Compounds and organic light emitting devices comprising the same

Abstract

The present specification relates to compounds of Chemical Formula 1 and organic light emitting devices comprising the same.

Description

Technical Field

[0001] This application claims priority to Korean Patent Application No. 10-2024-0175522, filed with the Korean Patent Office on November 29, 2024, 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 blocking layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed. When these excitons re-enter the ground state, they emit light. Such OLEDs are known to possess characteristics such as self-emission, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

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

[0006] Technical issues

[0007] This specification describes compounds 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] A, A', X, and X' may be the same as or different from each other, and each may independently be hydrogen or deuterium.

[0014] L represents a directly bonded, substituted, or unsubstituted aryl group.

[0015] Ar is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, or a fused ring of substituted or unsubstituted aromatic and aliphatic rings.

[0016] R1 and R2 may be the same as or different from each other, and each may independently be hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.

[0017] R3 and R4 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted silyl group, or substituted or unsubstituted aryl group.

[0018] R5 and R6 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, or substituted or unsubstituted silyl group.

[0019] R7 is hydrogen, deuterium, a halogen group, a cyano group, or a substituted or unsubstituted silyl group, or it may be combined with an adjacent group to form a substituted or unsubstituted ring.

[0020] R8 can be hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or can be combined with an adjacent group to form a substituted or unsubstituted ring.

[0021] When a, b, d, e, and f are integers from 0 to 4, and a, b, d, e, and f are 2 or more, the groups within the parentheses may be the same or different from each other.

[0022] c and h are integers from 0 to 2. When c and h are 2, the groups within the parentheses may be the same or different from each other.

[0023] When g is an integer from 0 to 5, and g is 2 or higher, two or more R7s are either the same or different from each other.

[0024] p is an integer from 0 to 3. When p is 2 or more, two or more Ls are the same or different from each other.

[0025] In addition, another 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.

[0026] Invention Effects

[0027] 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 transport, or electron blocking. Attached Figure Description

[0028] 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.

[0029] 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.

[0030] [Symbol Explanation]

[0031] 1: Substrate

[0032] 2: First electrode

[0033] 3: Organic layer

[0034] 4: Second electrode

[0035] 5: Hole injection layer

[0036] 6: Hole transport layer

[0037] 7: Electron blocking layer

[0038] 8: Emissive layer

[0039] 9: Hole-blocking layer

[0040] 10: Electron transport and injection layer Detailed Implementation

[0041] The following is a more detailed description of this instruction manual.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] In this specification, "containing deuterium," "deuterated," or "deuterated" means that hydrogen at substituted positions in a compound is replaced with deuterium. In this specification, "overdeuterated" means a compound or group in which all hydrogen atoms in the molecule are replaced with deuterium, and has the same meaning as "100% deuterated."

[0046] 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 with 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) of the compound or group. 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.

[0047] In this specification, "degree of deuteration" or "deuteration substitution rate" can be determined by nuclear magnetic resonance spectroscopy (NMR spectroscopy). 1 The results were confirmed using known methods such as ¹H NMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry).

[0048] Specifically, through nuclear magnetic resonance spectroscopy (NMR spectroscopy) 1When 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.

[0049] 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.

[0050] In this specification, [ ] Dn The brackets indicate that the structure contains n deuterium atoms. That is, n represents the number of deuterium atoms substituted in the compound within the brackets, 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 brackets. For example, if the compound within the brackets has 46 substituted hydrogen atoms, then n is an integer from 1 to 46.

[0051] In this specification, D can represent deuterium.

[0052] 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.

[0053] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen groups, cyano (-CN), substituted or unsubstituted silyl groups, boron groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups, or substituted by two or more substituents linked together as exemplified above, or without any substituents.

[0054] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, alkyl groups having 1 to 10 carbon atoms, and aryl groups having 6 to 20 carbon atoms, or substituted by two or more substituents linked together as exemplified above, or having no substituents.

[0055] 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 a sequential connection of (substituent 1)-(substituent 2)-(substituent 3), but also the connection of (substituent 2) and (substituent 3) to (substituent 1). For example, phenyl, naphthyl, and isopropyl can be linked to form... , or Such substituents. The above definition also applies to connections of four or more substituents.

[0056] Examples of the substituents mentioned above are given below, but are not limited thereto.

[0057] Examples of halogen groups in this specification include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0058] In this specification, silane can be represented by the chemical formula -SiY1Y2Y3, where Y1, Y2, and Y3 can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the aforementioned silane include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc., but are not limited to these.

[0059] In this specification, the alkyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited to these.

[0060] 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.

[0061] 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. Regarding the aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but is not limited to these. As a polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, peryl, triphenylene, phenylene, fluorene, etc., but is not limited to these.

[0062] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure.

[0063] When the aforementioned fluorene group is replaced, it can become , Isospirofluorene group; (9,9-dimethylfluorenyl) and Substituted fluorenyl groups such as (9,9-diphenylfluorenyl). However, it is not limited to this.

[0064] In this specification, a heteroaryl group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heteroaryl group has 2 to 30 carbon atoms. According to another embodiment, the heteroaryl group has 2 to 20 carbon atoms. The heteroaryl group can be monocyclic or polycyclic. Examples of heteroaryl groups include pyridyl, pyrrolithyl, pyrimidinyl, pyridazinyl, furanyl, thiopheneyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, etc., but are not limited to these.

[0065] In this specification, arylalkyl groups are replaced by aryl groups; otherwise, the above description of alkyl groups may be referenced.

[0066] In this specification, aryl refers to a divalent aryl group; the description of aryl groups above can be used as an example of aryl groups other than divalent.

[0067] In this specification, heteroaryl refers to a divalent heteroaryl group. In addition to being divalent, the above description of heteroaryl groups can be used.

[0068] In this specification, "ring" refers to a hydrocarbon ring or heterocycle in the context of a substituted or unsubstituted ring formed by the combination of adjacent groups with each other.

[0069] The aforementioned hydrocarbon ring can be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a fused ring of aromatic and aliphatic hydrocarbons. In the aforementioned aromatic hydrocarbon rings, the above description of the aryl group can be applied; in the aforementioned aliphatic hydrocarbon rings, the above description of the cycloalkyl group can be applied. Furthermore, the aforementioned structures where aryl and cycloalkyl groups are fused together can be applied to fused aromatic and aliphatic hydrocarbon rings.

[0070] In this specification, the term "forming a ring by bonding with adjacent groups" means forming a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle, or a fused ring thereof by bonding with adjacent groups. The aforementioned hydrocarbon ring refers to a ring composed only of carbon and hydrogen atoms. The aforementioned heterocycle refers to a ring containing one or more atoms selected from N, O, P, S, Si, and Se. In this specification, the aforementioned aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle can be monocyclic or polycyclic.

[0071] 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.

[0072] In this specification, aromatic hydrocarbon rings refer to aromatic rings composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenatene, pyrene, tetraphenylene, phenazine, pentaphenylene, fluorene, indene, acenaphthene, benzo[a]fluorene, spirofluorene, etc., but are not limited to these. In this specification, aromatic hydrocarbon rings can be interpreted in the same way as aryl groups.

[0073] 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.

[0074] In this specification, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, etc. azole, isotonic azole, thiazole, isothiazole, triazole Diazole, thiadiazole, dithiazole, tetraazole, pyran, thiaran, diazine Azine, thiazide, diazine Alkenes, triazines, tetraazines, isoquinoline, quinoline, quinones, quinazoline, quinoxaline, naphthidine, acridine, phenanthridine, diazanaphthalene, triazaindene, indole, indolezine, benzothiazole, benzo[] azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenazine It includes aziridines, indobenzocarbazole, indobenzocarbazole, etc., but is not limited to these.

[0075] 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.

[0076] In this specification, HOMO (highest occupied molecular orbital) refers to the molecular orbital function (HOMO) where the electron is located in the highest energy region of the region where it can participate in bonding. LUMO (lowest unoccupied molecular orbital) refers to the molecular orbital function (LUMO) where the electron is located in the lowest energy region of 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.

[0077] In this specification, bandgap refers to the difference between the HOMO energy level and the LUMO energy level, that is, the HOMO-LUMO bandgap.

[0078] 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).

[0079] In this specification, unless otherwise defined, all technical and scientific terms used have the same meaning as commonly understood by those skilled in the art. Methods and materials similar to or equivalent to those described herein may be used for implementation or testing of 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 a specific passage is mentioned. Furthermore, materials, methods, and embodiments are illustrative and not intended to be limiting.

