Organic compound and organic light emitting device comprising same

Abstract

The present specification provides an organic compound represented by Chemical Formula 1 and an organic light-emitting diode comprising the same.

Description

Technology Field

[0001] This specification relates to organic compounds and organic light-emitting diodes containing the same. Background Technology

[0002] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting diodes (OLEDs) that utilize this phenomenon typically have a structure comprising an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to enhance the efficiency and stability of the OLED; for example, it may consist of a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, and an electron injection layer. In the structure of such an OLED, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic layer. When the injected holes and electrons meet, an exciton is formed, and light is emitted when this exciton returns to the ground state.

[0003] The development of new materials for organic light-emitting diodes as described above is continuously required. Prior art literature

[0004] Chinese Published Patent Application No. 114621274 The problem to be solved

[0005] The present specification provides an organic compound and an organic light-emitting diode containing the same. means of solving the problem

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

[0007] [Chemical Formula 1]

[0008]

[0009] [Chemical Formula 1-A] [Chemical Formula 1-B]

[0010]

[0011] In the above chemical formula 1,

[0012] One or more of R1 to R10 are bonded to L1 of the above chemical formula 1-A, and

[0013] One or more of R1 to R10 that are not bonded to L1 of Formula 1-A are bonded to L2 of Formula 1-B, and

[0014] The R1 to R10 that are not bonded to L1 of Formula 1-A and are not bonded to L2 of Formula 1-B are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0015] L1 and L2 are the same or different from each other, and each is independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0016] n and m are integers from 1 to 4, respectively, and

[0017] Ar1 is the following chemical formula 1-C, and

[0018] [Chemical Formula 1-C]

[0019]

[0020] In the above chemical formula 1-C,

[0021] R101 to R110 are the same or different from one another, and each independently is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and one of R101 to R108 is bonded to L1, and

[0022] Ar2 is the following chemical formula 1-D and

[0023] [Chemical Formula 1-D]

[0024]

[0025] In the above chemical formula 1-D,

[0026] X is O or S, and

[0027] R201 to R208 are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and at least one pair of adjacent R201 to R208 are combined with each other to form at least one substituted or unsubstituted ring group, and

[0028] The above substituted or unsubstituted ring group is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted benzofuran ring; or a substituted or unsubstituted benzothiophene ring, and

[0029] The above-mentioned substituted or unsubstituted ring; or any one of R201 to R208 that does not form the above-mentioned substituted or unsubstituted ring is combined with L2, and

[0030] However, in the case where the adjacent R201 to R208 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring, any one of R101, R103 to R106 and R108 of Formula 1-C is bonded to L1, or any one of R101 to R108 not bonded to L1 of Formula 1-C, R201 to R208 not bonded to L2 of Formula 1-D, and any one of the substituted or unsubstituted ring not bonded to L2 of Formula 1-D must be substituted with one or more substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, or substituted or unsubstituted aryl groups, and

[0031] When the adjacent R201 to R208 are combined with each other to form a substituted or unsubstituted benzofuran ring or a substituted or unsubstituted benzothiophene ring, R2, R3, R6, and R7 of Formula 1 are the same or different from each other, and each is independently hydrogen or deuterium, and

[0032] * is the site that combines with chemical formula 1.

[0033] In addition, one embodiment of the present specification provides an organic light-emitting device comprising an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers comprise the aforementioned organic compound. Effects of the invention

[0034] The organic compounds described in this specification can be used as materials for the organic layer of an organic light-emitting diode.

[0035] An organic compound according to at least one embodiment of the present specification can improve efficiency, low driving voltage, and / or lifespan characteristics in an organic light-emitting diode. Brief explanation of the drawing

[0036] FIG. 1 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a light-emitting layer (6), and a cathode (9) are sequentially stacked. FIG. 2 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light-emitting layer (6), a hole blocking layer (7), an electron injection and transport layer (8) and a cathode (9) are sequentially stacked. Figure 3 is an MS graph of compound A. Specific details for implementing the invention

[0037] The present specification will be described in more detail below.

[0038] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0039] In this specification, when it is said that a member is located "on" another member, this includes not only cases where a member is in contact with another member, but also cases where another member exists between the two members.

[0040] In this specification, "*" indicates a position that is bonded to a chemical formula or compound.

[0041] Examples of substituents in this specification are described below, but are not limited thereto.

[0042] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, any site where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0043] In this specification, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group (-CN); silyl group; alkyl group; cycloalkyl group; alkoxy group; aryloxy group; alkyl sulfoxy group; aryl sulfoxy group; alkyl sulfoxy group; aryl sulfoxy group; alkenyl group; amine group; aryl group; or heterocyclic group, or is substituted with a substituent in which two or more of the exemplified substituents are connected, or has no substituents. For example, “a substituent in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

[0044] In this specification, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; nitro group; hydroxyl group; amino group; alkoxy group; aryloxy group; alkyl group; cycloalkyl group; alkenyl group; alkynyl group; aryl group; and heterocyclic group, or is substituted with a substituent in which two or more of the exemplified substituents are connected, or has no substituents.

[0045] In this specification, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; alkyl group; aryl group; and heterocyclic group, or that it is substituted with two or more of the exemplified substituents linked together, or that it has no substituents.

[0046] Examples of the above substituents are described below, but are not limited thereto.

[0047] In this specification, examples of halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0048] In the present specification, the silyl group may be represented by the chemical formula -SiYaYbYc, and Ya, Yb, and Yc may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specifically, the silyl group may be a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc., but is not limited thereto.

[0049] In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of alkyl groups include, butyl, n-butyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited thereto.

[0050] In the present specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferred to have 1 to 20 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but is not limited thereto.

[0051] Substituents comprising alkyl groups, alkoxy groups and other alkyl groups described in this specification include both straight-chain and broken-chain forms.

[0052] In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited to these.

[0053] In the present specification, the alkynyl group is a substituent comprising a triple bond between carbon atoms, and may be a straight chain or a branched chain. The number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkynyl group is 2 to 10.

[0054] In the present specification, the cycloalkyl group is not particularly limited, but it is preferable that it has 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to yet another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, etc., are included but are not limited thereto.

[0055] In this specification, the amine group is -NH2, and the amine group may be substituted with the aforementioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms in the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the number of carbon atoms in the amine group is 1 to 20. According to one embodiment, the number of carbon atoms in the amine group is 1 to 10. Specific examples of substituted amine groups include, but are not limited to, methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, 9,9-dimethylfluorenylphenylamine, pyridylphenylamine, diphenylamine, phenylpyridylamine, naphthylamine, biphenylamine, anthracenylamine, dibenzofuranylphenylamine, 9-methylanthracenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, and diphenylamine groups.

[0056] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. As a monocyclic aryl group, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quadrphenyl group, etc., but is not limited thereto. As a polycyclic aryl group, the aryl group may be a naphthyl group, anthracenyl group, phenanthrene group, pyrenyl group, perylenyl group, triphenylene group, chrysenyl group, fluorenyl group, triphenylene group, etc., but is not limited thereto.

[0057] In this specification, the aryl group among the aryloxy group and the arylamine group may be subject to the description of the aryl group described above.

[0058] In this specification, the description of the alkyl group described above may be applied to the alkyl group among the alkyl thioxy group and the alkyl sulfoxy group.

[0059] In this specification, the description of the aryl group described above may be applied to the aryl group among the aryl thioxy group and the aryl sulfoxy group.

[0060] In the present specification, the heterocyclic group is a ring group comprising one or more heteroatoms N, O, P, S, Si, and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of heterocyclic groups include, but are not limited to, pyridine groups, pyrrole groups, pyrimidine groups, quinoline groups, pyridazinyl groups, furan groups, thiophene groups, imidazole groups, pyrazol groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, benzocarbazole groups, naphthobenzofuran groups, benzonaphthiophene groups, indenocarbazole groups, triazinyl groups, etc.

[0061] In this specification, the description of the aforementioned heterocyclic group may apply, except that the heteroaryl group is aromatic.

[0062] In this specification, the description of the aryl group may apply except that the arylene group is divalent.

[0063] In this specification, the description of the heteroaryl group may apply except that the heteroaryl group is divalent.

[0064] In the present specification, in a substituted or unsubstituted ring formed by combining adjacent groups, "ring" means a hydrocarbon ring; or a heteroring.

[0065] For example, when adjacent groups combine to form a ring, a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heteroring; a substituted or unsubstituted aromatic heteroring; or a condensed ring thereof may be formed. The hydrocarbon ring refers to a ring composed only of carbon and hydrogen atoms. The heteroring refers to a ring containing one or more elements selected from N, O, P, S, Si, and Se. In this specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heteroring, and aromatic heteroring may be monocyclic or polycyclic.

[0066] In this specification, an aliphatic hydrocarbon ring refers to a non-aromatic ring composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.

[0067] In this specification, an aromatic hydrocarbon ring refers to an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include, but are not limited to, benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, and spirofluorene. In this specification, an aromatic hydrocarbon ring may be interpreted as having the same meaning as an aryl group.

