Organic compound and organic light-emitting device including same

Abstract

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

Description

Technical Field

[0001] This application claims priority to Korean Patent Application No. 10-2024-0061689, filed with the Korean Patent Office on May 10, 2024, the entire contents of which are disclosed in the document and are incorporated herein by reference.

[0002] This specification relates to organic compounds and organic light-emitting devices containing them. Background Technology

[0003] Organic light emission (OLED) typically refers to the phenomenon of converting electrical energy into light energy using organic materials. OLED devices generally have a structure comprising an anode and a cathode, with an organic layer between them. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multilayer structure composed of different materials; for example, it can consist of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, they form excitons. When these excitons re-enter the ground state, they emit light.

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

[0005] Existing technical documents

[0006] Patent documents

[0007] (Patent Document 1) Chinese Patent Publication No. 114621274 Summary of the Invention

[0008] Technical issues

[0009] This specification provides information on organic compounds and organic light-emitting devices containing them.

[0010] Solution to the problem

[0011] One embodiment of this specification provides an organic compound of the following chemical formula 1.

[0012]

[0013] In the above chemical formula 1,

[0014] One or more of R1 to R10 combine with L1 of the aforementioned chemical formula 1-A.

[0015] One or more of the above-mentioned R1 to R10 that are not bound to L1 of the above-mentioned chemical formula 1-A are bound to L2 of the above-mentioned chemical formula 1-B.

[0016] R1 to R10, which are not combined with L1 of Formula 1-A and not combined with L2 of Formula 1-B, may be 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.

[0017] L1 and L2 may be the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0018] n and m are each integers from 1 to 4.

[0019] Ar1 has the following chemical formula 1-C,

[0020]

[0021] In the above chemical formula 1-C,

[0022] R101 to R110 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. One of R101 to R108 must be combined with L1.

[0023] Ar2 has the following chemical formula 1-D.

[0024]

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

[0026] X is O or S.

[0027] R201 to R206 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. At least one adjacent pair of R201 to R206 must combine with each other to form more than one substituted or unsubstituted cycloalloy.

[0028] The aforementioned substituted or unsubstituted cycloalloy, or any one of R201 to R206 that does not form the aforementioned substituted or unsubstituted cycloalloy, is combined with L2.

[0029] * indicates the site where it combines with chemical formula 1.

[0030] In addition, one embodiment of this specification provides an organic light-emitting device, which includes: 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 contain the aforementioned organic compound.

[0031] Invention Effects

[0032] The organic compounds described in this specification can be used as materials for the organic layer of organic light-emitting devices.

[0033] Organic compounds according to at least one embodiment of this specification can achieve improved efficiency, lower driving voltage, and / or improved lifetime characteristics in organic light-emitting devices. Attached Figure Description

[0034] Figure 1 The diagram illustrates the structure of an organic light-emitting device in which a first electrode 2, a light-emitting layer 4, and a second electrode 3 are sequentially stacked on a substrate 1. The aforementioned compound is contained within the light-emitting layer.

[0035] Figure 2 The diagram illustrates the structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, a hole modulation layer 7, a light-emitting layer 4, an electron modulation 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 aforementioned compound is contained within the light-emitting layer.

[0036] Figure 3 MS plot of compound A.

[0037] Symbol Explanation

[0038] 1: Substrate

[0039] 2: First electrode

[0040] 3: Second electrode

[0041] 4: Emissive layer

[0042] 5: Hole injection layer

[0043] 6: Hole transport layer

[0044] 7: Hole regulation layer

[0045] 8: Electronic regulation layer

[0046] 9: Electron transport layer

[0047] 10: Electron Injection Layer

[0048] 11: Overlay Detailed Implementation

[0049] The following is a more detailed description of this instruction manual.

[0050] In this specification, when a part is indicated to "include / comprise" a certain element, unless otherwise stated, it means that other elements may be included, rather than excluding other elements.

[0051] In this specification, when it is stated that a component is "on" another component, it includes not only the case where one component is connected to another component, but also the case where there are other components between the two components.

[0052] In this specification, "dashed line (---)" indicates the position of a chemical formula or compound.

[0053] In this instruction manual, Indicates the position where it is combined with a chemical formula or compound.

[0054] In this specification, "energy level" refers to the magnitude of energy. Therefore, an energy level is interpreted as the absolute value of that energy. For example, a low or deep energy level refers to an absolute increase in energy from the vacuum level in the negative direction.

