Compound and organic light-emitting element comprising same

Abstract

The present specification relates to: a compound represented by chemical formula 1 and capable of improving the efficiency and lifespan characteristics of an organic light-emitting element; and an organic light-emitting element comprising an anode, a cathode, and one or more organic material layers provided between the anode and the cathode, wherein at least one of the one or more organic material layers comprises the compound represented by chemical formula 1.

Description

Compound and organic light-emitting device containing the same

[0001] This application claims the benefit of Korean Patent Application No. 10-2024-0071395 filed with the Korean Intellectual Property Office on May 31, 2024, the entire contents of which are incorporated herein by reference.

[0002] The present specification relates to a compound and an organic light-emitting device comprising the same.

[0003] In general, organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light emitting devices that utilize the organic light emitting phenomenon typically have a structure that includes an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and can be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when these excitons fall back to the ground state, light is emitted.

[0004] There is a continuing need for the development of new materials for organic light-emitting devices such as the above.

[0005] The present specification provides a compound and an organic light-emitting device comprising the same.

[0006] One embodiment of the present specification provides a compound of the following chemical formula 1.

[0007] [Chemical Formula 1]

[0008]

[0009] In the above chemical formula 1,

[0010] At least one of R1 to R12 is the following chemical formula 2, and the rest of R1 to R12 that are not the following chemical formula 2 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0011] [Chemical Formula 2]

[0012]

[0013] In the above chemical formula 2,

[0014] Y1 is O or S,

[0015] L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0016] l1 is 1 or 2, and if l1 is 2, L1 are equal to or different from each other,

[0017] G1 to G3 are the same or different and are each independently hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrene group substituted or unsubstituted with deuterium; or a heteroaryl group having 5 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0018] g1 to g3 are integers from 1 to 4, respectively,

[0019] If the above g1 is 2 or more, the two or more G1 are equal to or different from each other,

[0020] If the above g2 is 2 or more, the above 2 or more G2 are equal to or different from each other,

[0021] If the above g3 is 2 or more, the two or more G3 are equal to or different from each other,

[0022] m is 0 or 1,

[0023] If the above m is 0, the above g2 is an integer from 1 to 4, and g1+g2≤7,

[0024] If the above m is 1, the above g2 is 1 or 2, and g1+g2+g3≤9,

[0025] is a portion that is bonded to the above chemical formula 1,

[0026] The above chemical formula 1 contains at least one deuterium.

[0027] In addition, one embodiment of the present specification provides an organic light-emitting device comprising an anode; a cathode; and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers comprises a compound of the chemical formula 1.

[0028] In addition, one embodiment of the present specification provides an organic light-emitting device including an anode; a cathode; a first light-emitting layer provided between the anode and the cathode; and a second light-emitting layer provided between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, wherein the first light-emitting layer includes a compound of the chemical formula 1, and the second light-emitting layer includes a compound of the chemical formula H below.

[0029] [Chemical formula H]

[0030]

[0031] In the above chemical formula H,

[0032] L20 and L21 are the same or different, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0033] Ar20 and Ar21 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0034] 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,

[0035] r301 is an integer from 1 to 8, and when r301 is 2 or more, 2 or more R301 are the same as or different from each other.

[0036] The compound described herein can be used as a material for an organic layer of an organic light-emitting device. Conventionally used anthracene compounds use TTF (triplet-triplet fusion) as the main light-emitting mechanism, and an organic light-emitting device that uses an anthracene compound as a host for the light-emitting layer has the same region where holes and electrons combine (recombination zone) and the region that emits light (emission zone). When the compound of Chemical Formula 1 of the present specification, which has a higher triplet energy than the anthracene compound, is used as a host together with a second host having a lower triplet energy, holes and electrons combine in the compound to form excitons, and the singlet participates in light emission as it is, and the triplet is transferred in the form of a dexter energy to the second host having a lower value, and the anthracene compound or other second host that has received the triplet emits light in the form of a TTF. This can improve the efficiency and lifespan characteristics of the organic light-emitting device.

[0037] Figures 1 to 4 illustrate examples of the structure of an organic light-emitting device according to one embodiment of the present specification.

[0038] Figure 5 is an MS graph of compound A.

[0039] [Explanation of symbols]

[0040] 1: Substrate

[0041] 2: Anode

[0042] 3: Hole injection layer

[0043] 4: Hole transport layer

[0044] 34: Hole injection and transport layer

[0045] 5: Hole blocking layer

[0046] 6: Emissive layer

[0047] 6-1: First light-emitting layer

[0048] 6-2: Second light-emitting layer

[0049] 7: Electron blocking layer

[0050] 8: Electron transport layer

[0051] 9: Electron injection layer

[0052] 10: Cathode

[0053] The following describes this specification in more detail.

[0054] Chemical formula 1 according to one embodiment of the present specification is a compound in which chemical formula 2 is bonded to a specific position of the chrysene core, and the triplet energy level (T) of the substituent bonded to chemical formula 2 and chrysene s 1) A compound having a triplet energy level higher than that of Chrysene, or a triplet energy level (T) of a substituent bonded to the chemical formula 2 and Chrysene s 1) is below the triplet energy level, and the above T s 1 is a compound having a difference from the triplet energy level of chrysene of more than 0 eV and less than 0.2 eV. The compound of the above chemical formula 1 has a higher triplet energy than the anthracene compound used in the past, and thus transfers the triplet energy to the second host used together, thereby reducing triplet quenching of the compound compared to when the second host (anthracene compound) is used alone, thereby improving efficiency and lifespan characteristics in organic light-emitting devices.

[0055] The above chemical formula 1 contains at least one deuterium.

[0056] According to one embodiment of the present specification, the physicochemical properties such as chemical bond length related to deuterium are different from those of hydrogen, and the elongation amplitude of the CD bond is smaller than that of the C-H bond, so the van der Waals radius of deuterium is smaller than that of hydrogen, and in general, the C-D bond can be shown to be shorter and stronger than the C-H bond. Therefore, when the chemical formula 1 includes deuterium as a substituent, the energy of the ground state is lowered, and as the bond length of deuterium and carbon is shortened, the molecular hardcore volume is reduced, and accordingly, the electrical polarizability can be reduced, and by weakening the intermolecular interaction, the thin film volume can be increased. In addition, these characteristics can have the effect of lowering the crystallinity of the thin film, that is, creating an amorphous state, and can generally be effective in increasing the lifespan and operating characteristics of an organic light-emitting device, and the heat resistance can be improved compared to a conventional organic light-emitting device.

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

[0058] In this specification, means the connecting part.

[0059] Throughout this specification, the term "combination thereof" included in the expressions in the Makushi format means one or more mixtures or combinations selected from the group consisting of the components described in the expressions in the Makushi format, and means including one or more selected from the group consisting of said components.

[0060] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where the hydrogen atom is replaced, i.e., a position where the substituent can be replaced, and when two or more are replaced, the two or more substituents may be the same or different from each other.

[0061] The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; halogen group; cyano group; alkyl group; cycloalkyl group; alkoxy group; alkenyl group; haloalkyl group; silyl group; aryl group; condensed ring group of aromatic hydrocarbon ring and aliphatic hydrocarbon ring; and heteroaryl group, or substituted with a substituent in which two or more substituents among the above-mentioned substituents are linked, or having no substituents.

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

[0063] In this specification, examples of halogen groups include a fluoro group, a chloro group, a bromo group, or an iodo group.

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

[0065] In the present specification, the cycloalkyl group is not particularly limited, but is preferably one having 3 to 30 carbon atoms, and specifically, includes, but is not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like.

[0066] In the present specification, the alkoxy group may be linear, branched, or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, an n-pentyloxy group, a neopentyloxy group, an isopentyloxy group, an n-hexyloxy group, a 3,3-dimethylbutyloxy group, a 2-ethylbutyloxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

[0067] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group.

[0068] In this specification, a haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the above alkyl group.

[0069] In the present specification, the aryl group is not particularly limited, but is preferably one having 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0070] When the above aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may include, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc.

[0071] When the above aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may include, but is not limited to, a naphthyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, phenalene group, perylene group, chrysene group, fluorene group, etc.

[0072] In the present specification, the fluorene group may be substituted, and adjacent groups may be combined with each other to form a ring.

[0073] Examples of the above fluorene group include

[0074] There are, but are not limited to, the following.

[0075] In this specification, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent that is sterically closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.

[0076] In the present specification, a heteroaryl group includes one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine, phenanthroline, isoxazole group, thiadiazole group, Examples thereof include, but are not limited to, dibenzofuran group, dibenzosilole group, phenoxathiine group, phenoxazine group, phenothiazine group, dihydroindenocarbazole group, spirofluorenxanthene group, and spirofluorenethioxanthene group.

[0077] In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, etc. Among the alkylsilyl groups, the alkyl group may be applied with the examples of the alkyl group described above, among the arylsilyl groups, the aryl group may be applied with the examples of the aryl group described above, and among the heteroarylsilyl groups, the heteroaryl group may be applied with the examples of the heteroaryl group described above.

[0078] In the present specification, the hydrocarbon ring group may be an aromatic hydrocarbon ring group; an aliphatic hydrocarbon ring group; or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring. The description of the above-described aryl group may be applied to the aromatic hydrocarbon ring group, and the description of the above-described cycloalkyl group may be applied to the aliphatic hydrocarbon ring group. In addition, the condensed ring group of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring may have a structure in which the above-described aryl group and the cycloalkyl group are condensed with each other.

[0079] In the present specification, the heterocyclic group may be an aromatic heterocyclic group; an aliphatic heterocyclic group; or a condensed ring group of an aromatic heterocyclic group and an aliphatic heterocyclic group, and the description of the above-described heteroaryl group may be applied to the aromatic heterocyclic group.

[0080] In this specification, an arylene group means a divalent group having two bonding positions to an aryl group. The description of the aryl group described above may be applied to these groups, except that each is a divalent group.

[0081] In this specification, a heteroarylene group means a divalent group having two bonding positions to a heteroaryl group. The description of the heteroaryl group described above may be applied to these groups, except that each is a divalent group.

[0082] In the present specification, a five-membered ring means a ring including a five-membered ring in the aforementioned hydrocarbon ring group, heterocyclic group, or condensed structure thereof, except that it is not a single ring.

[0083] In the present specification, the description of a substituent including a 6-membered ring in the above-mentioned aryl group, heteroaryl group, cycloalkyl group, or combinations thereof may be applied, except that the 6-membered ring is not monovalent.

[0084] In this specification, “more than” means equal to or greater than (higher than or more than) a reference quantity, value, range, etc., “less than” means equal to or less than (lower than or less than) a reference quantity, value, range, etc., “exceeds” means greater than (higher than or more than) a reference quantity, value, range, etc., and “less than” means less than (lower than or less than) a reference quantity, value, range, etc.

[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 to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, and in case of conflict, this specification, including definitions, will control unless a specific passage is cited. Furthermore, the materials, methods, and examples are illustrative only and not intended to be limiting.

[0086] Hereinafter, the compound of the above chemical formula 1 will be described in detail.

[0087] According to one embodiment of the present specification, in the chemical formula 1, the triplet energy level (T1) of the substituted or unsubstituted aryl group; the substituted or unsubstituted heteroaryl group; the substituted or unsubstituted arylene group; the substituted or unsubstituted heteroarylene group; and the chemical formula 2 is equal to or higher than the triplet energy level of Chrysene.

[0088] According to one embodiment of the present specification, in the chemical formulas 1 and 2, the substituted or unsubstituted aryl group; the substituted or unsubstituted heteroaryl group; the substituted or unsubstituted arylene group; and the triplet energy level (T) of the substituted or unsubstituted heteroarylene group s 1) is above the triplet energy level of Chrysene.

[0089] According to one embodiment of the present specification, in the chemical formula 1, the substituted or unsubstituted aryl group; the substituted or unsubstituted heteroaryl group; the substituted or unsubstituted monocyclic or polycyclic arylene group; the substituted or unsubstituted monocyclic or polycyclic heteroarylene group; and the triplet energy level (T) of the chemical formula 2 s 1) is above the triplet energy level of Chrysene.

