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.

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2023-0019467 filed with the Korean Patent Office on February 14, 2023, the entire contents of which are incorporated into this specification.

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

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

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

[0005] Technical issues

[0006] The present specification provides a compound and an organic light-emitting device including the same.

[0007] Solution to the problem

[0008] One embodiment of the present specification provides a compound of the following Chemical Formula 1.

[0009] [Chemical formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] D is deuterium,

[0013] n is an integer greater than or equal to 1,

[0014] L1 is a directly bonded, or deuterium-substituted or unsubstituted arylene group,

[0015] HAr is a substituted or unsubstituted heteroaryl group.

[0016] In addition, one embodiment of the present specification provides an organic light-emitting device, including: a first electrode, a second electrode, a light-emitting layer arranged between the first electrode and the second electrode, and a first organic layer arranged between the light-emitting layer and the second electrode, wherein the first organic layer contains the above-mentioned compound.

[0017] Effects of the Invention

[0018] The compound described in this 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 this specification can achieve improved efficiency, lower driving voltage, and / or improved lifespan characteristics in an organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] Figure 1 and 2 An example of an organic light-emitting device according to an embodiment of the present specification is illustrated.

[0020] Figure 3 This is the MS chart of compound A.

[0021] [Explanation of symbols]

[0022] 1: Substrate

[0023] 2: First electrode

[0024] 3: Second electrode

[0025] 4: Luminous layer

[0026] 5: First organic layer

[0027] 6: Hole injection layer

[0028] 7: Hole transport layer

[0029] 8: Electron injection and transport layer DETAILED DESCRIPTION

[0030] Next, this specification is described in more detail.

[0031] This specification provides the compound of the above Chemical Formula 1.

[0032] According to one embodiment of the present specification, the chemical formula 1 is included in the organic layer of the organic light-emitting device to achieve improved efficiency, lower driving voltage, improved life characteristics, etc. Specifically, the fluoranthene structure as the core structure of the above chemical formula 1 is a structure that maintains a plane, and the film quality of the thin film becomes harder during evaporation, and the electron mobility increases, which has the effect of improving the device voltage, efficiency, and life.

[0033] In addition, the above chemical formula 1 contains deuterium. When deuterium is contained, the following effects are achieved. Specifically, the physical and chemical properties such as the bond length of the chemical bond related to deuterium are different from those of hydrogen. Compared with the CH bond, the stretching amplitude of the CD bond is smaller, so the van der Waals radius of deuterium is smaller than that of hydrogen. Generally, it can be shown that the CD bond is shorter and stronger than the CH bond. Therefore, when the hydrogen at the substitutable position of the above chemical formula 1 is replaced by deuterium, the energy of the ground state is reduced, and the bond length between deuterium and carbon becomes shorter, so the molecular hardcore volume is reduced, so the electrical polarizability can be reduced, and the intermolecular interaction is weakened, thereby increasing the film volume. In addition, such characteristics can produce the effect of reducing the crystallinity of the film, that is, the amorphous state, which can usually effectively improve the life 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.

[0034] In addition, the above Chemical Formula 1 has an electron depletion structure by including HAr as a substituent, thereby improving the polarity (dipole moment) of the molecule. Therefore, the above Chemical Formula 1 is included in the organic layer of the organic light-emitting device to achieve improved efficiency, lower driving voltage and improved life characteristics.

[0035] Throughout the present specification, the term "a combination thereof" included in the expression of Markush form refers to a mixture or combination of one or more components selected from the expression of Markush form, and means that one or more components selected from the above components are included.

[0036] In the present specification, examples of substituents are described below, but are not limited thereto.

[0037] In this manual, Indicates the connected part.

[0038] The term "substituted" mentioned above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The substituted position 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 be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.

[0039] In the present specification, the term "substituted or unsubstituted" means substituted with 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 amine group, an aryl group, a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and a heteroaryl group, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0040] In this specification, two or more substituents are linked to each other, which means that the hydrogen of any substituent is linked to another substituent. For example, two substituents can be linked to each other to form a phenyl group and a naphthyl group. In addition, the three substituents connected include not only (substituent 1)-(substituent 2)-(substituent 3) connected continuously, but also (substituent 2) and (substituent 3) connected to (substituent 1). For example, phenyl, naphthyl and isopropyl can be connected to form The above definition also applies to 4 or more substituents connected together.

[0041] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0042] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0043] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, and specifically includes 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 and the like, but is not limited thereto.

[0044] In this specification, the alkoxy group may be straight chain, branched chain or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably the number of carbon atoms is 1 to 30. Specifically, it may be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentyl group, a n-hexyl group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

[0045] In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0046] In the present specification, the above-mentioned halogenated alkyl group refers to an alkyl group in the definition of the above-mentioned alkyl group substituted with at least one halogen group.

[0047] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0048] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 6 to 30. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

[0049] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 10 to 30. Specifically, the polycyclic aryl group may be naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, phenanthrenyl, perylene, yl, fluorenyl, etc., but are not limited to these.

[0050] In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0051] In the case where the above fluorenyl group is substituted,

[0052] etc., but not limited thereto.

[0053] In this specification, "adjacent" groups may refer to substituents substituted on atoms directly connected to the atom substituted by the substituent, substituents closest to the substituent in stereostructure, or other substituents 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 can be interpreted as "adjacent" groups to each other.

[0054] In the present specification, the heteroaryl group contains one or more non-carbon atoms, i.e., heteroatoms. Specifically, the 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 the number of carbon atoms is 2 to 30. The heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthridine, phenanthroline, isothiophene Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothioyl, phenanthroline Thiazole (phenoxathiine), phen Examples of the present invention include, but are not limited to, phenoxazine, phenothiazine, indenocarbazolyl, spirofluorenylxanthenyl and spirofluorenylthioxanthenyl.

[0055] In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, etc. The alkyl group in the alkylsilyl group may be the same as the examples given above for the alkyl group, the aryl group in the arylsilyl group may be the same as the examples given above for the aryl group, and the heteroaryl group in the heteroarylsilyl group may be the same as the examples given above for the heteroaryl group.