[0068] In this specification, an aliphatic heterocycle means an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephane, azocaine, thiocane, etc.

[0069] In this specification, an aromatic heterocycle means an aromatic ring comprising one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazol, oxazole, isooxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazolin, quinoxaline, naphthiridine, acridine, phenanthridine, diazanaphthalene, driazindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, Examples include imidazopyridine, phenoxazine, indolocarbazole, indenocabazole, etc., but are not limited to these.

[0070] Preferred embodiments of the present invention are described in detail below. However, embodiments of the present invention may be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

[0071] The organic compound of Chemical Formula 1 below will be described in detail below.

[0072] [Chemical Formula 1]

[0073]

[0074] [Chemical Formula 1-A] [Chemical Formula 1-B]

[0075]

[0076] In the above chemical formula 1,

[0077] One or more of R1 to R10 are bonded to L1 of the above chemical formula 1-A, and

[0078] One or more of R1 to R10 that are not bonded to L1 of Formula 1-A are bonded to L2 of Formula 1-B, and

[0079] The R1 to R10 that are not bonded to L1 of Formula 1-A and are not bonded to L2 of Formula 1-B are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0080] L1 and L2 are the same or different from each other, and each is independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0081] n and m are integers from 1 to 4, respectively, and

[0082] Ar1 is the following chemical formula 1-C, and

[0083] [Chemical Formula 1-C]

[0084]

[0085] In the above chemical formula 1-C,

[0086] R101 to R110 are the same or different from one another, and each independently is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and one of R101 to R108 is bonded to L1, and

[0087] Ar2 is the following chemical formula 1-D and

[0088] [Chemical Formula 1-D]

[0089]

[0090] In the above chemical formula 1-D,

[0091] X is O or S, and

[0092] R201 to R208 are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and at least one pair of adjacent R201 to R208 are combined with each other to form at least one substituted or unsubstituted ring group, and

[0093] The above substituted or unsubstituted ring group is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted benzofuran ring; or a substituted or unsubstituted benzothiophene ring, and

[0094] The above-mentioned substituted or unsubstituted ring; or any one of R201 to R208 that does not form the above-mentioned substituted or unsubstituted ring is combined with L2, and

[0095] However, in the case where the adjacent R201 to R208 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring, any one of R101, R103 to R106 and R108 of Formula 1-C is bonded to L1, or any one of R101 to R108 not bonded to L1 of Formula 1-C, R201 to R208 not bonded to L2 of Formula 1-D, and any one of the substituted or unsubstituted ring not bonded to L2 of Formula 1-D must be substituted with one or more substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, or substituted or unsubstituted aryl groups, and

[0096] When the adjacent R201 to R208 are combined with each other to form a substituted or unsubstituted benzofuran ring or a substituted or unsubstituted benzothiophene ring, R2, R3, R6, and R7 of Formula 1 are the same or different from each other, and each is independently hydrogen or deuterium, and

[0097] * is the site that combines with chemical formula 1.

[0098] In one embodiment of the present specification, The substituted or unsubstituted ring group of the above chemical formula 1-D is an organic compound represented by 1-D-1 to 1-D-9 below.

[0099] [Chemical Formula 1-D-1] [Chemical Formula 1-D-2] [Chemical Formula 1-D-3]

[0100]

[0101] [Chemical Formula 1-D-4] [Chemical Formula 1-D-5] [Chemical Formula 1-D-6]

[0102]

[0103] [Formula 1-D-7] [Formula 1-D-8] [Formula 1-D-9]

[0104]

[0105] In the above chemical formulas 1-D-1 to 1-D-9,

[0106] Ra to Rc are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or optionally combine with an adjacent group to form a substituted or unsubstituted cyclic group, or combine with L2, and

[0107] p is an integer from 1 to 4, and if p is 2 or greater, the 2 or greater Ra, Rb, or Rc are the same or different from each other, and

[0108] q is an integer from 1 to 5, and if q is 2 or greater, the 2 or greater Rb or Rc are the same or different from each other, and

[0109] r is an integer from 1 to 6, and if r is 2 or more, the 2 or more Ra are equal to or different from each other, and

[0110] s is 1 or 2, and when s is 2, the Ra of 2 are the same or different from each other, and

[0111] * is a site that is bonded to an adjacent pair of R201 to R208 of chemical formula 1-D.

[0112] In one embodiment of the present specification, p is an integer from 1 to 4.

[0113] In one embodiment of the present specification, p is 4.

[0114] In one embodiment of the present specification, p is 3.

[0115] In one embodiment of the present specification, p is 2.

[0116] In one embodiment of the present specification, p is 1.

[0117] In one embodiment of the present specification, q is an integer from 1 to 5.

[0118] In one embodiment of the present specification, q is 5.

[0119] In one embodiment of the present specification, q is 4.

[0120] In one embodiment of the present specification, q is 3.

[0121] In one embodiment of the present specification, q is 2.

[0122] In one embodiment of the present specification, q is 1.

[0123] In one embodiment of the present specification, r is an integer from 1 to 6.

[0124] In one embodiment of the present specification, r is 6.

[0125] In one embodiment of the present specification, r is 5.

[0126] In one embodiment of the present specification, r is 4.

[0127] In one embodiment of the present specification, r is 3.

[0128] In one embodiment of the present specification, r is 2.

[0129] In one embodiment of the present specification, r is 1.

[0130] In one embodiment of the present specification, s is an integer of 1 or 6.

[0131] In one embodiment of the present specification, s is 2.

[0132] In one embodiment of the present specification, s is 1.

[0133] In one embodiment of the present specification, Ra to Rc are the same or different from each other and each independently forms a hydrogen; a deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or optionally combine with an adjacent group to form a substituted or unsubstituted cyclic group.

[0134] In one embodiment of the present specification, Ra to Rc are the same or different from each other and each independently forms a hydrogen; a deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or optionally combine with an adjacent group to form a substituted or unsubstituted cyclic group.

[0135] In one embodiment of the present specification, Ra to Rc are the same or different from each other and each independently forms a hydrogen; a deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms, or optionally combine with an adjacent group to form a substituted or unsubstituted cyclic group.

[0136] In one embodiment of the present specification, Ra to Rc are the same or different from each other and each independently is hydrogen or deuterium or optionally combines with an adjacent group to form a substituted or unsubstituted ring group.

[0137] In one embodiment of the present specification, Ra to Rc are the same or different from each other and each independently forms a hydrogen or optionally combines with an adjacent group to form a substituted or unsubstituted ring group.

[0138] In one embodiment of the present specification, Ra to Rc are the same or different from each other, and each is independently deuterium or optionally combines with an adjacent group to form a substituted or unsubstituted ring group.

[0139] In one embodiment of the present specification, The above chemical formula 1 is an organic compound that is any one of the following chemical formulas 1-1 to 1-4.

[0140] [Chemical Formula 1-1] [Chemical Formula 1-2]

[0141]

[0142] [Chemical Formula 1-3] [Chemical Formula 1-4]

[0143]

[0144] In the above chemical formulas 1-1 to 1-4,

[0145] The definitions of L1, L2, Ar2, R101 to R110, n, and m are the same as the definitions in Chemical Formula 1 above, and

[0146] The above R1 to R8 are hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0147] In the present specification, the above chemical formula 1 is the above chemical formula 1-1.

[0148] In the present specification, the above chemical formula 1 is the above chemical formula 1-2.

[0149] In the present specification, the above chemical formula 1 is the above chemical formula 1-3.

[0150] In the present specification, the above chemical formula 1 is the above chemical formula 1-4.

[0151] In one embodiment of the present specification, The above chemical formula 1 is an organic compound that is any one of the following chemical formulas 1-5 to 1-8.

[0152] [Chemical Formula 1-5] [Chemical Formula 1-6]

[0153]

[0154] [Chemical Formula 1-7] [Chemical Formula 1-8]

[0155]

[0156] In the above chemical formulas 1-5 to 1-8,

[0157] The definitions of L1, L2, Ar1, X, R201 to R208, n, and m are the same as the definitions in Chemical Formula 1 above, and

[0158] The above R1 to R8 are hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0159] In the present specification, the above chemical formula 1 is the above chemical formula 1-5.

[0160] In the present specification, the above chemical formula 1 is the above chemical formula 1-6.

[0161] In the present specification, the above chemical formula 1 is the above chemical formula 1-7.

[0162] In the present specification, the above chemical formula 1 is the above chemical formula 1-8.

