to these only. In one embodiment of the present specification, the hole transport material may include an arylamine-based compound containing a carbazole group.

[0243] A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, and may include the aforementioned compounds 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 aforementioned compounds or materials known in the art may be used for the electron blocking layer. Specifically, in one embodiment of the present invention, the electron blocking material may include an arylamine-based compound containing a phenanthrenyl group, but is not limited thereto.

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

[0246] Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocycle-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluorantene compounds, while heterocycle-containing compounds include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives.

[0247] When the luminescent layer emits red light, phosphorescent substances such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum), or fluorescent substances such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the luminescent dopant, but are not limited to these. When the luminescent layer emits green light, phosphorescent substances such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium), or fluorescent substances such as Alq3(tris(8-hydroxyquinolino)aluminum), anthracene compounds, pyrene compounds, and boron compounds may be used as the luminescent dopant, but are not limited to these. When the light-emitting layer emits blue light, the light-emitting dopant may be a phosphorescent substance such as (4,6-F2ppy)2Irpic, or a fluorescent substance such as spiro-DPVBi, spiro-6P, distylbenzene (DSB), distylyl arylene (DSA), PFO-based polymers, PPV-based polymers, anthracene-based compounds, pyrene-based compounds, or boron-based compounds, but is not limited to these.

[0248] In one embodiment of the present invention, the luminescent layer material may be a compound according to chemical formula 2 of this application, an anthracene compound, or a boron compound.

[0249] A hole-blocking layer may be provided between the electron transport layer and the light-emitting layer. This hole-blocking layer prevents holes from reaching the cathode and may generally be formed under the same conditions as the hole-injection layer. Specifically, examples 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 substance may include a compound represented by the following chemical formula HB.

[0251] [ka] In the aforementioned chemical formula HB, L is a directly bonded; substituted or unsubstituted arylene group; substituted or unsubstituted alkylene group; substituted or unsubstituted divalent alkoxy group; substituted or unsubstituted divalent alkenyl group; or 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~R13 are either identical or different from each other, and each is independently of the following: hydrogen; deuterium; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amide group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryloxy group; substituted or unsubstituted alkylthiooxy group; substituted or unsubstituted arylthiooxy group; substituted or unsubstituted alkylsulfoxy group; substituted or unsubstituted arylsulfoxy group; substituted or unsubstituted alkenyl group; substituted or unsubstituted silyl group; substituted or unsubstituted boron group; substituted or unsubstituted amine group; substituted or unsubstituted arylphosphine group; substituted or unsubstituted phosphine oxide group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group. Ar3 and Ar4 are either identical or different from each other and are independently 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 directly bonded group; 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 directly bonded; 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 directly bonded, or substituted or unsubstituted arylene group.

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

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

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

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

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

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

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

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

[0263] According to one embodiment of the present invention, R11 to R13 are identical or different from each other and are independently 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 identical or different from each other and are independently 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 identical or different from each other and are independently 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 identical or different from each other and are independently 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 identical or different from each other and are independently 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 identical or different from each other and are independently 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 identical or different from each other and are independently 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 identical or different from each other and are 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 formulas HB-A to HB-D.

[0274] [ka] [ka]

[0275] In the aforementioned 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 play a role in facilitating electron transport. Suitable electron transport materials are those with high electron mobility that can readily receive electrons from the cathode and transfer them to the light-emitting layer. Specific examples include, but are not limited to, the Al complex of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. 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, there is the advantage of preventing a decrease in electron transport characteristics, and when it is 500 Å or less, there is the advantage of preventing the driving voltage from increasing in order to improve electron movement due to the electron transport layer being too thick.

[0277] The electron injection layer can play a role in facilitating electron injection. Preferred electron injection materials are compounds that have the ability to transport electrons, have an excellent electron injection effect from the cathode and on the light-emitting layer or light-emitting material, prevent the movement of excitons generated in the light-emitting layer to the hole injection layer, and have excellent thin-film formation ability. Specifically, these include, but are not limited to, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0278] Examples of the aforementioned metal complex compounds include, but are not limited to, 8-hydroxyquinolina tritium, bis(8-hydroxyquinolina)zinc, bis(8-hydroxyquinolina)copper, bis(8-hydroxyquinolina)manganese, tris(8-hydroxyquinolina)aluminum, tris(2-methyl-8-hydroxyquinolina)aluminum, tris(8-hydroxyquinolina)gallium, bis(10-hydroxybenzo[h]quinolina)beryllium, bis(10-hydroxybenzo[h]quinolina)zinc, bis(2-methyl-8-quinolina)chlorogallium, bis(2-methyl-8-quinolina)(o-crezolat)gallium, bis(2-methyl-8-quinolina)(1-naphthorato)aluminum, and bis(2-methyl-8-quinolina)(2-naphthorato)gallium.