[0056] In this specification, the boron group can be -BR 100 R 101 , the above R 100 and R 101The same or different, each independently can be selected from hydrogen, deuterium, halogen, nitrile, substituted or unsubstituted monocyclic or polycyclic cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted linear or branched 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. The above-mentioned boryl group specifically includes dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, etc., but is not limited thereto.

[0057] In the present specification, the amino group can be selected from -NH2, alkylamino, N-alkylarylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino and heteroarylamino, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amino group include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthracenylamino, 9-methyl-anthrylamino, diphenylamino, ditolylamino, N-phenyltolylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrenylfluorenylamino, N-biphenylfluorenylamino, etc., but are not limited thereto.

[0058] In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted on the N of the amine group. The alkyl group and the aryl group in the above-mentioned N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.

[0059] In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group or a heteroaryl group is substituted on the N of the amine group. The aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and the heteroaryl group described above.

[0060] In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted on the N of the amine group. The alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the alkyl group and the heteroaryl group described above.

[0061] In this specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups or substituted or unsubstituted diarylamine groups. The arylamine groups containing two or more of the above aryl groups may contain monocyclic aryl groups, polycyclic aryl groups, or may contain both monocyclic aryl groups and polycyclic aryl groups. For example, the aryl groups in the above arylamine groups may be selected from the examples of the above aryl groups.

[0062] In this specification, examples of heteroarylamine groups include substituted or unsubstituted monoheteroarylamine groups, or substituted or unsubstituted diheteroarylamine groups. The heteroarylamine groups containing two or more of the above heteroaryl groups may contain monocyclic heteroaryl groups, polycyclic heteroaryl groups, or may contain both monocyclic heteroaryl groups and polycyclic heteroaryl groups. For example, the heteroaryl groups in the above heteroarylamine groups may be selected from the examples of the above heteroaryl groups.

[0063] 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, and the above-mentioned aromatic hydrocarbon ring group may be applied to the above-mentioned description of the aryl group, and the aliphatic hydrocarbon ring group may be applied to the above-mentioned description of the cycloalkyl group. In addition, the condensed ring group of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring may be applied to the structure in which the above-mentioned aryl group and the cycloalkyl group are condensed with each other.

[0064] In the present specification, an arylene group refers to a group having two bonding positions on an aryl group, that is, a divalent group. The above description of the aryl group is applicable to these groups except that they are each a divalent group.

[0065] In the present specification, a heteroarylene group refers to a group having two bonding positions on a heteroaryl group, that is, a divalent group. The above description of the heteroaryl group is applicable to these groups except that they are each a divalent group.

[0066] In one embodiment of the present specification, the part without a substituent in the above Chemical Formula 1 may be substituted with hydrogen or deuterium.

[0067] In the present specification, the phrase "adjacent groups are bonded to form a ring" in a substituent means that adjacent groups are bonded to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0068] In the present specification, in a substituted or unsubstituted ring formed by bonding to each other, "ring" means a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0069] In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon. The hydrocarbon ring may be selected from the examples of the cycloalkyl group or aryl group except that the hydrocarbon ring is not monovalent.

[0070] In the present specification, the heterocycle contains one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may contain one or more atoms selected from O, N, Se, S, etc. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic. The aromatic heterocycle may be selected from the examples of the heteroaryl group except that it is not monovalent.

[0071] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dihydrofuran, Examples of the present invention include, but are not limited to, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azacyclooctane, and thiocane.

[0072] Unless otherwise defined in this specification, all technical terms and scientific terms used in this specification have the same meaning as those generally understood by those skilled in the art. Methods and materials similar to or equivalent to the description in this specification can be used for the implementation or test of embodiments of the present invention, but suitable methods and materials are described later. All publications, patent applications, patents and other references mentioned in this specification are included in this specification as a whole as a reference, and in the case of conflict, if no specific passage is mentioned, the present specification including the definition takes precedence. In addition, materials, methods and embodiments are only illustrative and not intended to be limited.

[0073] Next, the compound of the above Chemical Formula 1 will be described in detail.

[0074] According to one embodiment of the present specification, the dipole moment value of the chemical formula 1 is 1 debye or more, specifically 1 to 10 debye, and more specifically 1.00 to 7.50 debye.

[0075] When the dipole moment of the chemical formula 1 is 1 debye or more, the molecular arrangement is better formed due to the influence of the dipole moment, and the film quality becomes harder, thereby having the effect of improving the life of the organic light-emitting device containing it. The film quality improved by the molecular arrangement adjusts the electron migration speed transmitted from the organic layer containing the compound to the light-emitting layer, thereby also having the effect of secondary improvement of life.

[0076] The dipole moment according to one embodiment of the present specification can be calculated by a method used in the technical field. Specifically, the dipole moment is a physical quantity indicating the degree of polarity and can be calculated by the following mathematical formula 1.

[0077] [Mathematical formula 1]

[0078]

[0079] ρ(r0): molecular density

[0080] V: volume

[0081] r: the point of observation

[0082] d 3 r0: per unit volume (an elementary volume)

[0083] In the above mathematical formula 1, the molecular density is calculated to obtain the value of the dipole moment. For example, the charge (Charge) and dipole (Dipole) of each atom can be obtained using the Hirshfeld Charge Analysis method, and the molecular density can be obtained by calculation according to the following formula, and the calculation result is substituted into the above mathematical formula 1 to obtain the dipole moment.

[0084] -Weight Function

[0085]

[0086] ·ρ α (r α ): spherically averaged ground-state amomic density

[0087] · Promolecule density

[0088] -Deformation Density

[0089] ·

[0090] ρ(r): molecular density

[0091] ·ρ α (r α ): located at coordinate R α The density of the free atom α located at coordinates R α )

[0092] -Atomic Charge

[0093] q(α)=-∫ρ d (r)W α (r)d 3 r

[0094] ·W α (r): weight function

[0095] According to one embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 2 to 4.

[0096] [Chemical formula 2]

[0097]

[0098] [Chemical formula 3]

[0099]

[0100] [Chemical formula 4]

[0101]

[0102] In the above chemical formulas 2 to 4,

[0103] The definitions of D, n, L1 and HAr are the same as those in the above Chemical Formula 1.

