Organic light emitting device

Abstract

The present specification relates to an organic light-emitting device comprising a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2. The organic light emitting device includes an anode, a cathode, and a first organic material layer and a second organic material layer disposed between the anode and the cathode, the first organic material layer including a compound represented by the following Chemical Formula 1, and the second organic material layer including a compound represented by the following Chemical Formula 2. The organic light-emitting device described in the present specification has the effects of low driving voltage, high efficiency and / or long lifespan by containing a compound represented by Chemical Formula 1 in a first organic material layer and a compound represented by Chemical Formula 2 in a second organic material layer. [Chemical Formula 1] [Chemical Formula 2]

Description

Technical Field

[0001] This application claims priority to Korean Patent Application No. 10-2024-0125574, filed with the Korean Patent Office on September 13, 2024, the entire contents of which are incorporated herein by reference.

[0002] This specification relates to organic light-emitting devices. Background Technology

[0003] In this specification, organic light-emitting devices (OLEDs) are light-emitting devices that utilize organic semiconductor materials and require the exchange of holes and / or electrons between electrodes and the organic semiconductor material. Based on their working principles, OLEDs can be broadly classified into two types. The first type utilizes photons flowing into the device from an external light source to form excitons in the organic layer. These excitons separate into electrons and holes, which are then transferred to different electrodes, serving as a current source (voltage source). The second type involves applying voltage or current to two or more electrodes, thereby injecting holes and / or electrons into the organic semiconductor layer that forms the interface with the electrodes. The OLED operates through the injected electrons and holes.

[0004] Organic light emission (OLED) typically refers to the phenomenon of converting electrical energy into light energy using organic materials. OLED devices generally have a structure comprising an anode and a cathode, with an organic layer between them. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multi-layered structure composed of different materials, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron suppression layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed. When these excitons re-enter the ground state, they emit light. Such OLEDs are known to possess characteristics such as self-emission, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

[0005] In order to fully utilize the excellent characteristics of the organic light-emitting devices mentioned above, the materials constituting the organic layer inside the device, such as hole injection materials, hole transport materials, light-emitting materials, electron suppression materials, electron transport materials, and electron injection materials, need to be backed by stable and effective materials. Therefore, there is a continuous need to develop new materials. Summary of the Invention

[0006] Technical issues

[0007] This specification describes organic light-emitting devices.

[0008] Solution to the problem

[0009] One embodiment of this specification provides an organic light-emitting device, comprising: an anode, a cathode, and a first organic layer and a second organic layer disposed between the anode and the cathode, 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.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] Ar1 and Ar2 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or a fused ring of substituted or unsubstituted aromatic ring and aliphatic ring.

[0014] L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted divalent aryl group, or a substituted or unsubstituted divalent heteroaryl group.

[0015] R1 is hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0016] R2 and R3 may be the same or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or when p or q is 2 or more, they may combine with adjacent groups to form substituted or unsubstituted rings.

[0017] a, b, and c are integers from 0 to 3. When a is 2 or higher, two or more L1 values ​​are the same or different from each other. When b is 2 or higher, two or more L2 values ​​are the same or different from each other. When c is 2 or higher, two or more L3 values ​​are the same or different from each other.

[0018] p and q are integers from 0 to 4. When p is 2 or more, two or more R2 values ​​are the same or different from each other. When q is 2 or more, two or more R3 values ​​are the same or different from each other.

[0019] [Chemical Formula 2]

[0020]

[0021] In the above chemical formula 2,

[0022] Ar3 is a substituted or unsubstituted heteroaryl group.

[0023] Ar4 is a substituted or unsubstituted polycyclic aryl group.

[0024] L4 and L5 may be the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted divalent aryl group.

[0025] R4 is either hydrogen or deuterium.

[0026] d and e are integers from 0 to 3. When d is 2 or higher, two or more L4s are either the same or different. When e is 2 or higher, two or more L5s are either the same or different.

[0027] r is an integer from 0 to 3. When r is 2 or more, two or more R4s are the same or different from each other.

[0028] Invention Effects

[0029] The organic light-emitting device described in this specification has the effects of low driving voltage, high efficiency and / or long lifespan by including a compound represented by chemical formula 1 in the first organic layer and a compound represented by chemical formula 2 in the second organic layer. Attached Figure Description

[0030] Figure 1 The illustration shows 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 stacked in sequence.

[0031] Figure 2 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a hole transport auxiliary layer 5, a light-emitting layer 6, a hole suppression layer 7, an electron transport and injection layer 8, and a cathode 9 stacked in sequence.

[0032] Figure 3 MS plot of compound A.

[0033] Symbol Explanation

[0034] 1: Substrate

[0035] 2: Anode

[0036] 3: Hole injection layer

[0037] 4: Hole transport layer

[0038] 5: Hole transport auxiliary layer

[0039] 6: Emissive layer

[0040] 7: Hole Suppression Layer

[0041] 8: Electron transport and injection layer

[0042] 9: Cathode

[0043] 21: First organic layer

[0044] 22: Second organic layer Detailed Implementation

[0045] The following is a more detailed description of this instruction manual.

[0046] In this specification, when a part is indicated to "include" a certain component, unless otherwise stated, it means that other components may be included, rather than excluded.

[0047] In this specification, when it is stated that a component is "on" another component, it includes not only the case where one component is connected to another component, but also the case where there are other components between the two components.

[0048] In this specification, "adjacent" groups can refer to substituents that are directly bonded to the atom substituted by the substituent, substituents that are stereomorphically closest to the substituent, or other substituents that are substituted to the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon atom in an aliphatic ring can be interpreted as "adjacent" groups.

[0049] In this specification, "containing deuterium," "deuterated," or "deuterated" means that hydrogen at substituted positions in a compound is replaced with deuterium. In this specification, "overdeuterated" means a compound or group in which all hydrogen atoms in the molecule are replaced with deuterium, and has the same meaning as "100% deuterated."

[0050] In this specification, "X% deuterated," "degree of deuteration X%," or "deuteration rate X%" means that X% of the hydrogens at the substituted positions in the structure are replaced with deuterium. The "deuteration rate (%)" of a compound or group can be expressed as (number of deuteriums) / (number of deuteriums + number of hydrogens) * 100 (%). For example, when the structure is dibenzofuran, "25% deuterated" of the aforementioned dibenzofuran, "degree of deuteration 25%" of the aforementioned dibenzofuran, or "deuteration rate 25%" of the aforementioned dibenzofuran means that two of the eight hydrogens at the substituted positions in the aforementioned dibenzofuran are replaced with deuterium.

[0051] In this specification, "degree of deuteration" or "deuteration substitution rate" can be determined by nuclear magnetic resonance spectroscopy (NMR spectroscopy). 1 The assay was confirmed using known methods such as ¹H NMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry).

[0052] Specifically, through nuclear magnetic resonance spectroscopy (NMR spectroscopy) 1 When analyzing "degree of deuteration" or "deuteration substitution rate" using ¹H NMR, DMF (dimethylformamide) can be added as an internal standard. 1 The integration ratio on H NMR is used to calculate the degree of deuteration or the rate of deuteration substitution from the total peak.

[0053] Additionally, when analyzing "degree of deuteration" or "deuteration substitution rate" using TLC / MS (thin-layer chromatography / mass spectrometry), the substitution rate can be calculated based on the maximum value (intermediate value) of the molecular weight distribution at the end of the reaction. For example, when analyzing the degree of deuteration of compound A below, the molecular weight of the starting material is 506. When specifying... Figure 3 When the maximum molecular weight (median value) of compound A in the MS chart is 527, 21 of the 26 substituted hydrogen positions in the starting material are replaced with deuterium, so it can be calculated that about 81% of the hydrogen is deuterated.

[0054]

[0055] In this specification, D represents deuterium.

[0056] In this specification, [] Dn The parentheses indicate that the structure contains n deuterium atoms. That is, n represents the number of substituted deuterium atoms in the compound within the parentheses, and n is an integer greater than or equal to 1. The maximum value of n is the same as the number of substituted hydrogen atoms in the compound within the parentheses. For example, if the compound within the parentheses has 46 substituted hydrogen atoms, then n is an integer from 1 to 46.

[0057] In this specification, the term "substitution" refers to the replacement of a hydrogen atom on a carbon atom of a compound with another substituent. There is no limitation on the position of substitution, as long as the hydrogen atom can be substituted, that is, the position where the substituent can be substituted. When two or more substituents are substituted, the two or more substituents can be the same or different from each other.

[0058] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen groups, cyano (-CN), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heterocyclic groups, or substituted by two or more substituents linked together from the substituents exemplified above, or having no substituents.

[0059] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, cyano (-CN), alkyl with 1 to 10 carbon atoms, and aryl with 6 to 30 carbon atoms, or substituted by two or more substituents linked together as exemplified above, or without any substituents.

[0060] In this specification, the connection of two or more substituents refers to the connection of the hydrogen of any one substituent with other substituents. For example, the connection of two substituents can be a phenyl group connected to a naphthyl group, thus forming... Such substituents. Furthermore, the connection of three substituents includes not only a sequential connection of (substituent 1)-(substituent 2)-(substituent 3), but also a connection of (substituent 2) and (substituent 3) on (substituent 1). For example, phenyl, naphthyl, and isopropyl can be linked to form... Such substituents. The above definition also applies to connections of four or more substituents.

[0061] Examples of the substituents mentioned above are given below, but are not limited thereto.

[0062] Examples of halogen groups in this specification include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0063] In this specification, the alkyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited to these.

[0064] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group with 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc., are used, but are not limited to these.

[0065] In this specification, aryl is not particularly limited, but is preferably an aryl with 6 to 60 carbon atoms, and can be a monocyclic aryl or a polycyclic aryl. According to one embodiment, the aryl has 6 to 30 carbon atoms. According to another embodiment, the aryl has 6 to 20 carbon atoms. The monocyclic aryl may contain two or more benzene rings. As the monocyclic aryl, it can be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. The polycyclic aryl refers to a structure formed by the fusion of two or more benzene rings. As the polycyclic aryl, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, triphenylene, etc. It includes fluorenyl, fluoranyl, fluoreneyl, etc., but is not limited to these.

[0066] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure.

[0067] When the aforementioned fluorene group is replaced, it can become Isospirofluorene group; (9,9-dimethylfluorene) and Substituted fluorenyl groups such as (9,9-diphenylfluorenyl) are used. However, this is not a limitation.

[0068] In this specification, a heteroaryl group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. The heteroaryl group can be monocyclic or polycyclic. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of heterocyclic groups include pyridyl, pyrrolithyl, pyrimidinyl, pyridazinyl, furanyl, thiopheneyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, etc., but are not limited to these.

[0069] In this specification, arylene refers to a divalent aryl group. The description of aryl groups above can be used as an example of aryl groups other than divalent.

[0070] In this specification, heteroaryl refers to a divalent heteroaryl group. In addition to being divalent, the above description of heteroaryl groups can be used.

[0071] In this specification, "ring" refers to a hydrocarbon ring or heterocycle in the context of a substituted or unsubstituted ring formed by the combination of adjacent groups with each other.

[0072] The aforementioned hydrocarbon ring can be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a fused ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring. The above description regarding aryl groups applies to the aforementioned aromatic hydrocarbon rings, and the above description regarding cycloalkyl groups applies to the aforementioned aliphatic hydrocarbon rings. Furthermore, the above-described structure of fused aryl and cycloalkyl groups is applicable to fused aromatic and aliphatic hydrocarbon rings.

[0073] In this specification, the term "forming a ring by bonding with adjacent groups" means forming a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle, or a fused ring thereof by bonding with adjacent groups. The aforementioned hydrocarbon ring refers to a ring composed only of carbon and hydrogen atoms. The aforementioned heterocycle refers to a ring containing one or more atoms selected from N, O, P, S, Si, and Se. In this specification, the aforementioned aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle can be monocyclic or polycyclic.

[0074] In this specification, aliphatic hydrocarbon rings refer to non-aromatic rings composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene, but are not limited to these.

[0075] In this specification, aromatic hydrocarbon rings refer to aromatic rings composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenatene, pyrene, and tetraphenylene. The aromatic hydrocarbon rings include, but are not limited to, pentane, fluorene, indene, acenaphthene, benzo[a]fluorene, spirofluorene, etc. In this specification, the aromatic hydrocarbon ring can be interpreted in the same way as the aryl group.