[0163] In one embodiment of the present specification, R1 to R10 that are not bonded to L1 of Formula 1-A and are not bonded to L2 of Formula 1-B are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0164] In one embodiment of the present specification, R1 to R10 that are not bonded to L1 of Formula 1-A and are not bonded to L2 of Formula 1-B are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0165] In one embodiment of the present specification, R1 to R10 that are not bonded to L1 of Formula 1-A and are not bonded to L2 of Formula 1-B are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0166] In one embodiment of the present specification, R1 to R10 that are not bonded to L1 of Formula 1-A and are not bonded to L2 of Formula 1-B are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0167] In one embodiment of the present specification, R1 to R10 that are not bonded to L1 of Formula 1-A and are not bonded to L2 of Formula 1-B are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

[0168] In one embodiment of the present specification, R1 to R10 that are not bonded to L1 of Formula 1-A and are not bonded to L2 of Formula 1-B are the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quadrphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted furan group; a substituted or unsubstituted benzofuran group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted naphthobenzofuran group; a substituted or unsubstituted thiophene group; a substituted or unsubstituted benzothiophene group; a substituted or unsubstituted dibenzothiophene group; It is a substituted or unsubstituted naphthobenzothiophen group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted pyridyl group; or a substituted or unsubstituted pyrimidyl group.

[0169] In one embodiment of the present specification, R1 to R10 that are not bonded to L1 of Formula 1-A and are not bonded to L2 of Formula 1-B are the same or different from each other and are each independently hydrogen or deuterium.

[0170] In one embodiment of the present specification, R1 to R10 that are not bonded to L1 of Formula 1-A and are not bonded to L2 of Formula 1-B are hydrogen.

[0171] In one embodiment of the present specification, R1 to R10 that are not bonded to L1 of Formula 1-A and are not bonded to L2 of Formula 1-B are deuterium.

[0172] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

[0173] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; an arylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms; or a heteroarylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms.

[0174] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; an arylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms; or a heteroarylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms.

[0175] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; an arylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms; or a heteroarylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms.

[0176] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; an arylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms; or a heteroarylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms.

[0177] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted biphenylene group.

[0178] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; a naphthylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms; or a biphenylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms.

[0179] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; a naphthylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms; or a biphenylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms.

[0180] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; a naphthylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms; or a biphenylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms.

[0181] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; a naphthylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms; or a biphenylene group substituted or unsubstituted with a deuterium, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms.

[0182] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently direct bonded; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted fluorenylene group.

[0183] In one embodiment of the present specification, L1 and L2 are directly coupled.

[0184] In one embodiment of the present specification, n is an integer from 1 to 4.

[0185] In one embodiment of the present specification, n is 4.

[0186] In one embodiment of the present specification, n is 3.

[0187] In one embodiment of the present specification, n is 2.

[0188] In one embodiment of the present specification, n is 1.

[0189] In one embodiment of the present specification, m is an integer from 1 to 4.

[0190] In one embodiment of the present specification, m is 4.

[0191] In one embodiment of the present specification, m is 3.

[0192] In one embodiment of the present specification, m is 2.

[0193] In one embodiment of the present specification, m is 1.

[0194] In one embodiment of the present specification, the R101 to R110 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and one of the R101 to R108 must be bonded to L1.

[0195] In one embodiment of the present specification, the R101 to R110 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and one of the R101 to R108 must be bonded to L1.

[0196] In one embodiment of the present specification, the R101 to R110 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, and one of the R101 to R108 must be bonded to L1.

[0197] In one embodiment of the present specification, the R101 to R110 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms, and one of the R101 to R108 must be bonded to L1.

[0198] In one embodiment of the present specification, R101 to R110 are the same or different from one another and each independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted isoprogyl group; a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted tetrahydronaphthalene group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quadrphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted furan group; a substituted or unsubstituted benzofuran group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted thiophene group; a substituted or unsubstituted benzothiophene group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted naphthobenzothiophene group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted pyridyl group; or a substituted or unsubstituted pyrimidyl group, wherein one of R101 to R108 must be bonded to L1.

[0199] The above X is O or S.

[0200] The above X is O.

[0201] The above X is S.

[0202] In one embodiment of the present specification, R201 to R208 are the same or different from one another and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and at least one pair of adjacent R201 to R208 are combined with each other to form at least one substituted or unsubstituted ring group.

[0203] In one embodiment of the present specification, R201 to R208 are the same or different from one another and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and at least one pair of adjacent R201 to R208 are combined with each other to form at least one substituted or unsubstituted ring group.

[0204] In one embodiment of the present specification, R201 to R208 are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and at least one pair of adjacent R201 to R208 are combined with each other to form at least one substituted or unsubstituted ring group.

[0205] In one embodiment of the present specification, R201 to R208 are the same or different from one another and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, and at least one pair of adjacent R201 to R208 are combined with each other to form at least one substituted or unsubstituted ring group.

[0206] In one embodiment of the present specification, R201 to R208 are the same or different from one another and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms; a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms, and at least one pair of adjacent R201 to R208 are combined with each other to form at least one substituted or unsubstituted ring group.

[0207] In one embodiment of the present specification, R201 to R208 are the same or different from one another and each independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted isoprogyl group; a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quadrphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted furan group; a substituted or unsubstituted benzofuran group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted naphthobenzofuran group; a substituted or unsubstituted thiophene group; A substituted or unsubstituted benzothiophen group; a substituted or unsubstituted dibenzothiophen group; a substituted or unsubstituted naphthobenzothiophen group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted pyridyl group; or a substituted or unsubstituted pyrimidyl group, wherein at least one pair of adjacent R201 to R208 must combine with each other to form at least one substituted or unsubstituted ring group.

[0208] According to one embodiment of the present specification, the substituted or unsubstituted ring; or any one of R201 to R208 that does not form the substituted or unsubstituted ring is combined with L2.

[0209] According to one embodiment of the present specification, R201 to R208 that are not combined with L2 are the same or different from each other and are each independently hydrogen; or deuterium.

[0210] According to one embodiment of the present specification, R201 to R208 that are not combined with L2 are the same or different from each other and are each independently hydrogen.

[0211] According to one embodiment of the present specification, R201 to R208 that are not combined with L2 are the same or different from each other and are each independently deuterium.

[0212] According to one embodiment of the present specification, the substituted or unsubstituted ring group is a substituted or unsubstituted aromatic hydrocarbon ring group having 4 to 30 carbon atoms; a substituted or unsubstituted benzofuran ring group; or a substituted or unsubstituted benzothiophene ring group.

[0213] According to one embodiment of the present specification, when adjacent R201 to R208 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring, any one of R101, R103 to R106 and R108 of Formula 1-C is bonded to L1, or any one of R101 to R108 not bonded to L1 of Formula 1-C, R201 to R208 not bonded to L2 of Formula 1-D, and any one of the substituted or unsubstituted ring groups not bonded to L2 of Formula 1-D must be substituted with at least one substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0214] According to one embodiment of the present specification, when the adjacent R201 to R208 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring, any one of R101, R103 to R106 and R108 of Formula 1-C is bonded to L1, or R101 to R108 not bonded to L1 of Formula 1-C, R201 to R208 not bonded to L2 of Formula 1-D, and any one of the substituted or unsubstituted ring groups not bonded to L2 of Formula 1-D must be a phenyl group substituted or unsubstituted with one or more deuterium-substituted or unsubstituted phenyl group, a naphthyl group substituted or unsubstituted with one or more deuterium-substituted or unsubstituted naphthyl group, a biphenyl group substituted or unsubstituted with one or more deuterium-substituted or unsubstituted methyl group, a propyl group substituted or unsubstituted with one or more deuterium-substituted or unsubstituted tert-butyl group, or a deuterium-substituted or unsubstituted alkyl group. It is substituted with a tetrahydronaphthalene group.

[0215] According to one embodiment of the present specification, R9 of Formula 1 is bonded to L1 of Formula 1-A, R10 of Formula 1 is bonded to L2 of Formula 1-B, and R1 to R8 of Formula 1 are each independently hydrogen; deuterium; or a phenyl group substituted or unsubstituted with deuterium.

[0216] According to one embodiment of the present specification, R9 of Formula 1 is bonded to L1 of Formula 1-A, R10 of Formula 1 is bonded to L2 of Formula 1-B, and R1 to R8 of Formula 1 are all deuterium.

[0217] According to one embodiment of the present specification, R9 of Formula 1 is bonded to L1 of Formula 1-A, R10 of Formula 1 is bonded to L2 of Formula 1-B, and R1 to R8 of Formula 1 are all hydrogen.

[0218] In one embodiment of the present specification, the chemical formula 1 is an organic compound that is any one of the following compounds.

[0219] According to one embodiment of the present specification, the deuterium substitution rate of Formula 1 is 15% or more.

[0220] According to one embodiment of the present specification, the deuterium substitution rate of Formula 1 is 30% or more.

[0221] According to one embodiment of the present specification, the deuterium substitution rate of Formula 1 is 40% or more.

[0222] According to one embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 is 50% or more.

[0223] According to one embodiment of the present specification, the deuterium substitution rate of Formula 1 is 60% or more.

[0224] According to one embodiment of the present specification, the deuterium substitution rate of Formula 1 is 70% or more.

[0225] According to one embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 is 80% or more.

[0226] According to one embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 is 90% or more.