[0104] According to one embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-3.

[0105] [Chemical formula 1-1]

[0106]

[0107] [Chemical formula 1-2]

[0108]

[0109] [Chemical formula 1-3]

[0110]

[0111] In the above chemical formulas 1-1 to 1-3,

[0112] The definitions of D, n and L1 are the same as those in the above chemical formula 1,

[0113] At least one of Y1 to Y5 is N, and the rest of Y1 to Y5 that are not N are the same as or different from each other and are independently CR1,

[0114] X1 is O, S, CR5R6 or NR7,

[0115] Y6 is CR8 or N,

[0116] Y7 is CR9 or N,

[0117] R1 to R9 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or any one or more adjacent groups are combined to form a substituted or unsubstituted ring.

[0118] According to one embodiment of the present specification, the HAr is any one of the following structures.

[0119]

[0120]

[0121] In the above structure,

[0122] R2 to R9 and R11 to R15 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or any one or more adjacent groups are combined to form a substituted or unsubstituted ring.

[0123] According to one embodiment of the present specification, L1 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, which is directly bonded or substituted or unsubstituted with deuterium.

[0124] According to one embodiment of the present specification, L1 is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms, which is directly bonded or substituted or unsubstituted with deuterium.

[0125] According to one embodiment of the present specification, L1 is a monocyclic or polycyclic arylene group having 6 to 10 carbon atoms, which is directly bonded or substituted or unsubstituted with deuterium.

[0126] According to one embodiment of the present specification, L1 is a monocyclic arylene group having 6 to 10 carbon atoms, which is directly bonded or substituted or unsubstituted with deuterium.

[0127] According to one embodiment of the present specification, the above-mentioned L1 is a direct bond, or a phenylene group which may be substituted with deuterium or not.

[0128] According to one embodiment of the present specification, the above-mentioned L1 is a direct bond, a phenylene group, or a phenylene group substituted with deuterium.

[0129] According to one embodiment of the present specification, the HAr is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0130] According to one embodiment of the present specification, the HAr is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing N and having 2 to 30 carbon atoms.

[0131] According to one embodiment of the present specification, the HAr is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing one or more of N, O and S and having 2 to 30 carbon atoms.

[0132] According to one embodiment of the present specification, the HAr is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

[0133] According to one embodiment of the present specification, the HAr is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing N and having 2 to 20 carbon atoms.

[0134] According to one embodiment of the present specification, the HAr is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing one or more of N, O and S and having 2 to 20 carbon atoms.

[0135] According to one embodiment of the present specification, the HAr is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms that is substituted or unsubstituted with deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0136] According to one embodiment of the present specification, the HAr is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms containing N, which is unsubstituted or substituted with deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0137] According to one embodiment of the present specification, the HAr is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms and containing one or more of N, O and S, which is unsubstituted or substituted with deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0138] According to one embodiment of the present specification, the above-mentioned HAr is a benzimidazolyl group substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a triazine group substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a pyrimidinyl group substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a quinazolinyl group substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; a benzo[pi]midazolyl group substituted or unsubstituted by deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof oxazolyl; benzothiazolyl substituted or unsubstituted by deuterium; triazolyl substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; pyridazinyl substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; oxadiazolyl; phenanthroline substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; imidazolyl substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof; substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof or thiazolyl which may be substituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

[0139] According to one embodiment of the present specification, the above-mentioned HAr is a benzimidazolyl group which is substituted or unsubstituted by deuterium, a methyl group, an ethyl group, a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, or a combination thereof; a triazine group which is substituted or unsubstituted by deuterium, a methyl group, an ethyl group, a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, or a combination thereof; a pyrimidinyl group which is substituted or unsubstituted by deuterium, a methyl group, an ethyl group, a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, or a combination thereof; a quinazolinyl group which is substituted or unsubstituted by deuterium, a methyl group, an ethyl group, a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, or a combination thereof; a benzo[pi]midazolyl group which is substituted or unsubstituted by deuterium, a methyl group, an ethyl group, a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, or a combination thereof; oxazolyl; benzothiazolyl substituted or unsubstituted by deuterium; triazolyl substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; pyridazinyl substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; oxadiazolyl; phenanthroline substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; imidazolyl substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof; substituted or unsubstituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof or thiazolyl which may be substituted by deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0140] According to one embodiment of the present specification, the above-mentioned HAr is a benzimidazolyl group substituted or unsubstituted by deuterium, methyl, ethyl, phenyl, or a combination thereof; a triazine group substituted or unsubstituted by deuterium, methyl, ethyl, phenyl, or a combination thereof; a pyrimidinyl group substituted or unsubstituted by deuterium, methyl, ethyl, phenyl, or a combination thereof; a quinazolinyl group substituted or unsubstituted by deuterium, methyl, ethyl, phenyl, or a combination thereof; a benzo[pi]midazolyl group substituted or unsubstituted by deuterium, methyl, ethyl, phenyl, or a combination thereof; oxazolyl; benzothiazolyl substituted or unsubstituted by deuterium; triazolyl substituted or unsubstituted by deuterium, phenyl, or a combination thereof; pyridazinyl substituted or unsubstituted by deuterium, phenyl, or a combination thereof; oxadiazolyl; phenanthroline substituted or unsubstituted by deuterium, phenyl, or a combination thereof; imidazolyl substituted or unsubstituted by deuterium, phenyl, or a combination thereof; substituted or unsubstituted by deuterium, phenyl, or a combination thereof or thiazolyl which may be substituted by deuterium, phenyl, or a combination thereof.

[0141] According to one embodiment of the present specification, the above-mentioned R2 to R9 and R11 to R15 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or any one or more adjacent groups are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0142] According to one embodiment of the present specification, the above-mentioned R2 to R9 and R11 to R15 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, or any one or more adjacent pairs of groups are combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

[0143] According to one embodiment of the present specification, the above-mentioned R2 to R9 and R11 to R15 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, or any one or more adjacent pairs of groups are combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

[0144] According to one embodiment of the present specification, the above-mentioned R2 to R9 and R11 to R15 are the same as or different from each other, and are each independently hydrogen, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, which is substituted or not substituted by deuterium, or a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, which is substituted or not substituted by deuterium, or any one or more adjacent groups are combined with each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or not substituted by deuterium.

