Organic compound and organic light-emitting device including same

Abstract

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

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2024-0035516 filed with the Korean Intellectual Property Office on March 14, 2024, the entire contents of which are incorporated herein by reference.

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

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

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

[0005] Prior art literature

[0006] Patent Literature

[0007] China Patent Gazette No. 114621274 Summary of the Invention

[0008] Technical issues

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

[0010] Solution to the problem

[0011] One embodiment of the present specification provides an organic compound represented by the following Chemical Formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014]

[0015] In the above Chemical Formula 1,

[0016] One or more of R1 to R10 is combined with L1 of the above Chemical Formula 1-A,

[0017] One or more of the R1 to R10 not bonded to L1 of the above Chemical Formula 1-A is bonded to L2 of the above Chemical Formula 1-B,

[0018] The R1 to R10 that are not bound to L1 of the above Chemical Formula 1-A and are not bound to L2 of the above Chemical Formula 1-B are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0019] L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0020] n and m are each an integer from 1 to 4,

[0021] Ar1 is the following chemical formula 1-C,

[0022] [Chemical Formula 1-C]

[0023]

[0024] In the above Chemical Formula 1-C,

[0025] R101 to R110 are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. One of the above R101 to R108 must be bound to L1.

[0026] Ar2 is the following chemical formula 1-D,

[0027] [Chemical Formula 1-D]

[0028]

[0029] In the above Chemical Formula 1-D,

[0030] X is O or S,

[0031] Any one of R201 to R206 is combined with the above-mentioned L2, and the rest are the same as or different from each other and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0032] However, when R203 or R205 is bonded to L2, four or more of R201 to R206 not bonded to L2 are hydrogen atoms, or either L1 or L2 is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group,

[0033] * indicates the site of bonding with Chemical Formula 1.

[0034] 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 disposed between the anode and the cathode, wherein one or more of the organic layers contains the organic compound.

[0035] Effects of the Invention

[0036] The organic compounds described in this specification can be used as materials for the organic layer of an organic light-emitting device.

[0037] The organic compound according to at least one embodiment of the present specification may achieve improved efficiency, lower driving voltage, and / or improved lifespan characteristics in an organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] Figure 1 The diagram shows an example of an organic light-emitting device in which a substrate 1 , a first electrode 2 , a light-emitting layer 4 , and a second electrode 3 are stacked in this order.

[0039] Figure 2 The diagram shows an example of an organic light-emitting device having a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, a hole regulation layer 7, a light-emitting layer 4, an electron regulation layer 8, an electron transport layer 9, an electron injection layer 10, a second electrode 3 and a covering layer 11 stacked in sequence.

[0040] Figure 3 This is the MS chart of compound A.

[0041] Explanation of symbols

[0042] 1: Substrate

[0043] 2: First electrode

[0044] 3: Second electrode

[0045] 4: Luminous layer

[0046] 5: Hole injection layer

[0047] 6: Hole transport layer

[0048] 7: Hole regulation layer

[0049] 8: Electronic adjustment layer

[0050] 9: Electron transport layer

[0051] 10: Electron injection layer

[0052] 11: Covering layer DETAILED DESCRIPTION

[0053] Next, this specification is described in more detail.

[0054] In this specification, when it is stated that a certain part “includes / comprising” a certain component, unless otherwise stated, it means that other components may be further included, rather than excluding other components.

[0055] In this specification, when it is stated that a certain component is located “on” another component, it includes not only a case where the certain component is in contact with the other component, but also a case where other components are present between the two components.

[0056] In this specification, "*" indicates a position bonded to a chemical formula or a compound.

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

[0058] The term "substituted" as used above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent. The position to be substituted is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are two or more substitutions, the two or more substituents may be the same or different from each other.

[0059] In this specification, the term "substituted or unsubstituted" refers to a group selected from deuterium, a halogen group, a nitrile group (-CN), a silyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, Arylthio Alkylsulfonyl Arylsulfonyl The group may be substituted with one or more substituents selected from the group consisting of alkenyl, amine, aryl, or heterocyclic groups, or may be substituted with a substituent consisting of two or more of the substituents listed above, or may be unsubstituted. For example, a "substituent consisting of two or more substituents" may be a biphenyl group. In other words, a biphenyl group may be an aryl group, or may be interpreted as a substituent consisting of two phenyl groups linked together.

[0060] In this specification, the term "substituted or unsubstituted" means that the group is substituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, an amino group, an alkoxy group, an aryloxy group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, and a heterocyclic group, or is substituted with a substituent formed by linking two or more of the substituents exemplified above, or has no substituent.

[0061] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, a halogen group, a nitrile group, an alkyl group, an aryl group and a heterocyclic group, or substituted by a substituent formed by linking two or more substituents among the substituents exemplified above, or having no substituent.

[0062] Examples of the above-mentioned substituents are described below, but are not limited thereto.

[0063] In the present specification, examples of the halogen group include fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0064] In this specification, a silyl group can be represented by the chemical formula -SiYaYbYc, where Ya, Yb, and Yc can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.

[0065] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, and n-octyl.

[0066] In this specification, the alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably has a carbon number of 1 to 20. Specifically, it may be a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, an n-pentoxy group, a neopentoxy group, an isopentoxy group, an n-hexyloxy group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, etc., but is not limited thereto.

[0067] The alkyl group, alkoxy group, and other substituents containing an alkyl moiety described in this specification include all linear and branched forms.

[0068] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. 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-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethen-1-yl, 2,2-bis(diphenyl-1-yl)ethen-1-yl, stilbene, and styryl, but are not limited thereto.

[0069] In the present specification, the alkynyl group is a substituent containing a triple bond between carbon atoms, and may be linear or branched. The number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkynyl group is 2 to 10.

[0070] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups.

[0071] In this specification, an amino group is -NH2, and the amino group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms in the substituted amino group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the number of carbon atoms in the amino group is 1 to 20. According to one embodiment, the number of carbon atoms in the amino group is 1 to 10. Specific examples of the substituted amino group include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9,9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthracenylamino, dibenzofuranylphenylamino, 9-methylanthrylamino, diphenylamino, phenylnaphthylamino, ditolylamino, phenyltolylamino, diphenylamino, etc., but are not limited thereto.

[0072] In this specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, quaterphenyl, etc., but is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, triphenylene, phenylene, fluorenyl, triphenylene, etc., but are not limited thereto.

[0073] In the present specification, the above description of the aryl group can be applied to the aryl group in the aryloxy group and the arylamine group.

[0074] In the present specification, the above description of the alkyl group can be applied to the alkyl group in the alkylthio group and the alkylsulfonyl group.

[0075] In the present specification, the above description of the aryl group can be applied to the aryl group in the arylthio group and the arylsulfonyl group.

[0076] In the present specification, a heterocyclic group is a ring group containing one or more of N, O, P, S, Si, and Se as heteroatoms. The number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 20. Examples of heterocyclic groups include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarbazolyl, and triazinyl.

[0077] In the present specification, a heteroaryl group is aromatic, and other than this, the above description of the heterocyclic group is applicable.

[0078] In the present specification, the above-mentioned arylene group is divalent, and the description of the above-mentioned aryl group is applicable except that the above-mentioned arylene group is divalent.

