Compounds and organic light emitting devices comprising the same

Abstract

This specification relates to compounds of chemical formula 1 and organic light-emitting devices containing them.

Description

Technical Field

[0001] This application claims priority to Korean Patent Application No. 10-2025-0017478, filed with the Korean Patent Office on February 11, 2025, the entire contents of which are contained in this specification.

[0002] This specification relates to compounds and organic light-emitting devices containing them. 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, electron blocking materials, light-emitting materials, hole blocking 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 compounds represented by chemical formula 1 and organic light-emitting devices containing them.

[0008] Solution to the problem

[0009] One embodiment of this specification provides a compound of the following chemical formula 1.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] L1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0014] L2 is a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0015] Ar can be a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a fused ring group consisting of a substituted or unsubstituted aromatic ring and an aliphatic ring.

[0016] R1 to R6 may be the same as or different from each other, and each may independently be a hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may be combined with adjacent groups to form a substituted or unsubstituted ring.

[0017] R7 can be hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0018] a, b, and d may be the same or different from each other, and each is an independent integer from 0 to 5.

[0019] c, e, and f may be the same or different from each other, and each is an independent integer from 0 to 4.

[0020] p and q may be the same or different from each other, and each is an independent integer from 0 to 3.

[0021] When a, b, c, d, e, f, p, and q are each more than 2, the groups within the parentheses may be the same or different from each other.

[0022] However, the compound represented by the above chemical formula 1 contains more than one deuterium.

[0023] In addition, one embodiment of the present invention provides an organic light-emitting device, comprising: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the aforementioned compound.

[0024] Invention Effects

[0025] The compounds described in this specification can be used as materials for the organic layer of organic light-emitting devices. The compounds according to at least one embodiment of this specification can achieve improved efficiency, lower driving voltage, and / or improved lifetime characteristics in organic light-emitting devices. In particular, the compounds described in this specification can be used as materials for hole injection, hole transport, hole injection and hole transport, or electron blocking. Attached Figure Description

[0026] Figure 1 The illustration shows an example of an organic light-emitting device in which a substrate 1, a first electrode 2, an organic layer 3, and a second electrode 4 are stacked in sequence.

[0027] Figure 2 The illustration shows an example of an organic light-emitting device comprising a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron transport and injection layer 10, and a second electrode 4, which are stacked in sequence.

[0028] Symbol Explanation

[0029] 1: Substrate

[0030] 2: First electrode

[0031] 3: Organic layer

[0032] 4: Second electrode

[0033] 5: Hole injection layer

[0034] 6: Hole transport layer

[0035] 7: Electron blocking layer

[0036] 8: Emissive layer

[0037] 9: Hole-blocking layer

[0038] 10: Electron transport and injection layer. Detailed Implementation

[0039] The following is a more detailed description of this instruction manual.

[0040] In this specification, when a part is indicated to "include / comprise" a certain element, unless otherwise stated, it means that other elements may be included, rather than excluding other elements.

[0041] 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.

[0042] In this specification, "adjacent" groups can refer to substituents that are substituted on an atom directly bonded to the atom substituted by the substituent, substituents that are stereomorphically closest to the substituent, or other substituents that are substituted on 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.

[0043] In this specification, "containing deuterium," "deuterated," or "deuterated" means that hydrogen at a substituted position in a compound is replaced by deuterium. In this specification, "overdeuterated" means a compound or group in which all hydrogen atoms in the molecule are replaced by deuterium, and has the same meaning as "100% deuterated."

[0044] In this specification, "X% deuterated", "degree of deuteration X%", or "deuteration substitution rate X%" means that X% of the hydrogen atoms at substituted positions in the structure are replaced by deuterium. The "deuteration substitution rate (%)" of a compound or group can be expressed as (number of deuterium atoms) / (number of deuterium atoms + number of hydrogen atoms). 100 (%). For example, when the structure is dibenzofuranyl, "25% deuterated" of the above dibenzofuranyl, "degree of deuteration 25%" of the above dibenzofuranyl, or "deuteration rate 25%" of the above dibenzofuranyl means that 2 out of the 8 hydrogens at the substituted positions of the above dibenzofuranyl are substituted with deuterium.

[0045] 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).

[0046] 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 integration.

[0047] In addition, when analyzing “degree of deuteration” or “deuteration rate” by TLC / MS (thin-layer chromatography / mass spectrometry), the substitution rate can be calculated based on the maximum value (intermediate value) of the distribution of molecular weight at the end of the reaction.

[0048] In this specification, D can represent deuterium.

[0049] In this specification, [ ] Dn The parentheses indicate that the structure contains n deuterium atoms. That is, n represents the number of deuterium atoms that substituted 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.

[0050] 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.

[0051] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen groups, cyano (-CN), silyl, 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 not having any substituents.

[0052] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, alkyl groups having 1 to 20 carbon atoms, and aryl groups having 6 to 30 carbon atoms, or substituted by two or more substituents linked together as exemplified above, or having no substituents.

[0053] In this specification, the connection of two or more substituents means that the hydrogen of any one substituent is replaced by another substituent. For example, the connection of two substituents can be achieved by linking a phenyl group with a naphthyl group. or Such substituents. Furthermore, the connection of three substituents includes not only the case of (substituent 1)-(substituent 2)-(substituent 3) sequentially linked, but also the case where (substituent 2) and (substituent 3) are linked to (substituent 1). For example, phenyl, naphthyl, and isopropyl can be linked to form... , or Such substituents. The same definition applies to cases where four or more substituents are connected.

[0054] Examples of the above-mentioned substituents are described below, but are not limited thereto.

[0055] Examples of halogen groups in this specification include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0056] In this specification, silyl groups can be represented by the chemical formula -SiY1Y2Y3, where Y1, Y2, and Y3 can each be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Specific examples of the aforementioned silyl groups include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited to these.

[0057] 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, n-propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited to these.

[0058] In this specification, the cycloalkyl group is not particularly limited, but preferably has 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.

[0059] In this specification, the aryl group is not particularly limited, but it is preferably an aryl group with 6 to 60 carbon atoms, which can be a monocyclic aryl or a polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. As the monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. As the polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, finadeninyl, peryl, phenyl, fluorene, etc., but is not limited thereto.

[0060] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure.

[0061] When the aforementioned fluorene group is replaced, it can become , Spirofluorene group, (9,9-dimethylfluorenyl) and Substituted fluorenyl groups such as (9,9-diphenylfluorenyl). However, it is not limited to this.

[0062] In this specification, a heteroaryl group comprises one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may comprise one or more atoms selected from N, O, P, S, Si, and Se. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. The heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include pyridyl, pyrroliyl, pyrimidinyl, pyridazinyl, furanyl, thiophenyl, imidazolyl, and thiazolyl. Azolyl, pyrazolyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, etc., but not limited to these.

[0063] In this specification, arylene refers to a divalent aryl group, and the description of aryl groups other than divalent can be referenced above. For example, phenylene refers to a divalent phenyl group, and biphenylene refers to a divalent biphenyl group.

[0064] In this specification, heteroaryl refers to a divalent heteroaryl group. For heteroaryl groups other than divalent, the above description may be used.

[0065] In this specification, "ring" refers to a hydrocarbon ring or heterocycle.

[0066] In this specification, the formation of a ring by bonding with adjacent groups refers to the formation of 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.

[0067] 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. In this specification, the above description of cycloalkyl groups may be referenced in relation to the aforementioned aliphatic hydrocarbon rings.

[0068] 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, phenaene, pyrene, tetraphenylene, phenazine, pentaphenylene, fluorene, indene, acenaphthene, benzo[a]fluorene, spirofluorene, etc., but are not limited to these. In this specification, the above description of aryl groups may be referenced in relation to the aforementioned aromatic hydrocarbon rings.

[0069] 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 ( ), aziridine ( ), Thioctane ( (etc.), but not limited to this.

[0070] 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 Indone, triazine, tetraazine, isoquinoline, quinoline, quinone, 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.

[0071] 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 means an increase in absolute value from the vacuum level in the negative direction.

[0072] In this specification, HOMO (highest occupied molecular orbital) refers to the molecular orbital function of the region where electrons are located with the highest energy level in the bonding region. LUMO (lowest unoccupied molecular orbital) refers to the molecular orbital function of the region where electrons are located with the lowest energy level 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.

[0073] In this specification, bandgap refers to the energy difference between the HOMO and LUMO levels, that is, the HOMO-LUMO bandgap.

[0074] 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).

[0075] Unless otherwise defined herein, all technical and scientific terms used herein 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, this specification, including definitions, takes precedence unless otherwise specified. Furthermore, materials, methods, and embodiments are illustrative only and not intended to be limiting.

[0076] 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.

[0077] One embodiment of this specification provides a compound represented by chemical formula 1.

[0078] The compounds of chemical formula 1 will now be described in detail.

[0079] [Chemical Formula 1]

[0080]

[0081] In the above chemical formula 1,

[0082] L1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0083] L2 is a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0084] Ar can be a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a fused ring group consisting of a substituted or unsubstituted aromatic ring and an aliphatic ring.

[0085] R1 to R6 may be the same as or different from each other, and each may independently be a hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may be combined with adjacent groups to form a substituted or unsubstituted ring.

[0086] R7 can be hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0087] a, b, and d may be the same or different from each other, and each is an independent integer from 0 to 5.

[0088] c, e, and f may be the same or different from each other, and each is an independent integer from 0 to 4.

[0089] p and q may be the same or different from each other, and each is an independent integer from 0 to 3.

[0090] When a, b, c, d, e, f, p, and q are each more than 2, the groups within the parentheses may be the same or different from each other.

[0091] However, the compound represented by the above chemical formula 1 contains more than one deuterium.

[0092] In one embodiment of this specification, the compound represented by the above chemical formula 1 is an amine compound, and the tetraphenyl group, as one of the substituents of the amine, plays a role in regulating the hole migration characteristics of the compound.

