Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound of Chemical Formula 1 and an organic light-emitting device comprising the same. The compound described in the specification can be used as a material for an organic layer of an organic light-emitting device. The compound according to at least one embodiment of the present specification can achieve an improvement in efficiency, a lower driving voltage, and / or an improvement in lifespan characteristics in an organic light-emitting device. In particular, the compound described in the specification can be used as a material for a light-emitting layer. Further, the organic light emitting device has the effects of low driving voltage, high efficiency, and / or long lifespan compared to an existing organic light emitting device.

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2023-0185692, filed with the Korean Patent Office on December 19, 2023, and Korean Patent Application No. 10-2024-0162613, filed with the Korean Patent Office on November 15, 2024, the entire contents of which are incorporated herein by reference.

[0002] This specification relates to a compound and an organic light-emitting device including the same. Background Art

[0003] Generally, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light-emitting device using the organic light-emitting phenomenon typically has a structure including an anode, a cathode, and an organic layer located therebetween. Here, in order to improve the efficiency and stability of the organic light-emitting device, the organic layer is mostly formed of a multilayer structure formed of different substances respectively. For example, it may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. For such a structure of the organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons return to the ground state again.

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

[0005] Prior Art Documents

[0006] Patent Documents

[0007] Korean Patent Publication No. 2000-0051826 Summary of the Invention

[0008] Technical Problem

[0009] This specification provides a compound and an organic light-emitting device including the same.

[0010] Solution to the Problem

[0011] One embodiment of this specification provides a compound of Chemical Formula 1 below.

[0012] [Chemical Formula 1]

[0013]

[0014] In Chemical Formula 1 above,

[0015] L is a phenylene group that is directly bonded, deuterium-substituted or unsubstituted, a biphenylene group that is deuterium-substituted or unsubstituted, or a divalent terphenyl group that is deuterium-substituted or unsubstituted.

[0016] Ar1 is a phenyl group that is deuterium-substituted or unsubstituted, a biphenyl group that is deuterium-substituted or unsubstituted, or a terphenyl group that is deuterium-substituted or unsubstituted.

[0017] m is an integer from 0 to 3.

[0018] m' is an integer from 1 to 3.

[0019] n is an integer from 0 to 3.

[0020] n' is an integer from 1 to 3.

[0021] m” is an integer from 0 to 3.

[0022] n” is an integer from 0 to 3.

[0023] m” + n” is an integer from 1 to 3.

[0024] When each of the above m” and n” is 2 or more, the structures in the above two or more parentheses are the same or different.

[0025] D is deuterium.

[0026] Each of x1 to x6 is an integer from 0 to 4.

[0027] Each of x'5 and x'6 is an integer from 0 to 5.

[0028] In the above Chemical Formula 1 the deuterium substitution rate is 50% or more.

[0029] * is the site bonded to the above L.

[0030] In addition, one embodiment of the present specification provides an organic light-emitting device, which includes: a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, and one or more of the organic layers contain the above compound.

[0031] Advantages of the Invention

[0032] The compounds described in the present specification can be used as materials for the organic layers of organic light-emitting devices. The compounds according to at least one embodiment of the present specification can achieve an improvement in efficiency, a lower driving voltage, and / or an improvement in lifetime characteristics in organic light-emitting devices. In particular, the compounds described in the present specification can be used as materials for the light-emitting layer. In addition, compared with existing organic light-emitting devices, it has the effects of low driving voltage, high efficiency, and / or long lifetime. Brief Description of the Drawings

[0033] Figure 1 and 2 illustrates an example of an organic light emitting device according to an embodiment of the present specification.

[0034] Figure 3 is the MS chart of Compound A.

[0035] Symbol Explanation

[0036] 1: Substrate

[0037] 2: First Electrode

[0038] 3: Second Electrode

[0039] 4: Organic Layer

[0040] 5: Hole Injection Layer

[0041] 6: Hole Transport Layer

[0042] 7: Electron Blocking Layer

[0043] 8: Light Emitting Layer

[0044] 9: Hole Blocking Layer

[0045] 10: Electron Injection and Transport Layer Detailed Embodiment

[0046] Hereinafter, the present specification will be described in more detail.

[0047] The present specification provides the compound of Chemical Formula 1 above.

[0048] The Chemical Formula 1 according to an embodiment of the present specification includes a dicarbazole structure to increase the LUMO energy level of the compound, thereby preventing the host-guest electrostatic coupling state of the organic layer of the organic light emitting device including the same. In addition, the monocyclic aryl group and L-Ar1 bonded to a specific position of the dicarbazole participate in the conjugation system through the hyperconjugation effect, thereby having a structural feature of stabilizing the excited and polaronic states of Chemical Formula 1 above. Therefore, Chemical Formula 1 above is included in the organic layer of the organic light emitting device to achieve an improvement in efficiency, a lower driving voltage, and an improvement in lifetime characteristics.

[0049] In addition, physicochemical properties such as the bond length related to deuterium are different from those of hydrogen. Compared with the C-H bond, the stretching amplitude of the C-D bond is smaller, so the van der Waals radius of deuterium is smaller than that of hydrogen. Generally, it can be shown that the C-D bond is shorter and stronger than the C-H bond. Therefore, in Chemical Formula 1 above The deuterium substitution rate is 50% or more. Therefore, the energy of the ground state is reduced, the bond length between deuterium and carbon becomes shorter, and thus the molecular hardcore volume shrinks. As a result, the electrical polarizability can be decreased, and the intermolecular interaction can be weakened, thereby increasing the film volume. In addition, such characteristics can create an effect of reducing the crystallinity of the film, that is, an amorphous state, which can generally effectively improve the lifespan and driving characteristics of the organic light-emitting device, and the heat resistance can be further improved compared with existing organic light-emitting devices.

[0050] In this specification, examples of substituents are described below, but are not limited thereto.

[0051] In this specification, represents the connected part.

[0052] The term "substituted" as mentioned above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The position to be substituted is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can substitute. When two or more are substituted, the two or more substituents may be the same or different from each other.

[0053] In this specification, the term "substituted or unsubstituted" means being substituted by one or more substituents selected from deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, a haloalkyl group, a silyl group, a boron group, an amino group, an aryl group, a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and a heteroaryl group, or being substituted by a substituent formed by connecting two or more of the above-exemplified substituents, or having no substituent.

[0054] In this specification, the connection of two or more substituents means that the hydrogen of any one substituent is connected to another substituent. For example, the connection of two substituents can be the connection of a phenyl group and a naphthyl group to form such a substituent. In addition, the connection of three substituents includes not only the continuous connection of (substituent 1)-(substituent 2)-(substituent 3), but also the connection of (substituent 2) and (substituent 3) to (substituent 1). For example, the connection of a phenyl group, a naphthyl group, and an isopropyl group can form such a substituent. The same definition applies to the connection of four or more substituents.

[0055] In this specification, examples of the halogen group include a fluorine group, a chlorine group, a bromine group, or an iodine group.

[0056] In this specification, the alkyl group may be linear or branched, and there is no particular limitation on the number of carbon atoms, but it is preferably 1 to 30. As specific examples, there are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto.

[0057] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc., but are not limited thereto.

[0058] In this specification, the alkoxy group may be linear, branched or cyclic. There is no particular limitation on the number of carbon atoms of the alkoxy group, but it is preferably 1 to 30 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but are not limited thereto.

[0059] In this specification, the alkenyl group may be linear or branched, and there is no particular limitation on the number of carbon atoms, but it is preferably 2 to 30. As specific examples, there are vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthalen-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, styryl, etc., but are not limited thereto.