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

[0228] According to one embodiment of the present specification, when the above formula 1 includes deuterium, the following effects are achieved. Specifically, physicochemical properties such as chemical bond lengths associated with deuterium differ from those of hydrogen, and the elongation amplitude of CD bonds is smaller than that of CH bonds, so the van der Waals radius of deuterium is smaller than that of hydrogen, and generally, CD bonds can be shown to be shorter and stronger than CH bonds. Therefore, when hydrogen at a substitutable position in the above formula 1 is substituted with deuterium, the ground state energy is lowered, and as the bond length between deuterium and carbon is shortened, the molecular hardcore volume is reduced, and accordingly, electrical polarizability can be reduced, and by weakening intermolecular interactions, the thin film volume can be increased. In addition, these characteristics can lower the crystallinity of the thin film, i.e., create an amorphous state, which can generally be effective in increasing the lifespan and driving characteristics of organic light-emitting diodes, and can improve heat resistance compared to conventional organic light-emitting diodes.

[0229] In this specification, "containing deuterium," "deuterated," or "deuterated" means that hydrogen at a substitutable position of a compound is substituted with deuterium.

[0230] In this specification, "deuteriumized" means a compound or group in which all hydrogens in the molecule are substituted with deuterium, and has the same meaning as "100% deuteriumized."

[0231] In this specification, "X% deuterated," "degree of deuteration X%," or "deuterium substitution rate X%" means that X% of the hydrogens at substitutable positions in the structure are replaced with deuterium. For example, if the structure is dibenzofuran, "25% deuterated" of the dibenzofuran, "degree of deuteration 25%" of the dibenzofuran, or "deuterium substitution rate 25%" of the dibenzofuran means that 2 of the 8 hydrogens at substitutable positions of the dibenzofuran are replaced with deuterium.

[0232] In this specification, "deuteriumization" or "deuterium substitution rate" refers to nuclear magnetic resonance spectroscopy ( 1 It can be confirmed by known methods such as ¹H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry).

[0233] Specifically, nuclear magnetic resonance spectroscopy ( 1 When analyzing "deuteration" or "deuteration substitution rate" using ¹H NMR, DMF (dimethylformamide) is added as an internal standard, 1 Through the integration ratio on the H NMR, the degree of deuteration or deuterium substitution rate can be calculated from the total integrated amount of the peak.

[0234] In addition, when analyzing the "deuteration" or "deuteration rate" through TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), the substitution rate can be calculated based on the maximum value (median) of the distribution of molecular weights at the end of the reaction. For example, when analyzing the deuteration of the following compound A, the molecular weight of the following starting material is 506, and the maximum value (median) of the molecular weight of the following compound A in the MS graph of Fig. 3 is 527. Since 21 of the 26 hydrogens at substitutable positions of the following starting material were substituted with deuteration, it can be calculated that approximately 81% of the hydrogens were deuterated.

[0235]

[0236] [Starting Material] [Compound A]

[0237] In this specification, D means deuterium.

[0238] In one embodiment of the present specification, the chemical formula 1 is an organic compound that is any one of the following compounds.

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249] An organic compound of Formula 1 according to one embodiment of this specification may have a core structure prepared as described in the following preparation example. Substituents may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

[0250] In this specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the organic compound of Formula 1. In addition, in this specification, the HOMO and LUMO energy levels of the compound can also be controlled by introducing various substituents into the core structure of such a structure.

[0251] In addition, the present specification provides an organic light-emitting device comprising the organic compound described above.

[0252] In this specification, when it is stated that a component is located "on" another component, this includes not only cases where a component is in contact with another component, but also cases where another component exists between the two components.

[0253] An organic light-emitting device according to the present specification comprises an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers comprise an organic compound represented by the aforementioned chemical formula 1.

[0254] The organic layer of the organic light-emitting device of the present specification may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure comprising one or more layers among a hole transport layer, a hole injection layer, an electron control layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole control layer, and an electron transport and injection layer as organic layers. However, the structure of the organic light-emitting device of the present specification is not limited thereto and may include a smaller or larger number of organic layers.

[0255] In the organic light-emitting device of the present specification, the organic light-emitting device comprises a light-emitting layer, and the light-emitting layer may comprise the organic compound.

[0256] For example, the organic compound of the above chemical formula 1 may be included as a host of the light-emitting layer.

[0257] According to one embodiment of the present specification, the light-emitting layer comprises a dopant, and the dopant comprises a fluorescent dopant.

[0258] According to one embodiment of the present specification, the fluorescent dopant is a pyrene-based compound or a non-pyrene-based compound.

[0259] According to one embodiment of the present specification, the non-pyrene compound comprises a boron compound.

[0260] According to one embodiment of the present specification, the light-emitting layer further comprises one or more hosts different from the compound of Formula 1.

[0261] In one embodiment of the present specification, a host different from the compound of Formula 1 comprises a compound of Formula H-1 below.

[0262] In one embodiment of the present specification, the light-emitting layer of the organic light-emitting element comprises the organic compound as a host and further comprises one type of host represented by the following chemical formula H-1, which is different from the organic compound.

[0263] [Chemical Formula H-1]

[0264]

[0265] In the above chemical formula H-1,

[0266] L301 and L302 are the same or different from each other, and each is independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heterocyclic group, and

[0267] Ar301 and Ar302 are the same or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0268] R301 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0269] r301 is an integer from 1 to 7, and if r301 is 2 or more, the 2 or more R301s are the same or different from each other.

[0270] According to one embodiment of the present specification, the formula H-1 is represented by the following compound.

[0271]

[0272] A host different from the compound of Chemical Formula 1 above may be used without limitation if it is an anthracene-based host used in the art, provided it is different from Chemical Formula 1 above, but is not limited thereto.

[0273] According to one embodiment of the present specification, the light-emitting layer comprises a host and a dopant.

[0274] According to one embodiment of the present specification, the light-emitting layer comprises a host and a dopant, and the host comprises a compound represented by the chemical formula 1.

[0275] According to one embodiment of the present specification, the dopant is a blue dopant.

[0276] According to one embodiment of the present specification, the organic light-emitting element is a blue organic light-emitting element.

[0277] According to one embodiment of the present specification, the light-emitting layer comprises a host and a dopant, the host comprises a compound represented by the chemical formula 1, and the dopant comprises one or more selected from pyrene-based compounds and non-pyrene-based compounds.

[0278] According to one embodiment of the present specification, the light-emitting layer comprises a host and a dopant, and the weight ratio of the host and the dopant in the light-emitting layer is 8:2 to 99:1.

[0279] According to one embodiment of the present specification, the light-emitting layer comprises a host and a dopant, and the weight ratio of the host and the dopant in the light-emitting layer is 8:2 to 95:5.

[0280] According to one embodiment of the present specification, the light-emitting layer comprises a host and a dopant, and the weight ratio of the host and the dopant in the light-emitting layer is 90:10 to 99:1.

[0281] According to another embodiment of the present specification, at least one of the first electrode and the second electrode further comprises a capping layer provided on the opposite side of the surface facing the organic layer.

[0282] The above capping layer is formed to prevent a significant amount of light loss through total internal reflection in an organic light-emitting device, and the capping layer has the performance to sufficiently protect the lower cathode and light-emitting layer from external moisture penetration or contamination, and has a high refractive index so as to prevent light loss due to total internal reflection.

[0283] According to another embodiment of the present specification, the capping layer may be provided on each of the opposite side of the surface of the first electrode facing the organic layer and the opposite side of the surface of the second electrode facing the organic layer.

[0284] According to another embodiment of the present specification, the capping layer may be provided on the opposite side of the surface of the first electrode facing the organic layer.

[0285] According to another embodiment of the present specification, the capping layer may be provided on each of the opposite sides of the surface of the second electrode facing the organic layer.

[0286] According to one embodiment of the present specification, the organic light-emitting device further comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

[0287] According to one embodiment of the present specification, the organic light-emitting element comprises: a first electrode; a second electrode; a light-emitting layer provided between the first electrode and the second electrode; and two or more organic layers provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0288] According to one embodiment of the present specification, two or more organic layers between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, may be selected from the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a hole injection and transport layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer.

[0289] 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 materials that are the same or different from each other.

[0290] According to one embodiment of the present specification, the first electrode is an anode or a cathode.

[0291] According to one embodiment of the present specification, the second electrode is a cathode or an anode.

[0292] According to one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device of a normal type structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0293] 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, and an anode are sequentially stacked on a substrate.

[0294] For example, the structure of an organic light-emitting device according to one embodiment of the present specification is illustrated in FIGS. 1 and 2. FIGS. 1 and 2 illustrate an organic light-emitting device and are not limited thereto.

[0295] FIG. 1 illustrates the structure of an organic light-emitting device in which a first electrode (2), a light-emitting layer (4), and a second electrode (3) are sequentially stacked on a substrate (1). The compound is included in the light-emitting layer.

[0296] FIG. 2 illustrates the structure of an organic light-emitting device in which a first electrode (2), a hole injection layer (5), a hole transport layer (6), a hole control layer (7), a light-emitting layer (4), an electron control layer (8), an electron transport layer (9), an electron injection layer (10), a second electrode (3), and a capping layer (11) are sequentially stacked on a substrate (1). The compound is included in the light-emitting layer.