[0076] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, and 1,4-dioxane. Alkane (1,4-dioxane), pyrrolidine, piperidine, morpholine, oxepane Azahexacyclic octane Thioheterocyclic octane etc., but not limited to this.

[0077] In this specification, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, etc. azole, isotonic azole, thiazole, isothiazole, triazole Diazole, thiadiazole, dithiazole, tetraazole, pyran, thiaran, diazine Azine, thiazide, diazine Alkenes, triazines, tetraazines, isoquinoline, quinoline, quinones, quinazoline, quinoxaline, naphthidine, acridine, phenanthridine, diazanaphthalene, triazaindene, indole, indolezine, benzothiazole, benzo[] azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenazine It includes aziridines, indobenzocarbazole, indobenzocarbazole, etc., but is not limited to these.

[0078] In this specification, "energy level" refers to the magnitude of energy. Therefore, an energy level is interpreted as the absolute value of that energy. For example, a low or deep energy level refers to an absolute increase in energy from the vacuum level in the negative direction.

[0079] In this specification, HOMO (highest occupied molecular orbital) refers to the molecular orbital function (highest energy region) where electrons are located in the region where they can participate in bonding. LUMO (lowest unoccupied molecular orbital) refers to the molecular orbital function (lowest unoccupied molecular orbital) where electrons are located in the antibonding region. The HOMO energy level refers to the distance from the vacuum energy level to the HOMO. Similarly, the LUMO energy level refers to the distance from the vacuum energy level to the LUMO.

[0080] In this specification, the band gap refers to the energy difference between the HOMO and LUMO levels, i.e., the HOMO-LUMO gap.

[0081] In this specification, the HOMO level can be measured at atmospheric pressure using a photoelectron spectrometer (manufactured by Riken Keiki Co., Ltd.: AC3), and the LUMO level can be calculated using wavelength values ​​measured by photoluminescence (PL).

[0082] In this specification, unless otherwise defined, all technical and scientific terms used have the same meaning as commonly understood by those skilled in the art. Methods and materials similar to or equivalent to those described herein may be used to implement or test embodiments of the invention, but suitable methods and materials are described later. 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 mentioned, this specification, including its definitions, takes precedence. Furthermore, materials, methods, and embodiments are illustrative only and not intended to be limiting.

[0083] The preferred embodiments of the present invention will now be described in detail. However, the embodiments of the present invention can be modified in various ways, and the scope of the present invention is not limited to the embodiments described below.

[0084] The organic light-emitting device of the present invention is characterized by simultaneously comprising a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2. The organic light-emitting device of the present invention exhibits the effects of low voltage, high efficiency, and / or long lifetime. More specifically, in the organic light-emitting device simultaneously comprising the compound of Chemical Formula 1 and the compound of Chemical Formula 2, the balance of holes and electrons is appropriate, thus exhibiting the effects of low voltage, high efficiency, and / or long lifetime. In particular, when the compound of Chemical Formula 1 is used as the hole transport material, the HOMO energy level of the compound of Chemical Formula 1 is low, and the energy barrier between the emitting layer and the hole transport layer is reduced, thus allowing for appropriate adjustment of the potential barrier between the emitting layer and the hole transport layer. Furthermore, when the compound of Chemical Formula 2 is used as the electron transport material, the LUMO energy level of the compound of Chemical Formula 2 is high, and the energy barrier between the emitting layer and the electron transport layer is reduced, thus allowing for appropriate adjustment of the potential barrier between the emitting layer and the electron transport layer.

[0085] The compounds of chemical formula 1 will now be described in detail.

[0086] [Chemical Formula 1]

[0087]

[0088] In the above chemical formula 1,

[0089] Ar1 and Ar2 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or a fused ring of substituted or unsubstituted aromatic ring and aliphatic ring.

[0090] L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted divalent aryl group, or a substituted or unsubstituted divalent heteroaryl group.

[0091] R1 is hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0092] R2 and R3 may be the same or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or when p or q is 2 or more, they can combine with adjacent groups to form substituted or unsubstituted rings.

[0093] a, b, and c are integers from 0 to 3. When a is 2 or higher, two or more L1 values ​​are the same or different from each other. When b is 2 or higher, two or more L2 values ​​are the same or different from each other. When c is 2 or higher, two or more L3 values ​​are the same or different from each other.

[0094] p and q are integers from 0 to 4. When p is 2 or more, two or more R2s are the same or different from each other. When q is 2 or more, two or more R3s are the same or different from each other.

[0095] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each may independently be hydrogen, deuterium, a cyclic alkyl group with 3 to 60 substituted or unsubstituted carbon atoms, an aryl group with 6 to 60 substituted or unsubstituted carbon atoms, a heteroaryl group with 2 to 60 substituted or unsubstituted carbon atoms, or a fused ring group of aromatic and aliphatic rings with 8 to 60 substituted or unsubstituted carbon atoms.

[0096] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each may independently be hydrogen, deuterium, a cyclic alkyl group with 3 to 30 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, a heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms, or a fused ring group of aromatic and aliphatic rings with 8 to 30 substituted or unsubstituted carbon atoms.

[0097] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each may independently be hydrogen, deuterium, a cyclic alkyl group with 3 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 20 substituted or unsubstituted carbon atoms, a heteroaryl group with 2 to 20 substituted or unsubstituted carbon atoms, or a fused ring group of aromatic and aliphatic rings with 8 to 20 substituted or unsubstituted carbon atoms.

[0098] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0099] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each may independently be hydrogen; deuterium; adamantyl alkyl substituted or unsubstituted with deuterium; phenyl 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 substituted or unsubstituted with deuterium; terphenyl substituted or unsubstituted with deuterium; naphthyl substituted or unsubstituted with deuterium; fluorenyl substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; spirodifluorenyl substituted or unsubstituted with deuterium; phenanthrene substituted or unsubstituted with deuterium; tetrahydronaphthyl substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms; carbazolyl substituted or unsubstituted with deuterium; dibenzofuranyl substituted or unsubstituted with deuterium; or dibenzothiophene substituted or unsubstituted with deuterium.

[0100] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each may independently be a divalent aryl group with 6 to 60 carbon atoms that is directly bonded, substituted or unsubstituted, or a divalent heteroaryl group with 2 to 60 carbon atoms that is substituted or unsubstituted.

[0101] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each may independently be a divalent aryl group with 6 to 30 carbon atoms that is directly bonded, substituted or unsubstituted, or a divalent heteroaryl group with 2 to 30 carbon atoms that is substituted or unsubstituted.

[0102] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each may independently be a divalent aryl group with 6 to 20 carbon atoms that is directly bonded, substituted or unsubstituted, or a divalent heteroaryl group with 2 to 20 carbon atoms that is substituted or unsubstituted.

[0103] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each may independently be a directly bonded, substituted or unsubstituted divalent phenyl, substituted or unsubstituted divalent biphenyl, substituted or unsubstituted divalent triphenyl, substituted or unsubstituted divalent naphthyl, substituted or unsubstituted divalent fluorenyl, substituted or unsubstituted divalent spirodifluorenyl, substituted or unsubstituted divalent phenanthryl, substituted or unsubstituted divalent carbazolyl, substituted or unsubstituted divalent dibenzofuranyl, or substituted or unsubstituted divalent dibenzothiophene.

[0104] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each may independently be directly bonded; a divalent phenyl 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 substituted or unsubstituted with deuterium; a divalent terphenyl substituted or unsubstituted with deuterium; a divalent naphthyl substituted or unsubstituted with deuterium; a divalent fluorenyl 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 spirodifluorenyl substituted or unsubstituted with deuterium; a divalent phenanthryl substituted or unsubstituted with deuterium; a divalent carbazolyl substituted or unsubstituted with deuterium; a divalent dibenzofuranyl substituted or unsubstituted with deuterium; or a divalent dibenzothiopheneyl substituted or unsubstituted with deuterium.

[0105] In one embodiment of this specification, L1 can be a substituted or unsubstituted divalent aryl group. Compounds of Formula 1 with L1 being a divalent aryl group exhibit excellent electron blocking effects, showing lower voltage, higher efficiency, and / or longer lifetime in organic light-emitting devices compared to the case where L1 is directly bonded.

[0106] In one embodiment of this specification, L1 can be a divalent aryl group with 6 to 60 carbon atoms, either substituted or unsubstituted.

[0107] In one embodiment of this specification, L1 can be a divalent aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0108] In one embodiment of this specification, L1 can be a divalent aryl group with 6 to 20 carbon atoms, either substituted or unsubstituted.

[0109] In one embodiment of this specification, L1 may be a substituted or unsubstituted divalent phenyl, a substituted or unsubstituted divalent biphenyl, or a substituted or unsubstituted divalent naphthyl.

[0110] In one embodiment of this specification, L1 may be a divalent phenyl substituted or unsubstituted with deuterium or an aryl group having 6 to 12 carbon atoms, a divalent biphenyl substituted or unsubstituted with deuterium, or a divalent naphthyl substituted or unsubstituted with deuterium.

[0111] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and each may independently be a divalent aryl group with 6 to 60 carbon atoms that is directly bonded, substituted or unsubstituted, or a divalent heteroaryl group with 2 to 60 carbon atoms that is substituted or unsubstituted.

[0112] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and each may independently be a divalent aryl group with 6 to 30 carbon atoms that is directly bonded, substituted or unsubstituted, or a divalent heteroaryl group with 2 to 30 carbon atoms that is substituted or unsubstituted.

[0113] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and each may independently be a directly bonded, substituted or unsubstituted divalent aryl group with 6 to 20 carbon atoms, or a substituted or unsubstituted divalent heteroaryl group with 2 to 20 carbon atoms.

[0114] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and each may independently be a directly bonded, substituted or unsubstituted divalent phenyl, substituted or unsubstituted divalent biphenyl, substituted or unsubstituted divalent triphenyl, substituted or unsubstituted divalent naphthyl, substituted or unsubstituted divalent fluorenyl, substituted or unsubstituted divalent spirodifluorenyl, substituted or unsubstituted divalent phenanthryl, substituted or unsubstituted divalent carbazolyl, substituted or unsubstituted divalent dibenzofuranyl, or substituted or unsubstituted divalent dibenzothiophene.

[0115] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and each may independently be directly bonded; a divalent phenyl 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 substituted or unsubstituted with deuterium; a divalent terphenyl substituted or unsubstituted with deuterium; a divalent naphthyl substituted or unsubstituted with deuterium; a divalent fluorenyl 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 spirodifluorenyl substituted or unsubstituted with deuterium; a divalent phenanthryl substituted or unsubstituted with deuterium; a divalent carbazolyl substituted or unsubstituted with deuterium; a divalent dibenzofuranyl substituted or unsubstituted with deuterium; or a divalent dibenzothiopheneyl substituted or unsubstituted with deuterium.

[0116] In one embodiment of this specification, R1 can be hydrogen, deuterium, aryl with 6 to 60 substituted or unsubstituted carbon atoms, or heteroaryl with 2 to 60 substituted or unsubstituted carbon atoms.

[0117] In one embodiment of this specification, R1 can be hydrogen, deuterium, aryl with 6 to 30 substituted or unsubstituted carbon atoms, or heteroaryl with 2 to 30 substituted or unsubstituted carbon atoms.

[0118] In one embodiment of this specification, R1 can be hydrogen, deuterium, aryl with 6 to 20 substituted or unsubstituted carbon atoms, or heteroaryl with 2 to 20 substituted or unsubstituted carbon atoms.

[0119] In one embodiment of this specification, R1 can be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted fluorenyl, or substituted or unsubstituted carbazolyl.

[0120] In one embodiment of this specification, R1 can be 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 carbazolyl group substituted or unsubstituted with deuterium.

[0121] In one embodiment of this specification, R1 can be hydrogen, deuterium, or a phenyl group that is either deuterated or unsubstituted.

[0122] In one embodiment of this specification, R2 and R3 may be the same as or different from each other, and each may independently be hydrogen, deuterium, aryl with 6 to 60 substituted or unsubstituted carbon atoms, or heteroaryl with 2 to 60 substituted or unsubstituted carbon atoms, or when p or q is 2 or more, and may combine with adjacent groups to form a ring with 2 to 60 substituted or unsubstituted carbon atoms.

[0123] In one embodiment of this specification, R2 and R3 may be the same as or different from each other, and each independently consists of hydrogen, deuterium, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms, or when p or q is 2 or more, and can combine with adjacent groups to form a ring with substituted or unsubstituted carbon atoms with 2 to 30 carbon atoms.