[0080] 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.

[0081] One embodiment of this specification provides a compound represented by the following chemical formula 1.

[0082] The compounds of chemical formula 1 will now be described in detail.

[0083] [Chemical Formula 1]

[0084]

[0085] In the above chemical formula 1,

[0086] A, A', X, and X' may be the same as or different from each other, and each may independently be hydrogen or deuterium.

[0087] L represents a directly bonded, substituted, or unsubstituted aryl group.

[0088] Ar is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, or a fused ring of substituted or unsubstituted aromatic and aliphatic rings.

[0089] R1 and R2 may be the same as or different from each other, and each may independently be hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.

[0090] R3 and R4 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted silyl group, or substituted or unsubstituted aryl group.

[0091] R5 and R6 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, or substituted or unsubstituted silyl group.

[0092] R7 is hydrogen, deuterium, a halogen group, a cyano group, or a substituted or unsubstituted silyl group, or it may be combined with an adjacent group to form a substituted or unsubstituted ring.

[0093] R8 can be hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or can be combined with an adjacent group to form a substituted or unsubstituted ring.

[0094] When a, b, d, e, and f are integers from 0 to 4, and a, b, d, e, and f are 2 or more, the groups within the parentheses may be the same or different from each other.

[0095] c and h are integers from 0 to 2. When c and h are 2, the groups within the parentheses may be the same or different from each other.

[0096] When g is an integer from 0 to 5, and g is 2 or higher, two or more R7s are either the same or different from each other.

[0097] p is an integer from 0 to 3. When p is 2 or more, two or more Ls are the same or different from each other.

[0098] In one embodiment of this specification, A and A' of the above-mentioned chemical formula 1 are hydrogen or deuterium. The compound represented by the above-mentioned chemical formula 1, by containing (p-phenylene)-(o-phenylene)-carbazole or (p-phenylene)-(p-phenylene)-carbazole, modulates the hole migration characteristics. By appropriately adjusting the hole and electron balance of the organic light-emitting device, a device exhibiting excellent driving voltage, efficiency and lifetime characteristics can be provided.

[0099] In addition, in one embodiment of this specification, the compound represented by the above chemical formula 1 contains terphenyl groups connected only in the ortho direction, thereby having a lower energy level than compounds containing terphenyl groups connected in the para or meta direction, and thus having the effect of improving the hole injection characteristics of organic light-emitting devices.

[0100] Furthermore, in one embodiment of this specification, X and X' of the aforementioned Formula 1 are hydrogen or deuterium. That is, the compound represented by Formula 1 has a substituted or unsubstituted -L-Ar group, with a fused or unfused meta- or para-phenylene group acting as a linking group bonded to the central nitrogen atom. Even with fused phenylene, the carbon atoms at the nitrogen atom and in the meta- or para-position also participate in the fusion. Compared to compounds with -L-Ar group bonded to the central nitrogen atom with an ortho-phenylene group, the compound of Formula 1 in this specification has less steric hindrance, thus facilitating intermolecular stacking and improving hole migration characteristics. Therefore, organic light-emitting devices using the compound of Formula 1 in this specification exhibit excellent driving voltage characteristics.

[0101] In one embodiment of this specification, the above-mentioned chemical formula 1 can be any one of the following chemical formulas 1-1 and 1-2.

[0102] [Chemical Formula 1-1]

[0103]

[0104] [Chemical Formula 1-2]

[0105]

[0106] In the above chemical formulas 1-1 and 1-2,

[0107] A, A', X, X', L, Ar, R1 to R8, a, b, c, d, e, f, g, h, and p are the same as those defined in Chemical Formula 1 above.

[0108] In one embodiment of this specification, the above-mentioned chemical formula 1 can be any one of the following chemical formulas 1-3 and 1-4.

[0109] [Chemical Formulas 1-3]

[0110]

[0111] [Chemical Formulas 1-4]

[0112]

[0113] In the above chemical formulas 1-3 and 1-4,

[0114] A, A', X, X', L, Ar, R1 to R8, a, b, c, d, e, f, g, h, and p are the same as those defined in Chemical Formula 1 above.

[0115] In one embodiment of this specification, A is hydrogen or deuterium.

[0116] In one embodiment of this specification, A is hydrogen.

[0117] In one embodiment of this specification, A is deuterium.

[0118] In one embodiment of this specification, A' is hydrogen or deuterium.

[0119] In one embodiment of this specification, A' is hydrogen.

[0120] In one embodiment of this specification, A' is deuterium.

[0121] In one embodiment of this specification, X is hydrogen or deuterium.

[0122] In one embodiment of this specification, X is hydrogen.

[0123] In one embodiment of this specification, X is deuterium.

[0124] In one embodiment of this specification, X' is hydrogen or deuterium.

[0125] In one embodiment of this specification, X' is hydrogen.

[0126] In one embodiment of this specification, X' is deuterium.

[0127] In one embodiment of this specification, the L mentioned above can be a directly bonded, substituted, or unsubstituted aryl group with 6 to 60 carbon atoms.

[0128] In one embodiment of this specification, the L mentioned above can be a directly bonded, substituted, or unsubstituted aryl group with 6 to 30 carbon atoms.

[0129] In one embodiment of this specification, the L mentioned above can be a directly bonded, substituted, or unsubstituted aryl group having 6 to 20 carbon atoms.

[0130] In one embodiment of this specification, the L mentioned above can be a arylene group with 6 to 20 carbon atoms that is directly bonded, or substituted with deuterium, or unsubstituted.

[0131] In one embodiment of this specification, L can be a directly bonded, substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene.

[0132] In one embodiment of this specification, L can be a directly bonded, deuterated or unsubstituted phenylene, a deuterated or substituted naphthylene, or a deuterated or unsubstituted biphenylene.

[0133] In one embodiment of this specification, L can be a directly bonded, substituted or unsubstituted o-phenylene, substituted or unsubstituted meta-phenylene, substituted or unsubstituted p-phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene.

[0134] In one embodiment of this specification, L can be a directly bonded, deuterated or unsubstituted o-phenylene, deuterated or unsubstituted meta-phenylene, deuterated or unsubstituted p-phenylene, deuterated or unsubstituted naphthylene, or deuterated or unsubstituted biphenylene.

[0135] In one embodiment of this specification, the L mentioned above can be a directly bonded, substituted, or unsubstituted phenylene oxide.

[0136] In one embodiment of this specification, the L mentioned above can be a directly bonded, deuterated, or unsubstituted phenylene oxide.

[0137] In one embodiment of this specification, L can be a directly bonded, substituted or unsubstituted o-phenylene, substituted or unsubstituted meta-phenylene, or substituted or unsubstituted para-phenylene.

[0138] In one embodiment of this specification, L can be a directly bonded, deuterated or unsubstituted o-phenylene, a deuterated or unsubstituted meta-phenylene, or a deuterated or unsubstituted para-phenylene.

[0139] In one embodiment of this specification, the aforementioned Ar may be hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 60 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 60 carbon atoms, substituted or unsubstituted aryl with 6 to 60 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 60 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 60 carbon atoms, or a fused ring of aromatic and aliphatic rings with 7 to 60 carbon atoms.

[0140] In one embodiment of this specification, the aforementioned Ar may be hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 60 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms, or a fused ring of aromatic and aliphatic rings with 7 to 30 carbon atoms.

[0141] In one embodiment of this specification, the aforementioned Ar may be hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted arylalkyl groups having 7 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 20 carbon atoms, or fused ring groups of aromatic and aliphatic rings having 7 to 20 carbon atoms.

[0142] In one embodiment of this specification, the aforementioned Ar may be hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms that is substituted or unsubstituted with deuterium, a cycloalkyl group having 3 to 20 carbon atoms that is substituted or unsubstituted with deuterium, an aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with one or more groups selected from deuterium and alkyl groups having 1 to 10 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms that is substituted or unsubstituted with deuterium, a heteroaryl group having 2 to 20 carbon atoms that is substituted or unsubstituted with one or more groups selected from deuterium and alkyl groups having 1 to 10 carbon atoms, or a fused ring group of aromatic and aliphatic rings having 7 to 20 carbon atoms that is substituted or unsubstituted with one or more groups selected from deuterium and alkyl groups having 1 to 10 carbon atoms.

[0143] In one embodiment of this specification, the aforementioned Ar may be hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted tetrahydronaphthyl.

