Compounds and organic light emitting devices comprising the same

Abstract

This specification provides compounds of Formula 1 and organic light-emitting devices containing them. The compounds described herein can be used as materials for the organic layer of organic light-emitting devices. These compounds can improve the efficiency and lifetime characteristics of organic light-emitting devices.

Description

Technical Field

[0001] This application claims priority to Korean Patent Application No. 10-2025-0048084, filed with the Korean Patent Office on April 14, 2025, and Korean Patent Application No. 10-2026-0045455, filed with the Korean Patent Office on March 13, 2026, the entire contents of which are incorporated herein by reference.

[0002] This specification relates to compounds and organic light-emitting devices containing them. Background Technology

[0003] 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 multilayer structure composed of different materials; for example, it can consist of a hole injection layer, a hole transport layer, a light-emitting 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, they form excitons. When these excitons re-enter the ground state, they emit light.

[0004] There is a continuous demand for the development of new materials for organic light-emitting devices as described above.

[0005] Existing technical documents

[0006] Patent documents

[0007] Korean Patent Publication No. 2021-0021421 Summary of the Invention

[0008] Technical issues

[0009] This specification provides compounds and organic light-emitting devices containing them.

[0010] Solution to the problem

[0011] In one embodiment of this specification, a compound of chemical formula 1 is provided.

[0012] [Chemical Formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] R1, R2, R4, R5 and R7 to R11 are deuterium.

[0016] R3 and R6 may be the same as or different from each other, and each may be independently deuterium, or substituted or unsubstituted aryl groups.

[0017] L1 is a directly bonded, substituted, or unsubstituted aryl group.

[0018] The L1 group mentioned above does not contain substituted or unsubstituted divalent anthracene groups.

[0019] l1 can be 1 or 2. When l1 is 2, the above L1 values ​​may be the same or different from each other.

[0020] Ar1 is a substituted or unsubstituted aryl group.

[0021] In addition, one embodiment of this specification provides an organic light-emitting device, which includes: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers contain a compound of the chemical formula 1.

[0022] In addition, one embodiment of this specification provides an organic light-emitting device, comprising: an anode, a cathode, a first light-emitting layer disposed between the anode and the cathode, and a second light-emitting layer disposed between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, wherein the first light-emitting layer comprises a compound of the chemical formula 1, and the second light-emitting layer comprises a compound of the chemical formula H.

[0023] [Chemical formula H]

[0024]

[0025] In the above chemical formula H,

[0026] L20 and L21 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0027] Ar20 and Ar21 may be the same as or different from each other, and each can be independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0028] R301 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0029] r301 is an integer from 1 to 8. When r301 is 2 or more, two or more r301s are the same or different from each other.

[0030] Invention Effects

[0031] The compounds described in this specification can be used as materials for the organic layer of organic light-emitting devices (OLEDs). Conventionally used anthracene compounds utilize triplet-triplet fusion (TTF) as the primary light-emitting mechanism. In OLEDs where anthracene compounds are used as the host of the light-emitting layer, the region where holes and electrons combine (the recombination zone) and the emission zone are identical. If a compound of formula 1 in this specification, having a higher triplet energy than anthracene compounds, is used as the host and combined with a second host having a lower triplet energy, holes and electrons combine to form excitons in this compound. The singlet state directly participates in light emission, and the triplet state undergoes dexter energy transfer to the second host with the lower energy. The anthracene compound receiving the triplet state or another second host emits light in TTF form. Therefore, the efficiency and lifetime characteristics of OLEDs can be improved. Attached Figure Description

[0032] Figure 1 An example is shown of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 6, and a cathode 10 are sequentially stacked. In the structure described above, the aforementioned compound may be included in the light-emitting layer 6.

[0033] Figure 2 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking (hole modulation) layer 5, a light-emitting layer 6, a hole blocking (electron modulation) layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10 stacked in sequence.

[0034] Figure 3 The illustration shows an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection and transport layer 34, a light-emitting layer 6, an electron transport layer 8, an electron injection layer 9, and a cathode 10 are stacked in sequence.

[0035] Figure 4 The illustration shows an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection and transport layer 34, a first light-emitting layer 6-1, a second light-emitting layer 6-2, an electron transport layer 8, an electron injection layer 9, and a cathode 10 are stacked in sequence.

[0036] Figure 5 The illustration shows an example of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking (hole modulation) layer 5, a first light-emitting layer 6-1, a second light-emitting layer 6-2, a first electron transport layer 8-1, a second electron transport layer 8-2, an electron injection layer 9, and a cathode 10.

[0037] Figure 6 This is the MS spectrum of compound A.

[0038] [Symbol Explanation]

[0039] 1: Substrate

[0040] 2: Anode

[0041] 3: Hole injection layer

[0042] 4: Hole transport layer

[0043] 34: Hole Injection and Transport Layer

[0044] 5: Electron blocking (hole modulation) layer

[0045] 6: Emissive layer

[0046] 6-1: First light-emitting layer

[0047] 6-2: Second light-emitting layer

[0048] 7: Hole-blocking (electronic regulation) layer

[0049] 8: Electron transport layer

[0050] 8-1: First Electron Transport Layer

[0051] 8-2: Second Electron Transport Layer

[0052] 9: Electron injection layer

[0053] 10: Cathode Detailed Implementation

[0054] The following is a more detailed description of this instruction manual.

[0055] According to one embodiment of this specification, chemical formula 1 is ∠R1, R2, R4, R5, and R7 to R11 are deuterium, and a substituted or unsubstituted aryl group is bonded at a specific position on the nucleus. The triplet energy level (T) of the substituent bonded to the aforementioned ∠R1 is... s 1) Compounds with a triplet energy level of π or higher. Compared with previously used anthracene compounds, the compounds of the above-mentioned chemical formula 1 have a higher triplet energy. The triplet energy is transferred to the second host used together. Therefore, compared with using the second host (anthracene compound) alone, triplet quenching of the compound is reduced, thereby improving efficiency and lifetime characteristics in organic light-emitting devices.

[0056] According to one embodiment of this specification, R1, R2, R4, R5, and R7 to R11 of the above-mentioned chemical formula 1 are deuterium. The physicochemical properties of deuterium, such as bond length, differ from those of hydrogen. Compared to the CH bond, the CD bond has a smaller stretching amplitude, resulting in a smaller van der Waals radius for deuterium than for hydrogen. Generally, the CD bond is shorter and stronger than the CH bond. Therefore, if the above-mentioned 1 contains deuterium as a substituent, the ground state energy decreases, the deuterium-carbon bond length shortens, and the molecular hardcore volume shrinks. This reduces electrical polarizability and weakens intermolecular interactions, thereby increasing the film volume. Furthermore, this characteristic can reduce the crystallinity of the film, forming an amorphous state, which can effectively improve the lifetime and driving characteristics of organic light-emitting devices, and further enhance heat resistance compared to existing organic light-emitting devices. Furthermore, since the above chemical formula 1 contains deuterium, it can be shown that the driving voltage of the organic light-emitting device is lower than that of the same structure replaced by deuterium, and the lifetime is longer.

[0057] Examples of substituents in this specification are described below, but are not limited thereto.

[0058] In this instruction manual, Indicates the part that is connected.

[0059] Throughout the description of this application, the term "combination of them" in the Markush form means a mixture or combination of one or more of the constituent elements described in the Markush form, or means including one or more of the aforementioned constituent elements.

[0060] The term "substitution" refers to the replacement of hydrogen atoms on carbon atoms in a compound with other substituents. 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 more than two substituents are substituted, the two or more substituents can be the same or different from each other.

[0061] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen groups, cyano, alkyl, cycloalkyl, alkoxy, alkenyl, haloalkyl, silyl, aryl, aromatic hydrocarbon rings and aliphatic hydrocarbon rings, and heteroaryl, or substituted by two or more substituents linked together as exemplified above, or without any substituents.

[0062] In this specification, the connection of two or more substituents means that the hydrogen of any one substituent is replaced by another substituent. For example, the connection of two substituents can be achieved by linking a phenyl group with a naphthyl group. or Such substituents. Furthermore, the connection of three substituents includes not only the case of (substituent 1)-(substituent 2)-(substituent 3) sequentially linked, but also the case where (substituent 2) and (substituent 3) are linked to (substituent 1). For example, phenyl, naphthyl, and isopropyl can be linked to form... , or Such substituents. The above definition also applies to cases where four or more substituents are connected.

[0063] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine groups.

[0064] In this specification, alkyl groups can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, but are not limited to these.

[0065] In this specification, cycloalkyl groups are not particularly limited, but preferably cycloalkyl groups with 3 to 30 carbon atoms. Specifically, they include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc., but are not limited to these.

[0066] In this specification, the alkoxy group can be straight-chain, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 30. Specifically, it includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited to these.

[0067] In this specification, the alkenyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbyl, styryl, etc., but are not limited to these.

[0068] In this specification, alkyl halogroup refers to a hydrogen atom that has at least one halogen group replacing the alkyl group defined above.

[0069] In this specification, the aryl group is not particularly limited, but it is preferably an aryl group with 6 to 30 carbon atoms, and the aryl group can be monocyclic or polycyclic. The aryl group comprises one or more five-membered and six-membered rings, or can be a fused ring of them.

[0070] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferred to have 6 to 30 carbon atoms. Specifically, the monocyclic aryl group can be phenyl, biphenyl, terphenyl, etc., but is not limited to these.

[0071] When the aryl group mentioned above is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferred to have 10 to 30 carbon atoms. Specifically, the polycyclic aryl group can be naphthyl, anthraceneyl, phenanthrene, phenylene, pyrene, finadeninyl, peryl, alkyl, fluorene, spirodifluorene, etc., but is not limited to these.

[0072] In this specification, the fluorene group can be substituted, and adjacent groups can combine with each other to form a ring.

[0073] As an example of the aforementioned fluorene compounds, there are , , , , , , and etc., but not limited to this.

[0074] 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.

[0075] In this specification, the heteroaryl group comprises one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may comprise one or more atoms selected from O, N, Se, and S. The heteroaryl group comprises one or more five-membered and six-membered rings, or may be fused rings thereof. The number of carbon atoms is not particularly limited, but preferably 2 to 30. The heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene, furanyl, pyrrole, imidazolyl, and thiazolyl. azole group, Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazenopyrazinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthridine, phenanthroline, iso Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothiopyrrolyl, phen Thiol (phenoxathiine), phen Phenoxazine, phenothiazine, dihydroindocarbazolyl, spirofluorenylxanthinyl, and spirofluorenylthioxanthinyl are examples, but not limited to these.

[0076] In this specification, silane can be alkylsilane, arylsilane, heteroarylsilane, etc. The alkyl group in the alkylsilane can be any of the examples of the alkyl groups described above; the aryl group in the arylsilane can be any of the examples of the aryl groups described above; and the heteroaryl group in the heteroarylsilane can be any of the examples of the heteroaryl groups described above.

[0077] In this specification, the hydrocarbon ring can be an aromatic hydrocarbon cyclic group, an aliphatic hydrocarbon cyclic group, or a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring. Among the aforementioned aromatic hydrocarbon cyclic groups, the description of aryl groups described above applies; among aliphatic hydrocarbon cyclic groups, the description of cycloalkyl groups described above applies. Furthermore, fused ring groups of aromatic and aliphatic hydrocarbon rings can be structures formed by the fusion of aryl and cycloalkyl groups as described above.

[0078] In this specification, the heterocyclic group can be an aromatic heterocyclic group, an aliphatic heterocyclic group, or a fused ring group of an aromatic heterocyclic group and an aliphatic heterocyclic group. Among the above-mentioned aromatic heterocyclic groups, the above description of heteroaryl groups can be applied.

[0079] In this specification, arylene refers to a group with two bonding sites on an aryl group, i.e., a divalent group. Apart from being divalent groups themselves, they are subject to the above description of aryl groups.