[0090] According to one embodiment of the present specification, in the chemical formulas 1 and 2, the substituted or unsubstituted aryl group; the substituted or unsubstituted heteroaryl group; the substituted or unsubstituted monocyclic or polycyclic arylene group; and the triplet energy level (T) of the substituted or unsubstituted monocyclic or polycyclic heteroarylene group s 1) is above the triplet energy level of Chrysene.

[0091] According to one embodiment of the present specification, in the chemical formula 1, the substituted or unsubstituted aryl group having 6 to 30 carbon atoms; the substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; the substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; the substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms; and the triplet energy level (T) of the chemical formula 2 s 1) is above the triplet energy level of Chrysene.

[0092] According to one embodiment of the present specification, in the chemical formulae 1 and 2, the substituted or unsubstituted aryl group having 6 to 30 carbon atoms; the substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; the substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; and the triplet energy level (T) of the substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms s 1) is above the triplet energy level of Chrysene.

[0093] That is, the triplet energy level (T) of the substituents excluding hydrogen and deuterium among the definitions of R1 to R12, L1, G1, G2 and G3 of the above chemical formulas 1 and 2 s 1) means that it is above the triplet energy level of Chrysene.

[0094] The triplet energy level of the core of the chemical formula 1 according to one embodiment of the present specification is 2.5 eV.

[0095] According to one embodiment of the present specification, in the chemical formulas 1 and 2, the substituted or unsubstituted aryl group; the substituted or unsubstituted heteroaryl group; the substituted or unsubstituted arylene group; and the triplet energy level (T) of the substituted or unsubstituted heteroarylene group s 1) is 2.5 eV or more.

[0096] That is, the triplet energy level (T) of the substituents excluding deuterium and deuterium defined in R1 to R12, L1, G1, G2 and G3 of the above chemical formulas 1 and 2 s 1) is 2.5 eV or more.

[0097] According to one embodiment of the present specification, in the chemical formulas 1 and 2, the substituted or unsubstituted aryl group; the substituted or unsubstituted heteroaryl group; the substituted or unsubstituted arylene group; and the triplet energy level (T) of the substituted or unsubstituted heteroarylene group s 1) is below the triplet energy level of Chrysen, and the above Ts 1 is the difference from the triplet energy level of Chrysen is more than 0 eV and less than or equal to 0.2 eV. Or the above T s 1 is the difference from the triplet energy level of Chrysen by more than 0 eV and less than 0.1 eV.

[0098] According to one embodiment of the present specification, in the chemical formula 1, the substituted or unsubstituted aryl group; the substituted or unsubstituted heteroaryl group; the substituted or unsubstituted monocyclic or polycyclic arylene group; the substituted or unsubstituted monocyclic or polycyclic heteroarylene group; and the triplet energy level (T) of the chemical formula 2 s 1) is below the triplet energy level of Chrysen, and the above T s 1 is the difference from the triplet energy level of Chrysen is more than 0 eV and less than or equal to 0.2 eV. Or the above T s 1 is the difference from the triplet energy level of Chrysen by more than 0 eV and less than 0.1 eV.

[0099] According to one embodiment of the present specification, in the chemical formulas 1 and 2, the substituted or unsubstituted aryl group; the substituted or unsubstituted heteroaryl group; the substituted or unsubstituted monocyclic or polycyclic arylene group; and the triplet energy level (T) of the substituted or unsubstituted monocyclic or polycyclic heteroarylene group s 1) is below the triplet energy level of Chrysen, and the above T s 1 is the difference from the triplet energy level of Chrysen is more than 0 eV and less than or equal to 0.2 eV. Or the above T s 1 is the difference from the triplet energy level of Chrysen by more than 0 eV and less than 0.1 eV.

[0100] According to one embodiment of the present specification, in the chemical formula 1, the substituted or unsubstituted aryl group having 6 to 30 carbon atoms; the substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; the substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; the substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms; and the triplet energy level (T) of the chemical formula 2 s 1) is below the triplet energy level of Chrysen, and the above T s 1 is the difference from the triplet energy level of Chrysen is more than 0 eV and less than or equal to 0.2 eV. Or the above T s 1 is the difference from the triplet energy level of Chrysen by more than 0 eV and less than 0.1 eV.

[0101] According to one embodiment of the present specification, in the chemical formulae 1 and 2, the substituted or unsubstituted aryl group having 6 to 30 carbon atoms; the substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; the substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; and the triplet energy level (T) of the substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms s 1) is below the triplet energy level of Chrysen, and the above T s 1 is the difference from the triplet energy level of Chrysen is more than 0 eV and less than or equal to 0.2 eV. Or the above T s 1 is the difference from the triplet energy level of Chrysen by more than 0 eV and less than 0.1 eV.

[0102] That is, the triplet energy level (T) of the substituents excluding deuterium and deuterium defined in R1 to R12, L1, G1, G2 and G3 of the above chemical formulas 1 and 2 s 1) is below the triplet energy level of Chrysen, and the above T s1 means that the difference from the triplet energy level of Chrysen is greater than 0 eV and less than or equal to 0.2 eV, or greater than 0 eV and less than or equal to 0.1 eV.

[0103] The above T s 1 is a value similar to the triplet energy level of Chrysen, which is greater than 0 eV and less than 0.2 eV from the triplet energy level of Chrysen, and T s It has an effect equivalent to that of a triplet energy level higher than that of the 1st Chrysene.

[0104] According to one embodiment of the present specification, in the chemical formulas 1 and 2, the substituted or unsubstituted aryl group; the substituted or unsubstituted heteroaryl group; the substituted or unsubstituted arylene group; and the triplet energy level (T) of the substituted or unsubstituted heteroarylene group s 1) is similar to or higher than the triplet energy level of Chrysene.

[0105] The above similarity means T s This may mean that the difference between the triplet energy levels of 1 and Chrysen is greater than 0 eV and less than 0.2 eV.

[0106] In this specification, energy level refers to the magnitude of energy. Therefore, even when an energy level is indicated in a negative direction from the vacuum level, the energy level is interpreted to refer to the absolute value of the corresponding energy value. For example, a low or deep energy level means that the absolute value increases in the negative direction from the vacuum level.

[0107] In this specification, triplet energy can be measured using a method known in the art, and specifically, it was measured at 77 K using a commercially available device, JASCO FP-8600. The measurement of triplet energy is performed as follows. First, a sample is prepared by sealing a solution in which a compound to be measured is dissolved in an appropriate solvent in a quartz glass tube. For this sample, a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 K), and a tangent is drawn to the beginning of the short-wavelength side of this phosphorescence spectrum, and the wavelength value λ of the intersection of the tangent and the horizontal axis is determined. edge The triplet energy was calculated by substituting it into the conversion formula below based on (nm).

[0108] Conversion formula: T1(eV) = 1239.85 / λ edge

[0109] According to one embodiment of the present specification, the compound of the chemical formula 1 has a triplet energy level (T1) of 2.3 eV or more. In addition, the compound of the chemical formula 1 has a triplet energy level (T1) of 2.35 eV or more, 2.37 eV or more, 2.4 eV or more, or 2.41 eV or more, or 2.5 eV or more.

[0110] According to one embodiment of the present specification, the m is 0.

[0111] According to one embodiment of the present specification, m is 1.

[0112] According to one embodiment of the present specification, the chemical formula 2 is the following chemical formula 2-A or 2-B.

[0113] [Chemical Formula 2-A]

[0114]

[0115] [Chemical Formula 2-B]

[0116]

[0117] In the above chemical formulas 2-A and 2-B,

[0118] The definitions of Y1, L1, l1, G1 to G3 and g1 to g3 are the same as those defined in the above chemical formula 2.

[0119] According to one embodiment of the present specification, the chemical formula 2 is any one of the following chemical formulas 2-1 to 2-7.

[0120] [Chemical Formula 2-1]

[0121]

[0122] [Chemical Formula 2-2]

[0123]

[0124] [Chemical Formula 2-3]

[0125]

[0126] [Chemical Formula 2-4]

[0127]

[0128] [Chemical Formula 2-5]

[0129]

[0130] [Chemical Formula 2-6]

[0131]

[0132] [Chemical Formula 2-7]

[0133]

[0134] In the above chemical formulas 2-1 to 2-7,

[0135] The definitions of Y1, L1, l1, G1 to G3 and g1 to g3 are the same as those defined in the above chemical formula 2.

[0136] According to one embodiment of the present specification, the Y1 is O.

[0137] According to one embodiment of the present specification, the Y1 is S.

[0138] According to one embodiment of the present specification, the chemical formula 2 is any one of the following chemical formulas 2-8 to 2-14.

[0139] [Chemical Formula 2-8]

[0140]

[0141] [Chemical Formula 2-9]

[0142]

[0143] [Chemical Formula 2-10]

[0144]

[0145] [Chemical Formula 2-11]

[0146]

[0147] [Chemical Formula 2-12]

[0148]

[0149] [Chemical Formula 2-13]

[0150]

[0151] [Chemical Formula 2-14]

[0152]

[0153] In the above chemical formulas 2-8 to 2-14,

[0154] The definitions of L1, l1, G1 to G3 and g1 to g3 are the same as those defined in the above chemical formula 2.

[0155] According to one embodiment of the present specification, the chemical formula 2 is any one of the following chemical formulas 2-15 to 2-21.

[0156] [Chemical Formula 2-15]

[0157]

[0158] [Chemical Formula 2-16]

[0159]

[0160] [Chemical Formula 2-17]

[0161]

[0162] [Chemical Formula 2-18]

[0163]

[0164] [Chemical Formula 2-19]

[0165]

[0166] [Chemical Formula 2-20]

[0167]

[0168] [Chemical Formula 2-21]

[0169]

[0170] In the above chemical formulas 2-15 to 2-21,

[0171] The definitions of L1, l1, G1 to G3 and g1 to g3 are the same as those defined in the above chemical formula 2.

[0172] According to one embodiment of the present specification, at least one of R1 to R4, R6 to R10 and R12 is the chemical formula 2.

[0173] According to one embodiment of the present specification, any one of R1 to R4, R6 to R10 and R12 is the chemical formula 2.

[0174] According to one embodiment of the present specification, any two of R1 to R4, R6 to R10 and R12 are the chemical formula 2.

[0175] According to one embodiment of the present specification, any three of R1 to R4, R6 to R10 and R12 are of the chemical formula 2.

[0176] According to one embodiment of the present specification, R1 is the chemical formula 2.

[0177] According to one embodiment of the present specification, R2 is the chemical formula 2.

[0178] According to one embodiment of the present specification, R3 is the chemical formula 2.

[0179] According to one embodiment of the present specification, R6 is the chemical formula 2.

[0180] According to one embodiment of the present specification, R12 is the chemical formula 2.

[0181] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other and are each independently the chemical formula 2.

[0182] According to one embodiment of the present specification, R1 and R3 are the same as or different from each other and are each independently the chemical formula 2.

[0183] According to one embodiment of the present specification, R1 and R6 are the same as or different from each other and are each independently the chemical formula 2.

[0184] According to one embodiment of the present specification, R1 and R12 are the same as or different from each other and are each independently the chemical formula 2.

[0185] According to one embodiment of the present specification, R2 and R3 are the same as or different from each other and are each independently the chemical formula 2.

[0186] According to one embodiment of the present specification, R2 and R6 are the same as or different from each other and are each independently the chemical formula 2.

[0187] According to one embodiment of the present specification, R2 and R12 are the same as or different from each other and are each independently the chemical formula 2.

[0188] According to one embodiment of the present specification, R3 and R6 are the same as or different from each other and are each independently the chemical formula 2.

[0189] According to one embodiment of the present specification, R3 and R12 are the same as or different from each other and are each independently the chemical formula 2.

[0190] According to one embodiment of the present specification, R6 and R12 are the same as or different from each other and are each independently the chemical formula 2.

[0191] According to one embodiment of the present specification, R1 to R3 are the same as or different from each other and are each independently the chemical formula 2.