[0297] The organic light-emitting device of the present specification may be manufactured using materials and methods known in the art, except that the light-emitting layer, or the light-emitting layer comprises the compound, i.e., the compound of Formula 1.

[0298] When the above organic light-emitting element includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0299] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, the device can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation, forming an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to such a method, the organic light-emitting device can be manufactured by sequentially depositing a second electrode material, an organic layer, and a first electrode material on a substrate.

[0300] In addition, the compound represented by Chemical Formula 1 above can be formed as an organic layer by vacuum deposition as well as solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

[0301] In addition to this method, an organic light-emitting device may also be fabricated by sequentially depositing an organic layer from a second electrode material and a first electrode material on a substrate. However, the manufacturing method is not limited to this.

[0302] As the first electrode material, a material with a large work function is generally preferred to facilitate hole injection into the organic layer. Examples include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metal and oxide 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, but are not limited thereto.

[0303] The above second electrode material is preferably a material with a small work function to facilitate electron injection into an organic layer. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structural materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0304] The above-described light-emitting layer may include a host material and a dopant material. In the case where an additional light-emitting layer is included in addition to the light-emitting layer comprising the compound of Formula 1 according to one embodiment of the present specification, the host material may include condensed and / or non-condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0305] According to one embodiment of the present specification, the host comprises a compound represented by Formula 2, but is not limited thereto.

[0306] The above dopant materials include aromatic amine derivatives, styramine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and periplantene having arylamine groups. In addition, styramine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, wherein one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamine groups are substituted or unsubstituted. Specifically, styramine, styryldiamine, styryltriamine, styryltetraamine, etc. are examples, but are not limited thereto. In addition, metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0307] According to one embodiment of the present specification, the dopant material comprises a compound of the following chemical formula D-1 or D-2, but is not limited thereto.

[0308] [Chemical Formula D-1]

[0309]

[0310] In the above chemical formula D-1,

[0311] L101 and L102 are the same or different from each other and are each independently directly bonded; or are substituted or unsubstituted arylene groups, and

[0312] Ar101 to Ar104 are the same or different from each other and are each independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups, and

[0313] [Chemical Formula D-2]

[0314]

[0315] In the above chemical formula D-2,

[0316] T1 to T5 are the same or different from each other, and each independently is hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; or a substituted or unsubstituted aryl group, and

[0317] t3 and t4 are integers from 1 to 4, respectively, and

[0318] t5 is an integer from 1 to 3, and

[0319] If the above t3 is 2 or more, the above 2 or more T3s are the same or different from each other, and

[0320] If the above t4 is 2 or more, the above 2 or more T4s are the same or different from each other, and

[0321] If the above t5 is 2 or more, the above 2 or more T5s are the same or different from each other.

[0322] According to one embodiment of the present specification, L101 and L102 are directly coupled.

[0323] According to one embodiment of the present specification, the Ar101 to Ar104 are the same or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; or substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms.

[0324] According to one embodiment of the present specification, the Ar101 to Ar104 are the same or different from each other and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0325] According to one embodiment of the present specification, the Ar101 to Ar104 are the same or different from each other and are each independently a phenyl group substituted with a methyl group; or a dibenzofuran group.

[0326] According to one embodiment of the present specification, the formula D-1 is represented by the following compound.

[0327]

[0328] According to one embodiment of the present specification, T1 to T5 are the same or different from each other and are each independently hydrogen; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0329] According to one embodiment of the present specification, T1 to T5 are the same or different from each other and are each independently hydrogen; a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

[0330] According to one embodiment of the present specification, T1 to T5 are the same or different from each other and are each independently hydrogen; a methyl group; a tert-butyl group; a diphenylamine group; or a phenyl group substituted or unsubstituted with a methyl group or a tert-butyl group.

[0331] According to one embodiment of the present specification, the formula D-2 is represented by the following compound.

[0332]

[0333] The hole injection layer described above is a layer that receives holes from an electrode. It is desirable for the hole injection material to have the ability to transport holes, thereby having an excellent hole injection effect for the hole receiving effect from the anode and for the light-emitting layer or light-emitting material. In addition, it is desirable for the material to have an excellent ability to prevent the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material. In addition, it is desirable for the material to have an excellent thin film formation ability. Furthermore, it is desirable for the HOMO (highest occupied molecular orbital) of the hole injection material to be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic materials; hexanitrile-hexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; and polythiophene-based conductive polymers such as anthraquinone and polyaniline.

[0334] The hole injection layer described above is a layer that receives holes from an electrode. It is desirable for the hole injection material to have the ability to transport holes, thereby having an excellent hole injection effect for the hole receiving effect from the anode and for the light-emitting layer or light-emitting material. In addition, it is desirable for the material to have an excellent ability to prevent the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material. In addition, it is desirable for the material to have an excellent thin film formation ability. Furthermore, it is desirable for the HOMO (highest occupied molecular orbital) of the hole injection material to be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic materials; hexanitrile-hexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; and polythiophene-based conductive polymers such as anthraquinone and polyaniline.

[0335] According to one embodiment of the present specification, the hole injection layer comprises a compound represented by the following chemical formula HI-1, but is not limited thereto.

[0336] [Chemical Formula HI-1]

[0337]

[0338] In the above chemical formula HI-1,

[0339] At least one of X'1 to X'6 is N, and the rest are CH, and

[0340] R309 to R314 are the same or different from each other and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0341] According to one embodiment of the present specification, X'1 to X'6 are N.

[0342] According to one embodiment of the present specification, R309 to R314 are cyano groups.

[0343] According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound.

[0344]

[0345] The hole transport layer described above is a layer that receives holes from the hole injection layer and transports them to the emissive layer. As for the hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the emissive layer is preferably a material with high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions.

[0346] According to one embodiment of the present specification, the hole transport layer or hole control layer comprises a compound of the following formula HT-1, but is not limited thereto.

[0347] [Chemical Formula HT-1]

[0348]

[0349] In the above chemical formula HT-1,

[0350] R315 to R317 are the same or different from one another and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring, and

[0351] r315 is an integer from 1 to 5, and if r315 is 2 or more, the 2 or more R315s are the same or different from each other,

[0352] r316 is an integer from 1 to 5, and if r316 is 2 or more, the 2 or more R316s are the same or different from each other.

[0353] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

[0354] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; a fluorene group; and combinations thereof.

[0355] According to one embodiment of the present specification, R315 and R316 are the same or different from each other and are each independently substituted or unsubstituted aryl groups, or they combine with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0356] According to one embodiment of the present specification, R315 and R316 are the same or different from each other and are each independently a phenyl group or a phenanthrene group, or combine with adjacent groups to form an indene substituted with a methyl group.

[0357] According to one embodiment of the present specification, the chemical formula HT-1 is represented by any one of the following compounds.

[0358]

[0359] The hole control layer described above is a layer capable of improving the lifespan and efficiency of a device by controlling the smooth injection of holes transported from the hole transport layer into the light-emitting layer and preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. Known materials may be used without limitation 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 performs both hole injection and hole transport simultaneously.

[0360] Examples of the chemical formula HT-I may be applied as materials for the electronic control layer, but are not limited thereto.

[0361] The above electron control layer is a layer that controls the smooth injection of electrons transferred from the electron transport layer into the light-emitting layer, and known materials can be used without limitation.

[0362] According to one embodiment of the present specification, the electronic control layer comprises a compound of the following formula EG-1, but is not limited thereto.

[0363] [Chemical Formula EG-1]

[0364]

[0365] In the above chemical formula EG-1,

[0366] At least one of G1 to G18 is -L5-Ar5 and the remainder is hydrogen, or G1 and G18 are connected by -L51- to form a substituted or unsubstituted ring,

[0367] L5 is a direct bond; or a substituted or unsubstituted arylene group, and

[0368] Ar5 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0369] L51 is O; or S.

[0370] According to one embodiment of the present specification, L51 is O.

[0371] According to one embodiment of the present specification, L51 is S.

[0372] According to one embodiment of the present specification, G1 and G18 are connected by -L51- to form a substituted or unsubstituted heterocycle.

[0373] According to one embodiment of the present specification, G1 and G18 are connected by -L51- to form a substituted or unsubstituted xanthen ring; or a substituted or unsubstituted thioxanthen ring.

[0374] According to one embodiment of the present specification, G1 and G18 are connected by -O- to form a substituted or unsubstituted xanthen ring.

[0375] According to one embodiment of the present specification, G1 and G18 are connected by -S- to form a substituted or unsubstituted thioxanthen ring.

[0376] According to one embodiment of the present specification, G1 and G18 are connected by -O- to form a xanthen ring.

[0377] According to one embodiment of the present specification, G1 and G18 are connected by -S- to form a thioxanthen ring.