[0080] In this specification, a heteroaryl group refers to a group with two bonding sites on a heteroaryl group, i.e., a divalent group. Apart from being divalent groups themselves, they are subject to the above description of heteroaryl groups.

[0081] In this specification, a five-membered ring refers to a ring that contains a five-membered ring in the above-mentioned hydrocarbon cyclic group, heterocyclic group, or structure formed by their fusion, except that it is not a monovalent group.

[0082] In this specification, the term "six-membered ring" can be applied to the description of substituents containing six-membered rings in the above-described aryl, heteroaryl, cycloalkyl, or combinations thereof, except that they are not monovalent groups.

[0083] In this specification, the aforementioned second subject refers to the subject of the second light-emitting layer or the second subject of the first light-emitting layer.

[0084] In this specification, "above" means equal to or greater than (higher than, or more than) the quantity, value, or range used as a reference; "below" means equal to or less than (lower than, or less than) the quantity, value, or range used as a reference; "exceeding" means greater than (higher than, or more than) the quantity, value, or range used as a reference; and "less than" means less than (lower than, or less than) the quantity, value, or range used as a reference.

[0085] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. Methods and materials similar to or equivalent to those described herein may be used to implement or test embodiments of the invention, but suitable methods and materials are described later. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, this specification, including definitions, takes precedence unless otherwise specified. Furthermore, materials, methods, and embodiments are illustrative only and not intended to be limiting.

[0086] The compounds of the above chemical formula 1 will now be described in detail.

[0087] According to one embodiment of this specification, the above chemical formula 1 is any one of the following chemical formulas 1-1 to 1-3.

[0088] [Chemical Formula 1-1]

[0089]

[0090] [Chemical Formula 1-2]

[0091]

[0092] [Chemical Formulas 1-3]

[0093]

[0094] In the above chemical formulas 1-1 to 1-3,

[0095] The definitions of R1 to R11, L1, and l1 are the same as those in Chemical Formula 1 above.

[0096] R101 and R102 may be the same as or different from each other, and each may be an independently substituted or unsubstituted alkyl group.

[0097] R103 to R110 may be the same as or different from each other, and each is independently hydrogen or deuterium.

[0098] r103 is an integer from 1 to 3. When r103 is 2 or more, the two or more r103 values ​​are either the same or different from each other.

[0099] r104 is an integer from 1 to 4. When r104 is 2 or higher, the two or more r104 values ​​are either the same or different from each other.

[0100] r110 is an integer from 1 to 7. When r110 is 2 or more, the two or more r110 are the same or different from each other.

[0101] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium.

[0102] According to one embodiment of this specification, R1 to R11 are deuterium.

[0103] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium.

[0104] According to one embodiment of this specification, R1, R2 and R4 to R11 are deuterium.

[0105] In one embodiment of this specification, l1 is 1.

[0106] In one embodiment of this specification, l1 is 2.

[0107] In one embodiment of this specification, when l1 is 2, the two L1s refer to being connected in series, that is, -L1-L1-. The two L1s may be the same or different from each other, and the Ar1 of the chemical formula 1 is combined with the terminal L1 through -L1-L1-Ar1.

[0108] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each is independently deuterium, or an aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0109] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each is independently deuterium, or a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0110] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each is independently a deuterium, a polycyclic aryl group comprising a five-membered ring and a six-membered ring with 9 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic aryl group comprising a six-membered ring with 6 to 30 substituted or unsubstituted carbon atoms.

[0111] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each independently is a deuterium, a polycyclic aryl group with 9 to 30 substituted or unsubstituted carbon atoms formed by a five-membered or six-membered ring, or a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms formed by a six-membered ring.

[0112] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each is independently deuterium, or an aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0113] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each is independently deuterium, or a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0114] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each is independently a deuterium, a polycyclic aryl group containing a five-membered or six-membered ring with 9 to 20 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic aryl group containing a six-membered ring with 6 to 20 substituted or unsubstituted carbon atoms.

[0115] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each is independently a deuterium, a polycyclic aryl group with 9 to 20 substituted or unsubstituted carbon atoms formed by a five-membered ring and a six-membered ring, or a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms formed by a six-membered ring.

[0116] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each is independently deuterium, or an aryl group substituted or unsubstituted by deuterium, alkyl, aryl, or a combination thereof.

[0117] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each is independently deuterium, or an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a combination thereof, or an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted.

[0118] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each is independently deuterium; or a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group with 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or a combination thereof.

[0119] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each is independently deuterium; a polycyclic aryl group comprising a five-membered ring and a six-membered ring, substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a combination thereof; or a monocyclic or polycyclic aryl group comprising a six-membered ring, substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0120] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each is independently deuterium; a polycyclic aryl group with 9 to 30 carbon atoms formed by a five-membered ring and a six-membered ring, substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group with 1 to 30 carbon atoms, or a combination thereof; or a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms formed by a six-membered ring, substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or a combination thereof.

[0121] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, each being independently deuterium; or substituted or unsubstituted by deuterium, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a combination thereof, or an aryl group having 6 to 20 carbon atoms.

[0122] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each may be deuterium; or may be a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group with 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms, or a combination thereof.

[0123] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each is independently deuterium; a polycyclic aryl group comprising a five-membered ring and a six-membered ring, substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a combination thereof; or a monocyclic or polycyclic aryl group comprising a six-membered ring, substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0124] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each is independently deuterium; a polycyclic aryl group with 9 to 20 carbon atoms formed by a five-membered ring and a six-membered ring, substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group with 1 to 20 carbon atoms, or a combination thereof; or a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms formed by a six-membered ring, substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms, or a combination thereof.

[0125] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each independently represents: a phenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a naphthyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a phenanthryl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; or a fluorenyl group substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a combination thereof.

[0126] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each independently represents: a phenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; a naphthyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; a phenanthryl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; or a fluorenyl group substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a combination thereof.

[0127] According to one embodiment of this specification, R3 and R6 may be the same as or different from each other, and each is independently deuterium; a phenyl group substituted or unsubstituted with deuterium, phenyl, naphthyl, phenanthryl, or a combination thereof; a naphthyl group substituted or unsubstituted with deuterium, phenyl, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium; a phenanthryl group substituted or unsubstituted with deuterium; or a fluorenyl group substituted or unsubstituted with deuterium, methyl, or a combination thereof.

[0128] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being independently deuterium or an aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0129] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being independently deuterium, or a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0130] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each independently being deuterium, a polycyclic aryl group containing a five-membered ring or a six-membered ring with 9 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic aryl group containing a six-membered ring with 6 to 30 substituted or unsubstituted carbon atoms.

[0131] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each independently being deuterium, a polycyclic aryl group with 9 to 30 substituted or unsubstituted carbon atoms formed by a five-membered ring and a six-membered ring, or a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms formed by a six-membered ring.

[0132] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being independently deuterium or an aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0133] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being independently deuterium, or a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0134] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each independently being deuterium, a polycyclic aryl group containing a five-membered or six-membered ring with 9 to 20 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic aryl group containing a six-membered ring with 6 to 20 substituted or unsubstituted carbon atoms.

[0135] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each independently being deuterium, a polycyclic aryl group with 9 to 20 substituted or unsubstituted carbon atoms formed by a five-membered ring and a six-membered ring, or a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms formed by a six-membered ring.

[0136] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being deuterium independently; or are substituted or unsubstituted aryl groups by deuterium, alkyl, aryl, or combinations thereof.

[0137] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being independently deuterium; or are substituted or unsubstituted by deuterium, alkyl groups having 1 to 30 carbon atoms, aryl groups having 6 to 30 carbon atoms, or combinations thereof, or by aryl groups having 6 to 30 carbon atoms.

[0138] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being deuterium independently; or are substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0139] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being independently deuterium; or a polycyclic aryl group comprising a five-membered ring and a six-membered ring, substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a combination thereof; or a monocyclic or polycyclic aryl group comprising a six-membered ring, substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0140] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being independently deuterium; aryl groups formed of five-membered and six-membered rings with 9 to 30 carbon atoms, substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group with 1 to 30 carbon atoms, or combinations thereof; or aryl groups formed of six-membered rings with 6 to 30 carbon atoms, substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or combinations thereof.

[0141] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being independently deuterium; or are substituted or unsubstituted by deuterium, alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, or combinations thereof, or aryl groups having 6 to 20 carbon atoms.

[0142] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being independently deuterium; or are substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0143] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being independently deuterium; aryl groups comprising five-membered and six-membered rings that are substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a combination thereof; or aryl groups comprising six-membered rings that are substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0144] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being independently deuterium; aryl groups formed of five-membered and six-membered rings with 9 to 20 carbon atoms, substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group with 1 to 20 carbon atoms, or combinations thereof; or aryl groups formed of six-membered rings with 6 to 20 carbon atoms, substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms, or combinations thereof.

[0145] According to one embodiment of this specification, R1, R2, R4, R5, and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being independently deuterium; phenyl groups substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or combinations thereof; naphthyl groups substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or combinations thereof; biphenyl groups substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or combinations thereof; phenanthyl groups substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or combinations thereof; or fluorenyl groups substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or combinations thereof.

[0146] According to one embodiment of this specification, R1, R2, R4, R5, and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being independently deuterium; phenyl groups substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or combinations thereof; naphthyl groups substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or combinations thereof; biphenyl groups substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or combinations thereof; phenanthyl groups substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or combinations thereof; or fluorenyl groups substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or combinations thereof.

[0147] According to one embodiment of this specification, R1, R2, R4, R5 and R7 to R11 are deuterium, and R3 and R6 are the same as or different from each other, each being independently deuterium; phenyl substituted or unsubstituted by deuterium, phenyl, naphthyl, phenanthryl or a combination thereof; naphthyl substituted or unsubstituted by deuterium, phenyl or a combination thereof; biphenyl substituted or unsubstituted by deuterium; phenanthryl substituted or unsubstituted by deuterium; or fluorenyl substituted or unsubstituted by deuterium, methyl or a combination thereof.

[0148] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium, or a substituted or unsubstituted aryl group.

[0149] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium or an aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0150] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium, or a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0151] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium, or a monocyclic or polycyclic aryl group comprising a six-membered ring with 6 to 30 substituted or unsubstituted carbon atoms.

[0152] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium, or a monocyclic or polycyclic aryl group formed of a six-membered ring with 6 to 30 substituted or unsubstituted carbon atoms.

[0153] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium; or aryl groups with 6 to 20 substituted or unsubstituted carbon atoms.

[0154] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium, or a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0155] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium, or a monocyclic or polycyclic aryl group comprising a six-membered ring with 6 to 20 substituted or unsubstituted carbon atoms.

[0156] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium, or a monocyclic or polycyclic aryl group formed of a six-membered ring with 6 to 20 substituted or unsubstituted carbon atoms.

[0157] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium, or an aryl group that is substituted with deuterium or not substituted.

[0158] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium or an aryl group with 6 to 30 carbon atoms that are either substituted with deuterium or unsubstituted.

[0159] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium, or a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms that are either substituted with or unsubstituted with deuterium.

[0160] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium, or a monocyclic or polycyclic aryl group comprising a six-membered ring with 6 to 30 carbon atoms substituted or unsubstituted with deuterium.

[0161] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is a deuterium, or an aryl group consisting of a six-membered ring and having 6 to 30 carbon atoms substituted or unsubstituted with deuterium.

[0162] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium or an aryl group with 6 to 20 carbon atoms that are either substituted with deuterium or unsubstituted.

[0163] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium, or a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms that are either substituted with or unsubstituted with deuterium.

[0164] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium, or an aryl group comprising a six-membered ring and having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0165] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is a deuterium, or an aryl group consisting of a six-membered ring and having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0166] According to one embodiment of this specification, R1 to R5 and R7 to R11 are deuterium, and R6 is deuterium, a phenyl group substituted with or unsubstituted with deuterium, or a naphthyl group substituted with or unsubstituted with deuterium.