[0192] According to one embodiment of the present specification, R1, R2 and R6 are the same as or different from each other and are each independently the chemical formula 2.

[0193] According to one embodiment of the present specification, R1, R3 and R6 are the same as or different from each other and are each independently the chemical formula 2.

[0194] According to one embodiment of the present specification, R2, R3 and R6 are the same as or different from each other and are each independently the chemical formula 2.

[0195] According to one embodiment of the present specification, R1 to R3 and R6 are the same as or different from each other and are each independently the chemical formula 2.

[0196] According to one embodiment of the present specification, the chemical formula 1 is any one of the following chemical formulas 1-1 to 1-6.

[0197] [Chemical Formula 1-1]

[0198]

[0199] [Chemical Formula 1-2]

[0200]

[0201] [Chemical Formula 1-3]

[0202]

[0203] [Chemical Formula 1-4]

[0204]

[0205] [Chemical Formula 1-5]

[0206]

[0207] [Chemical Formula 1-6]

[0208]

[0209] In the above chemical formulas 1-1 to 1-6,

[0210] The definitions of Y1, L1, l1, G1 to G3 and g1 to g3 are the same as those defined in the above chemical formula 2,

[0211] R1 to R12 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0212] Y11 is O or S,

[0213] L11 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0214] l11 is 1 or 2, and if l11 is 2, L11 are equal to or different from each other,

[0215] G11 to G13 are the same as or different from each other, and each independently represent hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrene group substituted or unsubstituted with deuterium; or a heteroaryl group having 5 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0216] g11 to g113 are integers from 1 to 4, respectively,

[0217] If the above g11 is 2 or more, the two or more G11 are the same or different from each other,

[0218] If the above g12 is 2 or more, the two or more G12 are the same or different from each other,

[0219] If the above g13 is 2 or more, the two or more G13 are the same or different from each other,

[0220] m' is 0 or 1,

[0221] If the above m' is 0, the above g12 is an integer from 1 to 4, and g11+g12≤7,

[0222] If the above m' is 1, the above g12 is 1 or 2, and g11+g12+g13≤9.

[0223] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 1% or more.

[0224] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 2% or more.

[0225] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 10% or more.

[0226] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 15% or more.

[0227] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 1% to 100%.

[0228] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 2% to 100%.

[0229] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 10% to 100%.

[0230] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 15% to 100%.

[0231] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 1% to 99.9%.

[0232] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 2% to 99.9%.

[0233] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 10% to 99.9%.

[0234] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 15% to 99.9%.

[0235] As used herein, “containing deuterium,” “deuterated,” or “deuterated” means that a hydrogen at a substitutable position of a compound is replaced with deuterium.

[0236] As used herein, “perdeuterated” means a compound or group in which all hydrogens in the molecule are replaced with deuterium, and has the same meaning as “100% deuterated.”

[0237] In the present specification, "X% deuterated", "degree of deuteration X%", or "deuterium substitution rate X%" means that X% of the hydrogens at substitutable positions in the structure are replaced with deuterium. For example, when the structure is dibenzofuran, the dibenzofuran is "25% deuterated", the dibenzofuran has a "degree of deuteration 25%", or the dibenzofuran has a "deuterium substitution rate 25%" may mean that 2 of the 8 hydrogens at the substitutable positions of the dibenzofuran are replaced with deuterium, or may also mean that all 8 of the 8 hydrogens at the substitutable positions are replaced with 25% deuterium, or that 4 of the 8 hydrogens at the substitutable positions are replaced with 50% deuterium.

[0238] In this specification, the substituted deuterium has a substitution rate of 1% or more and 99.9% or less.

[0239] In this specification, "degree of deuteration" or "deuterium substitution rate" refers to the degree of deuteration as measured by nuclear magnetic resonance spectroscopy ( 1It can be confirmed by known methods such as H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry).

[0240] Specifically, nuclear magnetic resonance spectroscopy ( 1 When analyzing the "degree of deuteration" or "deuterium substitution rate" by H NMR, add DMF (dimethylformamide) as an internal standard. 1 Through the integration ratio on H NMR, the degree of deuteration or deuterium substitution can be calculated from the total peak integration amount.

[0241] In addition, when analyzing the "degree of deuteration" or "deuterium substitution rate" through TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), the substitution rate can be calculated based on the maximum value (median value) of the distribution of molecular weights at the end of the reaction. For example, when analyzing the degree of deuteration of the following compound A, when the molecular weight of the following starting material is 506 and the maximum value (median value) of the molecular weight of the following compound A is 527 in the MS graph of FIG. 5, since 21 of the hydrogens (26) at the substitutable positions of the following starting material were substituted with deuterium, it can be calculated that approximately 81% of the hydrogens were deuterated.

[0242]

[0243] [Starting material] [Compound A]

[0244] In this specification, D means deuterium.

[0245] According to one embodiment of the present specification, at least one of R1 to R12 is the chemical formula 2, and the remaining R1 to R12 that are not the chemical formula 2 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[0246] According to one embodiment of the present specification, at least one of R1 to R12 is the chemical formula 2, and the remaining R1 to R12 that are not the chemical formula 2 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0247] According to one embodiment of the present specification, at least one of R1 to R12 is the chemical formula 2, and the remaining R1 to R12 that are not the chemical formula 2 are the same as or different from each other, and are each independently hydrogen; deuterium; deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a combination thereof.

[0248] According to one embodiment of the present specification, at least one of R1 to R12 is the chemical formula 2, and the rest of R1 to R12 that are not the chemical formula 2 are the same as or different from each other, and are each independently hydrogen; deuterium; or a phenyl group unsubstituted or substituted with deuterium, a phenyl group, a biphenyl group, a naphthyl group, or a combination thereof; a biphenyl group unsubstituted or substituted with deuterium, a phenyl group, or a combination thereof; a terphenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium, a phenyl group, a naphthyl group, or a combination thereof; or a phenanthrene group unsubstituted or substituted with deuterium.

[0249] According to one embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted arylene group.

[0250] According to one embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group.

[0251] According to one embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted monocyclic arylene group; or a substituted or unsubstituted polycyclic heteroarylene group.

[0252] According to one embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0253] According to one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

[0254] According to one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted monocyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted polycyclic heteroarylene group having 2 to 30 carbon atoms.

[0255] According to one embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group containing O or S.

[0256] According to one embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted monocyclic arylene group; or a substituted or unsubstituted polycyclic heteroarylene group containing O or S.

[0257] According to one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms and containing O or S.

[0258] According to one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted monocyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted polycyclic heteroarylene group having 2 to 30 carbon atoms, including O or S.

[0259] According to one embodiment of the present specification, L1 is a direct bond; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0260] According to one embodiment of the present specification, L1 is a direct bond; or a monocyclic arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0261] According to one embodiment of the present specification, the L1 is a direct bond; a phenylene group unsubstituted or substituted with deuterium, a biphenyl group, a naphthyl group, or a combination thereof; a biphenylylene group unsubstituted or substituted with deuterium, a phenyl group, or a combination thereof; or a terphenylylene group unsubstituted or substituted with deuterium.

[0262] According to one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrene group substituted or unsubstituted with deuterium; or a heteroaryl group having 5 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0263] According to one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrene group substituted or unsubstituted with deuterium; or a monocyclic to pentacyclic heteroaryl group having 5 to 20 carbon atoms and substituted or unsubstituted with deuterium.

[0264] According to one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrene group substituted or unsubstituted with deuterium; a benzofuran group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a benzothiophene group substituted or unsubstituted with deuterium; or a dibenzothiophene group substituted or unsubstituted with deuterium.

[0265] According to one embodiment of the present specification, the chemical formula 1 is any one of the following compounds.

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282] The compound of chemical formula 1 according to one embodiment of the present specification can have a core structure manufactured by a method similar to the manufacturing example described below. Other substituents can be combined by a method known in the art, and the type, position, or number of substituents can be changed according to a technique known in the art.

[0283] In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above chemical formula 1. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can also be controlled by introducing various substituents into the core structure of the above structure.

[0284] In addition, the present specification provides an organic light-emitting device comprising the compound described above.

[0285] When it is said in this specification that a member is located "on" another member, this includes not only cases where the member is in contact with the other member, but also cases where another member exists between the two members.

[0286] When a part in this specification is said to "include" a certain component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

[0287] In this specification, the term "layer" is interchangeable with the term "film", which is commonly used in the present technical field, and refers to a coating covering a target area. The size of the "layer" is not limited, and each "layer" may have the same or different sizes. According to one embodiment, the size of the "layer" may be the same as the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.

[0288] In this specification, the meaning of a specific A material being included in a B layer includes both i) one or more A materials being included in one B layer and ii) the B layer being composed of one or more layers and the A material being included in one or more layers of the multiple B layers.

[0289] In this specification, the meaning that a specific A material is included in a C layer or a D layer means that i) the A material is included in at least one layer among at least one C layer, ii) the A material is included in at least one layer among at least one D layer, or iii) the A material is included in at least one C layer and at least one D layer, respectively.

[0290] An organic light-emitting device according to the present specification is an organic light-emitting device comprising an anode; a cathode; and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers comprises a compound represented by the above-described chemical formula 1.

[0291] The organic light-emitting device of the present specification can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that an organic layer is formed using the compound of the above-described chemical formula 1.

[0292] The above compound can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0293] The organic layer of the organic light-emitting device of the present specification may be formed as a single-layer structure, but may be formed as a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including at least one layer of a hole transport layer, a hole injection layer, an electron blocking (hole control) layer, a hole transport and injection layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking (electron control), and an electron transport and injection layer as the organic layer. However, the structure of the organic light-emitting device of the present specification is not limited thereto and may include a smaller or larger number of organic layers.

[0294] At this time, the light-emitting layer includes the above-described compound as a host for the light-emitting layer, and may include an additional host and dopant. The additional host may be included together with the organic layer including the above-described compound, or may be included in another adjacent organic layer.

[0295] In the organic light-emitting device of the present invention, the light-emitting layer may include an additional host and a dopant, and the total host and dopant may be included in a weight ratio of 99:1 to 1:99, preferably a weight ratio of 99:1 to 70:30, and more preferably a weight ratio of 99:1 to 85:15.

[0296] The light-emitting layer according to one embodiment of the present specification is a blue light-emitting layer, and the maximum light-emitting wavelength is 440 nm to 480 nm.

[0297] The organic light-emitting device of the present specification may further include at least one organic layer among a hole transport layer, a hole injection layer, an electron blocking (hole control) layer, an electron injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking (electron control) layer, and a hole injection and transport layer.

[0298] In one embodiment of the present specification, the organic light-emitting device includes an anode; a cathode; and two or more organic layers provided between the anode and the cathode, and at least one of the two or more organic layers includes a compound represented by the chemical formula 1.

[0299] In one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0300] In one embodiment of the present specification, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0301] The structure of the organic light-emitting device of this specification may have a structure as shown in FIGS. 1 to 4, but is not limited thereto.

[0302] Figure 1 illustrates the structure 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 laminated. In such a structure, the compound may be included in the light-emitting layer (6).

[0303] Figure 2 illustrates the structure of an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking (hole control) layer (5), a light-emitting layer (6), a hole blocking (electron control) layer (7), an electron transport layer (8), an electron injection layer (9), and a cathode (10) are sequentially laminated. In such a structure, the compound may be included in the light-emitting layer (6).

[0304] Figure 3 illustrates the structure 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 sequentially laminated. In such a structure, the compound may be included in the light-emitting layer (6).

[0305] Figure 4 illustrates the structure 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 sequentially laminated. In such a structure, the compound may be included in the first light-emitting layer (6-1).

[0306] In one embodiment of the present specification, the electron transport layer is at least one layer, and when the electron transport layer is two layers, it includes a first electron transport layer and a second electron transport layer, and the first electron transport layer is provided in contact with the second light-emitting layer, and the second electron transport layer is provided thereon, that is, the first electron transport layer can be provided between the second light-emitting layer and the second electron transport layer.

[0307] In one embodiment of the present specification, the electron-blocking (hole-controlling) layer and the light-emitting layer may be provided adjacently. For example, the electron-blocking (hole-controlling) layer and the light-emitting layer may be provided in physical contact.