[0079] In the present specification, the heteroarylene group is divalent, and the same description as for the above-mentioned heteroaryl group applies except that the heteroarylene group is divalent.

[0080] In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, "ring" means a hydrocarbon ring or a heterocyclic ring.

[0081] For example, when combined with adjacent groups to form a ring, they may form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle, or a condensed ring thereof. The above-mentioned hydrocarbon ring refers to a ring composed solely of carbon and hydrogen atoms. The above-mentioned heterocycle refers to a ring containing one or more elements selected from N, O, P, S, Si, and Se. In this specification, the above-mentioned aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle may be monocyclic or polycyclic.

[0082] In this specification, an aliphatic hydrocarbon ring refers to a ring that is not aromatic and is 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.

[0083] 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 benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, Examples include, but are not limited to, pentacene, fluorene, indene, acenaphthylene, benzofluorene, and spirofluorene. In this specification, an aromatic hydrocarbon ring can be interpreted as having the same meaning as an aryl group.

[0084] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dihydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane Azoctane Thioctanes etc., but not limited thereto.

[0085] In this specification, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, Azoles, isocyanates Azoles, thiazoles, isothiazoles, triazoles, diazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, Azine, thiazine, di Olefins, triazines, tetrazines, isoquinolines, quinolines, quinones, quinazolines, quinoxalines, naphthyridines, acridines, phenanthridines, naphthyridines, triazaindene, indoles, indolizines, benzothiazoles, benzo azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phen Oxazine, indolocarbazole, indenocarbazole, etc., but are not limited to these.

[0086] Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention can be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

[0087] Next, the organic compound represented by the following Chemical Formula 1 will be described in detail.

[0088] [Chemical Formula 1]

[0089]

[0090]

[0091] In the above Chemical Formula 1,

[0092] One or more of R1 to R10 is combined with L1 of the above Chemical Formula 1-A,

[0093] One or more of the R1 to R10 not bonded to L1 of the above Chemical Formula 1-A is bonded to L2 of the above Chemical Formula 1-B,

[0094] The R1 to R10 that are not bound to L1 of the above Chemical Formula 1-A and are not bound to L2 of the above Chemical Formula 1-B are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0095] L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0096] n and m are each an integer from 1 to 4,

[0097] Ar1 is the following chemical formula 1-C,

[0098] [Chemical Formula 1-C]

[0099]

[0100] In the above Chemical Formula 1-C,

[0101] R101 to R110 are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. One of the above R101 to R108 must be bound to L1.

[0102] Ar2 is the following chemical formula 1-D,

[0103] [Chemical Formula 1-D]

[0104]

[0105] In the above Chemical Formula 1-D,

[0106] X is O or S,

[0107] Any one of R201 to R206 is combined with the above-mentioned L2, and the rest are the same as or different from each other and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0108] However, when R203 or R205 is bonded to L2, four or more of R201 to R206 not bonded to L2 are hydrogen atoms, or either L1 or L2 is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group,

[0109] * indicates the site of bonding with Chemical Formula 1.

[0110] In one embodiment of the present specification, the above Chemical Formula 1 is the following Chemical Formula 1-1 to Chemical Formula

[0111] An organic compound of any one of Formulas 1-4.

[0112]

[0113]

[0114] In the above Chemical Formulas 1-1 to 1-4,

[0115] The definitions of L1, L2, Ar2, R101 to R110, n and m are the same as those in the above Chemical Formula 1,

[0116] The above R1 to R8 are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0117] In this specification, the above Chemical Formula 1 is the above Chemical Formula 1-1.

[0118] In this specification, the above Chemical Formula 1 is the above Chemical Formula 1-2.

[0119] In this specification, the above Chemical Formula 1 refers to the above Chemical Formula 1-3.

[0120] In this specification, the above Chemical Formula 1 refers to the above Chemical Formula 1-4.

[0121] In one embodiment of the present specification, the above Chemical Formula 1 is the following Chemical Formulas 1-5 to

[0122] An organic compound of any one of formulas 1-10.

[0123]

[0124]

[0125]

[0126] In the above Chemical Formulas 1-5 to 1-10,

[0127] The definitions of L1, L2, Ar1, X, R1 to R8, R201 to R206, n and m are the same as those in the above Chemical Formula 1,

[0128] The above R1 to R8 are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0129] In the above Chemical Formulas 1-7 and 1-9, four or more of R201 to R206 are hydrogen atoms, or any one of L1 and L2 is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.

[0130] In this specification, the above Chemical Formula 1 refers to the above Chemical Formula 1-5.

[0131] In this specification, the above Chemical Formula 1 refers to the above Chemical Formula 1-6.

[0132] In this specification, the above Chemical Formula 1 refers to the above Chemical Formula 1-7.

[0133] In this specification, the above Chemical Formula 1 refers to the above Chemical Formula 1-8.

[0134] In this specification, the above Chemical Formula 1 refers to the above Chemical Formula 1-9.

[0135] In this specification, the above Chemical Formula 1 refers to the above Chemical Formula 1-10.

[0136] In one embodiment of the present specification, R1 to R10 that are not bound to L1 of the above Chemical Formula 1-A and are not bound to L2 of Chemical Formula 1-B are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0137] In one embodiment of the present specification, R1 to R10 that are not bound to L1 of the above Chemical Formula 1-A and not bound to L2 of the Chemical Formula 1-B are the same as 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.

[0138] In one embodiment of the present specification, R1 to R10 that are not bound to L1 of the above Chemical Formula 1-A and not bound to L2 of the Chemical Formula 1-B are the same as 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.

[0139] In one embodiment of the present specification, R1 to R10 that are not bound to L1 of the above Chemical Formula 1-A and not bound to L2 of the Chemical Formula 1-B are the same as 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.

[0140] In one embodiment of the present specification, R1 to R10 that are not bound to L1 of the above Chemical Formula 1-A and not bound to L2 of the Chemical Formula 1-B are the same as 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.

[0141] In one embodiment of the present specification, R1 to R10 that are not bound to L1 of the above Chemical Formula 1-A and are not bound to L2 of the Chemical Formula 1-B are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl , substituted or unsubstituted triphenylene, substituted or unsubstituted furyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted naphthobenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted pyrimidinyl.

[0142] In one embodiment of the present specification, R1 to R10 that are not bound to L1 of the above Chemical Formula 1-A and not bound to L2 of Chemical Formula 1-B are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, or a deuterium-substituted or unsubstituted naphthyl group.

[0143] In one embodiment of the present specification, R1 to R10 that are not bound to L1 in Chemical Formula 1-A and not bound to L2 in Chemical Formula 1-B are the same as or different from each other and are each independently hydrogen or deuterium.

[0144] In one embodiment of the present specification, R1 to R10 that are not bonded to L1 in the above Chemical Formula 1-A and are not bonded to L2 in Chemical Formula 1-B are hydrogen.

[0145] In one embodiment of the present specification, R1 to R10 that are not bonded to L1 in Chemical Formula 1-A and not bonded to L2 in Chemical Formula 1-B are deuterium.

[0146] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0147] In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond; an arylene group which is substituted or unsubstituted by 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 which is substituted or unsubstituted by 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.

[0148] In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond; an arylene group which is substituted or unsubstituted by 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 which is substituted or unsubstituted by 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.

