Organic light-emitting element

Abstract

The present specification relates to an organic light-emitting element comprising: an anode; a cathode; a first organic layer provided between the anode and the cathode; and a second organic layer provided between the cathode and the first organic layer, wherein the first organic layer includes a compound represented by formula 1, and the second organic layer includes a compound represented by formula 2. A compound according to at least one embodiment in the present specification can improve efficiency, lower driving voltage, and / or improve lifespan characteristics of the organic light-emitting element.

Description

Organic light-emitting diode

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2024-0181458 filed with the Korean Intellectual Property Office on December 9, 2024, the entire contents of which are incorporated herein.

[0002] This specification relates to organic light-emitting diodes.

[0003] In this specification, an organic light-emitting device refers to a light-emitting device utilizing an organic semiconductor material, which requires the exchange of holes and / or electrons between an electrode and an organic semiconductor material. Organic light-emitting devices can be broadly classified into two types based on their operating principles as follows. The first is a light-emitting device in which excitons are formed in an organic layer by photons introduced into the device from an external light source, these excitons are separated into electrons and holes, and these electrons and holes are each transferred to different electrodes to be used as current sources (voltage sources). The second is a light-emitting device in which holes and / or electrons are injected into an organic semiconductor material layer forming an interface with the electrodes by applying voltage or current to two or more electrodes, and the device operates based on the injected electrons and holes.

[0004] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting diodes (OLEDs) that utilize this phenomenon typically have a structure comprising an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to enhance the efficiency and stability of the OLED; for example, it may consist of a hole injection layer, a hole transport layer, an emissive layer, an electron suppression layer, an electron transport layer, and an electron injection layer. In the structure of such an OLED, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall back to the ground state. Such OLEDs are known to possess characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, a wide viewing angle, and high contrast.

[0005] In order to fully exhibit the excellent characteristics of the aforementioned organic light-emitting diode, the materials forming the organic layer within the device, such as hole injection materials, hole transport materials, light-emitting materials, electron suppression materials, electron transport materials, and electron injection materials, must be supported by stable and efficient materials, so the development of new materials is continuously required.

[0006] (Patent Document 1) Korean Patent Publication No. 2000-0051826

[0007] An organic light-emitting element is described in this specification.

[0008] One embodiment of the present specification provides an organic light-emitting device comprising an anode; a cathode; a first organic layer provided between the anode and the cathode; and a second organic layer provided between the cathode and the first organic layer, 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.

[0009] [Chemical Formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] Ar1 and Ar2 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and a substituted or unsubstituted aliphatic hydrocarbon ring, and

[0013] L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0014] L2 and L3 are the same or different from each other, and each is independently directly bonded; or are substituted or unsubstituted arylene groups, and

[0015] R1 to R3 are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0016] a, b, and c are each independently integers from 0 to 3, and if a is 2 or greater, 2 or more L1s are equal to or different from each other, if b is 2 or greater, 2 or more L2s are equal to or different from each other, and if c is 2 or greater, 2 or more L3s are equal to or different from each other, and

[0017] r2 and r3 are each independently integers from 0 to 4, and if r2 is 2 or greater, 2 or more R2s are equal to or different from each other, and if r3 is 2 or greater, 2 or more R3s are equal to or different from each other, and

[0018] [Chemical Formula 2]

[0019]

[0020] In the above chemical formula 2,

[0021] Ar3 and Ar4 are the same or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0022] L4 to L6 are the same or different from one another, and each is independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0023] R4 to R7 are the same or different from one another, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0024] d, e, and f are each independently integers from 0 to 3, and if d is 2 or greater, L4 of 2 or greater is equal to or different from each other, if e is 2 or greater, L5 of 2 or greater is equal to or different from each other, and if f is 2 or greater, L6 of 2 or greater is equal to or different from each other, and

[0025] r4 and r5 are each independently integers from 0 to 4, and if r4 is 2 or greater, 2 or more R4s are equal to or different from each other, and if r5 is 2 or greater, 2 or more R5s are equal to or different from each other, and

[0026] r6 and r7 are each independently integers from 0 to 3, and if r6 is 2 or more, 2 or more R6s are the same or different from each other, and if r7 is 2 or more, 2 or more R7s are the same or different from each other.

[0027] The organic light-emitting device described in this specification comprises a compound represented by Formula 1 in the first organic layer and a compound represented by Formula 2 in the second organic layer, thereby having the effects of low driving voltage, high efficiency, and / or long lifespan.

[0028] FIG. 1 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a first organic layer (21), a second organic layer (22), and a cathode (9) are sequentially stacked.

[0029] FIG. 2 illustrates 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), a hole transport assist layer (5), a light-emitting layer (6), a hole suppression layer (7), an electron transport and injection layer (8), and a cathode (9) are sequentially stacked.

[0030] Figure 3 is an MS graph of compound A.

[0031] [Explanation of the symbol]

[0032] 1: Substrate

[0033] 2: Anode

[0034] 3: Hole injection layer

[0035] 4: Precision Transport Layer

[0036] 5: Precision Transport Auxiliary Layer

[0037] 6: Emissive layer

[0038] 7: Hole inhibition layer

[0039] 8: Electron transport and injection layer

[0040] 9: Cathode

[0041] 21: First organic layer

[0042] 22: Second organic layer

[0043] The present specification will be described in more detail below.

[0044] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0045] In this specification, when it is said that a member is located "on" another member, this includes not only cases where a member is in contact with another member, but also cases where another member exists between the two members.

[0046] In this specification, "adjacent" groups may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the atom on which the substituent is substituted, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

[0047] In this specification, "containing deuterium," "deuterated," or "deuterated" means that hydrogen at a substitutable position of a compound is substituted with deuterium. In this specification, "excessively deuterated" means a compound or group in which all hydrogens in the molecule are substituted with deuterium, and has the same meaning as "100% deuterated."

[0048] In this specification, "X% deuterated," "degree of deuteration X%," or "deuteration substitution rate X%" means that X% of the hydrogens at substitutable positions in the structure are substituted with deuteration. The "deuteration substitution rate (%)" of a compound or group may mean (number of deuterations) / (number of deuterations + number of hydrogens) * 100 (%) of the compound or group. For example, if the structure is dibenzofuran, "25% deuterated" of the dibenzofuran, "degree of deuteration 25%" of the dibenzofuran, or "deuteration substitution rate 25%" of the dibenzofuran means that 2 of the 8 hydrogens at substitutable positions of the dibenzofuran are substituted with deuteration.

[0049] In this specification, “deuteration” or “deuteration substitution rate” can be determined by known methods such as nuclear magnetic resonance spectroscopy (1H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry).

[0050] Specifically, when analyzing "deuterium" or "deuterium substitution rate" using nuclear magnetic resonance spectroscopy (1H NMR), DMF (dimethylformamide) is added as an internal standard, and the deuterium or deuterium substitution rate can be calculated from the total peak integration amount through the integration ratio on the 1H NMR.

[0051] In addition, when analyzing the "deuteration" or "deuteration rate" through TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), the substitution rate can be calculated based on the maximum value (median) of the distribution of molecular weights at the end of the reaction. For example, when analyzing the deuteration of the following compound A, the molecular weight of the following starting material is 506, and the maximum value (median) of the molecular weight of the following compound A in the MS graph of Fig. 3 is 527. Since 21 of the 26 hydrogens at substitutable positions of the following starting material were substituted with deuteration, it can be calculated that approximately 81% of the hydrogens were deuterated.

[0052]

[0053] In this specification, D means deuterium.

[0054] In this specification, [ ] Dn means that the structure inside the parentheses contains n deuterium atoms. That is, the above n represents the number of deuterium atoms substituted in the compound inside the parentheses, and n is an integer greater than or equal to 1, and the maximum value of n is equal to the number of substitutable hydrogens in the compound inside the parentheses. For example, if the number of substitutable hydrogens in the compound inside the parentheses is 46, then n is an integer from 1 to 46.

[0055] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, the site where the substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0056] In this specification, the term “substituted or unsubstituted” means substituted with one or more substituents selected from the group consisting of deuterium; halogen group; cyano group (-CN); substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; and substituted or unsubstituted heterocyclic group, or substituted with two or more of the exemplified substituents linked together, or not having any substituents.

[0057] In this specification, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of deuterium; cyano groups (-CN); alkyl groups having 1 to 10 carbon atoms; and aryl groups having 6 to 30 carbon atoms, or is substituted with two or more of the exemplified substituents connected to a substituent, or has no substituents.

[0058] In this specification, the connection of two or more substituents means that a hydrogen of one substituent is connected to another substituent. For example, the connection of two substituents means that a phenyl group and a naphthyl group are connected or It can be a substituent. In addition, the connection of three substituents includes not only the consecutive connection of (substituent 1)-(substituent 2)-(substituent 3), but also the connection of (substituent 2) and (substituent 3) to (substituent 1). For example, a phenyl group, a naphthyl group, and an isopropyl group are connected, , , or It can be a substituent. The aforementioned definition applies equally to the connection of 4 or more substituents.

[0059] Examples of the above substituents are described below, but are not limited thereto.

[0060] In this specification, examples of halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0061] In the present specification, the alkyl group may be a straight chain or a branched chain, and while the number of carbon atoms is not particularly limited, it is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of alkyl groups include, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited thereto.

[0062] In the present specification, the cycloalkyl group is not particularly limited, but it is preferable that it has 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to yet another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, adamantyl groups, etc. are used, but are not limited thereto.