[0124] In one embodiment of this specification, R2 and R3 may be the same as or different from each other, and each independently consists of hydrogen, deuterium, substituted or unsubstituted aryl group with 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl group with 2 to 20 carbon atoms, or when p or q is 2 or more, and can combine with adjacent groups to form a ring with substituted or unsubstituted carbon atoms with 2 to 20 carbon atoms.

[0125] In one embodiment of this specification, R2 and R3 may be the same as or different from each other, and each may independently be hydrogen, deuterium, aryl with 6 to 20 substituted or unsubstituted carbon atoms, or heteroaryl with 2 to 20 substituted or unsubstituted carbon atoms.

[0126] In one embodiment of this specification, when p is 2 or more, R2 can combine with adjacent groups to form an aromatic hydrocarbon ring with 6 to 20 carbon atoms.

[0127] In one embodiment of this specification, when q is 2 or more, R3 can combine with adjacent groups to form an aromatic hydrocarbon ring with 6 to 20 carbon atoms.

[0128] In one embodiment of this specification, R2 and R3 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted fluorenyl, or substituted or unsubstituted carbazole, or when p or q is 2 or more, they may combine with adjacent groups to form substituted or unsubstituted benzene rings.

[0129] In one embodiment of this specification, R2 and R3 may be the same as or different from each other, and each independently represents hydrogen; deuterium; a phenyl group that is substituted or unsubstituted with deuterium; an alkyl group that is 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 carbazolyl group that is substituted or unsubstituted with deuterium; or when p or q is 2 or more, it may combine with adjacent groups to form a benzene ring that is substituted or unsubstituted with deuterium.

[0130] In one embodiment of this specification, R2 and R3 may be the same or different from each other, each being independently hydrogen, deuterium, or a phenyl group that is substituted or unsubstituted with deuterium, or when p or q is 2 or more, they can combine with adjacent groups to form a benzene ring that is substituted or unsubstituted with deuterium.

[0131] In one embodiment of this specification, R2 and R3 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted fluorenyl, or substituted or unsubstituted carbazolyl.

[0132] In one embodiment of this specification, R2 and R3 may be the same as or different from each other, and each may independently be 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 carbazolyl group substituted or unsubstituted with deuterium.

[0133] In one embodiment of this specification, R2 and R3 may be the same as or different from each other, and each may independently be hydrogen, deuterium, or a phenyl substituted with or unsubstituted with deuterium.

[0134] In one embodiment of this specification, R1 to R3 may be the same as or different from each other, and each may independently be 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 carbazolyl group substituted or unsubstituted with deuterium.

[0135] In one embodiment of this specification, R1 to R3 may be the same as or different from each other, and each may independently be hydrogen, deuterium, or a phenyl substituted with or unsubstituted with deuterium.

[0136] In one embodiment of this specification, a is an integer from 0 to 3. When a is 2 or more, two or more L1s are the same or different from each other.

[0137] In one embodiment of this specification, a is an integer from 0 to 3.

[0138] In one embodiment of this specification, a is 3.

[0139] In one embodiment of this specification, a is 2.

[0140] In one embodiment of this specification, a is 1.

[0141] In one embodiment of this specification, a is 0.

[0142] In one embodiment of this specification, b is an integer from 0 to 3. When b is 2 or more, two or more L2s are the same or different from each other.

[0143] In one embodiment of this specification, b is an integer from 0 to 3.

[0144] In one embodiment of this specification, b is 3.

[0145] In one embodiment of this specification, b is 2.

[0146] In one embodiment of this specification, b is 1.

[0147] In one embodiment of this specification, b is 0.

[0148] In one embodiment of this specification, c is an integer from 0 to 3. When c is 2 or more, two or more L3s are the same or different from each other.

[0149] In one embodiment of this specification, c is an integer from 0 to 3.

[0150] In one embodiment of this specification, c is 3.

[0151] In one embodiment of this specification, c is 2.

[0152] In one embodiment of this specification, c is 1.

[0153] In one embodiment of this specification, c is 0.

[0154] In one embodiment of this specification, p is an integer from 0 to 4. When p is 2 or more, two or more R2s are the same or different from each other.

[0155] In one embodiment of this specification, p is an integer from 0 to 4.

[0156] In one embodiment of this specification, p is 4.

[0157] In one embodiment of this specification, p is 3.

[0158] In one embodiment of this specification, p is 2.

[0159] In one embodiment of this specification, p is 1.

[0160] In one embodiment of this specification, p is 0.

[0161] In one embodiment of this specification, q is an integer from 0 to 4. When q is 2 or more, two or more R3s are the same or different from each other.

[0162] In one embodiment of this specification, q is an integer from 0 to 4.

[0163] In one embodiment of this specification, q is 4.

[0164] In one embodiment of this specification, q is 3.

[0165] In one embodiment of this specification, q is 2.

[0166] In one embodiment of this specification, q is 1.

[0167] In one embodiment of this specification, q is 0.

[0168] In one embodiment of this specification, the compound represented by the above chemical formula 1 contains at least one deuterium.

[0169] In one embodiment of this specification, the compound represented by Chemical Formula 1 is at least 40% replaced by deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted with more than 50% deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted with more than 60% deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted with more than 70% deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted with more than 80% deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted with more than 90% deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 is substituted with 100% deuterium.

[0170] In one embodiment of this specification, the compound represented by Chemical Formula 1 contains 40% to 60% deuterium. In another embodiment, the compound represented by Chemical Formula 1 contains 40% to 80% deuterium. In another embodiment, the compound represented by Chemical Formula 1 contains 60% to 80% deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 contains 80% to 100% deuterium.

[0171] Specifically, the physicochemical properties of deuterium, such as bond length, are different from those of hydrogen. Compared with the CH bond, the CD bond has a smaller stretching amplitude, so the van der Waals radius of deuterium is smaller than that of hydrogen. Under normal circumstances, the CD bond can be shown to be shorter and stronger than the CH bond.

[0172] Therefore, when hydrogen at the substituted position in the above chemical formula 1 is replaced by deuterium, the energy of the ground state decreases, the bond length between deuterium and carbon becomes shorter, and the molecular hardcore volume shrinks. This reduces the electrical polarizability and weakens the intermolecular interaction, thereby increasing the film volume.

[0173] In addition, this property can create a reduced crystallinity of the thin film, i.e., an amorphous state, which can effectively improve the lifetime and driving characteristics of organic light-emitting devices, and the heat resistance can be further improved compared with existing organic light-emitting devices.

[0174] In one embodiment of this specification, the above chemical formula 1 is represented by any one of the following compounds.

[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]

[0207]

[0208]

[0209]

[0210]

[0211] The following is a detailed explanation of chemical formula 2.

[0212] [Chemical Formula 2]

[0213]

[0214] In the above chemical formula 2,

[0215] Ar3 is a substituted or unsubstituted heteroaryl group.

[0216] Ar4 is a substituted or unsubstituted polycyclic aryl group.

[0217] L4 and L5 may be the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted divalent aryl group.

[0218] R4 is either hydrogen or deuterium.

[0219] d and e are integers from 0 to 3. When d is 2 or higher, two or more L4s are either the same or different. When e is 2 or higher, two or more L5s are either the same or different.

[0220] r is an integer from 0 to 3. When r is 2 or more, two or more R4s are the same or different from each other.

[0221] In one embodiment of this specification, Ar3 can be a heteroaryl group with 2 to 60 substituted or unsubstituted carbon atoms.

[0222] In one embodiment of this specification, Ar3 can be a heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms.

[0223] In one embodiment of this specification, Ar3 can be a heteroaryl group with 2 to 20 substituted or unsubstituted carbon atoms.

[0224] In one embodiment of this specification, Ar3 may be a substituted or unsubstituted triazine group.

[0225] In one embodiment of this specification, Ar4 can be a polycyclic aryl group with 2 to 60 carbon atoms, either substituted or unsubstituted.

[0226] In one embodiment of this specification, Ar4 can be a polycyclic aryl group with 2 to 30 substituted or unsubstituted carbon atoms.

[0227] In one embodiment of this specification, Ar4 can be a polycyclic aryl group with 2 to 20 substituted or unsubstituted carbon atoms.

[0228] In one embodiment of this specification, Ar4 may be substituted or unsubstituted fluoranthyl, substituted or unsubstituted phenanthryl, or substituted or unsubstituted triphenylene.

[0229] In one embodiment of this specification, Ar4 may be a deuterated or unsubstituted fluoranthyl, a deuterated or unsubstituted phenanthryl, or a deuterated or unsubstituted triphenylene.

[0230] In one embodiment of this specification, L4 and L5 may be the same as or different from each other, and each may independently be a divalent aryl group with 6 to 60 carbon atoms that is directly bonded, substituted, or unsubstituted.

[0231] In one embodiment of this specification, L4 and L5 may be the same as or different from each other, and each may independently be a divalent aryl group with 6 to 30 carbon atoms that is directly bonded, substituted, or unsubstituted.

[0232] In one embodiment of this specification, L4 and L5 may be the same as or different from each other, and each may independently be a divalent aryl group with 6 to 20 carbon atoms that is directly bonded, substituted, or unsubstituted.

[0233] In one embodiment of this specification, L4 and L5 may be the same as or different from each other, and each may independently be a directly bonded, substituted or unsubstituted divalent phenyl, or a substituted or unsubstituted divalent biphenyl.

[0234] In one embodiment of this specification, L4 and L5 may be the same as or different from each other, and each may independently be a directly bonded, divalent phenyl substituted or unsubstituted with deuterium or aryl groups having 6 to 12 carbon atoms, or a divalent biphenyl substituted or unsubstituted with deuterium.

[0235] In one embodiment of this specification, L5 can be a substituted or unsubstituted divalent aryl group. Compounds of Formula 2 with L5 being a divalent aryl group exhibit excellent electron mobility and, compared to the case where L5 is directly bonded, show advantages such as low voltage, high efficiency, and / or long lifetime in organic light-emitting devices.

[0236] In one embodiment of this specification, L5 can be a divalent aryl group with 6 to 60 carbon atoms, either substituted or unsubstituted.

[0237] In one embodiment of this specification, L5 may be a divalent aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0238] In one embodiment of this specification, L5 can be a divalent aryl group with 6 to 20 carbon atoms, either substituted or unsubstituted.

[0239] In one embodiment of this specification, L5 may be a substituted or unsubstituted divalent phenyl, or a substituted or unsubstituted divalent biphenyl.

[0240] In one embodiment of this specification, L5 may be a divalent phenyl substituted or unsubstituted with deuterium or an aryl group having 6 to 12 carbon atoms, or a divalent biphenyl substituted or unsubstituted with deuterium.

[0241] In one embodiment of this specification, R4 may be hydrogen.

[0242] In one embodiment of this specification, R4 can be deuterium.

[0243] In one embodiment of this specification, d is an integer from 0 to 3. When d is 2 or more, two or more L4s are the same or different from each other.

[0244] In one embodiment of this specification, d is an integer from 0 to 3.

[0245] In one embodiment of this specification, d is 3.

[0246] In one embodiment of this specification, d is 2.

[0247] In one embodiment of this specification, d is 1.

[0248] In one embodiment of this specification, d is 0.

[0249] In one embodiment of this specification, e is an integer from 0 to 3. When e is 2 or more, two or more L5s are the same or different from each other.

[0250] In one embodiment of this specification, e is an integer from 0 to 3.

[0251] In one embodiment of this specification, e is 3.

[0252] In one embodiment of this specification, e is 2.

[0253] In one embodiment of this specification, e is 1.

[0254] In one embodiment of this specification, e is 0.

[0255] In one embodiment of this specification, r is an integer from 0 to 3. When r is 2 or more, two or more R4s are the same or different from each other.

[0256] In one embodiment of this specification, r is an integer from 0 to 3.

[0257] In one embodiment of this specification, r is 3.

[0258] In one embodiment of this specification, r is 2.

[0259] In one embodiment of this specification, r is 1.

[0260] In one embodiment of this specification, r is 0.

[0261] In one embodiment of this specification, the above-mentioned chemical formula 2 can be represented by the following chemical formula 2-1.

[0262] [Chemical Formula 2-1]

[0263]

[0264] Ar4, L4, L5, R4, d, e, and r are the same as those defined in chemical formula 2.