[0378] According to one embodiment of the present specification, L5 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0379] According to one embodiment of the present specification, the L5 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0380] According to one embodiment of the present specification, L5 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0381] According to one embodiment of the present specification, L5 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0382] According to one embodiment of the present specification, the L5 is a direct bond; or a phenylene group.

[0383] According to one embodiment of the present specification, the Ar5 is a substituted or unsubstituted triazine group.

[0384] According to one embodiment of the present specification, the Ar5 is a triazine group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0385] According to one embodiment of the present specification, the Ar5 is a triazine group substituted with a phenyl group.

[0386] According to one embodiment of the present specification, the EG-1 is represented by the following compound.

[0387]

[0388] The electron transport layer described above is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. As for the electron transport material, a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer is preferred, and a material with high electron mobility is desirable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material, as used in the prior art. In particular, a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically, examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum layer or a silver layer.

[0389] According to one embodiment of the present specification, the electron transport layer comprises a compound of the following chemical formula ET-1, but is not limited thereto.

[0390] [Chemical Formula ET-1]

[0391]

[0392] In the above chemical formula ET-1,

[0393] At least one of Z11 to Z13 is N, and the rest are CH, and

[0394] L601 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0395] Ar601 and Ar602 are the same or different from each other, and each is an independently substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0396] l601 is an integer from 1 to 5, and if l601 is 2 or more, the 2 or more L601s are the same or different from each other.

[0397] According to one embodiment of the present specification, the L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0398] According to one embodiment of the present specification, the L601 is a phenylene group; a biphenyllylene group; or a naphthylene group.

[0399] According to one embodiment of the present specification, Ar601 and Ar602 are the same or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms.

[0400] According to one embodiment of the present specification, Ar601 and Ar602 are phenyl groups.

[0401] According to one embodiment of the present specification, the chemical formula ET-1 is represented by the following compound.

[0402]

[0403] The electron injection layer is a layer that receives electrons from an electrode. It is desirable for the electron injection material to have excellent electron transport ability and to have an electron receiving effect from the second electrode, as well as an excellent electron injection effect on the emitting layer or emitting material. In addition, it is desirable for the material to prevent excitons generated in the emitting layer from moving to the hole injection layer and to have excellent thin film formation ability. Specifically, examples include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but are not limited thereto.

[0404] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, Examples include bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, but are not limited thereto.

[0405] According to one embodiment of the specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. The electron injection and transport layer may use the materials exemplified in the electron transport layer and electron injection layer, but is not limited thereto.

[0406] According to one embodiment of the present specification, the electron injection and transport layer may further comprise a metal complex compound. The metal complex compound is as described above.

[0407] The above-mentioned electron control layer is a layer capable of improving the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the emissive layer and entering the hole injection layer. Known materials may be used without limitation and can be formed between the emissive layer and the hole injection layer, between the emissive layer and the hole transport layer, or between the emissive layer and a layer that performs both hole injection and hole transport simultaneously.

[0408] Examples of the chemical formula HT-I may be applied as materials for the electronic control layer, but are not limited thereto.

[0409] The hole control layer above is a layer that prevents holes from reaching the cathode and can generally be formed under the same conditions as the electron injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc. are used, but are not limited thereto.

[0410] The above capping layer is formed to prevent a significant amount of light loss through total internal reflection in an organic light-emitting device. The capping layer has the performance to sufficiently protect the lower cathode and light-emitting layer from external moisture penetration or contamination, and has a high refractive index to prevent light loss due to total internal reflection, and allows the use of conventional materials without limitation.

[0411] According to one embodiment of the present specification, the capping layer comprises a compound represented by the following chemical formula CP-1, but is not limited thereto.

[0412] [Chemical Formula CP-1]

[0413]

[0414] In the above chemical formula CP-1,

[0415] L501 and L502 are the same or different from each other, and each is independently a directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0416] R501 and Ar501 to Ar504 are the same or different from each other and are each independently substituted or unsubstituted aryl groups; or are substituted or unsubstituted heteroaryl groups, or adjacent groups are combined to form substituted or unsubstituted rings.

[0417] According to one embodiment of the present specification, L501 and L502 are the same or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic arylene groups having 6 to 30 carbon atoms.

[0418] According to one embodiment of the present specification, L501 and L502 are phenylene groups.

[0419] According to one embodiment of the present specification, R501 and Ar501 to Ar504 are the same or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, or they combine with adjacent groups to form substituted or unsubstituted monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms.

[0420] According to one embodiment of the present specification, R501 and Ar501 to Ar504 are phenyl groups, or they combine with adjacent groups to form a carbazole that is substituted or unsubstituted with a phenyl group.

[0421] According to one embodiment of the present specification, the Ar501 combines with the L501 to form a carbazole substituted with a phenyl group.

[0422] According to one embodiment of the present specification, the Ar503 combines with the L503 to form a carbazole substituted with a phenyl group.

[0423] According to one embodiment of the present specification, the chemical formula CP-1 is represented by the following compound.

[0424]

[0425] The organic light-emitting device according to the present specification may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0426] The organic light-emitting element according to the present specification may be included in and used in various electronic devices. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0427] Hereinafter, to specifically explain this specification, examples will be described in detail. However, the embodiments according to this specification may be modified in various different forms, and the scope of this application is not to be interpreted as being limited to the embodiments described below. The embodiments of this application are provided to more completely explain this specification to those with average knowledge in the art.

[0429] Preparation Example 1 (Synthesis of Chemical Formula 1)

[0430] 1) Synthesis of Chemical Formulas A1 and B1

[0431]

[0432] SM1 (one of A0 or B0, 1 eq) and SM2 (1.1 eq) were added to tetrahydrofuran (THF) at °C (excess), followed by the addition of a 2 M aqueous potassium carbonate solution (30 volume ratio relative to THF), and then tetracitriphenyl-phosphinopalladium (2 mol%). The mixture was then heated and stirred at 85 °C for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the aqueous potassium carbonate solution was removed to separate the layers, and the mixture was columned with hexane and ethyl acetate to prepare the above chemical formulas A1 and B1 (A1-1 to A1-6 and B1-1 to B1-3), respectively.

[0433] A1-1 to A1-6 of Table 1 and B1-1 to B1-3 of Table 2 were synthesized by the same method as the synthesis method of the above chemical formulas A1 and B1, except that SM1 and SM2 were changed to the substances of Tables 1 and 2 below.

[0434]

[0435]

[0436] 2) Synthesis of Chemical Formulas A2 and B2

[0437]

[0438] SM1 (one of A1 or B1, 1 eq) and SM2 (one of P1 or P2, 1.1 eq) were added to tetrahydrofuran (THF) (excess), followed by the addition of a 2 M aqueous potassium carbonate solution (30 volume ratio relative to THF), and then tetracitriphenyl-phosphinopalladium (2 mol%). The mixture was then heated and stirred at 85°C for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the aqueous potassium carbonate solution was removed to separate the layers, and the mixture was columned with hexane and ethyl acetate to prepare the above chemical formulas A2 and B2 (A2-1 to A2-4 and B2-1 to B2-2), respectively.

[0439] A2-1 to A2-4 of Table 3 and B2-1 to B2-2 of Table 4 were synthesized in the same way as the synthesis method of the above chemical formulas A2 and B2, except that SM1 and SM2 were changed to the substances of Tables 3 and 4 below.

[0440]

[0441]

[0442] 3) Synthesis of Chemical Formulas A3 and B3

[0443]

[0444]

[0445]

[0446]

[0447] SM1 (one of A1 and A2 or B1 and B2, 1 eq) and SM2 (1.3 eq) were added to 1,4-dioxane (12 times the mass ratio of SM1), potassium acetate (3 eq) was added, and the mixture was stirred and refluxed. Bis(diphenylpispino)ferrocene dichloropalladium (0.05 eq) was added after stirring in 1,4-dioxane for 5 minutes, and after confirming the end of the reaction after 2 hours, the mixture was cooled to room temperature. After adding ethanol and water, the mixture was filtered and purified by recrystallization with ethyl acetate and ethanol to prepare the above chemical formulas A3 and B3 (A3-1 to A3-9 and B3-1 to B3-27), respectively.

[0448] A3-1 to A3-9 of Table 5 and B3-1 to B3-27 of Table 6 were synthesized in the same manner as the synthesis method of the above chemical formulas A3 and B3, except that SM1 and SM2 were changed to the substances of Tables 5 and 6 below.

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0457] 4) Composition of Int 1.

[0458]

[0459] SM1 (one of B3, 1 eq) and SM2 (1.1 eq or 2.1 eq) were added to tetrahydrofuran (THF) (excess), followed by the addition of a 2 M aqueous potassium carbonate solution (30 volume ratio relative to THF), and then tetracitriphenyl-phosphinopalladium (2 mol%). The mixture was then heated and stirred at 85°C for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the aqueous potassium carbonate solution was removed to separate the layers, and the mixture was recrystallized with chloroform and ethyl acetate to prepare the above chemical formulas int. (int 1-1 to int 1-27).

[0460] Int 1-1 to int 1-27 of [Table 7] were synthesized in the same way as the synthesis method of the above chemical formula int 1, except that SM1 and SM2 were changed to the substances of Table 7 below.