[0308] In one embodiment of the present specification, the hole transport layer and the electron blocking (hole control) layer may be provided adjacently. For example, the hole transport layer and the electron blocking (hole control) layer may be provided in physical contact.

[0309] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that at least one of the organic layers includes the compound, i.e., the compound of the chemical formula 1.

[0310] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0311] For example, the organic light-emitting device according to the present specification can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, forming an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking (hole control) layer, an electron transport layer, and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0312] In addition, when the organic layer of the organic light-emitting device includes two or more compounds, it can be deposited using a co-deposition or pre-mix method.

[0313] The above organic layer may further include at least one layer among a hole transport layer, a hole injection layer, an electron blocking (hole control) layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking (electron control) layer, and a hole injection and transport layer.

[0314] The above organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking (hole control) layer, a light emitting layer, and an electron transport layer, an electron injection layer, an electron injection and transport layer, etc., but is not limited thereto and may have a single layer structure. In addition, the above organic layer may be manufactured with a smaller number of layers using various polymer materials by a solvent process other than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0315] The anode is an electrode that injects holes, and as the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

[0316] The above cathode is an electrode that injects electrons, and the cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0317] The above hole injection layer can play a role in facilitating hole injection from the anode to the light-emitting layer. The hole injection material is a material that can well inject holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrines, oligothiophenes, arylamine compounds, hexanitrilehexaazatriphenylene compounds, quinacridone compounds, perylene compounds, benzonitrile compounds, anthraquinones, and conductive polymers such as polyaniline and polythiophene. Specifically, the hole injection layer can use an arylamine compound and a benzonitrile compound.

[0318] In the organic light-emitting device of the present specification, the hole injection layer may be formed using an arylamine compound substituted with a carbazole group and a benzonitrile compound substituted with a halogen group, but is not limited thereto.

[0319] According to one embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following chemical formula HI-1.

[0320] [Chemical formula HI-1]

[0321]

[0322] In the above chemical formula HI-1,

[0323] R315 to R317 are the same or different, and each independently represent one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0324] r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 are the same as or different from each other,

[0325] r316 is an integer from 1 to 5, and when r316 is 2 or more, two or more R316 are the same as or different from each other.

[0326] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof.

[0327] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; a triphenylene group; and combinations thereof.

[0328] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, or combine with an adjacent group to form an aryl group or an aromatic hydrocarbon ring substituted with an alkyl group.

[0329] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a phenyl group or a biphenyl group, or combine with an adjacent group to form an indene substituted with a phenyl group or a methyl group.

[0330] According to one embodiment of the present specification, the chemical formula HI-1 is represented by any one of the following compounds.

[0331]

[0332] According to one embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following chemical formula HI-2.

[0333] [Chemical formula HI-2]

[0334]

[0335] In the above chemical formula HI-2,

[0336] R411 to R413 are the same as or mentioned above, and each independently represents a halogen group,

[0337] r411 to r413 are each 4.

[0338] According to one embodiment of the present specification, each of R411 to R413 is F.

[0339] According to one embodiment of the present specification, the chemical formula HI-2 is represented by the following compound.

[0340]

[0341] According to one embodiment of the present specification, the hole injection layer includes the chemical formulas HI-1 and HI-2.

[0342] According to one embodiment of the present specification, the hole injection layer comprises the chemical formulas HI-1 and HI-2 in a weight ratio of 1:99 to 99:1. Preferably, it comprises the chemical formulas HI-1 and HI-2 in a weight ratio of 10:90 to 90:10.

[0343] The above-mentioned hole transport layer can play a role in facilitating hole transport. A hole transport material capable of transporting holes from the anode or hole injection layer and transferring them to the light-emitting layer, and a material with high hole mobility is suitable. Specific examples of hole transport materials include, but are not limited to, arylamine compounds, carbazole compounds, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0344] In the organic light-emitting device of the present specification, the hole transport layer may be a carbazole-based compound substituted with an arylamine group, but is not limited thereto.

[0345] According to one embodiment of the present specification, the hole transport layer includes, but is not limited to, a compound represented by the chemical formula HI-1.

[0346] An electron-blocking (hole-regulating, or electron-suppressing) layer may be provided between the hole-transporting layer and the light-emitting layer. The electron-blocking (hole-regulating, or electron-suppressing) layer is a layer that prevents electrons from flowing into the light-emitting layer to the anode and controls the flow of holes flowing into the light-emitting layer to control the performance of the entire device. The electron-blocking material (hole-regulating, or electron-suppressing material) is preferably a compound that has the ability to prevent electrons from flowing into the anode from the light-emitting layer and control the flow of holes injected into the light-emitting layer or the light-emitting material. In one embodiment, an arylamine-based organic material may be used as the electron-blocking (hole-regulating, or electron-suppressing) layer, but is not limited thereto.

[0347] In the organic light-emitting device of the present invention, the electron-blocking (hole-controlling, or electron-suppressing) layer may include an amine compound containing a carbazole group. In one example, the compound may have a carbazole group and an amine group connected by an ortho-biphenylene group, a meta-biphenylene group, or a para-biphenylene group.

[0348] According to one embodiment of the present specification, the electron blocking (hole control, or electron suppression) layer includes, but is not limited to, a compound of the following chemical formula EG-1.

[0349] [Chemical formula EB-1]

[0350]

[0351] In the above chemical formula EB-1,

[0352] R501 to R504 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0353] L101 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0354] Ar101 and Ar102 are the same or different, and each independently represents a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0355] l101 is an integer from 1 to 3, and when l101 is 2 or more, 2 or more L101 are the same as or different from each other.

[0356] R501 is an integer from 1 to 5, and when r501 is 2 or more, 2 or more R501 are the same as or different from each other,

[0357] R504 is an integer from 1 to 5, and when r504 is 2 or more, 2 or more R504 are the same as or different from each other,

[0358] R502 is an integer from 1 to 3, and when r502 is 2 or more, 2 or more R502 are the same as or different from each other,

[0359] R503 is an integer from 1 to 4, and when r503 is 2 or more, 2 or more R503 are the same as or different from each other.

[0360] According to one embodiment of the present specification, R501 to R504 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0361] According to one embodiment of the present specification, R501 to R504 are hydrogen.

[0362] According to one embodiment of the present specification, L101 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0363] According to one embodiment of the present specification, L101 is a direct bond; a phenylene group; or a naphthylene group.

[0364] According to one embodiment of the present specification, the L101 is a direct bond.

[0365] According to one embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0366] According to one embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and are each independently a phenyl group; a biphenyl group; or a naphthyl group.

[0367] According to one embodiment of the present specification, the EB-1 is represented by any one of the following compounds.

[0368]

[0369] The above-mentioned light-emitting layer can emit red, green, or blue light, and can be made of a phosphorescent material or a fluorescent material. The above-mentioned light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole series compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; benzoxazole, benzthiazole, and benzimidazole series compounds; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0370] Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocyclic compound-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compound-containing compounds include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc.

[0371] In the organic light-emitting device of the present specification, the host may be a compound of the above-described chemical formula 1 or an anthracene derivative, but is not limited thereto.

[0372] In the organic light-emitting device of the present specification, the host may include the compound of the above-described chemical formula 1 as the first host, and may further include a second host.

[0373] In the organic light-emitting device of the present specification, the second host may be a compound of the following chemical formula H.

[0374] [Chemical formula H]

[0375]

[0376] In the above chemical formula H,

[0377] L20 and L21 are the same or different, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0378] Ar20 and Ar21 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0379] 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,

[0380] r301 is an integer from 1 to 8, and when r301 is 2 or more, 2 or more R301 are the same as or different from each other.

[0381] In one embodiment of the present specification, the first host includes at least one compound of the above chemical formula 1.

[0382] In one embodiment of the present specification, the first host includes two or more compounds of the chemical formula 1, and the two or more compounds are the same or different from each other.

[0383] In one embodiment of the present specification, the first host includes a compound of the above chemical formula 1, and may further include at least one chrysene-based compound different from the above chemical formula 1.

[0384] In one embodiment of the present specification, the first host includes a compound of the above chemical formula 1, and may further include at least one chrysene-based compound different from the above chemical formula 1, and at least one non-chrysene-based compound, and the non-chrysene-based compound may include a compound having a higher triplet energy than the above chemical formula H, but is not limited thereto.

[0385] The above chrysene-based compounds and compounds other than chrysene-based compounds may use conventional compounds, but are not limited thereto.

[0386] In one embodiment of the present specification, the second host includes a compound of the chemical formula H, and may further include at least one anthracene compound different from the chemical formula H.

[0387] In one embodiment of the present specification, the second host includes a compound of the chemical formula H, and may further include one anthracene compound different from the chemical formula H.

[0388] In one embodiment of the present specification, the second host may use two or more compounds of the chemical formula H, and the two or more compounds are different from each other.

[0389] The above anthracene compound may be a conventional compound, but is not limited thereto.

[0390] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represents a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

[0391] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represent a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylylene group substituted or unsubstituted with deuterium; a naphthylene group substituted or unsubstituted with deuterium; a divalent dibenzofuran group; or a divalent dibenzothiophene group.

[0392] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0393] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

[0394] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a terphenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a phenanthrene group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran 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.

[0395] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group; a naphthyl group substituted or unsubstituted with deuterium; a thiophene group substituted or unsubstituted with a phenyl group; a phenanthrene group; a dibenzofuran group; a naphthobenzofuran group; a dibenzothiophene group; or a naphthobenzothiophene group.

[0396] In one embodiment of the present specification, R301 is hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0397] In one embodiment of the present specification, R301 is hydrogen; deuterium; an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with 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 with deuterium.

[0398] In one embodiment of the present specification, R301 is hydrogen; deuterium; a phenyl group unsubstituted or substituted with deuterium, a phenyl group, a naphthyl group, or a combination thereof; a biphenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium, a phenyl group, a naphthyl group, or a combination thereof; a dibenzofuran group unsubstituted or substituted with deuterium; or a dibenzothiophene group unsubstituted or substituted with deuterium.

[0399] In one embodiment of the present specification, R301 is hydrogen.

[0400] In one embodiment of the present specification, R301 is deuterium.

[0401] According to one embodiment of the present specification, the chemical formula H is any one of the following compounds.

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412] According to one embodiment of the present specification, the first host and the second host can be deposited on the light-emitting layer in the form of a bi-layer, co-deposition, or pre-mix.

[0413] According to one embodiment of the present specification, the second host can be used as a hyperfluorescence (or triple-sensitized fluorescence) host of the light-emitting layer.

[0414] When the light-emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits green light, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distriarylene (DSA), PFO polymer, or PPV polymer can be used as a light-emitting dopant, but is not limited thereto.

[0415] In the organic light-emitting device of the present specification, a polycyclic compound containing boron, a Pt-containing compound, or an Ir complex may be used as the light-emitting dopant, but is not limited thereto.

[0416] In the organic light-emitting device of the present specification, the light-emitting layer includes the compound of the above chemical formula 1 as a host and may further include a dopant.

[0417] In the organic light-emitting device of the present specification, the dopant may be a compound of the following chemical formula D.

[0418] [Chemical Formula D]

[0419]

[0420] In the above chemical formula D,

[0421] X1 and X2 are the same or different from each other, and are each independently CR'; NR" or O, and at least one of X1 and X2 is NR",

[0422] A and C are the same or different and are each independently a substituted or unsubstituted 5-membered ring; or a substituted or unsubstituted 6-membered ring,

[0423] R401, R' and R" are the same or different and each independently represent 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 aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0424] r401 is an integer from 0 to 3, and when r401 is 2 or more, the 2 or more R401s are the same as or different from each other.

[0425] In the organic light-emitting device of the present specification, A and C are the same as or different from each other, and each independently represents a substituted or unsubstituted hydrocarbon ring; a substituted or unsubstituted heterocycle; or a condensed ring thereof.

[0426] In the organic light-emitting device of the present specification, A and C are the same as or different from each other, and each independently represents a hydrocarbon ring substituted or unsubstituted with an alkyl group or an arylamine group; or a heterocycle substituted or unsubstituted with an alkyl group.