[0145] According to one embodiment of the present specification, the above-mentioned R2 to R9 and R11 to R15 are the same as or different from each other, and are each independently hydrogen, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, which is substituted or not substituted by deuterium, or a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, which is substituted or not substituted by deuterium, or any one or more adjacent pairs of groups are combined to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, which is substituted or not substituted by deuterium.

[0146] According to one embodiment of the present specification, the above-mentioned R2 to R9 and R11 to R15 are the same as or different from each other, and are each independently hydrogen, a methyl group substituted or unsubstituted by deuterium, an ethyl group substituted or unsubstituted by deuterium, or a phenyl group substituted or unsubstituted by deuterium, or any one or more adjacent groups are combined with each other to form a benzene group substituted or unsubstituted by deuterium.

[0147] According to one embodiment of the present specification, the chemical formula 1 is any one of the following compounds.

[0148]

[0149]

[0150]

[0151] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 0.02% or more.

[0152] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 0.1% or more.

[0153] According to one embodiment of the present specification, the deuterium substitution rate of the above chemical formula 1 is greater than 1%.

[0154] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 10% or more.

[0155] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 15% or more.

[0156] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 0.02% to 100%.

[0157] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 0.1% to 100%.

[0158] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 1% to 100%.

[0159] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 10% to 100%.

[0160] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 15% to 100%.

[0161] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 10% to 99%.

[0162] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 10% to 90%.

[0163] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 15% to 99%.

[0164] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 15% to 90%.

[0165] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 15% to 89%.

[0166] In the present specification, “containing deuterium”, “deuterated” or “deuterated” means that hydrogen at a substitutable position of the compound is substituted with deuterium.

[0167] In the present specification, “overdeuterated” refers to a compound or group in which all hydrogen in the molecule is replaced by deuterium, and has the same meaning as “100% deuterated”.

[0168] In the present specification, "X% deuterated", "deuteration degree X%", or "deuterium substitution rate X%" means that X% of the hydrogen atoms at substitutable positions in the structure are substituted with deuterium. For example, when the structure is dibenzofuran, "25% deuterated" the dibenzofuran, "deuteration degree 25%" of the dibenzofuran, or "deuterium substitution rate 25%" of the dibenzofuran means that 2 of the 8 hydrogen atoms at substitutable positions of the dibenzofuran are substituted with deuterium.

[0169] In this specification, the "degree of deuteration" or "deuterium substitution rate" can be determined by nuclear magnetic resonance spectroscopy ( 1The expression of the peptides can be confirmed by known methods such as HNMR (thin-layer chromatography / mass spectrometry), TLC / MS (thin-layer chromatography / mass spectrometry), or GC / MS (gas chromatography / mass spectrometry).

[0170] Specifically, by nuclear magnetic resonance spectroscopy ( 1 When analyzing the "deuteration degree" or "deuterium substitution rate" by H NMR, DMF (dimethylformamide) can be added as an internal standard. 1 The integration ratio in H NMR is used to calculate the deuteration degree or deuterium substitution rate from the integrated amount of the total peak.

[0171] In addition, when analyzing the "degree of deuteration" or "deuterium substitution rate" by TLC / MS (thin layer chromatography / mass spectrometry), the substitution rate can be calculated based on the maximum value (median value) of the distribution formed by the molecular weight at the end of the reaction. For example, when analyzing the degree of deuteration of the following compound A, the molecular weight of the following starting material is 506. When it is indicated that Figure 3 When the maximum molecular weight (median value) of the following compound A in the MS chart is 527, 21 of the 26 hydrogen atoms at the substitutable positions of the following starting material are substituted with deuterium, and therefore it can be calculated that about 81% of the hydrogen atoms are deuterated.

[0172]

[0173] In this specification, D represents deuterium.

[0174] In addition, the present specification provides an organic light-emitting device including the above-mentioned compound.

[0175] In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.

[0176] In the present specification, when a part is indicated to “include / comprise” a certain component, unless there is a particular description to the contrary, it means that other components may be further included, rather than excluding other components.

[0177] In this specification, the above-mentioned "layer" is interchangeable with the "film" mainly used in this technical field, and refers to a coating covering the 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 one embodiment, the size of the "layer" can be equal to the size of the entire device, can be equivalent to the size of a specific functional area, or can be as small as a single sub-pixel.

[0178] In this specification, the meaning of specific substance A contained in layer B includes i) the case where one or more substances A are contained in one layer B, and ii) the case where layer B is composed of one or more layers and substance A is contained in one or more layers of the multiple layers B.

[0179] In this specification, the meaning of a specific substance A being contained in layer C or layer D refers to all of the following situations: i) substance A is contained in one or more layers among one or more layers C, or ii) substance A is contained in one or more layers among one or more layers D, or iii) substance A is contained in one or more layers C and one or more layers D, respectively.

[0180] One embodiment of the present specification provides an organic light-emitting device, including: a first electrode, a second electrode, a light-emitting layer disposed between the first electrode and the second electrode, and a first organic layer disposed between the light-emitting layer and the second electrode, wherein the first organic layer contains the compound.

[0181] According to one embodiment of the present specification, the organic light-emitting device includes a second organic layer disposed between the first electrode and the light-emitting layer. The second organic layer is one or more layers.

[0182] The first organic layer and the second organic layer are collectively referred to as an organic layer. The organic layer of the organic light-emitting device may be formed by a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, it may 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 may include a smaller number of organic layers.

[0183] According to one embodiment of the present specification, the first organic layer is a hole blocking layer, an electron regulating layer, an electron injection layer, an electron transport layer, or any one of an electron injection and transport layer.

[0184] According to one embodiment of the present specification, the first organic layer is a hole blocking layer.

[0185] According to one embodiment of the present specification, the first organic layer is an electron adjustment layer.

[0186] According to one embodiment of the present specification, the first organic layer is an electron injection layer.

[0187] According to one embodiment of the present specification, the first organic layer is an electron transport layer.