[0149] In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond; an arylene group which is substituted or unsubstituted by 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 which is substituted or unsubstituted by 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.

[0150] In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond; an arylene group which is substituted or unsubstituted by 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 which is substituted or unsubstituted by 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.

[0151] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

[0152] In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond; a naphthylene group which is substituted or unsubstituted by 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 which is substituted or unsubstituted by 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.

[0153] In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond; a naphthylene group which is substituted or unsubstituted by 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 which is substituted or unsubstituted by 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.

[0154] In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond; a naphthylene group which is substituted or unsubstituted by 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 which is substituted or unsubstituted by 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.

[0155] In one embodiment of the present specification, L1 and L2 are the same as or different from each other and are each independently a direct bond; a naphthylene group which is substituted or unsubstituted by 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 which is substituted or unsubstituted by 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.

[0156] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, 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.

[0157] In one embodiment of the present specification, R101 to R110 are the same as 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 R101 to R108 must be bound to L1.

[0158] In one embodiment of the present specification, R101 to R110 are the same as 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 R101 to R108 must be bound to L1.

[0159] In one embodiment of the present specification, R101 to R110 are the same as 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 R101 to R108 must be bound to L1.

[0160] In one embodiment of the present specification, R101 to R110 are the same as 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 R101 to R108 must be bound to L1.

[0161] In one embodiment of the present specification, R101 to R110 are the same as or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted tert-phenylene, substituted or unsubstituted quaternaryl ... R101 to R108 are substituted or unsubstituted furyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted naphthobenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted pyrimidinyl, and one of R101 to R108 must be bound to L1.

[0162] The above X is O or S.

[0163] The above X is O.

[0164] The above X is S.

[0165] In one embodiment of the present specification, any one of R201 to R206 is bound to L2, and the rest are the same or different and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0166] However, when R203 or R205 is bonded to L2, four or more of R201 to R206 not bonded to L2 are hydrogen atoms, or either L1 or L2 is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.

[0167] In one embodiment of the present specification, any one of R201 to R206 is bonded to L2, and the rest are the same or different and are 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.

[0168] However, when R203 or R205 is bonded to L2, four or more of R201 to R206 not bonded to L2 are hydrogen atoms, or either L1 or L2 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0169] In one embodiment of the present specification, any one of R201 to R206 is bonded to L2, and the rest are the same or different and are 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.

[0170] However, when R203 or R205 is bonded to L2, four or more of R201 to R206 not bonded to L2 are hydrogen atoms, or either L1 or L2 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0171] In one embodiment of the present specification, any one of R201 to R206 is bonded to L2, and the rest are the same or different and are 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.

[0172] However, when R203 or R205 is bonded to L2, four or more of R201 to R206 not bonded to L2 are hydrogen atoms, or either L1 or L2 is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0173] In one embodiment of the present specification, any one of R201 to R206 is bonded to L2, and the rest are the same or different and are 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.

[0174] However, when R203 or R205 is bonded to L2, four or more of R201 to R206 not bonded to L2 are hydrogen atoms, or either L1 or L2 is a substituted or unsubstituted arylene group having 6 to 10 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 10 carbon atoms.

[0175] In one embodiment of the present specification, any one of R201 to R206 is bonded to L2, and the rest are the same or different and are independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted naphthobenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted pyrimidinyl.

[0176] However, when R203 or R205 is bonded to L2, four or more of R201 to R206 not bonded to L2 are hydrogen, or any one of L1 and L2 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted terphenylene group.

[0177] In one embodiment of the present specification, the above n is an integer of 1 to 4.

[0178] In one embodiment of the present specification, the above n is 4.

[0179] In one embodiment of the present specification, the above n is 3.

[0180] In one embodiment of the present specification, the above n is 2.

[0181] In one embodiment of the present specification, the above n is 1.

[0182] In one embodiment of the present specification, the above m is an integer of 1 to 4.

[0183] In one embodiment of the present specification, the above m is 4.

[0184] In one embodiment of the present specification, the above m is 3.

[0185] In one embodiment of the present specification, the above m is 2.

[0186] In one embodiment of the present specification, the above m is 1.

[0187] According to one embodiment of the present specification, R9 of the above Chemical Formula 1 is combined with L1 of the above Chemical Formula 1-A, and R10 of the above Chemical Formula 1 is combined with L2 of the above Chemical Formula 1-B.

[0188] In the above Chemical Formula 1, R1 to R8 are all deuterium.

[0189] According to one embodiment of the present specification, R201 to R206 not bonded to L2 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0190] According to one embodiment of the present specification, R201 to R206 not bonded to L2 are the same as or different from each other and are independently hydrogen.

[0191] According to one embodiment of the present specification, R201 to R206 not bound to L2 are the same as or different from each other and are independently deuterated.

[0192] According to one embodiment of the present specification, the deuterium substitution rate in the above Chemical Formula 1 is 15% or more.

[0193] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 30% or more.

[0194] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 40% or higher.

[0195] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 50% or more.

[0196] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 60% or higher.

[0197] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 70% or higher.

[0198] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 80% or more.

[0199] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 90% or higher.

[0200] According to one embodiment of the present specification, the deuterium substitution rate in the above Chemical Formula 1 is 100%.

[0201] According to one embodiment of the present specification, when the above chemical formula 1 contains deuterium, it has the following effects. Specifically, the physicochemical properties such as the bond length of the chemical bond related to deuterium are different from those of hydrogen. Compared with the C-H bond, the stretching amplitude of the CD bond is smaller, so the van der Waals radius of deuterium is smaller than that of hydrogen. Generally, it can be shown that the CD bond is shorter and stronger than the C-H bond. Therefore, when the hydrogen at the substitutable position of the above chemical formula 1 is replaced by deuterium, the energy of the ground state is reduced, the bond length between deuterium and carbon becomes shorter, and thus the molecular hardcore volume is reduced, so the electrical polarizability can be reduced, the intermolecular interaction is weakened, and the film volume can be increased. In addition, such characteristics can produce the effect of reducing the crystallinity of the film, that is, the amorphous state, which can usually effectively improve the lifespan and driving characteristics of the organic light-emitting device, and the heat resistance can be further improved compared with the existing organic light-emitting device.

[0202] In the present specification, “containing deuterium”, “deuterated” or “deuterated” means that hydrogen at a substitutable position of the compound is substituted with deuterium.

[0203] In this specification, “overdeuterated” refers to a compound or group in which all hydrogen atoms in the molecule are replaced by deuterium, and has the same meaning as “100% deuterated”.

[0204] As used herein, "X% deuterated," "degree of deuteration X%," or "deuterium substitution rate X%" means that X% of the hydrogen atoms at substitutable positions in the structure are substituted with deuterium. For example, when the structure is dibenzofuran, "25% deuterated" dibenzofuran, "degree of deuteration 25%" of dibenzofuran, or "deuterium substitution rate 25%" of dibenzofuran means that two of the eight hydrogen atoms at substitutable positions in the dibenzofuran are substituted with deuterium.

[0205] In this specification, the "degree of deuteration" or "deuterium substitution rate" can be determined by nuclear magnetic resonance spectroscopy ( 1The identity of the substance can be confirmed by a known method such as HNMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry) or GC / MS (Gas Chromatography / Mass Spectrometry).