[0093] Therefore, when the compound represented by the above chemical formula 1 is used as a material for hole injection, hole transport, hole injection and transport, and electron blocking, the energy barrier between the light-emitting layer and the light-emitting layer is reduced due to the low HOMO energy level of the compound of chemical formula 1. Thus, the energy barrier between the light-emitting layer and the hole transport field containing one or more of the hole injection layer, hole transport layer, and hole injection and transport layer can be appropriately adjusted.

[0094] Furthermore, the compounds represented by the above chemical formula 1 have more than one deuterium substituted, which increases the stability of the structure and thus has the effect of improving the lifetime characteristics of organic light-emitting devices.

[0095] In one embodiment of this specification, the above-mentioned chemical formula 1 can be any one of the following chemical formulas 1-1 to 1-6.

[0096] [Chemical Formula 1-1]

[0097]

[0098] [Chemical Formula 1-2]

[0099]

[0100] [Chemical Formulas 1-3]

[0101]

[0102] [Chemical Formulas 1-4]

[0103]

[0104] [Chemical Formulas 1-5]

[0105]

[0106] [Chemical Formulas 1-6]

[0107]

[0108] In the above chemical formulas 1-1 to 1-6,

[0109] L2, Ar, R1 to R7, a, b, c, d, e, f, and q are defined the same as in chemical formula 1.

[0110] R11 to R19 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or may be combined with adjacent groups to form substituted or unsubstituted rings.

[0111] r11 to r19 may be the same as or different from each other, and each is an independent integer from 0 to 4.

[0112] When r11 to r19 are each more than 2, the groups within the parentheses may be the same or different from each other.

[0113] In one embodiment of this specification, L1 may be an arylene with 6 to 60 substituted or unsubstituted carbon atoms, or a heteroarylene with 2 to 60 substituted or unsubstituted carbon atoms.

[0114] In one embodiment of this specification, L1 may be an arylene with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroarylene with 2 to 30 substituted or unsubstituted carbon atoms.

[0115] In one embodiment of this specification, L1 may be an arylene with 6 to 20 substituted or unsubstituted carbon atoms, or a heteroarylene with 2 to 20 substituted or unsubstituted carbon atoms.

[0116] In one embodiment of this specification, L1 may be an arylene with 6 to 12 substituted or unsubstituted carbon atoms, or a heteroarylene with 2 to 12 substituted or unsubstituted carbon atoms.

[0117] In one embodiment of this specification, L1 may be an arylene group with 6 to 12 carbon atoms that is substituted or unsubstituted with deuterium, or a heteroarylene group with 2 to 12 carbon atoms that is substituted or unsubstituted with deuterium.

[0118] In one embodiment of this specification, L1 may be an arylene group with 6 to 12 carbon atoms, either substituted with deuterium or unsubstituted.

[0119] In one embodiment of this specification, L1 may be a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted divalent naphthyl, a substituted or unsubstituted divalent dibenzofuranyl, or a substituted or unsubstituted divalent dibenzothiophene.

[0120] In one embodiment of this specification, L1 may be a deuterated or unsubstituted phenylene, a deuterated or unsubstituted biphenylene, a deuterated or unsubstituted divalent dibenzofuranyl, or a deuterated or unsubstituted divalent dibenzothiophene.

[0121] In one embodiment of this specification, L1 may be a substituted or unsubstituted p-phenylene, a substituted or unsubstituted m-phenylene, a substituted or unsubstituted o-phenylene, a substituted or unsubstituted (p-phenylene)-(p-phenylene)yl, a substituted or unsubstituted (p-phenylene)-(m-phenylene)yl, a substituted or unsubstituted (p-phenylene)-(o-phenylene)yl, a substituted or unsubstituted divalent naphthyl, a substituted or unsubstituted divalent dibenzofuranyl, or a substituted or unsubstituted divalent dibenzothiopheneyl.

[0122] In one embodiment of this specification, L1 may be a deuterated or unsubstituted p-phenylene, a deuterated or unsubstituted meta-phenylene, a deuterated or unsubstituted o-phenylene, a deuterated or unsubstituted (p-phenylene)-(p-phenylene)yl, a deuterated or unsubstituted (p-phenylene)-(m-phenylene)yl, a deuterated or unsubstituted (p-phenylene)-(o-phenylene)yl, a deuterated or unsubstituted divalent naphthyl, a deuterated or unsubstituted divalent dibenzofuranyl, or a deuterated or unsubstituted divalent dibenzothiopheneyl.

[0123] In one embodiment of this specification, L1 may be a substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene.

[0124] In one embodiment of this specification, L1 may be a deuterated or unsubstituted phenylene or a deuterated or unsubstituted biphenylene.

[0125] In one embodiment of this specification, L1 may be a substituted or unsubstituted p-phenylene, a substituted or unsubstituted meta-phenylene, a substituted or unsubstituted o-phenylene, a substituted or unsubstituted (p-phenylene)-(p-phenylene)yl, a substituted or unsubstituted (p-phenylene)-(m-phenylene)yl, or a substituted or unsubstituted (p-phenylene)-(o-phenylene)yl.

[0126] In one embodiment of this specification, L1 may be a deuterated or unsubstituted p-phenylene, a deuterated or unsubstituted meta-phenylene, a deuterated or unsubstituted o-phenylene, a deuterated or unsubstituted (p-phenylene)-(p-phenylene)yl, a deuterated or unsubstituted (p-phenylene)-(m-phenylene)yl, or a deuterated or unsubstituted (p-phenylene)-(o-phenylene)yl.

[0127] In one embodiment of this specification, L2 may be a directly bonded, substituted or unsubstituted aryl group with 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 60 carbon atoms.

[0128] In one embodiment of this specification, L2 may be a directly bonded, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms.

[0129] In one embodiment of this specification, L2 may be a directly bonded, substituted or unsubstituted aryl group with 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 20 carbon atoms.

[0130] In one embodiment of this specification, L2 may be a directly bonded, substituted or unsubstituted aryl group with 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 12 carbon atoms.

[0131] In one embodiment of this specification, L2 may be a directly bonded, deuterated or unsubstituted aryl group with 6 to 12 carbon atoms, or a heteroaryl group with 2 to 12 carbon atoms, or a directly bonded, deuterated or unsubstituted aryl group.

[0132] In one embodiment of this specification, the L2 can be a arylene group with 6 to 12 carbon atoms that is directly bonded, or substituted with deuterium, or unsubstituted.

[0133] In one embodiment of this specification, L2 may be a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted divalent naphthyl, substituted or unsubstituted divalent dibenzofuranyl, or substituted or unsubstituted divalent dibenzothiophene.

[0134] In one embodiment of this specification, L2 may be a directly bonded, deuterated or unsubstituted phenylene, deuterated or unsubstituted biphenylene, deuterated or unsubstituted divalent naphthyl, deuterated or unsubstituted divalent dibenzofuranyl, or deuterated or unsubstituted divalent dibenzothiophene.

[0135] In one embodiment of this specification, L2 may be a directly bonded, substituted or unsubstituted p-phenylene, substituted or unsubstituted meta-phenylene, substituted or unsubstituted o-phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted divalent naphthyl, substituted or unsubstituted divalent dibenzofuranyl, or substituted or unsubstituted divalent dibenzothiophene.

[0136] In one embodiment of this specification, L2 may be a directly bonded, deuterated or unsubstituted p-phenylene, deuterated or unsubstituted meta-phenylene, deuterated or unsubstituted o-phenylene, deuterated or unsubstituted biphenylene, deuterated or unsubstituted divalent naphthyl, deuterated or unsubstituted divalent dibenzofuranyl, or deuterated or unsubstituted divalent dibenzothiophene.

[0137] In one embodiment of this specification, L2 may be a directly bonded, substituted, or unsubstituted phenylene oxide.

[0138] In one embodiment of this specification, L2 may be a directly bonded, deuterated, or unsubstituted phenylene oxide.

[0139] In one embodiment of this specification, L2 may be a directly bonded, substituted or unsubstituted p-phenylene, substituted or unsubstituted meta-phenylene, or substituted or unsubstituted o-phenylene.

[0140] In one embodiment of this specification, L2 may be a directly bonded, deuterated or unsubstituted p-phenylene, a deuterated or unsubstituted meta-phenylene, or a deuterated or unsubstituted o-phenylene.

[0141] In one embodiment of this specification, the aforementioned Ar may be an alkyl group having 1 to 60 carbon atoms that has been substituted or unsubstituted, a cycloalkyl group having 3 to 60 carbon atoms that has been substituted or unsubstituted, an aryl group having 6 to 60 carbon atoms that has been substituted or unsubstituted, a heteroaryl group having 2 to 60 carbon atoms that has been substituted or unsubstituted, or a fused ring group of an aromatic ring and an aliphatic ring having 7 to 60 carbon atoms that has been substituted or unsubstituted.

[0142] In one embodiment of this specification, the aforementioned Ar may be an alkyl group having 1 to 30 carbon atoms that is substituted or unsubstituted, a cycloalkyl group having 3 to 30 carbon atoms that is substituted or unsubstituted, an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted, a heteroaryl group having 2 to 30 carbon atoms that is substituted or unsubstituted, or a fused ring group of an aromatic ring and an aliphatic ring having 7 to 30 carbon atoms that is substituted or unsubstituted.

[0143] In one embodiment of this specification, the aforementioned Ar may be an alkyl group having 1 to 10 carbon atoms that has been substituted or unsubstituted, a cycloalkyl group having 3 to 20 carbon atoms that has been substituted or unsubstituted, an aryl group having 6 to 20 carbon atoms that has been substituted or unsubstituted, a heteroaryl group having 2 to 20 carbon atoms that has been substituted or unsubstituted, or a fused ring group of an aromatic ring and an aliphatic ring having 7 to 20 carbon atoms that has been substituted or unsubstituted.