[0265] L6 and L7 may be the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted divalent aryl group.

[0266] R5 and R6 may be the same as or different from each other, and each may be an independently substituted or unsubstituted aryl group.

[0267] f and g are integers from 0 to 3. When f is 2 or more, two or more L6s are the same or different from each other. When g is 2 or more, two or more L7s are the same or different from each other.

[0268] In one embodiment of this specification, L6 and L7 may be the same as or different from each other, and each may independently be a divalent aryl group with 6 to 60 carbon atoms that is directly bonded, substituted, or unsubstituted.

[0269] In one embodiment of this specification, L6 and L7 may be the same as or different from each other, and each may independently be a divalent aryl group with 6 to 30 carbon atoms that is directly bonded, substituted, or unsubstituted.

[0270] In one embodiment of this specification, L6 and L7 may be the same as or different from each other, and each may independently be a divalent aryl group with 6 to 20 carbon atoms that is directly bonded, substituted, or unsubstituted.

[0271] In one embodiment of this specification, L6 and L7 may be the same as or different from each other, and each may independently be a directly bonded, substituted or unsubstituted divalent phenyl.

[0272] In one embodiment of this specification, L6 and L7 may be the same as or different from each other, and each may independently be a divalent phenyl that is directly bonded, substituted with deuterium or cyano, or unsubstituted.

[0273] In one embodiment of this specification, R5 and R6 may be the same as or different from each other, and each may independently be an aryl group with 6 to 60 carbon atoms, either substituted or unsubstituted.

[0274] In one embodiment of this specification, R5 and R6 may be the same as or different from each other, and each may independently be an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0275] In one embodiment of this specification, R5 and R6 may be the same as or different from each other, and each may independently be an aryl group with 6 to 20 carbon atoms, either substituted or unsubstituted.

[0276] In one embodiment of this specification, R5 and R6 may be the same as or different from each other, and each may independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluoranthyl, or a substituted or unsubstituted phenanthryl.

[0277] In one embodiment of this specification, R5 and R6 may be the same as or different from each other, and each may independently be a phenyl substituted or unsubstituted with deuterium, cyano, alkyl with 1 to 10 carbon atoms or aryl with 6 to 20 carbon atoms; a biphenyl substituted or unsubstituted with deuterium or cyano; a naphthyl substituted or unsubstituted with deuterium; a fluoranthyl substituted or unsubstituted with deuterium; or a phenanthryl substituted or unsubstituted with deuterium.

[0278] In one embodiment of this specification, f is an integer from 0 to 3. When f is 2 or more, two or more L6s are the same or different from each other.

[0279] In one embodiment of this specification, f is an integer from 0 to 3.

[0280] In one embodiment of this specification, f is 3.

[0281] In one embodiment of this specification, f is 2.

[0282] In one embodiment of this specification, f is 1.

[0283] In one embodiment of this specification, f is 0.

[0284] In one embodiment of this specification, g is an integer from 0 to 3. When g is 2 or more, two or more L7s are the same or different from each other.

[0285] In one embodiment of this specification, g is an integer from 0 to 3.

[0286] In one embodiment of this specification, g is 3.

[0287] In one embodiment of this specification, g is 2.

[0288] In one embodiment of this specification, g is 1.

[0289] In one embodiment of this specification, g is 0.

[0290] In one embodiment of this specification, the compound represented by the above chemical formula 2 contains at least one deuterium.

[0291] In one embodiment of this specification, the compound represented by Chemical Formula 2 is substituted with at least 40% deuterium. In another embodiment, the compound represented by Chemical Formula 2 is substituted with more than 50% deuterium. In another embodiment, the compound represented by Chemical Formula 2 is substituted with more than 60% deuterium. In another embodiment, the compound represented by Chemical Formula 2 is substituted with more than 70% deuterium. In another embodiment, the compound represented by Chemical Formula 2 is substituted with more than 80% deuterium. In another embodiment, the compound represented by Chemical Formula 2 is substituted with more than 90% deuterium. In yet another embodiment, the compound represented by Chemical Formula 2 is substituted with 100% deuterium.

[0292] In one embodiment of this specification, the compound represented by Chemical Formula 2 contains 40% to 60% deuterium. In another embodiment, the compound represented by Chemical Formula 2 contains 40% to 80% deuterium. In another embodiment, the compound represented by Chemical Formula 2 contains 60% to 80% deuterium. In yet another embodiment, the compound represented by Chemical Formula 2 contains 80% to 100% deuterium.

[0293] Specifically, the physicochemical properties of deuterium, such as bond length, are different from those of hydrogen. Compared with the CH bond, the CD bond has a smaller stretching amplitude, so the van der Waals radius of deuterium is smaller than that of hydrogen. Under normal circumstances, the CD bond can be shown to be shorter and stronger than the CH bond.

[0294] Therefore, when hydrogen at the substituted position in the above chemical formula 2 is replaced by deuterium, the energy of the ground state decreases, the bond length between deuterium and carbon becomes shorter, and the molecular hardcore volume shrinks. This reduces the electrical polarizability and weakens the intermolecular interaction, thereby increasing the film volume.

[0295] In addition, this property can create a reduced crystallinity of the thin film, i.e., an amorphous state, which can effectively improve the lifetime and driving characteristics of organic light-emitting devices, and the heat resistance can be further improved compared with existing organic light-emitting devices.

[0296] In one embodiment of this specification, the above chemical formula 2 is represented by any one of the following compounds.

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347] The compounds represented by chemical formulas 1 and 2 according to one embodiment of this specification can be manufactured with a core structure as described in the manufacturing examples below. Substituents can be combined by methods known in the art, and the type, position, or number of substituents can be varied according to techniques known in the art.

[0348] In this specification, compounds with various band gaps can be synthesized by introducing various substituents into the core structures of the compounds represented by the above-described chemical formulas 1 and 2. Furthermore, in this specification, the HOMO and LUMO energy levels of the compounds can also be tuned by introducing various substituents into the core structures described above.

[0349] The following section explains organic light-emitting devices.

[0350] In this specification, the term "layer" is used interchangeably with "film" primarily used in this technical field, referring to a coating covering a target area. The size of the aforementioned "layer" is not limited; the sizes of each "layer" can be the same or different. According to one embodiment, the size of a "layer" can be equal to the size of the entire device, equivalent to the size of a specific functional area, or as small as a single sub-pixel.

[0351] In this specification, the meaning of a specific substance A being contained in layer B includes i) the case where one or more substances A are contained in a single layer of layer B, and ii) the case where layer B consists of one or more layers and substances A are contained in one or more layers of multiple layers of layer B.

[0352] In this specification, the meaning of a specific substance A being contained in layer C or layer D is all of the following: i) contained in one or more layers of layer C, or ii) contained in one or more layers of layer D, or iii) contained in one or more layers of layer C and one or more layers of layer D respectively.

[0353] An organic light-emitting device according to an embodiment of this specification is characterized in that it comprises: an anode, a cathode, and a first organic layer and a second organic layer disposed 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.

[0354] An organic light-emitting device according to one embodiment of this specification forms an organic layer using a compound represented by chemical formula 1 and a compound represented by chemical formula 2. Alternatively, it can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0355] The aforementioned compounds can be used to form organic layers not only through vacuum evaporation but also through solution coating in the fabrication of organic light-emitting devices. Here, solution coating refers to methods such as spin coating, dip coating, inkjet printing, screen printing, spray coating, and roll coating, but is not limited to these.

[0356] The organic layer of the organic light-emitting device according to one embodiment of this specification can be formed as a single-layer structure or as a multilayer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of this specification may have a structure including one or more of the following as organic layers: a hole injection layer, a hole transport layer, a hole injection and transport layer, a hole transport auxiliary 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. However, the structure of the organic light-emitting device is not limited to this, and may include fewer or more organic layers.

[0357] In one embodiment of this specification, the first organic layer may include a hole injection layer, a hole transport layer, a hole injection and transport layer, or a hole transport auxiliary layer. In one embodiment of this specification, the first organic layer includes a hole transport auxiliary layer, which may contain a compound represented by the above-described chemical formula 1.

[0358] In one embodiment of this specification, the second organic layer may include an electron transport layer, an electron injection layer, or an electron transport and injection layer. In one embodiment of this specification, the second organic layer includes an electron transport and injection layer, which may contain a compound represented by the above-described chemical formula 2.

[0359] In one embodiment of this specification, the second organic layer may further comprise a metal coordination compound.

[0360] In one embodiment of this specification, the second organic layer may further comprise a lithium metal coordination compound.

[0361] In one embodiment of this specification, the second organic layer may further comprise lithium 8-hydroxyquinoline (LiQ).

[0362] In one embodiment of this specification, the second organic layer comprises a compound represented by the above chemical formula 2, and may also comprise a metal coordination compound, wherein the weight ratio of the compound represented by the above chemical formula 2 to the metal coordination compound may be 1:9 to 9:1.

[0363] In one embodiment of this specification, the second organic layer comprises a compound represented by the above chemical formula 2, and may also comprise a metal coordination compound. The weight ratio of the compound represented by the above chemical formula 2 to the metal coordination compound may be 2:8 to 8:2, 3:7 to 7:3, or 4:6 to 6:4.

[0364] In one embodiment of this specification, the second organic layer comprises a compound represented by the above-mentioned chemical formula 2, and may also comprise a metal coordination compound, wherein the weight ratio of the compound represented by the above-mentioned chemical formula 2 to the above-mentioned metal coordination compound may be 5:5.

[0365] In an organic light-emitting device according to one embodiment of this specification, one or more organic layers may be further provided between the anode and the cathode. The organic layer may also include one or more of the following: a hole injection layer, a hole transport layer, a hole injection and transport layer, a hole transport auxiliary 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.

[0366] In one embodiment of this specification, when the organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

[0367] In an organic light-emitting device according to one embodiment of this specification, one or more organic layers may be further provided between the anode and the cathode, and the further provided organic layer may be a light-emitting layer.

[0368] In one embodiment of this specification, the first organic layer may be disposed between the anode and the light-emitting layer.

[0369] In one embodiment of this specification, the first organic layer may be disposed in contact with the light-emitting layer.

[0370] In one embodiment of this specification, the second organic layer may be disposed between the light-emitting layer and the cathode.

[0371] In one embodiment of this specification, a hole suppression layer may be provided between the second organic layer and the light-emitting layer.

[0372] In one embodiment of this specification, the light-emitting layer may contain a compound represented by the following chemical formula 3.

[0373] [Chemical Formula 3]

[0374]

[0375] In the above chemical formula 3

[0376] L20 and L21 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0377] Ar20 and Ar21 may be the same as or different from each other, and each can be independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0378] R201 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0379] r201 is an integer from 1 to 8. When r201 is 2 or more, two or more r201s are the same or different from each other.

[0380] In one embodiment of this specification, L20 and L21 may be the same as or different from each other, and each is independently a directly bonded monocyclic or polycyclic arylene group with 6 to 30 carbon atoms, or a divalent heterocyclic group with 2 to 30 carbon atoms.

[0381] In one embodiment of this specification, L20 and L21 may be the same as or different from each other, and each independently is a directly bonded, deuterated or unsubstituted phenylene, deuterated or unsubstituted biphenylene, deuterated or unsubstituted naphthylene, divalent dibenzofuranyl, or divalent dibenzothiopheneyl.

[0382] In one embodiment of this specification, L20 and L21 are directly bonded.

[0383] In one embodiment of this specification, the Ar20 and Ar21 described above may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms that has been substituted or unsubstituted, or a monocyclic or polycyclic heterocyclic group with 2 to 30 carbon atoms that has been substituted or unsubstituted.

[0384] In one embodiment of this specification, the Ar20 and Ar21 described above may be the same as or different from each other, and each is independently a monocyclic to tetracyclic aryl group with 6 to 20 carbon atoms, substituted or unsubstituted, or a monocyclic to tetracyclic heterocyclic group with 6 to 20 carbon atoms.

[0385] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, a biphenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, a naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. Thiophene group substituted or unsubstituted, dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0386] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each is independently a deuterated or unsubstituted naphthyl group.

[0387] According to one embodiment of this specification, R201 is hydrogen.

[0388] According to one embodiment of this specification, the above-mentioned chemical formula 3 can be represented by the following compounds, but is not limited thereto.