[0206] Specifically, by nuclear magnetic resonance spectroscopy ( 1 When analyzing the "degree of deuteration" or "deuterium substitution rate" by H NMR, DMF (dimethylformamide) can be added as an internal standard. 1 The integration ratio in H NMR is used to calculate the degree of deuteration or deuterium substitution rate from the integrated amount of the total peak.

[0207] In addition, when analyzing the "degree of deuteration" or "deuterium substitution rate" by TLC / MS (thin layer chromatography / mass spectrometry), the substitution rate can be calculated based on the maximum value (median value) of the distribution formed by the molecular weight at the end of the reaction. For example, when analyzing the degree of deuteration of the following compound A, the molecular weight of the following starting material is 506. When it is indicated that Figure 3 When the maximum molecular weight (median value) of the following compound A in the MS chart is 527, 21 of the 26 hydrogen atoms at the substitutable positions of the following starting material are substituted with deuterium, and therefore it can be calculated that about 81% of the hydrogen atoms are deuterated.

[0208]

[0209]

[0210] In this specification, D represents deuterium.

[0211] In one embodiment of the present specification, the above Chemical Formula 1 is an organic compound of any one of the following compounds.

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219] The organic compound of Chemical Formula 1 according to one embodiment of the present specification can be prepared as described in the following preparation examples to produce a core structure. Substituents can be bonded by methods known in the art, and the type, position, or number of substituents can be varied according to techniques known in the art.

[0220] In this specification, compounds with various energy band gaps can be synthesized by introducing various substituents into the core structure of the organic compound of the above Chemical Formula 1. In addition, in this specification, the HOMO and LUMO energy levels of the compound can also be adjusted by introducing various substituents into the core structure of the structure described above.

[0221] In addition, the present specification provides an organic light-emitting device including the above-mentioned organic compound.

[0222] The organic light-emitting device according to the present specification is characterized by comprising: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers contains the organic compound represented by the above-mentioned Chemical Formula 1.

[0223] The organic layer of the organic light-emitting device of the present specification may be formed of a single layer structure or a multilayer structure comprising two or more organic layers stacked together. For example, the organic light-emitting device of the present invention may have a structure including one or more of a hole transport layer, a hole injection layer, an electron modulation layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole modulation layer, and an electron transport and injection layer as the organic layer. However, the structure of the organic light-emitting device of the present specification is not limited to this structure and may include a fewer or greater number of organic layers.

[0224] In the organic light-emitting device of the present specification, the organic light-emitting device includes a light-emitting layer, and the light-emitting layer may contain the organic compound.

[0225] For example, the organic compound of the above Chemical Formula 1 may be included as a host of the light emitting layer.

[0226] According to one embodiment of the present specification, the light-emitting layer includes a dopant, and the dopant includes a fluorescent dopant.

[0227] According to one embodiment of the present specification, the fluorescent dopant is a pyrene-based compound or a non-pyrene-based compound.

[0228] According to one embodiment of the present specification, the non-pyrene-based compound includes a boron-based compound.

[0229] According to one embodiment of the present specification, the light-emitting layer further includes one or more hosts different from the compound of Chemical Formula 1.

[0230] In one embodiment of the present specification, a host different from the compound of the above Chemical Formula 1 includes a compound of the following Chemical Formula H-1.

[0231] In one embodiment of the present specification, the light-emitting layer of the organic light-emitting device includes the organic compound as a host and further includes a host represented by the following chemical formula H-1, which is different from the organic compound.

[0232] [Chemical formula H-1]

[0233]

[0234] In the above chemical formula H-1,

[0235] L301 and L302 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group,

[0236] Ar301 and Ar302 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0237] 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,

[0238] r301 is an integer of 1 to 7. When r301 is 2 or more, two or more R301s are the same as or different from each other.

[0239] According to one embodiment of the present specification, the chemical formula H-1 is represented by the following compound.

[0240]

[0241] As for the host different from the compound of the above Chemical Formula 1, any host different from the above Chemical Formula 1 and an anthracene-based host used in the technical field may be used without limitation, and is not limited thereto.

[0242] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant.

[0243] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the host includes the compound represented by Chemical Formula 1.

[0244] According to one embodiment of the present specification, the dopant is a blue dopant.

[0245] According to one embodiment of the present specification, the organic light-emitting device is a blue organic light-emitting device.

[0246] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes the compound represented by Chemical Formula 1, and the dopant includes one or more selected from pyrene-based compounds and non-pyrene-based compounds.

[0247] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and a weight ratio of the host to the dopant in the light-emitting layer is 8:2 to 99:1.

[0248] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and a weight ratio of the host to the dopant in the light-emitting layer is 8:2 to 95:5.

[0249] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and a weight ratio of the host to the dopant in the light-emitting layer is 90:10 to 99:1.

[0250] According to another embodiment of the present specification, a cover layer is further provided on a surface opposite to a surface of at least one of the first electrode and the second electrode that faces the organic layer.

[0251] The above-mentioned covering layer is formed to prevent a large amount of light from being lost due to total reflection of light in the organic light-emitting device. The covering layer has the ability to fully 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 reflection.

[0252] According to another embodiment of the present specification, the cover layer may be provided on a surface of the first electrode opposite to a surface facing the organic layer and on a surface of the second electrode opposite to a surface facing the organic layer.

[0253] According to another embodiment of the present specification, the cover layer may be provided on a surface of the first electrode opposite to a surface facing the organic layer.

[0254] According to another embodiment of the present specification, the cover layer may be provided on a surface of the second electrode opposite to a surface facing the organic layer.

[0255] According to one embodiment of the present specification, the organic light-emitting device further includes one or more layers selected from a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron regulation layer, and a hole regulation layer.

[0256] According to one embodiment of the present specification, the organic light-emitting device includes a first electrode; a second electrode; a light-emitting layer arranged between the first electrode and the second electrode; and two or more organic layers arranged between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0257] According to one embodiment of the present specification, the two or more organic layers between the above-mentioned light-emitting layer and the above-mentioned first electrode, or between the above-mentioned light-emitting layer and the above-mentioned second electrode can be selected from two or more of the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a hole injection and transport layer, a hole regulation layer, an electron regulation layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer.

[0258] 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 contain the same or different substances.

[0259] According to one embodiment of the present specification, the first electrode is an anode or a cathode.

[0260] According to one embodiment of the present specification, the second electrode is a cathode or an anode.

[0261] According to one embodiment of the present specification, the organic light-emitting device may be a normal type organic light-emitting device having a structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0262] 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.

[0263] For example, the structure of the organic light-emitting device according to one embodiment of the present specification is shown in FIG. Figure 1 and 2 . The above Figure 1 and 2 An organic light emitting device is exemplified, but is not limited thereto.

[0264] Figure 1 exemplifies 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 above-mentioned compound is contained in the light-emitting layer.

[0265] Figure 2exemplifies 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 regulation layer 7, a light-emitting layer 4, an electron regulation 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 above-mentioned compound is contained in the light-emitting layer.

[0266] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that the light-emitting layer includes the compound represented by Chemical Formula 1.

[0267] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0268] 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. In this case, the device can be manufactured as follows: a metal, a conductive metal oxide, or an alloy thereof is deposited on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode. An organic layer comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is then formed on the anode. A cathode material is then deposited on the organic layer. Alternatively, an 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.