[0055] In this specification, HOMO (highest occupied molecular orbital) refers to the molecular orbital function (HOMO) where the electron is located in the highest energy region of the bonding region. LUMO (lowest unoccupied molecular orbital) refers to the molecular orbital function (LUMO) where the electron is located in the lowest energy region of the antibonding region. The HOMO energy level refers to the distance from the vacuum energy level to the HOMO. Similarly, the LUMO energy level refers to the distance from the vacuum energy level to the LUMO.

[0056] In this specification, band gap refers to the energy difference between the HOMO and LUMO levels, i.e., the HOMO-LUMO band gap.

[0057] In this specification, the HOMO level can be measured at atmospheric pressure using a photoelectron spectrometer (manufactured by Riken Keiki Co., Ltd.: AC3), and the LUMO level can be calculated using wavelength values ​​measured by photoluminescence (PL).

[0058] Examples of substituents in this specification are described below, but are not limited thereto.

[0059] The term "substitution" refers to the replacement of hydrogen atoms on carbon atoms in a compound with other substituents. There is no limitation on the position of substitution, as long as the hydrogen atom can be substituted, that is, the position where the substituent can be substituted. When more than two substituents are substituted, the two or more substituents can be the same or different from each other.

[0060] In this specification, the term "substituted or unsubstituted" refers to a substance selected from deuterium, halogen groups, cyano (-CN), nitro, hydroxyl, alkyl, cycloalkyl, alkoxy, phosphine oxide, aryloxy, and alkylthio groups. aryl thiols alkylsulfonyl arylsulfonyl The substituent may be one or more of the following: alkenyl, silyl, boryl, amino, aryl, or heterocyclic groups; or may be substituted by a substituent formed by linking two or more of the substituents exemplified above; or may not have any substituents. For example, "a substituent formed by linking two or more substituents" can be biphenyl. That is, biphenyl can be aryl, or it can be interpreted as a substituent formed by linking two phenyl groups.

[0061] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen groups, cyano, silyl, alkoxy, aryloxy, alkyl, aryl, and heterocyclic groups, or substituted by two or more substituents linked together from the substituents exemplified above, or not having any substituents.

[0062] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, alkyl, aryl, and heterocyclic groups, or substituted by a substituent formed by linking two or more substituents of the substituents exemplified above, or having no substituents.

[0063] In this specification, "two or more substituents linked" means that the hydrogen of any one substituent is linked to other substituents. For example, isopropyl can be linked to phenyl to form... Such substituents.

[0064] In this specification, the connection of three substituents includes not only a continuous connection of (substituent 1)-(substituent 2)-(substituent 3), but also a connection of (substituent 2) and (substituent 3) to (substituent 1). For example, two phenyl groups and an isopropyl group can be connected to form... Such substituents. The same definition applies to connections of four or more substituents.

[0065] Examples of the substituents mentioned above are given below, but are not limited thereto.

[0066] Examples of halogen groups in this specification include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0067] In this specification, silyl groups 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 silyl groups include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited to these.

[0068] In this specification, the boron group can be represented by the chemical formula -BYdYe, where Yd and Ye can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the boron group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but are not limited to these.

[0069] In this specification, the alkyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited to these.

[0070] In this specification, the above description of alkyl groups applies, except when aryl alkyl groups are substituted with aryl groups.

[0071] In this specification, the alkoxy group can be straight-chain, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably 1 to 20. Specifically, it can be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, etc., but is not limited to these.

[0072] The alkyl, alkoxy, and other substituents containing alkyl moiety described in this specification include both straight-chain and branched forms.

[0073] In this specification, the alkenyl group can be straight-chain 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-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, styryl, etc., but are not limited to these.

[0074] In this specification, the alkynyl group is a substituent containing a triple bond between carbon atoms, and can be straight-chain or branched. The number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkynyl group has 2 to 20 carbon atoms. According to another embodiment, the alkynyl group has 2 to 10 carbon atoms.

[0075] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group with 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 yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., are used, but are not limited to these.

[0076] In this specification, the amino group is -NH2, and the amino group may be substituted with alkyl, aryl, heterocyclic, alkenyl, cycloalkyl, or 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 another 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, anthracene amino, dibenzofuranylphenylamino, 9-methylanthraylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenyltolylamino, diphenylamino, etc., but are not limited to these.