[0060] In this specification, the haloalkyl group means an alkyl group in which at least one halogen group replaces the hydrogen in the definition of the above alkyl group.

[0061] In this specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the above-mentioned aryl group may be monocyclic or polycyclic.

[0062] When the above-mentioned aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms. Specifically, as the monocyclic aryl group, it may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

[0063] When the above-mentioned aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 10 to 30 carbon atoms. Specifically, as the polycyclic aryl group, it may be a naphthyl group, an anthryl group, a phenanthryl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a fluorenyl group, etc., but is not limited thereto.

[0064] In this specification, the above-mentioned fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0065] Examples of the above-mentioned fluorenyl group include

[0066] etc., but are not limited thereto.

[0067] In this specification, "adjacent" groups may refer to substituents substituted on atoms directly connected to the atom substituted by the substituent, substituents that are closest in steric structure to the substituent, or other substituents substituted on the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0068] In this specification, the heteroaryl group contains one or more non-carbon atoms, i.e., heteroatoms. Specifically, the above-mentioned heteroatoms may contain one or more atoms selected from O, N, Se, S, etc. The number of carbon atoms is not particularly limited, but preferably 2 to 30 carbon atoms, and the above-mentioned heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, a dioxazolyl group, a pyridyl group, a bipyridyl group, a pyrimidinyl group, a triazinyl group, a triazolyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl group, an indolyl group, a carbazolyl group, a benzo oxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuryl group, a phenanthridine group, a phenanthroline group, an iso Azolyl, thiadiazolyl, dibenzofuranyl, dibenzosilolyl, phenoxathiine, phenoxazine, phenothiazine, indeno[1,2-c]carbazolyl, spirofluorene xanthenyl, spirofluorene thioxanthenyl, etc., but not limited thereto. Phenoxathiine Phenoxazine, phenothiazine, indeno[1,2-c]carbazolyl, spirofluorene xanthenyl, spirofluorene thioxanthenyl, etc., but not limited thereto.

[0069] In this specification, silyl may be alkylsilyl, arylsilyl, heteroarylsilyl, etc. The alkyl in the above alkylsilyl may be exemplified by the above alkyl, the aryl in the above arylsilyl may be exemplified by the above aryl, and the heteroaryl in the above heteroarylsilyl may be exemplified by the above heteroaryl.

[0070] In this specification, the boron group may be -BR 100 R 101 wherein the above R 100 and R 101 are the same or different and each independently may be selected from hydrogen, deuterium, halogen, nitrile group, substituted or unsubstituted monocyclic or polycyclic cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted straight-chain or branched-chain alkyl having 1 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms, and substituted or unsubstituted monocyclic or polycyclic heteroaryl having 2 to 30 carbon atoms. Specific examples of the above boron group include dimethylboron group, diethylboron group, tert-butylmethylboron group, diphenylboron group, etc., but not limited thereto.

[0071] In this specification, the amino group may be selected from -NH2, alkylamino group, N-alkylarylamino group, arylamino group, N-arylheteroarylamino group, N-alkylheteroarylamino group, and heteroarylamino group, and the number of carbon atoms is not particularly limited, but preferably 1 to 30. Specific examples of the amino group include methylamino group, dimethylamino group, ethylamino group, diethylamino group, phenylamino group, naphthylamino group, biphenylamino group, anthrylamino group, 9-methyl-anthrylamino group, diphenylamino group, xylidino group, N-phenyltoluidino group, N-phenylbiphenylamino group, N-phenylnaphthylamino group, N-biphenylnaphthylamino group, N-naphthylfluorenylamino group, N-phenylphenanthrylamino group, N-biphenylphenanthrylamino group, N-phenylfluorenylamino group, N-phenylterphenylamino group, N-phenanthrylfluorenylamino group, N-biphenylfluorenylamino group, etc., but not limited thereto.

[0072] In this specification, the N-alkylarylamino group means an amino group in which an alkyl group and an aryl group are substituted on the N of the amino group. The alkyl group and the aryl group in the above N-alkylarylamino group are the same as the examples of the above alkyl group and aryl group.

[0073] In this specification, an N-aryl heteroaryl amino group refers to an amino group in which an aryl group and a heteroaryl group are substituted on the N of the amino group. The aryl group and the heteroaryl group in the above N-aryl heteroaryl amino group are the same as the examples of the aryl group and the heteroaryl group described above.

[0074] In this specification, an N-alkyl heteroaryl amino group refers to an amino group in which an alkyl group and a heteroaryl group are substituted on the N of the amino group. The alkyl group and the heteroaryl group in the above N-alkyl heteroaryl amino group are the same as the examples of the alkyl group and the heteroaryl group described above.

[0075] In this specification, as examples of the aryl amino group, there are substituted or unsubstituted monoaryl amino groups, or substituted or unsubstituted diaryl amino groups. The aryl amino group containing two or more of the above aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the above aryl amino group may be selected from the examples of the aryl group described above.

[0076] In this specification, as examples of the heteroaryl amino group, there are substituted or unsubstituted monoheteroaryl amino groups, or substituted or unsubstituted diheteroaryl amino groups. The heteroaryl amino group containing two or more of the above heteroaryl groups may contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or may contain both a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the above heteroaryl amino group may be selected from the examples of the heteroaryl group described above.

[0077] In this specification, the hydrocarbon ring group may be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring. The above aromatic hydrocarbon ring group applies to the description of the above aryl group, and the aliphatic hydrocarbon ring group may apply to the description of the above cycloalkyl group. In addition, the fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring may apply to the structure in which the above aryl group and cycloalkyl group are fused to each other.

[0078] In this specification, an arylene group refers to a group having two bonding positions on the aryl group, that is, a divalent group. Except that they are each divalent groups, the description of the above aryl group may be applied.

[0079] In this specification, unless otherwise defined, all technical terms and scientific terms used in this specification have the same meanings as those commonly understood by those skilled in the art. Methods and materials similar or equivalent to those described in this specification may be used in the implementation or testing of the embodiments of the present invention, but suitable methods and materials are described hereinafter. All publications, patent applications, patents, and other references mentioned in this specification are incorporated herein by reference in their entirety. In case of conflict, if no specific passage is mentioned, this specification including the definitions shall prevail. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.

[0080] Next, the compound of the above Chemical Formula 1 will be described in detail.

[0081] [Chemical Formula 1-1]

[0082]

[0083] In the above Chemical Formula 1-1,

[0084] Ar1, D, m, m', m'', n, n', n'', x'5, x'6, and x1 to x6 are defined in the same manner as in the above Chemical Formula 1.

[0085] According to one embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-2 to 1-5.

[0086] [Chemical Formula 1-2]

[0087]

[0088] [Chemical Formula 1-3]

[0089]

[0090] [Chemical Formula 1-4]

[0091]

[0092] [Chemical Formula 1-5]

[0093]

[0094] In the above Chemical Formulas 1-2 to 1-5,

[0095] L, Ar1, D, m, m', m'', n, n', n', x'5, x'6, and x1 to x6 are defined in the same manner as in the above Chemical Formula 1.

[0096] According to one embodiment of the present specification, the above L is a phenyl group which may or may not be substituted with deuterium, a biphenyl group which may or may not be substituted with deuterium, or a divalent terphenyl group which may or may not be substituted with deuterium, and the above Ar1 is a phenyl group which may or may not be substituted with deuterium, a biphenyl group which may or may not be substituted with deuterium, or a terphenyl group which may or may not be substituted with deuterium.