[0144] In one embodiment of this specification, the aforementioned Ar may be hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms that is substituted or unsubstituted with deuterium, an adamantyl group that is substituted or unsubstituted with deuterium, a phenyl group that is substituted or unsubstituted with one or more groups selected from deuterium and alkyl groups having 1 to 10 carbon atoms, a biphenyl group that is substituted or unsubstituted with deuterium, a terphenyl group that is substituted or unsubstituted with deuterium, a naphthyl group that is substituted or unsubstituted with deuterium, a phenanthryl group that is substituted or unsubstituted with deuterium, a dibenzofuranyl group that is substituted or unsubstituted with deuterium, a dibenzothiophene group that is substituted or unsubstituted with deuterium, or a tetrahydronaphthyl group that is substituted or unsubstituted with one or more groups selected from deuterium and alkyl groups having 1 to 10 carbon atoms.

[0145] In one embodiment of this specification, the aforementioned Ar can be hydrogen; deuterium; an alkyl group having 1 to 4 carbon atoms that is substituted or unsubstituted with deuterium; a phenyl group that is substituted or unsubstituted with one or more groups selected from deuterium, methyl, and tert-butyl; a biphenyl group that is substituted or unsubstituted with deuterium; a terphenyl group that is substituted or unsubstituted with deuterium; a naphthyl group that is substituted or unsubstituted with deuterium; a phenanthryl group that is substituted or unsubstituted with deuterium; a dibenzofuranyl group that is substituted or unsubstituted with deuterium; a dibenzothiophenyl group that is substituted or unsubstituted with deuterium; or a tetrahydronaphthyl group that is substituted or unsubstituted with one or more groups selected from deuterium and methyl.

[0146] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted silyl group, or substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or can be combined with adjacent groups to form an aromatic hydrocarbon ring having substituted or unsubstituted carbon atoms having 6 to 60 carbon atoms.

[0147] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted silyl group, or substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or can be combined with adjacent groups to form an aromatic hydrocarbon ring having substituted or unsubstituted carbon atoms having 6 to 30 carbon atoms.

[0148] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each may be hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted silyl group, or substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or may combine with adjacent groups to form an aromatic hydrocarbon ring having substituted or unsubstituted 6 to 20 carbon atoms.

[0149] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a silyl group substituted or unsubstituted with one or more groups selected from deuterium, alkyl groups having 1 to 10 carbon atoms, and aryl groups having 6 to 20 carbon atoms; or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or a ring of aromatic hydrocarbons having 6 to 20 carbon atoms substituted or unsubstituted with adjacent groups.

[0150] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently hydrogen, deuterium, or an aryl group with 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium, or can be combined with adjacent groups to form an aromatic hydrocarbon ring with 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

[0151] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each may be hydrogen, deuterium, or a substituted or unsubstituted phenyl group, or may combine with adjacent groups to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted cyclohexene ring.

[0152] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently hydrogen, deuterium, or a phenyl group that is substituted or unsubstituted with deuterium, or a cyclohexene ring that can be formed by combining with adjacent groups to form a benzene ring that is substituted or unsubstituted with deuterium, or a cyclohexene ring that is substituted or unsubstituted with one or more groups selected from deuterium and methyl.

[0153] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each may independently be hydrogen or deuterium.

[0154] In one embodiment of this specification, R3 and R4 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted silyl group, or aryl group with 6 to 60 substituted or unsubstituted carbon atoms.

[0155] In one embodiment of this specification, R3 and R4 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted silyl group, or aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0156] In one embodiment of this specification, R3 and R4 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted silyl group, or substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0157] In one embodiment of this specification, R3 and R4 may be the same as or different from each other, and each may independently be hydrogen; deuterium; a halogen group; a cyano group; a silyl group substituted or unsubstituted with one or more groups selected from deuterium, alkyl groups having 1 to 10 carbon atoms, and aryl groups having 6 to 20 carbon atoms; or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0158] In one embodiment of this specification, R3 and R4 may be the same as or different from each other, and each may independently be hydrogen, deuterium, or an aryl group with 6 to 20 carbon atoms that are substituted or unsubstituted with deuterium.

[0159] In one embodiment of this specification, R3 and R4 may be the same as or different from each other, and each may independently be hydrogen, deuterium, a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, or a deuterated or unsubstituted naphthyl.

[0160] In one embodiment of this specification, R3 and R4 may be the same as or different from each other, and each may independently be hydrogen or deuterium.

[0161] In one embodiment of this specification, R5 and R6 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, or substituted or unsubstituted silyl group.

[0162] In one embodiment of this specification, R5 and R6 may be the same as or different from each other, and each may independently be hydrogen, deuterium, fluorine (-F), chlorine (-Cl), bromine (-Br), iodine (-I), cyano, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl or phenylsilyl.

[0163] In one embodiment of this specification, R5 and R6 may be the same as or different from each other, and each may independently be hydrogen or deuterium.

[0164] In one embodiment of this specification, R7 is hydrogen, deuterium, a halogen group, a cyano group, or a substituted or unsubstituted silyl group, or can be combined with an adjacent group to form a hydrocarbon ring with substituted or unsubstituted carbon atoms of 6 to 60.

[0165] In one embodiment of this specification, R7 is hydrogen, deuterium, a halogen group, a cyano group, or a substituted or unsubstituted silyl group, or can be combined with an adjacent group to form a hydrocarbon ring with substituted or unsubstituted carbon atoms of 6 to 30.

[0166] In one embodiment of this specification, R7 is hydrogen, deuterium, a halogen group, a cyano group, or a substituted or unsubstituted silyl group, or can be combined with an adjacent group to form a hydrocarbon ring with substituted or unsubstituted carbon atoms of 6 to 20.

[0167] In one embodiment of this specification, R7 is hydrogen; deuterium; a halogen group; a cyano group; or a silyl group substituted or unsubstituted with one or more groups selected from deuterium, alkyl groups having 1 to 10 carbon atoms, and aryl groups having 6 to 20 carbon atoms, or a hydrocarbon ring having 6 to 20 carbon atoms that can be formed by combining with adjacent groups and being substituted or unsubstituted with deuterium.

[0168] In one embodiment of this specification, R7 is hydrogen or deuterium, or it can combine with adjacent groups to form a hydrocarbon ring with 6 to 20 carbon atoms, either substituted or unsubstituted with deuterium.

[0169] In one embodiment of this specification, R7 is hydrogen or deuterium, or can be combined with adjacent groups to form a substituted or unsubstituted benzene ring, or a substituted or unsubstituted cyclohexene ring.

[0170] In one embodiment of this specification, R7 is hydrogen or deuterium, or can be combined with adjacent groups to form a benzene ring substituted or unsubstituted with deuterium, or a cyclohexene ring substituted or unsubstituted with one or more groups selected from deuterium and methyl.

[0171] In one embodiment of this specification, R7 is hydrogen or deuterium, or it can combine with adjacent groups to form a benzene ring that is substituted with deuterium or unsubstituted.

[0172] In one embodiment of this specification, R8 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a group that can combine with adjacent groups to form an aromatic hydrocarbon ring having 6 to 60 carbon atoms, an aliphatic hydrocarbon ring having 6 to 60 carbon atoms, or an aromatic heterocycle having 2 to 60 carbon atoms.

[0173] In one embodiment of this specification, R8 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a group that can combine with adjacent groups to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, an aliphatic hydrocarbon ring having 6 to 30 carbon atoms, or an aromatic heterocycle having 2 to 30 carbon atoms.

[0174] In one embodiment of this specification, R8 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, an substituted or unsubstituted aliphatic hydrocarbon ring having 6 to 20 carbon atoms, or an aromatic heterocycle having 2 to 20 carbon atoms, which can be combined with adjacent groups.