[0077] In this specification, aryl is not particularly limited, but is preferably an aryl with 6 to 60 carbon atoms, and can be a monocyclic aryl or a polycyclic aryl. According to one embodiment, the aryl has 6 to 30 carbon atoms. According to another embodiment, the aryl has 6 to 20 carbon atoms. The aryl can be an aryl or a polycyclic aryl (aryl with two or more rings) composed of a monocyclic ring. An aryl composed of a monocyclic ring can refer to a phenyl group, or a group formed by two or more phenyl groups linked together. As the aryl composed of a monocyclic ring, it can be phenyl, biphenyl, terphenyl, tetraphenyl, etc., but is not limited to these. A polycyclic aryl can refer to a group formed by two or more monocyclic rings fused together, such as naphthyl or phenanthryl. As the polycyclic aryl, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, etc. It includes methyl, fluorene, triphenylene, etc., but is not limited to these.

[0078] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure.

[0079] When the aforementioned fluorene group is replaced, it can be used as follows: Isospirofluorene group; (9,9-dimethylfluorene) and Substituted fluorenyl groups such as (9,9-diphenylfluorenyl) are used. However, this is not a limitation.

[0080] In this specification, the aryl group in the aryl group can be described in the above description of the aryl group.

[0081] In this specification, a heterocyclic group is a cyclic 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 is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to another embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of heterocyclic groups include pyridyl, pyrroloyl, pyrimidinyl, quinolinyl, pyridazinyl, furanyl, thiopheneyl, imidazoyl, pyrazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocarbazoleyl, naphthobenzofuranyl, benzonaphthothiopheneyl, indenzocarbazoleyl, triazinyl, etc., but are not limited to these.

[0082] In this specification, heteroaryl refers to aromatic compounds; otherwise, the above description of heterocyclic groups applies.

[0083] In this specification, a heteroaryl group comprises one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may comprise one or more atoms selected from O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30. The heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene, furanyl, pyrrole, imidazolyl, and thiazolyl. azole group, Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazenopyrazinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthridine, phenanthroline, iso Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothiopyrrolyl, phen Thiol (phenoxathiine), phen Phenoxazine, phenothiazine, dihydroindocarbazolyl, spirofluorenylxanthinyl, and spirofluorenylthioxanthinyl are examples, but not limited to these.

[0084] In this specification, the term arylene can be used to describe aryl groups except that it is divalent.

[0085] In this specification, the terms "divalent heterocyclic group" can be used in the same way as those used for the heterocyclic groups described above, except that the group is divalent.

[0086] In this specification, the description of aryl groups with an n+1 valence is the same as that of the aryl groups described above, except that they have an n+1 valence.

[0087] In this specification, the description of the above-mentioned heterocyclic groups applies to heterocyclic groups except that they are n+1 valence.

[0088] In this specification, "ring" refers to a hydrocarbon ring or heterocycle in the context of a substituted or unsubstituted ring formed by the combination of adjacent groups with each other.

[0089] The aforementioned hydrocarbon ring can be aromatic, aliphatic, or a fused ring of aromatic and aliphatic compounds, and can be selected from the examples of the aforementioned cycloalkyl or aryl groups.

[0090] In this specification, the term "forming a ring by bonding with adjacent groups" means forming 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 fused ring thereof by bonding with adjacent groups. The aforementioned hydrocarbon ring refers to a ring composed only of carbon and hydrogen atoms. The aforementioned heterocycle refers to a ring containing one or more atoms selected from N, O, P, S, Si, and Se. In this specification, the aforementioned aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle can be monocyclic or polycyclic.

[0091] In this specification, aliphatic hydrocarbon rings refer to non-aromatic rings composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene, but are not limited to these.

[0092] In this specification, aromatic hydrocarbon rings refer to aromatic rings composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenatene, pyrene, and tetraphenylene. The aromatic hydrocarbon rings include, but are not limited to, pentane, fluorene, indene, acenaphthene, benzo[a]fluorene, spirofluorene, etc. In this specification, the aromatic hydrocarbon ring can be interpreted in the same way as the aryl group.

[0093] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, and 1,4-dioxane. Alkane (1,4-dioxane), pyrrolidine, piperidine, morpholine, oxepane Azahexacyclic octane Thioheterocyclic octane etc., but not limited to this.

[0094] 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, etc. azole, isotonic azole, thiazole, isothiazole, triazole Diazole, thiadiazole, dithiazole, tetraazole, pyran, thiaran, diazine Azine, thiazide, diazine Alkenes, triazines, tetraazines, isoquinoline, quinoline, quinones, quinazoline, quinoxaline, naphthidine, acridine, phenanthridine, diazanaphthalene, triazaindene, indole, indolezine, benzothiazole, benzo[] azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenazine It includes aziridines, indobenzocarbazole, indobenzocarbazole, etc., but is not limited to these.