[0063] In this specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The monocyclic aryl group may include two or more benzene rings. The monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group refers to a structure in which two or more benzene rings are condensed. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylene group, chrysenyl group, fluoranthenyl group, fluorenyl group, etc., but is not limited thereto.

[0064] In the present specification, the fluorenyl group may be substituted, and two substituents may combine to form a spiro structure.

[0065] When the above fluorenyl group is substituted, , Spirofluorenyl group of the back, etc. (9,9-dimethylfluorenyl group), and It can be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited to this.

[0066] In the present specification, the heteroaryl group is a ring group comprising one or more heteroatoms N, O, P, S, Si, and Se, and while the number of carbon atoms is not particularly limited, it is preferably 2 to 60 carbon atoms. The heteroaryl group may be monocyclic or polycyclic. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of heterocyclic groups include, but are not limited to, pyridine groups, pyrrole groups, pyrimidine groups, pyridazinyl groups, furan groups, thiophene groups, imidazole groups, pyrazol groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, etc.

[0067] In this specification, an arylene group refers to a divalent aryl group, and the description of the aryl group described above may be cited except for the fact that it is divalent.

[0068] In this specification, a heteroarylene group refers to a divalent heteroaryl group, and the description of the heteroaryl group described above may be cited except for the fact that it is divalent.

[0069] In the present specification, in a substituted or unsubstituted ring formed by combining with adjacent groups, "ring" means a hydrocarbon ring; or a hetero ring.

[0070] The above hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring. The description of the aryl group described above may apply to the aromatic hydrocarbon ring, and the description of the cycloalkyl group described above may apply to the aliphatic hydrocarbon ring. Furthermore, the condensed ring of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring may have a structure in which the aryl group and the cycloalkyl group described above are condensed together.

[0071] In this specification, the meaning of forming a ring by combining with adjacent groups means forming a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heteroring; a substituted or unsubstituted aromatic heteroring; or a condensed ring thereof by combining with adjacent groups. The hydrocarbon ring means a ring composed only of carbon and hydrogen atoms. The heteroring means a ring comprising one or more selected from N, O, P, S, Si, and Se. In this specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heteroring, and aromatic heteroring may be monocyclic or polycyclic.

[0072] In this specification, an aliphatic hydrocarbon ring refers to a non-aromatic ring composed 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.

[0073] In this specification, an aromatic hydrocarbon ring refers to an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include, but are not limited to, benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, 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.

[0074] 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, oxephane, azocaine, thiocane, etc.

[0075] In this specification, an aromatic heterocycle means an aromatic ring comprising one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazol, oxazole, isooxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazolin, quinoxaline, naphthiridine, acridine, phenanthridine, diazanaphthalene, driazindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, Examples include imidazopyridine, phenoxazine, indolocarbazole, indenocabazole, etc., but are not limited to these.

[0076] In this specification, "energy level" refers to the magnitude of energy. Accordingly, an energy level is interpreted as referring to the absolute value of the corresponding energy value. For example, an energy level being low or deep means that the absolute value increases in the negative direction from the vacuum level.

[0077] In this specification, HOMO (highest occupied molecular orbital) refers to the highest energy region in the area where electrons can participate in bonding, LUMO (lowest unoccupied molecular orbital) refers to the lowest energy region in the antibonding area, and HOMO energy level refers to the distance from the vacuum level to the HOMO. Additionally, LUMO energy level refers to the distance from the vacuum level to the LUMO.

[0078] In this specification, bandgap refers to the difference in energy levels between HOMO and LUMO, that is, the HOMO-LUMO gap.

[0079] In this specification, HOMO energy levels can be measured using an atmospheric photoelectron spectrometer (manufactured by RIKEN KEIKI Co., Ltd.: AC3), and LUMO energy levels can be calculated from wavelength values ​​measured through photoluminescence (PL).

[0080] Unless otherwise defined in this specification, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which the present invention pertains. Methods and materials similar or equivalent to those described herein may be used in the practice or testing of embodiments of the present invention, but suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, unless a specific passage is not mentioned, this specification, including definitions, shall prevail. Furthermore, materials, methods, and embodiments are merely illustrative and are not intended to be limiting.

[0081] Preferred embodiments of the present invention are described in detail below. However, embodiments of the present invention may be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

[0082] The organic light-emitting device of the present invention is characterized by including both a compound represented by Formula 1 and a compound represented by Formula 2, and the organic light-emitting device of the present invention exhibits low voltage, high efficiency, and / or long lifespan effects. More specifically, an organic light-emitting device including both the compound of Formula 1 and the compound of Formula 2 exhibits low voltage, high efficiency, and / or long lifespan effects due to an appropriate balance of holes and electrons. In particular, when the compound of Formula 1 is used as a hole transport material, the HOMO energy level of the compound of Formula 1 is low, so the energy barrier between the emitting layer and the hole transport layer is reduced, thereby allowing the barrier between the emitting layer and the hole transport layer to be appropriately controlled. Additionally, when the compound of Formula 2 is used as an electron transport material, the LUMO energy level of the compound of Formula 2 is high, so the energy barrier between the emitting layer and the electron transport layer is reduced, thereby allowing the barrier between the emitting layer and the electron transport layer to be appropriately controlled.

[0083] The compound of Chemical Formula 1 below will be described in detail below.

[0084] [Chemical Formula 1]

[0085]

[0086] In the above chemical formula 1,

[0087] Ar1 and Ar2 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and a substituted or unsubstituted aliphatic hydrocarbon ring, and

[0088] L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0089] L2 and L3 are the same or different from each other, and each is independently directly bonded; or are substituted or unsubstituted arylene groups, and

[0090] R1 to R3 are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0091] a, b, and c are each independently integers from 0 to 3, and if a is 2 or greater, 2 or more L1s are equal to or different from each other, if b is 2 or greater, 2 or more L2s are equal to or different from each other, and if c is 2 or greater, 2 or more L3s are equal to or different from each other, and

[0092] r2 and r3 are each independently integers from 0 to 4, and if r2 is 2 or more, 2 or more R2s are the same or different from each other, and if r3 is 2 or more, 2 or more R3s are the same or different from each other.

[0093] In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted condensed ring of an aromatic hydrocarbon ring having 6 to 60 carbon atoms and a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0094] In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted condensed ring of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

[0095] In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted condensed ring of an aromatic hydrocarbon ring having 6 to 20 carbon atoms and a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms.

[0096] In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms; a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; or a substituted or unsubstituted condensed ring of an aromatic hydrocarbon ring having 6 to 10 carbon atoms and a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 10 carbon atoms.

[0097] In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other and are each independently hydrogen; deuterium; adamantyl group; phenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; biphenyl group substituted or unsubstituted with deuterium; terphenyl group substituted or unsubstituted with deuterium; naphthyl group substituted or unsubstituted with deuterium; fluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; spirobifluorenyl group substituted or unsubstituted with deuterium; phenanthrenyl group substituted or unsubstituted with deuterium; or tetrahydronaphthyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

[0098] In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted adamantyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted spirobifluorenyl group; or a substituted or unsubstituted tetrahydronaphthyl group.

[0099] In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other and are each 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 phenanthrenyl group; or a substituted or unsubstituted fluorenyl group.

[0100] In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other and are each independently hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium or an aryl group; a biphenyl group substituted or unsubstituted with deuterium or an aryl group; a terphenyl group substituted or unsubstituted with deuterium or an aryl group; a naphthyl group substituted or unsubstituted with deuterium or an aryl group; a phenanthrenyl group substituted or unsubstituted with deuterium or an aryl group; or a fluorenyl group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group.

[0101] In one embodiment of the present specification, L1 to L3 are the same or different from each other and are each independently represented by any one of the following structural formulas.

[0102]

[0103]

[0104] In the above structural formula,

[0105] The dotted line indicates the connection location,

[0106] The site substituted with hydrogen can be replaced with deuterium.

[0107] In one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0108] In one embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

[0109] In one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0110] In one embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0111] In one embodiment of the present specification, L1 is each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0112] In one embodiment of the present specification, L1 is each independently directly bonded; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0113] In one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted divalent phenyl group; a substituted or unsubstituted divalent biphenyl group; a substituted or unsubstituted divalent terphenyl group; a substituted or unsubstituted divalent naphthyl group; a substituted or unsubstituted divalent fluorenyl group; a substituted or unsubstituted dirivobifluorenyl group; a substituted or unsubstituted divalent phenanthrenyl group; a substituted or unsubstituted divalent carbazole group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0114] In one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted divalent phenyl group; a substituted or unsubstituted divalent biphenyl group; a substituted or unsubstituted divalent terphenyl group; a substituted or unsubstituted divalent naphthyl group; a substituted or unsubstituted divalent fluorenyl group; a substituted or unsubstituted divalent spirobifluorenyl group; or a substituted or unsubstituted divalent phenanthrene group.

[0115] In one embodiment of the present specification, L1 comprises a direct bond; a divalent phenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent biphenyl group substituted or unsubstituted with deuterium; a divalent terphenyl group substituted or unsubstituted with deuterium; a divalent naphthyl group substituted or unsubstituted with deuterium; a divalent fluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent spirobifluorenyl group substituted or unsubstituted with deuterium; a divalent phenanthrenyl group substituted or unsubstituted with deuterium; a divalent carbazole group substituted or unsubstituted with deuterium; a divalent dibenzofuranyl group substituted or unsubstituted with deuterium; Or it is a divalent dibenzothiophenyl group substituted or unsubstituted with deuterium.