[0175] In one embodiment of this specification, R8 is hydrogen; deuterium; a halogen group; a cyano group; a silyl group substituted or unsubstituted with one or more groups selected from deuterium, alkyl groups having 1 to 10 carbon atoms, and aryl groups having 6 to 20 carbon atoms; an alkyl group substituted or unsubstituted with deuterium; or an aryl group substituted or unsubstituted with deuterium, or an aromatic hydrocarbon ring having 6 to 20 carbon atoms substituted or unsubstituted with one or more groups selected from deuterium, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, and their linking groups; an aliphatic hydrocarbon ring having 6 to 20 carbon atoms substituted or unsubstituted with one or more groups selected from deuterium, alkyl groups having 1 to 10 carbon atoms, and their linking groups; or an aromatic heterocycle having 2 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0176] In one embodiment of this specification, R8 is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms that is substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium, or an aromatic hydrocarbon ring having 6 to 20 carbon atoms that can be formed by combining with adjacent groups to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms that is substituted or unsubstituted with one or more groups selected from deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and their linking groups; an aliphatic hydrocarbon ring having 6 to 20 carbon atoms that is substituted or unsubstituted with one or more groups selected from deuterium, an alkyl group having 1 to 10 carbon atoms, and their linking groups; or an aromatic heterocycle having 2 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

[0177] In one embodiment of this specification, R8 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group, or can be combined with adjacent groups to form a substituted or unsubstituted benzene ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted cyclohexene ring, a substituted or unsubstituted benzofuran ring, or a substituted or unsubstituted benzothiophene ring.

[0178] In one embodiment of this specification, R8 is hydrogen, deuterium, an alkyl group having 1 to 4 carbon atoms that is substituted or unsubstituted with deuterium, or a phenyl group that is substituted or unsubstituted with deuterium, or a benzene ring that can be formed by combining with an adjacent group; an indene ring that is substituted or unsubstituted with one or more groups selected from deuterium, methyl, phenyl and their linking groups; a cyclohexene ring that is substituted or unsubstituted with one or more groups selected from deuterium, methyl and their linking groups; a benzofuran ring that is substituted or unsubstituted with deuterium; or a benzothiophene ring that is substituted or unsubstituted with deuterium.

[0179] In one embodiment of this specification, R8 is hydrogen, deuterium, methyl, tert-butyl, or a phenyl group that is substituted or unsubstituted with deuterium, or a benzene ring that can be formed by combining with an adjacent group; an indene ring that is substituted or unsubstituted with one or more groups selected from deuterium, methyl, phenyl and their linking groups; a cyclohexene ring that is substituted or unsubstituted with one or more groups selected from deuterium, methyl and their linking groups; a benzofuran ring that is substituted or unsubstituted with deuterium; or a benzothiophene ring that is substituted or unsubstituted with deuterium.

[0180] In one embodiment of this specification, R8 may be hydrogen or deuterium.

[0181] In one embodiment of this specification, a is an integer from 0 to 4. When a is 2 or more, two or more R1s are the same or different from each other.

[0182] In one embodiment of this specification, a is an integer from 0 to 4.

[0183] In one embodiment of this specification, a is 4.

[0184] In one embodiment of this specification, a is 3.

[0185] In one embodiment of this specification, a is 2.

[0186] In one embodiment of this specification, a is 1.

[0187] In one embodiment of this specification, a is 0.

[0188] In one embodiment of this specification, b is an integer from 0 to 4. When b is 2 or more, two or more R2s are the same or different from each other.

[0189] In one embodiment of this specification, b is an integer from 0 to 4.

[0190] In one embodiment of this specification, b is 4.

[0191] In one embodiment of this specification, b is 3.

[0192] In one embodiment of this specification, b is 2.

[0193] In one embodiment of this specification, b is 1.

[0194] In one embodiment of this specification, b is 0.

[0195] In one embodiment of this specification, c is an integer from 0 to 2. When c is 2, R3 are either the same or different from each other.

[0196] In one embodiment of this specification, c is an integer from 0 to 2.

[0197] In one embodiment of this specification, c is 2.

[0198] In one embodiment of this specification, c is 1.

[0199] In one embodiment of this specification, c is 0.

[0200] In one embodiment of this specification, d is an integer from 0 to 4. When d is 2 or more, two or more R4s are the same or different from each other.

[0201] In one embodiment of this specification, d is an integer from 0 to 4.

[0202] In one embodiment of this specification, d is 4.

[0203] In one embodiment of this specification, d is 3.

[0204] In one embodiment of this specification, d is 2.

[0205] In one embodiment of this specification, d is 1.

[0206] In one embodiment of this specification, d is 0.

[0207] 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.

[0208] In one embodiment of this specification, e is an integer from 0 to 4.

[0209] In one embodiment of this specification, e is 4.

[0210] In one embodiment of this specification, e is 3.

[0211] In one embodiment of this specification, e is 2.

[0212] In one embodiment of this specification, e is 1.

[0213] In one embodiment of this specification, e is 0.

[0214] 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.

[0215] In one embodiment of this specification, f is an integer from 0 to 4.

[0216] In one embodiment of this specification, f is 4.

[0217] In one embodiment of this specification, f is 3.

[0218] In one embodiment of this specification, f is 2.

[0219] In one embodiment of this specification, f is 1.

[0220] In one embodiment of this specification, f is 0.

[0221] In one embodiment of this specification, g is an integer from 0 to 5, and when g is 2 or more, two or more R7s are the same or different from each other.

[0222] In one embodiment of this specification, g is an integer from 0 to 5.

[0223] In one embodiment of this specification, g is an integer from 0 to 4.

[0224] In one embodiment of this specification, g is an integer from 0 to 3.

[0225] In one embodiment of this specification, g is an integer from 0 to 2.

[0226] In one embodiment of this specification, g is 5.

[0227] In one embodiment of this specification, g is 4.

[0228] In one embodiment of this specification, g is 3.

[0229] In one embodiment of this specification, g is 2.

[0230] In one embodiment of this specification, g is 1.

[0231] In one embodiment of this specification, g is 0.

[0232] In one embodiment of this specification, h is an integer from 0 to 2. When h is 2, R8 may be the same or different from each other.

[0233] In one embodiment of this specification, h is an integer from 0 to 2.

[0234] In one embodiment of this specification, h is 2.

[0235] In one embodiment of this specification, h is 1.

[0236] In one embodiment of this specification, h is 0.

[0237] In one embodiment of this specification, p is an integer from 0 to 3. When p is 2 or more, two or more Ls are the same or different from each other.

[0238] In one embodiment of this specification, p is an integer from 0 to 3.

[0239] In one embodiment of this specification, p is 3.

[0240] In one embodiment of this specification, p is 2.

[0241] In one embodiment of this specification, p is 1.

[0242] In one embodiment of this specification, p is 0.

[0243] In one embodiment of this specification, the compound represented by Chemical Formula 1 is substituted with at least 10% deuterium. In one embodiment of this specification, the compound represented by Chemical Formula 1 is substituted with at least 20% deuterium. In one embodiment of this specification, the compound represented by Chemical Formula 1 is substituted with at least 30% deuterium. In one embodiment of this specification, the compound represented by Chemical Formula 1 is substituted with at least 40% deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted with at least 50% deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted with at least 60% deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted with at least 70% deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted with at least 80% deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted with at least 90% deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted with 100% deuterium.

[0244] Specifically, the physicochemical properties of deuterium, such as bond length, are different from those of hydrogen. Compared with the CH bond, the CD bond has a smaller stretching amplitude, so the van der Waals radius of deuterium is smaller than that of hydrogen. Under normal circumstances, the CD bond can be shown to be shorter and stronger than the CH bond.

[0245] Therefore, when hydrogen at the substituted position in the above chemical formula 1 is replaced by deuterium, the energy of the ground state decreases, the bond length between deuterium and carbon becomes shorter, and the molecular hardcore volume shrinks. This reduces the electrical polarizability and weakens the intermolecular interaction, thereby increasing the film volume.

[0246] In addition, this property can create a reduced crystallinity of the thin film, i.e., an amorphous state, which can effectively improve the lifetime and driving characteristics of organic light-emitting devices, and the heat resistance can be further improved compared with existing organic light-emitting devices.

[0247] In one embodiment of this specification, the above-mentioned chemical formula 1 is selected from any of the following compounds.

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256] In the above compounds, n is an integer greater than or equal to 1.

[0257] The compound represented by chemical formula 1 according to one embodiment of this specification can be manufactured with a core structure as described in the manufacturing examples below. Substituents can be combined by methods known in the art, and the type, position, or number of substituents can be varied according to techniques known in the art.

[0258] 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 of the structure described above.

[0259] In addition, one embodiment of this specification provides an organic light-emitting device comprising the aforementioned compounds.

[0260] The following section explains organic light-emitting devices.

[0261] In this specification, the term "layer" is used interchangeably with "film" primarily used in this technical field, referring to a coating covering a target area. The size of the "layer" is not limited; the sizes of individual "layers" can be the same or different. In one embodiment, the size of a "layer" can be equal to the size of the entire device, equivalent to the size of a specific functional area, or as small as a single sub-pixel.

[0262] 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.