[0167] According to one embodiment of this specification, R3 is deuterium, or a substituted or unsubstituted aryl group.

[0168] According to one embodiment of this specification, R3 is deuterium, or an aryl group having 6 to 30 substituted or unsubstituted carbon atoms.

[0169] According to one embodiment of this specification, R3 is deuterium, or a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0170] According to one embodiment of this specification, R3 is a deuterium, a polycyclic aryl group comprising a five-membered or six-membered ring with 9 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic aryl group comprising a six-membered ring with 6 to 30 substituted or unsubstituted carbon atoms.

[0171] According to one embodiment of this specification, R3 is a deuterium, a polycyclic aryl group consisting of a five-membered ring and a six-membered ring with 9 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic aryl group consisting of a six-membered ring with 6 to 30 substituted or unsubstituted carbon atoms.

[0172] According to one embodiment of this specification, R3 is deuterium, or an aryl group having 6 to 20 substituted or unsubstituted carbon atoms.

[0173] According to one embodiment of this specification, R3 is deuterium, or a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0174] According to one embodiment of this specification, R3 is a deuterium, a polycyclic aryl group comprising a five-membered or six-membered ring with 9 to 20 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic aryl group comprising a six-membered ring with 6 to 20 substituted or unsubstituted carbon atoms.

[0175] According to one embodiment of this specification, R3 is a deuterium, a polycyclic aryl group consisting of a five-membered ring and a six-membered ring with 9 to 20 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic aryl group consisting of a six-membered ring with 6 to 20 substituted or unsubstituted carbon atoms.

[0176] According to one embodiment of this specification, R3 is deuterium; or an aryl group substituted with or unsubstituted with deuterium, alkyl, aryl, or a combination thereof.

[0177] According to one embodiment of this specification, R3 is deuterium; or is a deuterium, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a combination thereof, or an unsubstituted aryl group having 6 to 30 carbon atoms.

[0178] According to one embodiment of this specification, R3 is deuterium; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0179] According to one embodiment of this specification, R3 is deuterium; a polycyclic aryl group comprising a five-membered ring and a six-membered ring, substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a combination thereof; or a monocyclic or polycyclic aryl group comprising a six-membered ring, substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0180] According to one embodiment of this specification, R3 is deuterium; a polycyclic aryl group with 9 to 30 carbon atoms formed by a five-membered ring and a six-membered ring, substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group with 1 to 30 carbon atoms, or a combination thereof; or a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms formed by a six-membered ring, substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or a combination thereof.

[0181] According to one embodiment of this specification, R3 is deuterium; or is a deuterium, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a combination thereof, or an unsubstituted aryl group having 6 to 20 carbon atoms.

[0182] According to one embodiment of this specification, R3 is deuterium; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0183] According to one embodiment of this specification, R3 is deuterium; a polycyclic aryl group comprising a five-membered or six-membered ring and having 9 to 20 carbon atoms, substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a combination thereof; or a monocyclic or polycyclic aryl group comprising a six-membered ring and having 6 to 20 carbon atoms, substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0184] According to one embodiment of this specification, R3 is deuterium; a polycyclic aryl group with 9 to 20 carbon atoms formed by a five-membered ring and a six-membered ring, substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group with 1 to 20 carbon atoms, or a combination thereof; or a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms formed by a six-membered ring, substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms, or a combination thereof.

[0185] According to one embodiment of this specification, R3 is deuterium; a phenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a naphthyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a phenanthryl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; or a fluorenyl group substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a combination thereof.

[0186] According to one embodiment of this specification, R3 is deuterium; a phenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; a naphthyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; a phenanthryl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; or a fluorenyl group substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a combination thereof.

[0187] According to one embodiment of this specification, R3 is deuterium; a phenyl group substituted or unsubstituted with deuterium, phenyl, naphthyl, phenanthryl, or a combination thereof; a naphthyl group substituted or unsubstituted with deuterium, phenyl, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium; a phenanthryl group substituted or unsubstituted with deuterium; or a fluorenyl group substituted or unsubstituted with deuterium, methyl, or a combination thereof.

[0188] According to one embodiment of this specification, R3 is a substituted or unsubstituted aryl group.

[0189] According to one embodiment of this specification, R3 is an aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0190] According to one embodiment of this specification, R3 is a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0191] According to one embodiment of this specification, R3 is a polycyclic aryl group comprising a five-membered ring or a six-membered ring, with 9 to 30 substituted or unsubstituted carbon atoms; or a monocyclic or polycyclic aryl group comprising a six-membered ring, with 6 to 30 substituted or unsubstituted carbon atoms.

[0192] According to one embodiment of this specification, R3 is a polycyclic aryl group formed by a five-membered ring and a six-membered ring with 9 to 30 substituted or unsubstituted carbon atoms; or a monocyclic or polycyclic aryl group formed by a six-membered ring with 6 to 30 substituted or unsubstituted carbon atoms.

[0193] According to one embodiment of this specification, R3 is an aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0194] According to one embodiment of this specification, R3 is a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0195] According to one embodiment of this specification, R3 is a polycyclic aryl group comprising a five-membered ring or a six-membered ring, with 9 to 20 substituted or unsubstituted carbon atoms; or a monocyclic or polycyclic aryl group comprising a six-membered ring, with 6 to 20 substituted or unsubstituted carbon atoms.

[0196] According to one embodiment of this specification, R3 is a polycyclic aryl group formed by a five-membered ring and a six-membered ring with 9 to 20 substituted or unsubstituted carbon atoms; or a monocyclic or polycyclic aryl group formed by a six-membered ring with 6 to 20 substituted or unsubstituted carbon atoms.

[0197] According to one embodiment of this specification, R3 is an aryl group that is substituted with or unsubstituted with deuterium, alkyl, aryl, or a combination thereof.

[0198] According to one embodiment of this specification, R3 is an aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0199] According to one embodiment of this specification, R3 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms that is substituted with or unsubstituted with deuterium, a straight-chain or branched alkyl group with 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or a combination thereof.

[0200] According to one embodiment of this specification, R3 is a polycyclic aryl group comprising a five-membered ring and a six-membered ring, substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a combination thereof; or a monocyclic or polycyclic aryl group comprising a six-membered ring, substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0201] According to one embodiment of this specification, R3 is a polycyclic aryl group with 9 to 30 carbon atoms formed by a five-membered ring and a six-membered ring, substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group with 1 to 30 carbon atoms, or a combination thereof; or a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms formed by a six-membered ring, substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or a combination thereof.

[0202] According to one embodiment of this specification, R3 is an aryl group with 6 to 20 carbon atoms that is substituted or unsubstituted by deuterium, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0203] According to one embodiment of this specification, R3 is a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group with 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms, or a combination thereof.

[0204] According to one embodiment of this specification, R3 is a polycyclic aryl group comprising a five-membered or six-membered ring, substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a combination thereof; or a monocyclic or polycyclic aryl group comprising a six-membered ring, substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0205] According to one embodiment of this specification, R3 is a polycyclic aryl group with 9 to 20 carbon atoms formed by a five-membered ring and a six-membered ring, substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group with 1 to 20 carbon atoms, or a combination thereof; or a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms formed by a six-membered ring, substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms, or a combination thereof.

[0206] According to one embodiment of this specification, R3 is a phenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a naphthyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a phenanthryl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; or a fluorenyl group substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a combination thereof.

[0207] According to one embodiment of this specification, R3 is a phenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; a naphthyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; a phenanthryl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; or a fluorenyl group substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a combination thereof.

[0208] According to one embodiment of this specification, R3 is a phenyl group substituted or unsubstituted with deuterium, phenyl, naphthyl, phenanthryl, or a combination thereof; a naphthyl group substituted or unsubstituted with deuterium, phenyl, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium; a phenanthryl group substituted or unsubstituted with deuterium; or a fluorenyl group substituted or unsubstituted with deuterium, methyl, or a combination thereof.

[0209] According to one embodiment of this specification, R6 is deuterium, or a substituted or unsubstituted aryl group.

[0210] According to one embodiment of this specification, R6 is deuterium, or an aryl group having 6 to 30 substituted or unsubstituted carbon atoms.

[0211] According to one embodiment of this specification, R6 is deuterium, or a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0212] According to one embodiment of this specification, R6 is deuterium, or an aryl group comprising a six-membered ring and consisting of a monocyclic or polycyclic ring with 6 to 30 substituted or unsubstituted carbon atoms.

[0213] According to one embodiment of this specification, R6 is deuterium, or an aryl group consisting of a six-membered ring and a monocyclic or polycyclic ring with 6 to 30 substituted or unsubstituted carbon atoms.

[0214] According to one embodiment of this specification, R6 is deuterium, or an aryl group having 6 to 20 substituted or unsubstituted carbon atoms.

[0215] According to one embodiment of this specification, R6 is deuterium, or a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0216] According to one embodiment of this specification, R6 is deuterium, or an aryl group comprising a six-membered ring and consisting of a monocyclic or polycyclic ring having 6 to 20 substituted or unsubstituted carbon atoms.

[0217] According to one embodiment of this specification, R6 is deuterium, or an aryl group consisting of a six-membered ring and a monocyclic or polycyclic ring with 6 to 20 substituted or unsubstituted carbon atoms.

[0218] According to one embodiment of this specification, R6 is deuterium; or an aryl group substituted with or unsubstituted with deuterium, alkyl, aryl, or a combination thereof.

[0219] According to one embodiment of this specification, R6 is deuterium; or is a deuterium, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a combination thereof, or an unsubstituted aryl group having 6 to 30 carbon atoms.

[0220] According to one embodiment of this specification, R6 is deuterium; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0221] According to one embodiment of this specification, R6 is deuterium; or a monocyclic or polycyclic aryl group containing a six-membered ring and substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0222] According to one embodiment of this specification, R6 is deuterium; or a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or a combination thereof, formed of a six-membered ring.

[0223] According to one embodiment of this specification, R6 is deuterium; or is a 6- to 20-carbon alkyl group substituted with or unsubstituted with deuterium, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0224] According to one embodiment of this specification, R6 is deuterium; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0225] According to one embodiment of this specification, R6 is deuterium; or a monocyclic or polycyclic aryl group containing a six-membered ring and substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0226] According to one embodiment of this specification, R6 is deuterium; or a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms, or a combination thereof, formed of a six-membered ring.

[0227] According to one embodiment of this specification, R6 is deuterium; a phenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a naphthyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; or a phenanthryl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0228] According to one embodiment of this specification, R6 is deuterium; a phenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; a naphthyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; or a phenanthryl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0229] According to one embodiment of this specification, R6 is deuterium; a phenyl group substituted or unsubstituted with deuterium, phenyl, naphthyl, phenanthryl, or a combination thereof; a naphthyl group substituted or unsubstituted with deuterium, phenyl, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium; or a phenanthryl group substituted or unsubstituted with deuterium.

[0230] According to one embodiment of this specification, R6 is a substituted or unsubstituted aryl group.

[0231] According to one embodiment of this specification, R6 is an aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0232] According to one embodiment of this specification, R6 is a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0233] According to one embodiment of this specification, R6 is an aryl group comprising a six-membered ring and consisting of a monocyclic or polycyclic aryl group, with 6 to 30 substituted or unsubstituted carbon atoms.

[0234] According to one embodiment of this specification, R6 is an aryl group consisting of a monocyclic or polycyclic ring formed from a six-membered ring and having 6 to 30 substituted or unsubstituted carbon atoms.

[0235] According to one embodiment of this specification, R6 is an aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0236] According to one embodiment of this specification, R6 is a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0237] According to one embodiment of this specification, R6 is an aryl group comprising a six-membered ring and consisting of a monocyclic or polycyclic aryl group, with 6 to 20 substituted or unsubstituted carbon atoms.