[0427] In the organic light-emitting device of the present specification, A and C are the same as or different from each other, and are each independently benzene substituted or unsubstituted with an arylamine group; tetrahydronaphthalene substituted or unsubstituted with an alkyl group; benzofuran substituted or unsubstituted with an alkyl group; or benzothiophene substituted or unsubstituted with an alkyl group.

[0428] In the organic light-emitting device of the present specification, A and C are the same as or different from each other, and are each independently benzene substituted or unsubstituted with a diphenylamine group; benzofuran substituted or unsubstituted with a tert-butyl group; benzothiophene substituted or unsubstituted with a tert-butyl group; or (1,1,4,4)-tetramethyl-(1,2,3,4)-tetrahydronaphthyl group.

[0429] In the organic light-emitting device of the present specification, R401, R' and R" are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.

[0430] In the organic light-emitting device of the present specification, R401 is hydrogen; deuterium; an alkyl group having 1 to 10 carbon atoms; or an aryl group having 6 to 30 carbon atoms.

[0431] In the organic light-emitting device of the present specification, R401 is a methyl group; a tert-butyl group; or a phenyl group.

[0432] In the organic light-emitting device of the present specification, R" is a substituted or unsubstituted aryl group.

[0433] In the organic light-emitting device of the present specification, R" is a substituted or unsubstituted phenyl group; or a substituted or unsubstituted tetrahydronaphthyl group.

[0434] In the organic light-emitting device of the present specification, R" is a phenyl group substituted or unsubstituted with a tert-butyl group; a phenyl group substituted with a phenyl group and an adamantyl group; a biphenyl group substituted or unsubstituted with a tert-butyl group; or a (1,1,4,4)-tetramethyl-(1,2,3,4)-tetrahydronaphthyl group.

[0435] In the organic light-emitting device of the present specification, r401 is 1.

[0436] According to one embodiment of the present specification, the chemical formula D is any one of the following compounds.

[0437]

[0438] In addition, one embodiment of the present specification provides an organic light-emitting device including an anode; a cathode; a first light-emitting layer provided between the anode and the cathode; and a second light-emitting layer provided between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, wherein the first light-emitting layer includes a compound of the chemical formula 1, and the second light-emitting layer includes a compound of the chemical formula H.

[0439] According to an embodiment of the present specification, an organic light-emitting device may include a plurality of light-emitting layers, each of which may include a compound of the chemical formula 1 and a compound of the chemical formula H. For example, the light-emitting layer may include a first light-emitting layer including a compound of the chemical formula 1 and a second light-emitting layer including a compound of the chemical formula H. At this time, the second light-emitting layer may be provided between the first light-emitting layer and the cathode. The first light-emitting layer and the second light-emitting layer may be provided in contact with each other. When the first light-emitting layer and the second light-emitting layer each include the compound of the chemical formula 1 and the compound of the chemical formula H as a host, the first light-emitting layer and the second light-emitting layer each further include a dopant compound. At this time, the first light-emitting layer and the second light-emitting layer may include the same type of dopant material or may include different types of dopant materials, but it is preferable that they include the same type of dopant material.

[0440] An organic light-emitting device according to one embodiment of the present specification is provided with the second light-emitting layer between the first light-emitting layer and the cathode.

[0441] An organic light-emitting device according to one embodiment of the present specification is provided such that the first light-emitting layer and the second light-emitting layer are in direct contact. When this configuration is satisfied, the efficiency of the organic light-emitting device can be further improved.

[0442] According to one embodiment of the present specification, the chemical formula 1 is a host of the first light-emitting layer.

[0443] According to one embodiment of the present specification, the chemical formula H is a host of the second light-emitting layer.

[0444] According to one embodiment of the present specification, the first light-emitting layer and the second light-emitting layer each include a dopant, and the dopant is as described above. The dopants may be the same or different.

[0445] According to one embodiment of the present specification, the first light-emitting layer includes the compound of the chemical formula 1 as a host and further includes a dopant material. At this time, the dopant material may be included in the first light-emitting layer in an amount of about 0.01 wt% to 20 wt%, or 0.01 wt% to 10 wt%, relative to the total weight of the compound of the chemical formula 1.

[0446] According to one embodiment of the present specification, the second light-emitting layer includes the compound of the chemical formula H as a host and further includes a dopant material. At this time, the dopant material may be included in the second light-emitting layer in an amount of about 0.01 wt% to 20 wt%, or 0.01 wt% to 10 wt%, relative to the total weight of the compound of the chemical formula H.

[0447] A hole-blocking (electron-controlling) layer may be provided between the electron transport layer and the light-emitting layer, and the hole-blocking (electron-controlling) layer is a layer that blocks holes from the light-emitting layer from flowing into the cathode and controls electrons flowing into the light-emitting layer to control the performance of the entire device. As the hole-blocking (electron-controlling) material, a compound having the ability to prevent holes from flowing into the cathode from the light-emitting layer and to control electrons injected into the light-emitting layer or the light-emitting material is preferable. An appropriate material may be used as the hole-blocking (electron-controlling) material depending on the composition of the organic layer used in the device. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc.

[0448] In one embodiment of the present specification, the hole-blocking (electron-controlling) layer may include a compound having a structure in which an N-containing ring is directly connected to a spiro[fluorene-9,9'-xanthene] structure or through a linker.

[0449] The electron transport layer can facilitate electron transport. Suitable electron transport materials include those capable of readily receiving electrons from the cathode and transporting them to the light-emitting layer, and those with high electron mobility. Specific examples include, but are not limited to, the aforementioned compounds, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes.

[0450] In one embodiment of the present specification, the electron transport layer may include a compound including an N-containing ring, and may further include an n-type dopant or an organometallic compound. According to one example, the compound including an N-containing ring may be a triazine-based compound, and the n-type dopant or organometallic compound may preferably be a lithium metal complex compound, for example, 8-hydroxyquinolinato lithium, and the compound including an N-containing ring and the n-type dopant (or organometallic compound) may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.

[0451] According to one embodiment of the present specification, the electron transport layer has one or more layers.

[0452] According to one embodiment of the present specification, the electron transport layer is two-layered and includes a first electron transport layer and a second electron transport layer.

[0453] According to one embodiment of the present specification, the electron transport layer is of the following chemical formula ET-1.

[0454] [Chemical formula ET-1]

[0455]

[0456] In the above chemical formula ET-1,

[0457] Either R601 or R604 and the rest are the same or different and are each independently hydrogen; deuterium; or cyano group,

[0458] r601 to r604 are each an integer from 1 to 4, and when r601 to r604 are each 2 or more, 2 or more of R601 to R604 are the same as or different from each other.

[0459] L102 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0460] l102 is an integer from 1 to 3, and when l102 is 2 or more, 2 or more L102 are equal to or different from each other,

[0461] At least one of Z1 to Z3 is N, and the rest are CH,

[0462] Ar201 and Ar202 are the same or different, and each independently represents a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

[0463] According to one embodiment of the present specification, among R601 to R604 The remainder are the same or different and are each independently hydrogen; or cyano group.

[0464] According to one embodiment of the present specification, L102 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0465] According to one embodiment of the present specification, L102 is a direct bond; a phenylene group; or a naphthylene group.

[0466] According to one embodiment of the present specification, the L102 is a direct bond.

[0467] According to one embodiment of the present specification, Ar201 and Ar202 are the same as or different from each other, and each independently is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0468] According to one embodiment of the present specification, Ar201 and Ar202 are the same as or different from each other, and are each independently a phenyl group; a biphenyl group; or a naphthyl group.

[0469] According to one embodiment of the present specification, Z1 to Z3 are N.

[0470] According to one embodiment of the present specification, the chemical formula ET-1 is any one of the following compounds.

[0471]

[0472] According to one embodiment of the present specification, the electron transport layer includes a first electron transport layer and a second electron transport layer, the first electron transport layer and the second electron transport layer include the chemical formula ET-1, and the chemical formula ET-1 included in the first electron transport layer and the second electron transport layer are different from each other.

[0473] According to one embodiment of the present specification, the first electron transport layer and the second electron transport layer include the chemical formula ET-1, and the chemical formulas ET-1 are different from each other.

[0474] The electron transport layer further includes a metal complex compound. As the metal complex compound, the compound is lithium 8-hydroxyquinolinato (LiQ), bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, Examples include, but are not limited to, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc.

[0475] According to one embodiment of the present specification, the second electron transport layer includes the chemical formula ET-1 and a metal complex. The chemical formula ET-1 and the metal complex are included in a weight ratio of 1:9 to 9:1, 4:6 to 6:4, or 1:2 to 2:1.

[0476] The above electron injection layer can play a role in facilitating electron injection. As the electron injection material, a compound having the ability to transport electrons, an electron injection effect from the cathode, an excellent electron injection effect for the light-emitting layer or light-emitting material, a compound that prevents the movement of excitons generated in the light-emitting layer to the hole injection layer, and an excellent thin film forming ability is preferable. Specific examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0477] The above metal complex compounds include 8-hydroxyquinolinato lithium (LiQ), bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

[0478] In one embodiment of the present specification, the electron injection layer may include lithium fluoride (LiF).

[0479] In one embodiment of the present specification, the electron injection layer includes LiQ (8-hydroxyquinolinato lithium).

[0480] The organic light-emitting device according to the present invention may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

[0481] Hereinafter, examples will be provided to specifically explain the present specification. However, the embodiments described herein may be modified in various ways, and the scope of the present application is not limited to the embodiments described below. The embodiments of the present application are provided to more fully explain the present specification to those of ordinary skill in the art.

[0482] <Synthesis example>

[0483] Synthesis example 1.

[0484]

[0485] In a nitrogen atmosphere, compound 1-chlorochrysene (30 g, 114.2 mmol, 1 eq.) was completely dissolved in 120 mL (1 M) of dichlorobenzene (hereinafter referred to as DCB) by heating and stirring in a round-bottom flask. Upon complete dissolution, trifluoromethanesulonic acid-d (hereinafter referred to as TfOD, 20 eq. 202 mL) was added and the mixture was heated and stirred at 130°C for 2 hours. After completion of the reaction, the temperature was lowered, the aqueous layer was removed, and the solution was washed with aq. NaHCO3 to confirm that the pH was neutral. The organic layer was collected, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized under toluene / EtOH conditions to prepare compound M-1 (21.7 g, 70%).

[0486] Mass analysis of compound M-1 showed a deuterium substitution rate of approximately 90%.

[0487] MS[M+H] + = 273

[0488] Synthesis example 2.

[0489]

[0490] In a nitrogen atmosphere, compounds M-1 (8 g, 29.41 mmol, 1 eq.) and M-2 (8.5 g, 1.1 eq.) were dissolved in 320 mL (0.1 M) of 1,4-dioxane in a round-bottom flask and stirred. Even if not completely dissolved, aq. K3PO4 (12.5 g in 80 mL of H2O, 2 eq.) was added, and bis(tri-tert-butylphosphine)palladium(0) (0.15 g, 1 mol%) was added, followed by heating and stirring for 2 hours. The temperature was lowered to room temperature, filtered under reduced pressure to obtain a solid. The obtained solid was dissolved in toluene and washed with water. The aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized under toluene conditions to prepare compound C-1 (8.7 g, 65%).

[0491] MS[M+H] + = 455

[0492] Synthesis example 3.

[0493]

[0494] Compound C-18 was synthesized using M-1 (8 g, 1 eq.) and M-3 as starting materials in the same manner as in Synthesis Example 2. Compound C-18 (8.0 g, 52%) was prepared by recrystallization under toluene conditions.

[0495] MS[M+H] + = 521

[0496] Synthesis example 4.