[0263] 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.

[0264] In this specification, n-type refers to a substance that can abstract electrons from the matrix material (the material of the organic layer). Known substances can generally be used, but are not limited to these. That is, n-type can be defined as a substance that has the property of providing electrons to the LUMO (lowest unoccupied molecular orbital) energy level of the matrix. Conversely, p-type is a substance that, when a layer is composed solely of p-type material, accepts electrons from the HOMO (highest occupied molecular orbital) energy level of the material located in the adjacent cathode direction and generates holes in the material in the adjacent cathode direction; or, when p-type material is doped into any matrix, accepts electrons from the HOMO of the matrix material and generates an equal amount of holes in the HOMO of the matrix. Therefore, when a layer is formed solely of p-type material, the closer the HOMO energy level of the material in the cathode direction is to the LUMO of the p-type material, the easier it is to abstract electrons from the HOMO of the adjacent layer and generate holes in the HOMO of the adjacent layer. Furthermore, when p-type materials are 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 capture electrons and generate holes in the matrix.

[0265] 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 compounds mentioned above.

[0266] According to one embodiment of this specification, an organic light-emitting device is formed by using a compound of 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.

[0267] 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.

[0268] 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.

[0269] 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.

[0270] In one embodiment of this specification, the organic layer includes a light-emitting layer, which may contain a compound represented by the following chemical formula 2.

[0271] [Chemical Formula 2]

[0272]

[0273] In the above chemical formula 2,

[0274] L20 and L21 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heteroaryl group.

[0275] 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.

[0276] 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.

[0277] 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.

[0278] 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 divalent heteroarylene with 2 to 30 carbon atoms.

[0279] 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, hydrogen-substituted or unsubstituted phenylene, a deuterated or unsubstituted divalent biphenyl, a deuterated or unsubstituted divalent naphthyl, a divalent dibenzofuranyl, or a divalent dibenzothiophene.

[0280] In one embodiment of this specification, L20 and L21 are directly bonded.

[0281] 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.

[0282] In one embodiment of this specification, the Ar20 and Ar21 described above may be the same as or different from each other, and each is independently a monocyclic to tetracyclic aryl group with 6 to 20 carbon atoms, substituted or unsubstituted, or a monocyclic to tetracyclic heteroaryl group with 6 to 20 carbon atoms.

[0283] 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.

[0284] 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.

[0285] In one embodiment of this specification, R201 is hydrogen.

[0286] In one embodiment of this specification, the above-mentioned chemical formula 2 may be represented by the following compounds, but is not limited thereto.

[0287]

[0288] In one embodiment of this specification, the organic layer of the organic light-emitting device 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.

[0289] 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 hole migration characteristics are adjusted so that the hole-electron balance in the organic light-emitting device is suitable, thus exhibiting excellent low voltage, high efficiency, and / or long lifetime characteristics.

[0290] 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.

[0291] 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.

[0292] 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.

[0293] 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.

[0294] 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, an electron blocking layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer.

[0295] In one embodiment of this specification, when the organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed from the same substance or different substances.

[0296] 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.

[0297] 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.

[0298] 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.

[0299] 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.

[0300] 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.

[0301] In one embodiment of this specification, the first electrode is the anode and the second electrode is the cathode.

[0302] In another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0303] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with an anode, one or more organic layers and a cathode sequentially stacked on a substrate (normal type).

[0304] In one embodiment of this specification, the aforementioned organic light-emitting device may be an organic light-emitting device with a reverse structure (inverted type) in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate.

[0305] For example, the organic light-emitting device described above can have a stacked structure as shown below, but is not limited to this.

[0306] (1) Anode / hole transport layer / light-emitting layer / cathode

[0307] (2) Anode / hole injection layer / hole transport layer / light emission layer / cathode

[0308] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0309] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0310] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0311] (6) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / cathode

[0312] (7) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0313] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / cathode

[0314] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0315] (10) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0316] (11) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0317] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emission layer / electron transport layer / cathode

[0318] (13) Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0319] (14) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0320] (15) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0321] (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0322] (17) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0323] (18) Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron injection and transport layer / Cathode

[0324] 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.

[0325] 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.

[0326] Figure 2 An example of an organic light-emitting device is illustrated, wherein 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 chemical formula 1 may be included in one or more of the above-described hole injection layer 5, hole transport layer 6, and electron blocking layer 7.

[0327] For example, an organic light-emitting device according to one embodiment of this specification can be manufactured as follows: An anode is formed by depositing a metal or a conductive metal oxide or alloy thereof onto a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation. Then, an organic layer comprising one or more layers selected from a hole injection layer, a hole transport layer, a hole transport and injection layer, 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 is formed on the anode. Finally, a material suitable for use as a cathode is deposited onto the organic layer. Alternatively, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto a substrate.

[0328] 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.

[0329] The anode described above is the electrode for injecting holes. As the anode material, it is generally preferred to be a material with a high work function in order to enable holes to be smoothly injected into the organic layer. Specific examples of anode materials that can be used in this invention include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0330] 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.

[0331] 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 inject 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.

[0332] 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.

[0333] [Chemical formula HI-1]

[0334]

[0335] In the above chemical formula HI-1,

[0336] At least one of X'1 to X'6 is N, and the rest are CH.

[0337] 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.

[0338] In one embodiment of this specification, X'1 to X'6 are N.

[0339] In one embodiment of this specification, R309 to R314 are cyano groups.

[0340] 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.

[0341]

[0342] 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.

[0343] 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.

[0344] [Chemical formula HT-1]

[0345]

[0346] In the above chemical formula HT-1,

[0347] 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.

[0348] 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.

[0349] 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.

[0350] 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.

[0351] 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.

[0352] 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.

[0353] In one embodiment of this specification, R403 to R406 are phenyl.

[0354] 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.

[0355] 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.

[0356] In one embodiment of this specification, L401 and L403 are phenylene oxides.

[0357] In one embodiment of this specification, L402 is a divalent carbazole group substituted with a naphthyl group.

[0358] In one embodiment of this specification, the above chemical formula HT-1 may be represented by the following compounds, but is not limited thereto.

[0359]

[0360] 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.

[0361] 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 this technical field.

[0362] The aforementioned luminescent layer can emit red, green, or blue light and can be composed of 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 azoles, benzothiazoles and benzimidazoles; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, fluorene, etc., but not limited to these.

[0363] 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.

[0364] When the luminescent layer emits red light, phosphorescent dopants such as PIQIr(acac), PQIr(acac), PQIr(acac), PQIr(tris(1-phenylisoquinoline)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, or fluorescent materials such as spiro-DPVBi, spiro-6P, stilbene (DSB), stilbeneylarylene (DSA), PFO-based polymers, and PPV-based polymers can be used as luminescent dopants, but are not limited to these.

[0365] In one embodiment of this specification, the light-emitting dopant may comprise a compound represented by the following chemical formula D-1, but is not limited thereto.

[0366] [Chemical Formula D-1]

[0367]

[0368] In the above chemical formula D-1,

[0369] 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.

[0370] t5 and t6 are each integers from 1 to 4.

[0371] When t5 is 2 or more, the two or more T5 values ​​are the same or different from each other.

[0372] When t6 is 2 or more, the two or more T6 are the same or different from each other.

[0373] 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.

[0374] 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, an aryl group having 6 to 30 carbon atoms that is substituted with or unsubstituted with a cyano group or a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms.

[0375] 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.

[0376] In one embodiment of this specification, the above chemical formula D-1 may be represented by the following compounds, but is not limited thereto.

[0377]

[0378] 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 under the same conditions as the electron injection layer. Specific materials used to form the hole blocking layer include... Diazole or triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc., but not limited to these.

[0379] In one embodiment of this specification, the hole blocking layer may contain a compound represented by the following chemical formula HB-1, but is not limited thereto.

[0380] [Chemical formula HB-1]

[0381]

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

[0383] At least one of Z1 to Z3 is N, and the rest are CH.

[0384] 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.

[0385] 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.

[0386] 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.

[0387] 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.

[0388] 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.

[0389] 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.

[0390] 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.

[0391]

[0392] 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 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.

[0393] 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 light-emitting layer or material, prevent excitons generated in the light-emitting 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.

[0394] The aforementioned electron-injecting material may include at least one of magnesium and lithium fluoride (LiF), specifically, it may include both magnesium and lithium fluoride (LiF), but is not limited thereto.

[0395] 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.

[0396] 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.