[0461]

[0462]

[0463]

[0464]

[0465]

[0467] 5) Composition of Int 2.

[0468]

[0469] SM1 (one of int 1., 1 eq) was dissolved in chloroform (excess), the temperature was lowered to 0°C, and after temperature stabilization, N-bromosuccinimide (1 eq) was dissolved in DMF (excess) and added dropwise. Then, the reaction mixture was heated to room temperature, stirred for 1 hour, and 1N HCl (excess) was added to terminate the reaction. After the reaction was completed, the reaction was separated and the solvent was removed, and the residue was subjected to silica column chromatography (ethyl acetate / hexane 1:15) to prepare the chemical formula int 2. (int 2-1. to int 2-27.).

[0470] In the synthesis method of the above chemical formula int 2., int 2-1 to int 2-27 of Table 8 were synthesized in the same way, except that SM1 and SM2 were changed to the substances of Table 8 below.

[0471]

[0472]

[0473]

[0474]

[0475]

[0476] 6) Synthesis of Chemical Formula 1

[0477]

[0478] SM1 (one of int 2. 1 eq) and SM2 (1.1 eq) were added to tetrahydrofuran (THF) (excess), followed by the addition of a 2 M aqueous potassium carbonate solution (30 volume ratio relative to THF), and then tetracitriphenyl-phosphinopalladium (2 mol%). The mixture was then heated and stirred at 85°C for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the aqueous potassium carbonate solution was removed to separate the layers, and the mixture was columned with hexane and ethyl acetate to prepare the above-mentioned Formula 1 (Compounds 1 to 27).

[0479] Compounds 1 to 27 of [Table 9] were synthesized in the same way as the synthesis method of the above chemical formula int., except that SM1 and SM2 were changed to the substances of Table 9 below.

[0480]

[0481]

[0482]

[0483]

[0484]

[0485]

[0486] 7) Synthesis of Chemical Formula 1D

[0487]

[0488] The reactant (1 eq) and trifluoromethanesulfonic acid (cat.) were added to C6D6 (mass ratio of 10 to 50 times the reactant) and stirred at 70°C for 10 to 100 minutes. After the reaction was finished, D2O (excess) was added and stirred for 30 minutes, after which trimethylamine (excess) was added dropwise. The reaction mixture was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried with MgSO4, then heated with toluene to recrystallize, thereby obtaining the products (compounds 28 to 31) of Table 10 below.

[0489]

[0490] [Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate is determined based on the maximum m / z (M+) value]

[0492] <Example 1> Manufacturing of OLED

[0493] A substrate with ITO / Ag / ITO deposited as an anode at 70 Å / 1000 Å / 70 Å was cut into 50 mm x 50 mm x 0.5 mm pieces, placed in distilled water containing a dispersant, and cleaned using ultrasound. A detergent from Fischer Co. was used, and distilled water that had been double-filtered through a Millipore Co. filter was utilized. After washing the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. Following the distilled water washing, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol solvents, followed by drying.

[0494] A hole injection layer was formed on the thus prepared anode by thermal vacuum deposition of HI-1 to a thickness of 50 Å, and a hole transport layer was formed by vacuum deposition of HT1, a hole-transporting material, to a thickness of 1150 Å on top of it. Next, a hole control layer was formed using EB1 (150 Å). Then, the emissive layer was formed by vacuum deposition of the host compound 1 synthesized in Preparation Example 1 and dopant BD1 (2 wt%) to a thickness of 360 Å. Subsequently, an electron control layer was formed by depositing HB1 to a thickness of 50 Å, and an electron transport layer with a thickness of 250 Å was formed by mixing compound ET1 and Liq in a 5:5 (mass ratio). Sequentially, magnesium and lithium fluoride (LiF) with a thickness of 50 Å were deposited as the electron injection layer. <eil>After forming the film, a 200 Å layer of magnesium and silver (1:4) was formed as the cathode, and then CP1 was deposited to a depth of 600 Å to complete the device. During the above process, the deposition rate of the organic material was maintained at 1 Å / sec.

[0495]

[0496] [Comparative Examples 1 to 17 and Examples 1 to 35]

[0497] In Comparative Examples 1 to 17 and Examples 1 to 35 above, devices were manufactured in the same manner as Example 1, except that the material of the light-emitting layer was a material listed in Table 11 below.

[0498] The devices prepared in Comparative Examples 1 to 17 and Examples 1 to 35 above at 20 mA / cm 2 The driving voltage, luminous efficiency, and time to reach 95% of the initial brightness (LT95) were measured at the current density. The results are shown in Table 11 below.

[0499]

[0500]

[0501]

[0502]

[0503]

[0504] The result of Table 11 above is a case in which the device structure has a light-emitting layer formed therein, the host of the light-emitting layer is a single host, and the compound of the claim of the present invention is composed of the host of the light-emitting layer.

[0505] Comparative Example 1 is a case where phenanthrene 2 is bonded to the 10th position of anthracene and [a]naphthobenzofuran 2 is bonded to the 9th position of anthracene, and deuterium is introduced into anthracene and [a]naphthobenzofuran, which differs from the present invention in that additional substituents are introduced into phenanthrene or [a]naphthobenzofuran. Example 9 or Example 11 has additional aryl groups substituted as previously explained, and this results in carrier injection and migration speeds different from the comparative example, which can be confirmed to exhibit superior performance, particularly in terms of efficiency, in the device structure of the present invention.

[0506] Comparative Examples 2 and 3 are cases in which the skeleton has a structure in which phenanthrene 2 is bound to the 10th position of anthracene and phenanthrenodibenzofuran 1 or 2 is bound to the 9th position of anthracene, and this also differs from the present invention in the presence of additional substituents. As can be seen from the results of Comparative Example 1 and Example 9 or Example 11, the device can be seen that the device has excellent device performance, even though the binding position of phenanthrene is different or the introduction of substituents into the skeleton, as in Example 23 or Example 27, affects stability and electrical characteristics.

[0507] Comparative Examples 4 to 8 have the structure of the present claim but have a common structure in that an additional substituent is introduced at position 2 or 3 of anthracene and phenanthrene at position 10 of anthracene, and the structure of the corresponding backbone elongates the color coordinate due to the bonding of phenanthrene at position 2 and shows a decrease in overall electrical properties.

[0508] Comparative Examples 9 to 11 have a structure in which an oxazole-condensed dibenzofuran core is bonded to position 9 of anthracene and a phenanthrene is introduced to position 10, unlike the framework of the present invention; they exhibit lower voltage characteristics than the aforementioned Comparative Examples 1 to 8, but their efficiency and lifespan are inferior, which is more pronounced when compared based on Examples 1 to 35.

[0509] In Examples 1 to 27 of the present invention, it can be seen that a compound corresponding to Formula 1 was applied as a host of the light-emitting layer to enhance the role of hole injection and carrier balance, and the performance of the device was secured while maintaining the low voltage characteristics and efficiency that are currently considered important in blue light-emitting devices.

[0510] Examples 1 to 27 show that the compounds of the claimed scope serve as hosts for the light-emitting layer, and additional aryl groups are substituted into phenanthrene and naphthobenzofuran or heteroaryl condensed dibenzofuran (S-containing) units, thereby increasing the efficiency and improving the stability of the device, maximizing the effect of the deuterium of anthracene, and showing an additional increase in lifespan.

[0511] In addition, Examples 28 to 31 show an average additional lifespan increase of 10 to 15% through additional deuterium substitution, demonstrating that additional lifespan improvement is possible despite the disadvantage in terms of cost, and Examples 32 to 35 show that changing the dopant (pyrene dopant -> boron dopant) maintains the device trend while maintaining the change in dopant characteristics, thus demonstrating consistency in the device when various dopants are introduced.

[0513] <Example 36> Manufacturing of OLED

[0514] A substrate with ITO / Ag / ITO deposited as an anode at 70 Å / 1000 Å / 70 Å was cut into 50 mm x 50 mm x 0.5 mm pieces, placed in distilled water containing a dispersant, and cleaned using ultrasound. A detergent from Fischer Co. was used, and distilled water that had been double-filtered through a Millipore Co. filter was utilized. After washing the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. Following the distilled water washing, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol solvents, followed by drying.

[0515] A hole injection layer was formed on the thus prepared anode by thermal vacuum deposition of HI-1 to a thickness of 50 Å, and a hole transport layer was formed by vacuum deposition of HT1, a hole-transporting material, to a thickness of 1150 Å on top of it. Next, a hole control layer was formed using EB1 (150 Å). Then, as an emissive layer, the host compound 5 synthesized in Preparation Example 1, BH13, and dopant BD1 (2 wt%) were vacuum co-deposited to a thickness of 360 Å to form the emissive layer. Subsequently, an electron control layer was formed by depositing HB1 to a thickness of 50 Å, and an electron transport layer with a thickness of 250 Å was formed by mixing compound ET1 and Liq in a 5:5 (mass ratio). Sequentially, magnesium and lithium fluoride (LiF) with a thickness of 50 Å were deposited as an electron injection layer. <eil>After forming the film, a 200 Å layer was formed using magnesium and silver (1:4) as the cathode, and then CP1 was deposited to a thickness of 600 Å to complete the device. In the above process, the deposition rate of the organic material was 1 maintained.