[0497]

[0498] In a nitrogen atmosphere, compounds M-4 (90% deuterium substitution, 10 g, 28.57 mmol, 1 eq.) and M-5 (4 g, 1.1 eq.) were dissolved in 200 mL (0.15 M) of 1,4-dioxane in a round-bottom flask and stirred. Even if not completely dissolved, aq. K2CO3 (7.9 g in 50 mL of H2O, 2 eq.) was added, and tetrakis(triphenylphosphine)palladium(0) (0.33 g, 1 mol%) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, and ethanol in the same amount as the solvent was added, followed by stirring. A solid was obtained by filtering under reduced pressure. The obtained solid was dissolved in toluene and washed with water. The water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized under toluene / ethanol conditions to prepare compound M-6 (8.3 g, 83%).

[0499] MS[M+H] + = 353

[0500] Synthesis Example 5.

[0501]

[0502] Compound C-21 was synthesized using M-6 (7 g, 1 eq.) and M-7 as starting materials in the same manner as in Synthesis Example 2. Compound C-21 (5.2 g, 47%) was prepared by recrystallization under toluene conditions.

[0503] MS[M+H] + = 561

[0504] Synthesis Example 6.

[0505]

[0506] Compound M-8 was synthesized using M-4 (7 g, 1 eq.) and M-2 as starting materials in the same manner as in Synthesis Example 4. Compound M-8 (5.2 g, 47%) was prepared by recrystallization under toluene / ethanol conditions.

[0507] Compound C-23 was synthesized using M-8 (7 g, 1 eq.) and M-9 as starting materials in the same manner as in Synthesis Example 2. Compound C-23 (5.9 g, 61%) was prepared by recrystallization under toluene conditions.

[0508] MS[M+H] + = 670

[0509] Synthesis Example 7.

[0510]

[0511] Compound M-12 was synthesized using M-10 (10 g, 1 eq.) and M-11 as starting materials in the same manner as in Synthesis Example 4. Compound M-12 (8.9 g, 73%) was prepared by recrystallization under toluene / ethanol conditions.

[0512] Compound C-8 was synthesized using M-12 (8 g, 1 eq.) and M-13 (40% deuterium substitution rate) as starting materials using the same method as Synthesis Example 2. Compound C-8 (4.3 g, 33%) was prepared by recrystallization under toluene / ethyl acetate conditions.

[0513] MS[M+H] + = 683

[0514] Synthesis Example 8.

[0515]

[0516] Compound C-6 was synthesized using 1-chlorochrysene (10 g, 1 eq.) and M-14 (deuterium substitution rate 41%) as starting materials using the same method as Synthesis Example 2. Compound C-6 (14 g, 61%) was prepared by recrystallization under toluene conditions.

[0517] MS[M+H] + = 521

[0518] Synthesis Example 9.

[0519]

[0520] Compound M-17 was synthesized using M-15 (5 g, 1 eq.) and M-16 as starting materials in the same manner as in Synthesis Example 4. Compound M-17 (5.9 g, 78%) was prepared by recrystallization under toluene / ethyl acetate conditions.

[0521] MS[M+H] + = 621

[0522] Compound C-7 was synthesized using M-17 (8 g, 1 eq.) and M-5 (deuterium substitution rate of 95% or more) as starting materials using the same method as Synthesis Example 2. Compound C-7 (2.9 g, 54%) was prepared by recrystallization under toluene conditions.

[0523] MS[M+H] + = 668

[0524] Synthesis Example 10.

[0525]

[0526] Compound C-20 was synthesized using M-18 (7 g, 1 eq.) and M-19 as starting materials in the same manner as in Synthesis Example 2. Compound C-20 (8.7 g, 81%) was prepared by recrystallization under toluene conditions.

[0527] MS[M+H] + = 526

[0528] Synthesis Example 11.

[0529]

[0530] Compound M-20 was synthesized using 2-chlorochrysene (30 g, 1 eq.) as a starting material using the same method as Synthesis Example 1. Compound M-20 (24.5 g, 79%) was prepared by recrystallization under toluene / ethanol conditions.

[0531] Mass analysis of compound M-20 showed a deuterium substitution rate of approximately 90%.

[0532] MS[M+H] + = 273

[0533] Compound C-11 was synthesized using M-20 (8 g, 1 eq.) and M-21 as starting materials in the same manner as in Synthesis Example 2. Compound C-11 (9.5 g, 77%) was prepared by recrystallization under toluene conditions.

[0534] MS[M+H] + = 421

[0535] Synthesis Example 12.

[0536]

[0537] Compound C-2 was synthesized using 3-chlorochrysene (10 g, 1 eq.) and M-22 (deuterium substitution rate 64%) as starting materials using the same method as Synthesis Example 2. Compound C-2 (11.7 g, 68%) was prepared by recrystallization under toluene conditions.

[0538] MS[M+H] + = 452

[0539] Synthesis Example 13.

[0540]

[0541] Compound M-24 was synthesized using 3-chlorochrysene (10 g, 1 eq.) and M-23 as starting materials using the same method as in Synthesis Example 2. Compound M-24 (14.9, 70%) was prepared by recrystallization under toluene conditions.

[0542] MS[M+H] + = 561

[0543] Compound C-15 was synthesized using 30 eq. TfOD and compound M-24 (14 g, 1 eq.) as a starting material in the same manner as in Synthesis Example 1. Compound C-15 (3.9 g, 27%) was prepared by recrystallization under toluene conditions.

[0544] Mass analysis of compound C-15 showed a deuterium substitution rate of approximately 54%.

[0545] MS[M+H] + = 574

[0546] Synthesis Example 14.

[0547]

[0548] Compound C-3 was synthesized using 6-bromochrysene-d11 (10 g, 1 eq., deuterium substitution rate 95%) and M-25 as starting materials using the same method as in Synthesis Example 2. Compound C-3 (13.5, 74%) was prepared by recrystallization under toluene conditions.

[0549] MS[M+H] + = 581

[0550] Synthesis Example 15.

[0551]

[0552] Compound M-27 was synthesized using 6-bromochrysene-d11 (10 g, 1 eq., deuterium substitution rate 95%) and M-26 as starting materials using the same method as Synthesis Example 2. Compound M-27 (10.1 g, 88%) was prepared by recrystallization under toluene / ethanol conditions.

[0553] MS[M+H] + = 366

[0554] Synthesis Example 16.

[0555]

[0556] In a nitrogen atmosphere, compound M-27 (10 g, 27.3 mmol, 1 eq.) was dissolved in 140 mL (0.2 M) of N,N-Dimethylformamide in a round-bottom flask and stirred. N-Bromosuccinimide (5.4 g, 1.1 eq.) was added and stirred at 40°C for 6 hours. After completion of the reaction, the temperature was lowered to room temperature, 70 mL of water and 140 mL of ethanol were added, and stirred for 30 minutes. After filtration, the solid was dissolved in chloroform, washed with aq. Na2S2O3 and aq. NaHCO3, and the aqueous layer was removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized under toluene / hexane conditions to prepare compound M-28 (9.7 g, 80%).

[0557] MS[M+H] + = 442

[0558] Synthesis Example 17.

[0559]

[0560] Compound C-9 was synthesized using M-28 (8 g, 1 eq.) and M-29 as starting materials in the same manner as in Synthesis Example 2. Compound C-9 (5.1 g, 48%) was prepared by recrystallization under toluene conditions.

[0561] MS[M+H] + = 588

[0562] Synthesis Example 18.

[0563]

[0564] Compound M-31 was synthesized using 6-bromochrysene-d11 (10 g, 1 eq., deuterium substitution rate 95%) and M-30 as starting materials using the same method as Synthesis Example 2. Compound M-31 (9.5 g, 77%) was prepared by recrystallization under toluene / hexane conditions.

[0565] MS[M+H] + = 391

[0566] Compound M-32 was synthesized using M-31 (8 g, 1 eq.) as a starting material using the same method as Synthesis Example 16. Compound M-32 (9.1 g, 84%) was prepared by recrystallization under toluene / hexane conditions.

[0567] MS[M+H] + = 468

[0568] Synthesis Example 19.

[0569]

[0570] Compound C-14 was synthesized using M-32 (7 g, 1 eq.) and M-33 as starting materials in the same manner as in Synthesis Example 2. Compound C-14 (3.6 g, 41%) was prepared by recrystallization under toluene conditions.

[0571] MS[M+H] + = 672

[0572] Synthesis Example 20.

[0573]

[0574] Compound M-34 was synthesized using 6-bromochrysene-d11 (10 g, 1 eq., deuterium substitution rate 95%) and M-5 as starting materials using the same method as Synthesis Example 2. Compound M-34 (9.2 g, 91%) was prepared by recrystallization under toluene / hexane conditions.

[0575] MS[M+H] + = 320

[0576] Compound M-35 was synthesized using M-34 (8 g, 1 eq.) as a starting material using the same method as Synthesis Example 16. Compound M-35 (7.9 g, 79%) was prepared by recrystallization under toluene / hexane conditions.

[0577] MS[M+H] + = 397

[0578] Synthesis Example 21.

[0579]

[0580] Compound C-17 was synthesized using M-35 (7 g, 1 eq.) and M-36 as starting materials in the same manner as in Synthesis Example 2. Compound C-17 (2.9 g, 27%) was prepared by recrystallization under toluene conditions.

[0581] MS[M+H] + = 617

[0582] Synthesis Example 22.

[0583]

[0584] Compound M-38 was synthesized using 6-bromochrysene-d11 (20 g, 1 eq., deuterium substitution rate 95%) and M-37 as starting materials using the same method as Synthesis Example 2. Compound M-38 (21.2 g, 80%) was prepared by recrystallization under toluene / hexane conditions.

[0585] MS[M+H] + = 421

[0586] Compound M-39 was synthesized using M-38 (20 g, 1 eq.) as a starting material in the same manner as in Synthesis Example 16. Compound M-39 (17.5 g, 74%) was prepared by recrystallization under toluene / hexane conditions.

[0587] MS[M+H] + = 498

[0588] Synthesis Example 23.

[0589]

[0590] Compound C-22 was synthesized using M-39 (7 g, 1 eq.) and M-40 as starting materials in the same manner as in Synthesis Example 2. Compound C-22 (3.6 g, 40%) was prepared by recrystallization under toluene conditions.

[0591] MS[M+H] + = 644

[0592] Synthesis Example 24.

[0593]

[0594] Compound M-42 was synthesized using M-39 (10 g, 1 eq.) and M-41 as starting materials in the same manner as in Synthesis Example 2. Compound M-42 (7.8 g, 65%) was prepared by recrystallization under toluene conditions.

[0595] MS[M+H] + = 602

[0596] Compound C-16 was synthesized using compound M-42 (7 g, 1 eq.) as a starting material in the same manner as in Synthesis Example 1. Compound C-16 (2.2 g, 31%) was prepared by recrystallization under toluene conditions.

[0597] Mass analysis of compound C-16 showed a deuterium substitution rate of approximately 71%.

[0598] MS[M+H] + = 610

[0599] Synthesis Example 25.

[0600]

[0601] Compound M-44 was synthesized using M-43 (10 g, 1 eq., deuterium substitution rate 45%) as a starting material in the same manner as in Synthesis Example 16. Compound M-44 (11.2 g, 89%) was prepared by recrystallization under toluene / ethanol conditions.

[0602] MS[M+H] + = 388

[0603] Compound C-4 was synthesized using M-44 (10 g, 1 eq.) and M-2 as starting materials in the same manner as in Synthesis Example 2. Compound C-4 (7.7 g, 57%) was prepared by recrystallization under toluene conditions.

[0604] MS[M+H] + = 526

[0605] Synthesis Example 26.

[0606]

[0607] Compound M-46 was synthesized using M-45 (10 g, 1 eq., deuterium substitution rate 50%) as a starting material in the same manner as in Synthesis Example 16. Compound M-46 (11.3 g, 93%) was prepared by recrystallization under toluene / ethanol conditions.

[0608] MS[M+H] + = 439

[0609] Compound C-12 was synthesized using M-46 (10 g, 1 eq.) and M-47 as starting materials in the same manner as in Synthesis Example 2. Compound C-12 (6.9 g, 50%) was prepared by recrystallization under toluene conditions.

[0610] MS[M+H] + = 603

[0611] Synthesis Example 27.