[0269] Furthermore, when manufacturing an organic light-emitting device, the compound represented by Chemical Formula 1 can be applied not only by vacuum evaporation but also by solution coating to form an organic layer. Solution coating methods include, but are not limited to, spin coating, dip coating, doctor blade coating, inkjet printing, screen printing, spraying, and roller coating.

[0270] In addition to these methods, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a second electrode material, an organic layer, and a first electrode material on a substrate. However, the manufacturing method is not limited to this.

[0271] The first electrode material is typically one with a high work function to facilitate hole injection into the organic layer. Examples include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0272] The second electrode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Examples include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0273] The light-emitting layer may include a host material and a dopant material. When another light-emitting layer is included in addition to the light-emitting layer including the compound of Chemical Formula 1 according to one embodiment of the present specification, the host material includes aromatic fused ring derivatives and / or aromatic non-fused ring derivatives or heterocyclic compounds. Specifically, as aromatic fused ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited thereto.

[0274] According to one embodiment of the present specification, the host includes a compound represented by the above Chemical Formula 2, but is not limited thereto.

[0275] As the dopant material, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, Diindenopyrene, etc. Furthermore, styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups. Specific examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetramine. Furthermore, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0276] According to one embodiment of the present specification, the dopant material includes a compound represented by the following chemical formula D-1 or D-2, but is not limited thereto.

[0277] [Chemical Formula D-1]

[0278]

[0279] In the above chemical formula D-1,

[0280] L101 and L102 are the same or different from each other, and are each independently a directly bonded, substituted or unsubstituted arylene group,

[0281] Ar101 to Ar104 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0282] [Chemical Formula D-2]

[0283]

[0284] In the above chemical formula D-2,

[0285] T1 to T5 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted aryl group,

[0286] t3 and t4 are each an integer from 1 to 4,

[0287] t5 is an integer from 1 to 3,

[0288] When the above t3 is 2 or more, the above two or more T3 are the same or different from each other.

[0289] When the above t4 is 2 or more, the above two or more T4 are the same or different from each other.

[0290] When the above-mentioned t5 is 2 or more, the above-mentioned two or more T5s may be the same as or different from each other.

[0291] According to one embodiment of the present specification, L101 and L102 are directly bonded.

[0292] According to one embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0293] According to one embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0294] According to one embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are each independently a phenyl group substituted with a methyl group, or a dibenzofuranyl group.

[0295] According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compound.

[0296]

[0297] According to one embodiment of the present specification, the above-mentioned T1 to T5 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted linear or branched 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.

[0298] According to one embodiment of the present specification, the above-mentioned T1 to T5 are the same as or different from each other and are each independently hydrogen, a linear or branched 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 which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

[0299] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and are independently hydrogen, methyl, tert-butyl, diphenylamino, or phenyl which may be substituted or unsubstituted with a methyl or tert-butyl group.

[0300] According to one embodiment of the present specification, the chemical formula D-2 is represented by the following compound.

[0301]

[0302] The hole injection layer is a layer that receives holes from the electrode. The hole injection material is preferably a material that has the ability to transport holes, has the effect of receiving holes from the anode, and has an excellent hole injection effect for the light-emitting layer or the light-emitting material. In addition, it is preferably a material that has an excellent ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. In addition, it is preferably a material with excellent thin film forming ability. In addition, it is preferred that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organics; hexanitrile hexaazatriphenylene-based organics; quinacridone-based organics; perylene-based organics; anthraquinone, polyaniline and polythiophene-based conductive polymers, etc., but are not limited to these.

[0303] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-1, but is not limited thereto.

[0304] [Chemical formula HI-1]

[0305]

[0306] In the above chemical formula HI-1,

[0307] At least one of X'1 to X'6 is N, and the others are CH,

[0308] R309 to R314 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or combine with adjacent groups to form a substituted or unsubstituted ring.

[0309] According to one embodiment of the present specification, X'1 to X'6 are N.

[0310] According to one embodiment of the present specification, R309 to R314 are cyano groups.

[0311] According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound.

[0312]

[0313] The hole transport layer receives holes from the hole injection layer and transports them to the light-emitting layer. A hole transport material is a substance capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer, preferably a substance with high hole mobility. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions.

[0314] According to one embodiment of the present specification, the hole transport layer or the hole regulation layer includes a compound of the following chemical formula HT-1, but is not limited thereto.

[0315] [Chemical formula HT-1]

[0316]

[0317] In the above chemical formula HT-1,

[0318] R315 to R317 are the same as or different from each other, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0319] r315 is an integer from 1 to 5. When the above r315 is 2 or more, the two or more R315 are the same or different from each other.

[0320] r316 is an integer of 1 to 5. When r316 is 2 or more, two or more R316 are the same or different from each other.

[0321] According to one embodiment of the present specification, R317 is any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0322] According to one embodiment of the present specification, R317 is any one selected from the group consisting of carbazolyl, phenyl, biphenyl, fluorenyl, and combinations thereof.

[0323] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are independently a substituted or unsubstituted aryl group, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0324] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are independently phenyl or phenanthrenyl, or are combined with adjacent groups to form an indene substituted with a methyl group.

[0325] According to one embodiment of the present specification, the chemical formula HT-1 is represented by any one of the following compounds.

[0326]

[0327] The hole regulation layer regulates the smooth injection of holes from the hole transport layer into the light-emitting layer, preventing electrons injected from the electron injection layer from passing through the light-emitting layer into the hole injection layer, thereby improving the device's lifespan and efficiency. Known materials can be used without limitation, and the layer 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.

[0328] The material of the electron adjustment layer can be applied to the material exemplified by the chemical formula HT-I, but is not limited thereto.

[0329] The electron regulating layer is a layer for regulating the smooth injection of electrons transferred from the electron transporting layer into the light emitting layer, and any known material can be used without limitation.

[0330] According to one embodiment of the present specification, the electron adjustment layer includes a compound of the following chemical formula EG-1, but is not limited thereto.

[0331] [Chemical formula EG-1]

[0332]

[0333] In the above chemical formula EG-1,

[0334] At least one of G1 to G18 is -L5-Ar5, and the rest are hydrogen, or G1 and G18 are linked through -L51- to form a substituted or unsubstituted ring,

[0335] L5 is a direct bond, or a substituted or unsubstituted arylene group,

[0336] Ar5 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0337] L51 is O or S.

[0338] According to one embodiment of the present specification, the above L51 is O.

[0339] According to one embodiment of the present specification, the above-mentioned L51 is S.

[0340] According to one embodiment of the present specification, G1 and G18 are linked via -L51- to form a substituted or unsubstituted heterocyclic ring.

[0341] According to one embodiment of the present specification, G1 and G18 are linked through -L51- to form a substituted or unsubstituted xanthene ring or a substituted or unsubstituted thioxanthene ring.

[0342] According to one embodiment of the present specification, G1 and G18 are linked via -O- to form a substituted or unsubstituted xanthene ring.

[0343] According to one embodiment of the present specification, G1 and G18 are linked via -S- to form a substituted or unsubstituted thioxanthene ring.