[0144] In one embodiment of this specification, the aforementioned Ar may be an alkyl group having 1 to 6 carbon atoms that has been substituted or unsubstituted, a cycloalkyl group having 3 to 10 carbon atoms that has been substituted or unsubstituted, an aryl group having 6 to 12 carbon atoms that has been substituted or unsubstituted, a heteroaryl group having 2 to 12 carbon atoms that has been substituted or unsubstituted, or a fused ring group having 7 to 15 carbon atoms of an aromatic ring and an aliphatic ring that has been substituted or unsubstituted.

[0145] In one embodiment of this specification, the aforementioned Ar may be an alkyl group having 1 to 6 carbon atoms that is substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 10 carbon atoms that is substituted or unsubstituted with deuterium; an aryl group having 6 to 12 carbon atoms that is substituted or unsubstituted with one or more groups selected from deuterium, alkyl groups having 1 to 6 carbon atoms, and aryl groups having 6 to 10 carbon atoms; a heteroaryl group having 2 to 12 carbon atoms that is substituted or unsubstituted with deuterium; or a fused ring group having 7 to 15 carbon atoms of aromatic and aliphatic rings that is substituted or unsubstituted with one or more groups selected from deuterium and alkyl groups having 1 to 6 carbon atoms.

[0146] In one embodiment of this specification, the aforementioned Ar may be a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazole group, or a substituted or unsubstituted tetrahydronaphthyl group.

[0147] In one embodiment of this specification, the aforementioned Ar may be an alkyl group having 1 to 6 carbon atoms, either deuterated or unsubstituted; an adamantyl group, either deuterated or unsubstituted; a phenyl group, either deuterated or unsubstituted; a biphenyl group, either deuterated or unsubstituted; a terphenyl group, either deuterated or unsubstituted; a naphthyl group, either deuterated or unsubstituted; a phenanthryl group, either deuterated or unsubstituted; a fluorenyl group, either substituted or unsubstituted with one or more groups selected from deuterium, methyl, and phenyl; a dibenzofuranyl group, either deuterated or unsubstituted; a dibenzothiophenyl group, either deuterated or unsubstituted; a carbazoyl group, either deuterated or unsubstituted; or a tetrahydronaphthyl group, either substituted or unsubstituted with one or more groups selected from deuterium and methyl.

[0148] In one embodiment of this specification, the Ar can be a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, or a deuterated or unsubstituted naphthyl.

[0149] In one embodiment of this specification, R1 to R6 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, aryl group with 6 to 60 substituted or unsubstituted carbon atoms, or heteroaryl group with 2 to 60 substituted or unsubstituted carbon atoms, or combined with adjacent groups to form an aromatic hydrocarbon ring with 6 to 60 substituted or unsubstituted carbon atoms.

[0150] In one embodiment of this specification, R1 to R6 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms, or combined with adjacent groups to form an aromatic hydrocarbon ring with 6 to 30 substituted or unsubstituted carbon atoms.

[0151] In one embodiment of this specification, R1 to R6 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, aryl group with 6 to 20 substituted or unsubstituted carbon atoms, or heteroaryl group with 2 to 20 substituted or unsubstituted carbon atoms, or may be combined with adjacent groups to form an aromatic hydrocarbon ring with 6 to 20 substituted or unsubstituted carbon atoms.

[0152] In one embodiment of this specification, R1 to R6 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, aryl group with 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or heteroaryl group with 2 to 20 carbon atoms substituted or unsubstituted with deuterium, or combined with adjacent groups to form an aromatic hydrocarbon ring with 6 to 20 carbon atoms substituted or unsubstituted with one or more groups selected from deuterium and alkyl groups with 1 to 6 carbon atoms.

[0153] In one embodiment of this specification, R1 to R6 may be the same as or different from each other, and each may independently be hydrogen, deuterium, or an aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted by deuterium, or may be combined with adjacent groups to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms that is substituted or unsubstituted by one or more groups selected from deuterium and alkyl groups having 1 to 6 carbon atoms.

[0154] In one embodiment of this specification, R1 to R6 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted carbazolyl, or may be combined with adjacent groups to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted cyclohexane ring.

[0155] In one embodiment of this specification, R1 to R6 may be the same as or different from each other, and each may independently be hydrogen, deuterium, a deuterated or unsubstituted phenyl group, a deuterated or unsubstituted naphthyl group, or a deuterated or unsubstituted carbazolyl group, or a cyclohexane ring formed by combining with an adjacent group to form a deuterated or unsubstituted benzene ring, or a cyclohexane ring substituted or unsubstituted by one or more groups selected from deuterium and methyl.

[0156] In one embodiment of this specification, R1 to R6 may be the same as or different from each other, and each may independently be hydrogen or deuterium.

[0157] In one embodiment of this specification, R1 to R6 can be hydrogen.

[0158] In one embodiment of this specification, R1 to R6 can be deuterium.

[0159] In one embodiment of this specification, R1 is hydrogen.

[0160] In one embodiment of this specification, R1 is deuterium.

[0161] In one embodiment of this specification, R2 is hydrogen.

[0162] In one embodiment of this specification, R2 is deuterium.

[0163] In one embodiment of this specification, R3 is hydrogen.

[0164] In one embodiment of this specification, R3 is deuterium.

[0165] In one embodiment of this specification, R4 is hydrogen.

[0166] In one embodiment of this specification, R4 is deuterium.

[0167] In one embodiment of this specification, R5 is hydrogen.

[0168] In one embodiment of this specification, R5 is deuterium.

[0169] In one embodiment of this specification, R6 is hydrogen.

[0170] In one embodiment of this specification, R6 is deuterium.

[0171] In one embodiment of this specification, R7 can be hydrogen, deuterium, a halogen group, a cyano group, an aryl group with 6 to 60 substituted or unsubstituted carbon atoms, or a heteroaryl group with 2 to 60 substituted or unsubstituted carbon atoms.

[0172] In one embodiment of this specification, R7 can be hydrogen, deuterium, a halogen group, a cyano group, an aryl group with 6 to 60 substituted or unsubstituted carbon atoms, or a heteroaryl group with 2 to 60 substituted or unsubstituted carbon atoms.

[0173] In one embodiment of this specification, R7 may be hydrogen, deuterium, a halogen group, a cyano group, an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms.

[0174] In one embodiment of this specification, R7 can be hydrogen, deuterium, a halogen group, a cyano group, an aryl group with 6 to 20 substituted or unsubstituted carbon atoms, or a heteroaryl group with 2 to 20 substituted or unsubstituted carbon atoms.

[0175] In one embodiment of this specification, R7 can be hydrogen, deuterium, a halogen group, a cyano group, an aryl group with 6 to 20 carbon atoms that are substituted or unsubstituted with deuterium, or a heteroaryl group with 2 to 20 carbon atoms that are substituted or unsubstituted with deuterium.

[0176] In one embodiment of this specification, R7 may be hydrogen, deuterium, or an aryl group having 6 to 20 carbon atoms, either substituted with deuterium or unsubstituted.

[0177] In one embodiment of this specification, R7 may be hydrogen, deuterium, substituted or unsubstituted phenyl, or substituted or unsubstituted naphthyl.

[0178] In one embodiment of this specification, R7 can be hydrogen, deuterium, a deuterated or unsubstituted phenyl group, or a deuterated or unsubstituted naphthyl group.

[0179] In one embodiment of this specification, R7 may be hydrogen or deuterium.

[0180] In one embodiment of this specification, R7 may be hydrogen.

[0181] In one embodiment of this specification, R7 can be deuterium.

[0182] In one embodiment of this specification, a is an integer from 0 to 5. When a is 2 or more, two or more R1s are the same or different from each other.

[0183] In one embodiment of this specification, a is an integer from 0 to 5.

[0184] In one embodiment of this specification, a is 5.

[0185] In one embodiment of this specification, a is 4.

[0186] In one embodiment of this specification, a is 3.

[0187] In one embodiment of this specification, a is 2.

[0188] In one embodiment of this specification, a is 1.

[0189] In one embodiment of this specification, a is 0.

[0190] In one embodiment of this specification, b is an integer from 0 to 5, and when b is 2 or more, two or more R2s are the same or different from each other.

[0191] In one embodiment of this specification, b is an integer from 0 to 5.

[0192] In one embodiment of this specification, b is 5.

[0193] In one embodiment of this specification, b is 4.

[0194] In one embodiment of this specification, b is 3.

[0195] In one embodiment of this specification, b is 2.

[0196] In one embodiment of this specification, b is 1.

[0197] In one embodiment of this specification, b is 0.

[0198] In one embodiment of this specification, c is an integer from 0 to 4. When c is 2 or more, two or more R3s are the same or different from each other.

[0199] In one embodiment of this specification, c is an integer from 0 to 4.

[0200] In one embodiment of this specification, c is 4.

[0201] In one embodiment of this specification, c is 3.

[0202] In one embodiment of this specification, c is 2.

[0203] In one embodiment of this specification, c is 1.

[0204] In one embodiment of this specification, c is 0.

[0205] In one embodiment of this specification, d is an integer from 0 to 5. When d is 2 or more, two or more R4s are the same or different from each other.

[0206] In one embodiment of this specification, d is an integer from 0 to 5.

[0207] In one embodiment of this specification, d is 5.

[0208] In one embodiment of this specification, d is 4.

[0209] In one embodiment of this specification, d is 3.

[0210] In one embodiment of this specification, d is 2.

[0211] In one embodiment of this specification, d is 1.

[0212] In one embodiment of this specification, d is 0.

[0213] In one embodiment of this specification, e is an integer from 0 to 4. When e is 2 or more, two or more R5s are the same or different from each other.

[0214] In one embodiment of this specification, e is an integer from 0 to 4.

[0215] In one embodiment of this specification, e is 4.

[0216] In one embodiment of this specification, e is 3.

[0217] In one embodiment of this specification, e is 2.

[0218] In one embodiment of this specification, e is 1.

[0219] In one embodiment of this specification, e is 0.