[0188] According to one embodiment of the present specification, the first organic layer is an electron injection and transport layer.

[0189] According to one embodiment of the present specification, the first organic layer is a hole blocking layer, an electron regulating layer, an electron injection layer, an electron transport layer, or any one of an electron injection and transport layer.

[0190] According to one embodiment of the present specification, the first organic layer is any one of a hole blocking layer, an electron regulating layer, an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the hole blocking layer, electron regulating layer, electron injection layer, electron transport layer, or electron injection and transport layer contains the above-mentioned compound.

[0191] According to one embodiment of the present specification, the first organic layer is a hole blocking layer, and the hole blocking layer includes the compound.

[0192] According to one embodiment of the present specification, the first organic layer is an electron adjustment layer, and the electron adjustment layer includes the compound.

[0193] According to one embodiment of the present specification, the first organic layer is an electron injection layer, and the electron injection layer includes the compound.

[0194] According to one embodiment of the present specification, the first organic layer is an electron transport layer, and the electron transport layer includes the compound.

[0195] According to one embodiment of the present specification, the first organic layer is an electron injection and transport layer, and the electron injection and transport layer includes the compound.

[0196] According to one embodiment of the present specification, the dipole moment value of the compound is 1 debye or more, specifically 1 to 10 debye, and more specifically 1.00 to 7.50 debye.

[0197] When the dipole moment of the compound is 1 debye or more, the molecular arrangement occurs better due to the influence of the dipole moment, and the film becomes harder, thereby having the effect of improving the life of the organic light-emitting device containing it. The film quality improved by the molecular arrangement adjusts the electron migration speed transferred from the organic layer containing the compound to the light-emitting layer, thereby having the effect of secondary improvement of life.

[0198] According to one embodiment of the present specification, the second organic layer is one or more of an electron blocking layer, a hole injection layer, a hole transport layer, a hole injection and transport layer, and a hole regulation layer.

[0199] According to one embodiment of the present specification, the above-mentioned organic layer also includes one or more layers of 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.

[0200] According to one embodiment of the present specification, the above-mentioned organic light-emitting device also includes one 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.

[0201] According to one embodiment of the present specification, the organic light-emitting device includes: a first electrode; a second electrode arranged opposite to the first electrode; a light-emitting layer arranged between the first electrode and the second electrode; and two or more organic layers arranged between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0202] According to one embodiment of the present specification, the above-mentioned two or more organic layers can 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.

[0203] According to one 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 include the same or different substances.

[0204] According to one embodiment of the present specification, the first electrode is an anode or a cathode.

[0205] According to one embodiment of the present specification, the second electrode is a cathode or an anode.

[0206] According to one embodiment of the present specification, the organic light emitting device may be a normal type organic light emitting device having a structure in which an anode, a light emitting layer, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

[0207] According to 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, a light emitting layer, and an anode are sequentially stacked on a substrate.

[0208] According to 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 material layers, and a cathode are sequentially stacked on a substrate.

[0209] According to one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device of a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0210] For example, the structure of an organic light-emitting device according to one embodiment of the present specification is shown in Figure 1 and 2 . The above Figure 1 and 2 An organic light emitting device is exemplified, and is not limited thereto.

[0211] Figure 1 exemplifies the structure of an organic light-emitting device in which a first electrode 2, a light-emitting layer 4, a first organic layer 5, and a second electrode 3 are sequentially stacked on a substrate 1. The above-mentioned compound is contained in the first organic layer.

[0212] Figure 2 exemplifies the structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 6, a hole transport layer 7, a light-emitting layer 4, an electron injection and transport layer 8, and a second electrode 3 are sequentially stacked on a substrate 1. The above compound is contained in the electron injection and transport layer.

[0213] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the technical field, except that the first organic layer includes the compound, ie, the compound of the above Chemical Formula 1.

[0214] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

[0215] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, a light-emitting layer, a first organic layer, and a second electrode on a substrate. In this case, the device can be manufactured as follows: a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation is used to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode substance, an organic layer, and an anode substance on a substrate.

[0216] In addition, the compound of the above chemical formula 1 can be used not only by vacuum evaporation method but also by solution coating method to form an organic layer when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating method, dip coating method, blade coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited thereto.

[0217] In addition to these methods, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode material, an organic layer, and an anode material on a substrate. However, the manufacturing method is not limited to this.

[0218] As the above-mentioned anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. For example, there are metals such as vanadium, chromium, copper, zinc, gold, or their alloys; 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-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but are not limited thereto.

[0219] In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function, such as metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but not limited thereto.

[0220] The above-mentioned light-emitting layer may include a host material and a dopant material. When the organic light-emitting device according to one embodiment of the present specification includes another light-emitting layer in addition to the light-emitting layer including the above-mentioned chemical formula 1, the host material includes an aromatic condensed ring derivative or a heterocyclic compound. Specifically, as the aromatic condensed ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as the heterocyclic compound, there are dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0221] According to one embodiment of the present specification, the host includes a compound represented by the following chemical formula H-1, but is not limited thereto.

[0222] [Chemical formula H-1]

[0223]

[0224] In the above chemical formula H-1,

[0225] L20 and L21 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0226] Ar20 and Ar21 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0227] R201 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0228] r201 is an integer of 1 to 8. When r201 is 2 or more, two or more R201s are the same as or different from each other.

[0229] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are each independently 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.

[0230] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are each independently a direct bond, a deuterium-substituted or unsubstituted phenylene group, a deuterium-substituted or unsubstituted biphenylene group, a deuterium-substituted or unsubstituted naphthylene group, a divalent dibenzofuranyl group, or a divalent dibenzothiophenyl group.

[0231] In one embodiment of the present specification, Ar20 and Ar21 are the same or different and are each independently 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.

[0232] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently 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.