[0279] In one embodiment of the present invention, the electron injection and transport material may include a compound according to Chemical Formula 1 of the present application or a triazine compound, and may further include an n-type dopant or an organometallic compound. For 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. Depending on the material used, the organic light-emitting element according to the present invention may be a front-emitting type, a rear-emitting type, or a double-sided emitting type. [Examples]

[0280] The present invention will be described in detail below with reference to examples. However, the examples of the present invention can be modified into various other forms, and the scope of this application should not be construed as being limited to the examples detailed below. The examples of the present invention are provided to give a more complete explanation of this specification to a person of average skill in the art.

[0281] <Manufacturing Example 1> [ka]

[0282] In a 500 ml round-bottom flask under a nitrogen atmosphere, the compounds 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (5.50 g, 11.84 mmol) and 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. Then, 120 ml of 2 M potassium carbonate aqueous solution was added, followed by tetrakis-(triphenylphosphine)palladium (0.41 g, 0.36 mmol), and the mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the mixture was dried with anhydrous magnesium sulfate. After concentration under reduced pressure, the mixture was recrystallized with 320 ml of toluene to produce compound 1-1 (5.88 g, 73%). MS[M+H] + =741

[0283] <Manufacturing Example 2> [ka]

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

[0285] <Manufacturing Example 3> [ka]

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

[0287] <Manufacturing Example 4> [ka]

[0288] Compound a (6.50 g, 15.57 mmol) and 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 under a nitrogen atmosphere. Then, 120 ml of 2 M potassium carbonate aqueous solution was added, followed by tetrakis-(triphenylphosphine)palladium (0.54 g, 0.47 mmol), and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the mixture was dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the mixture was recrystallized in 320 ml of ethyl acetate to produce compound 2-1 (5.91 g, 68%). MS[M+H] + =555

[0289] <Manufacturing Example 5> [ka]

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

[0291] <Manufacturing Example 6> [ka]

[0292] Compound c (6.50 g, 15.55 mmol) and 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 under a nitrogen atmosphere. Then, 110 ml of 2 M potassium carbonate aqueous solution was added, followed by tetrakis-(triphenylphosphine)palladium (0.54 g, 0.47 mmol), and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the mixture was dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the mixture was recrystallized with 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 thin film of ITO (indium tin oxide) to a thickness of 1,000 Å was ultrasonically cleaned in distilled water containing detergent. Fischer Co. products were used as the detergent. The distilled water used was filtered twice through a Millipore Co. filter. After washing the ITO for 30 minutes, the process was repeated twice with distilled water, followed by 10 minutes of ultrasonic cleaning. After the distilled water cleaning, the substrate was ultrasonically cleaned with isopropyl alcohol, acetone, and methanol solvents, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes before being transported to a vacuum deposition chamber.

[0294] On the ITO transparent electrode prepared in this manner, compounds with the following chemical formulas [HI-1] and [HI-2] were deposited by thermal vacuum deposition to a thickness of 100 Å in a molar ratio of 98:2 to form a hole injection layer.

[0295] [ka]

[0296] A hole transport layer was formed on the aforementioned hole injection layer by vacuum deposition of the following compound [HT-1] (1150 Å), which is a material that transports holes.

[0297] [ka]

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

[0299] [ka]

[0300] Next, on the electron blocking layer, BH-1 and BD-1 as described below were vacuum-deposited at a film thickness of 200 Å and a weight ratio of 40:1 to form a light-emitting layer.

[0301]

Chemical formula

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

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

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

[0305] In the above process, the deposition rate of the organic matter was maintained at 0.4 - 0.7 Å / sec, the deposition rate of lithium fluoride for the negative electrode was 0.3 Å / sec, and that of aluminum was 2 Å / sec. The degree of vacuum during deposition was maintained at 2×10 -7 ~5×10 -6 torr to fabricate an organic light-emitting device.

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

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

[0308]

Chemical formula

[0309] Comparative Examples 13-15 An organic light-emitting element 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 16-18 An organic light-emitting element 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].