[0389]

[0390] In one embodiment of this specification, the organic light-emitting device includes: an anode, a cathode, a first organic layer and a second organic layer with two or more layers disposed between the anode and the cathode, wherein the first organic layer with two or more layers contains a compound represented by the above chemical formula 1, and the second organic layer with two or more layers may contain a compound represented by the above chemical formula 2.

[0391] In an organic light-emitting device according to one embodiment of this specification, the first organic layer includes two or more hole transport auxiliary layers, and at least one of the two or more hole transport auxiliary layers may contain a compound represented by the above-described chemical formula 1. Furthermore, the two or more hole transport auxiliary layers may be formed from the same substance or different substances.

[0392] In an organic light-emitting device according to one embodiment of this 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 contain a compound represented by the above-described chemical formula 2. Furthermore, the two or more electron transport and injection layers may be formed from the same substance or different substances.

[0393] In one embodiment of this specification, the thicknesses of the first organic layer comprising the compound represented by Chemical Formula 1 and the second organic layer comprising the compound represented by Chemical Formula 2 are each [missing information]. to Preferred to More preferably to

[0394] In one embodiment of this specification, the first organic layer and the second organic layer may contain other organic compounds, metals, or metal compounds in addition to the compounds represented by chemical formula 1 and chemical formula 2.

[0395] In another embodiment, the first organic layer and the second organic layer do not contain any other organic compounds, metals or metal compounds other than the compounds represented by the above-described chemical formula 1 and the compounds represented by the above-described chemical formula 2.

[0396] In one embodiment of this specification, the first organic layer and the second organic layer may be disposed in contact with each other.

[0397] In one embodiment of this specification, the first organic layer and the second organic layer may be disposed without being in contact with each other.

[0398] In one embodiment of this specification, one or more organic layers are located between the first organic layer and the second organic layer.

[0399] In one embodiment of this specification, the light-emitting layer is located between the first organic layer and the second organic layer.

[0400] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with an anode, one or more organic layers and a cathode sequentially stacked on a substrate (normal type).

[0401] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with a reverse structure (inverted type) in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate.

[0402] For example, the organic light-emitting device described above can have a stacked structure as shown below, but is not limited to this.

[0403] (1) Anode / hole transport layer / light-emitting layer / cathode

[0404] (2) Anode / hole injection layer / hole transport layer / light emission layer / cathode

[0405] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0406] (4) Anode / Hole transport layer / Light emission layer / Electron transport layer / Cathode

[0407] (5) Anode / Hole transport layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0408] (6) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0409] (7) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0410] (8) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0411] (9) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0412] (10) Anode / Hole transport layer / Hole modulation layer / Light emission layer / Electron transport layer / Cathode

[0413] (11) Anode / Hole transport layer / Hole modulation layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0414] (12) Anode / Hole injection layer / Hole transport layer / Hole modulation layer / Light emission layer / Electron transport layer / Cathode

[0415] (13) Anode / Hole Injection Layer / Hole Transport Layer / Hole Modulation Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0416] (14) Anode / Hole transport layer / Light emission layer / Electron modulation layer / Electron transport layer / Cathode

[0417] (15) Anode / Hole transport layer / Light emission layer / Electron modulation layer / Electron transport layer / Electron injection layer / Cathode

[0418] (16) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Modulation Layer / Electron Transport Layer / Cathode

[0419] (17) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Modulation Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0420] (18) Anode / Hole Injection Layer / Hole Transport Layer / Hole Modulation Layer / Light Emitting Layer / Electron Modulation Layer / Electron Transport and Injection Layer / Cathode

[0421] (19) Anode / Hole injection layer / Hole transport layer / Hole conditioning layer / Light emission layer / Electron conditioning layer / Electron transport and injection layer / Cathode / Capping layer

[0422] (20) Anode / Hole injection layer / Hole transport layer / Hole transport auxiliary layer / Light emission layer / Hole suppression layer / Electron transport and injection layer / Cathode

[0423] (21) Anode / hole injection layer / hole transport layer / hole transport auxiliary layer / light emission layer / hole suppression layer / electron transport and injection layer / cathode / capping layer

[0424] The organic light-emitting device structure described in this specification can have the following characteristics: Figures 1 to 2 The structure shown is not limited to this.

[0425] Figure 1 The diagram 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 the structure described above, the compound represented by Chemical Formula 1 may be included in the first organic layer 21, and the compound represented by Chemical Formula 2 may be included in the second organic layer 22.

[0426] Figure 2 The diagram illustrates the structure of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a hole transport auxiliary layer 5, a light-emitting layer 6, a hole suppression layer 7, an electron transport and injection layer 8, and a cathode 9. In the structure described above, the compound represented by Chemical Formula 1 may be included in the hole transport layer 4 or the hole transport auxiliary layer 5, and the compound represented by Chemical Formula 2 may be included in the electron transport and injection layer 8.

[0427] According to one embodiment of this specification, the organic light-emitting device can be a series structure of two or more independent devices connected in series. In one embodiment, the series structure can be a shape in which each organic light-emitting device is bonded by a charge-generating layer. Compared to single-unit devices, devices with a series structure can be driven at a lower current, thus offering the advantage of significantly improved device lifetime characteristics, while maintaining the same brightness.

[0428] For example, an organic light-emitting device according to one embodiment of this specification can be manufactured as follows: An anode is formed by depositing a metal or a conductive metal oxide or alloy thereof onto a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation. Then, an organic layer comprising one or more layers selected from a hole injection layer, a hole transport layer, a hole transport and injection layer, a hole transport auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, and an electron transport and injection layer is formed on the anode. Finally, a material suitable for use as a cathode is deposited onto the organic layer. Alternatively, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto a substrate.

[0429] The aforementioned organic layer can be a multilayer structure including a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light-emitting layer, and an electron transport and injection layer, but is not limited to this; it can also be a single-layer structure. Furthermore, the aforementioned organic layer can be manufactured in smaller quantities using various polymer materials and solvent processes other than vapor deposition, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer.

[0430] The anode described above is the electrode for injecting holes. As the anode material, it is generally preferred to be a material with a high work function in order to enable holes to be smoothly injected into the organic layer. Specific examples of anode materials that can be used in this invention include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; 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-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0431] The cathode described above is the electrode into which electrons are injected. As a cathode material, it is generally preferred to be a material with a low work function in order to facilitate the injection of electrons into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer structures such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0432] The aforementioned hole injection layer facilitates the injection of holes from the anode to the light-emitting layer. The hole injection material is one that can effectively receive holes from the anode at low voltages. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile hexaazabenzophenanthrene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and conductive polymers based on polyaniline and polythiophene. The thickness of the hole injection layer can range from 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, it has the advantage of preventing a decrease in hole injection characteristics; when it is less than 150 nm, it has the advantage of preventing an increase in driving voltage to improve hole migration when the hole injection layer is too thick.

[0433] In one embodiment of this specification, the hole injection layer may contain a compound represented by the chemical formula HI-1, but is not limited thereto.

[0434] [Chemical formula HI-1]

[0435]

[0436] In the above chemical formula HI-1,

[0437] At least one of X'1 to X'6 is N, and the rest are CH.

[0438] R309 to R314 may be the same as or different from each other, and each is independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or combined with adjacent groups to form substituted or unsubstituted rings.

[0439] In one embodiment of this specification, X'1 to X'6 are N.

[0440] In one embodiment of this specification, R309 to R314 are cyano groups.

[0441] In one embodiment of this specification, the above-mentioned chemical formula HI-1 may be represented by the following compounds, but is not limited thereto.

[0442]

[0443] The aforementioned hole transport layer facilitates hole transport. The hole transport material is capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer; materials with high hole mobility are suitable. Specific examples include aryl amine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but these are not limited to these.

[0444] In one embodiment of this specification, the hole transport layer may contain a compound represented by the following chemical formula HT-1, but is not limited thereto.

[0445] [Chemical formula HT-1]

[0446]

[0447] In the above chemical formula HT-1,

[0448] R403 to R406 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amino, substituted or unsubstituted heteroaryl, and combinations thereof, or may be combined with adjacent groups to form substituted or unsubstituted rings.

[0449] L401 to L403 may be the same as or different from each other, and each is independently a substituted or unsubstituted arylene or a substituted or unsubstituted heteroarylene.

[0450] l401 to l403 may be the same or different from each other, and each is an independent integer from 1 to 3. When l401 to l403 is 2 or more, l401 to l403 may be the same or different from each other.

[0451] In one embodiment of this specification, R403 to R406 may be the same as or different from each other, and each independently is selected from any one of substituted or unsubstituted aryl, substituted or unsubstituted amino, substituted or unsubstituted heteroaryl, and combinations thereof.

[0452] In one embodiment of this specification, R403 to R406 may be the same as or different from each other, and each is independently an aryl group having 6 to 30 carbon atoms.

[0453] In one embodiment of this specification, R403 to R406 may be the same as or different from each other, and each is independently phenyl, biphenyl or naphthyl.

[0454] In one embodiment of this specification, R403 to R406 may be the same as or different from each other, and each is independently a phenyl group.

[0455] In one embodiment of this specification, L401 to L403 may be the same as or different from each other, and each is independently an arylene with 6 to 30 carbon atoms, or a heteroarylene with 3 to 30 carbon atoms substituted by an arylene.

[0456] In one embodiment of this specification, L401 to L403 may be the same as or different from each other, and each is independently a phenylene, a divalent biphenyl, or a divalent carbazolyl group substituted with or unsubstituted with an aryl group.

[0457] In one embodiment of this specification, L401 and L403 are phenylene oxides.

[0458] In one embodiment of this specification, L402 is a divalent carbazole group substituted with a naphthyl group.

[0459] In one embodiment of this specification, the above chemical formula HT-1 may be represented by the following compounds, but is not limited thereto.

[0460]

[0461] The aforementioned hole regulation layer is a layer that improves device lifetime and efficiency by regulating 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 into the hole injection layer. It can 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 simultaneously performs hole injection and hole transport, and can be made of any known materials without restriction.

[0462] A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, which may contain materials known in the art for hole injection or transport.

[0463] An electron suppression layer can be disposed between the hole transport layer and the light-emitting layer. This electron suppression layer can be a spirocyclic compound or a material known in this art.

[0464] The aforementioned luminescent layer can emit red, green, or blue light and can be formed from phosphorescent or fluorescent substances. The luminescent substance is capable of receiving holes and electrons from the hole transport layer and electron transport layer respectively, and combining them to emit light in the visible light region; preferably, it is a substance with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complexes (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Compounds of the azole, benzothiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV) polymers; spirocyclic compounds; polyfluorene, fluorene, etc., but not limited to these.

[0465] The main materials for the luminescent layer include aromatic fused-ring derivatives or heterocyclic compounds. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds. Pyrimidine derivatives, etc., but not limited to these.

[0466] When the luminescent layer emits red light, phosphorescent dopants such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum) can be used; or fluorescent substances such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used, but are not limited to these. When the luminescent layer emits green light, phosphorescent materials such as Ir(ppy)3 (facilitated by tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3 (tris(8-hydroxyquinoline)aluminum) can be used as luminescent dopants, but are not limited to these. When the luminescent layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic can be used as luminescent dopants; or fluorescent materials such as spiro-DPVBi, spiro-6P, stilbene (DSB), stilbene aryl (DSA), PFO-based polymers, PPV-based polymers, etc., can be used, but are not limited to these.

[0467] In one embodiment of this specification, the light-emitting dopant may comprise a compound represented by the following chemical formula [D-1], but is not limited thereto.

[0468] [Chemical Formula D-1]

[0469]

[0470] In the above chemical formula D-1,

[0471] T1 to T6 may be the same as or different from each other, and each is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0472] t5 and t6 are each integers from 1 to 4.

[0473] When t5 is 2 or more, the two or more T5 values ​​are either the same or different from each other.

[0474] When t6 is 2 or more, the two or more T6 are the same or different from each other.

[0475] According to one embodiment of this specification, T1 to T6 may be the same as or different from each other, and each is independently hydrogen, a straight-chain or branched alkyl group with 1 to 30 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms.

[0476] According to one embodiment of this specification, T1 to T6 may be the same as or different from each other, and each is independently hydrogen; a straight-chain or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with a cyano group or a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0477] According to one embodiment of this specification, T1 to T6 may be the same as or different from each other, and each is independently phenyl or dibenzofuranyl.

[0478] According to one embodiment of this specification, the above chemical formula D-1 can be represented by the following compounds, but is not limited thereto.