[0397] In one embodiment of this specification, the electron transport and injection layer may contain a compound represented by the following chemical formula ET-1, but is not limited thereto.

[0398] [Chemical formula ET-1]

[0399]

[0400] In the above chemical formula ET-1,

[0401] At least one of Z11 to Z13 is N, and the rest are CH.

[0402] At least one of Z14 to Z16 is N, and the rest are CH.

[0403] L701 is a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0404] 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.

[0405] l701 is an integer from 1 to 4. When l701 is a complex number, l701 can be the same or different from each other.

[0406] In one embodiment of this specification, L701 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0407] In one embodiment of this specification, L701 is a phenylene, a divalent biphenyl, or a divalent naphthyl.

[0408] In one embodiment of this specification, L701 is phenylene or a divalent naphthyl group.

[0409] 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.

[0410] In one embodiment of this specification, Ar701 to Ar704 are phenyl groups.

[0411] 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.

[0412]

[0413] In one embodiment of this specification, the electron transport and injection layer may further comprise a metal coordination compound.

[0414] In one embodiment of this specification, the electron transport and injection layer may further comprise a lithium metal coordination compound.

[0415] In one embodiment of this specification, the electron transport and injection layer may further comprise lithium 8-hydroxyquinoline (LiQ).

[0416] 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.

[0417] 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.

[0418] 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.

[0419] In one embodiment of this specification, a capping layer (CPL) may be deposited on 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.

[0420] 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.

[0421] 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.

[0422] <Synthesis example>

[0423] Synthesis Example 1. Synthesis of Compound 1

[0424]

[0425] Toluene (200 ml) was added to a mixture of 9-(4'-chloro-[1,1'-biphenyl]-4-yl)-9H-carbazole (20.00 g, 56.52 mmol), N-phenyl-[1,1':2',1''-terphenyl]-2-amine (18.53 g, 57.65 mmol), and sodium tert-butoxide (7.60 g, 79.13 mmol), and the mixture was heated and stirred for 10 minutes. Then, bis(tri-tert-butylphosphine)palladium (0.14 g, 0.28 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 give compound 1 (28.0 g, 77.55% yield). (MS [M+H]) + =639)

[0426] Synthesis Example 2. Synthesis of Compound 2

[0427]

[0428] Compound 2 (32.00 g, 79.19% yield) was obtained by using N-([1,1'-biphenyl]-4-yl)-[1,1':2',1''-terphenyl]-2-amine (22.92 g, 57.65 mmol) instead of N-phenyl-[1,1':2',1''-terphenyl]-2-amine (18.53 g, 57.65 mmol), except that it was synthesized by the same method as in Synthetic Example 1 above. (MS[M+H) + =715)

[0429] Synthesis Example 3. Synthesis of Compound 3

[0430]

[0431] Compound 3 (32.00 g, 79.19% yield) was obtained by using N-([1,1'-biphenyl]-3-yl)-[1,1':2',1''-terphenyl]-2-amine (22.92 g, 57.65 mmol) instead of N-phenyl-[1,1':2',1''-terphenyl]-2-amine (18.53 g, 57.65 mmol), except that it was synthesized by the same method as in Synthetic Example 1 above. (MS[M+H) + =715)

[0432] Synthesis Example 4. Synthesis of Compound 4

[0433]

[0434] Compound 4 (30.0 g, 77.05% yield) was obtained by using N-([1,1':2',1''-terphenyl]-2-yl)naphthyl-2-amine (21.42 g, 57.65 mmol) instead of N-phenyl-[1,1':2',1''-terphenyl]-2-amine (18.53 g, 57.65 mmol), except that it was synthesized by the same method as in Example 1 above. (MS[M+H) + =689)

[0435] Synthesis Example 5. Synthesis of Compound 5

[0436]

[0437] Compound 5 (33.50 g, 78.51% yield) was obtained by using N-([1,1':2',1''-terphenyl]-2-yl)-9,9-dimethyl-9H-fluorene-2-amine (25.23 g, 57.65 mmol) instead of N-phenyl-[1,1':2',1''-terphenyl]-2-amine (18.53 g, 57.65 mmol), except that it was synthesized by the same method as in Synthetic Example 1 above. (MS[M+H)+ =755)

[0438] Synthesis Example 6. Synthesis of Compound 6

[0439]

[0440] Compound 6 (32.00 g, 77.67% yield) was obtained by using N-([1,1':2',1''-terphenyl]-2-yl)dibenzo[b,d]furan-2-amine (23.72 g, 57.65 mmol) instead of N-phenyl-[1,1':2',1''-terphenyl]-2-amine (18.53 g, 57.65 mmol), except that the method was the same as that described in Synthetic Example 1 above. (MS[M+H) + =729)

[0441] Synthesis Example 7. Synthesis of Compound 7

[0442]

[0443] Compound 7 (33.00 g, 78.38% yield) was obtained by using N-([1,1':2',1''-terphenyl]-2-yl)dibenzo[b,d]thiophene-2-amine (24.65 g, 57.65 mmol) instead of N-phenyl-[1,1':2',1''-terphenyl]-2-amine (18.53 g, 57.65 mmol), except that the method was the same as that described in Synthetic Example 1 above. (MS[M+H) + =745)

[0444] Synthesis Example 8. Synthesis of Compound 8

[0445]

[0446] Compound 8 (31.00 g, 78.93% yield) was obtained by using N-(4-tert-butyl)phenyl-([1,1':2',1''-terphenyl]-2-amine) (21.76 g, 57.65 mmol) instead of N-phenyl-[1,1':2',1''-terphenyl]-2-amine (18.53 g, 57.65 mmol), except that it was synthesized by the same method as in Example 1 above. (MS[M+H) + =695)

[0447] Synthesis Example 9. Synthesis of Compound 9

[0448]

[0449] Compound 9 (31.00 g, 78.93% yield) was obtained by using N-([1,1':2',1''-terphenyl]-2-yl)-5,6,7,8-tetrahydronaphthyl-2-amine (21.65 g, 57.65 mmol) instead of N-phenyl-[1,1':2',1''-terphenyl]-2-amine (18.53 g, 57.65 mmol), except that it was synthesized by the same method as in Synthetic Example 1 above. (MS[M+H) + =693)

[0450] Synthesis Example 10. Synthesis of Compound 10

[0451]

[0452] Compound 10 (30.50 g, 78.34% yield) was obtained by the same method as in Synthetic Example 1 above, except that 2'-(naphthyl-1-yl)-N-phenyl-[1,1'-biphenyl]-2-amine (21.42 g, 57.65 mmol) was used instead of N-phenyl-[1,1':2',1''-terphenyl]-2-amine (18.53 g, 57.65 mmol). (MS[M+H) + =689)

[0453] Synthesis Example 11. Synthesis of Compound 11

[0454]

[0455] Compound 11 (30.50 g, 78.34% yield) was obtained by the same method as in Synthetic Example 1 above, except that 2'-(naphthyl-2-yl)-N-phenyl-[1,1'-biphenyl]-2-amine (21.42 g, 57.65 mmol) was used instead of N-phenyl-[1,1':2',1''-terphenyl]-2-amine (18.53 g, 57.65 mmol). (MS[M+H) + =689)

[0456] Synthesis Example 12. Synthesis of Compound 12

[0457]

[0458] Compound 12 (32.00 g, 79.19% yield) was obtained by the same method as in Synthetic Example 1 above, except that 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-carbazole (20.00 g, 56.52 mmol) was used instead of 9-(4'-chloro-[1,1'-biphenyl]-4-yl)-[1,1':2',1''-terphenyl]-2-amine (22.92 g, 57.65 mmol) was used instead of N-phenyl-[1,1':2',1''-terphenyl]-2-amine (18.53 g, 57.65 mmol). + =715)

[0459] Synthesis Example 13. Synthesis of Compound 13

[0460]

[0461] Compound 13 (35.00 g, 78.29% yield) was obtained by using N-([1,1':4',1''-terphenyl]-4-yl)-[1,1':2',1''-terphenyl]-2-amine (27.30 g, 57.65 mmol) instead of N-([1,1'-biphenyl]-4-yl)-[1,1':2',1''-terphenyl]-2-amine (22.92 g, 57.65 mmol), except that the method was the same as that described in Synthetic Example 12 above. (MS[M+H) + =791)

[0462] Synthesis Example 14. Synthesis of Compound 14

[0463]