[0097] According to one embodiment of the present specification, the above L is a direct bond, and the above Ar1 is a phenyl group which may or may not be substituted with deuterium, a biphenyl group which may or may not be substituted with deuterium, or a terphenyl group which may or may not be substituted with deuterium.

[0098] According to one embodiment of the present specification, the above L-Ar1 is a six-membered monocyclic aryl group having 6 to 18 carbon atoms which may or may not be substituted with deuterium.

[0099] According to an embodiment of the present specification, the above L-Ar1 is a phenyl group which may or may not be substituted with deuterium, a biphenyl group which may or may not be substituted with deuterium, or a terphenyl group which may or may not be substituted with deuterium.

[0100] According to an embodiment of the present specification, the above L-Ar1 is any one of the following structures.

[0101]

[0102] In the above structures,

[0103] D is deuterium,

[0104] x11, x12, and x13 are each an integer from 0 to 5, and x'11 and x'12 are each an integer from 0 to 4,

[0105] x”11 is an integer from 0 to 3,

[0106] is the site where the above L binds to the N of the biscarbazole of the above Chemical Formula 1.

[0107] When L-Ar1 according to an embodiment of the present specification has the above structure, it participates in the conjugated system through hyperconjugation, and thus has a structural feature that stabilizes the excited state and polarized state of the above Chemical Formula 1.

[0108] According to an embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 2 to 5.

[0109] [Chemical Formula 2]

[0110]

[0111] [Chemical Formula 3]

[0112]

[0113] [Chemical Formula 4]

[0114]

[0115] [Chemical Formula 5]

[0116]

[0117] In the above Chemical Formulas 2 to 5,

[0118] the definitions of D, m, m', m”, n, n', n”, x'5, x'6, and x1 to x6 are the same as those in the above Chemical Formula 1,

[0119] x11, x12, and x13 are each an integer from 0 to 5.

[0120] x'11 and x'12 are each an integer from 0 to 4.

[0121] x”11 is an integer from 0 to 3.

[0122] According to one embodiment of the present specification, the above m is 0.

[0123] According to one embodiment of the present specification, the above m is 1.

[0124] According to one embodiment of the present specification, the above m is 2.

[0125] According to one embodiment of the present specification, the above m is 3.

[0126] According to one embodiment of the present specification, the above n is 0.

[0127] According to one embodiment of the present specification, the above n is 1.

[0128] According to one embodiment of the present specification, the above n is 2.

[0129] According to one embodiment of the present specification, the above n is 3.

[0130] According to one embodiment of the present specification, the above m' is 1.

[0131] According to one embodiment of the present specification, the above m' is 2.

[0132] According to one embodiment of the present specification, the above m' is 3.

[0133] According to one embodiment of the present specification, the above n' is 1.

[0134] According to one embodiment of the present specification, the above n' is 2.

[0135] According to one embodiment of the present specification, the above n' is 3.

[0136] According to one embodiment of the present specification, the above m” + n” = 1.

[0137] According to one embodiment of the present specification, the above m” + n” = 2.

[0138] According to one embodiment of the present specification, the above m” is 1 and n” is 0.

[0139] According to one embodiment of the present specification, the above m” is 0 and n” is 1.

[0140] According to one embodiment of the present specification, the above m” is 1 and n” is 2.

[0141] According to an embodiment of the present specification, the above m” is 1 and n” is 3.

[0142] According to an embodiment of the present specification, the above is any one of the following structures.

[0143]

[0144] In the above structure,

[0145] D is deuterium,

[0146] x'5 and x””5 are each an integer from 0 to 5,

[0147] x5 and x”5 are each an integer from 0 to 4,

[0148] x”'5 is an integer from 0 to 3,

[0149] ** is a moiety bonded to any one of the positions 1 to 8 of the bis-carbazole of the above Chemical Formula 1.

[0150] According to an embodiment of the present specification, the above is any one of the following structures.

[0151]

[0152] In the above structure, D is deuterium,

[0153] x'6 and x””6 are each an integer from 0 to 5,

[0154] x6 and x”6 are each an integer from 0 to 4,

[0155] x”'6 is an integer from 0 to 3,

[0156] *** is a moiety bonded to any one of the positions 1' to 8' of the bis-carbazole of the above Chemical Formula 1.

[0157] In the present specification, the positions 1 to 8 and 1' to 8' of the bis-carbazole are as shown below.

[0158]

[0159] According to an embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-6 to 1-10.

[0160] [Chemical Formula 1-6]

[0161]

[0162] [Chemical Formula 1-7]

[0163]

[0164] [Chemical Formula 1-8]

[0165]

[0166] [Chemical Formula 1-9]

[0167]

[0168] [Chemical Formula 1-10]

[0169]

[0170] In the above Chemical Formulas 1-6 to 1-10,

[0171] L, Ar1, D, x1 to x4, x'5 and x'6 are defined in the same way as in Chemical Formula 1 above.

[0172] According to an embodiment of this specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-4-1 to 1-4-11.

[0173] [Chemical Formula 1-4-1]

[0174]

[0175] [Chemical Formula 1-4-2]

[0176]

[0177] [Chemical Formula 1-4-3]

[0178]

[0179] [Chemical Formula 1-4-4]

[0180]

[0181] [Chemical Formula 1-4-5]

[0182]

[0183] [Chemical Formula 1-4-6]

[0184]

[0185] [Chemical Formula 1-4-7]

[0186]

[0187] [Chemical Formula 1-4-8]

[0188]

[0189] [Chemical Formula 1-4-9]

[0190]

[0191] [Chemical Formula 1-4-10]

[0192]

[0193] [Chemical Formula 1-4-11]

[0194]

[0195] In the above Chemical Formulas 1-4-1 to 1-4-11,

[0196] L, Ar1, D, x1 to x4, x'5 and x'6 are defined in the same way as in Chemical Formula 1 above.

[0197] According to an embodiment of this specification, for the above Chemical Formula 1 the deuterium substitution rate is 50% to 93.33%.

[0198] According to an embodiment of this specification, for the above Chemical Formula 1 the deuterium substitution rate is 53.33% to 93.33%.

[0199] According to an embodiment of this specification, the deuterium substitution rate of the above Chemical Formula 1 is 22.22% to 100%.

[0200] According to an embodiment of this specification, the deuterium substitution rate of the above Chemical Formula 1 is 38.88% to 100%.

[0201] According to an embodiment of this specification, the deuterium substitution rate of the above Chemical Formula 1 is 50% to 100%.

[0202] According to an embodiment of this specification, physicochemical properties such as the bond length of the chemical bond related to deuterium are different from those of hydrogen. Compared with the C-H bond, the stretching amplitude of the C-D bond is smaller. Therefore, the van der Waals radius of deuterium is smaller than that of hydrogen. Usually, it can be shown that the C-D bond is shorter and stronger than the C-H bond. Therefore, for the above Chemical Formula 1 The deuterium substitution rate is 50% or more. Therefore, the energy of the ground state is reduced, the bond length between deuterium and carbon becomes shorter, and thus the molecular nuclear volume shrinks. As a result, the electric polarizability can be reduced, and the intermolecular interaction can be weakened, thereby increasing the film volume. In addition, such characteristics can create an effect of reducing the crystallinity of the film, that is, the amorphous state, which can generally effectively improve the lifespan and driving characteristics of the organic light-emitting device, and the heat resistance can be further improved compared with the existing organic light-emitting devices.

[0203] In this specification, "deuterium substitution", "containing deuterium", "deuteration" or "deuterated" means that the hydrogen at the substitutable position of a compound is replaced by deuterium.