[0516]

[0517] [Comparative Examples 18 to 23 and Examples 36 to 40]

[0518] In Comparative Examples 18 to 23 and Examples 36 to 40 above, the device was manufactured in the same manner as Example 27, except that the material of the light-emitting layer was a material listed in Table 2 below.

[0519] However, as shown in [Table 12], the host of the light-emitting layer is an example in which the light-emitting layer is formed by co-depositing two hosts through different evaporation sources during device fabrication.

[0520] The devices prepared in Comparative Examples 18 to 23 and Examples 36 to 40 above at 20 mA / cm 2 The driving voltage, luminous efficiency, and time to reach 95% of the initial brightness (LT95) were measured at the current density. The results are shown in [Table 12] below.

[0522]

[0523] The result of [Table 12] above is for the case where the host of the light-emitting layer is composed of a mixed host (anthracene 2-type mixed host).

[0524] Comparative Examples 18 to 21 presented examples in which BH13 and Comparative Example 14, which are widely used aryl-series anthracene compounds, formed a mixed host with BH1, BH2, BH5, and BH9 among the structures of Comparative Examples 1 to 12, and it was observed that devices forming a light-emitting layer of the corresponding combination showed device results that were partially improved in terms of voltage, efficiency, and lifetime. In addition, Comparative Examples 22 to 23 showed the same trend with the application of boron-series blue dopants.

[0525] Examples 36 to 40 are examples in which compounds 28 to 31 among the example compounds of the present claim are mixed hosts with the aforementioned BH13 or BH14 to observe device results, and it can be seen that the compounds of the present claim, which had superior characteristics compared to Comparative Examples 1 to 17, have the same tendency under mixed host conditions. Explanation of the symbols

[0526] 1: Substrate 2: First electrode 3: Second electrode 4: Emitting layer 5: Hole injection layer 6: Precision Transport Layer 7: Hole control layer 8: Electronic control layer 9: Electron transport layer 10: Electron injection layer 11: Capping layer< / eil> < / eil>

Claims

Claim 1 An organic light-emitting device comprising an anode; a cathode and one or more organic layers provided between the anode and the cathode, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises an organic compound of the following chemical formula 1 as a host, and further comprises one type of host represented by the following chemical formula H-1 that is different from the organic compound: [Chemical Formula 1] [Chemical Formula 1-A] [Chemical Formula 1-B] In the above Formula 1, R9 is bonded to L1 of Formula 1-A, R10 is bonded to L2 of Formula 1-B, R1 to R8 are the same or different from each other and are each independently hydrogen; deuterium; or a phenyl group substituted or unsubstituted with deuterium, L1 and L2 are the same or different from each other and are each independently directly bonded; a phenylene group substituted or unsubstituted with deuterium; or a biphenylene group substituted or unsubstituted with deuterium; or a naphthylene group substituted or unsubstituted with deuterium, n and m are each integers from 1 to 4, Ar1 is the following Formula 1-C, [Formula 1-C] In the above formula 1-C, R101 to R110 are the same or different from each other and each independently hydrogen; deuterium; a tert-butyl group substituted or unsubstituted with deuterium; an isopropyl group substituted or unsubstituted with deuterium; a cyclopentyl group substituted or unsubstituted with deuterium; a tetrahydronaphthalene group substituted or unsubstituted with deuterium or an alkyl group; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; or a naphthyl group substituted or unsubstituted with deuterium, and one of R101 to R108 is bonded to L1, and Ar2 is the following formula 1-D [Formula 1-D] In the above formula 1-D, X is O or S, and R201 to R208 are the same or different from each other and each independently hydrogen; deuterium; an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; or a phenyl group substituted or unsubstituted with deuterium, and at least one adjacent pair of R201 to R208 must be combined to form one or more ring groups substituted or unsubstituted with deuterium, an alkyl group, or an aryl group, and the ring group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group is an aromatic hydrocarbon ring group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; a benzofuran ring group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; or a benzothiophene ring group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; and the ring group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; Or, any one of R201 to R208 that does not form a ring group substituted or unsubstituted with a deuterium, alkyl group, or aryl group is bonded to L2, provided that adjacent R201 to R208 bond to each other to form an aromatic hydrocarbon ring group substituted or unsubstituted with a deuterium, alkyl group, or aryl group, at least one of the following 1) to 3), wherein 1) any one of R101, R103 to R106 and R108 of Formula 1-C is bonded to L1, and 2) at least one of R101 to R108 of Formula 1-C that is not bonded to L1 is a tert-butyl group substituted or unsubstituted with deuterium; an isopropyl group substituted or unsubstituted with deuterium; a cyclopentyl group substituted or unsubstituted with deuterium; a tetrahydronaphthalene group substituted or unsubstituted with deuterium or an alkyl group; a phenyl group substituted or unsubstituted with deuterium; Biphenyl groups substituted or unsubstituted with deuterium;A naphthyl group substituted or unsubstituted with deuterium, and 3) at least one of the substituents of the ring group substituted or unsubstituted with deuterium, alkyl, or aryl groups that is not bonded to L2 of Formula 1-D and R201 to R208 that is not bonded to L2 of Formula 1-D is an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; or a phenyl group substituted or unsubstituted with deuterium, and the adjacent R201 to R208 are bonded to each other to form a benzofuran ring substituted or unsubstituted with deuterium, alkyl, or aryl groups or a benzothiophene ring substituted or unsubstituted with deuterium, alkyl, or aryl groups, wherein R2, R3, R6, and R7 of Formula 1 are the same or different from each other and are each independently hydrogen or deuterium, and * is a site bonded to Formula 1, and in Formula 1; Excluding, [Chemical Formula H-1] In the above formula H-1, L301 and L302 are the same or different from each other and are each independently a direct bond; a phenylene group substituted or unsubstituted with deuterium; or a biphenylene group substituted or unsubstituted with deuterium, and Ar301 and Ar302 are the same or different from each other and are each independently hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; or a naphthyl group substituted or unsubstituted with deuterium, R301 is hydrogen; or deuterium, and r301 is an integer from 1 to 7, and if r301 is 2 or more, the 2 or more R301s are the same or different from each other. Claim 2 An organic light-emitting device according to claim 1, wherein the ring group substituted or unsubstituted with a deuterium, alkyl group, or aryl group of formula 1-D is represented by the following 1-D-1 to 1-D-9: [Formula 1-D-1] [Formula 1-D-2] [Formula 1-D-3] [Chemical Formula 1-D-4] [Chemical Formula 1-D-5] [Chemical Formula 1-D-6] [Formula 1-D-7] [Formula 1-D-8] [Formula 1-D-9] In the above chemical formulas 1-D-1 to 1-D-9, Ra to Rc are the same or different from each other, and each independently comprises hydrogen; deuterium; and an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; or an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, or optionally bonded to an adjacent group to form a ring group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group, or bonded to L2, p is an integer from 1 to 4, and if p is 2 or more, the 2 or more Ra, Rb, or Rc are the same or different from each other, q is an integer from 1 to 5, and if q is 2 or more, the 2 or more Rb or Rc are the same or different from each other, r is an integer from 1 to 6, and if r is 2 or more, the 2 or more Ra are the same or different from each other, s is 1 or 2, and if s is 2, the 2 Ra are the same or different from each other, and * is a site bonded to an adjacent pair of R201 to R208 of Formula 1-D. Claim 3 An organic light-emitting device according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In the above chemical formulas 1-1 to 1-4, the definitions of L1, L2, Ar2, R101 to R110, n, and m are the same as the definitions in chemical formula 1, and R1 to R8 are hydrogen; deuterium; or phenyl groups substituted or unsubstituted with deuterium. Claim 4 An organic light-emitting device according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-5 to 1-8: [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] In the above chemical formulas 1-5 to 1-8, the definitions of L1, L2, Ar1, X, R201 to R208, n and m are the same as the definitions in the above chemical formula 1, and R1 to R8 are hydrogen; deuterium; or phenyl groups substituted or unsubstituted with deuterium. Claim 5 An organic light-emitting diode according to claim 1, wherein R1 to R8 of the chemical formula 1 are all deuterium. Claim 6 An organic light-emitting diode according to claim 1, wherein R201 to R208 not combined with L2 are the same or different from each other, and each independently hydrogen; or deuterium. Claim 7 An organic light-emitting device according to claim 1, wherein the deuterium substitution rate of the chemical formula 1 is 15% or more. Claim 8 An organic light-emitting device according to claim 1, wherein chemical formula 1 is any one of the following compounds: . Claim 9 An organic light-emitting device according to claim 1, wherein the light-emitting layer comprises the organic compound as a host and further comprises a dopant. Claim 10 delete Claim 11 delete Claim 12 delete Claim 13 delete

Images