[0238] According to one embodiment of this specification, R6 is an aryl group consisting of a monocyclic or polycyclic ring formed from a six-membered ring and having 6 to 20 substituted or unsubstituted carbon atoms.

[0239] According to one embodiment of this specification, R6 is an aryl group that is substituted with or unsubstituted with deuterium, alkyl, aryl, or a combination thereof.

[0240] According to one embodiment of this specification, R6 is an aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0241] According to one embodiment of this specification, R6 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group with 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or a combination thereof.

[0242] According to one embodiment of this specification, R6 is a monocyclic or polycyclic aryl group containing a six-membered ring, substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0243] According to one embodiment of this specification, R6 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or a combination thereof, formed of a six-membered ring.

[0244] According to one embodiment of this specification, R6 is an aryl group with 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0245] According to one embodiment of this specification, R6 is a straight-chain or branched alkyl group with 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms, or a combination thereof, substituted or unsubstituted, and a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms.

[0246] According to one embodiment of this specification, R6 is a monocyclic or polycyclic aryl group containing a six-membered ring, substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0247] According to one embodiment of this specification, R6 is a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms, substituted or unsubstituted by a deuterium, a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms, or a combination thereof, formed of a six-membered ring.

[0248] According to one embodiment of this specification, R6 is a phenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a naphthyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; or a phenanthryl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0249] According to one embodiment of this specification, R6 is a phenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; a naphthyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; or a phenanthryl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0250] According to one embodiment of this specification, R6 is a phenyl group substituted or unsubstituted with deuterium, phenyl, naphthyl, phenanthryl, or a combination thereof; a naphthyl group substituted or unsubstituted with deuterium, phenyl, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium; or a phenanthryl group substituted or unsubstituted with deuterium.

[0251] According to one embodiment of this specification, L1 is a directly bonded, substituted, or unsubstituted aryl group having 6 to 30 carbon atoms.

[0252] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms that is directly bonded, substituted, or unsubstituted.

[0253] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group containing a six-membered ring, which is directly bonded, substituted, or unsubstituted, and has 6 to 30 carbon atoms.

[0254] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group formed from a six-membered ring, which is directly bonded, substituted, or unsubstituted, and has 6 to 30 carbon atoms.

[0255] According to one embodiment of this specification, L1 is a directly bonded, substituted, or unsubstituted aryl group having 6 to 20 carbon atoms.

[0256] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms that is directly bonded, substituted, or unsubstituted.

[0257] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group containing a six-membered ring, which is directly bonded, substituted, or unsubstituted, and has 6 to 20 carbon atoms.

[0258] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group formed from a six-membered ring, which is directly bonded, substituted, or unsubstituted, and has 6 to 20 carbon atoms.

[0259] According to one embodiment of this specification, L1 is a directly bonded, deuterated, or unsubstituted aryl group.

[0260] According to one embodiment of this specification, L1 is a arylene group with 6 to 30 carbon atoms that is directly bonded, or substituted with deuterium, or unsubstituted.

[0261] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms that is directly bonded, or substituted with deuterium, or unsubstituted.

[0262] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group containing a six-membered ring, which is directly bonded or has been substituted with deuterium or is unsubstituted.

[0263] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group formed by a six-membered ring, which is directly bonded or has been substituted with deuterium or is unsubstituted, and has 6 to 30 carbon atoms.

[0264] According to one embodiment of this specification, L1 is a aryl group with 6 to 20 carbon atoms that is directly bonded, or substituted with deuterium, or unsubstituted.

[0265] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms that is directly bonded, or substituted with deuterium, or unsubstituted.

[0266] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group containing a six-membered ring, which is directly bonded or has been substituted with deuterium or is unsubstituted.

[0267] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group formed of a six-membered ring, which is directly bonded or has been substituted with deuterium or is unsubstituted, and has 6 to 20 carbon atoms.

[0268] According to one embodiment of this specification, L1 is a directly bonded, deuterated or unsubstituted phenylene, or a deuterated or unsubstituted naphthylene.

[0269] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms that is directly bonded, or substituted with deuterium or not substituted, and L1 does not contain substituted or unsubstituted divalent anthracene groups.

[0270] According to one embodiment of this specification, L1 does not contain substituted or unsubstituted divalent anthracene groups.

[0271] According to one embodiment of this specification, Ar1 is an aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0272] According to one embodiment of this specification, Ar1 is a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0273] According to one embodiment of this specification, Ar1 is an aryl group consisting of a monocyclic or polycyclic ring containing a five- or six-membered ring and having substituted or unsubstituted carbon atoms numbering from 6 to 30.

[0274] According to one embodiment of this specification, Ar1 is an aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0275] According to one embodiment of this specification, Ar1 is a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0276] According to one embodiment of this specification, Ar1 is an aryl group comprising a monocyclic or polycyclic ring containing a five- or six-membered ring and having substituted or unsubstituted carbon atoms numbering from 6 to 20.

[0277] According to one embodiment of this specification, the Ar1 mentioned above is an aryl group that is substituted or unsubstituted with deuterium, alkyl, or a combination thereof.

[0278] According to one embodiment of this specification, the Ar1 mentioned above is an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium, an alkyl group having 1 to 30 carbon atoms, or a combination thereof.

[0279] According to one embodiment of this specification, the Ar1 mentioned above is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a combination thereof.

[0280] According to one embodiment of this specification, the Ar1 mentioned above is a monocyclic or polycyclic aryl group comprising a five-membered or six-membered ring and substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a combination thereof, having 6 to 30 carbon atoms.

[0281] According to one embodiment of this specification, the Ar1 mentioned above is an aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium, an alkyl group having 1 to 20 carbon atoms, or a combination thereof.

[0282] According to one embodiment of this specification, the Ar1 mentioned above is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a combination thereof.

[0283] According to one embodiment of this specification, the Ar1 mentioned above is a monocyclic or polycyclic aryl group comprising a five-membered or six-membered ring and substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a combination thereof, having 6 to 20 carbon atoms.

[0284] According to one embodiment of this specification, Ar1 is a substituted or unsubstituted fluorenyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted phenanthryl.

[0285] According to one embodiment of this specification, Ar1 is a fluorenyl group substituted or unsubstituted with deuterium, alkyl, or a combination thereof; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; or a phenanthryl group substituted or unsubstituted with deuterium.

[0286] According to one embodiment of this specification, Ar1 is a fluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 30 carbon atoms, or a combination thereof; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; or a phenanthryl group substituted or unsubstituted with deuterium.

[0287] According to one embodiment of this specification, the Ar1 mentioned above is a fluorenyl group substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a combination thereof; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; or a phenanthryl group substituted or unsubstituted with deuterium.

[0288] According to one embodiment of this specification, Ar1 is a fluorenyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 20 carbon atoms, or a combination thereof; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; or a phenanthryl group substituted or unsubstituted with deuterium.

[0289] According to one embodiment of this specification, Ar1 is a fluorenyl group substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a combination thereof; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; or a phenanthryl group substituted or unsubstituted with deuterium.

[0290] According to one embodiment of this specification, Ar1 is a fluorenyl group substituted or unsubstituted with deuterium, methyl, or a combination thereof; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; or a phenanthryl group substituted or unsubstituted with deuterium.

[0291] According to one embodiment of this specification, Ar1 is a fluorenyl group substituted with deuterium, methyl, or a combination thereof; a phenyl group substituted with deuterium or unsubstituted; a biphenyl group substituted with deuterium or unsubstituted; a naphthyl group substituted with deuterium or unsubstituted; or a phenanthryl group substituted with deuterium or unsubstituted.

[0292] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently an alkyl group having 1 to 30 carbon atoms, either substituted or unsubstituted.

[0293] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently a straight-chain or chain alkyl group having 1 to 30 carbon atoms, whether substituted or unsubstituted.

[0294] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently an alkyl group having 1 to 20 carbon atoms, either substituted or unsubstituted.

[0295] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently a straight-chain or branched alkyl group having 1 to 20 carbon atoms, whether substituted or unsubstituted.

[0296] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently an alkyl group having 1 to 10 carbon atoms, either substituted or unsubstituted.

[0297] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently a straight-chain or branched alkyl group having 1 to 10 carbon atoms, whether substituted or unsubstituted.

[0298] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently an alkyl group having 1 to 4 carbon atoms, either substituted or unsubstituted.

[0299] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently a straight-chain or branched alkyl group having 1 to 4 carbon atoms, whether substituted or unsubstituted.

[0300] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently an alkyl group.

[0301] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently an alkyl group having 1 to 30 carbon atoms.

[0302] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0303] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently an alkyl group having 1 to 20 carbon atoms.

[0304] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently a straight-chain or branched alkyl group having 1 to 20 carbon atoms.

[0305] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently an alkyl group having 1 to 10 carbon atoms.

[0306] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently a straight-chain or branched alkyl group having 1 to 10 carbon atoms.

[0307] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently an alkyl group having 1 to 4 carbon atoms.

[0308] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently a straight-chain or branched alkyl group having 1 to 4 carbon atoms.

[0309] According to one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently a straight-chain alkyl group having 1 to 4 carbon atoms.

[0310] According to one embodiment of this specification, R101 and R102 are methyl groups.

[0311] In this specification, "containing deuterium", "deuterated" or "deuterated" means that hydrogen at a substituted position in a compound is replaced by deuterium.

[0312] In this specification, "per-deuterated" refers to a compound or group in which all hydrogen atoms in the molecule are replaced by deuterium, and has the same meaning as "100% deuterated".

[0313] In this specification, "X% deuterated", "degree of deuteration X%" or "deuteration rate X%" means that X% of the hydrogens at the substituted positions in the structure are substituted with deuterium. For example, when the structure is dibenzofuran, "25% deuterated" of the dibenzofuran, "degree of deuteration 25%" of the dibenzofuran, or "deuteration rate 25%" of the dibenzofuran can mean that 2 out of the 8 hydrogens at the substituted positions in the dibenzofuran are substituted with deuterium. Alternatively, it can mean that all 8 hydrogens at the substituted positions are substituted with 25% deuterium or that 4 out of the 8 hydrogens at the substituted positions are substituted with 50% deuterium.

[0314] In this specification, the deuterium being replaced is the deuterium with a substitution rate of 1% or more and 99.9% or less.

[0315] In this specification, "degree of deuteration" or "deuteration substitution rate" can be determined by nuclear magnetic resonance spectroscopy (NMR spectroscopy). 1 The assay was confirmed using known methods such as ¹H NMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry).

[0316] Specifically, through nuclear magnetic resonance spectroscopy (NMR spectroscopy) 1 When analyzing "degree of deuteration" or "deuteration substitution rate" using ¹H NMR, DMF (dimethylformamide) can be added as an internal standard. 1 The integration ratio on H NMR is used to calculate the degree of deuteration or the rate of deuteration substitution from the total peak integration.

[0317] Additionally, when analyzing "degree of deuteration" or "deuteration substitution rate" using TLC / MS (thin-layer chromatography / mass spectrometry), the substitution rate can be calculated based on the maximum value (intermediate value) of the molecular weight distribution at the end of the reaction. For example, when analyzing the degree of deuteration of compound A below, the molecular weight of the starting material is 506. When specifying... Figure 6 When the maximum molecular weight (median value) of compound A in the MS spectrum is 527, 21 of the 26 substituted hydrogen positions in the starting material are replaced by deuterium, so it can be calculated that about 81% of the hydrogen is deuterated.

[0318]

[0319] [Starting material] [Compound A]

[0320] In this specification, D represents deuterium.

[0321] According to one embodiment of this specification, the above-mentioned chemical formula 1 is any one of the following compounds.