[0116] In one embodiment of the present specification, L1 is a direct bond; a divalent phenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent biphenyl group substituted or unsubstituted with deuterium; a divalent terphenyl group substituted or unsubstituted with deuterium; a divalent naphthyl group substituted or unsubstituted with deuterium; a divalent fluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent spirobifluorenyl group substituted or unsubstituted with deuterium; or a divalent phenanthrenyl group substituted or unsubstituted with deuterium.

[0117] In one embodiment of the present specification, L1 comprises a direct bond; a divalent phenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent biphenyl group substituted or unsubstituted with deuterium; a divalent terphenyl group substituted or unsubstituted with deuterium; a divalent naphthyl group substituted or unsubstituted with deuterium; a divalent fluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent spirobifluorenyl group substituted or unsubstituted with deuterium; a divalent phenanthrenyl group substituted or unsubstituted with deuterium; a divalent carbazole group substituted or unsubstituted with deuterium; a divalent dibenzofuranyl group substituted or unsubstituted with deuterium; Or it is a divalent dibenzothiophenyl group substituted or unsubstituted with deuterium.

[0118] In one embodiment of the present specification, L1 is a direct bond; a divalent phenyl group substituted or unsubstituted with a deuterium or aryl group; a divalent biphenyl group substituted or unsubstituted with a deuterium or aryl group; or a divalent naphthyl group substituted or unsubstituted with a deuterium or aryl group.

[0119] In one embodiment of the present specification, L2 and L3 are the same or different from each other and are each independently directly bonded; or are substituted or unsubstituted arylene groups having 6 to 60 carbon atoms.

[0120] In one embodiment of the present specification, L2 and L3 are the same or different from each other and are each independently directly bonded; or are substituted or unsubstituted arylene groups having 6 to 30 carbon atoms.

[0121] In one embodiment of the present specification, L2 and L3 are the same or different from each other and are each independently directly bonded; or are substituted or unsubstituted arylene groups having 6 to 20 carbon atoms.

[0122] In one embodiment of the present specification, L2 and L3 are the same or different from each other and are each independently direct bonded; a substituted or unsubstituted divalent phenyl group; a substituted or unsubstituted divalent biphenyl group; a substituted or unsubstituted divalent terphenyl group; a substituted or unsubstituted divalent naphthyl group; a substituted or unsubstituted divalent fluorenyl group; a substituted or unsubstituted divalent spirobifluorenyl group; or a substituted or unsubstituted divalent phenanthrenyl group.

[0123] In one embodiment of the present specification, L2 and L3 are the same or different from each other and each independently directly bonded; a divalent phenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent biphenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent terphenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent naphthyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; It is a divalent fluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent spirobifluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; or a divalent phenanthrenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms.

[0124] In one embodiment of the present specification, L2 and L3 are the same or different from each other and are each independently direct bonded; a divalent phenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent biphenyl group substituted or unsubstituted with deuterium; a divalent terphenyl group substituted or unsubstituted with deuterium; a divalent naphthyl group substituted or unsubstituted with deuterium; a divalent fluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent spirobifluorenyl group substituted or unsubstituted with deuterium; or a divalent phenanthrenyl group substituted or unsubstituted with deuterium.

[0125] In one embodiment of the present specification, L2 and L3 are the same or different from each other and are each independently directly bonded; a divalent phenyl group substituted or unsubstituted with a deuterium or aryl group; a divalent biphenyl group substituted or unsubstituted with a deuterium or aryl group; or a divalent naphthyl group substituted or unsubstituted with a deuterium or aryl group.

[0126] In one embodiment of the present specification, R1 to R3 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; 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.

[0127] In one embodiment of the present specification, R1 to R3 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; 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.

[0128] In one embodiment of the present specification, R1 to R3 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; 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.

[0129] In one embodiment of the present specification, R1 to R3 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted carbazole group.

[0130] In one embodiment of the present specification, R1 to R3 are the same or different from each other and are each independently hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; a fluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; or a carbazole group substituted or unsubstituted with deuterium.

[0131] In one embodiment of the present specification, R1 to R3 are the same or different from each other and are each independently hydrogen; deuterium; or a phenyl group substituted or unsubstituted with deuterium.

[0132] In one embodiment of the present specification, a is an integer from 0 to 3, and when a is 2 or more, 2 or more L1s are the same or different from each other.

[0133] In one embodiment of the present specification, a is an integer from 0 to 3.

[0134] In one embodiment of the present specification, a is 3.

[0135] In one embodiment of the present specification, a is 2.

[0136] In one embodiment of the present specification, a is 1.

[0137] In one embodiment of the present specification, a is 0.

[0138] In one embodiment of the present specification, b is an integer from 0 to 3, and if b is 2 or more, 2 or more L2 are the same or different from each other.

[0139] In one embodiment of the present specification, b is an integer from 0 to 3.

[0140] In one embodiment of the present specification, b is 3.

[0141] In one embodiment of the present specification, b is 2.

[0142] In one embodiment of the present specification, b is 1.

[0143] In one embodiment of the present specification, b is 0.

[0144] In one embodiment of the present specification, c is an integer from 0 to 3, and when c is 2 or more, 2 or more L3s are the same or different from each other.

[0145] In one embodiment of the present specification, c is an integer from 0 to 3.

[0146] In one embodiment of the present specification, c is 3.

[0147] In one embodiment of the present specification, c is 2.

[0148] In one embodiment of the present specification, c is 1.

[0149] In one embodiment of the present specification, c is 0.

[0150] In one embodiment of the present specification, r2 is an integer from 0 to 4, and when r2 is 2 or more, the 2 or more R2 are the same or different from each other.

[0151] In one embodiment of the present specification, r2 is an integer from 0 to 4.

[0152] In one embodiment of the present specification, r2 is 4.

[0153] In one embodiment of the present specification, r2 is 3.

[0154] In one embodiment of the present specification, r2 is 2.

[0155] In one embodiment of the present specification, r2 is 1.

[0156] In one embodiment of the present specification, r2 is 0.

[0157] In one embodiment of the present specification, r3 is an integer from 0 to 4, and if r3 is 2 or more, the 2 or more R3s are the same or different from each other.

[0158] In one embodiment of the present specification, r3 is an integer from 0 to 4.

[0159] In one embodiment of the present specification, r3 is 4.

[0160] In one embodiment of the present specification, r3 is 3.

[0161] In one embodiment of the present specification, r3 is 2.

[0162] In one embodiment of the present specification, r3 is 1.

[0163] In one embodiment of the present specification, r3 is 0.

[0164] In one embodiment of the present specification, the formula 1 is represented by any one of the following compounds.

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206] Chemical Formula 2 will be explained in detail below.

[0207] [Chemical Formula 2]

[0208]

[0209] In the above chemical formula 2,

[0210] Ar3 and Ar4 are the same or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0211] L4 to L6 are the same or different from one another, and each is independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0212] R4 to R7 are the same or different from one another, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0213] d, e, and f are each independently integers from 0 to 3, and if d is 2 or greater, L4 of 2 or greater is equal to or different from each other, if e is 2 or greater, L5 of 2 or greater is equal to or different from each other, and if f is 2 or greater, L6 of 2 or greater is equal to or different from each other, and

[0214] r4 and r5 are each independently integers from 0 to 4, and if r4 is 2 or greater, 2 or more R4s are equal to or different from each other, and if r5 is 2 or greater, 2 or more R5s are equal to or different from each other, and

[0215] r6 and r7 are each independently integers from 0 to 3, and if r6 is 2 or more, 2 or more R6s are the same or different from each other, and if r7 is 2 or more, 2 or more R7s are the same or different from each other.

[0216] In one embodiment of the present specification, Ar3 and Ar4 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; 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.

[0217] In one embodiment of the present specification, Ar3 and Ar4 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted carbazole group.

[0218] In one embodiment of the present specification, Ar3 and Ar4 are the same or different from each other and are each independently hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; a fluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; or a carbazole group substituted or unsubstituted with deuterium.

[0219] In one embodiment of the present specification, Ar3 and Ar4 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted adamantyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted dibenzofuranyl group; or a dibenzothiophenyl group substituted or unsubstituted with deuterium.

[0220] In one embodiment of the present specification, Ar3 and Ar4 are the same or different from each other and are each 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 phenanthrenyl group; or a substituted or unsubstituted fluorenyl group.

[0221] In one embodiment of the present specification, Ar3 and Ar4 are the same or different from each other and are each independently hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium or an aryl group; a biphenyl group substituted or unsubstituted with deuterium or an aryl group; a terphenyl group substituted or unsubstituted with deuterium or an aryl group; a naphthyl group substituted or unsubstituted with deuterium or an aryl group; a phenanthrenyl group substituted or unsubstituted with deuterium or an aryl group; or a fluorenyl group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group.

[0222] In one embodiment of the present specification, Ar3 and Ar4 are the same or different from each other and are each independently hydrogen; deuterium; or a phenyl group substituted or unsubstituted with deuterium.

[0223] In one embodiment of the present specification, L4 to L6 are the same or different from each other and are each independently represented by any one of the following structural formulas.

[0224]

[0225]

[0226] In the above structural formula,

[0227] The dotted line indicates the connection location,

[0228] The site substituted with hydrogen can be replaced with deuterium.