[0464] Compound 14 (34.00 g, 78.64% yield) was obtained by using N-(4-(naphthyl-1-yl)phenyl)-[1,1':2',1''-terphenyl]-2-amine (25.80 g, 57.65 mmol) instead of N-([1,1'-biphenyl]-4-yl)-[1,1':2',1''-terphenyl]-2-amine (22.92 g, 57.65 mmol), except that the method was the same as that described in Synthetic Example 12 above. (MS[M+H) + =765)

[0465] Synthesis Example 15. Synthesis of Compound 15

[0466]

[0467] Compound 15 (36.50 g, 79.24% yield) was obtained by using N-(4-(phenanthrene-9-yl)phenyl)-[1,1':2',1''-terphenyl]-2-amine (28.69 g, 57.65 mmol) instead of N-([1,1'-biphenyl]-4-yl)-[1,1':2',1''-terphenyl]-2-amine (22.92 g, 57.65 mmol), except that it was synthesized by the same method as in Example 12 above. (MS[M+H) + =815)

[0468] Synthesis Example 16. Synthesis of Compound 16

[0469]

[0470] Compound 16 (33.50 g, 78.51% yield) was obtained by using N-([1,1':2',1''-terphenyl]-2-yl)-9,9-dimethyl-9H-fluorene-2-amine (25.23 g, 57.65 mmol) instead of N-([1,1'-biphenyl]-4-yl)-[1,1':2',1''-terphenyl]-2-amine (22.92 g, 57.65 mmol), except that the method was the same as that described in Synthetic Example 12 above. (MS[M+H) + =755)

[0471] Synthesis Example 17. Synthesis of Compound 17

[0472]

[0473] Compound 17 (39.00 g, 78.49% yield) was obtained by using N-([1,1':2',1''-terphenyl]-2-yl)-9,9-diphenyl-9H-fluorene-2-amine (32.38 g, 57.65 mmol) instead of N-([1,1'-biphenyl]-4-yl)-[1,1':2',1''-terphenyl]-2-amine (22.92 g, 57.65 mmol), except that the method was the same as that described in Synthetic Example 12 above. (MS[M+H) + =879)

[0474] Synthesis Example 18. Synthesis of Compound 18

[0475]

[0476] Compound 18 (32.00 g, 77.67% yield) was obtained by using N-([1,1':2',1''-terphenyl]-2-yl)dibenzo[b,d]furan-2-amine (23.72 g, 57.65 mmol) instead of N-([1,1'-biphenyl]-4-yl)-[1,1':2',1''-terphenyl]-2-amine (22.92 g, 57.65 mmol), except that the method was the same as that described in Synthetic Example 12 above. (MS[M+H) + =729)

[0477] Synthesis Example 19. Synthesis of Compound 19

[0478]

[0479] Compound 19 (33.00 g, 78.38% yield) was obtained by using N-([1,1':2',1''-terphenyl]-2-yl)dibenzo[b,d]thiophene-2-amine (24.65 g, 57.65 mmol) instead of N-([1,1'-biphenyl]-4-yl)-[1,1':2',1''-terphenyl]-2-amine (22.92 g, 57.65 mmol), except that the method was the same as that described in Synthetic Example 12 above. (MS[M+H) + =745)

[0480] Synthesis Example 20. Synthesis of Compound 20

[0481]

[0482] Compound 20 (33.00 g, 77.95 mmol) was obtained by using N-([1,1':2',1''-terphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-amine (24.88 g, 57.65 mmol) instead of N-([1,1'-biphenyl]-4-yl)-[1,1':2',1''-terphenyl]-2-amine (22.92 g, 57.65 mmol), except that the method was the same as that described in Synthetic Example 12 above. (MS[M+H) + =749)

[0483] Synthesis Example 21. Synthesis of Compound 21

[0484]

[0485] Compound 21 (34.00 g, 78.64% yield) was obtained by using N-([1,1'-biphenyl]-4-yl)-2'-(naphth-1-yl)-[1,1'-biphenyl]-2-amine (25.80 g, 57.65 mmol) instead of N-([1,1'-biphenyl]-4-yl)-[1,1':2',1''-terphenyl]-2-amine (22.92 g, 57.65 mmol), except that the method was the same as that described in Synthetic Example 12 above. (MS[M+H) + =765)

[0486] Synthesis Example 22. Synthesis of Compound 22

[0487]

[0488] Compound 22 (34.00 g, 78.64% yield) was obtained by using N-([1,1'-biphenyl]-4-yl)-2'-(naphthyl-2-yl)-[1,1'-biphenyl]-2-amine (25.80 g, 57.65 mmol) instead of N-([1,1'-biphenyl]-4-yl)-[1,1':2',1''-terphenyl]-2-amine (22.92 g, 57.65 mmol), except that the method was the same as that described in Synthetic Example 12 above. (MS[M+H) + =765)

[0489] Synthesis Example 23. Synthesis of Compound 23

[0490]

[0491] Compound 1 (20.0 g, 31.31 mmol) obtained in Synthetic Example 1 was added to benzene-d6 (200 ml) and completely dissolved. Trifluoromethanesulfonic acid (1.5 ml, 15.66 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 23 (16.0 g, 77.91%). (MS [M+H]) + =656)

[0492] Synthesis Example 24. Synthesis of Compound 24

[0493]

[0494] Compound 24 (16.00 g, 77.90% yield) was obtained by replacing compound 1 (20.0 g, 31.31 mmol) obtained in synthesis example 1 with compound 2 (20.0 g, 27.98 mmol) obtained in synthesis example 23, except that compound 24 was obtained by the same method as in synthesis example 23. (MS[M+H]) + =734)

[0495] Synthesis Example 25. Synthesis of Compound 25

[0496]

[0497] Compound 13 (20.0 g, 25.28 mmol) obtained in Synthesis Example 1 was used instead of compound 1 (20.0 g, 31.31 mmol) obtained in Synthesis Example 1. Otherwise, compound 25 (16.00 g, 77.93% yield) was obtained by the same method as in Synthesis Example 23. (MS[M+H]) + =812)

[0498] Synthesis Example 26. Synthesis of Compound 26

[0499]

[0500] Compound 14 (20.0 g, 26.14 mmol) obtained in Synthesis Example 1 was used instead of compound 1 (20.0 g, 31.31 mmol) obtained in Synthesis Example 1. Otherwise, compound 26 (16.00 g, 77.96% yield) was obtained by the same method as in Synthesis Example 23. (MS[M+H]) + =785)

[0501] <Experimental Examples and Comparative Experimental Examples>

[0502] Experimental Example 1-1

[0503] 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.

[0504] 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. Then, 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, a compound represented by the chemical formula ET1 and a compound represented by the chemical formula LiQ are thermally vacuum-evaporated at a weight ratio of 1:1 to a thickness of 310 Å, thereby forming an electron transport and injection layer. On the aforementioned electron transport and injection layer, lithium fluoride (LiF) is deposited sequentially with a thickness of 12 Å and aluminum with a thickness of 1000 Å to form a cathode, thereby manufacturing an organic light-emitting device.

[0505]

[0506] Experimental Examples 1-2 to 1-26 and Comparative Experimental Examples 1-1 to 1-4

[0507] Organic light-emitting devices of Experimental Examples 1-2 to 1-26 and Comparative Examples 1-1 to 1-4 were fabricated using the same method as in Experimental Examples 1-1, except that the compounds listed in Table 1 below were used instead of compound 1 in Experimental Example 1-1. The compounds EB1 to EB4 used in the comparative examples are shown below.

[0508]

[0509] 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 represents the time (hr) required for the brightness to decrease from the initial brightness (6000 nits) to 95%.

[0510]

[0511] As shown in Table 1 above, the organic light-emitting devices of Experimental Examples 1-1 to 1-26, 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 1-4.

[0512] More specifically, the compounds of Formula 1 of this application contain (p-phenylene)-(o-phenylene)-carbazole or (p-phenylene)-(p-phenylene)-carbazole, thus regulating hole migration characteristics and thereby appropriately adjusting the hole and electron balance of organic light-emitting devices. They contain terphenyl groups linked only at the ortho position, resulting in a low HOMO energy level and improving hole injection characteristics of organic light-emitting devices. They are substituted or unsubstituted with -L-Ar, and fused or unfused meta- or para-phenylene groups are bonded to the central nitrogen atom as linking groups, or the aforementioned phenylene groups are fused with the nitrogen atom at the meta- or para-position, facilitating intermolecular stacking and improving hole migration characteristics. Therefore, the organic light-emitting devices of Experimental Examples 1-1 to 1-26 exhibit excellent voltage, efficiency, and / or lifetime characteristics.