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334] The compound of Formula 1 according to one embodiment of this specification can be manufactured with a core structure using the same method as the manufacturing example described later. Other substituents can be added using methods known in the art, and the type, position, or number of substituents can be varied according to techniques known in the art.

[0335] In this specification, compounds with various band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above-described chemical formula 1. Furthermore, in this specification, the HOMO and LUMO energy levels of the compound can also be tuned by introducing various substituents into the core structure as described above.

[0336] In addition, this specification provides organic light-emitting devices containing the above-mentioned compounds.

[0337] 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.

[0338] 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.

[0339] 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.

[0340] 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.

[0341] In this specification, the meaning of a specific substance A being contained in layer C or layer D includes all cases where i) substance A is contained in one or more layers of layer C, or ii) substance A is contained in one or more layers of layer D, or iii) substance A is contained in one or more layers of layer C and one or more layers of layer D respectively.

[0342] The organic light-emitting device according to this specification is characterized in that it comprises: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers comprises a compound represented by the above-described chemical formula 1.

[0343] The organic light-emitting device described in this specification can be manufactured using conventional organic light-emitting device manufacturing methods and materials, except for the organic layer formed by the compound of chemical formula 1 described above.

[0344] 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.

[0345] The organic layers of the organic light-emitting device described in this specification can be formed as a single layer or as a multilayer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of this invention may have a structure comprising one or more of the following as organic layers: a hole transport layer, a hole injection layer, an electron blocking (hole modulation) layer, a hole transport and injection layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking (electron modulation) layer, and an electron transport and injection layer. However, the structure of the organic light-emitting device described in this specification is not limited thereto, and may include fewer or more organic layers.

[0346] At this point, the aforementioned light-emitting layer contains the aforementioned compound as the main body of the light-emitting layer, and may contain additional main bodies and dopants. The aforementioned additional main bodies may be included together in the organic layer containing the aforementioned compound, or they may be included in another adjacent organic layer.

[0347] In the organic light-emitting device of this specification, the light-emitting layer may contain additional host and dopant, and may contain the above-mentioned host and dopant in a weight ratio of 99:1 to 1:99, preferably in a weight ratio of 99:1 to 70:30, and more preferably in a weight ratio of 99:1 to 85:15.

[0348] According to one embodiment of this specification, the light-emitting layer is a blue light-emitting layer with a maximum emission wavelength of 440 nm to 480 nm.

[0349] The organic light-emitting device described in this specification may also include one or more organic layers selected from the following: a hole transport layer, a hole injection layer, an electron blocking (hole modulation) layer, an electron injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking (electron modulation) layer, and a hole injection and transport layer.

[0350] In one embodiment of this specification, the organic light-emitting device includes: an anode, a cathode, and two or more organic layers disposed between the anode and the cathode, wherein at least one of the two or more organic layers contains a compound represented by the above chemical formula 1.

[0351] 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).

[0352] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with a reverse structure (inverted type) in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate.

[0353] The organic light-emitting device structure described in this specification can have the following characteristics: Figures 1 to 5 The structure shown is not limited to this.

[0354] Figure 1 An example is shown of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 6, and a cathode 10 are sequentially stacked. In the structure described above, the aforementioned compound may be included in the light-emitting layer 6.

[0355] Figure 2 An example is shown of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking (hole modulation) layer 5, a light-emitting layer 6, a hole blocking (electron modulation) layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10. In the structure described above, the aforementioned compound may be included in the light-emitting layer 6.

[0356] Figure 3 An example is shown of an organic light-emitting device comprising a substrate 1, an anode 2, a hole injection and transport layer 34, a light-emitting layer 6, an electron transport layer 8, an electron injection layer 9, and a cathode 10, stacked sequentially. In the structure described above, the aforementioned compound may be included in the light-emitting layer 6.

[0357] Figure 4 An example is shown of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a hole injection and transport layer 34, a first light-emitting layer 6-1, a second light-emitting layer 6-2, an electron transport layer 8, an electron injection layer 9, and a cathode 10. In the structure described above, the aforementioned compound may be contained in the first light-emitting layer 6-1.

[0358] Figure 5 An example is shown of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking (hole modulation) layer 5, a first light-emitting layer 6-1, a second light-emitting layer 6-2, a first electron transport layer 8-1, a second electron transport layer 8-2, an electron injection layer 9, and a cathode 10. In the structure described above, the aforementioned compound may be included in the first light-emitting layer 6-1.

[0359] In one embodiment of this specification, the electron blocking (hole modulation) layer and the light-emitting layer may be disposed adjacent to each other. For example, the electron blocking (hole modulation) layer and the light-emitting layer may be physically connected.

[0360] In one embodiment of this specification, the hole transport layer and the electron blocking (hole modulation) layer may be disposed adjacent to each other. For example, the hole transport layer and the electron blocking (hole modulation) layer may be physically connected.

[0361] The organic light-emitting device described in this specification, except for one or more layers of organic material containing the aforementioned compound, i.e., the compound of chemical formula 1, can be manufactured using materials and methods known in the art.

[0362] When the aforementioned organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed from the same substance or different substances.

[0363] For example, the organic light-emitting device according to 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 a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking (hole modulation) layer, an electron transport layer, and an electron injection layer is formed on the anode. Finally, a material suitable for use as a cathode is deposited onto the organic layer. Alternatively, the organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto the substrate.

[0364] In addition, when the organic layer of the above-mentioned organic light-emitting device contains two or more compounds, it can be deposited by co-evaporation or pre-mixing.

[0365] The aforementioned organic layer may also include one or more of the following: a hole transport layer, a hole injection layer, an electron blocking (hole modulation) layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking (electron modulation) layer, and a hole injection and transport layer.

[0366] The aforementioned organic layer can be a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking (hole modulation) layer, a light-emitting layer and an electron transport layer, an electron injection layer, and an electron injection and transport layer, but it 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.

[0367] 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 that can be used as anode materials 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.

[0368] The cathode described above is the electrode for injecting electrons. 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.

[0369] The aforementioned hole injection layer facilitates the smooth 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, aryl amine compounds, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, perylene compounds, benzonitrile compounds, anthraquinones, and conductive polymers based on polyaniline and polythiophene. Specifically, the aforementioned hole injection layer can use aryl amine compounds and benzonitrile compounds.

[0370] In the organic light-emitting devices described in this specification, the hole injection layer may be made of arylamine compounds substituted with carbazole groups and benzonitrile compounds substituted with halogen groups, but is not limited thereto.

[0371] According to one embodiment of this specification, the hole injection layer comprises, but is not limited to, a compound represented by the chemical formula HI-1.

[0372] [Chemical formula HI-1]

[0373]

[0374] In the above chemical formula HI-1,

[0375] R315 to R317 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 heteroaryl, and combinations thereof, or may be combined with adjacent groups to form substituted or unsubstituted rings.

[0376] r315 is an integer from 1 to 5. When r315 is 2 or more, two or more of the above R315 are either the same or different from each other.

[0377] r316 is an integer from 1 to 5. When r316 is 2 or more, two or more of the above R316 are the same or different from each other.

[0378] According to one embodiment of this specification, R317 is selected from any one of substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, and combinations thereof.

[0379] According to one embodiment of this specification, R317 is selected from carbazolyl, phenyl, biphenyl, terphenyl, triphenylene, and combinations thereof.

[0380] According to one embodiment of this specification, R315 and R316 may be the same as or different from each other, each being independently a substituted or unsubstituted aryl group, or combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an aryl or alkyl group.

[0381] According to one embodiment of this specification, R315 and R316 may be the same as or different from each other, each being independently phenyl, biphenyl, or terphenyl, or combined with adjacent groups to form indene substituted with phenyl or methyl groups.

[0382] According to one embodiment of this specification, the above chemical formula HI-1 is represented by any one of the following compounds.

[0383]

[0384]

[0385]

[0386] According to one embodiment of this specification, the hole injection layer comprises a compound represented by the chemical formula HI-2, but is not limited thereto.

[0387] [Chemical formula HI-2]

[0388]

[0389] In the above chemical formula HI-2,

[0390] R411 to R413 may be the same as or different from each other, and each is an independent halogen group.

[0391] r411 to r413 are each 4.

[0392] According to one embodiment of this specification, each of R411 to R413 is F.

[0393] According to one embodiment of this specification, the above-mentioned chemical formula HI-2 is represented by the following compound.

[0394]

[0395] According to one embodiment of this specification, the hole injection layer comprises the above-described chemical formulas HI-1 and HI-2.

[0396] According to one embodiment of this specification, the hole injection layer comprises the above-mentioned chemical formulas HI-1 and HI-2 in a weight ratio of 1:99 to 99:1.

[0397] The aforementioned hole transport layer facilitates hole transport. Hole transport materials are substances capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer; substances with high hole mobility are suitable. Specific examples of hole transport materials include arylamine compounds, carbazole compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0398] In the organic light-emitting devices described in this specification, the hole transport layer may be a carbazole compound substituted with an arylamine group, but is not limited thereto.

[0399] An electron blocking (hole modulation, or electron suppression) layer may be disposed between the hole transport layer and the light-emitting layer. This electron blocking (hole modulation, electron suppression) layer prevents electrons from flowing from the light-emitting layer into the anode and regulates the flow of holes into the light-emitting layer, thereby regulating the overall performance of the device. Preferably, the electron blocking material (hole modulation material, or electron suppression material) is a compound capable of preventing the inflow of electrons from the light-emitting layer to the anode and regulating the flow of holes injected into the light-emitting layer or the light-emitting material. In one embodiment, an arylamine-based organic compound may be used in the electron blocking (hole modulation, or electron suppression) layer, but it is not limited to this.

[0400] In the organic light-emitting device described in this specification, the electron blocking (hole modulation, or electron suppression) layer may comprise an amine compound containing a carbazole group. As an example, the compound may be formed by linking a carbazole group and an amine group via an ortho-, meta-, or para-biphenyl group.

[0401] According to one embodiment of this specification, the electron blocking (hole modulation, or electron suppression) layer comprises, but is not limited to, a compound with the following chemical formula EB-1.

[0402] [Chemical formula EB-1]

[0403]

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

[0405] R501 to R504 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0406] L101 is a directly bonded, substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.

[0407] Ar101 and Ar102 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0408] l101 is an integer from 1 to 3. When l101 is 2 or more, two or more of the above L101 are the same or different from each other.

[0409] r501 is an integer from 1 to 5. When r501 is 2 or more, two or more of the above R501 are the same or different from each other.

[0410] r504 is an integer from 1 to 5. When r504 is 2 or more, two or more of the above R504 are either the same or different from each other.

[0411] r502 is an integer from 1 to 3. When r502 is 2 or more, two or more of the above R502 are either the same or different from each other.

[0412] r503 is an integer from 1 to 4. When r503 is 2 or more, two or more of the above R503 are the same or different from each other.

[0413] According to one embodiment of this specification, R501 to R504 may be the same as or different from each other, and each is independently hydrogen or deuterium.

[0414] According to one embodiment of this specification, R501 to R504 are hydrogen.

[0415] According to one embodiment of this specification, L101 is a directly bonded monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0416] According to one embodiment of this specification, L101 is directly bonded, phenylene, or naphthylene.

[0417] According to one embodiment of this specification, L101 is a direct bond.

[0418] According to one embodiment of this specification, Ar101 and Ar102 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0419] According to one embodiment of this specification, Ar101 and Ar102 may be the same as or different from each other, and each is independently phenyl, biphenyl, terphenyl, or naphthyl.

[0420] According to one embodiment of this specification, the above-mentioned EB-1 is represented by the following compound.

[0421]

[0422] 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 complex (Alq3), carbazole compounds, diluted styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, and benzo[…]. Compounds such as azoles, benzothiazoles and benzimidazoles, poly(p-phenylenevinylene) (PPV) polymers, spiro compounds, polyfluorene, and fluorene, but not limited to these.

[0423] 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.