[0229] In one embodiment of the present specification, L4 to L6 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0230] In one embodiment of the present specification, L4 to L6 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0231] In one embodiment of the present specification, L4 to L6 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0232] In one embodiment of the present specification, L4 to L6 are the same or different from each other and are each independently direct bonded; a substituted or unsubstituted divalent phenyl group; a substituted or unsubstituted divalent biphenyl group; a substituted or unsubstituted divalent terphenyl group; a substituted or unsubstituted divalent naphthyl group; a substituted or unsubstituted divalent fluorenyl group; a substituted or unsubstituted dirivobifluorenyl group; a substituted or unsubstituted divalent phenanthrenyl group; a substituted or unsubstituted divalent carbazole group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0233] In one embodiment of the present specification, L4 to L6 are the same or different from each other and each independently directly bonded; a divalent phenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent biphenyl group substituted or unsubstituted with deuterium; a divalent terphenyl group substituted or unsubstituted with deuterium; a divalent naphthyl group substituted or unsubstituted with deuterium; a divalent fluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent spirobifluorenyl group substituted or unsubstituted with deuterium; a divalent phenanthrenyl group substituted or unsubstituted with deuterium; a divalent carbazole group substituted or unsubstituted with deuterium; It is a divalent dibenzofuranyl group substituted or unsubstituted with deuterium; or a divalent dibenzothiophenyl group substituted or unsubstituted with deuterium.

[0234] In one embodiment of the present specification, L4 to L6 are the same or different from each other and each independently directly bonded; a divalent phenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent biphenyl group substituted or unsubstituted with deuterium; a divalent terphenyl group substituted or unsubstituted with deuterium; a divalent naphthyl group substituted or unsubstituted with deuterium; a divalent fluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent spirobifluorenyl group substituted or unsubstituted with deuterium; a divalent phenanthrenyl group substituted or unsubstituted with deuterium; a divalent carbazole group substituted or unsubstituted with deuterium; It is a divalent dibenzofuranyl group substituted or unsubstituted with deuterium; or a divalent dibenzothiophenyl group substituted or unsubstituted with deuterium.

[0235] In one embodiment of the present specification, L4 to L6 are the same or different from each other and are each independently direct bonded; a divalent phenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent biphenyl group substituted or unsubstituted with deuterium; a divalent terphenyl group substituted or unsubstituted with deuterium; a divalent naphthyl group substituted or unsubstituted with deuterium; or a divalent fluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms.

[0236] In one embodiment of the present specification, L4 to L6 are the same or different from each other and are each independently direct bonded; a divalent phenyl group substituted or unsubstituted with a deuterium or aryl group; a divalent biphenyl group substituted or unsubstituted with a deuterium or aryl group; a divalent terphenyl group substituted or unsubstituted with a deuterium or aryl group; or a divalent naphthyl group substituted or unsubstituted with a deuterium or aryl group.

[0237] In one embodiment of the present specification, R4 to R7 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; 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.

[0238] In one embodiment of the present specification, R4 to R7 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; 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.

[0239] In one embodiment of the present specification, R4 to R7 are the same or different from one another and are each independently hydrogen or deuterium.

[0240] In one embodiment of the present specification, d is an integer from 0 to 3, and when d is 2 or more, 2 or more L4s are the same or different from each other.

[0241] In one embodiment of the present specification, d is an integer from 0 to 3.

[0242] In one embodiment of the present specification, d is 3.

[0243] In one embodiment of the present specification, d is 2.

[0244] In one embodiment of the present specification, d is 1.

[0245] In one embodiment of the present specification, d is 0.

[0246] In one embodiment of the present specification, e is an integer from 0 to 3, and when e is 2 or more, 2 or more L5s are the same or different from each other.

[0247] In one embodiment of the present specification, e is an integer from 0 to 3.

[0248] In one embodiment of the present specification, e is 3.

[0249] In one embodiment of the present specification, e is 2.

[0250] In one embodiment of the present specification, e is 1.

[0251] In one embodiment of the present specification, e is 0.

[0252] In one embodiment of the present specification, f is an integer from 0 to 3, and if f is 2 or more, 2 or more L6s are the same or different from each other.

[0253] In one embodiment of the present specification, f is an integer from 0 to 3.

[0254] In one embodiment of the present specification, f is 3.

[0255] In one embodiment of the present specification, f is 2.

[0256] In one embodiment of the present specification, f is 1.

[0257] In one embodiment of the present specification, f is 0.

[0258] In one embodiment of the present specification, r4 is an integer from 0 to 4, and if r4 is 2 or more, the 2 or more R4s are the same or different from each other.

[0259] In one embodiment of the present specification, r4 is an integer from 0 to 4.

[0260] In one embodiment of the present specification, r4 is 4.

[0261] In one embodiment of the present specification, r4 is 3.

[0262] In one embodiment of the present specification, r4 is 2.

[0263] In one embodiment of the present specification, r4 is 1.

[0264] In one embodiment of the present specification, r4 is 0.

[0265] In one embodiment of the present specification, r5 is an integer from 0 to 4, and if r5 is 2 or more, the 2 or more R5s are the same or different from each other.

[0266] In one embodiment of the present specification, r5 is an integer from 0 to 4.

[0267] In one embodiment of the present specification, r5 is 4.

[0268] In one embodiment of the present specification, r5 is 3.

[0269] In one embodiment of the present specification, r5 is 2.

[0270] In one embodiment of the present specification, r5 is 1.

[0271] In one embodiment of the present specification, r5 is 0.

[0272] In one embodiment of the present specification, r6 is an integer from 0 to 3, and when r6 is 2 or more, the 2 or more R6s are the same or different from each other.

[0273] In one embodiment of the present specification, r6 is an integer from 0 to 3.

[0274] In one embodiment of the present specification, r6 is 3.

[0275] In one embodiment of the present specification, r6 is 2.

[0276] In one embodiment of the present specification, r6 is 1.

[0277] In one embodiment of the present specification, r6 is 0.

[0278] In one embodiment of the present specification, r7 is an integer from 0 to 3, and when r7 is 2 or more, the 2 or more R7s are the same or different from each other.

[0279] In one embodiment of the present specification, r7 is an integer from 0 to 3.

[0280] In one embodiment of the present specification, r7 is 3.

[0281] In one embodiment of the present specification, r7 is 2.

[0282] In one embodiment of the present specification, r7 is 1.

[0283] In one embodiment of the present specification, r7 is 0.

[0284] In one embodiment of the present specification, the formula 2 is represented by any one of the following compounds.

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294] Compounds represented by Formula 1 and Formula 2 according to one embodiment of this specification may have a core structure prepared as in the method of the manufacturing example described below. Substituents may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

[0295] In this specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compounds represented by Chemical Formula 1 and Chemical Formula 2. In addition, in this specification, the HOMO and LUMO energy levels of the compounds can also be controlled by introducing various substituents into the core structure of such a structure.

[0296] In addition, by introducing various substituents into a core structure having the structure described above, compounds possessing the unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents primarily used in hole injection materials, hole transport materials, electron blocking materials, light-emitting materials, and electron transport materials used in the manufacture of organic light-emitting devices into the core structure, materials that satisfy the conditions required for each organic layer can be synthesized.

[0297] The following describes organic light-emitting diodes.

[0298] In this specification, the term "layer" is used in a sense compatible with "film" as is commonly used in the art, and refers to a coating that covers a target area. The size of the "layer" is not limited, and each "layer" may have the same or different sizes. According to one embodiment, the size of the "layer" may be equal to the size of the entire device, correspond to the size of a specific functional area, or be as small as a single subpixel.

[0299] In the present specification, the meaning of a specific A substance being included in a B layer includes both i) one or more types of A substances being included in a single B layer and ii) the B layer being composed of one or more layers and A substance being included in one or more layers among the multilayer B layers.

[0300] In the present specification, the meaning that a specific A material is included in a C layer or a D layer is that it is included in at least one of the C layers, ii) included in at least one of the D layers, or iii) included in each of the C layers and the D layers.

[0301] An organic light-emitting device according to one embodiment of the present specification 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 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.

[0302] An organic light-emitting device according to one embodiment of the present specification can be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except that an organic layer is formed using a compound represented by the aforementioned Chemical Formula 1 and a compound of the aforementioned Chemical Formula 2.

[0303] The above compound can be formed as an organic layer by vacuum deposition as well as by solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0304] For example, the organic light-emitting diode of the present specification can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. In this case, the device can be manufactured by using a physical vapor deposition (PVD) method, such as sputtering or electron beam evaporation, to form an anode by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate, forming an organic layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting diode can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0305] The organic layer of an organic light-emitting device according to one embodiment of the present specification may be formed as a single layer structure, but may be formed as a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present specification may have a structure comprising one or more layers among a hole injection layer, a hole transport layer, a hole injection and transport layer, a hole transport assist layer, an electron suppression layer, a light-emitting layer, a hole suppression layer, an electron transport layer, an electron injection layer, and an electron transport and injection layer as organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers or a larger number of organic layers.

[0306] In one embodiment of the present specification, the first organic layer may include a hole injection layer, a hole transport layer, or a hole injection and transport layer. In one embodiment of the present specification, the first organic layer may include a hole injection layer, a hole transport layer, a hole injection and transport layer, a hole transport assist layer, or an electron suppression layer, and the hole transport layer may include a compound represented by Formula 1.