[0311] Comparative Examples 19-21 An organic light-emitting element 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 22-36 An organic light-emitting element was manufactured in the same manner as in Comparative Example 1, except that the compounds listed in Table 1 below were used instead of [ET-1] and [BH-1] in Comparative Example 1.

[0313] Comparative Examples 37-45 An organic light-emitting element 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 element produced in the above experimental examples and comparative examples was supplied with 20 mA / cm². 2 When a current of 20 mA / cm² is applied, the manufactured organic light-emitting element reacts to the current of 20 mA / cm². 2 The driving voltage, luminous efficiency, and color coordinates were measured at a current density of 20 mA / cm². 2 The time (T95) at which the brightness drops to 95% of the initial brightness was measured at the given current density. The results are shown in Table 1 below. T95 represents the time it takes for the brightness to decrease from the initial brightness (1600 nits) to 95%.

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

[0316] As shown in Table 1 above, 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, with the compounds of Chemical Formula 1 and Chemical Formula 2 being used as materials for the electron transport and injection layers 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 devices in which the compounds represented by Chemical Formula 1 and Chemical Formula 2 are used separately, when the compound of Chemical Formula 1 is used in place of ET-1 or ET-2, or when the compound of Chemical Formula 2 is 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 are used in place of the compound of chemical formula 2.

[0320] Therefore, compared to the comparative example, the organic light-emitting diodes in the experimental example basically exhibit characteristics of low voltage, high efficiency, and long lifespan. In particular, it can be confirmed that the compound of chemical formula 1 has the characteristic of high efficiency, and the compound of chemical formula 2 has the characteristic of long lifespan.

[0321] Specifically, comparing Experimental Examples 1-1 to 1-9 with Comparative Examples 16 to 21, Experimental Examples 1-1 to 1-9, which used compounds of chemical formula 1 and chemical formula 2, showed an efficiency increase of up to approximately 12% compared to Comparative Examples 16 to 21, which did not use compounds of chemical formula 1.

[0322] Furthermore, 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 used compounds of chemical formula 1 and chemical formula 2, showed a maximum lifetime increase of approximately 72% compared to Comparative Examples 13 to 15 and 22 to 36, which did not use compounds of chemical formula 2.

[0323] Comparative Examples 19-21 use compounds (ET-2) that do not contain a cyano group. Comparing Experimental Examples 1-1-1-9 with Comparative Examples 19-21, it can be confirmed that Experimental Examples 1-1-1-9, which use compounds of chemical formula 1 containing a cyano group, have a lower driving voltage, higher luminous efficiency, and longer lifespan than Comparative Examples 19-21.

[0324] Comparative Examples 22-24 use a compound (BH-2) in which a phenyl group and a dibenzofuran are linked to an anthracene core. Comparing Experimental Examples 1-1-1-9 with Comparative Examples 22-24, it can be confirmed that Experimental Examples 1-1-1-9, which use the compound of chemical formula 2 in which a naphthobenzofuran and a biphenyl group are linked to an anthracene core, have a lower driving voltage, higher luminous efficiency, and longer lifespan than Comparative Examples 22-24.

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

[0326] Comparative Examples 28-30 use a compound (BH-4) in which a biphenyl group and dibenzofuran are linked to an anthracene core. Comparing Experimental Examples 1-1 to 1-9 with Comparative Examples 28-30, it can be confirmed that Experimental Examples 1-1 to 1-9, which use the compound of chemical formula 2 in which naphthobenzofuran is linked to an anthracene core, have a lower driving voltage, higher luminous efficiency, and longer lifespan than Comparative Examples 28-30.

[0327] Comparative Examples 31-34 use a naphthobenzofuran compound (BH-5) in which the condensation position of benzene differs from that of Chemical Formula 2 of the present invention. Comparing Experimental Examples 1-1-1-9 with Comparative Examples 31-34, it can be confirmed that Experimental Examples 1-1-1-9, which use the compound of Chemical Formula 2 of the present invention, have a lower driving voltage, higher luminous efficiency, and longer lifespan than Comparative Examples 31-34, which use a naphthobenzofuran compound (BH-5) in which the condensation position of benzene differs from that of Chemical Formula 2 of the present invention.

[0328] Comparative Examples 34-36 use a compound (BH-6) in which a naphthyl group is linked to the anthracene core instead of a biphenyl group. Comparing Experimental Examples 1-1-1-9 with Comparative Examples 34-36, it can be confirmed that Experimental Examples 1-1-1-9, which use the compound of chemical formula 2 in which a biphenyl group is linked to the anthracene core, have a lower driving voltage, higher luminous efficiency, and longer lifespan than Comparative Examples 34-36.