[0424] In the organic light-emitting device described in this specification, the main body may be a compound of the above-described chemical formula 1 or anthracene derivatives, but is not limited thereto.

[0425] In the organic light-emitting device described in this specification, the above-mentioned main body may include a compound of the above-mentioned chemical formula 1 as a first main body, and may also include a second main body.

[0426] In the organic light-emitting device described in this specification, the second host can be a compound with the following chemical formula H.

[0427] [Chemical formula H]

[0428]

[0429] In the above chemical formula H,

[0430] L20 and L21 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0431] Ar20 and Ar21 may be the same as or different from each other, and each can be independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0432] R301 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0433] r301 is an integer from 1 to 8. When r301 is 2 or more, two or more r301s are the same or different from each other.

[0434] In one embodiment of this specification, the first body comprises one or more compounds of the above-described chemical formula 1.

[0435] In one embodiment of this specification, the first body comprises two or more compounds of the above-mentioned chemical formula 1, wherein the two or more compounds are different from each other.

[0436] In one embodiment of this specification, the first body comprises a compound of the above-described chemical formula 1, and may also comprise one or more compounds of a different chemical formula than the above-described chemical formula 1.

[0437] In one embodiment of this specification, the first body comprises a compound of the above-mentioned chemical formula 1, and may also comprise one or more compounds of a different system than the above-mentioned chemical formula 1 and one or more compounds other than the system. The compounds other than the system may include compounds with higher triplet energy than the above-mentioned chemical formula H, but are not limited thereto.

[0438] The compounds in the above-mentioned series and compounds other than the series can use conventional compounds, but are not limited to them.

[0439] In one embodiment of this specification, the second body comprises a compound of the above-mentioned chemical formula H, and may also comprise one or more anthracene compounds different from the above-mentioned chemical formula H.

[0440] In one embodiment of this specification, the second body comprises a compound of the above-mentioned chemical formula H, and may also comprise an anthracene compound different from the above-mentioned chemical formula H.

[0441] In one embodiment of this specification, the second body may use two or more compounds of the above chemical formula H. These two or more compounds are different from each other.

[0442] The anthracene compounds mentioned above can be conventional compounds, but are not limited to them.

[0443] 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 heterocyclic group with 2 to 30 carbon atoms.

[0444] In one embodiment of this specification, L20 and L21 may be the same as or different from each other, and each independently is a directly bonded, deuterated or unsubstituted phenylene, deuterated or unsubstituted biphenylene, deuterated or unsubstituted naphthylene, divalent dibenzofuranyl, or divalent dibenzothiopheneyl.

[0445] 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 heterocyclic group with 2 to 30 substituted or unsubstituted carbon atoms.

[0446] 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 an aryl group of a monocyclic to tetracyclic compound having 6 to 20 substituted or unsubstituted carbon atoms, or a heterocyclic group of a monocyclic to tetracyclic compound having 6 to 20 substituted or unsubstituted carbon atoms.

[0447] 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 terphenyl 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 deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms. A monocyclic or polycyclic aryl-substituted or unsubstituted phenanthryl group; a thiophene group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0448] In one embodiment of this specification, the Ar20 and Ar21 described above may be the same as or different from each other, and each independently represents a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a terphenyl, a deuterated or unsubstituted naphthyl, a phenyl-substituted or unsubstituted thiophene, a dibenzofuranyl, a naphthobenzofuranyl, a dibenzothiophene, or a naphthobenzothiophene.

[0449] In one embodiment of this specification, R301 is hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0450] In one embodiment of this specification, R301 is hydrogen; deuterium; an aryl group having 6 to 30 carbon atoms substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted by deuterium.

[0451] In one embodiment of this specification, R301 is hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium, phenyl, naphthyl, or a combination thereof; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium, phenyl, naphthyl, or a combination thereof; a dibenzofuranyl group substituted or unsubstituted with deuterium; or a dibenzothiophenyl group substituted or unsubstituted with deuterium.

[0452] In one embodiment of this specification, R301 is hydrogen.

[0453] In one embodiment of this specification, R301 is deuterium.

[0454] According to one embodiment of this specification, the above chemical formula H is any one of the following compounds.

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466] According to one embodiment of this specification, the first and second bodies described above can be deposited on the light-emitting layer in a bi-layer, co-deposited, or pre-mixed manner.

[0467] According to one embodiment of this specification, the second body described above can be used as a hyperfluorescence (or triple-sensitized fluorescence) body for the luminescent layer.

[0468] When the emissive layer emits red light, phosphorescent materials such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetonateiridium), PQIr (tris(1-phenylquinoline)iridium), and PtOEP (octaethylporphyrin platinum) can be used as luminescent dopants, but these are not the only options. When the luminescent layer emits green light, phosphorescent materials such as Ir(ppy)3 (facilitated tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3 (tris(8-hydroxyquinoline)aluminum) can be used as luminescent dopants, but these are not the only options. When the luminescent layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic can be used as luminescent dopants; or fluorescent materials such as spiro-DPVBi, spiro-6P, stilbene (DSB), stilbene aryl (DSA), PFO-based polymers, PPV-based polymers, etc., but these are not the only options.

[0469] In the organic light-emitting devices described in this specification, the light-emitting dopants may include polycyclic compounds containing bromine, compounds containing Pt, or Ir complexes, but are not limited to these.

[0470] In the organic light-emitting device described in this specification, the light-emitting layer may contain a compound of the above chemical formula 1 as the main body, and may also contain dopants.

[0471] In the organic light-emitting device described in this specification, the dopant may be a compound of the following chemical formula D.

[0472] [Chemical formula D]

[0473]

[0474] In the above chemical formula D,

[0475] X1 and X2 may be the same as or different from each other, and each is independently CR', NR" or O, with at least one of X1 and X2 being NR".

[0476] A and C may be the same as or different from each other, and each may independently be a substituted or unsubstituted five-membered ring or a substituted or unsubstituted six-membered ring.

[0477] R401, R', and R" may be the same as or different from each other, and each independently represents hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted silyl group, substituted or unsubstituted amino group, substituted or unsubstituted aryl group, substituted or unsubstituted fused ring group formed by the fusion of aromatic hydrocarbon ring and aliphatic hydrocarbon ring, or substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring formed by combining with adjacent groups.

[0478] r401 is an integer from 1 to 3. When r401 is 2 or more, the substituents in the parentheses are the same or different from each other.

[0479] According to one embodiment of this specification, A and C may be the same as or different from each other, and each is independently a substituted or unsubstituted five- or six-membered hydrocarbon ring, or a substituted or unsubstituted five- or six-membered heterocycle, or their fused rings.

[0480] According to one embodiment of this specification, A and C may be the same as or different from each other, and each is independently a five- or six-membered hydrocarbon ring substituted or unsubstituted with an alkyl or arylamine group, or a five- or six-membered heterocycle substituted or unsubstituted with an alkyl group.

[0481] According to one embodiment of this specification, A and C may be the same as or different from each other, and each independently is a benzene substituted or unsubstituted with an arylamine group, a tetrahydronaphthalene substituted or unsubstituted with an alkyl group, a benzofuran substituted or unsubstituted with an alkyl group, a tetrahydronaphthothiophene substituted or unsubstituted with an alkyl group, or a benzothiophene substituted or unsubstituted with an alkyl group.

[0482] According to one embodiment of this specification, A and C may be the same as or different from each other, and each independently represents benzene substituted or unsubstituted with diphenylamine, benzofuran substituted or unsubstituted with tert-butyl, benzothiophene substituted or unsubstituted with tert-butyl, (1,1,4,4)-tetramethyl-(1,2,3,4)-tetrahydronaphthothiophene, (1,1,4,4)-tetramethyl-(1,2,3,4)-tetrahydronaphthofuran, or (1,1,4,4)-tetramethyl-(1,2,3,4)-tetrahydronaphthyl.

[0483] According to one embodiment of this specification, R401, R' and R" may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted fused cyclic group formed by fusion of aromatic hydrocarbon ring and aliphatic hydrocarbon ring, or substituted or unsubstituted aryl.

[0484] According to one embodiment of this specification, R401 is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

[0485] According to one embodiment of this specification, R401 is methyl, tert-butyl, or phenyl.

[0486] According to one embodiment of this specification, R" is a substituted or unsubstituted aryl group, or a substituted or unsubstituted fused ring group formed by the fusion of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.

[0487] According to one embodiment of this specification, R" is a substituted or unsubstituted phenyl group or a substituted or unsubstituted tetrahydronaphthyl group.

[0488] According to one embodiment of this specification, R" is a phenyl substituted or unsubstituted with methyl or tert-butyl, a phenyl substituted with methyl and adamantyl, a biphenyl substituted or unsubstituted with tert-butyl, or (1,1,4,4)-tetramethyl-(1,2,3,4)-tetrahydronaphthyl.

[0489] According to one embodiment of this specification, r401 is 1.

[0490] According to one embodiment of this specification, the above chemical formula D is any one of the following compounds.

[0491]

[0492] In addition, one embodiment of this specification provides an organic light-emitting device, which includes: an anode, a cathode, a first light-emitting layer disposed between the anode and the cathode, and a second light-emitting layer disposed between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, wherein the first light-emitting layer contains a compound of chemical formula 1, and the second light-emitting layer contains a compound of chemical formula H.

[0493] In an organic light-emitting device according to one embodiment of this specification, the light-emitting layer is a plurality of layers, two or more, and each of the different light-emitting layers may contain a compound of chemical formula 1 and a compound of chemical formula H. For example, the light-emitting layer may include a first light-emitting layer containing a compound of chemical formula 1 and a second light-emitting layer containing a compound of chemical formula H. In this case, the second light-emitting layer may be disposed between the first light-emitting layer and the cathode. The first light-emitting layer and the second light-emitting layer are disposed in contact with each other. When the first light-emitting layer and the second light-emitting layer each contain a compound of chemical formula 1 and a compound of chemical formula H as the main components, each of the first light-emitting layer and the second light-emitting layer also contains a dopant compound. In this case, the first light-emitting layer and the second light-emitting layer may contain dopant materials of the same type or different types, but it is preferable to contain dopant materials of the same type.

[0494] In an organic light-emitting device according to one embodiment of this specification, the second light-emitting layer is disposed between the first light-emitting layer and the cathode.

[0495] In an organic light-emitting device according to one embodiment of this specification, the first light-emitting layer and the second light-emitting layer are disposed in direct contact. With this configuration, the efficiency of the organic light-emitting device can be further improved.

[0496] According to one embodiment of this specification, the above-mentioned chemical formula 1 is the main body of the first light-emitting layer.

[0497] According to one embodiment of this specification, the above-mentioned chemical formula H is the main body of the second light-emitting layer.

[0498] According to one embodiment of this specification, the first light-emitting layer and the second light-emitting layer each contain a dopant, as described above.

[0499] According to one embodiment of this specification, the first light-emitting layer comprises a compound of Chemical Formula 1 as the main body and also comprises a dopant material. In this case, relative to the total weight of the compound of Chemical Formula 1 in the first light-emitting layer, the dopant material may be included in an amount of about 0.01 to 20 wt%, or 0.01 to 10 wt%.

[0500] According to one embodiment of this specification, the second light-emitting layer comprises a compound of the chemical formula H as the main body, and also comprises a dopant material. In this case, relative to the total weight of the compound of the chemical formula H in the second light-emitting layer, it may contain approximately 0.01 to 20 wt%, or 0.01 to 10 wt% of the dopant material.

[0501] A hole-blocking (electron modulation) layer can be disposed between the electron transport layer and the light-emitting layer. This hole-blocking (electron modulation) layer is designed to block holes from flowing from the light-emitting layer into the cathode and to modulate the flow of electrons into the light-emitting layer, thereby modulating the overall performance of the device. Preferably, the hole-blocking (electron modulation) material is a compound capable of preventing the inflow of holes from the light-emitting layer to the cathode and modulating the electrons injected into the light-emitting layer or the light-emitting material. Suitable materials can be used as the hole-blocking (electron modulation) material depending on the composition of the organic layer used within the device. Specifically, there are… Diazole or triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc., but not limited to these.