[0307] In one embodiment of the present specification, the first organic layer is a hole injection layer, a hole transport layer, a hole injection and transport layer, a hole transport assisting layer, or an electron suppression layer.

[0308] In one embodiment of the present specification, the first organic layer is a hole transport assisting layer.

[0309] In one embodiment of the present specification, the second organic layer may include a hole suppression layer, an electron transport layer, an electron injection layer, and an electron transport and injection layer.

[0310] In one embodiment of the present specification, the second organic layer comprises an electron transport layer, and the electron transport layer may comprise a compound represented by Formula 2.

[0311] In one embodiment of the present specification, the second organic layer is an electron transport layer, an electron injection layer, or an electron transport and injection layer.

[0312] In one embodiment of the present specification, the second organic layer may include an electron transport and injection layer, and the electron transport and injection layer may include a compound represented by Formula 2.

[0313] In one embodiment of the present specification, the second organic layer is an electron transport and injection layer.

[0314] In one embodiment of the present specification, the second organic layer may further include a metal complex compound.

[0315] In one embodiment of the present specification, the second organic layer may further include a lithium metal complex compound.

[0316] In one embodiment of the present specification, the second organic layer may further include 8-hydroxyquinolinato lithium (LiQ).

[0317] In one embodiment of the present specification, the second organic layer comprises a compound represented by Formula 2 and may further comprise a metal complex compound, and the weight ratio of the compound represented by Formula 2 to the metal complex compound may be 1:9 to 9:1.

[0318] In one embodiment of the present specification, the second organic layer comprises a compound represented by Formula 2 and may further comprise a metal complex compound, and the weight ratio of the compound represented by Formula 2 to the metal complex compound may be 2:8 to 8:2, 3:7 to 7:3, or 4:6 to 6:4.

[0319] In one embodiment of the present specification, the second organic layer comprises a compound represented by Formula 2 and may further comprise a metal complex compound, and the weight ratio of the compound represented by Formula 2 to the metal complex compound may be 5:5.

[0320] In an organic light-emitting device according to one embodiment of the present specification, one or more organic layers may be additionally provided between the anode and the cathode, and the organic layers may further include one or more of a hole injection layer, a hole transport layer, a hole injection and transport layer, a hole transport assist layer, an electron suppression layer, a light-emitting layer, a hole suppression layer, an electron transport layer, an electron injection layer, and an electron transport and injection layer and an electron suppression layer.

[0321] In one embodiment of the present specification, when the organic light-emitting element comprises a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0322] In an organic light-emitting device according to one embodiment of the present specification, one or more organic layers may be additionally provided between the anode and the cathode, and the organic layers may be light-emitting layers.

[0323] In one embodiment of the present specification, the first organic layer may be provided between the anode and the light-emitting layer.

[0324] In one embodiment of the present specification, the first organic layer may be provided in contact with the light-emitting layer.

[0325] In one embodiment of the present specification, the second organic layer may be provided between the light-emitting layer and the cathode.

[0326] In one embodiment of the present specification, a hole suppression layer may be provided between the second organic layer and the light-emitting layer.

[0327] In one embodiment of the present specification, the organic light-emitting element comprises an anode; a cathode; two or more first organic layers provided between the anode and the cathode and a second organic layer provided between the cathode and the first organic layer, wherein the two or more first organic layers comprise a compound represented by Formula 1 and the two or more second organic layers may comprise a compound represented by Formula 2.

[0328] In an organic light-emitting device according to one embodiment of the present specification, the first organic layer comprises two or more hole transport assisting layers, and at least one of the two or more hole transport layers may comprise a compound represented by Formula 1. Additionally, the two or more hole transport layers may be formed of the same material or a different material.

[0329] In an organic light-emitting device according to one embodiment of the present specification, the second organic layer comprises two or more electron transport and injection layers, and at least one of the two or more electron transport and injection layers may comprise a compound represented by Formula 2. Additionally, the two or more electron transport and injection layers may be formed of the same material or a different material.

[0330] In one embodiment of the present specification, the thickness of the first organic layer comprising a compound represented by Formula 1 and the second organic layer comprising a compound represented by Formula 2 is each 10 Å to 600 Å, preferably 50 Å to 500 Å, and more preferably 80 Å to 400 Å.

[0331] In one embodiment of the present specification, the first organic layer and the second organic layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by the aforementioned Chemical Formula 1 and the compound represented by the aforementioned Chemical Formula 2.

[0332] In another embodiment, the first organic layer and the second organic layer do not include any other organic compounds, metals, or metal compounds other than the compound represented by the aforementioned Chemical Formula 1 and the compound represented by the aforementioned Chemical Formula 2.

[0333] In one embodiment of the present specification, the first organic layer and the second organic layer may be provided in contact with each other.

[0334] In one embodiment of the present specification, the first organic layer and the second organic layer may not be provided in contact with each other.

[0335] In one embodiment of the present specification, one or more organic layers are located between the first organic layer and the second organic layer.

[0336] In one embodiment of the present specification, a light-emitting layer is located between the first organic layer and the second organic layer.

[0337] In one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device of a normal type structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0338] In one embodiment of the present specification, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0339] The above organic light-emitting device may have a stacked structure such as, for example, the following, but is not limited thereto.

[0340] (1) Anode / hole transport layer / emissive layer / cathode

[0341] (2) Anode / hole injection layer / hole transport layer / emissive layer / cathode

[0342] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / cathode

[0343] (4) Anode / hole transport layer / emissive layer / electron transport layer / cathode

[0344] (5) Anode / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0345] (6) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / cathode

[0346] (7) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0347] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / cathode

[0348] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0349] (10) Anode / hole transport layer / electron suppression layer / emissive layer / electron transport layer / cathode

[0350] (11) Anode / hole transport layer / electron suppression layer / emissive layer / electron transport layer / electron injection layer / cathode

[0351] (12) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / electron transport layer / cathode

[0352] (13) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / electron transport layer / electron injection layer / cathode

[0353] (14) Anode / hole transport layer / emissive layer / hole suppression layer / electron transport layer / cathode

[0354] (15) Anode / hole transport layer / emissive layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0355] (16) Anode / hole injection layer / hole transport layer / emissive layer / hole suppression layer / electron transport layer / cathode

[0356] (17) Anode / hole injection layer / hole transport layer / emissive layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0357] (18) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / hole suppression layer / electron transport and injection layer / cathode

[0358] (19) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / hole suppression layer / electron transport and injection layer / cathode / capping layer

[0359] (20) Anode / hole injection layer / hole transport layer / hole transport assist layer / emissive layer / hole suppression layer / electron transport and injection layer / cathode

[0360] (21) Anode / hole injection layer / hole transport layer / hole transport assist layer / emissive layer / hole suppression layer / electron transport and injection layer / cathode / capping layer

[0361] (22) Anode / hole injection layer / hole transport layer / hole transport assist layer / electron suppression layer / emissive layer / hole suppression layer / electron transport and injection layer / cathode / capping layer

[0362]

[0363] The structure of the organic light-emitting device of the present specification may have a structure such as that shown in FIGS. 1 to 2, but is not limited thereto.

[0364] FIG. 1 illustrates the structure of an organic light-emitting device in which a substrate (1), an anode (2), a first organic layer (21), a second organic layer (22), and a cathode (9) are sequentially stacked. In such a structure, the compound represented by Formula 1 may be included in the first organic layer (21), and the compound represented by Formula 2 may be included in the second organic layer (22).

[0365] 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), a hole transport assist layer (5), a light-emitting layer (6), a hole suppression layer (7), an electron transport and injection layer (8), and a cathode (9) are sequentially stacked. In such a structure, the compound represented by Chemical Formula 1 may be included in the hole transport layer (4) or the hole transport assist layer (5), and the compound represented by Chemical Formula 2 may be included in the electron transport and injection layer (8).

[0366] According to one embodiment of the present specification, 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 bonded to a charge generation layer. Since the element of the tandem structure can be driven at a lower current than the unit element based on the same brightness, the lifespan characteristics of the element are greatly improved.

[0367] For example, an organic light-emitting device according to one embodiment of the present specification may be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation, forming an organic layer comprising one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport and injection layer, a light-emitting layer, an electron transport layer, an electron injection layer, and an electron transport and injection layer, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device may also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0368] The above organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, an emitting layer, and an electron transport and injection layer, but is not limited thereto and may have a single layer structure. In addition, the above organic layer may be manufactured with fewer layers by using various polymer materials and a solvent process other than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0369] The above anode is an electrode that injects holes, and as the anode material, it is generally preferable to use an organic layer with a high work function to facilitate hole injection. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0370] The above cathode is an electrode for injecting electrons, and the cathode material is typically an organic layer, preferably a material with a low work function to facilitate electron injection. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0371] The hole injection layer described above is a layer that facilitates the injection of holes from the anode to the light-emitting layer. The hole injection material is a material capable of receiving holes well from the anode at 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 metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile-hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and conductive polymers of polyaniline and polythiophene series, but are not limited to these. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing the hole injection characteristics from deteriorating, and if it is 150 nm or less, there is an advantage of preventing the driving voltage from rising to improve the movement of holes because the thickness of the hole injection layer is too thick.

[0372] According to one embodiment of the present specification, the hole injection layer comprises a compound of the following chemical formula HI-1.