[0612]

[0613] Compound M-49 was synthesized using M-48 (10 g, 1 eq.) as a starting material using the same method as Synthesis Example 16. Compound M-49 (9.8 g, 82%) was prepared by recrystallization under toluene / hexane conditions.

[0614] MS[M+H] + = 483

[0615] Compound M-50 was synthesized using M-49 (9 g, 1 eq.) and M-2 as starting materials in the same manner as in Synthesis Example 2. Compound M-50 (7.6 g, 66%) was prepared by recrystallization under toluene conditions.

[0616] MS[M+H] + = 621

[0617] Synthesis Example 28.

[0618]

[0619] Compound C-5 was synthesized using compound M-50 (7 g, 1 eq.) as a starting material and 30 eq. TfOD in the same manner as in Synthesis Example 1. Compound C-5 (2.7 g, 38%) was prepared by recrystallization under toluene conditions.

[0620] Mass analysis of compound C-5 showed a deuterium substitution rate of approximately 71%.

[0621] MS[M+H] + = 636

[0622] Synthesis Example 29.

[0623]

[0624] In a nitrogen atmosphere, 6,12-dibromochrysene (15 g, 38.85 mmol, 1 eq.) and M-51 (30.21 g, 2.1 eq.) were dissolved in 750 mL (0.05 M) of 1,4-dioxane in a round-bottom flask and stirred. Even if it was not completely dissolved, aq. K3PO4 (24.7 g in 180 mL of H2O, 3 eq.) was added, and Bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 1 mol%) was added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, and the mixture was filtered under reduced pressure to obtain a solid. The obtained solid was dissolved in xylene and washed with water. The aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized under toluene conditions to prepare compound M-52 (17.6 g, 73%).

[0625] MS[M+H] + = 713

[0626] Compound C-13 was synthesized using compound M-52 (10 g, 1 eq.) as a starting material and 35 eq. TfOD and 0.2 M DCB in the same manner as in Synthesis Example 1. Compound C-13 (4.8 g, 41%) was prepared by recrystallization under toluene conditions.

[0627] Mass analysis of compound C-13 showed a deuterium substitution rate of approximately 62%.

[0628] MS[M+H] + = 733

[0629] <Experimental Example 1: Calculation of Triplet Energy Levels>

[0630] The following compounds were calculated for their HOMO energy level, LUMO energy level, and singlet and triplet energy levels based on absorption states using the TD-DFT (B3LYP) method / 6-31G* basis method. The calculation results are identical for the structures containing hydrogen (H) and deuterium (D) in the same structure below due to the difference.

[0631] The calculation results of the HOMO energy level, LUMO energy level, singlet energy level, and triplet energy level of the following compounds are as shown in Table 1 below.

[0632]

[0633] Compound A-1A-2A-3A-4A-5A-6HOMO (eV) 5.225.325.335.515.735.79LUMO (eV) 1.631.551.481.270.990.96S1 (eV) 3.273.403.723.784.024.46T1 (eV) 1.802.052.122.502.742.73Compound A-7A-8A-9A-10A-11A-12HOMO (eV) 6.706.015.535.575.575.81LUMO (eV) 0.090.921.411.071.290.95S1 (eV)5.534.533.734.033.914.19T1 (eV)3.803.202.422.702.593.15Compound A-13A-14A-15B-1B-2B-3HOMO (eV)5.435.635.585.125.125.18LUMO (eV)1.431.341.221.631.621.68S1 (eV)3.533.833.883.163.173.15T1 (eV)2.362.592.621.741.741.73Compound B-4X-1X-2X-3X-4X-5HOMO (eV)5.495.465.435.335.105.36LUMO (eV)1.341.441.431.391.611.38S1 (eV)3.733.583.573.533.163.50T1 (eV)2.552.412.402.371.742.37Compound

[0634] As shown in the results in Table 1 of the above Experimental Example 2, the relative values ​​of the triplet energy levels of various functional groups were confirmed (compounds A1 to A15), and through this, it was found that the triplet energy level of a compound is determined by the functional group with the lowest triplet energy level contained in the compound.

[0635] Compounds B-1 to B-3 and X-4 were confirmed to have similar T1 values ​​to A-4 because the triplet energy was determined by compound A-1, and the functional group with the lowest triplet energy level in compounds X-2 and X-3 was A-4. Compound B-4 is a combination of functional groups with higher triplet energy than chrysene, and it can be expected that the triplet energy of B-4 is determined by compounds A-5 and A-6, which have similar values.

[0636] In addition, although the T1 values ​​of compounds A-9 and A-13 are lower than those of compound A-4, compounds A-9 and A-13 have similar values ​​that are 0.2 eV or less lower than the triplet energy level of compound A-4, so the T1 of the final compounds X-1, X-5 and X-8 have values ​​close to those of compounds X-2 and X-3 that were influenced by compound A-4.

[0637] <Experimental Example 2: Fabrication of an Organic Light-Emitting Device>

[0638] Example 1-1

[0639] A glass substrate coated with a 1,400 Å thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent was a Fischer Co. product, and the distilled water was secondarily filtered through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes each. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

[0640] On the ITO transparent electrode prepared as above, a hole injection layer was formed by thermal vacuum depositing the compounds HT-A and HI-A below at a weight ratio of 90:10 to a thickness of 110 Å. On the hole injection layer, HT-A below was vacuum deposited to a thickness of 1000 Å to form a hole transport layer. On the hole transport layer, HT-B below was vacuum deposited to a thickness of 50 Å to form an electron blocking layer. Subsequently, a light emitting layer was formed by co-depositing compound C-4 and blue fluorescent dopant BD-2 at a weight ratio (wt%) of 97:3 to a thickness of 200 Å on the electron blocking layer. Subsequently, 50 Å of the compound ET-A below was vacuum deposited as a first electron transport layer on the light emitting layer, and subsequently, ET-B and LiQ below were vacuum deposited at a weight ratio of 2:1 to form a second electron transport layer with a thickness of 300 Å. LiQ was vacuum-deposited on the second electron transport layer to a thickness of 5 Å to form an electron injection layer. Aluminum and silver were deposited on the electron injection layer at a weight ratio of 10:1 to a thickness of 220 Å, and aluminum was deposited thereon to a thickness of 1000 Å to form a cathode.

[0641] In the above process, the deposition rate of organic matter was maintained at 0.4 to 0.9 Å / sec, the aluminum of the cathode was maintained at a deposition rate of 2 Å / sec, and the vacuum during deposition was 1 Х 10 -7 ~ 5 Х 10 -8 Torr was maintained, and an organic light-emitting device was fabricated.

[0642]

[0643] Examples 1-2 to 1-5

[0644] Organic light-emitting devices of Examples 1-2 to 1-5 were manufactured using the same method as Example 1-1, except that the host compounds described in Table 2 below were used instead as the light-emitting layer materials in Example 1-1.

[0645] Comparative Examples 1-1 to 1-3

[0646] Organic light-emitting devices of Comparative Examples 1-1 to 1-3 were each manufactured using the same method as in Example 1-1, except that the host compounds described in Table 2 below were used instead as the light-emitting layer materials in Example 1-1.

[0647] Table 2 below shows the hosts used in the light-emitting layer, and the organic light-emitting devices manufactured therefrom are emitting at 10 mA / cm 2 The driving voltage, luminous efficiency (EQE), and maximum luminous wavelength (EL-max) were measured at a current density of 20 mA / cm. 2 The time required for the current density to reach 95% of the initial luminance was measured, and the relative value (life ratio) based on Comparative Example 1-3 was shown.

[0648]

[0649] EntryEmitting layerHost driving voltage(V)Emitting efficiency(EQE, %)LifespanratioEL-max(nm)Example 1-1C-44.046.311.20460Example 1-2C-74.066.061.11460Example 1-3C-114.055.951.28459Example 1-4C-133.996.201.34459Example 1-5C-173.976.121.50459Comparative example 1-1B-64.055.900.95464Comparative example 1-2B-74.084.100.03459Comparative example 1-3X-14.046.001.00460

[0650] In Table 2 above, the performance of organic light-emitting devices of compounds having different triplet energies (A-4, 2.5 eV) than those of chrysene in the chemical formula 1 of the present specification was investigated through Comparative Examples 1-1 and 1-2. The performance of Compound B-7 having a phenanthrene (A-5, 2.74 eV) substituent having a higher triplet energy than chrysene and Compound B-6 having a pyrene (A-3, 2.12 eV) substituent having a lower triplet energy than chrysene was confirmed. Comparative Example 1-2 including Compound B-7 was inferior to Examples 1-1 to 1-5 including the compounds of the present specification in both efficiency and lifespan.

[0651] Comparative Example 1-1 including the above compound B-6 had similar efficiency and lifespan to Examples 1-1 to 1-5 including the compound of the present specification, but had a problem in that the maximum emission wavelength of the organic light-emitting element was long, thereby reducing the color purity of blue emission.

[0652] In addition, when comparing Examples 1-1 to 1-5 of the present specification with Comparative Example 1-3, it was confirmed that the lifespan of Examples 1-1 to 1-5 was improved compared to Comparative Example 1-3, which can be judged to be the effect of deuterium substitution.

[0653] <Experimental Example 3: Fabrication of Organic Light-Emitting Devices>

[0654] Example 2-1

[0655] A glass substrate coated with a 1,400 Å thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent was a Fischer Co. product, and the distilled water was secondarily filtered through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes each. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

[0656] On the ITO transparent electrode prepared as above, a hole injection layer was formed by thermal vacuum depositing the compounds HT-A and HI-A below at a weight ratio of 90:10 to a thickness of 110 Å. On the hole injection layer, a hole transport layer was formed by vacuum depositing HT-A below at a thickness of 1000 Å. On the hole transport layer, an electron blocking layer was formed by vacuum depositing HT-B below at a thickness of 50 Å. Subsequently, the host of the first light-emitting layer shown in Table 3 below and the blue fluorescent dopant BD-1 were co-deposited at a weight ratio (wt%) of 95:5 to form a first light-emitting layer, and the host of the second light-emitting layer and the blue fluorescent dopant BD-1 were co-deposited at a weight ratio (wt%) of 95:5 to form a second light-emitting layer.

[0657] The thicknesses of the first and second light-emitting layers are shown in Table 3, and the sum of the thicknesses of the two light-emitting layers is 250 Å. Then, 50 Å of the following compound ET-A was vacuum-deposited as a first electron transport layer on the light-emitting layer, and subsequently, 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. LiQ was vacuum-deposited on the second electron transport layer to a thickness of 5 Å to form an electron injection layer. Aluminum and silver were deposited at a weight ratio of 10:1 on the electron injection layer to a thickness of 220 Å, and aluminum was deposited thereon to a thickness of 1000 Å to form a cathode.

[0658] In the above process, the deposition rate of organic matter was maintained at 0.4 to 0.9 Å / sec, the aluminum of the cathode was maintained at a deposition rate of 2 Å / sec, and the vacuum during deposition was 1 Х 10 -7 ~ 5 Х 10 -8 Torr was maintained, and an organic light-emitting device was fabricated.

[0659]

[0660] Examples 2-2 to 2-14, 2-19, 2-22 and 2-23

[0661] Organic light-emitting devices of Examples 2-2 to 2-14 and Example 2-19 were manufactured using the same method as Example 2-1, except that the host and dopant compounds described in Table 3 below were used instead of the light-emitting layer material of Example 2-1.

[0662] Examples 2-15 to 2-18

[0663] Instead of the light-emitting layer material of Example 2-1, the host and dopant compounds described in Table 3 below were used, and in particular, for the second host, B-1 and B-2 were co-deposited at a weight ratio (wt%) of 1:1 instead of compound B-2, and organic light-emitting devices of Examples 2-15 to 2-18 were manufactured using the same method as Example 2-1, respectively.

[0664] Examples 2-20 to 2-21

[0665] Instead of the light-emitting layer material of Example 2-1, the host and dopant compounds described in Table 3 below were used, and in particular, the organic light-emitting devices of Examples 2-20 to 2-21 were manufactured using the same method as Example 2-1, except that two types of compounds were co-deposited at a weight ratio (wt%) of 1:1 on the first host.