[0220] In one embodiment of this specification, f is an integer from 0 to 4, and when f is 2 or more, two or more R6s are the same or different from each other.

[0221] In one embodiment of this specification, f is an integer from 0 to 4.

[0222] In one embodiment of this specification, f is 4.

[0223] In one embodiment of this specification, f is 3.

[0224] In one embodiment of this specification, f is 2.

[0225] In one embodiment of this specification, f is 1.

[0226] In one embodiment of this specification, f is 0.

[0227] In one embodiment of this specification, p is an integer from 0 to 3. When p is 2 or more, two or more L1s are the same or different from each other.

[0228] In one embodiment of this specification, p is an integer from 0 to 3.

[0229] In one embodiment of this specification, p is 3.

[0230] In one embodiment of this specification, p is 2.

[0231] In one embodiment of this specification, p is 1.

[0232] In one embodiment of this specification, p is 0.

[0233] In one embodiment of this specification, q is an integer from 0 to 3. When q is 2 or more, two or more L2s are the same or different from each other.

[0234] In one embodiment of this specification, q is an integer from 0 to 3.

[0235] In one embodiment of this specification, q is 3.

[0236] In one embodiment of this specification, q is 2.

[0237] In one embodiment of this specification, q is 1.

[0238] In one embodiment of this specification, q is 0.

[0239] In one embodiment of this specification, R11 to R19 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, aryl group with 6 to 60 substituted or unsubstituted carbon atoms, or heteroaryl group with 2 to 60 substituted or unsubstituted carbon atoms, or combined with adjacent groups to form an aromatic hydrocarbon ring with 6 to 60 substituted or unsubstituted carbon atoms.

[0240] In one embodiment of this specification, R11 to R19 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms, or combined with adjacent groups to form an aromatic hydrocarbon ring with 6 to 30 substituted or unsubstituted carbon atoms.

[0241] In one embodiment of this specification, R11 to R19 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, aryl group with 6 to 20 substituted or unsubstituted carbon atoms, or heteroaryl group with 2 to 20 substituted or unsubstituted carbon atoms, or combined with adjacent groups to form an aromatic hydrocarbon ring with 6 to 20 substituted or unsubstituted carbon atoms.

[0242] In one embodiment of this specification, R11 to R19 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, aryl group with 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or heteroaryl group with 2 to 20 carbon atoms substituted or unsubstituted with deuterium, or combined with adjacent groups to form an aromatic hydrocarbon ring with 6 to 20 carbon atoms substituted or unsubstituted with one or more groups selected from deuterium and alkyl groups with 1 to 6 carbon atoms.

[0243] In one embodiment of this specification, R11 to R19 may be the same as or different from each other, and each may independently be hydrogen, deuterium, or an aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted by deuterium, or may be combined with adjacent groups to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms that is substituted or unsubstituted by one or more groups selected from deuterium and alkyl groups having 1 to 6 carbon atoms.

[0244] In one embodiment of this specification, R11 to R19 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted carbazolyl, or may be combined with adjacent groups to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted cyclohexane ring.

[0245] In one embodiment of this specification, R11 to R19 may be the same as or different from each other, and each may independently be hydrogen, deuterium, a deuterated or unsubstituted phenyl group, a deuterated or unsubstituted naphthyl group, or a deuterated or unsubstituted carbazolyl group, or a cyclohexane ring formed by combining with an adjacent group to form a deuterated or unsubstituted benzene ring, or a cyclohexane ring substituted or unsubstituted by one or more groups selected from deuterium and methyl.

[0246] In one embodiment of this specification, R11 to R19 may be the same as or different from each other, and each may independently be hydrogen or deuterium, or may be combined with adjacent substituents to form a benzene ring substituted or unsubstituted with deuterium, or a cyclohexane ring substituted or unsubstituted with one or more groups selected from deuterium and methyl.

[0247] In one embodiment of this specification, R11 to R19 may be the same as or different from each other, and each may independently be hydrogen or deuterium.

[0248] In one embodiment of this specification, R11 to R19 may be hydrogen.

[0249] In one embodiment of this specification, R11 to R19 may be deuterium.

[0250] In one embodiment of this specification, R11 is hydrogen.

[0251] In one embodiment of this specification, R11 is deuterium.

[0252] In one embodiment of this specification, R12 is hydrogen.

[0253] In one embodiment of this specification, R12 is deuterium.

[0254] In one embodiment of this specification, R13 is hydrogen.

[0255] In one embodiment of this specification, R13 is deuterium.

[0256] In one embodiment of this specification, R14 is hydrogen.

[0257] In one embodiment of this specification, R14 is deuterium.

[0258] In one embodiment of this specification, R15 is hydrogen.

[0259] In one embodiment of this specification, R15 is deuterium.

[0260] In one embodiment of this specification, R16 is hydrogen.

[0261] In one embodiment of this specification, R16 is deuterium.

[0262] In one embodiment of this specification, R17 is hydrogen.

[0263] In one embodiment of this specification, R17 is deuterium.

[0264] In one embodiment of this specification, R18 is hydrogen.

[0265] In one embodiment of this specification, R18 is deuterium.

[0266] In one embodiment of this specification, R19 is hydrogen.

[0267] In one embodiment of this specification, R19 is deuterium.

[0268] In one embodiment of this specification, r11 to r19 may be the same as or different from each other, each being an independent integer from 0 to 4. When r11 to r19 are 2 or more, the groups within the parentheses may be the same as or different from each other.

[0269] In one embodiment of this specification, r11 is an integer from 0 to 4. When r11 is 2 or more, two or more R11s are the same or different from each other.

[0270] In one embodiment of this specification, r12 is an integer from 0 to 4. When r12 is 2 or more, two or more R12s are the same or different from each other.

[0271] In one embodiment of this specification, r13 is an integer from 0 to 4. When r13 is 2 or more, two or more R13s are the same or different from each other.

[0272] In one embodiment of this specification, r14 is an integer from 0 to 4. When r14 is 2 or more, two or more R14s are the same or different from each other.

[0273] In one embodiment of this specification, r15 is an integer from 0 to 4. When r15 is 2 or more, two or more R15s are the same or different from each other.

[0274] In one embodiment of this specification, r16 is an integer from 0 to 4. When r16 is 2 or more, two or more R16 are the same or different from each other.

[0275] In one embodiment of this specification, r17 is an integer from 0 to 4. When r17 is 2 or more, two or more R17s are the same or different from each other.

[0276] In one embodiment of this specification, r18 is an integer from 0 to 4. When r18 is 2 or more, two or more R18s are the same or different from each other.

[0277] In one embodiment of this specification, r19 is an integer from 0 to 4. When r19 is 2 or more, two or more R19s are the same or different from each other.

[0278] In one embodiment of this specification, r11 to r19 are 4.

[0279] In one embodiment of this specification, r11 to r19 are 3.

[0280] In one embodiment of this specification, r11 to r19 are 2.

[0281] In one embodiment of this specification, r11 to r19 are 1.

[0282] In one embodiment of this specification, r11 to r19 are 0.

[0283] In one embodiment of this specification, the deuterium substitution rate of the compound represented by the above chemical formula 1 may be from 20% to 100%.

[0284] In one embodiment of this specification, the deuterium substitution rate of the compound represented by the above-described chemical formula 1 can, for example, be 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, 50% or more, 55% or more, 60% or more, 70% or more, 80% or more, or 90% or more, or can be less than 100%, less than 90%, less than 80%, less than 75%, less than 70%, less than 65%, less than 60%, less than 55%, less than 50%, less than 45%, less than 40%, less than 35%, less than 30%, or less than 25%. The deuterium substitution rate of the compound represented by the above-described chemical formula 1 can be within the range selected from any of the lower limits listed above and any of the upper limits listed above. For example, the deuterium substitution rate of the compound represented by Chemical Formula 1 can be 20% to 80%, 25% to 80%, 25% to 75%, 30% to 75%, 30% to 70%, 35% to 70%, or 35% to 65%. Furthermore, the deuterium substitution rate of the compound represented by the above Chemical Formula 1 can, for example, be 20% to 30%, 30% to 40%, 40% to 50%, 50% to 60%, 60% to 70%, 70% to 80%, or 40% to 80%.

[0285] When the deuterium substitution rate of the compounds represented by the above chemical formula 1 exceeds the aforementioned range, the synthesis conditions of the compounds become harsh, and the purity of the compounds decreases, thus failing to improve the lifetime characteristics of organic light-emitting devices. Furthermore, when the deuterium substitution rate of the compounds represented by the above chemical formula 1 is below the aforementioned range, compared with compounds containing protium, the degree of improvement in structural stability is lower, thus failing to improve the lifetime characteristics of organic light-emitting devices.

[0286] In one embodiment of this specification, the above-mentioned chemical formula 1 can be any of the following compounds.

[0287]

[0288]

[0289]

[0290]

[0291] In the above compounds, n is an integer greater than or equal to 1.

[0292] According to one embodiment of this specification, the compound represented by chemical formula 1 can be manufactured with a core structure as described in the manufacturing examples below. Substituents can be combined using methods known in the art, and the type, position, or number of substituents can be varied according to techniques known in the art.

[0293] In this specification, compounds with various band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above-described chemical formula 1. Furthermore, in this specification, the HOMO and LUMO energy levels of the compound can also be tuned by introducing various substituents into the core structure as described above.

[0294] In addition, one embodiment of this specification provides an organic light-emitting device comprising the above-described compound.

[0295] The following section explains organic light-emitting devices.

[0296] In this invention, the term "layer" is used interchangeably with "film" primarily used in this technical field, referring to a coating covering the target area. The size of the "layer" is not limited; each "layer" can be the same or different in size. According to one embodiment, the size of a "layer" can be equal to the entire device, equivalent to the size of a specific functional area, or as small as a single sub-pixel.

[0297] 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.