[0502] In one embodiment of this specification, the hole-blocking (electronic regulation) layer may comprise a compound having the following structure: an N-containing ring directly attached to the spiro[fluorene-9,9'-xanthene] structure or attached to the N-containing ring via a linking group.

[0503] The aforementioned electron transport layer facilitates electron transport. Electron transport materials are those capable of readily accepting electrons from the cathode and transferring them to the luminescent layer; materials with high electron mobility are suitable. Specific examples include the aforementioned compounds, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, etc., but are not limited to these.

[0504] In one embodiment of this specification, the electron transport layer may contain a compound containing an N-ring, and may also contain an n-type dopant or an organometallic compound. According to one example, the compound containing an N-ring may be a triazine compound, and the n-type dopant or organometallic compound may preferably be a lithium metal coordination compound, for example, lithium 8-hydroxyquinoline, and may contain the compound containing the N-ring and the n-type dopant (or organometallic compound) in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.

[0505] According to one embodiment of this specification, the above-mentioned electronic transport layer has one or more layers.

[0506] According to one embodiment of this specification, the electron transport layer has two layers, including a first electron transport layer and a second electron transport layer.

[0507] According to one embodiment of this specification, the electron transport layer comprises the following chemical formula ET-1.

[0508] [Chemical formula ET-1]

[0509]

[0510] In the above chemical formula ET-1,

[0511] Any one of R601 to R604 is The rest may be the same as or different from each other, and each is independently hydrogen, deuterium, or cyano.

[0512] r601 to r604 are each integers from 1 to 4. When each of r601 to r604 is 2 or more, there are two or more of each of the above R601 to R604 that are the same or different from each other.

[0513] L102 is directly bonded to, substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups.

[0514] l102 is an integer from 1 to 3. When l102 is 2 or more, two or more of the above L102 are the same or different from each other.

[0515] At least one of Z1 to Z3 is N, and the rest are CH.

[0516] Ar201 and Ar202 may be the same as or different from each other, and each may be a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0517] According to one embodiment of this specification, R601 to R604 are not... The rest may be the same as or different from each other, and each is independently hydrogen or cyano.

[0518] According to one embodiment of this specification, L102 is a directly bonded monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0519] According to one embodiment of this specification, L102 is directly bonded, phenylene, or naphthylene.

[0520] According to one embodiment of this specification, L102 is directly bonded.

[0521] According to one embodiment of this specification, the Ar201 and Ar202 described above may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0522] According to one embodiment of this specification, Ar201 and Ar202 may be the same as or different from each other, and each is independently phenyl, biphenyl, or naphthyl.

[0523] According to one embodiment of this specification, Z1 to Z3 are N.

[0524] According to one embodiment of this specification, the above chemical formula ET-1 is any one of the following compounds.

[0525]

[0526]

[0527] According to one embodiment of this specification, the electron transport layer includes a first electron transport layer and a second electron transport layer, wherein the first electron transport layer and the second electron transport layer contain the chemical formula ET-1, and the chemical formula ET-1 contained in the first electron transport layer and the second electron transport layer are different from each other.

[0528] According to one embodiment of this specification, the first electron transport layer and the second electron transport layer comprise the chemical formula ET-1, and the chemical formula ET-1 is different from each other.

[0529] The aforementioned electron transport layer also contains metal coordination compounds. Examples of such metal coordination compounds include lithium 8-hydroxyquinoline (LiQ), 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.

[0530] According to one embodiment of this specification, the second electron transport layer comprises the above-described chemical formula ET-1 and a metal complex. The chemical formula ET-1 and the metal complex are comprised in a weight ratio of 1:9 to 9:1, 4:6 to 6:4, or 1:2 to 2:1.

[0531] 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 possess excellent thin-film forming 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.

[0532] 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.

[0533] In one embodiment of this specification, the electron injection layer may comprise lithium fluoride (LiF).

[0534] In one embodiment of this specification, the electron injection layer comprises LiQ (lithium 8-hydroxyquinoline).

[0535] Depending on the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0536] The aforementioned organic light-emitting devices can be included in various electronic devices. For example, electronic devices containing these organic light-emitting devices can be various electronic devices such as light-emitting devices, authentication devices, display devices, lighting devices, mobile terminals, and wearable devices. Specifically, the aforementioned display devices can include TVs, monitors, smartphones, tablet computers, laptop screens, smartwatches, car dashboards, VR / AR displays, lighting devices, etc.

[0537] The following examples will be provided to illustrate this specification in detail. However, the embodiments described herein can be modified in various other ways and should not be construed as limiting the scope of this application to the embodiments detailed below. The embodiments of this application are provided to provide a more complete explanation of this specification to those skilled in the art.

[0538] Synthesis example 1

[0539]

[0540] Under a nitrogen atmosphere, in a round-bottom flask, 10 g (1 eq.) of compound 6-bromochrysene-1,2,3,4,5,7,8,9,10,11,12-d11 and 7.7 g (1.1 eq.) of phenanthren-9-ylboronic acid were dissolved in 200 ml of 1,4-dioxane. The mixture was stirred in 1,4-dioxane. Even if it was not completely dissolved, aq. K2CO3 (8.7 g, dissolved in 50 mL of distilled water, 2 eq.) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 1 mol%), and the mixture was heated and stirred for 3 hours. After cooling to room temperature, 300 mL of ethanol was added, and the mixture was stirred for 30 minutes. The solid was obtained by direct filtration under reduced pressure. The obtained solid was dissolved in toluene and washed with water. After removing the aqueous layer, the solid was dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from toluene to produce compound BH-1 (7.05 g, 54%).

[0541] MS[M+H] + =416

[0542] Synthesis example 2

[0543]

[0544] Compound BH-2 was synthesized using the same method as in Synthesis Example 1, starting with 10 g (1 eq.) of 6-bromo-1,2,3,4,5,7,8,9,10,11,12-d11 and (3-(naphthalen-2-yl)phenyl)boronic acid (8.6 g, 1.1 eq). Recrystallization under toluene conditions yielded compound BH-2 (7.9 g, 57%).

[0545] Synthesis example 3

[0546]

[0547] Compound BH-3 was synthesized using the same method as in Synthesis Example 1, starting with 6-bromo-1,2,3,4,5,7,8,9,10,11,12-d11 (10 g, 1 eq.) and 2-[4-(9,9-dimethyl-9H-fluoren-4-yl)naphthalen-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2-(4-(9,9-dimethyl-9H-fluoren-4-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (15.4 g, 1.1 eq). Recrystallization under toluene conditions yielded compound BH-3 (9.3 g, 53%).

[0548] Synthesis example 4

[0549]

[0550] Compound BH-4 was synthesized using the same method as in Synthetic Example 1, starting with 6-bromo-12-phenylchrysene-1,2,3,4,5,7,8,9,10,11-d10 (10 g, 1 eq.) and naphthalen-1-ylboronic acid (4.8 g, 1.1 eq). Recrystallization under toluene conditions yielded compound BH-4 (6.8 g, 53%).

[0551] Synthesis example 5

[0552]

[0553] Compound BH-5 was synthesized using the same method as in Synthetic Example 1, starting with 6-bromo-12-(naphthalen-1-yl)chrysene-1,2,3,4,5,7,8,9,10,11-d10 (10 g, 1 eq.) and (9,9-dimethyl-9H-fluoren-3-yl)boronic acid (5.9 g, 1.1 eq). Recrystallization under toluene conditions yielded compound BH-5 (6.2 g, 49%).

[0554] Synthesis example 6

[0555]

[0556] Compound BH-6 was synthesized using the same method as in Synthesis Example 1, starting with 6-bromo-12-(phenyl-d5)-1,2,3,4,5,7,8,9,10,11-d10 (10 g, 1 eq.) and ([1,1'-biphenyl]-4-yl-d9)boronic acid (5.7 g, 1.1 eq). Recrystallization under toluene conditions yielded compound BH-6 (6.6 g, 55%).

[0557] Synthesis Example 7

[0558]

[0559] Compound BH-7 was synthesized using the same method as in Synthetic Example 1, starting with 6-bromo-12-(naphthalen-1-yl-d7)-1,2,3,4,5,7,8,9,10,11-d10 (10 g, 1 eq.) and (naphthalen-2-yl-d7)boronic acid (4.4 g, 1.1 eq). Recrystallization under toluene conditions yielded compound BH-7 (6.3 g, 56%).

[0560] Synthesis example 8

[0561]

[0562] Synthesis example 8-1)

[0563] Under a nitrogen atmosphere, in a round-bottom flask, 10 g (1 eq.) of compound 12-bromo-3-chloro-6-phenyl-1,2,4,5,7,8,9,10,11-d9 and 5.1 g (1.1 eq.) of ([1,1'-biphenyl]-4-ylboronic acid) were dissolved in 200 ml of tetrahydrofuran and stirred. Even if not completely dissolved, aq. K2CO3 (6.5 g, dissolved in 50 mL of distilled water, 2 eq.) was added, followed by the addition of tetrakis(triphenylphosphine)palladium(0) (1.35 g, 5 mol%), and the mixture was heated and stirred for 3 hours. After cooling to room temperature, 300 mL of ethanol was added, and the mixture was stirred for 30 minutes. The solid was obtained by direct filtration under reduced pressure. The solid was dissolved in toluene and washed with water. The aqueous layer was removed, and the solid was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from toluene to produce compound BH-8-a (7.3 g, 62%).

[0564] MS[M+H] + =500

[0565] Synthesis example 8-2)

[0566] Under a nitrogen atmosphere, in a round-bottom flask, compound BH-8-a (7.3 g, 1 eq.) and phenylboronic acid (2.0 g, 1.1 eq.) were dissolved in 150 ml of 1,4-dioxanone. The mixture was stirred in an alkane. Even if it was not completely dissolved, aq. K3PO4 (6.2 g, dissolved in 30 mL of distilled water, 2 eq.) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.07 g, 1 mol%), and the mixture was heated and stirred for 3 hours. After cooling to room temperature, 200 mL of ethanol was added, and the mixture was stirred for 30 minutes. The solid was obtained by direct filtration under reduced pressure. The obtained solid was dissolved in toluene and washed with water. After removing the aqueous layer, the solid was dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from toluene to produce compound BH-8 (4.4 g, 56%).

[0567] MS[M+H] + =542

[0568] Synthesis example 9

[0569]

[0570] Synthesis example 9-1)

[0571] Compound BH-9-a was synthesized using the same method as in Synthetic Example 8-1, starting with 12-bromo-3-chloro-6-(phenyl-d5)chrysene-1,2,4,5,7,8,9,10,11-d9 (10 g, 1 eq.) and (phenyl-d5)boronic acid (3.2 g, 1.1 eq). Recrystallization under toluene conditions yielded the compound (5.9 g, 59%).

[0572] Synthesis example 9-2)

[0573] Compound BH-9 was synthesized using the same method as in Synthesis Example 8-2, starting with BH-9-a (5.9, 1 eq.) and (4-(naphthalen-1-yl-d7)phenyl-2,3,5,6-d4)boronic acid (3.9 g, 1.1 eq.). Recrystallization under toluene conditions yielded compound BH-9 (5.1 g, 61%).

[0574] Synthesis example 10.

[0575]

[0576] Synthesis example 10-1)

[0577] Compound BH-10-a was synthesized using the same method as in Synthesis Example 8-1, starting with 6-([1,1'-biphenyl]-3-yl)-12-bromo-3-chlorochrysene-1,2,4,5,7,8,9,10,11-d9 (10 g, 1 eq) and naphthalen-1-ylboronic acid (3.8 g, 1.1 eq). Recrystallization under toluene conditions yielded compound BH-10-a (7.1 g, 65%).