[0204] In this specification, "perdeuterated" means a compound or group in which all the hydrogen in the molecule is replaced by deuterium, and has the same meaning as "100% deuterated".

[0205] In this specification, "X% deuterated", "deuteration degree X%", or "deuterium substitution rate X%" means that X% of the hydrogen at the substitutable position in the structure is replaced by deuterium. For example, when the structure is dibenzofuran, "25% deuterated" dibenzofuran, "deuteration degree 25%" of the above dibenzofuran, or "deuterium substitution rate 25%" of the above dibenzofuran means that 2 out of 8 hydrogens at the substitutable position of the above dibenzofuran are replaced by deuterium.

[0206] In this specification, the "deuteration degree" or "deuterium substitution rate" can be confirmed by well-known methods such as nuclear magnetic resonance spectroscopy ( 1 HNMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry).

[0207] Specifically, when analyzing the "deuteration degree" or "deuterium substitution rate" by nuclear magnetic resonance spectroscopy ( 1 H NMR), DMF (dimethylformamide) can be added as an internal standard, and the deuteration degree or deuterium substitution rate can be calculated from the integrated amount of the total peak through the integration ratio on 1 H NMR.

[0208] In addition, when analyzing the "deuteration degree" or "deuterium substitution rate" by TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), the substitution rate can be calculated based on the maximum value (median) of the distribution formed by the molecular weight at the end of the reaction. For example, when analyzing the deuteration degree of the following compound A, the molecular weight of the following starting material is 506, and when it is indicatedFigure 3 When the maximum (median) molecular weight of the following Compound A in the MS chart is 527, 21 out of 26 replaceable hydrogen atoms at the replaceable positions of the following starting materials are replaced with deuterium, so it can be calculated that approximately 81% of the hydrogen is deuterated.

[0209]

[0210] In this specification, D represents deuterium.

[0211] According to one embodiment of this specification, the above Chemical Formula 1 is any one of the following compounds.

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231] In addition, this specification provides an organic light-emitting device including the above-mentioned compound.

[0232] In this specification, when it is indicated that a certain member is "on" another member, it includes not only the case where a certain member is in contact with another member, but also the case where there are other members between the two members.

[0233] In this specification, when it is indicated that a certain part "includes" a certain constituent element, unless there is a particularly contrary description, it means that other constituent elements can be further included, rather than excluding other constituent elements.

[0234] In this specification, the above-mentioned "layer" is interchangeable with the "film" mainly used in this technical field, and refers to a coating covering a target area. The size of the above-mentioned "layer" is not limited, and the sizes of each "layer" can be the same or different. According to an embodiment, the size of the "layer" can be equal to the entire device, can be equivalent to the size of a specific functional area, or can be as small as a single sub-pixel.

[0235] In this specification, the meaning that a specific substance A is included in layer B includes both cases of i) one or more substances A being included in a single layer of layer B, and ii) layer B being composed of one or more layers and one or more substances A being included in one or more of the multiple layers of layer B.

[0236] In this specification, the meaning that a specific substance A is included in layer C or layer D refers to all of the following cases: i) the case of being included in one or more of one or more layers of layer C, or ii) the case of being included in one or more of one or more layers of layer D, or iii) the case of being respectively included in one or more of one or more layers of layer C and one or more of one or more layers of layer D.

[0237] In this specification, "n-type" refers to a substance in which the matrix material (the material of the organic layer) can take electrons, and commonly known substances can be used, and it is not limited thereto. That is, "n-type" can be defined as a substance having the property of being able to supply electrons to the LUMO (lowest unoccupied molecular orbital) energy level of the matrix. On the contrary, "p-type" refers to the following substances: when a layer is composed only of p-type substances, it receives electrons from the HOMO (highest occupied molecular orbital) energy level of the substance in the direction of the adjacent cathode, and generates holes in the substance in the direction of the adjacent cathode; or when a p-type substance is doped in any matrix, it receives electrons from the HOMO of the matrix material, and generates an equal amount of holes in the HOMO of the matrix. For this reason, when a layer is formed only of p-type substances, the closer the HOMO of the substance in the cathode direction is to the LUMO of the p-type substance, the easier it is to take electrons from the HOMO of the adjacent layer, and the easier it is to generate holes in the HOMO of the adjacent layer. In addition, when a p-type substance is doped in any matrix, the closer the LUMO of the p-type substance is to the HOMO of the matrix, the easier it is to take electrons, and the easier it is to generate holes in the matrix.

[0238] This specification provides an organic light-emitting device, which includes: a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, and one or more of the organic layers contain the compound of Chemical Formula 1.

[0239] The organic layer of the organic light-emitting device of this specification can be formed in a single-layer structure or in a multi-layer structure in which two or more organic layers are stacked. For example, it can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited thereto, and it can include a smaller number of organic layers.

[0240] According to an embodiment of this specification, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer contains the above compound.

[0241] According to an embodiment of this specification, the organic layer includes an electron blocking layer, and the electron blocking layer contains the above compound.

[0242] According to an embodiment of this specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer.

[0243] According to an embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound.

[0244] According to an embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound as the host of the light-emitting layer.

[0245] According to an embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound as the p-type host of the light-emitting layer.

[0246] According to an embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound as the p-type phosphorescent host of the light-emitting layer.

[0247] According to an embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound as the host and further contains other hosts.

[0248] According to an embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound as the host and further contains a host and a dopant.

[0249] According to an embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound as the first host and further contains a second host.

[0250] According to an embodiment of the present specification, the first host is a p-type host, and the second host is an n-type host.

[0251] According to an embodiment of the present specification, the first host is a p-type phosphorescent host, and the second host is an n-type phosphorescent host.

[0252] According to an embodiment of the present specification, the light-emitting layer contains the first host and the second host in a weight ratio of 2:8 to 8:2, and the first host is the compound of Chemical Formula 1.

[0253] According to an embodiment of the present specification, the light-emitting layer contains the first host and the second host in a weight ratio of 1:1, and the first host is the compound of Chemical Formula 1.

[0254] According to an embodiment of the present specification, the second host is a dibenzofuran-based compound.

[0255] According to an embodiment of the present specification, the second host is the following Chemical Formula HB-1.

[0256] According to an embodiment of the present specification, the second host is a dibenzofuran-based compound substituted with a triazinyl group substituted with a carbazolyl group.

[0257] According to an embodiment of the present specification, the above-mentioned light-emitting layer further includes a dopant.

[0258] According to an embodiment of the present specification, the above-mentioned light-emitting layer includes a first host and a second host, and further includes a dopant.

[0259] According to an embodiment of the present specification, the above-mentioned dopant is a phosphorescent dopant.

[0260] According to an embodiment of the present specification, relative to 100 parts by weight of the host, the above-mentioned dopant includes 1 to 20 parts by weight.

[0261] According to an embodiment of the present specification, the above-mentioned light-emitting layer includes a dopant, and the above-mentioned dopant includes a phosphorescent dopant.

[0262] According to an embodiment of the present specification, the above-mentioned organic layer includes a light-emitting layer, the above-mentioned light-emitting layer includes a host and a dopant, the above-mentioned host includes the above-mentioned compound, and the above-mentioned dopant includes the above-mentioned phosphorescent dopant.

[0263] According to an embodiment of the present specification, the above-mentioned light-emitting layer is a blue light-emitting layer.

[0264] According to an embodiment of the present specification, the maximum emission wavelength of the above-mentioned light-emitting layer is 420 nm to 495 nm.