[0344] According to one embodiment of the present specification, G1 and G18 are linked via -O- to form a xanthene ring.

[0345] According to one embodiment of the present specification, G1 and G18 are linked via -S- to form a thioxanthene ring.

[0346] According to one embodiment of the present specification, L5 is a directly bonded, or substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0347] According to one embodiment of the present specification, L5 is a directly bonded, or substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0348] 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.

[0349] 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.

[0350] According to one embodiment of the present specification, the above-mentioned L5 is a direct bond or a phenylene group.

[0351] According to one embodiment of the present specification, Ar5 is a substituted or unsubstituted triazine group.

[0352] According to one embodiment of the present specification, Ar5 is a triazine group which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0353] According to one embodiment of the present specification, Ar5 is a triazine group substituted with a phenyl group.

[0354] According to one embodiment of the present specification, the EG-1 is represented by the following compound.

[0355]

[0356] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, preferably a material with a large mobility for electrons. As a specific example, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to these. The electron transport layer can be used together with any desired cathode material as used in the prior art. In particular, a suitable cathode material is a common material having a low work function and accompanied by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, etc., in each case accompanied by an aluminum layer or a silver layer.

[0357] According to one embodiment of the present specification, the electron transport layer includes a compound of the following chemical formula ET-1, but is not limited thereto.

[0358] [Chemical formula ET-1]

[0359]

[0360] In the above chemical formula ET-1,

[0361] At least one of Z11 to Z13 is N, and the rest are CH,

[0362] L601 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0363] Ar601 and Ar602 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0364] l601 is an integer from 1 to 5. When the above-mentioned l601 is 2 or more, the above-mentioned two or more L601 are the same as or different from each other.

[0365] According to one embodiment of the present specification, L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0366] According to one embodiment of the present specification, L601 is a phenylene group, a biphenylene group, or a naphthylene group.

[0367] According to one embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0368] According to one embodiment of the present specification, Ar601 and Ar602 are phenyl groups.

[0369] According to one embodiment of the present specification, the chemical formula ET-1 is represented by the following compound.

[0370]

[0371] The electron injection layer is a layer that receives electrons from the electrode. As the electron injection material, preferably, the following materials are used: materials that have excellent ability to transport electrons, have the effect of receiving electrons from the second electrode, and have excellent electron injection effect on the light-emitting layer or the light-emitting material. In addition, materials that prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer and have excellent thin film forming ability are preferred. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0372] Examples of the metal coordination compounds include, but are not limited to, 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)gallium chloride, bis(2-methyl-8-quinolinato)(o-cresol)gallium, bis(2-methyl-8-quinolinato)(1-naphthol)aluminum, and bis(2-methyl-8-quinolinato)(2-naphthol)gallium.

[0373] According to one embodiment of the present specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. The electron injection and transport layer can use the materials exemplified in the electron transport layer and electron injection layer, but is not limited thereto.

[0374] According to one embodiment of the present specification, the electron injection and transport layer may further include a metal coordination compound. The metal coordination compound is as described above.

[0375] The electron regulation layer prevents electrons injected from the electron injection layer from passing through the light-emitting layer and into the hole injection layer, thereby improving the device's lifespan and efficiency. Known materials can be used without limitation, and the layer 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.

[0376] The material of the electron adjustment layer can be applied to the material exemplified by the chemical formula HT-I, but is not limited thereto.

[0377] The hole regulating layer is a layer that prevents holes from reaching the cathode and can usually be formed using the same conditions as the electron injection layer. Examples include, but are not limited to, diazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0378] The above-mentioned covering layer is formed to prevent a large amount of light from being lost due to total reflection of light in the organic light-emitting device. The covering layer has the ability to fully protect the lower cathode and light-emitting layer from external moisture penetration or contamination. It has a high refractive index and can prevent light loss due to total reflection. Existing materials can be used without restrictions.

[0379] According to one embodiment of the present specification, the coating layer includes a compound represented by the following chemical formula CP-1, but the present invention is not limited thereto.

[0380] [Chemical formula CP-1]

[0381]

[0382] In the above chemical formula CP-1,

[0383] L501 and L502 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0384] R501 and Ar501 to Ar504 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, or adjacent groups are combined to form a substituted or unsubstituted ring.

[0385] According to one embodiment of the present specification, L501 and L502 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0386] According to one embodiment of the present specification, L501 and L502 are phenylene groups.

[0387] According to one embodiment of the present specification, R501 and Ar501 to Ar504 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0388] According to one embodiment of the present specification, R501 and Ar501 to Ar504 are phenyl groups, or are combined with adjacent groups to form a carbazole group substituted or unsubstituted with a phenyl group.

[0389] According to one embodiment of the present specification, Ar501 and L501 are bonded to form a carbazole substituted with a phenyl group.

[0390] According to one embodiment of the present specification, Ar503 and L503 are bonded to form a carbazole substituted with a phenyl group.

[0391] According to one embodiment of the present specification, the chemical formula CP-1 is represented by the following compound.

[0392]

[0393] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0394] The organic light-emitting device according to the present specification can be included in various electronic devices and used. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0395] Below, to specifically illustrate this specification, examples will be given for detailed description. However, the examples of this specification can be modified into various different forms, and the scope of this application is not to be construed as being limited to the examples detailed below. The examples of this application are provided to more fully illustrate this specification to those skilled in the art.

[0396] Preparation Example 1 (Synthesis of Chemical Formula 1)

[0397] 1) Synthesis of Chemical Formula A1

[0398]

[0399] SM1 (A0, 1 equivalent) and SM2 (1.1 equivalents) were added to tetrahydrofuran (THF) (excess), followed by the addition of a 2M aqueous potassium carbonate solution (30 volume ratio relative to THF), and then tetrakis(triphenylphosphine)palladium (2 mol%), followed by heating and stirring at 85°C for 10 hours. The temperature was lowered to room temperature to terminate the reaction, and the aqueous potassium carbonate solution was removed. The layers were separated, and column chromatography was performed using hexane and ethyl acetate to produce the above-mentioned chemical formula A1 (A1-1 to A1-5).

[0400] In the synthesis method of the above-mentioned chemical formula A1, except that SM1 and SM2 were changed to the substances in the following Table 1, A1-1 to A1-5 in Table 1 were synthesized by the same method.

[0401]

Table 1

[0402]

[0403] 2) Synthesis of Chemical Formulas A2 and B2

[0404]

[0405] SM1 (one of A1 or BO, 1 equivalent) and SM2 (one of P1 or P2, 1.1 equivalents) were added to tetrahydrofuran (THF) (excess amount), followed by the addition of a 2M aqueous potassium carbonate solution (30 volume ratio relative to THF), and then tetrakis(triphenylphosphine)palladium (2 mol%), followed by heating and stirring at 85°C for 10 hours. The temperature was lowered to room temperature to terminate the reaction, and the aqueous potassium carbonate solution was removed. The layers were separated, and column chromatography was performed using hexane and ethyl acetate to produce the above-mentioned chemical formulas A2 and B2 (A2-1 to A2-3 and B2-1 to B2-5), respectively.

[0406] In the synthesis methods of the above chemical formulas A2 and B2, except that SM1 and SM2 were changed to the substances in Tables 2 and 3 below, A2-1 to A2-3 in Table 2 and B2-1 to B2-5 in Table 3 were synthesized by the same method.