[0373] [Chemical Formula HI-1]

[0374]

[0375] In the above chemical formula HI-1,

[0376] L101 is a direct bond; or a substituted or unsubstituted arylene group, and

[0377] R101 to R103 are the same or different from each other and are each independently substituted or unsubstituted aryl groups.

[0378] According to one embodiment of the present specification, the L101 is a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0379] According to one embodiment of the present specification, the L101 is a direct bond; or a substituted or unsubstituted phenylene group.

[0380] According to one embodiment of the present specification, the L101 is a direct bond; or a phenylene group.

[0381] According to one embodiment of the present specification, R101 to R103 are the same or different from one another and are each independently substituted or unsubstituted single-ring aryl groups; or substituted or unsubstituted polycyclic aryl groups.

[0382] According to one embodiment of the present specification, R101 to R103 are the same or different from one another and are each 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 anthracenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted pyrene group; or a substituted or unsubstituted fluorenyl group.

[0383] According to one embodiment of the present specification, R101 to R103 are the same or different from each other and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted fluorenyl group.

[0384] According to one embodiment of the present specification, R101 to R103 are the same or different from each other and are each independently a fluorenyl group substituted with a phenyl group; a biphenyl group; or an alkyl group.

[0385] According to one embodiment of the present specification, the chemical formula HI-1 may be represented by the following compounds, but is not limited thereto.

[0386]

[0387] According to one embodiment of the present specification, the hole injection layer comprises a compound of the following chemical formula HI-2.

[0388] [Chemical Formula HI-2]

[0389]

[0390] In the above chemical formula HI-2,

[0391] R111 to R113 are the same or different from one another, and each independently is hydrogen; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0392] a111 to a113 are each integers from 1 to 5, and

[0393] If a111 is 2 or more, the 2 or more R111s are the same or different from each other, and

[0394] If a112 is 2 or more, 2 or more R112s are the same or different from each other, and

[0395] If a113 is 2 or more, then 2 or more R113s are the same or different from each other.

[0396] According to one embodiment of the present specification, R111 to R113 are the same or different from each other and are each a halogen group; or a nitrile group.

[0397] According to one embodiment of the present specification, R111 to R113 are the same or different from each other and are each fluorine; or a nitrile group.

[0398] According to one embodiment of the present specification, the formula HI-2 may be represented by the following compounds, but is not limited thereto.

[0399]

[0400] According to one embodiment of the present specification, the hole injection layer comprises a compound of the formula HI-1 and a compound of the formula HI-2.

[0401] The hole transport layer described above can facilitate the transport of holes. Suitable hole transport materials are those capable of receiving holes from the anode or hole injection layer and transferring them to the emissive layer, provided they possess high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0402] In one embodiment of the present specification, the hole transport layer comprises a compound of the following formula HT-1.

[0403] [Chemical Formula HT-1]

[0404]

[0405] In the above chemical formula HI-1,

[0406] L201 and L202 are the same or different from each other, and each is independently directly bonded; or are substituted or unsubstituted arylene groups, and

[0407] R200 is a substituted or unsubstituted aryl group, and

[0408] R201 to R204 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0409] In one embodiment of the present specification, L201 and L202 are the same or different from each other and are each independently substituted or unsubstituted arylene groups.

[0410] In one embodiment of the present specification, L201 and L202 are the same or different from each other and are each independently substituted or unsubstituted phenylene groups; or substituted or unsubstituted naphthylene groups.

[0411] In one embodiment of the present specification, L201 and L202 are the same or different from each other and are each independently substituted or unsubstituted phenylene groups.

[0412] In one embodiment of the present specification, L201 and L202 are each phenylene groups.

[0413] In one embodiment of the present specification, R200 is a substituted or unsubstituted single-ring aryl group; or a substituted or unsubstituted polycyclic aryl group.

[0414] In one embodiment of the present specification, the R200 is 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 anthracenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted pyrene group; or a substituted or unsubstituted fluorenyl group.

[0415] In one embodiment of the present specification, the R200 is a substituted or unsubstituted phenyl group.

[0416] In one embodiment of the present specification, R201 to R204 are the same or different from one another and are each independently substituted or unsubstituted aryl groups.

[0417] In one embodiment of the present specification, R201 to R204 are the same or different from one another and are each independently substituted or unsubstituted single-ring aryl groups; or substituted or unsubstituted polycyclic aryl groups.

[0418] In one embodiment of the present specification, R201 to R204 are the same or different from one another and are each 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 anthracenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted pyrene group; or a substituted or unsubstituted fluorenyl group.

[0419] In one embodiment of the present specification, R201 to R204 are the same or different from each other and are each independently substituted or unsubstituted phenyl groups.

[0420] In one embodiment of the present specification, R201 to R204 are each phenyl groups.

[0421] In one embodiment of the present specification, the chemical formula HT-1 is represented by the following compound.

[0422]

[0423] The electron suppression layer described above is a layer capable of improving the lifespan and efficiency of a device by controlling the smooth injection of holes transported from the hole transport layer into the light-emitting layer and preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. It may be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and a layer that performs both hole injection and hole transport simultaneously, and known materials may be used without limitation.

[0424] A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.

[0425] A hole transport assisting layer may be additionally provided between the hole transport layer and the light-emitting layer, and the hole transport assisting layer may include a compound of Formula 1.

[0426] An electron suppression layer may be provided between the hole transport layer and the light-emitting layer. The electron suppression layer may be a spiro compound or a material known in the art.

[0427] The above-mentioned light-emitting layer may 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 capable of emitting light in the visible light region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole, and benzimidazole series; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0428] Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0429] When the emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the emitting dopant, but are not limited thereto. When the emitting layer emits green light, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the emitting dopant, but are not limited thereto. When the light-emitting layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distrylarylene (DSA), PFO-based polymers, and PPV-based polymers may be used as light-emitting dopants, but are not limited thereto.

[0430] A hole suppression layer may be provided between the electron transport layer and the light-emitting layer. The hole suppression layer is a layer that prevents holes from reaching the cathode and can generally be formed under the same conditions as the electron injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc. are used, but are not limited thereto.

[0431] The electron transport layer described above is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer, and can play a role in facilitating electron transport. As an electron transport material, a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, and a material with high electron mobility is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes, but are not limited to these. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the electron transport characteristics from degrading, and if it is 50 nm or less, there is an advantage in preventing the driving voltage from rising to improve electron transport due to the electron transport layer being too thick.

[0432] The electron injection layer described above can facilitate the injection of electrons. As an electron injection material, a compound is preferred that has the ability to transport electrons, has an excellent electron injection effect from the cathode, an excellent electron injection effect on the emissive layer or the emissive material, prevents the movement of excitons generated in the emissive layer to the hole injection layer, and also has excellent thin film formation ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, etc., their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but is not limited thereto.

[0433] The electron injection material may include at least one of magnesium and lithium fluoride (LiF), and specifically may include both magnesium and lithium fluoride (LiF), but is not limited thereto.

[0434] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, Examples include bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, but are not limited thereto.

[0435] The above electron transport and injection layer is a layer that transports electrons to the light-emitting layer. The materials exemplified in the above electron transport layer and electron injection layer may be used, but are not limited thereto.

[0436] The above electron transport and injection layer can be described as an electron injection and transport layer.

[0437] The electron transport and injection layer comprises the compound of Formula 2 above.

[0438] In one embodiment of the present specification, the electron transport and injection layer may further comprise the compound of Formula 2 and the metal complex compound. The metal complex compound is as described above.

[0439] In one embodiment of the present specification, a capping layer (CPL) may be deposited on the outer edge of the cathode, and the capping layer may include a capping layer material known in the art, which serves to maximize the light extraction effect or prevent degradation of the organic light-emitting diode.

[0440] An organic light-emitting device according to one embodiment of the present specification may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0441] The organic light-emitting element according to the present specification may be included in and used in various electronic devices. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0442] Hereinafter, to specifically explain this specification, examples will be described in detail. However, the embodiments according to this specification may be modified in various different forms, and the scope of this application is not to be interpreted as being limited to the embodiments described below. The embodiments of this application are provided to more completely explain this specification to those with average knowledge in the art.

[0443]

[0444] Preparation Example 1-1

[0445]

[0446] Compound a (20 g, 69.25 mmol) and compound b (28.08 g, 70.64 mmol) were completely dissolved in 300 mL of xylene in a 500 mL round-bottom flask under a nitrogen atmosphere, then NaOtBu (9.31 g, 96.96 mmol) was added, followed by the addition of [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.17 g, 0.34 mmol), and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the base was removed by filtering, the xylene was concentrated under reduced pressure, and the mixture was recrystallized with 240 mL of ethyl acetate to prepare compound 1-1 (40.50 g, yield: 90%).

[0447]

[0448] MS[M+H]+= 650

[0449]

[0450] Preparation Example 1-2

[0451]

[0452] Compound a (20 g, 69.25 mmol) and compound c (26.24 g, 70.64 mmol) were completely dissolved in 300 mL of xylene in a 500 mL round-bottom flask under a nitrogen atmosphere, then NaOtBu (9.31 g, 96.96 mmol) was added, followed by the addition of [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.17 g, 0.34 mmol) and heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare compound 1-2 (36.29 g, yield: 84%).