[0265] According to an embodiment of the present specification, the above-mentioned light-emitting layer includes a host and a dopant in a weight ratio of 99:1 to 1:99. Specifically, it includes a host and a dopant in a weight ratio of 99:1 to 50:50, and more specifically, in a weight ratio of 99:1 to 95:5.

[0266] When the above-mentioned light-emitting layer emits red light, as the light-emitting dopant, 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), etc. can be used; or fluorescent materials such as Alq3 (tris(8-hydroxyquinolino)aluminum), etc., but not limited thereto. When the light-emitting layer emits green light, as the light-emitting dopant, phosphorescent materials such as Ir(ppy)3 (fac tris(2-phenylpyridine)iridium), etc. or fluorescent materials such as Alq3 (tris(8-hydroxyquinoline)aluminum), etc. can be used, but not limited thereto. When the light-emitting layer emits blue light, as the light-emitting dopant, platinum coordination compounds, phosphorescent materials such as (4,6-F2ppy)2Irpic, etc. can be used; or fluorescent materials such as spiro-DPVBi, spiro-6P, divinylbenzene (DSB), divinylarylene (DSA), PFO-based polymers, PPV-based polymers, etc., but not limited thereto.

[0267] According to an embodiment of the present specification, the above dopant is a metal coordination compound.

[0268] According to an embodiment of the present specification, the above dopant is a platinum coordination compound.

[0269] According to an embodiment of the present specification, the above dopant is an iridium coordination compound.

[0270] According to an embodiment of the present specification, the above dopant is represented by the following chemical formula D-1 or D-2, but not limited thereto.

[0271] [Chemical formula D-1]

[0272]

[0273] [Chemical formula D-2]

[0274]

[0275] In the above chemical formulas D-1 and D-2,

[0276] M is a transition metal,

[0277] A1, A3, A5, A6, K1, K2, and K3 are the same as or different from each other, and are each independently a direct bond, O, S, a divalent ester group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted divalent alkenyl group, a substituted or unsubstituted divalent allyl group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0278] A2 and A4 are the same as or different from each other, and are each independently a direct bond, N, a substituted or unsubstituted trivalent alkylene group, a substituted or unsubstituted trivalent aryl group, or a substituted or unsubstituted trivalent heteroaryl group,

[0279] n is 1 or 2. When the above n is 2, the structures in the parentheses are the same as or different from each other.

[0280] According to an embodiment of the present specification, the above M is iridium or platinum.

[0281] According to an embodiment of the present specification, the above dopant may be selected from the following structural formulas, but is not limited thereto.

[0282]

[0283]

[0284]

[0285]

[0286] According to an embodiment of the present specification, the above organic layer includes an electron blocking layer.

[0287] According to an embodiment of the present specification, the above organic layer further includes one or more layers selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.

[0288] According to an embodiment of the present specification, the above organic light emitting device further includes one or two or more layers selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0289] According to an embodiment of the present specification, the above organic light-emitting device includes a first electrode; a second electrode disposed opposite to the first electrode; a light-emitting layer disposed between the first electrode and the second electrode; and two or more organic layers disposed between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode.

[0290] According to an embodiment of the present specification, the two or more organic layers may be selected from two or more of the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0291] According to an embodiment of the present specification, two or more hole transport layers are included between the light-emitting layer and the first electrode. The two or more hole transport layers may contain the same or different substances from each other.

[0292] According to an embodiment of the present specification, the first electrode is an anode or a cathode.

[0293] According to an embodiment of the present specification, the second electrode is a cathode or an anode.

[0294] According to an embodiment of the present specification, the above 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.

[0295] According to an embodiment of the present specification, the above organic light-emitting device may be an organic light-emitting device having an inverted structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0296] For example, a structural example of an organic light-emitting device according to an embodiment of the present specification is illustrated in Figure 1 and 2 . The above Figure 1 and 2 illustrate an organic light-emitting device and are not limited thereto.

[0297] Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode 2, an organic layer 4, and a second electrode 3 are sequentially stacked on a substrate 1. The above compound is included in the organic layer.

[0298] Figure 2The structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 10, and a second electrode 3 are sequentially stacked on a substrate 1 is illustrated. The above compound is contained in the electron blocking layer 7 and / or the light-emitting layer 8.

[0299] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that the electron blocking layer and / or the light-emitting layer contain the above compound, that is, the compound of Chemical Formula 1 above.

[0300] When the above organic light-emitting device includes a plurality of organic layers, the above organic layers may be formed of the same substance or different substances.

[0301] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be manufactured as follows: using a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is evaporated on the substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is evaporated on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate.

[0302] In addition, the compound of Chemical Formula 1 above can form an organic layer not only by a vacuum evaporation method but also by a solution coating method when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

[0303] In addition to these methods, an organic light-emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate. However, the manufacturing method is not limited thereto.

[0304] As the above anode substance, in order to smoothly inject holes into the organic layer, a substance having a large work function is generally preferred. For example, metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but is not limited thereto.

[0305] As the above-mentioned cathode material, generally, in order to facilitate the injection of electrons into the organic layer, a material with a small work function is preferred. For example, there are metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multi-layer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0306] The above-mentioned light-emitting layer may include a host material and a dopant material. When the organic light-emitting device according to an embodiment of the present specification includes an additional light-emitting layer in addition to the light-emitting layer containing the above chemical formula 1, the host material includes aromatic condensed ring derivatives or heterocyclic compounds, etc. Specifically, as the aromatic condensed ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as the heterocyclic compounds, there are dibenzofuran derivatives, ladder-type furan compounds pyrimidine derivatives, etc., but are not limited thereto.

[0307] As the above-mentioned dopant material, there are aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivatives are aromatic condensed ring derivatives having a substituted or unsubstituted arylamino group, and there are pyrene, anthracene, dindenoanthracene, etc. having an arylamino group. In addition, the styryl amine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styryl amine, styryldiamine, styryltriamine, styryl tetramine, etc., but are not limited thereto. In addition, as the metal complex, there are iridium complexes, platinum complexes, etc., but are not limited thereto.

[0308] The above-mentioned hole injection layer is a layer that receives holes from the electrode. The hole injection material is preferably a material having the ability to transport holes, having the effect of receiving holes from the anode, and having an excellent hole injection effect on the light-emitting layer or the light-emitting material. In addition, it is preferably a material having an excellent ability to prevent the migration of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material. Moreover, it is preferably a material having excellent thin film forming ability. In addition, it is preferred that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic compounds; hexanitrile hexaazatriphenylene-based organic compounds; quinacridone-based organic compounds; perylene-based organic compounds; anthraquinone, polyaniline, and polythiophene-based conductive polymers, etc., but are not limited thereto.

[0309] According to an embodiment of the present specification, the above hole injection layer contains a compound represented by the following chemical formula HI-1, but is not limited thereto.

[0310] [Chemical formula HI-1]

[0311]

[0312] In the above chemical formula HI-1,

[0313] R315 to R317 are the same as or different from each other, and each independently is any one selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or combine with adjacent groups to form a substituted or unsubstituted ring.

[0314] r315 is an integer from 1 to 5. When the above r315 is 2 or more, two or more of the above R315 are the same as or different from each other.

[0315] r316 is an integer from 1 to 5. When the above r316 is 2 or more, two or more of the above R316 are the same as or different from each other.

[0316] According to an embodiment of the present specification, the above R317 is any one selected from substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof.

[0317] According to an embodiment of the present specification, the above R317 is any one selected from carbazolyl, phenyl, biphenyl, triphenylene, and combinations thereof.