[0298] In this specification, the meaning of a specific substance A being contained in layer C or layer D includes i) being contained in layer C or more than one layer, or ii) being contained in layer D or more than one layer, or iii) being contained in layer C or more than one layer and layer D or more than one layer respectively.

[0299] In this specification, n-type refers to a substance that can remove electrons from the matrix material (the material of the organic layer), and may use generally known substances, but is not limited to them. That is, n-type can be defined as a substance that has the property of being able to donate electrons to the LUMO (lowest unoccupied molecular orbital) energy level of the matrix. Conversely, p-type is a substance that, when a layer is formed using only p-type material, accepts electrons from the HOMO (highest occupied molecular orbital) energy level of the material located in the adjacent cathode direction, thereby generating holes in the adjacent cathode direction material; or, when p-type material is doped into any matrix, accepts electrons from the HOMO of the matrix material, thereby generating an equal amount of holes in the HOMO of the matrix. Therefore, when a layer is formed using only p-type material, the closer the HOMO of the material located in the cathode direction is to the LUMO of the p-type material, the easier it is to steal electrons from the HOMO of the adjacent layer, thereby generating holes in the HOMO of the adjacent layer. Furthermore, when p-type material is doped into any matrix, the closer the LUMO of the p-type material is to the HOMO of the matrix, the easier it is to steal electrons and generate holes in the matrix.

[0300] An organic light-emitting device according to one embodiment of this specification includes: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers may contain the aforementioned compound.

[0301] According to one embodiment of this specification, an organic light-emitting device is formed by using the compound of the above-described chemical formula 1 to form one or more organic layers. Otherwise, it can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0302] 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.

[0303] In one embodiment of this specification, the organic layer of the organic light-emitting device can be formed as a single-layer structure or as a multi-layer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of the present invention may have a structure comprising one or more of the following as organic layers: a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, a hole blocking 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 thereto, and may include fewer or more organic layers.

[0304] In one embodiment of this specification, the organic light-emitting device may include a light-emitting layer, wherein an organic layer comprising a compound represented by the above-described chemical formula 1 may be located between the first electrode and the light-emitting layer.

[0305] In one embodiment of this specification, the organic layer may include a light-emitting layer, which may contain a compound represented by the following chemical formula 2.

[0306] [Chemical Formula 2]

[0307]

[0308] In the above chemical formula 2,

[0309] 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 heteroaryl group.

[0310] Ar20 and Ar21 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0311] 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 heteroaryl group.

[0312] 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.

[0313] 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 with 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 30 carbon atoms.

[0314] 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, a deuterated or unsubstituted divalent biphenyl, a deuterated or unsubstituted divalent naphthyl, a divalent dibenzofuranyl, or a divalent dibenzothiophene.

[0315] In one embodiment of this specification, L20 and L21 are directly bonded.

[0316] 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 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms.

[0317] In one embodiment of this specification, Ar20 and Ar21 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, either substituted or unsubstituted, or a monocyclic to tetracyclic heteroaryl group with 6 to 20 carbon atoms.

[0318] 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. The aryl-substituted or unsubstituted thiophene group; the dibenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; the naphthobenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; the dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or the naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0319] 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 deuterated or unsubstituted naphthyl group.

[0320] In one embodiment of this specification, R201 is hydrogen.

[0321] In one embodiment of this specification, the above-mentioned chemical formula 2 may be represented by the following compounds, but is not limited thereto.

[0322]

[0323] In an organic light-emitting device according to one embodiment of this specification, the organic layer may include one or more of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer, wherein one or more of the aforementioned layers may contain a compound represented by the aforementioned chemical formula 1.

[0324] When one or more of the aforementioned hole injection layer, hole transport layer, hole injection and transport layer, and electron blocking layer contain a compound represented by the aforementioned chemical formula 1, the HOMO has a low energy level. By appropriately adjusting the energy barrier of the light-emitting layer, it can improve the hole injection characteristics of organic light-emitting devices.

[0325] In an organic light-emitting device according to one embodiment of this specification, the aforementioned organic layer may include one or more layers selected from a hole transport layer, a hole injection layer, a hole injection and transport layer, and an electron blocking layer, and a light-emitting layer. When one or more layers selected from the aforementioned hole transport layer, hole injection layer, hole injection and transport layer, and electron blocking layer contain a compound represented by the aforementioned chemical formula 1, and the aforementioned light-emitting layer contains a compound represented by the aforementioned chemical formula 2, the energy barrier can be appropriately adjusted because the difference in HOMO energy levels between the compounds is reduced.

[0326] In one embodiment of this specification, the organic layer may include a hole injection layer, which may contain a compound represented by the above chemical formula 1.

[0327] In one embodiment of this specification, the organic layer may include a hole transport layer, which may contain a compound represented by the above chemical formula 1.

[0328] In one embodiment of this specification, the organic layer may include a hole injection and transport layer, which may contain a compound represented by the above chemical formula 1.

[0329] In one embodiment of this specification, the organic layer may include an electron blocking layer, which may contain a compound represented by the above chemical formula 1.

[0330] In one embodiment of this specification, one or more organic layers may be further disposed between the first electrode and the second electrode of the organic light-emitting device. The organic layer may further include one or more of the following: a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron transport and injection layer.

[0331] 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.

[0332] In one embodiment of this specification, when the organic light-emitting device includes two or more hole injection layers, the two or more hole injection layers may contain the same or different substances.

[0333] In one embodiment of this specification, when the organic light-emitting device includes two or more hole transport layers, the two or more hole transport layers may contain the same or different substances.

[0334] In one embodiment of this specification, when the organic light-emitting device includes two or more hole injection and transport layers, the two or more hole injection and transport layers may contain the same or different substances.

[0335] In one embodiment of this specification, when the organic light-emitting device includes two or more electron blocking layers, the two or more electron blocking layers may contain the same or different substances.

[0336] In one embodiment of this specification, the thickness of the organic layer containing the compound represented by the above chemical formula 1 is 10 Å to 1300 Å, preferably 30 Å to 800 Å, and more preferably 50 Å to 300 Å.

[0337] In one embodiment of this specification, the first electrode is the anode and the second electrode is the cathode.

[0338] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0339] 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 stacked on a substrate (normal type).

[0340] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with a structure (inverted type) in which a cathode, one or more organic layers and an anode are stacked on a substrate.

[0341] For example, the organic light-emitting device described above can have a stacked structure as shown below, but is not limited to this.

[0342] (1) Anode / hole transport layer / light-emitting layer / cathode

[0343] (2) Anode / hole injection layer / hole transport layer / light emission layer / cathode

[0344] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0345] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0346] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0347] (6) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / cathode

[0348] (7) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0349] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / cathode

[0350] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0351] (10) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0352] (11) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0353] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emission layer / electron transport layer / cathode

[0354] (13) Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0355] (14) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0356] (15) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0357] (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0358] (17) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0359] (18) Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron transport and injection layer / Cathode

[0360] The organic light-emitting device according to one embodiment of this specification can have the following structure: Figure 1 or Figure 2 The structure shown is not limited to this.

[0361] Figure 1 The diagram illustrates the structure of an organic light-emitting device in which a first electrode 2, an organic layer 3, and a second electrode 4 are sequentially stacked on a substrate 1. In the structure described above, the compound represented by the above-described chemical formula 1 may be included in the organic layer 3.

[0362] Figure 2The diagram illustrates the structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron transport and injection layer 10, and a second electrode 4 are sequentially stacked on a substrate 1. In the structure described above, the compound represented by the above-described chemical formula 1 may be included in one or more of the hole injection layer 5, the hole transport layer 6, and the electron blocking layer 7.

[0363] 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, one or more organic layers are formed on the anode, including one selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron transport and injection layer. 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.

[0364] The aforementioned organic layer can be a multilayer structure including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport 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.

[0365] 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; or 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.

[0366] 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.

[0367] 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 thickness is too thick.

[0368] 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.

[0369] [Chemical formula HI-1]

[0370]

[0371] In the above chemical formula HI-1,

[0372] At least one of X'1 to X'6 is N, and the rest are CH.

[0373] 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.

[0374] In one embodiment of this specification, X'1 to X'6 are N.

[0375] In one embodiment of this specification, R309 to R314 are cyano groups.

[0376] 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.

[0377]

[0378] 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.

[0379] 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.

[0380] [Chemical formula HT-1]

[0381]

[0382] In the above chemical formula HT-1,

[0383] 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.

[0384] 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.

[0385] 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.

[0386] 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.

[0387] 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.

[0388] 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.

[0389] In one embodiment of this specification, R403 to R406 are phenyl.

[0390] 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.

[0391] 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.

[0392] In one embodiment of this specification, L401 and L403 are phenylene oxides.

[0393] In one embodiment of this specification, L402 is a divalent carbazole group substituted with a naphthyl group.

[0394] In one embodiment of this specification, the above chemical formula HT-1 may be represented by the following compounds, but is not limited thereto.

[0395]

[0396] 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.

[0397] An electron blocking layer may be disposed between the hole transport layer and the light-emitting layer. This electron blocking layer may use the aforementioned compounds or materials known in the art.

[0398] 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; spiro compounds; polyfluorene, fluorene, etc., but not limited to these.

[0399] As the main material for the luminescent layer, there are 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.

[0400] 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 (planar tris(2-phenylpyridine)iridium) and fac 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), stilbeneylarylene (DSA), PFO-based polymers, PPV-based polymers, etc., can be used, but are not limited to these.

[0401] In one embodiment of this specification, the light-emitting dopant comprises a compound represented by the following chemical formula D-1, but is not limited thereto.

[0402] [Chemical Formula D-1]

[0403]

[0404] In the above chemical formula D-1,

[0405] 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.

[0406] t5 and t6 are each integers from 1 to 4.

[0407] When t5 is 2 or more, the two or more T5 values ​​are the same or different from each other.

[0408] When t6 is 2 or more, the two or more T6 are the same or different from each other.

[0409] In one embodiment of this specification, T1 to T6 may be the same as or different from each other, and each independently consists of 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.