[0479]

[0480] A hole suppression layer can be placed between the electron transport layer and the light-emitting layer. This hole suppression layer prevents holes from reaching the cathode and can typically be formed under the same conditions as the electron injection layer. Specifically... Diazole or triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc., but not limited to these.

[0481] In one embodiment of this specification, the hole suppression layer may contain a compound represented by the following chemical formula HB-1, but is not limited thereto.

[0482] [Chemical formula HB-1]

[0483]

[0484] In the above chemical formula HB-1,

[0485] At least one of Z1 to Z3 is N, and the rest are CH.

[0486] L601 and L602 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.

[0487] Ar601 to Ar603 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0488] In one embodiment of this specification, L601 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0489] In one embodiment of this specification, L601 and L602 may be the same as or different from each other, and each is independently phenylene, biphenylene or naphthylene.

[0490] In one embodiment of this specification, Ar601 to Ar603 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or a heteroaryl group with 3 to 30 carbon atoms, either substituted or unsubstituted.

[0491] In one embodiment of this specification, Ar601 to Ar603 are phenyl or triphenylene.

[0492] In one embodiment of this specification, the above-mentioned chemical formula HB-1 may be represented by the following compounds, but is not limited thereto.

[0493]

[0494] The aforementioned electron transport layer receives electrons from the electron injection layer and transports them to the light-emitting layer, thus facilitating electron transport. The electron transport material is one that can effectively receive electrons from the cathode and transfer them to the light-emitting layer; materials with high electron mobility are suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, and hydroxyflavonoid-metal complexes, but these are not limited to these. The thickness of the electron transport layer can range from 1 to 50 nm. When the thickness of the electron transport layer is greater than 1 nm, it has the advantage of preventing a decrease in electron transport properties; when it is less than 50 nm, it has the advantage of preventing an increase in driving voltage to improve electron migration when the electron transport layer is too thick.

[0495] The aforementioned electron injection layer facilitates electron injection. Preferred electron injection materials include compounds that possess electron transport capabilities, effectively inject electrons from the cathode, exhibit excellent electron injection performance for the luminescent layer or luminescent material, prevent excitons generated in the luminescent layer from migrating to the hole injection layer, and demonstrate excellent thin-film formation ability. Specifically, these include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0496] As the aforementioned electron-injecting material, it may contain at least one of magnesium and lithium fluoride (LiF), specifically, it may contain both magnesium and lithium fluoride (LiF), but is not limited thereto.

[0497] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium, but are not limited to these.

[0498] The electron transport and injection layer described above is a layer that transports electrons to the light-emitting layer. The materials exemplified in the electron transport and electron injection layers described above can be used, but are not limited to these.

[0499] In one embodiment of this specification, the electron transport and injection layer may further comprise a metal coordination compound. The metal coordination compound is as described above.

[0500] In one embodiment of this specification, a capping layer (CPL) may be stacked around the cathode. The capping layer can maximize the light extraction effect or prevent the organic light-emitting device from deteriorating, and may contain capping layer materials known in the art.

[0501] Depending on the materials used, an organic light-emitting device according to one embodiment of this specification can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0502] The organic light-emitting device according to this specification can be included in and used in various electronic devices. For example, the aforementioned electronic devices can be display panels, touch panels, solar modules, lighting devices, etc., and are not limited thereto.

[0503] The following detailed description, using embodiments, aims to provide a more specific explanation of this specification. However, the embodiments described herein can be modified in various ways and are not intended to limit the scope of this application to the embodiments detailed below. These embodiments are provided to provide a more complete explanation of this specification to those skilled in the art.

[0504] <Synthesis example>

[0505] Synthesis Example 1. Synthesis of Compound A-1

[0506]

[0507] Toluene (150 ml) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-([1,1'-biphenyl]-4-yl)-[1,1':4',1”-triphenyl]-4-amine (28.08 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol). The mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to obtain compound A-1 (36.0 g, 80.00% yield). (MS [M+H]) + =650)

[0508] Synthesis Example A-2. Synthesis of Compound A-2

[0509]

[0510] Toluene (150 ml) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-([1,1'-biphenyl]-2-yl)-[1,1':4',1”-triphenyl]-4-amine (28.08 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol). The mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by toluene and water chromatography. After removing the solvent, the mixture was recrystallized from ethyl acetate to obtain compound A-2 (36.0 g, 80.00% yield). (MS [M+H]) + =650)

[0511] Synthesis Example A-3. Synthesis of Compound A-3

[0512]

[0513] Toluene (150 ml) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-([1,1':4',1”-terphenyl]-4-yl)-[1,1':2',1”-terphenyl]-2-amine (33.46 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol). The mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-3 (40.0 g, 79.56% yield). (MS[M+H)) + =726)

[0514] Synthesis Example A-4. Synthesis of Compound A-4

[0515]

[0516] Toluene (150 ml) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-([1,1':4',1”-terphenyl]-4-yl)-[1,1':2',1”-terphenyl]-4-amine (33.46 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol). The mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-4 (40.0 g, 79.56% yield). (MS [M+H]) + =726)

[0517] Synthesis Example A-5. Synthesis of Compound A-5

[0518]

[0519] Toluene (150 ml) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-(4-(naphthyl-1-yl)phenyl)-[1,1'-biphenyl]-4-amine (26.24 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-5 (34.0 g, 78.70% yield). (MS[M+H)) + =624)

[0520] Synthesis Example A-6. Synthesis of Compound A-6

[0521]

[0522] Toluene (150 ml) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-(4-(naphthyl-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (26.24 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-6 (34.0 g, 78.70% yield). (MS[M+H)) + =624)

[0523] Synthesis Example A-7. Synthesis of Compound A-7

[0524]

[0525] Toluene (150 ml) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-(4-(naphthyl-2-yl)phenyl)-[1,1':2',1”-triphenyl]-2-amine (31.62 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to obtain compound A-7 (38.0 g, 78.39% yield). (MS [M+H]) + =700)

[0526] Synthesis Example A-8. Synthesis of Compound A-8

[0527]

[0528] Toluene (150 ml) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-(4-(naphthyl-2-yl)phenyl)-[1,1':2',1”-triphenyl]-4-amine (31.62 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to obtain compound A-8 (38.0 g, 78.39% yield). (MS [M+H]) + =700)

[0529] Synthesis Example A-9. Synthesis of Compound A-9

[0530]

[0531] Toluene (150 ml) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), bis(4-naphth-1-yl)phenyl)amine (29.78 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-9 (37.0 g, 79.28% yield). (MS [M+H]) + =674)

[0532] Synthesis Example A-10. Synthesis of Compound A-10

[0533]

[0534] Toluene (150 ml) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-(4-(phenanthrene-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (29.78 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-10 (37.0 g, 79.28% yield). (MS[M+H)) + =674)

[0535] Synthesis Example A-11. Synthesis of Compound A-11

[0536]

[0537] Toluene (150 ml) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-([1,1':4',1”-terphenyl]-4-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-amine (30.49 g, 70.64 mmol) and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-11 (37.0 g, 78.11% yield). (MS [M+H]) + =684)

[0538] Synthesis Example A-12. Synthesis of Compound A-12

[0539]

[0540] Toluene (150 ml) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-(4-(tert-butyl)phenyl)-[1,1':4',1”-triphenyl]-4-amine (26.67 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tritert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-12 (34.0 g, 77.94% yield). (MS [M+H]) + =630)

[0541] Synthesis Example A-13. Synthesis of Compound A-13

[0542]

[0543] Toluene (150 mL) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorenyl-2-amine (25.54 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 mL) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-13 (33.0 g, 77.63% yield). (MS[M+H)) + =614)

[0544] Synthesis Example A-14. Synthesis of Compound A-14

[0545]

[0546] Toluene (150 ml) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N,9,9-triphenyl-9H-fluorenyl-2-amine (28.93 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-14 (36.0 g, 78.53% yield). (MS [M+H]) + =662)

[0547] Synthesis Example A-15. Synthesis of Compound A-15

[0548]

[0549] Toluene (150 mL) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furanyl-3-amine (23.69 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 mL) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-15 (32.0 g, 78.61% yield). (MS[M+H)) + =588)

[0550] Synthesis Example A-16. Synthesis of Compound A-16

[0551]

[0552] Toluene (150 ml) was added to a mixture of 9-(4-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), 2'-(9H-carbazol-9-yl)-N-phenyl-[1,1'-biphenyl]-4-amine (29.00 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-16 (36.0 g, 78.42% yield). (MS[M+H)) + =663)

[0553] Synthesis Example A-17. Synthesis of Compound A-17

[0554]

[0555] Toluene (150 ml) was added to a mixture of 9-(3-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-([1,1'-biphenyl]-4-yl)-[1,1':4',1”-triphenyl]-4-amine (28.08 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-17 (36.0 g, 80.00% yield). (MS [M+H]) + =650)

[0556] Synthesis Example A-18. Synthesis of Compound A-18

[0557]

[0558] Toluene (150 mL) was added to a mixture of 9-(3-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-([1,1':4',1”-terphenyl]-4-yl)-[1,1':2',1”-terphenyl]-4-amine (33.46 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 mL) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-18 (40.0 g, 79.56% yield). (MS[M+H)) + =726)

[0559] Synthesis Example A-19. Synthesis of Compound A-19

[0560]

[0561] Toluene (150 ml) was added to a mixture of 9-(3-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), N-([1,1'-biphenyl]-4-yl)-4'-(naphth-1-yl)-[1,1'-biphenyl]-4-amine (31.62 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to obtain compound A-19 (38.0 g, 78.39% yield). (MS[M+H)) + =700)

[0562] Synthesis Example A-20. Synthesis of Compound A-20

[0563]

[0564] Toluene (150 ml) was added to a mixture of 9-(3-chlorophenyl)phenanthrene (20.0 g, 69.26 mmol), bis(4-naphth-1-yl)phenyl)amine (29.78 g, 70.64 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to obtain compound A-20 (37.0 g, 79.28% yield). (MS[M+H)) + =674)

[0565] Synthesis Example A-21. Synthesis of Compound A-21

[0566]

[0567] Toluene (150 ml) was added to 9-(4'-chloro-[1,1'-biphenyl]-4-yl)phenanthrene (20.0 g, 54.81 mmol), di([1,1'-biphenyl]-4-yl)amine (17.97 g, 55.91 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to obtain compound A-21 (28.0 g, 78.61% yield). (MS[M+H)) + =650)

[0568] Synthesis Example A-22. Synthesis of Compound A-22

[0569]

[0570] Toluene (150 ml) was added to 9-(4'-chloro-[1,1'-biphenyl]-4-yl)phenanthrene (20.0 g, 54.81 mmol), N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (17.97 g, 55.91 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to obtain compound A-22 (28.0 g, 78.61% yield). (MS[M+H)) + =650)

[0571] Synthesis Example A-23. Synthesis of Compound A-23

[0572]

[0573] Toluene (150 ml) was added to 9-(5-chloro-[1,1'-biphenyl]-2-yl)phenanthrene (20.0 g, 54.81 mmol), N-([1,1'-biphenyl]-2-yl)-[1,1':4',1”-triphenyl]-4-amine (22.23 g, 55.91 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-23 (31.0 g, 77.91% yield). (MS [M+H]) + =726)

[0574] Synthesis Example A-24. Synthesis of Compound A-24

[0575]

[0576] Toluene (150 ml) was added to 9-(5-chloro-[1,1'-biphenyl]-2-yl)phenanthrene (20.0 g, 54.81 mmol), N-([1,1'-biphenyl]-2-yl)-[1,1':4',1”-triphenyl]-4-amine (17.97 g, 55.91 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tritert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by toluene and water chromatography. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-24 (28.0 g, 78.61% yield). (MS [M+H]) + =650)

[0577] Synthesis Example A-25. Synthesis of Compound A-25

[0578]

[0579] Toluene (150 ml) was added to 9-(6-chloro-[1,1'-biphenyl]-3-yl)phenanthrene (20.0 g, 54.81 mmol), N-([1,1'-biphenyl]-2-yl)-[1,1':4',1”-triphenyl]-4-amine (22.23 g, 55.91 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound A-25 (31.0 g, 77.91% yield). (MS [M+H]) + =726)

[0580] Synthesis Example A-26. Synthesis of Compound A-26

[0581]