[0318] According to an embodiment of the present specification, the above R315 and R316 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl, or combines with adjacent groups to form an aromatic hydrocarbon ring substituted with an aryl or an alkyl.

[0319] According to an embodiment of the present specification, the above R315 and R316 are the same as or different from each other, and each independently is phenyl or biphenyl, or combines with adjacent groups to form an indene substituted with phenyl or methyl.

[0320] According to an embodiment of the present specification, the above chemical formula HI-1 is represented by any one of the following compounds.

[0321]

[0322]

[0323] According to an embodiment of the present specification, the above hole injection layer contains a compound represented by the following chemical formula HI-2, but is not limited thereto.

[0324] [Chemical formula HI-2]

[0325]

[0326] In the above chemical formula HI-2,

[0327] R401 to R403 are the same as or different from each other, and each independently is a halogen group.

[0328] r401 to r403 are 4.

[0329] According to an embodiment of the present specification, the above R401 to R403 are F.

[0330] According to an embodiment of the present specification, the above chemical formula HI-2 is represented by the following compound.

[0331]

[0332] According to an embodiment of the present specification, the above hole injection layer contains the above chemical formulas HI-1 and HI-2.

[0333] According to an embodiment of the present specification, the above hole injection layer contains the above chemical formulas HI-1 and HI-2 in a weight ratio of 1:99 to 99:1.

[0334] The above hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and is preferably a material with a large hole mobility. As a specific example, there are arylamine-based organic compounds, conductive polymers, and block copolymers having both a conjugated part and a non-conjugated part, etc., but are not limited thereto.

[0335] According to an embodiment of the present specification, the above hole transport layer contains a compound represented by the above chemical formula HI-1, but is not limited thereto.

[0336] According to an embodiment of the present specification, the above hole injection and transport layer is a layer that transports holes to the light-emitting layer. The materials exemplified in the above hole transport layer and hole injection layer can be used, but are not limited thereto.

[0337] The above-mentioned electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. The electron transport material is a material that can receive electrons well from the cathode and transfer them to the light-emitting layer, and is preferably a material with a large electron mobility. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used together with any desired cathode material as used in the prior art. In particular, suitable cathode materials are common materials with a low work function and accompanied by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, etc., each accompanied by an aluminum layer or a silver layer in each case.

[0338] The above-mentioned electron injection layer is a layer that receives electrons from the electrode. As the electron injection material, preferably, it is a material with excellent electron transport ability, having the effect of receiving electrons from the second electrode, and having an excellent electron injection effect on the light-emitting layer or the light-emitting material. In addition, it is preferably a material that prevents excitons generated in the light-emitting layer from migrating to the hole injection layer and has excellent thin film forming ability. As the above-mentioned electron injection layer material, specifically, there are fluorenone, anthraquinone dimethane, biphenylquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluoreneylidene methane, anthrone, etc. and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, etc., but are not limited thereto.

[0339] As the above-mentioned metal coordination compounds, there are lithium 8-hydroxyquinolate, zinc bis(8-hydroxyquinolate), copper bis(8-hydroxyquinolate), manganese bis(8-hydroxyquinolate), aluminum tris(8-hydroxyquinolate), aluminum tris(2-methyl-8-hydroxyquinolate), gallium tris(8-hydroxyquinolate), beryllium bis(10-hydroxybenzo[h]quinolate), zinc bis(10-hydroxybenzo[h]quinolate), gallium bis(2-methyl-8-quinolate) chloride, gallium bis(2-methyl-8-quinolate)(o-cresol), aluminum bis(2-methyl-8-quinolate)(1-naphthol), gallium bis(2-methyl-8-quinolate)(2-naphthol), etc., but are not limited thereto.

[0340] According to an embodiment of the present specification, the above-mentioned electron injection and transport layer is a layer that transports electrons to the light-emitting layer. When the above-mentioned organic light-emitting device includes an electron injection and transport layer other than the electron injection and transport layer containing the compound of the above chemical formula 1, the materials exemplified in the above electron transport layer and electron injection layer can be used, but are not limited thereto.

[0341] According to an embodiment of the present specification, the above-mentioned electron injection and transport layer contains a compound represented by the following chemical formula ET-1, but is not limited thereto.

[0342] [Chemical formula ET-1]

[0343]

[0344] In the above chemical formula ET-1,

[0345] At least one of Z11 to Z13 is N, and the rest are CH,

[0346] At least one of Z21 to Z23 is N, and the rest are CH,

[0347] L601 and L602 are the same as or different from each other, and each independently is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0348] Ar601 to Ar604 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0349] According to an embodiment of the present specification, the above L601 and L602 are the same as or different from each other, and each independently is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0350] According to an embodiment of the present specification, the above L601 and L602 are phenylene groups.

[0351] According to an embodiment of the present specification, the above Ar601 to Ar604 are the same as or different from each other, and each independently is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0352] According to an embodiment of the present specification, the above Ar601 to Ar604 are phenyl groups.

[0353] According to an embodiment of the present specification, the above chemical formula ET-1 is represented by the following compound.

[0354]

[0355] According to an embodiment of the present specification, the above electron injection and transport layer may further contain a metal coordination compound. The above metal coordination compound is as described above.

[0356] The above-mentioned electron blocking layer is a layer that prevents electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer, thereby improving the lifespan and efficiency of the device. When the above-mentioned electron blocking layer includes an additional electron blocking layer other than the electron blocking layer containing the compound of Chemical Formula 1 according to an embodiment of the present specification, well-known materials can be used without limitation, and the substances exemplified in the description of the above-mentioned hole injection layer can be used, but are not limited thereto. The above-mentioned electron blocking layer can be formed between the light-emitting layer and the hole transport layer, between the light-emitting layer and the hole injection layer, or between the light-emitting layer and the layer that simultaneously performs hole injection and hole transport.

[0357] The above-mentioned hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, there are diazole derivatives or triazole derivatives, phenanthroline derivatives, aluminum complexes, etc., but are not limited thereto.

[0358] According to an embodiment of the present specification, the above-mentioned hole blocking layer contains a compound represented by the following Chemical Formula HB-1, but is not limited thereto.

[0359] [Chemical Formula HB-1]

[0360]

[0361] In the above HB-1,

[0362] L701 is a directly bonded, substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0363] T1 to T3 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.

[0364] According to an embodiment of the present specification, the above Q1 to Q3 are N.

[0365] According to an embodiment of the present specification, the above L701 is a directly bonded, or substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0366] According to an embodiment of the present specification, the above L701 is a directly bonded or arylene group.

[0367] According to an embodiment of the present specification, the above L701 is a directly bonded, or arylene group having 6 to 30 carbon atoms.

[0368] According to an embodiment of the present specification, the above L701 is a directly bonded or phenylene group.

[0369] According to an embodiment of the present specification, T1 to T3 are the same as or different from each other, and each independently is a substituted or unsubstituted heteroaryl group.

[0370] According to an embodiment of the present specification, T1 to T3 are the same as or different from each other, and each independently is a monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted.

[0371] According to an embodiment of the present specification, T1 to T3 are the same as or different from each other, and each independently is a heteroaryl group.

[0372] According to an embodiment of the present specification, T1 to T3 are the same as or different from each other, and each independently is a monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms.

[0373] According to an embodiment of the present specification, T1 to T3 are carbazolyl groups.

[0374] According to an embodiment of the present specification, the above chemical formula HB-1 may include the following compounds, but is not limited thereto.

[0375]

[0376] According to an embodiment of the present specification, the above chemical formula HB-1 may also be used as the second host material of the light-emitting layer.