[0233] In one embodiment of the present specification, Ar20 and Ar21 are the same or different from each other and are independently phenyl substituted or unsubstituted by deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; terphenyl; biphenyl substituted or unsubstituted by deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; naphthyl substituted or unsubstituted by deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Thienyl substituted or unsubstituted by a monocyclic or polycyclic aryl group; phenanthryl; dibenzofuranyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; naphthobenzofuranyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; dibenzothienyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or naphthobenzothienyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0234] 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 by deuterium, a biphenyl group substituted or unsubstituted by deuterium, a terphenyl group, a naphthyl group substituted or unsubstituted by deuterium, a thienyl group substituted or unsubstituted by phenyl, a phenanthryl group, a dibenzofuranyl group, a naphthiobenzofuranyl group, a dibenzothiophenyl group, or a naphthiobenzothiophenyl group.

[0235] In one embodiment of the present specification, the Ar20 is a substituted or unsubstituted heterocyclic group, and the Ar21 is a substituted or unsubstituted aryl group.

[0236] According to one embodiment of the present specification, the above R201 is hydrogen.

[0237] According to one embodiment of the present specification, the chemical formula H-1 is represented by the following compounds, but is not limited thereto.

[0238]

[0239] As the dopant material, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamine. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as a metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0240] According to one embodiment of the present specification, the dopant includes a compound represented by the following Chemical Formula D-1, but is not limited thereto.

[0241] [Chemical formula D-1]

[0242]

[0243] In the above chemical formula D-1,

[0244] T1 to T6 are the same as or different from each other, and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkylsilyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0245] t5 and t6 are each an integer from 1 to 4,

[0246] When the above t5 is 2 or more, the above two or more T5 are the same or different from each other.

[0247] When the above t6 is 2 or more, the above two or more T6 may be the same as or different from each other.

[0248] According to one embodiment of the present specification, the above-mentioned T1 to T6 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0249] According to one embodiment of the present specification, the above-mentioned T1 to T6 are the same as or different from each other and are independently hydrogen; a straight-chain or branched alkyl group having 1 to 30 carbon atoms; a straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms which is unsubstituted or substituted with deuterium, cyano, or a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaromatic group having 2 to 30 carbon atoms.

[0250] According to one embodiment of the present specification, the above-mentioned T1 to T6 are the same as or different from each other, and are each independently hydrogen, isopropyl, tert-butyl, trimethylsilyl, unsubstituted phenyl, phenyl substituted by deuterium, phenyl substituted by cyano, phenyl substituted by methyl, or terphenyl substituted or unsubstituted by methyl and trimethylsilyl.

[0251] According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compounds, but is not limited thereto.

[0252]

[0253] The hole injection layer is a layer that receives holes from the electrode. The hole injection material is preferably a material that has the ability to transport holes, has the effect of receiving holes from the anode, and has an excellent hole injection effect on the light-emitting layer or the light-emitting material. In addition, it is preferably a material that has an excellent ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. Moreover, it is preferably a material with 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. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, and arylamine organics; hexanitrile hexaazatriphenylene organics; quinacridone organics; perylene organics; anthraquinone, polyaniline, and polythiophene conductive polymers, etc., but are not limited to these.

[0254] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-1, but is not limited thereto.

[0255] [Chemical formula HI-1]

[0256]

[0257] In the above chemical formula HI-1,

[0258] R301 to R306 are the same as or different from each other, and are independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amine, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0259] L301 and L302 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group.

[0260] According to one embodiment of the present specification, R301 and R302 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 30 carbon atoms.

[0261] According to one embodiment of the present specification, R301 and R302 are methyl groups.

[0262] According to one embodiment of the present specification, R301 and R302 are combined with each other to form a substituted or unsubstituted heterocyclic ring.

[0263] According to one embodiment of the present specification, R301 and R302 are bonded to each other to form a substituted or unsubstituted acridine ring.

[0264] According to one embodiment of the present specification, R301 and R302 are bonded to each other to form a dihydroacridine ring which may be substituted with a phenyl group.

[0265] According to one embodiment of the present specification, L301 and L302 are directly bonded.

[0266] According to one embodiment of the present specification, R303 to R306 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0267] According to one embodiment of the present specification, the above R303 to R306 are the same as or different from each other, and are each independently a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0268] According to one embodiment of the present specification, R303 to R306 are the same as or different from each other, and are each independently a phenyl group, or a carbazolyl group which may be substituted or unsubstituted with a phenyl group.

[0269] According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compounds, but is not limited thereto.

[0270]

[0271] The 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, preferably a material with a large mobility for holes. As specific examples, there are arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited thereto.

[0272] According to one embodiment of the present specification, the hole transport layer includes a compound represented by the following chemical formula HT-1, but is not limited thereto.

[0273] [Chemical formula HT-1]

[0274]

[0275] In the above chemical formula HT-1,

[0276] At least one of X'1 to X'6 is N, and the others are CH,

[0277] R309 to R314 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amine, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0278] According to one embodiment of the present specification, X'1 to X'6 are N.

[0279] According to one embodiment of the present specification, R309 to R314 are cyano groups.

[0280] According to one embodiment of the present specification, the chemical formula HT-1 is represented by the following compound.

[0281]

[0282] According to one embodiment of the present specification, the hole transport layer includes a compound represented by the following chemical formula HT-2, but is not limited thereto.

[0283] [Chemical formula HT-2]

[0284]

[0285] In the above chemical formula HT-2,

[0286] R315 to R317 are the same as or different from each other, and are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0287] r315 is an integer from 1 to 5. When the above r315 is 2 or more, the two or more R315 are the same or different from each other.

[0288] r316 is an integer of 1 to 5. When the number of r316 is 2 or more, two or more R316 are the same as or different from each other.

[0289] According to one embodiment of the present specification, the above R317 is any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0290] According to one embodiment of the present specification, the R317 is any one selected from a carbazolyl group, a phenyl group, a biphenyl group, and a combination thereof.

[0291] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are independently substituted or unsubstituted aryl groups, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0292] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are independently hydrogen or phenyl, or are combined with adjacent groups to form a spirofluorene indene substituted with a methyl group.

[0293] According to one embodiment of the present specification, the chemical formula HT-2 is represented by the following compound.

[0294]

[0295] The hole regulating layer is a layer that regulates the holes transferred from the hole transport layer to be smoothly injected into the light-emitting layer, and prevents the electrons injected from the electron injection layer from passing through the light-emitting layer into the hole injection layer, thereby improving the life and efficiency of the device. Known materials can be used without restriction, and can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and a layer that simultaneously performs hole injection and hole transport.