[0666] Comparative Examples 2-1 to 2-9

[0667] Organic light-emitting devices of Comparative Examples 2-1 to 2-9 were manufactured using the same method as in Example 2-1, except that the host and dopant compounds described in Table 3 below were used instead of the light-emitting layer material of Example 2-1.

[0668]

[0669]

[0670]

[0671] Table 3 below shows the compounds used in the light-emitting layer, and the organic light-emitting device manufactured therefrom was used at 10 mA / cm 2 The driving voltage and conversion efficiency (cd / A / y) were measured at a current density of 20 mA / cm 2 The time required for the current density to reach 95% of the initial luminance was measured, and the relative value (life ratio) based on Comparative Example 2-1 was shown.

[0672] Conversion efficiency (cd / A / y) takes into account the color purity (CIEy) of the material in addition to the current efficiency (cd / A), and is an important efficiency standard value in OLED devices that aim for high brightness and high color reproducibility.

[0673] Blue light-emitting layer (250 Å) Driving voltage (V) Conversion efficiency (cd / A / y) Lifetime Ratio 1st host 1st dopant 2nd host 2nd dopant Example 2-1 C-1, 50Å BD-1B-2, 200Å BD-14.14 56.02.00 Example 2-2 C-2, 50Å BD-1B-2, 200Å BD-14.05 56.61.92 Example 2-3 C-5, 50Å BD-1B-2, 200Å BD-14.12 55.11.89 Example 2-4 C-10, 50Å BD-2B-2, 200Å BD-24.09 54.61.79 Example 2-5 C-12, 50ÅBD-1B-2, 200ÅBD-14.0753.81.73Example 2-6C-19, 50ÅBD-2B-2, 200ÅBD-24.0753.61.89Example 2-7C-16, 50ÅBD-2B-2, 200ÅBD-24.0253.12.00Example 2-8C-3, 50ÅBD-3B-5, 200ÅBD-34.0056.21.95Example 2-9C-6, 50ÅBD-3B-5, 200ÅBD-34.0855.51.81Example 2-10C-8, 50ÅBD-3B-5, 200ÅBD-34.0255.91.84Example 2-11C-14, 50ÅBD-3B-5, 200ÅBD-33.9553.51.73Example 2-12C-15, 50ÅBD-3B-5, 200ÅBD-33.9452.81.75Example 2-13C-20, 50ÅBD-3B-5, 200ÅBD-33.9555.11.81Example 2-14C-22, 50ÅBD-3B-5, 200ÅBD-33.9154.31.98Example 2-15C-9, 50ÅBD-2B-1 + B-2, 200ÅBD-24.1855.61.79Example 2-16C-23, 50ÅBD-2B-1 + B-2, 200ÅBD-24.1255.31.86Example 2-17C-18, 50ÅBD-2B-1 + B-5, 200ÅBD-24.1555.01.81Example 2-18C-21, 30ÅBD-2B-1 + B-5, 220ÅBD-24.2454.71.71Example 2-19C-4, 30ÅBD-2B-5, 220ÅBD-23.9957.02.06Example 2-20C-3 + C-10, 50ÅBD-2B-5, 200ÅBD-14.0355.21.89Example 2-21C-3 + B-6, 50ÅBD-2B-5, 200ÅBD-33.9854.41.75Example 2-22C-24, 50ÅBD-3B-5, 200ÅBD-33.9857.32.22Example 2-23C-25, 30ÅBD-3B-5, 220ÅBD-33.9956.52.29Comparative Example 2-1B-1, 50ÅBD-1B-1, 200ÅBD-14.3252.61.00Comparative Example 2-2B-1, 50ÅBD-1B-2, 200ÅBD-14.0848.91.13Comparative Example 2-3B-5, 50ÅBD-1B-1, 200ÅBD-14.2450.01.07Comparative Example 2-4X-7, 50ÅBD-2B-2, 200ÅBD-24.1053.31.59Comparative Example 2-5B-5, 50ÅBD-2X-7, 200ÅBD-24.2950.61.02Comparative Example 2-6B-7, 50ÅBD-2B-5, 200ÅBD-23.9834.70.08Comparative Example 2-7B-7, 200ÅBD-2B-5, 50ÅBD-34.2332.30.02Comparative Example 2-8B-8, 50ÅBD-2B-2, 200ÅBD-24.2342.60.38Comparative Example 2-9X-9, 50ÅBD-2B-2, 200ÅBD-24.1552.31.41.

[0674] In the above Table 3, one or more compounds of Chemical Formula 1 were used as a host for the first light-emitting layer in an organic light-emitting device including a two-layer light-emitting layer. It was confirmed that the organic light-emitting device including Chemical Formula 1 according to one embodiment of the present specification has an increased light-emitting efficiency and lifespan compared to when only an anthracene compound is used as a blue host.

[0675] Through the experiments of Comparative Examples 2-4 and 2-5, it was found that the positions of the anthracene compound and the chrysene-containing compound in the light-emitting layer have a major influence on the device performance. If the B-5 compound with lower triplet energy exists in the region where holes and electrons combine, the generated triplet cannot transfer energy to X-7 with higher energy and is accumulated in B-5, which adversely affects the lifespan of the device.

[0676] Additionally, through the above Comparative Example 2-8, it was confirmed that in the case of a chrysene compound containing carbazole other than Chemical Formula 2 in Chemical Formula 1 of the present specification, the device performance was inferior to that of an organic light-emitting device containing Chemical Formula 1 of the present specification.

[0677] In addition, as shown in the results in Table 2 above, the excellent effect of increasing the lifespan by deuterium substitution was confirmed through comparative examples 2-4 and 2-9.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, At least one of R1 to R12 is the following chemical formula 2, and the remaining R1 to R12 that are not the following chemical formula 2 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, [Chemical Formula 2] In the above chemical formula 2, Y1 is O or S, L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, l1 is 1 or 2, and if l1 is 2, L1 are equal to or different from each other, G1 to G3 are the same or different and are each independently hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrene group substituted or unsubstituted with deuterium; or a heteroaryl group having 5 to 20 carbon atoms substituted or unsubstituted with deuterium. g1 to g3 are integers from 1 to 4, respectively, If the above g1 is 2 or more, the two or more G1 are equal to or different from each other, If the above g2 is 2 or more, the above 2 or more G2 are equal to or different from each other, If the above g3 is 2 or more, the two or more G3 are equal to or different from each other, m is 0 or 1, If the above m is 0, the above g2 is an integer from 1 to 4, and g1+g2≤7, If the above m is 1, the above g2 is 1 or 2, and g1+g2+g3≤9, is a portion that is bonded to the above chemical formula 1, The above chemical formula 1 contains at least one deuterium.

2. In claim 1, the substituted or unsubstituted aryl group; the substituted or unsubstituted heteroaryl group; the substituted or unsubstituted arylene group; the substituted or unsubstituted heteroarylene group; and the triplet energy level (T) of the chemical formula 2 s 1) A compound having an energy level higher than the triplet energy level of Chrysene.

3. In claim 1, the substituted or unsubstituted aryl group; the substituted or unsubstituted heteroaryl group; the substituted or unsubstituted arylene group; the substituted or unsubstituted heteroarylene group; and the triplet energy level (T) of the chemical formula 2 s 1) is below the triplet energy level of Chrysen, and the above T s 1 is a compound in which the difference from the triplet energy level of Chrysene is more than 0 eV and less than or equal to 0.2 eV.

4. In claim 1, the compound wherein the chemical formula 1 is any one of the following chemical formulas 1-1 to 1-6: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] In the above chemical formulas 1-1 to 1-6, The definitions of Y1, L1, l1, G1 to G3 and g1 to g3 are the same as those defined in the above chemical formula 2, R1 to R12 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, Y11 is O or S, L11 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, l11 is 1 or 2, and if l11 is 2, L11 are equal to or different from each other, G11 to G13 are the same as or different from each other, and are each independently hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrene group substituted or unsubstituted with deuterium; or a heteroaryl group having 5 to 20 carbon atoms substituted or unsubstituted with deuterium. g11 to g113 are integers from 1 to 4, respectively, If the above g11 is 2 or more, the two or more G11 are the same or different from each other, If the above g12 is 2 or more, the two or more G12 are the same or different from each other, If the above g13 is 2 or more, the two or more G13 are the same or different from each other, m' is 0 or 1, If the above m' is 0, the above g12 is an integer from 1 to 4, and g11+g12≤7, If the above m' is 1, the above g12 is 1 or 2, and g11+g12+g13≤9.

5. In claim 1, the compound wherein the chemical formula 2 is any one of the following chemical formulas 2-1 to 2-7: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] [Chemical Formula 2-5] [Chemical Formula 2-6] [Chemical Formula 2-7] In the above chemical formulas 2-1 to 2-7, The definitions of Y1, L1, l1, G1 to G3 and g1 to g3 are the same as those defined in the above chemical formula 2.

6. In claim 1, a compound wherein at least one of R1 to R12 is the chemical formula 2, and the remaining R1 to R12 that are not the chemical formula 2 are the same as or different from each other, and each independently represents hydrogen; deuterium; or a phenyl group unsubstituted or substituted with deuterium, a phenyl group, a biphenyl group, a naphthyl group, or a combination thereof; a biphenyl group unsubstituted or substituted with deuterium, a phenyl group, or a combination thereof; a terphenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium, a phenyl group, a naphthyl group, or a combination thereof; or a phenanthrene group unsubstituted or substituted with deuterium.

7. A compound according to claim 1, wherein L1 is a direct bond; a phenylene group unsubstituted or substituted with deuterium, a biphenyl group, a naphthyl group, or a combination thereof; a biphenylylene group unsubstituted or substituted with deuterium, a phenyl group, or a combination thereof; or a terphenylylene group unsubstituted or substituted with deuterium.

8. A compound according to claim 1, wherein G1 to G3 are the same as or different from each other, and are each independently hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrene group substituted or unsubstituted with deuterium; a benzofuran group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a benzothiophene group substituted or unsubstituted with deuterium; or a dibenzothiophene group substituted or unsubstituted with deuterium.

9. In claim 1, the compound having chemical formula 1 is any one of the following compounds:

10. Anode; cathode; and An organic light-emitting device comprising at least one organic layer provided between the anode and the cathode, An organic light-emitting device, wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 9.

11. An organic light-emitting device according to claim 10, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

12. An organic light-emitting device according to claim 11, wherein the light-emitting layer comprises the compound as a host.

13. An organic light-emitting device according to claim 11, wherein the light-emitting layer comprises the compound as a host and further comprises a dopant.

14. An organic light-emitting device according to claim 13, wherein the dopant is a compound of the following chemical formula D: [Chemical Formula D] In the above chemical formula D, X1 and X2 are the same or different from each other, and are each independently CR'; NR"; or O, and at least one of X1 and X2 is NR", A and C are the same or different and are each independently a substituted or unsubstituted 5-membered ring; or a substituted or unsubstituted 6-membered ring, R401, R' and R" are the same or different and each independently represent 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 aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring, r401 is an integer from 0 to 3, and when r401 is 2 or more, the 2 or more R401s are the same as or different from each other.

15. An organic light-emitting device according to claim 11, wherein the light-emitting layer comprises the compound as a first host and further comprises a second host.

16. An organic light-emitting device according to claim 15, wherein the second host is a compound of the following chemical formula H: [Chemical formula H] In the above chemical formula H, L20 and L21 are the same or different, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group, Ar20 and Ar21 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, 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, and when r301 is 2 or more, 2 or more R301 are the same as or different from each other.

17. An organic light-emitting device according to claim 11, wherein the light-emitting layer comprises the compound as a first host, further comprises a second host, and further comprises a dopant.

18. Anode; cathode; A first light-emitting layer provided between the anode and the cathode; and A second light-emitting layer is provided 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 a compound according to any one of claims 1 to 9, An organic light-emitting device wherein the second light-emitting layer comprises a compound of the following chemical formula H: [Chemical formula H] In the above chemical formula H, L20 and L21 are the same or different, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group, Ar20 and Ar21 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, 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, and when r301 is 2 or more, 2 or more R301 are the same as or different from each other.

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