[0407]

Table 2

[0408]

[0409]

Table 3

[0410]

[0411] 3) Synthesis of Chemical Formulas A3 and B3

[0412]

[0413] SM1 (one of A1 and A2 or B0 and B2, 1 equivalent) and SM2 (1.3 equivalents) were added to 1,4-dimethoxy- Potassium acetate (3 equivalents) was added to 12 times the mass ratio of SM1, stirred and refluxed. Bis(diphenylphosphino)ferrocenepalladium dichloride (0.05 equivalents) was added to 1,4-dioxane. The mixture was stirred in oxane for 5 minutes and then added. After 2 hours, the reaction was confirmed to be complete and then cooled to room temperature. Ethanol and water were added, filtered, and purified by recrystallization from ethyl acetate and ethanol to produce the above-mentioned chemical formulas A3 and B3 (A3-1 to A3-8 and B3-1 to B3-22), respectively.

[0414] In the synthesis methods of the above chemical formulas A3 and B3, except that SM1 and SM2 were changed to the substances in Tables 4 and 5 below, A3-1 to A3-8 in Table 4 and B3-1 to B3-22 in Table 5 were synthesized by the same method.

[0415]

Table 4

[0416]

[0417]

[0418]

Table 5

[0419]

[0420]

[0421]

[0422]

[0423] The synthesis of the above chemical formula B3 was performed with reference to LGC KR 2023-0107466 A.

[0424] 4) Synthesis of Int 1.

[0425]

[0426] SM1 (one of A3, 1 equivalent) and SM2 (1 equivalent) were added to tetrahydrofuran (THF) (excess amount), followed by the addition of a 2M aqueous potassium carbonate solution (30 volume ratio relative to THF), and then tetrakis(triphenylphosphine)palladium (2 mol%), followed by heating and stirring at 85°C for 10 hours. The temperature was lowered to room temperature to terminate the reaction, and the aqueous potassium carbonate solution was removed, the layers were separated, and the product was recrystallized from chloroform and ethyl acetate to produce the above-mentioned compounds of the chemical formula int. (int 1-1. to int 1-14.).

[0427] In the synthesis method of the above chemical formula int 1., int 1-1. to int 1-14. in Table 6 were synthesized by the same method except that SM1 and SM2 were changed to the substances in Table 6 below.

[0428]

Table 6

[0429]

[0430]

[0431]

[0432] 5) Synthesis of Int 2.

[0433]

[0434] After dissolving SM1 (one of the compounds in int 1., 1 equivalent) in chloroform (excess), the temperature was lowered to 0°C. After stabilization, N-bromosuccinimide (1 equivalent) was dissolved in DMF (excess) and added dropwise. The reaction was then heated to room temperature and stirred for 1 hour. 1N HCl (excess) was added to terminate the reaction. After completion of the reaction, the layers were separated, the solvent was removed, and the residue was subjected to silica gel column chromatography (ethyl acetate / hexane 1:15) to produce chemical formula int 2. (int 2-1. to int 2-14.).

[0435] In the synthesis method of the above chemical formula int 2., int 2-1. to int 2-14. in Table 7 were synthesized by the same method except that SM1 and SM2 were changed to the substances in Table 7 below.

[0436]

Table 7

[0437]

[0438]

[0439]

[0440] 6) Synthesis of Chemical Formula 1

[0441] SM1 (one of int 2, 1 equivalent) and SM2 (1.1 equivalents) were added to tetrahydrofuran (THF) (excess amount), followed by the addition of a 2M aqueous potassium carbonate solution (30 volume ratio relative to THF), tetrakis(triphenylphosphine)palladium (2 mol%), and then heated and stirred at 85°C for 10 hours. The temperature was lowered to room temperature, and after completion of the reaction, the aqueous potassium carbonate solution was removed, the layers were separated, and column chromatography was performed using hexane and ethyl acetate to produce the above-mentioned Chemical Formula 1 (Compounds 1 to 25).

[0442] In the synthesis method of the above chemical formula int., compounds 1 to 25 in Table 8 were synthesized by the same method except that SM1 and SM2 were changed to the substances in Table 8 below.

[0443]

Table 8

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450] 7) Synthesis of Chemical Formula 1D

[0451] Add the reactant (1 equivalent) and trifluoromethanesulfonic acid (catalyst (cat.)) to C6D6 (10 to 50 times the mass ratio relative to the reactant) and stir at 70°C for 10 to 100 minutes. After the reaction is completed, add D2O (excessive), stir for 30 minutes, and then add trimethylamine (excessive) dropwise. Transfer the reaction solution to a separatory funnel and extract with water and chloroform. S After drying with O4, the mixture was heated with toluene for recrystallization to obtain the products shown in Table 9 below (Compounds 26 to 29).

[0452]

Table 9

[0453]

[0454] [The degree of deuterium substitution of each product varies depending on the reaction time. +) value determines the substitution rate]

[0455] <Example 1> Production of OLED

[0456] ITO / Ag / ITO as the anode The substrate to be deposited was cut into pieces of 50 mm x 50 mm x 0.5 mm, placed in distilled water containing a dispersant, and cleaned using ultrasound. The detergent used was a Fischer product, and the distilled water used was distilled water filtered twice using a Millipore filter. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. Following the distilled water wash, ultrasonic cleaning was performed using isopropyl alcohol, acetone, and methanol, sequentially, and then dried.

[0457] On the anode prepared in this way, HI-1 was placed The hole injection layer is formed by thermal vacuum deposition with a thickness of 1000 nm. On the hole injection layer, HT1 as a hole transporting material is deposited with a thickness of 1000 nm. Vacuum evaporation is performed to form a hole transport layer. Then, EB1 Then, as the light-emitting layer, the host compound 1 synthesized in Preparation Example 1 and the dopant BD1 (2 wt%) were mixed with Then, HB1 is evaporated To form an electron adjustment layer, compound ET1 and Liq were mixed at a mass ratio of 5:5 to form a layer having a thickness of The electron transport layer. The thickness of magnesium and lithium fluoride (LiF) film is the electron injection layer <eil>Then, as cathode, magnesium and silver (1:4) were used to form After that, CP1 was evaporated Thus the device is completed. In the above process, the evaporation rate of the organic matter is maintained at

[0458]

[0459] [Comparative Examples 1 to 8 and Examples 1 to 33]

[0460] In Comparative Examples 1 to 8 and Examples 1 to 33, devices were manufactured by the same method as in Example 1, except that the substances listed in Table 10 below were used as materials for the light-emitting layer.

[0461] For the devices manufactured in Comparative Examples 1 to 8 and Examples 1 to 33, the 2 The driving voltage, luminous efficiency, and time to 95% of the initial luminance (LT95) were measured at a current density of 1.5 Å. The results are shown in Table 10 below.

[0462]

[0463]

Table 10

[0464]

[0465]

[0466] The results in [Table 10] above are for the case where the device structure has a light-emitting layer formed therein, the host of the light-emitting layer is a single host, and the compound claimed in the present application constitutes the host of the light-emitting layer.