[0453] MS[M+H]+= 624

[0454]

[0455] Preparation Examples 1-3

[0456]

[0457] Compound a (20 g, 69.25 mmol) and compound d (29.78 g, 70.64 mmol) were completely dissolved in 300 mL of xylene in a 500 mL round-bottom flask under a nitrogen atmosphere, then NaOtBu (9.31 g, 96.96 mmol) was added, followed by the addition of [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.17 g, 0.34 mmol), and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the base was removed by filtering, the xylene was concentrated under reduced pressure, and the mixture was recrystallized with 240 mL of ethyl acetate to prepare compound 1-3 (39.32 g, yield: 89%).

[0458] MS[M+H]+= 674

[0459]

[0460] Preparation Examples 1-4

[0461]

[0462] Compound e (20 g, 69.25 mmol) and compound d (29.78 g, 70.64 mmol) were completely dissolved in 300 mL of xylene in a 500 mL round-bottom flask under a nitrogen atmosphere, then NaOtBu (9.31 g, 96.96 mmol) was added, followed by the addition of [1,1-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.17 g, 0.34 mmol), and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the base was removed by filtering, the xylene was concentrated under reduced pressure, and the mixture was recrystallized with 240 mL of ethyl acetate to prepare compound 1-4 (38.43 g, yield: 87%).

[0463] MS[M+H]+= 674

[0464]

[0465] Preparation Examples 1-5

[0466]

[0467] Compound a (20 g, 69.25 mmol) and compound f (29.78 g, 70.64 mmol) were completely dissolved in 300 mL of xylene in a 500 mL round-bottom flask under a nitrogen atmosphere, then NaOtBu (9.31 g, 96.96 mmol) was added, followed by the addition of [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.17 g, 0.34 mmol), and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the base was removed by filtering, the xylene was concentrated under reduced pressure, and the mixture was recrystallized with 240 mL of ethyl acetate to prepare Compound 1-5 (40.64 g, yield: 92%).

[0468] MS[M+H]+= 674

[0469]

[0470] Preparation Examples 1-6

[0471]

[0472] Compound a (20 g, 69.25 mmol) and compound g (28.93 g, 70.64 mmol) were completely dissolved in 300 mL of xylene in a 500 mL round-bottom flask under a nitrogen atmosphere, then NaOtBu (9.31 g, 96.96 mmol) was added, followed by the addition of [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.17 g, 0.34 mmol), and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the base was removed by filtering, the xylene was concentrated under reduced pressure, and the mixture was recrystallized with 240 mL of ethyl acetate to prepare compound 1-6 (39.42 g, yield: 86%).

[0473] MS[M+H]+= 662

[0474]

[0475] Preparation Examples 1-7

[0476]

[0477] Compound h (20 g, 54.93 mmol) and compound i (18.01 g, 56.03 mmol) were completely dissolved in 300 mL of xylene in a 500 mL round-bottom flask under a nitrogen atmosphere, then NaOtBu (7.39 g, 76.90 mmol) was added, followed by the addition of [1,1'-diphenylphosphino)ferrocene]dichloropalladium(II) (0.17 g, 0.34 mmol), and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the base was removed by filtering, the xylene was concentrated under reduced pressure, and the mixture was recrystallized with 240 mL of ethyl acetate to prepare compound 1-7 (31.41 g, yield: 88%).

[0478] MS[M+H]+= 650

[0479]

[0480] Preparation Example 1-8

[0481]

[0482] Compound 1-3 (20 g, mmol) was completely dissolved in 160 mL of 1,1,2,2-tetrachloroethane in a 500 mL round-bottom flask under a nitrogen atmosphere, then 85.77 mL of a heavy water:trifluoromethanesulfonic acid anhydride = 5:1 solution was added, and the mixture was heated and stirred for 3 hours after raising the temperature to 130 °C. The temperature was lowered to room temperature, the organic layer was separated, and the mixture was uprooted with a 10% aqueous potassium carbonate solution. The 1,1,2,2-tetrachloroethane was then concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare Compound 1-8 (14.44 g, yield: 75%).

[0483] MS[M+H]+= 697

[0484]

[0485] Preparation Example 2-1

[0486]

[0487] Compound A (20 g, 41.37 mmol) and Compound B (19.21, 41.37 mmol) were completely dissolved in tetrahydrofuran (THF) (200 mL) in a 500 mL round-bottom flask under a nitrogen atmosphere, and then potassium carbonate (17.15 g, 124.13 mmol) dissolved in 50 mL of water was added. After adding tetracitriphenyl-phosphinopalladium (1.43 g, 1.24 mmol), the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed twice each with THF and ethyl acetate to prepare Compound 2-1 (21.46 g, yield 70%).

[0488] MS[M+H]+= 741

[0489]

[0490] Preparation Example 2-2

[0491]

[0492] Compound A (20 g, 41.37 mmol) and Compound C (19.21, 41.37 mmol) were completely dissolved in tetrahydrofuran (THF) (200 mL) in a 500 mL round-bottom flask under a nitrogen atmosphere, and then potassium carbonate (17.15 g, 124.13 mmol) dissolved in 50 mL of water was added. After adding tetracitriphenyl-phosphinopalladium (1.43 g, 1.24 mmol), the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed twice each with THF and ethyl acetate to prepare Compound 2-2 (22.99 g, yield 75%).

[0493] MS[M+H]+= 741

[0494]

[0495] Preparation Example 2-3

[0496]

[0497] Compound A (20 g, 41.37 mmol) and Compound D (19.21, 41.37 mmol) were completely dissolved in tetrahydrofuran (THF) (200 mL) in a 500 mL round-bottom flask under a nitrogen atmosphere, and then potassium carbonate (17.15 g, 124.13 mmol) dissolved in 50 mL of water was added. After adding tetracitriphenyl-phosphinopalladium (1.43 g, 1.24 mmol), the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed twice each with THF and ethyl acetate to prepare Compound 2-3 (22.07 g, yield 72%).

[0498] MS[M+H]+= 741

[0499]

[0500] Preparation Example 2-4

[0501]

[0502] Compound A (20 g, 41.37 mmol) and Compound E (19.21, 41.37 mmol) were completely dissolved in tetrahydrofuran (THF) (200 mL) in a 500 mL round-bottom flask under a nitrogen atmosphere, and then potassium carbonate (17.15 g, 124.13 mmol) dissolved in 50 mL of water was added. After adding tetracitriphenyl-phosphinopalladium (1.43 g, 1.24 mmol), the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed twice each with THF and ethyl acetate to prepare Compound 2-4 (24.21 g, yield 79%).

[0503] MS[M+H]+= 741

[0504]

[0505] Example 1

[0506] A glass substrate coated with an indium tin oxide (ITO) thin film to a thickness of 1,000 Å was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. products were used as the detergent, and distilled water that had been filtered twice using a Millerpore Co. filter was used. After cleaning the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol as solvents, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes and then transported to a vacuum deposition machine.

[0507] A hole injection layer was formed on the prepared ITO transparent electrode anode by thermal vacuum deposition of compounds HI1 and HI2 to a thickness of 100 Å in a ratio of 98:2 (molar ratio). A hole transport layer was formed by vacuum deposition of a compound represented by the chemical formula HT1 (1150 Å) on the hole injection layer. Subsequently, a hole transport assist layer was formed by vacuum deposition of compound 1-1 to a film thickness of 350 Å on the hole transport layer. Subsequently, a light-emitting layer was formed by vacuum deposition of a compound represented by the chemical formula RH-1 and a compound represented by the chemical formula RD to a film thickness of 400 Å on the hole transport assist layer in a weight ratio of 98:2. A hole suppression layer was formed by vacuum deposition of a compound represented by the chemical formula HB1 to a film thickness of 50 Å on the light-emitting layer. Next, the following compound 2-1 and the compound represented by the following chemical formula LiQ were vacuum-deposited in a weight ratio of 2:1 on the hole-inhibiting layer to form an electron transport and injection layer with a thickness of 310 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) with a thickness of 12 Å and aluminum with a thickness of 1,000 Å on the electron transport and injection layer.

[0508]

[0509]

[0510] In the above process, the deposition rate of the organic material was maintained at 0.4–0.7 Å / sec, while the deposition rates for the cathode lithium fluoride and aluminum were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 2 × 10⁻¹⁰ -7 ~ 5 x 10 -6 An organic light-emitting diode was fabricated by maintaining torr.

[0511]

[0512] Examples 2 to 32

[0513] An organic light-emitting diode was prepared in the same manner as in Example 1, except that the compounds listed in Table 1 below were used instead of the compounds 1-1 and 2-1 above.

[0514]

[0515] Comparative Examples 1 to 12

[0516] An organic light-emitting diode was prepared in the same manner as in Example 1-1, except that compounds listed in Table 1 below were used instead of Compound 1-1 and Compound 2-1. The compounds HT2 to HT7 and ET1 to ET3 used in Table 1 below are as follows.