[0377] According to the materials used, the organic light-emitting device according to the present specification may be a top-emitting type, a bottom-emitting type, or a double-sided emitting type.

[0378] The organic light-emitting device according to the present specification may be included in various electronic devices and used. For example, the above electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0379] Hereinafter, in order to specifically illustrate the present specification, examples, comparative examples, etc. will be given and described in detail. However, the examples and comparative examples according to the present specification can be deformed into various different forms, and are not construed as limiting the scope of the present specification to the examples and comparative examples detailed below. The examples and comparative examples of the present specification are provided to more completely illustrate the present specification to those skilled in the art.

[0380] <Production Example 1: Synthesis of Compound 1>

[0381]

[0382] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, the compound 3-bromo-1,1'-biphenyl-2,2',3',4,4',5,5',6,6'-d9 (4.50 g, 18.60 mmol) and compound a-1 (8.73 g, 20.45 mmol) were completely dissolved in 240 mL of xylene. Then, NaOtBu (2.68 g, 27.89 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.29 g, 0.56 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and after filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized from 240 mL of ethyl acetate to produce compound 1 (6.66 g, 61%).

[0383] MS[M+H] + = 589

[0384] <Production Example 2: Synthesis of Compound 2>

[0385]

[0386] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, the compound 3-bromo-1,1'-biphenyl-2,2',3',4,4',5,5',6,6'-d9 (3.50 g, 18.60 mmol) and compound a-2 (8.73 g, 20.45 mmol) were completely dissolved in 250 mL of xylene. Then, NaOtBu (2.68 g, 27.89 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.29 g, 0.56 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and after filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized from 240 mL of ethyl acetate to produce compound 2 (7.03 g, 64%).

[0387] MS[M+H] + = 561

[0388] <Production Example 3: Synthesis of Compound 3>

[0389]

[0390] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, the compound 3-bromo-1,1':3',1”-terphenyl (4.50 g, 14.56 mmol) and compound a-3 (6.76 g, 16.02 mmol) were completely dissolved in 250 mL of xylene. Then, NaOtBu (2.10 g, 21.84 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.12 g, 0.23 mmol), the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, and after filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized from 290 mL of ethyl acetate to produce compound 3 (5.24 g, 55%).

[0391] MS[M+H] + = 651

[0392] <Production Example 4: Synthesis of Compound 4>

[0393]

[0394] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, the compound 3-bromo-1,1':3',1”-terphenyl (4.50 g, 14.56 mmol) and compound a-4 (6.76 g, 16.02 mmol) were completely dissolved in 240 mL of xylene. Then, NaOtBu (2.10 g, 21.84 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.22 g, 0.44 mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, and after filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized from 270 mL of ethyl acetate to produce compound 4 (5.01 g, 53%).

[0395] MS[M+H] + = 651

[0396] <Production Example 5: Synthesis of Compound 5>

[0397]

[0398] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, the compound 1-bromobenzene-2,3,4,5,6-d5 (3.50 g, 21.60 mmol) and compound a-1 (10.16 g, 23.77 mmol) were completely dissolved in 270 mL of xylene. Then, NaOtBu (3.11 g, 32.41 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.33 g, 0.65 mmol), the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, and after filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized from 270 mL of ethyl acetate to produce compound 5 (7.81 g, 71%).

[0399] MS[M+H] + = 509

[0400] <Production Example 6: Synthesis of Compound 6>

[0401]

[0402] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, the compound 1-bromobenzene-2,3,4,5,6-d5 (3.50 g, 21.60 mmol) and compound a-2 (10.16 g, 23.77 mmol) were completely dissolved in 260 mL of xylene. Then, NaOtBu (3.11 g, 32.41 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.33 g, 0.65 mmol), the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, and after filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized from 240 mL of ethyl acetate to produce compound 6 (7.55 g, 69%).

[0403] MS[M+H] + = 509

[0404] <Production Example 7: Synthesis of Compound 7>

[0405]

[0406] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, the compound 4-bromo-1,1'-biphenyl (3.50 g, 15.02 mmol) and compound a-5 (6.98 g, 16.52 mmol) were completely dissolved in 260 mL of xylene. Then, NaOtBu (2.17 g, 22.53 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.23 g, 0.45 mmol), the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, and after filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized from 280 mL of ethyl acetate to produce compound 7 (5.66 g, 67%).

[0407] MS[M+H] + = 575

[0408] <Production Example 8: Synthesis of Compound 8>

[0409]

[0410] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, the compound 5'-bromo-1,1':3',1”-terphenyl (3.50 g, 22.29 mmol) and compound a-6 (11.34 g, 23.41 mmol) were completely dissolved in 290 mL of xylene. Then, NaOtBu (3.21 g, 33.44 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.23 g, 0.45 mmol), the mixture was heated and stirred for 7 hours. The temperature was lowered to room temperature, and after filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized from 280 mL of ethyl acetate to produce compound 8 (7.89 g, 63%).

[0411] MS[M+H] + = 651

[0412] <Production Example 9: Synthesis of Compound 9>

[0413]

[0414] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 1-bromobenzene-2,3,4,5,6-d5 (3.50 g, 21.60 mmol) and compound a-7 (12.05 g, 23.77 mmol) were completely dissolved in 250 mL of xylene. Then, NaOtBu (3.11 g, 32.41 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.33 g, 0.65 mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, and the base was removed by filtration. Then, the xylene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to produce compound 9 (7.11 g, 56%).

[0415] MS[M+H] + = 589

[0416] <Production Example 10: Synthesis of Compound 10>

[0417]

[0418] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 (3.50 g, 14.46 mmol) and compound a-8 (8.07 g, 15.91 mmol) were completely dissolved in 260 mL of xylene. Then, NaOtBu (2.08 g, 21.69 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.22 g, 0.43 mmol), the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, and the base was removed by filtration. Then, the xylene was concentrated under reduced pressure and recrystallized from 270 mL of ethyl acetate to produce compound 10 (4.31 g, 57%).

[0419] MS[M+H] + = 669

[0420] <Example 1-1>

[0421] ITO (indium tin oxide) was used with The glass substrate with a thickness coated as a thin film is placed in distilled water dissolved with a detergent and washed using ultrasonic waves. At this time, the detergent used is a product of Fischer Co., and the distilled water used is the distilled water filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing is performed for 10 minutes by repeating with distilled water twice. After the distilled water washing is completed, ultrasonic washing is performed using a solvent of isopropyl alcohol, acetone, and methanol and then dried, and it is transported to a plasma cleaner. In addition, using oxygen plasma, the above substrate is cleaned for 5 minutes, and then the substrate is transported to a vacuum evaporator.

[0422] On the ITO transparent electrode prepared as the anode in this way, the following compound HT1 and the following compound HI1 are thermally vacuum-evaporated in a ratio of 98:2 (molar ratio) to form a hole injection layer. On the above hole injection layer, the following compound HT1 is vacuum-evaporated to form a hole transport layer. Then, on the above hole transport layer, BH (p-type) represented by compound 1 synthesized in the above Production Example 1 is vacuum-evaporated with a film thickness to form an electron blocking layer. Then, on the above electron blocking layer, a mixture of the following compound BH (n-type) and BH (p-type) represented by compound 1 synthesized in the above Production Example 1 mixed in a weight ratio of 1:1 and the following compound BD are vacuum-evaporated in a weight ratio of 88:12, so as to form a light-emitting layer with a thickness. On the above light-emitting layer, the following compound BH (n-type) is vacuum-evaporated with a film thickness to form a hole blocking layer. Then, on the above hole blocking layer, the following compound ET1 and the following compound LiQ are vacuum-evaporated in a weight ratio of 1:1, so as to form an electron injection and transport layer with a thickness. On the above electron injection and transport layer, lithium fluoride (LiF) is successively evaporated with a thickness, and aluminum is evaporated with a thickness to form a cathode.