[0582] Toluene (150 ml) was added to 9-(6-chloro-[1,1'-biphenyl]-3-yl)phenanthrene (20.0 g, 54.81 mmol), N-([1,1'-biphenyl]-2-yl)-[1,1':4',1”-triphenyl]-4-amine (17.97 g, 55.91 mmol), and sodium tert-butoxide (9.32 g, 96.96 mmol), and the mixture was heated and stirred for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (10 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by toluene and water chromatography. After solvent removal, the mixture was recrystallized from ethyl acetate to give compound A-26 (28.0 g, 78.61% yield). (MS [M+H]) + =650)

[0583] Synthesis Example A-27. Synthesis of Compound A-27

[0584]

[0585] Compound A-1 (20.0 g, 30.78 mmol) obtained in Synthetic Example A-1 was added to benzene-d6 (200 ml) and completely dissolved. Trifluoromethanesulfonic acid (1.4 ml, 15.39 mmol) was then added, and the mixture was stirred for 25 minutes. After the reaction was complete, dichloromethane was added, and the layers were separated to obtain the organic layer. The organic layer was dried over anhydrous magnesium sulfate (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and recrystallized from ethyl acetate to obtain compound A-27 (16.0 g, 78.30%). (MS [M+H]) + =664)

[0586] Synthesis Example A-28. Synthesis of Compound A-28

[0587]

[0588] Compound A-2 (20.0 g, 30.78 mmol) obtained in Synthetic Example A-2 was added to benzene-d6 (200 ml) and completely dissolved. Trifluoromethanesulfonic acid (1.4 ml, 15.39 mmol) was then added, and the mixture was stirred for 25 minutes. After the reaction was complete, dichloromethane was added, and the layers were separated to obtain the organic layer. The organic layer was dried over anhydrous magnesium sulfate (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and recrystallized from ethyl acetate to obtain compound A-28 (16.0 g, 78.30% yield). (MS[M+H)) + =664)

[0589] Synthesis Example A-29. Synthesis of Compound A-29

[0590]

[0591] Compound A-5 (20.0 g, 30.06 mmol) obtained in Synthetic Example A-5 was added to benzene-d6 (200 ml) and completely dissolved. Trifluoromethanesulfonic acid (1.4 ml, 15.39 mmol) was then added, and the mixture was stirred for 25 minutes. After the reaction was complete, dichloromethane was added, and the layers were separated to obtain the organic layer. The organic layer was dried over anhydrous magnesium sulfate (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and recrystallized from ethyl acetate to obtain compound A-29 (16.0 g, 78.24% yield). (MS[M+H)) + =638)

[0592] Synthesis Example A-30. Synthesis of Compound A-30

[0593]

[0594] Compound A-22 (20.0 g, 30.78 mmol) obtained in Synthetic Example A-22 was added to benzene-d6 (200 mL). After complete dissolution, trifluoromethanesulfonic acid (1.4 mL, 15.39 mmol) was added, and the mixture was stirred for 25 minutes. After the reaction was complete, dichloromethane was added, and the layers were separated to obtain the organic layer. The organic layer was dried over anhydrous magnesium sulfate (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and recrystallized from ethyl acetate to obtain compound A-30 (16.0 g, 78.30% yield). (MS[M+H)) + =664)

[0595] Synthesis Example B-1. Synthesis of Compound B-1

[0596]

[0597] 3-Bromo-2-chlorobenzonitrile (6.49 g, 30 mmol) and compound 1-1 (9.84 g, 33 mmol) were added to tetrahydrofuran (THF, 300 mL). 2M aqueous K₂CO₃ solution (200 mL) and tetrakis(triphenylphosphine)palladium(O) (Pd(PPH₃)⁻⁴, 0.3 g) were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 1-2.

[0598] Compounds 1-2 (11.70 g, 30 mmol) and 1-3 (14.96 g, 33 mmol) obtained in this manner were added to tetrahydrofuran (THF, 300 mL). 2M K₂CO₃ aqueous solution (200 mL), palladium(II) acetate (Pd(OAc)₂, 0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to obtain compound B-1 (16.5 g, 72% yield). (MS[M+H)) + =763)

[0599] Synthesis Example B-2. Synthesis of Compound B-2

[0600]

[0601] Compound 2-2 was prepared by replacing compound 1-1 with compound 2-1, and compound 1-3 was prepared by replacing compound 1-3 with compound 2-3. Otherwise, compound B-2 was prepared by the same method as in synthetic example B-1. (MS[M+H)+ =889)

[0602] Synthesis Example B-3. Synthesis of Compound B-3

[0603]

[0604] Compound 3-2 was prepared by replacing compound 1-1 with compound 3-1, and compound 1-2 was prepared by replacing compound 1-2 with compound 3-3. Otherwise, compound B-3 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =788)

[0605] Synthesis Example B-4. Synthesis of Compound B-4

[0606]

[0607] Compound 4-2 was prepared by replacing compound 1-1 with compound 4-1, and compound 1-3 was prepared by replacing compound 1-3 with compound 4-3. Otherwise, compound B-4 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =839)

[0608] Synthesis Example B-5. Synthesis of Compound B-5

[0609]

[0610] Compound 5-2 was prepared by replacing compound 1-1 with compound 5-1, and compound 1-3 was prepared by replacing compound 1-3 with compound 5-3. Otherwise, compound B-5 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =763)

[0611] Synthesis Example B-6. Synthesis of Compound B-6

[0612]

[0613] Compound 6-2 was prepared by replacing compound 1-1 with compound 6-1, and compound 1-3 was prepared by replacing compound 1-3 with compound 6-3. Otherwise, compound B-6 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =889)

[0614] Synthesis Example B-7. Synthesis of Compound B-7

[0615]

[0616] Compound 7-2 was prepared by replacing compound 1-1 with compound 7-1, and compound 1-3 was prepared by replacing compound 1-3 with compound 7-3. Otherwise, compound B-7 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =865)

[0617] Synthesis Example B-8. Synthesis of Compound B-8

[0618]

[0619] Compound 8-2 was prepared by replacing compound 1-1 with compound 8-1, and compound 1-3 was prepared by replacing compound 1-3 with compound 8-3. Otherwise, compound B-8 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =863)

[0620] Synthesis Example B-9. Synthesis of Compound B-9

[0621]

[0622] Compound 9-2 was prepared by replacing compound 1-1 with compound 9-1, and compound 1-3 was prepared by replacing compound 1-3 with compound 9-3. Otherwise, compound B-9 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =839)

[0623] Synthesis Example B-10. Synthesis of Compound B-10

[0624]

[0625] Compound 10-2 was prepared by replacing compound 1-1 with compound 10-1, and compound 10-3 was prepared by replacing compound 1-3 with compound 10-3. Otherwise, compound B-10 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =863)

[0626] Synthesis Example B-11. Synthesis of Compound B-11

[0627]

[0628] Compound 11-2 was prepared by replacing compound 1-1 with compound 11-1, and compound 11-3 was prepared by replacing compound 1-3 with compound 11-3. Otherwise, compound B-11 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =863)

[0629] Synthesis Example B-12. Synthesis of Compound B-12

[0630]

[0631] Compound 12-2 was prepared by replacing compound 1-1 with compound 12-1, and compound 12-3 was prepared by replacing compound 1-3 with compound 12-3. Otherwise, compound B-12 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =791)

[0632] Synthesis Example B-13. Synthesis of Compound B-13

[0633]

[0634] Compound 13-2 was prepared by replacing compound 1-1 with compound 13-1, and compound 13-3 was prepared by replacing compound 1-3 with compound 13-3. Otherwise, compound B-13 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =839)

[0635] Synthesis Example B-14. Synthesis of Compound B-14

[0636]

[0637] Compound 14-2 was prepared by replacing compound 1-1 with compound 14-1, and compound 14-3 was prepared by replacing compound 1-3 with compound 14-3. Otherwise, compound B-14 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =889)

[0638] Synthetic Example B-15. Synthesis of Compound B-15

[0639]

[0640] Compound 15-2 was prepared by replacing compound 1-1 with compound 15-1, and compound 15-3 was prepared by replacing compound 1-3 with compound 15-3. Otherwise, compound B-15 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =839)

[0641] Synthesis Example B-16. Synthesis of Compound B-16

[0642]

[0643] Compound 16-2 was prepared by replacing compound 1-1 with compound 16-1, and compound 16-3 was prepared by replacing compound 1-3 with compound 16-3. Otherwise, compound B-16 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =795)

[0644] Synthesis Example B-17. Synthesis of Compound B-17

[0645]

[0646] Compound 17-2 was prepared by replacing compound 1-1 with compound 17-1, and compound 17-3 was prepared by replacing compound 1-3 with compound 17-3. Otherwise, compound B-17 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =788)

[0647] Synthesis Example B-18. Synthesis of Compound B-18

[0648]

[0649] Compound 18-2 was prepared by replacing compound 1-1 with compound 18-1, and compound 18-3 was prepared by replacing compound 1-3 with compound 18-3. Otherwise, compound B-18 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =840)

[0650] Synthesis Example B-19. Synthesis of Compound B-19

[0651]

[0652] Compound 19-2 was prepared by replacing compound 1-1 with compound 19-1, and compound 19-3 was prepared by replacing compound 1-3 with compound 19-3. Otherwise, compound B-19 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =763)

[0653] Synthesis Example B-20. Synthesis of Compound B-20

[0654]

[0655] Compound 20-2 was prepared by replacing compound 1-1 with compound 20-1, and compound 1-3 was prepared by replacing compound 1-3 with compound 20-3. Otherwise, compound B-20 was prepared by the same method as in synthetic example B-1. (MS[M+H) + =687)

[0656] Synthetic Example B-21: Preparation of Compound B-21

[0657]

[0658] Compound B-7 (60.0 g, 69.36 mmol) obtained in Synthetic Example B-7 and AlCl3 (0.5 g) were added to C6D6 (400 ml) and stirred for 30 minutes. After the reaction was complete, D2O (30 ml) was added, and the mixture was stirred for another 30 minutes. Then, trimethylamine (6 ml) was added dropwise. The reaction mixture was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over anhydrous magnesium sulfate (MgSO4) and recrystallized from ethyl acetate to obtain compound B-21 (31.0 g, 51.37%). (MS [M+H]) + =870)

[0659] Synthesis Example B-22. Synthesis of Compound B-22

[0660]

[0661] Compound B-7 (60.0 g, 69.36 mmol) obtained in Synthetic Example B-7 and AlCl3 (0.5 g) were added to C6D6 (400 ml) and stirred for 30 minutes. After the reaction was complete, D2O (60 ml) was added, and the mixture was stirred for 30 minutes. Then, trimethylamine (6 ml) was added dropwise. The reaction mixture was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over anhydrous magnesium sulfate (MgSO4) and recrystallized from ethyl acetate to obtain compound B-22. (MS[M+H)) + =875)

[0662] Synthesis Example B-23. Synthesis of Compound B-23

[0663]

[0664] Compound B-15 (60.0 g, 71.51 mmol) obtained in Synthetic Example B-15 and AlCl3 (0.5 g) were added to C6D6 (400 ml) and stirred for 30 minutes. After the reaction was complete, D2O (30 ml) was added, and the mixture was stirred for another 30 minutes. Then, trimethylamine (6 ml) was added dropwise. The reaction mixture was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over anhydrous magnesium sulfate (MgSO4) and recrystallized from ethyl acetate to obtain compound B-23. (MS[M+H)) + =844)

[0665] Synthesis Example B-24. Synthesis of Compound B-24

[0666]

[0667] Compound B-15 (60.0 g, 71.51 mmol) obtained in Synthetic Example B-15 and AlCl3 (0.5 g) were added to C6D6 (400 ml) and stirred for 30 minutes. After the reaction was complete, D2O (60 ml) was added, and the mixture was stirred for 30 minutes. Then, trimethylamine (6 ml) was added dropwise. The reaction mixture was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over anhydrous magnesium sulfate (MgSO4) and recrystallized from ethyl acetate to obtain compound B-24. (MS[M+H)) + =849)

[0668] Synthesis Example B-25. Synthesis of Compound B-25

[0669]

[0670] Compound B-20 (60.0 g, 87.36 mmol) obtained in Synthetic Example B-20 and AlCl3 (0.5 g) were added to C6D6 (400 ml) and stirred for 30 minutes. After the reaction was complete, D2O (30 ml) was added, and the mixture was stirred for another 30 minutes. Then, trimethylamine (6 ml) was added dropwise. The reaction mixture was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over anhydrous magnesium sulfate (MgSO4) and recrystallized from ethyl acetate to obtain compound B-25. (MS[M+H)) + =692)