[0578] Synthesis example 10-2)

[0579] Compound BH-10 was synthesized using the same method as in Synthesis Example 8-2, starting with BH-10-a (7.1 g, 1 eq.) and (9,9-dimethyl-9H-fluoren-4-yl)boronic acid (3.4 g, 1.1 eq). Recrystallization under toluene conditions yielded compound BH-10 (6.1 g, 67%).

[0580] <Experimental Example 1: Device Example>

[0581] <Example 1>

[0582] A glass substrate coated with an ITO (indium tin oxide) film at a thickness of 1400 Å was immersed in distilled water containing a detergent and ultrasonically washed. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the ultrasonic washing was repeated twice with distilled water for 10 minutes each time. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0583] On the ITO transparent electrode prepared as described above, a hole injection layer is formed by thermal vacuum evaporation of the following HT-A and HI-A compounds in a 90:10 (weight ratio) thickness to a thickness of 110 Å. On the hole injection layer, a hole transport layer is formed by vacuum evaporation of the following HT-A to a thickness of 1000 Å. On the hole transport layer, an electron suppression layer is formed by vacuum evaporation of the following HT-B to a thickness of 50 Å. Next, a first light-emitting layer is formed by co-evaporation of the following compound BH-1, which serves as the main body of the first light-emitting layer, and a blue fluorescent dopant BD-1, which serves as the main body of the second light-emitting layer, in a 97:3 (wt%) weight ratio. A second light-emitting layer is formed by co-evaporation of the following compound BH-A, which serves as the main body of the second light-emitting layer, and a blue fluorescent dopant BD-1, in a 97:3 (wt%) weight ratio. The thicknesses of the first and second light-emitting layers are shown in Table 1 below, and the combined thickness of the two light-emitting layers is 200 Å.

[0584] Then, on the second light-emitting layer, as the first electron transport layer, compound ET-A was vacuum-deposited for 50 Å. Next, ET-B and LiQ were vacuum-deposited at a weight ratio of 2:1 to form a second electron transport layer with a thickness of 300 Å. On the second electron transport layer, LiQ was vacuum-deposited to form an electron injection layer with a thickness of 5 Å. On the electron injection layer, aluminum and silver were deposited at a thickness of 220 Å and a weight ratio of 10:1. On top of this, aluminum was deposited to a thickness of 1000 Å to form a cathode.

[0585] During the above process, the evaporation rate of the organic material was maintained at 0.4~0.9 Å / s, and the evaporation rate of the aluminum cathode was maintained at 2 Å / s. The vacuum level was maintained at 1×10⁻⁶ during evaporation. -7 ~5×10 -8 This led to the creation of organic light-emitting devices.

[0586]

[0587]

[0588]

[0589]

[0590]

[0591]

[0592] <Examples 2 to 12>

[0593] In Example 1 above, the host and dopant compounds described in Table 1 below were used instead of the light-emitting layer (first light-emitting layer and second light-emitting layer) materials. Otherwise, the organic light-emitting devices of Examples 2 to 12 were fabricated using the same method as in Example 1.

[0594] <Example 13>

[0595] In Example 1 above, the host and dopant compounds described in Table 1 below were used instead of the light-emitting layer (first light-emitting layer and second light-emitting layer) materials. In particular, as the host of the second light-emitting layer, compounds BH-A and BH-C were used in a 1:1 weight ratio (wt%) to replace compound BH-A for co-evaporation. Otherwise, the organic light-emitting device of Example 13 was fabricated using the same method as in Example 1.

[0596] <Comparative Examples 1 to 6>

[0597] In Example 1 above, the host and dopant compounds described in Table 1 below were used instead of the light-emitting layer (first light-emitting layer and second light-emitting layer) materials. Otherwise, organic light-emitting devices of Comparative Examples 1 to 6 were fabricated using the same method as in Example 1.

[0598] <Comparison of Examples 7 and 8>

[0599] In Example 1 above, the host and dopant compounds described in Table 1 below were used instead of the light-emitting layer (first light-emitting layer and second light-emitting layer) materials. In particular, only the first light-emitting layer (single light-emitting layer) was fabricated with a thickness of 200 Å and no second light-emitting layer was used. Otherwise, the organic light-emitting devices of Comparative Examples 7 and 8 were fabricated using the same method as in Example 1.

[0600] Table 1 below shows the compounds used for the light-emitting layers (first and second light-emitting layers), and the organic light-emitting devices fabricated therefrom are used at 15 mA / cm². 2 The luminous efficiency (cd / A / y) was measured at a current density of 20 mA / cm². 2 The time (T97) at the current density was measured relative to the initial brightness to reach 97%, and the relative value is shown with Comparative Example 1 as the reference.

[0601] Conversion efficiency (cd / A / y) takes into account everything from current efficiency (cd / A) to the color purity of the material (CIEy), and has become an important benchmark value for efficiency in organic light-emitting devices that aim for high brightness and high color reproduction.

[0602]

[0603] According to Table 1 above, it was confirmed that when the anthracene compound was used as the main body of the light-emitting layer in Comparative Examples 7 and 8, the efficiency of the organic light-emitting device increased when the compound of Chemical Formula 1 of this specification was used together.

[0604] When only anthracene compounds are used as the host of the luminescent layer, the region where holes and electrons recombine is the same as the region that actually emits blue light. Therefore, as the exciton density increases, the probability of exciton quenching also increases, thus causing a decrease in efficiency and lifetime. However, when the compound of Formula 1 in this specification is used as the host of the first luminescent layer, and the anthracene compound is used as the host of the second luminescent layer, thus separating the first and second luminescent layers, the blue luminescent region becomes wider compared to the region where holes and electrons recombine.

[0605] In addition, the widening of the luminescent region reduces exciton-exciton quenching and exciton-polaron quenching, which helps to improve efficiency.

[0606] In particular, using anthracene, which has high triplet-triplet-fusion (TTF) efficiency, as the host of the second light-emitting layer, and using α, which has a higher triplet energy than anthracene, as the host of the first light-emitting layer, can alleviate triplet stacking in the main light-emitting region, while TTF can help increase the device's efficiency.

[0607] The experiments in Comparative Examples 1 to 6 demonstrate that the compounds of Chemical Formula 1 in this specification also play a major role in the efficiency and lifetime performance of the devices. Specifically, the organic light-emitting devices of Chemical Formula 1 in this specification, which contain compounds in which π is substituted with deuterium, show a significant improvement in lifetime compared to Comparative Examples 1 to 6, which are either unsubstituted with deuterium or have only deuterium substituted in parts other than π.

[0608] Therefore, it can be confirmed that the organic light-emitting device using chemical formula 1 according to one embodiment of this specification as the main body of the first light-emitting layer has excellent lifetime and efficiency.

[0609] <Experimental Example 2: Triplete State Calculation>

[0610] The following compounds were analyzed using the TD-DFT (B3LYP) method / 6-31G* basis set approach to calculate the HOMO, LUMO, and singlet and triplet energy levels of the absorption states. For the same structure, the calculation results were identical due to the difference between protium and deuterium. The results are consistent with those in Table 2 below.

[0611]

[0612]

[0613] The above experiments confirmed the relative values ​​of the triplet energy levels of anthracene and β, indicating that the T1 of compound C-2 (β) is larger than that of compound C-1 (anthracene).

[0614]

[0615]

[0616] In addition, it can be confirmed that the substance C-3, which contains both anthracene and β, follows the lower T1 value of anthracene.

[0617] The preferred embodiment (light-emitting layer) of the present invention has been described above, but the present invention is not limited thereto. Various modifications can be made within the scope of the claims and the detailed description of the invention, which also fall within the scope of the invention.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, R1, R2, R4, R5 and R7 to R11 are deuterium. R3 and R6 may be the same as or different from each other, and each may be independently deuterium, or substituted or unsubstituted aryl groups. L1 is a directly bonded, substituted, or unsubstituted aryl group. The L1 does not contain substituted or unsubstituted divalent anthracene groups. l1 can be 1 or 2. When l1 is 2, the L1 values ​​can be the same or different from each other. Ar1 is a substituted or unsubstituted aryl group.

2. The compound according to claim 1, wherein, The chemical formula 1 is any one of the following chemical formulas 1-1 to 1-3: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] In the chemical formulas 1-1 to 1-3, The definitions of R1 to R11, L1, and l1 are the same as those in Chemical Formula 1. R101 and R102 may be the same as or different from each other, and each may be an independently substituted or unsubstituted alkyl group. R103 to R110 may be the same as or different from each other, and each can be hydrogen or deuterium independently. r103 is an integer from 1 to 3. When r103 is 2 or more, the two or more r103 values ​​are the same or different from each other. r104 is an integer from 1 to 4. When r104 is 2 or more, the two or more r104 values ​​are the same or different from each other. r110 is an integer from 1 to 7. When r110 is 2 or more, the two or more R110s are the same or different from each other.

3. The compound according to claim 1, wherein, R1, R2, R4, R5, and R7 to R11 are deuterium. The R3 and R6 may be the same as or different from each other, and each may be independently deuterium; or may be a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group with 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or a combination thereof.

4. The compound according to claim 1, wherein, The L1 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms that is directly bonded, or substituted with deuterium or not substituted, and the L1 does not contain substituted or unsubstituted divalent anthracene groups.

5. The compound according to claim 1, wherein, The Ar1 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, substituted or unsubstituted with deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a combination thereof.

6. The compound according to claim 1, wherein, Chemical Formula 1 is any one of the following compounds: 。 7. An organic light-emitting device, wherein, include: anode, cathode, and One or more organic layers are disposed between the anode and the cathode. One or more of the organic layers comprise the compound according to any one of claims 1 to 6.

8. The organic light-emitting device according to claim 7, wherein, The organic layer includes a light-emitting layer, which contains the compound.

9. The organic light-emitting device according to claim 8, wherein, The luminescent layer contains the compound as the main component.

10. The organic light-emitting device according to claim 8, wherein, The light-emitting layer comprises the compound as the main component and also contains dopants.

11. The organic light-emitting device according to claim 10, wherein, The dopant is a compound with the following chemical formula D: [Chemical formula D] In the chemical formula D, X1 and X2 may be the same as or different from each other, and each is independently CR', NR", or O, with at least one of X1 and X2 being NR". A and C may be the same as or different from each other, and each may independently be a substituted or unsubstituted five-membered ring or a substituted or unsubstituted six-membered ring. R401, R', and R" may be the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted fused ring group formed by the fusion of aromatic and aliphatic hydrocarbon rings, or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring formed by combining with adjacent groups. r401 is an integer from 1 to 3. When r401 is 2 or more, the substituents in the parentheses are the same or different from each other.

12. The organic light-emitting device according to claim 8, wherein, The light-emitting layer contains the compound as a first host and also contains a second host.

13. The organic light-emitting device according to claim 12, wherein, The second main component is a compound with the following chemical formula H: [Chemical formula H] In the chemical formula H, L20 and L21 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group. Ar20 and Ar21 may be the same as or different from each other, and each can be independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic. R301 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. r301 is an integer from 1 to 8. When r301 is 2 or more, two or more r301s are the same or different from each other.

14. The organic light-emitting device according to claim 8, wherein, The light-emitting layer comprises the compound as a first host, a second host, and a dopant.

15. An organic light-emitting device, wherein, include: anode, cathode, A first light-emitting layer disposed between the anode and the cathode, and A second light-emitting layer is disposed between the first light-emitting layer and the cathode and is in contact with the first light-emitting layer. The first light-emitting layer comprises the compound according to any one of claims 1 to 6. The second light-emitting layer comprises a compound with the following chemical formula H: [Chemical formula H] In the chemical formula H, L20 and L21 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group. Ar20 and Ar21 may be the same as or different from each other, and each can be independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic. R301 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. r301 is an integer from 1 to 8. When r301 is 2 or more, two or more r301s are the same or different from each other.

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