[0517]

[0518] Experimental Example

[0519] When current was applied to the organic light-emitting diodes prepared in the above examples and comparative examples, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

[0520] Hole Transport Assist Layer Electron Transport and Injection Layer Voltage (V) Efficiency (cd / A) Lifetime T95 (hr) Emission Color Example 1 Compound 1-1 Compound 2-13.5321.36178 Red Example 2 Compound 1-2 Compound 2-13.4621.90170 Red Example 3 Compound 1-3 Compound 2-13.4222.27183 Red Example 4 Compound 1-4 Compound 2-13.2823.29174 Red Example 5 Compound 1-5 Compound 2-13.3723.28183 Red Example 6 Compound 1-6 Compound 2-13.3322.65180 Red Example 7 Compound 1-7 Compound 2-13.35 20.76 191 Red Example 8 Compound 1-8 Compound 2-13.41 22.30 210 Red Example 9 Compound 1-1 Compound 2-23.43 20.93 196 Red Example 10 Compound 1-2 Compound 2-23.53 22.48 175 Red Example 11 Compound 1-3 Compound 2-23.43 20.84 191 Red Example 12 Compound 1-4 Compound 2-23.37 20.73 186 Red Example 13 Compound 1-5 Compound 2-23.56 22.22 175 Red Example 14 Compound 1-6 2-23.5321.79167 Red Example 15 Compound 1-7 Compound 2-23.3923.38191 Red Example 16 Compound 1-8 Compound 2-23.4421.01219 Red Example 17 Compound 1-1 Compound 2-33.3423.18187 Red Example 18 Compound 1-2 Compound 2-33.3722.36189 Red Example 19 Compound 1-3 Compound 2-33.4222.38181 Red Example 20 Compound 1-4 Compound 2-33.4323.09194 Red Example 21 Compound 1-5 Compound 2-33.3420.94177 Red Example 22 Compound 1-6 Compound 2-33.4121.20194 Red Example 23 Compound 1-7 Compound 2-33.4321.17191 Red Example 24 Compound 1-8 Compound 2-33.4322.41208 Red Example 25 Compound 1-1 Compound 2-43.4722.38170 Red Example 26 Compound 1-2 Compound 2-43.4122.00179 Red Example 27 Compound 1-3 Compound 2-43.5422.28171 Red Example 28 Compound 1-4 Compound 2-43.4022.23169 Red Example 29 Compound 1-5 Compound 2-43.5221.33177 Red Example 30 Compound 1-6 Compound 2-43.5720.48167 Red Example 31 Compound 1-7 Compound 2-43.5521.09164 Red Example 32 Compound 1-8 Compound 2-43.5222.35196 Red Comparative Example 1 HT2 Compound 2-13.7217.91123 Red Comparative Example 2 HT3 Compound 2-13.6917.64120 Red Comparative Example 3 HT2 Compound 2-23.7618.23126 Red Comparative Example 4 HT3 Compound 2-23.7117.84119 Red Comparative Example 5 HT5 Compound 2-13.9416.52117 Red Comparative Example 6 HT6 Compound 2-13.8317.47106 Red Comparative Example 7 HT7 Compound 2-14.0816.32132 Red Comparative Example 8 Compound 1-1ET12.6119.65105 Red Comparative Example 9 Compound 1-3ET12.7019.51108 Red Comparative Example 10 Compound 1-1ET24.0119.13128 Red Comparative Example 11 Compound 1-7ET33.9518.89139 Red Comparative Example 12 HT4ET13.9418.06106 Red.

[0521] As shown in Table 1 above, an organic light-emitting device using the compound of the present invention as a hole transport assist layer and an electron transport and injection layer exhibited excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light-emitting device.

[0522] When the compound of the present invention was used as a hole transport assist layer and an electron transport and injection layer, the driving voltage was lower and the efficiency increased compared to the comparative example material, indicating that energy transfer from the host to the red dopant was effectively achieved. Furthermore, it was found that lifespan characteristics could be improved while maintaining high efficiency. This can ultimately be attributed to the fact that the compound of the present invention has higher stability for electrons and holes than the comparative example compound.

[0523] In conclusion, it can be confirmed that when the compound of the present invention is used as a hole transport assist layer and an electron transport and injection layer of a red light-emitting layer, the driving voltage, luminous efficiency, and / or lifespan characteristics of an organic light-emitting device can be improved.

[0524] Specifically, Examples 1 to 32, which use a compound of Formula 1 in the hole transport assist layer of Table 1, exhibit superior effects in terms of driving voltage, luminous efficiency, and / or lifespan characteristics of an organic light-emitting device compared to Comparative Examples 1 to 7, which use a compound of Formula 1 in which -L2-Ar1 or -L3-Ar2 is a heteroaryl group (dibenzofuran or carbazole group) in the hole transport assist layer. This is because when the core of Formula 1 forms a phenanthrene-linker (aryl)-amine bond structure, and when a heteroaryl group is bonded when used as a hole transport layer in a red light-emitting layer, the injection or movement of electrons is slowed down, which can lead to an increase in voltage, a decrease in efficiency, and / or a decrease in lifespan.

[0525] In addition, Examples 1 to 32, which used the compound of Formula 2 in the electron transport and injection layer of Table 1, exhibit superior effects in terms of driving voltage, luminous efficiency / and / or lifetime characteristics of the organic light-emitting diode compared to Comparative Examples 10 and 11, which used a compound not containing -CN groups in the electron transport and injection layer. This is because the example compounds showed improvements in electron injection and mobility in the electron transport and injection layer when -CN groups were bonded to the core positions, resulting in increased voltage, increased efficiency, and / or increased lifetime.

[0526] Furthermore, it was confirmed that the combination of the compound of Chemical Formula 1 and the compound of Chemical Formula 2 creates further synergy in the red light-emitting layer, lowering the driving voltage and increasing efficiency and lifespan.

Claims

1. Anode; Cathode; A first organic layer provided between the anode and the cathode; and It includes a second organic layer provided between the cathode and the first organic layer, and The first organic layer comprises a compound represented by the following chemical formula 1, and An organic light-emitting device in which the second organic layer comprises a compound represented by the following chemical formula 2: [Chemical Formula 1] In the above chemical formula 1, Ar1 and Ar2 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a condensation ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and L2 and L3 are the same or different from each other, and each is independently directly bonded; or are substituted or unsubstituted arylene groups, and R1 to R3 are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and a, b, and c are each independently integers from 0 to 3, and if a is 2 or greater, 2 or more L1s are equal to or different from each other, if b is 2 or greater, 2 or more L2s are equal to or different from each other, and if c is 2 or greater, 2 or more L3s are equal to or different from each other, and r2 and r3 are each independently integers from 0 to 4, and if r2 is 2 or greater, 2 or more R2s are equal to or different from each other, and if r3 is 2 or greater, 2 or more R3s are equal to or different from each other, and [Chemical Formula 2] In the above chemical formula 2, Ar3 and Ar4 are the same or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and L4 to L6 are the same or different from one another, and each is independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and R4 to R7 are the same or different from one another, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and d, e, and f are each independently integers from 0 to 3, and if d is 2 or greater, L4 of 2 or greater is equal to or different from each other, if e is 2 or greater, L5 of 2 or greater is equal to or different from each other, and if f is 2 or greater, L6 of 2 or greater is equal to or different from each other, and r4 and r5 are each independently integers from 0 to 4, and if r4 is 2 or greater, 2 or more R4s are equal to or different from each other, and if r5 is 2 or greater, 2 or more R5s are equal to or different from each other, and r6 and r7 are each independently integers from 0 to 3, and if r6 is 2 or more, 2 or more R6s are the same or different from each other, and if r7 is 2 or more, 2 or more R7s are the same or different from each other.

2. In Claim 1, Organic light-emitting diodes wherein L1 to L3 are the same or different from each other and each independently represented by any one of the following structural formulas: In the above structural formula, The dotted line indicates the connection location, The site substituted with hydrogen can be replaced with deuterium.

3. In Claim 1, An organic light-emitting device in which Ar1 and Ar2 are the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted adamantyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted spirobifluorenyl group; or a substituted or unsubstituted tetrahydronaphthyl group.

4. In Claim 1, An organic light-emitting device wherein L2 and L3 are the same or different from each other and are each independently directly bonded; a divalent phenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent biphenyl group substituted or unsubstituted with deuterium; a divalent terphenyl group substituted or unsubstituted with deuterium; a divalent naphthyl group substituted or unsubstituted with deuterium; a divalent fluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent spirobifluorenyl group substituted or unsubstituted with deuterium; or a divalent phenanthrenyl group substituted or unsubstituted with deuterium.

5. In Claim 1, An organic light-emitting device in which R1 to R3 are the same or different from each other and each independently is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; 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.

6. In Claim 1, An organic light-emitting device in which Ar3 and Ar4 are the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted adamantyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

7. In Claim 1, L4 to L6 are the same or different from one another and are each independently directly bonded; a divalent phenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent biphenyl group substituted or unsubstituted with deuterium; a divalent terphenyl group substituted or unsubstituted with deuterium; a divalent naphthyl group substituted or unsubstituted with deuterium; a divalent fluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; a divalent spirobifluorenyl group substituted or unsubstituted with deuterium; a divalent phenanthrenyl group substituted or unsubstituted with deuterium; a divalent carbazole group substituted or unsubstituted with deuterium; a divalent dibenzofuranyl group substituted or unsubstituted with deuterium; An organic light-emitting device that is a divalent dibenzothiophenyl group substituted or unsubstituted with deuterium.

8. In Claim 1, An organic light-emitting device in which R4 to R7 are the same or different from each other and each independently is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; 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.

9. In Claim 1, The above chemical formula 1 is an organic light-emitting device that is any one of the following compounds: .

10. In Claim 1, The above chemical formula 2 is an organic light-emitting device that is any one of the following compounds: .

11. In Claim 1, An organic light-emitting device in which the first organic layer is a hole injection layer, a hole transport layer, a hole injection and transport layer, a hole transport auxiliary layer, or an electron suppression layer.

12. In Claim 1, An organic light-emitting device in which the second organic layer is an electron transport layer, an electron injection layer, or an electron transport and injection layer.

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