[0671] Synthesis Example B-26. Synthesis of Compound B-26

[0672]

[0673] Compound B-20 (60.0 g, 87.36 mmol) obtained in Synthetic Example B-20 and AlCl3 (0.5 g) were added to C6D6 (400 ml) and stirred for 30 minutes. After the reaction was complete, D2O (60 ml) was added, and the mixture was stirred for 30 minutes. Then, trimethylamine (6 ml) was added dropwise. The reaction mixture was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over anhydrous magnesium sulfate (MgSO4) and recrystallized from ethyl acetate to obtain compound B-26. (MS[M+H)) + =697)

[0674] <Experimental Examples and Comparative Experimental Examples>

[0675] Experimental Example 1

[0676] ITO (Indium Tin Oxide) A glass substrate coated with a thin film of ITO was immersed in distilled water containing detergent and washed using ultrasound. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for 10 minutes of ultrasonic washing. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0677] On the ITO transparent electrode prepared in this way, a compound represented by the following chemical formula HI1 will be applied... A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. On the aforementioned hole injection layer, a compound represented by the chemical formula HT1 is used as a hole transport layer. After vacuum evaporation to a thickness of [amount], compound A-1 manufactured in the above synthesis example A-1 will be used as [amount]. A hole transport assist layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. Next, as the light-emitting layer, a compound represented by the chemical formula BH and a compound represented by the chemical formula BD are mixed in a weight ratio of 25:1. Vacuum evaporation is performed on a layer of a certain thickness. Next, as a hole suppression layer, a compound represented by the chemical formula HB1 is applied... Vacuum evaporation was performed on the thickness. Next, compound B-1, prepared in the above synthesis example B-1, and the compound represented by LiQ below were mixed in a 1:1 weight ratio and... A thermal vacuum evaporation process is performed on the thickness of the material to form an electron transport and implantation layer. On this electron transport and implantation layer, lithium fluoride (LiF) is sequentially deposited... The thickness, using aluminum The cathode is formed by vapor deposition of a certain thickness, thereby manufacturing organic light-emitting devices.

[0678]

[0679] Experimental Examples 2 to 132 and Comparative Experimental Examples 1 to 11

[0680] In Experiment 1 above, the compound listed in Table 1 below was used instead of compound A-1 to form the hole transport auxiliary layer, and the compound listed in Table 1 below was used instead of compound B-1 to form the electron transport and injection layer. Otherwise, organic light-emitting devices of Experiment 2 to 132 and Comparative Experiment 1 to 11 were fabricated using the same method as in Experiment 1 above. A 10 mA / cm² pressure was applied to the organic light-emitting devices fabricated in the experimental and comparative experimental examples. 2When the current was applied, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. On the other hand, T95 refers to the time required for the brightness to decrease from the initial brightness (6000 nits) to 95%.

[0681]

[0682] Table 1

[0683]

[0684]

[0685]

[0686]

[0687]

[0688] As shown in Table 1 above, the organic light-emitting devices of Experimental Examples 1 to 132 have lower driving voltage, higher luminous efficiency, and longer lifetime compared with the organic light-emitting devices of Comparative Experimental Examples 1 to 11.

[0689] More specifically, the organic light-emitting devices of Examples 1 to 132 used the compound of Formula 1 of this application when forming the hole transport auxiliary layer, and used the compound of Formula 2 of this application when forming the electron transport and injection layer. By adjusting the HOMO energy level of the compound of Formula 1, the potential barrier between the light-emitting layer and the hole transport layer can be adjusted; by adjusting the LUMO energy level of the compound of Formula 2, the potential barrier between the light-emitting layer and the electron transport and injection layer can be adjusted.

[0690] Therefore, in the organic light-emitting devices of Experimental Examples 1 to 132, which simultaneously satisfy the requirements of using the compound of Chemical Formula 1 of this application for the hole transport auxiliary layer and the compound of Chemical Formula 2 of this application for the electron transport and injection layer, the hole-electron balance is appropriate, resulting in excellent voltage, efficiency, and / or lifetime characteristics.

[0691] In contrast, although the organic light-emitting devices of Experimental Examples 1 to 4 used the compound of Chemical Formula 1 of this application when forming the hole transport auxiliary layer, they used Alq3 instead of the compound of Chemical Formula 2 of this application when forming the electron transport layer. It can be confirmed that compared with the organic light-emitting devices of Experimental Examples 1 to 132, they have higher driving voltage, lower efficiency and shorter lifetime.

[0692] Although the organic light-emitting devices of Experimental Examples 5 and 6 used the compound of Chemical Formula 2 of this application when forming the electron transport layer, they used A5 as a diamine compound instead of the compound of Chemical Formula 1 of this application when forming the hole transport auxiliary layer. It can be confirmed that compared with the organic light-emitting devices of Experimental Examples 1 to 132, the driving voltage is high, the efficiency is low, and the lifetime is short.

[0693] Although the organic light-emitting device of Comparative Example 7 used the compound of Chemical Formula 1 of this application when forming the hole transport auxiliary layer, it used Ar4 of Chemical Formula 2 of this application, which is not a polycyclic aryl group but a hydrogen compound B3, when forming the electron transport layer. It can be confirmed that compared with the organic light-emitting devices of Examples 1 to 132, the driving voltage is high, the efficiency is low and the lifetime is short.

[0694] Although the organic light-emitting devices of Experimental Examples 8 and 9 used the compound of Chemical Formula 1 of this application when forming the hole transport auxiliary layer, they used compounds B4 and B5, which do not contain cyano groups and are different from the compound of Chemical Formula 2 of this application, when forming the electron transport layer. It can be confirmed that compared with the organic light-emitting devices of Experimental Examples 1 to 132, they have higher driving voltage, lower efficiency and shorter lifetime.

[0695] Although the organic light-emitting device of Comparative Example 10 used a compound of Chemical Formula 1 of this application in forming the hole transport auxiliary layer, it used compound B6, which has a similar structure to chemical formula 2 of this application but does not contain a cyano group, in forming the electron transport layer. It can be confirmed that compared with the organic light-emitting devices of Examples 1 to 132, the driving voltage is higher, the efficiency is lower, and the lifetime is shorter. In particular, it can be confirmed that the organic light-emitting device of Comparative Example 10, compared with the organic light-emitting device of Example 17 which used compound B-6 in forming the electron transport layer, has a higher driving voltage, lower efficiency, and shorter lifetime. Compound B-6 has the same structure as compound B6 except that it contains a cyano group.

[0696] Although the organic light-emitting device of Comparative Example 11 used the compound of Chemical Formula 2 of this application when forming the electron transport layer, it used a compound A6, which does not contain phenanthrene groups and is different from Chemical Formula 1 of this application, when forming the hole transport auxiliary layer. It can be confirmed that compared with the organic light-emitting devices of Examples 1 to 132, the driving voltage is high, the efficiency is low, and the lifetime is short.

Claims

1. An organic light-emitting device, comprising: anode, cathode, A first organic layer and a second organic layer are disposed between the anode and the cathode. The first organic layer contains a compound represented by the following chemical formula 1. The second organic layer contains a compound represented by the following chemical formula 2. [Chemical Formula 1] In the chemical formula 1, Ar1 and Ar2 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or a fused ring of substituted or unsubstituted aromatic ring and aliphatic ring. L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted divalent aryl group, or a substituted or unsubstituted divalent heteroaryl group. R1 is hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. R2 and R3 may be the same or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or when p or q is 2 or more, they may combine with adjacent groups to form substituted or unsubstituted rings. a, b, and c are integers from 0 to 3. When a is 2 or higher, two or more L1 values ​​are the same or different from each other. When b is 2 or higher, two or more L2 values ​​are the same or different from each other. When c is 2 or higher, two or more L3 values ​​are the same or different from each other. p and q are integers from 0 to 4. When p is 2 or more, two or more R2 values ​​are the same or different from each other. When q is 2 or more, two or more R3 values ​​are the same or different from each other. [Chemical Formula 2] In the chemical formula 2, Ar3 is a substituted or unsubstituted heteroaryl group. Ar4 is a substituted or unsubstituted polycyclic aryl group. L4 and L5 may be the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted divalent aryl group. R4 is either hydrogen or deuterium. d and e are integers from 0 to 3. When d is 2 or higher, two or more L4s are either the same or different. When e is 2 or higher, two or more L5s are either the same or different. r is an integer from 0 to 3. When r is 2 or more, two or more R4s are the same or different from each other.

2. The organic light-emitting device according to claim 1, wherein, Ar1 and Ar2 may be the same as or different from each other, each being hydrogen independently; deuterium; adamantyl alkyl group substituted or unsubstituted with deuterium; 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; spirodifluorenyl group substituted or unsubstituted with deuterium; phenanthryl group substituted or unsubstituted with deuterium; tetrahydronaphthyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms; carbazolyl group substituted or unsubstituted with deuterium; dibenzofuranyl group substituted or unsubstituted with deuterium; or dibenzothiophene group substituted or unsubstituted with deuterium.

3. The organic light-emitting device according to claim 1, wherein, L1 to L3 may be the same as or different from each other, and each is independently directly bonded; a divalent phenyl 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 substituted or unsubstituted with deuterium; a divalent terphenyl substituted or unsubstituted with deuterium; a divalent naphthyl substituted or unsubstituted with deuterium; a divalent fluorenyl 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 spirodifluorenyl substituted or unsubstituted with deuterium; a divalent phenanthryl substituted or unsubstituted with deuterium; a divalent carbazolyl substituted or unsubstituted with deuterium; a divalent dibenzofuranyl substituted or unsubstituted with deuterium; or a divalent dibenzothiopheneyl substituted or unsubstituted with deuterium.

4. The organic light-emitting device according to claim 1, wherein, R1 to R3 may be the same as or different from each other, and each is 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 carbazolyl group substituted or unsubstituted with deuterium.

5. The organic light-emitting device according to claim 1, wherein, Chemical Formula 1 is represented by any of the following compounds:

6. The organic light-emitting device according to claim 1, wherein, Chemical formula 2 is represented by the following chemical formula 2-1: [Chemical Formula 2-1] In the chemical formula 2-1, Ar4, L4, L5, R4, d, e, and r are the same as those defined in chemical formula 2. L6 and L7 may be the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted divalent aryl group. R5 and R6 may be the same as or different from each other, and each may be an independently substituted or unsubstituted aryl group. f and g are integers from 0 to 3. When f is 2 or more, two or more L6s are the same or different from each other. When g is 2 or more, two or more L7s are the same or different from each other.

7. The organic light-emitting device according to claim 1, wherein, Ar4 is a deuterated or unsubstituted fluoranthyl group, a deuterated or unsubstituted phenanthryl group, or a deuterated or unsubstituted triphenyl group.

8. The organic light-emitting device according to claim 1, wherein, L4 and L5 may be the same as or different from each other, and each is independently a directly bonded, divalent phenyl substituted or unsubstituted with a deuterium or an aryl group having 6 to 12 carbon atoms, or a divalent biphenyl substituted or unsubstituted with a deuterium.

9. The organic light-emitting device according to claim 1, wherein, Chemical formula 2 is represented by any of the following compounds:

10. The organic light-emitting device according to claim 1, wherein, One or more organic layers are further disposed between the anode and the cathode. The further added organic layer is a light-emitting layer.

11. The organic light-emitting device according to claim 10, wherein, The first organic layer is disposed between the anode and the light-emitting layer.

12. The organic light-emitting device according to claim 10, wherein, The second organic layer is disposed between the light-emitting layer and the cathode.

13. The organic light-emitting device according to claim 10, wherein, The light-emitting layer comprises a compound represented by the following chemical formula 3: [Chemical Formula 3] In the chemical formula 3, L20 and L21 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group. Ar20 and Ar21 may be the same as or different from each other, and each can be independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic. R201 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. r201 is an integer from 1 to 8. When r201 is 2 or more, two or more R201s are the same or different from each other.

14. The organic light-emitting device according to claim 1, wherein, The first organic layer is a hole injection layer, a hole transport layer, a hole injection and transport layer, or a hole transport auxiliary layer.

15. The organic light-emitting device according to claim 1, wherein, The second organic layer is an electron transport layer, an electron injection layer, or an electron transport and injection layer.

16. The organic light-emitting device according to claim 1, wherein, The second organic layer also contains metal coordination compounds.

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