[0467] Comparative Example 1 is a case where the carbon 3 of phenanthrene is bonded to the 10th position of anthracene, the carbon 2 of unsubstituted benzofuran is bonded to the 9th position of anthracene, and deuterium is introduced into the anthracene and unsubstituted benzofuran. The difference is that the carbon 2 of benzofuran is bonded to the 9th position of anthracene with an additional substituent. It can be confirmed that Examples 2, 6, and 7 have structural stabilization and carrier injection and migration speeds different from those of the comparative examples by introducing additional substituents into benzofuran, and in this device structure, they exhibit excellent performance, especially in terms of efficiency.

[0468] In addition, Examples 14 and 15 exhibited superior device characteristics compared to Comparative Examples 1 and 2 by further introducing substituents into the phenanthrene core under the above-mentioned conditions.

[0469] It can be seen that the introduction of connecting groups in Examples 22 to 25 can adjust the electrical characteristics, while maintaining the advantages of the corresponding structures and improving the lifespan.

[0470] In addition, Examples 26 to 29 show an average lifetime improvement of 10 to 15% through further deuterium substitution. Although there is a disadvantage in terms of cost, it shows that the lifetime can be further improved. Examples 30 to 33 are changes in dopants (pyrene dopant -> boron dopant). While maintaining the change in dopant characteristics, the device trend is maintained, so when various dopants are introduced, the consistency of the device can be demonstrated.

[0471] <Example 34> Production of OLED

[0472] ITO / Ag / ITO as the anode The deposited substrate was cut into pieces of 50 mm x 50 mm x 0.5 mm, placed in distilled water containing a dispersant, and cleaned using ultrasonic waves. The detergent used was a product from Fisher Scientific, and the distilled water used was twice filtered through a Millipore filter. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. Following the distilled water wash, ultrasonic cleaning was performed using isopropyl alcohol, acetone, and methanol, in that order, and then dried.

[0473] On the anode prepared in this way, HI-1 was placed The hole injection layer is formed by thermal vacuum deposition with a thickness of 1000 nm. On the hole injection layer, HT1 as a hole transporting material is deposited with a thickness of 1000 nm. Vacuum evaporation is performed to form a hole transport layer. Then, EB1 Then, as the light-emitting layer, the host compound 2 synthesized in Preparation Example 1 was mixed with BH13 and a dopant BD1 (2 wt%). Then, HB1 was evaporated to form a light-emitting layer. To form an electron adjustment layer, compound ET1 and Liq were mixed at a mass ratio of 5:5 to form a layer having a thickness of The electron transport layer. The thickness of magnesium and lithium fluoride (LiF) film is the electron injection layer <eil>Then, as cathode, magnesium and silver (1:4) were used to form After that, CP1 was evaporated During the above process, the evaporation rate of organic matter is maintained at

[0474]

[0475] [Comparative Examples 9 to 14 and Examples 34 to 38]

[0476] In Comparative Examples 9 to 14 and Examples 34 to 38, devices were manufactured by the same method as in Example 27, except that the substances listed in Table 2 below were used as materials for the light-emitting layer.

[0477] However, as shown in Table 11, the host of the light-emitting layer is an embodiment in which two hosts are co-evaporated using different evaporation sources during device fabrication to form the light-emitting layer.

[0478] The devices manufactured in Comparative Examples 9 to 14 and Examples 34 to 38 were subjected to an electric current of 20 mA / cm 2 The driving voltage, luminous efficiency, and time to 95% of the initial luminance (LT95) were measured at a current density of 1.5 Å. The results are shown in Table 11 below.

[0479]

Table 11

[0480]

[0481]

[0482] The results in [Table 11] above are for the case where the host of the light-emitting layer is composed of a mixed host (a host obtained by mixing two types of anthracene).

[0483] Comparative Examples 9 to 12 illustrate mixed hosts formed from widely used aryl anthracene compounds BH13 and BH14 with the BH1, BH2, BH3, and BH4 structures of this application. Devices employing these combinations in their light-emitting layers exhibited partial improvements in voltage, efficiency, and lifetime. Comparative Examples 13 and 14 also exhibited similar trends, even when using boron-based blue dopants.

[0484] Examples 34 to 38 are the device results obtained by forming a mixed host with Compound 2, Compound 6, Compound 17, and Compound 19 among the example compounds claimed in the present application and the above-mentioned BH13 or BH14. It can be seen that compared with Comparative Examples 9 to 14, the compounds claimed in the present application having excellent properties have the same trend even under the mixed host conditions.< / eil> < / eil>

Claims

1. An organic compound of the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, One or more of R1 to R10 is combined with L1 of the chemical formula 1-A, One or more of the R1 to R10 not bonded to L1 of the Chemical Formula 1-A is bonded to L2 of the Chemical Formula 1-B, The R1 to R10 that are not bound to L1 of the Chemical Formula 1-A and are not bound to L2 of the Chemical Formula 1-B are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, n and m are each an integer from 1 to 4, Ar1 is the following chemical formula 1-C, [Chemical Formula 1-C] In the chemical formula 1-C, R101 to R110 are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, and one of said R101 to R108 must be bound to L1. Ar2 is the following chemical formula 1-D, [Chemical Formula 1-D] In the chemical formula 1-D, X is O or S, Any one of R201 to R206 is combined with L2, and the rest are the same as or different from each other and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, However, when R203 or R205 is bonded to L2, four or more of R201 to R206 not bonded to L2 are hydrogen atoms, or either L1 or L2 is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, * indicates the site of bonding with Chemical Formula 1.

2. The organic compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 1-1 to 1-4: In the chemical formulas 1-1 to 1-4, The definitions of L1, L2, Ar2, R101 to R110, n and m are the same as those in Chemical Formula 1. Each of R1 to R8 is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

3. The organic compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 1-5 to 1-10: In the chemical formulas 1-5 to 1-10, The definitions of L1, L2, Ar1, X, R1 to R8, R201 to R206, n and m are the same as those in Chemical Formula 1. R1 to R8 are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, In the chemical formulas 1-7 and 1-9, four or more of R201 to R206 are hydrogen atoms, or any one of L1 and L2 is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.

4. The organic compound according to claim 1, wherein R9 of the chemical formula 1 is combined with L1 of the chemical formula 1-A, and R10 of the chemical formula 1 is combined with L2 of the chemical formula 1-B. In the chemical formula 1, R1 to R8 are all deuterium.

5. The organic compound according to claim 1, wherein The R201 to R206 not bound to L2 are the same as or different from each other, and are each independently hydrogen or deuterium.

6. The organic compound according to claim 1, wherein The deuterium substitution rate of Chemical Formula 1 is greater than 15%.

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

8. An organic light-emitting device, wherein: include: 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 comprises the organic compound according to any one of claims 1 to 7.

9. The organic light emitting device according to claim 8, wherein: The organic layer includes a light-emitting layer, and the light-emitting layer contains the organic compound.

10. The organic light emitting device according to claim 9, wherein The light-emitting layer includes the organic compound as a host of the light-emitting layer.

11. The organic light emitting device according to claim 9, wherein The light-emitting layer includes the organic compound as a host and further includes a host different from the organic compound and represented by the following chemical formula H-1: [Chemical formula H-1] In the chemical formula H-1, L301 and L302 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group, Ar301 and Ar302 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, R301 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, r301 is an integer of 1 to 7. When r301 is 2 or more, two or more R301s are the same as or different from each other.

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

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