[0296] According to one embodiment of the present specification, the hole injection and transport layer is a layer that transports holes to the light-emitting layer. The hole transport layer and the hole injection layer may be made of the substances exemplified above, but are not limited thereto.

[0297] The electron regulating layer is a layer for regulating the smooth injection of electrons transferred from the electron transport layer into the light emitting layer. When another electron regulating layer is included in addition to the electron regulating layer including the compound of Chemical Formula 1, known materials may be used without limitation.

[0298] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. When the organic light-emitting device includes an electron transport layer other than the electron transport layer containing the compound of the above chemical formula 1, the electron transport substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, preferably a substance with a large mobility for electrons. As a specific example, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free 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, a suitable cathode material is a common substance having a low work function and accompanied by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, etc., in each case accompanied by an aluminum layer or a silver layer.

[0299] The thickness of the electron transport layer can be 1 to 50 nm. When the thickness of the electron transport layer is 1 nm or more, it has the advantage of preventing the electron transport characteristics from being reduced, and when the thickness is 50 nm or less, it has the advantage of preventing the driving voltage from increasing due to the increase in electron migration when the thickness of the electron transport layer is too thick.

[0300] The electron injection layer is a layer that receives electrons from the electrode. As the electron injection material, preferably, the following materials are used: materials that have excellent ability to transport electrons, have the effect of receiving electrons from the second electrode, and have excellent electron injection effect on the light-emitting layer or the light-emitting material. In addition, preferably, materials that prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer and have excellent thin film forming ability. When the above-mentioned organic light-emitting device includes an electron injection layer other than the electron injection layer containing the compound of the above-mentioned chemical formula 1, specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0301] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

[0302] According to one embodiment of the present specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. When the organic light-emitting device includes an electron injection and transport layer other than the electron injection and transport layer including the compound of Chemical Formula 1, the substances exemplified in the electron transport layer and the electron injection layer may be used, but are not limited thereto.

[0303] According to one embodiment of the present specification, the electron injection and transport layer may further include a metal coordination compound. The metal coordination compound is as described above.

[0304] The electron blocking layer is a layer that prevents the electrons injected from the electron injection layer from entering the hole injection layer through the light-emitting layer, thereby improving the life and efficiency of the device. Known materials can be used without restriction, and the substances exemplified in the description of the hole injection layer can be used, but are not limited thereto. The 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.

[0305] The hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed using the same conditions as the electron injection layer. When the organic light-emitting device according to one embodiment of the present specification includes another hole blocking layer in addition to the hole blocking layer comprising the above chemical formula 1, specifically, Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0306] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0307] The organic light-emitting device according to the present specification can be included in various electronic devices for use. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0308] Modes for Carrying Out the Invention

[0309] Below, in order to specifically describe this specification, examples and comparative examples will be cited for detailed description. However, the examples and comparative examples of this specification can be deformed into various forms, and it is not interpreted that the scope of this specification is limited to the examples and comparative examples described in detail below. The examples and comparative examples of this specification are provided to more completely describe this specification to those skilled in the art.

[0310] [Example]

[0311] Example 1: Preparation of Compound E1

[0312]

[0313] Structural formula E1-A (56.6 g, 87.0 mmol) and AlCl3 (0.5 g) were added to C6D6 (400 ml) and stirred for 30 minutes. After the reaction was completed, D2O (60 ml) was added, stirred for 30 minutes, and trimethylamine (6 ml) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over anhydrous magnesium sulfate (MgSO4) and recrystallized from ethyl acetate to obtain the above-mentioned compound E1 (17.1 g, 30%) with an average deuterium substitution rate of 15%.

[0314] MS:[M+H] + =656

[0315] Example 2: Preparation of Compound E2

[0316]

[0317] The above-mentioned compound E2 having an average deuterium substitution rate of 16% was produced by the same method as the production method of Example 1 except that the respective starting materials were used as in the above-mentioned reaction formula.

[0318] MS:[M+H] + =667

[0319] Example 3: Preparation of Compound E3

[0320]

[0321] The above-mentioned compound E3 having an average deuterium substitution rate of 17% was produced by the same method as the production method of Example 1 except that the starting materials were used as shown in the above reaction formula.

[0322] MS:[M+H] + =640

[0323] Example 4: Preparation of Compound E4

[0324]

[0325] Structural formula E4-A (47.6 g, 86.9 mmol) and AlCl3 (0.5 g) were added to C6D6 (400 ml) and stirred for 1 hour. After the reaction was completed, D2O (60 ml) was added, stirred for 30 minutes, and trimethylamine (6 ml) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over anhydrous magnesium sulfate (MgSO4) and recrystallized from ethyl acetate to obtain the above-mentioned compound E4 (16.5 g, 34%) with an average deuterium substitution rate of 40%.

[0326] MS:[M+H] + =640

[0327] Example 5: Preparation of Compound E5

[0328]

[0329] The above-mentioned compound E5 having an average deuterium substitution rate of 32% was produced by the same method as the production method of Example 4 except that the starting materials were used as in the above-mentioned reaction formula.

[0330] MS:[M+H] + =660

[0331] Example 6: Preparation of Compound E6

[0332]

[0333] The above-mentioned compound E6 having an average deuterium substitution rate of 33% was produced by the same method as the production method of Example 4 except that the starting materials were used as shown in the above reaction formula.

[0334] MS:[M+H] + =661

[0335] Example 7: Preparation of Compound E7

[0336]

[0337] Structural formula E7-A (59.6 g, 86.9 mmol) and AlCl3 (0.5 g) were added to C6D6 (400 ml) and stirred for 2 hours. After the reaction was completed, D2O (60 ml) was added, stirred for 30 minutes, and trimethylamine (6 ml) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over anhydrous magnesium sulfate (MgSO4) and recrystallized from ethyl acetate to obtain the above-mentioned compound E7 (14.7 g, 24%) with an average deuterium substitution rate of 63%.

[0338] MS:[M+H] + =705

[0339] Example 8: Preparation of Compound E8

[0340]

[0341] The above-mentioned compound E8 having an average deuterium substitution rate of 57% was produced by the same method as the production method of Example 7 except that the starting materials were used as shown in the above reaction formula.