[0329] Comparative Examples 37-39 involve using a compound (BH-7) in which a biphenyl group containing a para-phenyl group is linked to the anthracene core, instead of a biphenyl group containing an ortho-phenyl group. Comparing Experimental Examples 1-1 to 1-9 with Comparative Examples 37-39, it can be confirmed that Experimental Examples 1-1 to 1-9, which use the compound of chemical formula 2 in which a biphenyl group containing an ortho-phenyl group is linked to the anthracene core, have a lower driving voltage, higher luminous efficiency, and longer lifespan than Comparative Examples 37-39.

[0330] Comparative Examples 40-42 use a compound (BH-8) in which a phenyl group substituted with deuterium is linked to the anthracene core instead of a biphenyl group. Comparing Experimental Examples 1-1-1-9 with Comparative Examples 40-42, it can be confirmed that Experimental Examples 1-1-1-9, which use the compound of chemical formula 2 in which a biphenyl group is linked to the anthracene core, have a lower driving voltage, higher luminous efficiency, and longer lifespan than Comparative Examples 40-42.

[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 a material for the light-emitting layer, it is possible to have high efficiency characteristics while maintaining the long lifetime characteristics of the organic light-emitting device.

[0332] Although preferred embodiments of the present invention (combination experiments of electron transport and injection layers and light-emitting layers) have been described above, the present invention is not limited thereto and can be implemented in various ways within the scope of the claims and detailed description of the invention, and this also falls 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 barrier layer 6 ···Emitting layer 7 ···Hole barrier 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; Cathode; and It includes a first organic layer and a second organic layer provided between the anode and the cathode, The aforementioned first organic layer is an electron transport layer, an electron injection layer, or an electron transport and injection layer. The aforementioned second organic layer is a light-emitting layer, The first organic layer contains a compound represented by the following chemical formula 1, The second organic layer contains an organic light-emitting element represented by the following chemical formula 2-1: 【Chemistry 1】 In the aforementioned chemical formula 1, Ar1 and Ar2 are identical or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. L1 is a substituted or unsubstituted arylene group. L2 is a directly bonded, substituted, or unsubstituted arylene group. X1 to X3 are N, Ra and Rb are either identical or different from each other, and independently of each other, are hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. a is an integer from 0 to 6, and if a is 2 or greater, then Ra values ​​of 2 or greater are either identical or different from each other. b is an integer from 0 to 8, and if b is 2 or greater, then Rb values ​​of 2 or greater are either identical or different from each other. 【Chemistry 2】 In the aforementioned chemical formula 2-1, R1 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. m is an integer from 0 to 9, and if m is 2 or greater, then R1 values ​​of 2 or greater are either identical or different from each other. D is deuterium, and n is an integer from 0 to 8. R3 to R6 are either identical or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group. R7 to R11 are either identical or different from each other, and each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or adjacent substituents bond to each other to form a substituted or unsubstituted ring.

2. The organic light-emitting element according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4: 【Transformation 3】 【Chemistry 4】 In the aforementioned 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.

3. The organic light-emitting element according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-A to 1-D. 【Transformation 5】 【Transformation 6】 In the above chemical formulas 1-A to 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 element according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1-1. 【Transformation 7】 In the aforementioned 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 L1 is a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group. L2 is a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group. The organic light-emitting element according to claim 1.

6. The organic light-emitting element according to claim 1, wherein each of the R3 to R11 is independently hydrogen; or deuterium.

7. The organic light-emitting element according to claim 1, wherein the compound of chemical formula 2-1 contains at least one deuterium atom.

8. The organic light-emitting element according to claim 1, wherein the compound represented by the chemical formula 1 is one of the following compounds: 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】

9. The compound represented by the chemical formula 2-1 is one of the following compounds, according to claim 1, for the organic light-emitting element: 【Chemistry 12】

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

11. The organic light-emitting element according to claim 1 or 10, wherein a hole-blocking layer is located between the first organic layer and the second organic layer.

12. The organic light-emitting element according to claim 1, wherein the light-emitting layer contains the compound represented by chemical formula 2-1 as a host and further contains a dopant.

13. The organic light-emitting element according to claim 1, further comprising one or more organic layers between the anode and the cathode, wherein the organic layers include one or more layers of a hole transport layer, a hole injection layer, a hole transport and injection layer, an electron barrier layer, an emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, and a hole barrier layer.

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