[0513] In contrast, the organic light-emitting device of Comparative Example 1-1 uses a compound EB1, which is different from the compound of Chemical Formula 1 of this application and contains (p-phenylene)-(m-phenylene)-carbazole, to form an electron blocking layer. It can be confirmed that compared with the organic light-emitting devices of Examples 1-1 to 1-26, the driving voltage is high, the efficiency is low, and the lifetime is short.

[0514] Comparing the organic light-emitting devices of Experimental Examples 1-2, the organic light-emitting devices of Experimental Examples 1-2 use compound EB2, which is different from the compound of Chemical Formula 1 of this application, and whose -L-Ar is linked to the central nitrogen atom through an ortho-phenylene group, to form an electron blocking layer. It can be confirmed that compared with the organic light-emitting devices of Experimental Examples 1-1 to 1-26, the driving voltage is high, the efficiency is low, and the lifetime is short.

[0515] Comparing the organic light-emitting devices of Experimental Examples 1-3, the organic light-emitting devices used compounds that are different from those of Chemical Formula 1 of this application, where X or X' of Chemical Formula 1 is not hydrogen or deuterium, i.e., compounds EB3 containing dibenzofuran as a substituent of amines formed by fusion of carbons at the nitrogen atom position and the ortho-direction, can be used to form an electron blocking layer. It can be confirmed that compared with the organic light-emitting devices of Experimental Examples 1-1 to 1-26, the driving voltage is high, the efficiency is low, and the lifetime is short.

[0516] Comparing the organic light-emitting devices of Examples 1-4, which use compound EB4 (containing terphenyl groups linked only in the meta or para directions, different from the compound of Formula 1 of this application) to form the electron blocking layer, it can be confirmed that compared with the organic light-emitting devices of Examples 1-1 to 1-26, the driving voltage is high, the efficiency is low, and the lifetime is short. In particular, when compared with the organic light-emitting devices of Examples 1-13, which use compound 13 (with the same structure as the compound except for the linkage direction of the terphenyl groups) to form the electron blocking layer, it can also be confirmed that the driving voltage is high, the efficiency is low, and the lifetime is short.

[0517] Experimental Examples 2-1 to 2-26 and Comparative Experimental Examples 2-1 to 2-3

[0518] In Experiment 1-1 above, an electron blocking layer was formed by replacing compound 1 with a compound represented by the above chemical formula EB1, and a hole transport layer was formed by replacing the compound represented by the above chemical formula HT1 with a compound listed in Table 2 below. Otherwise, organic light-emitting devices of Experiment 2-1 to 2-26 and Comparative Experiment 2-1 to 2-3 were fabricated using the same method as in Experiment 1-1. The compounds HT2 to HT4 used in the comparative experiments are shown below.

[0519]

[0520] An application of 10 mA / cm² was applied to the organic light-emitting devices fabricated in the experimental and comparative experimental examples. 2 At the given current, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 2 below. On the other hand, T95 represents the time (hr) required for the brightness to decrease from the initial brightness (6000 nits) to 95%.

[0521]

[0522] As shown in Table 2 above, the organic light-emitting devices of Experimental Examples 2-1 to 2-26, 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 to 2-3.

[0523] Conversely, the organic light-emitting device of Comparative Example 1-1 uses compound HT1, which is not included in the scope of Chemical Formula 1 of this application, to form a hole transport layer. It can be confirmed that compared with the organic light-emitting devices of Examples 2-1 to 2-26, it has a higher driving voltage, lower efficiency, and shorter lifetime.

[0524] Comparing the organic light-emitting device of Experimental Example 2-1, HT2, a compound containing (p-phenylene)-(m-phenylene)-carbazole that is different from the compound of Chemical Formula 1 of this application, was used to form the hole transport layer. It can be confirmed that compared with the organic light-emitting devices of Experimental Examples 2-1 to 2-26, the driving voltage is high, the efficiency is low, and the lifetime is short.

[0525] Comparing the organic light-emitting device of Experimental Example 2-2, a compound HT3, which is different from the compound of Chemical Formula 1 of this application and has -L-Ar bonded to the central nitrogen atom via o-phenylene as a linking group, was used to form the hole transport layer. It can be confirmed that compared with the organic light-emitting devices of Experimental Examples 2-1 to 2-26, the driving voltage is high, the efficiency is low, and the lifetime is short.

[0526] Comparing the organic light-emitting devices of Experimental Examples 2-3, which use compound HT4 (different from the compound of Chemical Formula 1 of this application) containing terphenyl groups connected only in the meta position to form the hole transport layer, it can be confirmed that compared with the organic light-emitting devices of Experimental Examples 2-1 to 2-26, the driving voltage is high, the efficiency is low, and the lifetime is short. In particular, when compared with the organic light-emitting devices of Experimental Example 2-16, which use compound 16 (with the same structure as the compound except for the connection direction of the terphenyl groups) to form the hole transport layer, it can also be confirmed that the driving voltage is high, the efficiency is low, and the lifetime is short.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, A, A', X, and X' may be the same as or different from each other, and each may independently be hydrogen or deuterium. L represents a directly bonded, substituted, or unsubstituted aryl group. Ar is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, or a fused ring of substituted or unsubstituted aromatic and aliphatic rings. R1 and R2 may be the same as or different from each other, and each may independently be hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring. R3 and R4 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted silyl group, or substituted or unsubstituted aryl group. R5 and R6 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, or substituted or unsubstituted silyl group. R7 is hydrogen, deuterium, a halogen group, a cyano group, or a substituted or unsubstituted silyl group, or it may be combined with an adjacent group to form a substituted or unsubstituted ring. R8 can be hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or can be combined with an adjacent group to form a substituted or unsubstituted ring. When a, b, d, e, and f are integers from 0 to 4, and a, b, d, e, and f are 2 or more, the groups within the parentheses may be the same or different from each other. c and h are integers from 0 to 2. When c and h are 2, the groups within the parentheses may be the same or different from each other. When g is an integer from 0 to 5, and g is 2 or higher, two or more R7s are either the same or different from each other. p is an integer from 0 to 3. When p is 2 or more, two or more Ls are the same or different from each other.

2. The compound according to claim 1, wherein, The chemical formula 1 is any one of the following chemical formulas 1-1 and 1-2: [Chemical Formula 1-1] [Chemical Formula 1-2] In the chemical formulas 1-1 and 1-2, A, A', X, X', L, Ar, R1 to R8, a, b, c, d, e, f, g, h, and p are the same as those defined in Chemical Formula 1.

3. The compound according to claim 1, wherein, The chemical formula 1 is any one of the following chemical formulas 1-3 and 1-4: [Chemical Formulas 1-3] [Chemical Formulas 1-4] In the chemical formulas 1-3 and 1-4, A, A', X, X', L, Ar, R1 to R8, a, b, c, d, e, f, g, h, and p are the same as those defined in Chemical Formula 1.

4. The compound according to claim 1, wherein, The L is a directly bonded, deuterated, or unsubstituted phenylene.

5. The compound according to claim 1, wherein, The Ar is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms that is substituted or unsubstituted with deuterium, an adamantyl group that is substituted or unsubstituted with deuterium, a phenyl group that is substituted or unsubstituted with one or more groups selected from deuterium and alkyl groups having 1 to 10 carbon atoms, a biphenyl group that is substituted or unsubstituted with deuterium, a terphenyl group that is substituted or unsubstituted with deuterium, a naphthyl group that is substituted or unsubstituted with deuterium, a phenanthryl group that is substituted or unsubstituted with deuterium, a dibenzofuranyl group that is substituted or unsubstituted with deuterium, a dibenzothiophenyl group that is substituted or unsubstituted with deuterium, or a tetrahydronaphthyl group that is substituted or unsubstituted with one or more groups selected from deuterium and alkyl groups having 1 to 10 carbon atoms.

6. The compound according to claim 1, wherein, The R7 is hydrogen or deuterium, or it may be combined with an adjacent group to form a benzene ring that is substituted or unsubstituted with deuterium, or a cyclohexene ring that is substituted or unsubstituted with one or more groups selected from deuterium and methyl.

7. The compound according to claim 1, wherein, 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, wherein one or more of the organic layers comprises a compound according to 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 transport layer, a hole injection layer, a hole injection and transport layer, and an electron blocking layer. One or more of the hole transport layer, hole injection layer, hole injection and transport layer, and electron blocking layer contain a 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 divalent 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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