[0342] MS:[M+H] + =762

[0343] Example 9: Preparation of Compound E9

[0344]

[0345] Structural formula E7-A (46.7 g, 86.9 mmol) and AlCl3 (0.5 g) were added to C6D6 (400 ml) and stirred for 4 hours. After the reaction was completed, D2O (60 ml) was added, stirred for 30 minutes, and trimethylamine (6 ml) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over anhydrous magnesium sulfate (MgSO4) and recrystallized from ethyl acetate to obtain the above-mentioned compound E9 (14.7 g, 24%) with an average deuterium substitution rate of 89%.

[0346] MS:[M+H] + =562

[0347] Example 10: Preparation of Compound E10

[0348]

[0349] The compound E10 having an average deuterium substitution rate of 80% was produced by the same method as in Example 9 except that the starting materials were used as in the above reaction formula.

[0350] MS:[M+H] + =599

[0351] Example 11: Preparation of Compound E11

[0352]

[0353] The above-mentioned compound E11 having an average deuterium substitution rate of 6.45% was produced by the same method as the production method of Example 1 except that the starting materials were used as shown in the above reaction formula.

[0354] MS:[M+H] + =664

[0355] [Experimental example]

[0356] Experimental Example 1

[0357] ITO (indium tin oxide) is used The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0358] On the ITO transparent electrode prepared in this way, the following compound HI-A was applied as On the hole injection layer, hexanitrile hexaazatriphenylene (HAT, ) and the following compound HT-A Vacuum deposition was sequentially performed to form a hole transport layer.

[0359] Next, on the hole transport layer, a film with a thickness of The following compounds BH and BD were vacuum-deposited at a weight ratio of 25:1 to form a light-emitting layer. On the light-emitting layer, the compound E1 prepared in Example 1 was vacuum-deposited to form a light-emitting layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A cathode is formed by evaporation with a thickness of .

[0360]

[0361] In the above process, the evaporation rate of organic matter is maintained / second, the cathode lithium fluoride maintains / second evaporation speed, aluminum maintains The evaporation speed is 1×10 / s. During evaporation, the vacuum degree is maintained at 1×10 -7 ~5×10 -8 A support is provided to produce an organic light-emitting device.

[0362] Experimental Examples 2 to 11

[0363] An organic light-emitting device was manufactured by the same method as in Experimental Example 1, except that the compound shown in Table 1 below was used instead of Compound E1 in Experimental Example 1.

[0364] Comparative Experimental Examples 1 to 3

[0365] An organic light-emitting device was manufactured by the same method as in Experimental Example 1, except that the compounds in Table 1 below were used instead of Compound E1 in Experimental Example 1. Compounds ET-1 to ET-3 used in Table 1 below are as follows.

[0366]

[0367] For the organic light-emitting devices manufactured in the above experimental examples and comparative experimental examples, the 2 The driving voltage, luminous efficiency and color coordinates were measured at a current density of 20 mA / cm 2 The time (T90) until the initial luminance reaches 90% was measured at a current density of . The results are shown in Table 1 below.

[0368] [Table 1]

[0369]

[0370] As described in Table 1, it was confirmed that the organic light emitting device using the compound represented by Chemical Formula 1 of the present invention exhibited excellent characteristics in terms of lifespan (T90).

[0371] By comparing Experimental Examples 1 to 11 of Table 1 above with Comparative Experimental Examples 1 and 2, it can be confirmed that the organic light-emitting device including the compound of Chemical Formula 1 of the present invention exhibits significantly superior characteristics in terms of lifespan compared to the organic light-emitting device using the compound not substituted with deuterium.

[0372] In addition, Comparative Experimental Example 3 does not contain -L1-HAr of Chemical Formula 1 in the specification of the present application, but instead has a structure with a heterocyclic ring on the benzenes on both sides of fluoranthene. It is confirmed that the organic light-emitting devices of Experimental Examples 1 to 11 containing the compound of Chemical Formula 1 of the present application have significantly superior voltage, efficiency and life compared with the organic light-emitting device of Comparative Experimental Example 3.

Claims

1. A compound of the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, D is deuterium, n is an integer greater than or equal to 1, L1 is a directly bonded, or deuterium-substituted or unsubstituted arylene group, HAr is a substituted or unsubstituted heteroaryl group.

2. The compound according to claim 1, wherein The dipole moment value of the chemical formula 1 is 1 Debye or more.

3. The compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 2 to 4: [Chemical formula 2] [Chemical formula 3] [Chemical formula 4] In the chemical formulae 2 to 4, The definitions of D, n, L1 and HAr are the same as those in Chemical Formula 1.

4. The compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 1-1 to 1-3: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] In the chemical formulas 1-1 to 1-3, The definitions of D, n and L1 are the same as those in the chemical formula 1, At least one of Y1 to Y5 is N, and the rest of Y1 to Y5 that are not N are the same as or different from each other and are each independently CR1, X1 is O, S, CR5R6 or NR7, Y6 is CR8 or N, Y7 is CR9 or N, R1 to R9 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or any one or more adjacent pairs of groups are combined to form a substituted or unsubstituted ring.

5. The compound according to claim 1, wherein The above-mentioned L1 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, which is directly bonded or substituted or unsubstituted with deuterium.

6. The compound according to claim 1, wherein The HAr is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms that is substituted or unsubstituted with deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a combination thereof.

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

8. The compound according to claim 1, wherein The deuterium substitution rate of the Chemical Formula 1 is 10% to 90%.

9. An organic light-emitting device, comprising: The first electrode, The second electrode, a light emitting layer disposed between the first electrode and the second electrode, and A first organic layer disposed between the light-emitting layer and the second electrode, The first organic layer comprises the compound according to any one of claims 1 to 8.

10. The organic light emitting device according to claim 9, wherein: The first organic layer is a hole blocking layer, an electron regulating layer, an electron injection layer, an electron transport layer, or any one of an electron injection and transport layer.

11. The organic light emitting device according to claim 9, wherein: The compound has a dipole moment value of 1 Debye or more.

Images