[0410] In 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.

[0411] In 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.

[0412] In one embodiment of this specification, the above chemical formula D-1 may be represented by the following compounds, but is not limited thereto.

[0413]

[0414] A hole blocking layer can be disposed between the electron transport layer and the light-emitting layer. This hole blocking layer prevents holes from reaching the cathode and can typically be formed using the same conditions as the hole injection layer. Specifically, there are... Diazole or triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc., but not limited to these.

[0415] In one embodiment of this specification, the hole-blocking layer comprises a compound represented by the following chemical formula HB-1, but is not limited thereto.

[0416] [Chemical formula HB-1]

[0417]

[0418] In the above chemical formula HB-1,

[0419] At least one of Z1 to Z3 is N, and the rest are CH.

[0420] 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.

[0421] 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.

[0422] In one embodiment of this specification, L601 and L602 may be the same as or different from each other, and each is independently a monocyclic or polycyclic arylene group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0423] In one embodiment of this specification, L601 and L602 may be the same as or different from each other, and each is independently a phenylene, a divalent biphenyl, or a divalent naphthyl.

[0424] 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.

[0425] In one embodiment of this specification, Ar601 to Ar603 may be the same as or different from each other, and each is independently phenyl or triphenylene.

[0426] 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.

[0427]

[0428] The aforementioned electron transport layer facilitates 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 nm 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.

[0429] 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.

[0430] 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, but is not limited thereto.

[0431] 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.

[0432] 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.

[0433] In one embodiment of this specification, the electron transport and injection layer comprises a compound represented by the following chemical formula ET-1, but is not limited thereto.

[0434] [Chemical formula ET-1]

[0435]

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

[0437] At least one of Z11 to Z13 is N, and the rest are CH.

[0438] At least one of Z14 to Z16 is N, and the rest are CH.

[0439] L701 is a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heteroaryl group.

[0440] Ar701 to Ar704 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.

[0441] l701 is an integer from 1 to 4. When l701 is a complex number, l701 can be the same or different from each other.

[0442] In one embodiment of this specification, L701 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0443] In one embodiment of this specification, L701 is a phenylene, a divalent biphenyl, or a divalent naphthyl.

[0444] In one embodiment of this specification, L701 is a phenylene group or a divalent naphthyl group.

[0445] In one embodiment of this specification, Ar701 to Ar704 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.

[0446] In one embodiment of this specification, Ar701 to Ar704 are phenyl groups.

[0447] In one embodiment of this specification, the above-mentioned chemical formula ET-1 may be represented by the following compounds, but is not limited thereto.

[0448]

[0449] In one embodiment of this specification, the electron transport and injection layer may further comprise a metal coordination compound.

[0450] In one embodiment of this specification, the electron transport and injection layer may further comprise a lithium metal coordination compound.

[0451] In one embodiment of this specification, the electron transport and injection layer may further comprise lithium 8-hydroxyquinoline (LiQ).

[0452] In one embodiment of this specification, the electron transport and injection layer comprises a compound represented by the chemical formula ET-1, and may also comprise a metal coordination compound, wherein the weight ratio of the compound represented by the chemical formula ET-1 to the metal coordination compound may be 1:9 to 9:1.

[0453] In one embodiment of this specification, the electron transport and injection layer comprises a compound represented by the chemical formula ET-1, and may also comprise a metal coordination compound. The weight ratio of the compound represented by the chemical formula ET-1 to the metal coordination compound may be 2:8 to 8:2, 3:7 to 7:3, or 4:6 to 6:4.

[0454] In one embodiment of this specification, the electron transport and injection layer comprises a compound represented by the chemical formula ET-1, and may also comprise a metal coordination compound, wherein the weight ratio of the compound represented by the chemical formula ET-1 to the metal coordination compound may be 5:5.

[0455] In one embodiment of this specification, a capping layer (CPL) may be deposited onto the outer contour of the cathode. The capping layer serves to maximize the light extraction effect or prevent the degradation of the organic light-emitting device, and may contain capping layer materials known in the art.

[0456] 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.

[0457] 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., but are not limited thereto.

[0458] The following experimental examples will be provided to illustrate this specification in detail. However, the embodiments described herein can be modified in various other forms and should not be construed as limiting the scope of this application to the embodiments detailed below. The embodiments of this application are provided to provide a more complete explanation of this specification to those skilled in the art.

[0459] <Synthesis example>

[0460] Synthesis Example 1. Synthesis of Compound 1

[0461] Step 1) Synthesis of Compound 1-A

[0462]

[0463] Toluene (200 ml) was added to 9-(4-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol), N-phenyl-[1,1':2',1'':2'',1'''-tetraphenyl]-2-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. Bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (20 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 1-A (35.0 g, yield 77.76%). (MS [M+H]) + =650)

[0464] Step 2) Synthesis of Compound 1

[0465]

[0466] Compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthetic Example 1 was added to benzene-d6 (60 ml) and completely dissolved. Trifluoromethanesulfonic acid (2.7 ml, 30.78 mmol) was then added, and the mixture was stirred for 25 minutes. After the reaction was complete, dichloromethane was added, and the mixture was subjected to chromatography 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 1 (15.5 g, yield 76.20%). (MS [M+H]) + =661)

[0467] Synthesis Example 2. Synthesis of Compound 2

[0468]

[0469] Compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthetic Example 1 was added to benzene-d6 (200 ml) and completely dissolved. Trifluoromethanesulfonic acid (8.2 ml, 92.33 mmol) was then added, and the mixture was stirred for 25 minutes. After the reaction was complete, dichloromethane was added, and the mixture was subjected to chromatography 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 2 (16.0 g, yield 77.82%). (MS [M+H]) + =668)

[0470] Synthesis Example 3. Synthesis of Compound 3

[0471] Step 1) Synthesis of compound 3-A

[0472]

[0473] Compound 3-A (35.0 g, 77.76% yield) was obtained by substituting N-phenyl-[1,1':2',1'':4'',1'''-tetraphenyl]-2-amine (28.08 g, 70.64 mmol) with N-phenyl-[1,1':2'',1'''-tetraphenyl]-2-amine (28.08 g, 70.64 mmol), except that it was obtained by the same method as step 1 of Synthetic Example 1 above. (MS[M+H) + =650)

[0474] Step 2) Synthesis of Compound 3

[0475]

[0476] Compound 3 (15.5 g, yield 76.20%) was obtained by replacing compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 1 with compound 3-A (20.0 g, 30.78 mmol), except that compound 3 was obtained by the same method as in step 2 of synthesis example 1. (MS[M+H]) + =661)

[0477] Synthesis Example 4. Synthesis of Compound 4

[0478]

[0479] Compound 3-A (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 3 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 1. Otherwise, compound 4 (16.00 g, yield 77.82%) was obtained by the same method as in synthesis example 2. (MS[M+H]) + =668)

[0480] Synthesis Example 5. Synthesis of Compound 5

[0481] Step 1) Synthesis of compound 5-A

[0482]

[0483] Compound 5-A (35.0 g, 77.76% yield) was obtained by substituting N-phenyl-[1,1':2',1'':2'',1'''-tetraphenyl]-4-amine (28.08 g, 70.64 mmol) with N-phenyl-[1,1':2'',1'''-tetraphenyl]-2-amine (28.08 g, 70.64 mmol), except that it was obtained by the same method as in step 1 of Synthetic Example 1 above. (MS[M+H) + =650)

[0484] Step 2) Synthesis of Compound 5

[0485]

[0486] Compound 5-A (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 5 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 1. Otherwise, compound 5 (15.5 g, yield 76.20%) was obtained by the same method as in step 2 of synthesis example 1. (MS[M+H]) + =661)

[0487] Synthesis Example 6. Synthesis of Compound 6

[0488]

[0489] Compound 5-A (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 5 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 1. Otherwise, compound 6 (16.00 g, yield 77.82%) was obtained by the same method as in synthesis example 2. (MS[M+H]) + =668)

[0490] Synthesis Example 7. Synthesis of Compound 7

[0491] Step 1) Synthesis of compound 7-A

[0492]

[0493] Compound 7-A (40.00 g, 79.56% yield) was obtained by substituting N-([1,1'-biphenyl]-4-yl)-[1,1':2',1'':2'',1'''-tetraphenyl]-2-amine (33.46 g, 70.64 mmol) with N-phenyl-[1,1':2',1''':2'',1'''-tetraphenyl]-2-amine (28.08 g, 70.64 mmol), except that it was obtained by the same method as in step 1 of Synthetic Example 1 above. (MS[M+H) + =726)

[0494] Step 2) Synthesis of Compound 7

[0495]

[0496] Compound 7-A (20.0 g, 27.55 mmol) obtained in step 1 of synthesis example 7 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 1. Otherwise, compound 7 (16.0 g, yield 78.69%) was obtained by the same method as in step 2 of synthesis example 1. (MS[M+H]) + =738)

[0497] Synthesis Example 8. Synthesis of Compound 8

[0498]

[0499] Compound 7-A (20.0 g, 27.55 mmol) obtained in step 1 of Synthesis Example 7 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthesis Example 1. Otherwise, compound 8 (16.0 g, yield 77.84%) was obtained by the same method as in Synthesis Example 2. (MS[M+H)) + =746)

[0500] Synthesis Example 9. Synthesis of Compound 9

[0501] Step 1) Synthesis of compound 9-A

[0502]

[0503] Compound 9-A (40.00 g, 79.56% yield) was obtained by substituting N-([1,1'-biphenyl]-3-yl)-[1,1':2',1'':2'',1'''-tetraphenyl]-2-amine (33.46 g, 70.64 mmol) with N-phenyl-[1,1':2',1''':2'',1'''-tetraphenyl]-2-amine (28.08 g, 70.64 mmol), except that it was obtained by the same method as in step 1 of Synthetic Example 1 above. (MS[M+H) + =726)

[0504] Step 2) Synthesis of Compound 9

[0505]