[0423]

[0424] In the above process, the evaporation rate of the organic matter is maintained The evaporation rate of lithium fluoride for the cathode is maintained The evaporation rate of aluminum is maintained During evaporation, the vacuum degree is maintained at 2×10 -7 ~5×10 -6 Torr, thereby fabricating an organic light-emitting device.

[0425] <Examples 1-2 to 1-10>

[0426] Organic light-emitting devices were fabricated in the same manner as in Example 1-1, except that the compounds prepared in Preparation Examples 2 to 10 above were used in place of Compound 1 above.

[0427] <Comparative Examples 1-1 to 1-5>

[0428] Organic light-emitting devices were fabricated in the same manner as in Example 1-1, except that the compounds listed in Table 1 below were used in place of Compound 1 above. The compounds C1 to C5 used in Table 1 below are shown below.

[0429]

[0430] <Experimental Example>

[0431] When a current was applied to the organic light-emitting devices fabricated in the above Examples and Comparative Examples, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T 90 Refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 90%.

[0432]

Table 1

[0433]

[0434] As shown in Table 1 above, compounds of Chemical Formula 1 of this specification in which a monocyclic aryl group and L-Ar1 are bonded to a specific position of dicationic carbazole and the deuterium substitution rate of the dicationic carbazole compound is 50% or more are used as the p-type host of the hole transport region (electron blocking layer) and the light-emitting layer. That is, Examples 1-1 to 1-10 of the organic light-emitting device exhibit excellent characteristics in terms of the efficiency, driving voltage, and stability of the organic light-emitting device.

[0435] Specifically, it can be seen that compared with Comparative Examples 1-2 and 1-3 using compounds without deuterium substitution, and Comparative Examples 1-1, 1-4, and 1-5 using compounds with a deuterium substitution rate of less than 50% of dicationic carbazole, the organic light-emitting devices of Examples 1-1 to 1-10 of this specification are excellent in terms of efficiency, driving voltage, and lifetime (stability) due to the following structural features.

[0436] The above Chemical Formula 1 contains a dicarbazole structure, which increases the LUMO energy level of the compound, thereby preventing the host-guest electrostatic coupling state of the organic layer of the organic light-emitting device containing the same. In addition, the aryl group of the monocyclic ring and L-Ar1 bonded to a specific position of the dicarbazole participate in the conjugated system through the hyperconjugation effect, thereby having a structural feature of stabilizing the excited state and the polarized state of the above Chemical Formula 1. Therefore, the above Chemical Formula 1 is included in the organic layer of the organic light-emitting device, thereby enabling an improvement in efficiency, a lower driving voltage, and an improvement in lifetime characteristics.

[0437] In addition, the deuterium substitution rate of is 50% or more. Therefore, the energy of the ground state is reduced, and the bond length between deuterium and carbon becomes shorter. As a result, the molecular nuclear volume is reduced, whereby the electric susceptibility can be reduced and the intermolecular interaction can be weakened, thereby increasing the film volume. In addition, such characteristics can produce an effect of reducing the crystallinity of the film, that is, an amorphous state, and generally can effectively improve the lifetime and driving characteristics of the organic light-emitting device.

[0438] The preferred embodiments of the present invention (light-emitting layer BH (p-type), hole transport region (electron blocking layer)) have been described through the above content, but the present invention is not limited thereto. It can be implemented in various ways within the scope of the claims of the present invention and the detailed description of the invention, and this also belongs to the scope of the present invention.

Claims

1. A compound of the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, L is a direct bond, a phenylene group which may be substituted by deuterium, a biphenylene group which may be substituted by deuterium, or a divalent terphenyl group which may be substituted by deuterium, Ar1 is a phenyl group which may be substituted by deuterium or not, a biphenyl group which may be substituted by deuterium or not, or a terphenyl group which may be substituted by deuterium or not, m is an integer from 0 to 3, m' is an integer from 1 to 3, n is an integer from 0 to 3, n' is an integer from 1 to 3, m" is an integer from 0 to 3, n" is an integer from 0 to 3, m"+n" is an integer from 1 to 3, When m" and n" are each 2 or more, the structures in the two or more brackets are the same or different, D is deuterium, x1 to x6 are each an integer from 0 to 4, x'5 and x'6 are each an integer from 0 to 5, The chemical formula 1 The deuterium substitution rate is more than 50%. * is the site that binds to the L.

2. The compound according to claim 1, wherein The chemical formula 1 is the following chemical formula 1-1: [Chemical formula 1-1] In the chemical formula 1-1, The definitions of Ar1, D, m, m', m", n, n', n", x'5, x'6 and x1 to x6 are the same as those in Chemical Formula 1.

3. The compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 1-2 to 1-5: [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] [Chemical formula 1-5] In the chemical formulas 1-2 to 1-5, Definitions of L, Ar1, D, m, m', m", n, n', n", x'5, x'6 and x1 to x6 are the same as those in Chemical Formula 1.

4. The compound according to claim 1, wherein The above L is a deuterium-substituted or unsubstituted phenylene group, a deuterium-substituted or unsubstituted biphenylene group, or a deuterium-substituted or unsubstituted divalent terphenyl group, The Ar1 is a phenyl group which may be substituted by deuterium or not, a biphenyl group which may be substituted by deuterium or not, or a terphenyl group which may be substituted by deuterium or not.

5. The compound according to claim 1, wherein The L is a direct bond, The Ar1 is a phenyl group which may be substituted by deuterium or not, a biphenyl group which may be substituted by deuterium or not, or a terphenyl group which may be substituted by deuterium or not.

6. The compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 1-4-1 to 1-4-11: [Chemical formula 1-4-1] [Chemical formula 1-4-2] [Chemical formula 1-4-3] [Chemical formula 1-4-4] [Chemical formula 1-4-5] [Chemical formula 1-4-6] [Chemical formula 1-4-7] [Chemical formula 1-4-8] [Chemical formula 1-4-9] [Chemical formula 1-4-10] [Chemical formula 1-4-11] In the chemical formulas 1-4-1 to 1-4-11, Definitions of L, Ar1, D, x1 to x4, x'5 and x'6 are the same as those in Chemical Formula 1.

7. The compound according to claim 1, wherein The chemical formula 1 The deuterium substitution rate ranges from 50% to 93.33%.

8. The compound according to claim 1, wherein The deuterium substitution rate of the Chemical Formula 1 is 50% to 100%.

9. The compound according to claim 1, wherein The chemical formula 1 is any one of the following compounds:

10. An organic light-emitting device, wherein: include: A first electrode, a second electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 9.

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

12. The organic light emitting device according to claim 10, wherein: The organic layer includes a light-emitting layer, and the light-emitting layer contains the compound as a host of the light-emitting layer.

13. The organic light emitting device according to claim 11, wherein: The light emitting layer includes a dopant, and the dopant includes a phosphorescent dopant.

14. The organic light emitting device according to claim 11, wherein: The light-emitting layer is a blue light-emitting layer.

15. The organic light emitting device according to claim 10, wherein: The organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer contains the compound.

16. The organic light emitting device according to claim 10, wherein: The organic layer includes an electron blocking layer, and the electron blocking layer includes the compound.

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