[0506] Compound 9-A (20.0 g, 27.55 mmol) obtained in step 1 of synthesis example 9 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 1. Otherwise, compound 9 (16.0 g, yield 78.69%) was obtained by the same method as in step 2 of synthesis example 1. (MS[M+H]) + =738)

[0507] Synthesis Example 10. Synthesis of Compound 10

[0508]

[0509] Compound 10 (16.0 g, 77.84% yield) was obtained by replacing compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 1 with compound 9-A (20.0 g, 27.55 mmol) obtained in step 1 of synthesis example 1 above. Otherwise, compound 10 was obtained by the same method as in synthesis example 2 above. (MS[M+H]) + =746)

[0510] Synthesis Example 11. Synthesis of Compound 11

[0511] Step 1) Synthesis of compound 11-A

[0512]

[0513] Compound 11-A (39.00 g, 77.57% yield) was obtained by substituting N-([1,1'-biphenyl]-2-yl)-[1,1':2',1'':2'',1'''-tetraphenyl]-2-amine (33.46 g, 70.64 mmol) with N-phenyl-[1,1':2',1''':2'',1'''-tetraphenyl]-2-amine (28.08 g, 70.64 mmol), except that it was obtained by the same method as in step 1 of Synthetic Example 1 above. (MS[M+H) + =726)

[0514] Step 2) Synthesis of Compound 11

[0515]

[0516] Compound 11-A (20.0 g, 27.55 mmol) obtained in step 1 of Synthesis Example 11 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthesis Example 1. Otherwise, compound 11 (16.0 g, yield 78.69%) was obtained by the same method as in step 2 of Synthesis Example 1. (MS[M+H]) + =738)

[0517] Synthesis Example 12. Synthesis of Compound 12

[0518]

[0519] Compound 11-A (20.0 g, 27.55 mmol) obtained in step 1 of Synthesis Example 11 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthesis Example 1. Otherwise, compound 12 (16.0 g, yield 77.84%) was obtained by the same method as in Synthesis Example 2. (MS[M+H]) + =746)

[0520] Synthesis Example 13. Synthesis of Compound 13

[0521] Step 1) Synthesis of compound 13-A

[0522]

[0523] Compound 13-A (35.0 g, 77.76% yield) was obtained by using 9-(3-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol) instead of 9-(4-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol), except that it was obtained by the same method as in step 1 of Synthetic Example 1 above. (MS[M+H])+ =650)

[0524] Step 2) Synthesis of Compound 13

[0525]

[0526] Compound 13 (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 13 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 1. Otherwise, compound 13 (15.5 g, yield 76.20%) was obtained by the same method as in step 2 of synthesis example 1. (MS[M+H]) + =661)

[0527] Synthesis Example 14. Synthesis of Compound 14

[0528]

[0529] Compound 13-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthesis Example 13 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthesis Example 1. Otherwise, compound 14 (16.00 g, yield 77.82%) was obtained by the same method as in Synthesis Example 2. (MS[M+H)) + =668)

[0530] Synthesis Example 15. Synthesis of Compound 15

[0531] Step 1) Synthesis of Compound 15-A

[0532]

[0533] Compound 15-A (35.0 g, 77.76% yield) was obtained by using 9-(3-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol) instead of 9-(4-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol) and N-phenyl-[1,1':2',1'':4'',1'''-tetraphenyl]-2-amine (28.08 g, 70.64 mmol) instead of N-phenyl-[1,1':2',1''':2'',1'''-tetraphenyl]-2-amine (28.08 g, 70.64 mmol) in the same manner as in step 1 of Synthetic Example 1 above. + =650)

[0534] Step 2) Synthesis of Compound 15

[0535]

[0536] Compound 15-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthesis Example 1 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthesis Example 1. Otherwise, compound 15 (15.5 g, yield 76.20%) was obtained by the same method as in step 2 of Synthesis Example 1. (MS[M+H]) + =661)

[0537] Synthesis Example 16. Synthesis of Compound 16

[0538]

[0539] Compound 15-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthesis Example 15 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthesis Example 1. Otherwise, compound 16 (16.00 g, yield 77.82%) was obtained by the same method as in Synthesis Example 2. (MS[M+H]) + =668)

[0540] Synthesis Example 17. Synthesis of Compound 17

[0541] Step 1) Synthesis of compound 17-A

[0542]

[0543] Compound 17-A (35.0 g, 77.76% yield) was obtained by using 9-(3-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol) instead of 9-(4-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol) and N-phenyl-[1,1':2',1'':2'',1'''-tetraphenyl]-4-amine (28.08 g, 70.64 mmol) instead of N-phenyl-[1,1':2',1''':2'',1'''-tetraphenyl]-2-amine (28.08 g, 70.64 mmol) in the same manner as in step 1 of Synthetic Example 1 above. (MS[M+H) + =650)

[0544] Step 2) Synthesis of Compound 17

[0545]

[0546] Compound 17-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthesis Example 17 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthesis Example 1. Otherwise, compound 17 (15.5 g, yield 76.20%) was obtained by the same method as in step 2 of Synthesis Example 1. (MS[M+H]) + =661)

[0547] Synthesis Example 18. Synthesis of Compound 18

[0548]

[0549] Compound 17-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthesis Example 17 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthesis Example 1. Otherwise, compound 18 (16.00 g, yield 77.82%) was obtained by the same method as in Synthesis Example 2. (MS[M+H)) + =668)

[0550] Synthesis Example 19. Synthesis of Compound 19

[0551] Step 1) Synthesis of compound 19-A

[0552]

[0553] Compound 19-A (40.00 g, 79.26 mmol) was obtained by replacing 9-(4-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol) with 9-(3-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol) and N-phenyl-[1,1':2',1'':2'',1'''-tetraphenyl]-2-amine (33.46 g, 70.64 mmol) with N-phenyl-[1,1':2',1''':2'',1'''-tetraphenyl]-2-amine (28.08 g, 70.64 mmol) using the same method as in step 1 of Synthetic Example 1 above. (MS[M+H) + =726)

[0554] Step 2) Synthesis of Compound 19

[0555]

[0556] Compound 19-A (20.0 g, 27.55 mmol) obtained in step 1 of synthesis example 1 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 1. Otherwise, compound 19 (16.0 g, yield 78.69%) was obtained by the same method as in step 2 of synthesis example 1. (MS[M+H]) + =738)

[0557] Synthesis Example 20. Synthesis of Compound 20

[0558]

[0559] Compound 1-A (20.0 g, 27.55 mmol) obtained in step 1 of Synthesis Example 1 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthesis Example 1. Otherwise, compound 20 (16.0 g, yield 77.84%) was obtained by the same method as in Synthesis Example 2. (MS[M+H]) + =746)

[0560] Synthesis Example 21. Synthesis of Compound 21

[0561] Step 1) Synthesis of compound 21-A

[0562]

[0563] Compound 21-A (31.0 g, 77.91 mmol) was obtained by substituting 9-(4-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol) with 9-(4-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol), except that it was obtained by the same method as in step 1 of Synthetic Example 1 above. (MS[M+H)) + =726)

[0564] Step 2) Synthesis of Compound 21

[0565]

[0566] Compound 21-A (20.0 g, 27.55 mmol) obtained in step 1 of synthesis example 21 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 1. Otherwise, compound 21 (16.0 g, yield 78.69%) was obtained by the same method as in step 2 of synthesis example 1. (MS[M+H]) + =738)

[0567] Synthesis Example 22. Synthesis of Compound 22

[0568]

[0569] Compound 21-A (20.0 g, 27.55 mmol) obtained in step 1 of Synthesis Example 21 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of Synthesis Example 1. Otherwise, compound 22 (16.0 g, 77.84% yield) was obtained by the same method as in Synthesis Example 2. (MS[M+H]) + =746)

[0570] Synthesis Example 23. Synthesis of Compound 23

[0571] Step 1) Synthesis of compound 23-A

[0572]

[0573] Compound 23-A (31.0 g, 77.91 mmol) was obtained by substituting 9-(4-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol) with 9-(4-chlorophenyl)phenanthrene (20.00 g, 69.26 mmol), except that it was obtained by the same method as in step 1 of Synthetic Example 1 above. (MS[M+H)) + =726)

[0574] Step 2) Synthesis of Compound 23

[0575]

[0576] Compound 23-A (20.0 g, 27.55 mmol) obtained in step 1 of synthesis example 23 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 1. Otherwise, compound 23 (16.0 g, yield 78.69%) was obtained by the same method as in step 2 of synthesis example 1. (MS[M+H]) + =738)

[0577] Synthesis Example 24. Synthesis of Compound 24

[0578]

[0579] Compound 23-A (20.0 g, 27.55 mmol) obtained in step 1 of synthesis example 23 was used instead of compound 1-A (20.0 g, 30.78 mmol) obtained in step 1 of synthesis example 1. Otherwise, compound 24 (16.0 g, 77.84% yield) was obtained by the same method as in synthesis example 2. (MS[M+H]) + =746)

[0580] <Experimental Examples and Comparative Experimental Examples>

[0581] Experimental Example 1-1

[0582] A glass substrate coated with an ITO (Indium Tin Oxide) film at a thickness of 1400 Å was immersed in distilled water containing detergent and ultrasonically washed. 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 ultrasonic washing was repeated twice with distilled water for 10 minutes each time. 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.

[0583] On the prepared ITO transparent electrode, a hole injection layer is formed by thermal vacuum evaporation of a compound represented by the chemical formula HAT to a thickness of 100 Å. On the hole injection layer, as a hole transport layer, a compound represented by the chemical formula HT1 is vacuum-evaporated to a thickness of 1150 Å. As an electron blocking layer, compound 1 prepared in Synthesis Example 1 is thermally vacuum-evaporated to a thickness of 150 Å. Next, as a light-emitting layer, a compound represented by the chemical formula BH and a compound represented by the chemical formula BD are vacuum-evaporated at a weight ratio of 25:1 to a thickness of 200 Å. Next, as a hole blocking layer, a compound represented by the chemical formula HB1 is vacuum-evaporated to a thickness of 50 Å. Finally, an electron transport and injection layer is formed by thermal vacuum evaporation of a compound represented by the chemical formula ET1 and a compound represented by the chemical formula LIQ at a weight ratio of 1:1 to a thickness of 310 Å. On the aforementioned electron injection and transport layer, lithium fluoride (LiF) was sequentially deposited with a thickness of 12 Å and aluminum with a thickness of 1000 Å to form a cathode, thereby fabricating an organic light-emitting device.

[0584]

[0585] Experimental Examples 1-2 to 1-24 and Comparative Experimental Examples 1-1 to 1-3

[0586] In Experiment 1-1 above, compounds listed in Table 1 below were used instead of compound 1. Otherwise, organic light-emitting devices of Experiment 1-2 to 1-24 and Comparative Experiment 1-1 to 1-3 were fabricated using the same method as in Experiment 1-1 above. Compounds EB1 to EB3 used in the comparative experiments are shown below.

[0587]

[0588] An application of 10 mA / cm² was applied to the organic light-emitting devices fabricated in the experimental and comparative experimental examples. 2 When 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 luminance to decrease from the initial luminance (6000 nits) to 95%.

[0589]

[0590] As shown in Table 1 above, the organic light-emitting devices of Experimental Examples 1-1 to 1-24, which use the compound of Chemical Formula 1 of this application to form an electron blocking layer, exhibit superior voltage, efficiency, and / or lifetime characteristics compared to the organic light-emitting devices of Comparative Examples 1-1 to 1-3.

[0591] More specifically, the compound of chemical formula 1 of this application has increased structural stability due to the substitution of deuterium. The terminal benzene ring of the tetraphenyl group is connected to the N atom, thereby regulating the hole migration characteristics of the compound. Since the HOMO energy level is low, the energy barrier between the light-emitting layer and the light-emitting layer is reduced. Therefore, the potential barrier between the light-emitting layer and the hole transport field can be appropriately adjusted, thereby improving the hole injection, hole transport and / or electron blocking characteristics of the organic light-emitting device. Therefore, the organic light-emitting devices of Experimental Examples 1-1 to 1-24 have excellent voltage, efficiency and / or lifetime characteristics.

[0592] Conversely, in Comparative Example 1-1, the organic light-emitting device used compound EB1 to form the electron blocking layer. Compound EB1 differs from the compound of Formula 1 of this application in that it does not contain deuterium. It was confirmed that the organic light-emitting device of Comparative Example 1-1 exhibited decreased voltage, efficiency, and / or lifetime characteristics compared to the organic light-emitting devices of Examples 1-1 to 1-24. In particular, it was confirmed that when compared to the organic light-emitting devices of Examples 1-23 and 1-24, which used compounds 23 and 24 with identical structures except for the presence or absence of deuterium to form the electron blocking layer, the lifetime was reduced by a maximum of approximately 39%.

[0593] Comparative Experimental Examples 1-2 used compound EB2 to form the electron blocking layer in the organic light-emitting devices. Compound EB2 differs from the compound of Chemical Formula 1 of this application in that it does not contain deuterium. It was confirmed that the voltage, efficiency, and / or lifetime characteristics of the organic light-emitting devices in Comparative Experimental Examples 1-2 were decreased compared to those in Experimental Examples 1-1 to 1-24. In particular, it was confirmed that when compared to the organic light-emitting devices in Experimental Examples 1-3 and 1-4, which used compounds 3 and 4 with the same structure except for the presence or absence of deuterium to form the electron blocking layer, the lifetime was reduced by a maximum of approximately 35%.

[0594] The organic light-emitting devices of Comparative Examples 1-3 use compound EB3 to form an electron blocking layer. This compound EB3 is different from the compound of Chemical Formula 1 of this application. The intermediate benzene ring of the tetraphenyl group is connected to the N atom. It can be confirmed that the organic light-emitting devices of Comparative Examples 1-3 have higher driving voltage, lower efficiency and shorter lifespan compared with the organic light-emitting devices of Examples 1-1 to 1-24.

[0595] Experimental Examples 2-1 to 2-24 and Comparative Experimental Examples 2-1 and 2-2

[0596] In Experiment 1-1 above, the electron blocking layer was formed by replacing compound 1 with the compound represented by the above chemical formula EB1, and the hole transport layer was formed by replacing the compound represented by the above chemical formula HT1 with the compound listed in Table 2 below. Otherwise, organic light-emitting devices of Experiment 2-1 to 2-24 and Comparative Experiment 2-1 to 2-2 were fabricated by the same method as in Experiment 1-1 above. The compounds HT2 to HT3 used in the comparative experimental examples are shown below.

[0597]

[0598] An application of 10 mA / cm² was applied to the organic light-emitting devices fabricated in the experimental and comparative experimental examples. 2 When the current was applied, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 2 below. On the other hand, T95 refers to the time (hr) required for the brightness to decrease from the initial brightness (6000 nits) to 95%.

[0599]

[0600] As shown in Table 2 above, the organic light-emitting devices of Experimental Examples 2-1 to 2-24, which use the compound of Chemical Formula 1 of this application to form the hole transport layer, exhibit superior voltage, efficiency, and / or lifetime characteristics compared to the organic light-emitting devices of Comparative Examples 1-1 and 2-1 and 2-2.

[0601] In contrast, the organic light-emitting device of Comparative Example 1-1 uses HT1, a compound not included in the scope of Chemical Formula 1 of this application, to form the hole transport layer. It can be confirmed that the voltage, efficiency, and / or lifetime characteristics are reduced compared to the organic light-emitting devices of Examples 2-1 to 2-24.

[0602] Comparative Example 2-1's organic light-emitting device used compound HT2 to form the hole transport layer. This compound HT2 differs from the compound of Formula 1 in that it does not contain deuterium. It was confirmed that the organic light-emitting device of Comparative Example 2-1 exhibited decreased voltage, efficiency, and / or lifetime characteristics compared to the organic light-emitting devices of Examples 2-1 to 2-24. In particular, it was confirmed that when compared to the organic light-emitting devices of Examples 2-23 and 2-24, which used compounds 23 and 24 with identical structures except for the presence or absence of deuterium to form the hole transport layer, the lifetime was reduced by a maximum of approximately 35%.

[0603] The organic light-emitting device of Comparative Example 2-2 uses compound HT3 to form a hole transport layer. This compound HT3 is different from the compound of Chemical Formula 1 of this application. The intermediate benzene ring of the tetraphenyl group is connected to the N atom. It can be confirmed that the organic light-emitting device of Comparative Example 2-2 has a higher driving voltage, lower efficiency and shorter lifetime compared with the organic light-emitting devices of Examples 2-1 to 2-24.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, L1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. L2 is a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Ar can be a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a fused ring group consisting of a substituted or unsubstituted aromatic ring and an aliphatic ring. R1 to R6 may be the same as or different from each other, and each may independently be a hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may be combined with adjacent groups to form a substituted or unsubstituted ring. R7 can be hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. a, b, and d may be the same or different from each other, and each is an independent integer from 0 to 5. c, e, and f may be the same or different from each other, and each is an independent integer from 0 to 4. p and q may be the same or different from each other, and each is an independent integer from 0 to 3. When a, b, c, d, e, f, p, and q are each more than 2, the groups within the parentheses may be the same or different from each other. However, the compound represented by the chemical formula 1 contains more than one deuterium.

2. The compound according to claim 1, wherein, The chemical formula 1 is any one of the following chemical formulas 1-1 to 1-6: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] [Chemical Formulas 1-5] [Chemical Formulas 1-6] In the chemical formulas 1-1 to 1-6, L2, Ar, R1 to R7, a, b, c, d, e, f, and q are defined the same as in chemical formula 1. R11 to R19 may be the same as or different from each other, and each is independently a hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group, which combines with adjacent groups to form substituted or unsubstituted rings. r11 to r19 may be the same as or different from each other, and each is an independent integer from 0 to 4. When r11 to r19 are each more than 2, the groups within the parentheses may be the same or different from each other.

3. The compound according to claim 1, wherein, The L1 is a deuterated or unsubstituted p-phenylene, a deuterated or unsubstituted meta-phenylene, a deuterated or unsubstituted o-phenylene, a deuterated or unsubstituted (p-phenylene)-(p-phenylene)yl, a deuterated or unsubstituted (p-phenylene)-(m-phenylene)yl, or a deuterated or unsubstituted (p-phenylene)-(o-phenylene)yl.

4. The compound according to claim 1, wherein, The L2 is a directly bonded, deuterated or unsubstituted p-phenylene, a deuterated or unsubstituted meta-phenylene, or a deuterated or unsubstituted oro-phenylene.

5. The compound according to claim 1, wherein, The Ar is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, or a deuterated or unsubstituted naphthyl group.

6. The compound according to claim 1, wherein, The deuterium substitution rate of the compound represented by the chemical formula 1 is 20% to 80%.

7. The compound according to claim 1, wherein, The chemical formula 1 is any one of the following compounds: In the compound, n is an integer greater than or equal to 1.

8. An organic light-emitting device, wherein, include: A first electrode, a second electrode disposed opposite to the first electrode, and an organic layer of one or more layers disposed between the first electrode and the second electrode. One or more of the organic layers comprise the compound described in any one of claims 1 to 7.

9. The organic light-emitting device according to claim 8, wherein, The organic layer includes one or more of the following: a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer. One or more of the hole injection layer, hole transport layer, hole injection and transport layer, and electron blocking layer contain the compound of chemical formula 1.

10. The organic light-emitting device according to claim 8, wherein, The organic layer includes a light-emitting layer, which contains a compound represented by the following chemical formula 2: [Chemical Formula 2] In the chemical formula 2, 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 heteroaryl group. Ar20 and Ar21 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. 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 heteroaryl 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.

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