[0095] In this specification, a fused ring refers to a ring structure in which two or more rings share the shape of two or more atoms. The aforementioned fused ring can be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a fused ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, but is not limited to these.

[0096] In this specification, an aromatic fused hydrocarbon cycloyl group refers to a ring formed by the fusion of two or more aromatic hydrocarbon rings. Examples of aromatic fused hydrocarbon cycloyl groups include naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, and triphenylene. alkyl, fluorene, triphenylene etc., but not limited to this.

[0097] In this specification, unless otherwise defined, all technical and scientific terms used have the same meaning as commonly understood by those skilled in the art. Methods and materials similar to or equivalent to those described herein may be used to implement or test embodiments of the invention, but suitable methods and materials are described later. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, this specification, including definitions, takes precedence unless a specific passage is mentioned. Furthermore, materials, methods, and embodiments are illustrative and not intended to be limiting.

[0098] The preferred embodiments of the present invention will now be described in detail. However, the embodiments of the present invention can be modified in various ways, and the scope of the present invention is not limited to the embodiments described below.

[0099] The organic light-emitting device of the present invention is characterized by including all compounds represented by chemical formula 1 and compounds represented by chemical formula 2. The organic light-emitting device of the present invention exhibits the effects of low voltage, high efficiency and / or long lifetime.

[0100] The organic compounds of the following chemical formula 1 will now be described in detail.

[0101]

[0102] In the above chemical formula 1,

[0103] One or more of R1 to R10 combine with L1 of the aforementioned chemical formula 1-A.

[0104] One or more of the above-mentioned R1 to R10 that are not bound to L1 of the above-mentioned chemical formula 1-A are bound to L2 of the above-mentioned chemical formula 1-B.

[0105] R1 to R10, which are not combined with L1 of Formula 1-A and not combined with L2 of Formula 1-B, may be 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.

[0106] L1 and L2 may be the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0107] n and m are each integers from 1 to 4.

[0108] Ar1 has the following chemical formula 1-C,

[0109]

[0110] In the above chemical formula 1-C,

[0111] R101 to R110 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. One of R101 to R108 must be combined with L1.

[0112] Ar2 has the following chemical formula 1-D.

[0113]

[0114] In the above chemical formula 1-D,

[0115] X is O or S.

[0116] R201 to R206 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. At least one adjacent pair of R201 to R206 must combine with each other to form more than one substituted or unsubstituted cycloalloy.

[0117] The aforementioned substituted or unsubstituted cycloalloy, or any one of R201 to R206 that does not form the aforementioned substituted or unsubstituted cycloalloy, is combined with L2.

[0118] * indicates the site where it combines with chemical formula 1.

[0119] In one embodiment of this specification, the substituted or unsubstituted cyclogroup of the above-mentioned chemical formula 1-D is any one of the organic compounds 1-D-1 to 1-D-8 described below.

[0120]

[0121] In the above chemical formulas 1-D-1 to 1-D-8,

[0122] Ra to Rc may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group; or optionally combined with adjacent groups to form substituted or unsubstituted cycloalkanes; or combined with L2 above.

[0123] p is an integer from 1 to 4. When p is 2 or more, the two or more Ra, Rb, or Rc mentioned above are either the same or different from each other.

[0124] q is an integer from 1 to 5. When q is 2 or more, the two or more Rb or Rc are the same or different from each other.

[0125] r is an integer from 1 to 6. When r is 2 or more, the two or more Ra values ​​are either the same or different from each other.

[0126] * indicates a pair of adjacent sites that bind to each other in the R201 to R206 of chemical formula 1-D.

[0127] In one embodiment of this specification, the Ra to Rc mentioned above may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, or substituted or unsubstituted heterocyclic group with 2 to 30 carbon atoms; or optionally combined with adjacent groups to form substituted or unsubstituted cyclic groups; or combined with L2 mentioned above.

[0128] In one embodiment of this specification, the Ra to Rc mentioned above may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 20 carbon atoms, or substituted or unsubstituted heterocyclic group with 2 to 20 carbon atoms; or optionally combined with adjacent groups to form substituted or unsubstituted cyclic groups; or combined with L2 mentioned above.

[0129] In one embodiment of this specification, the Ra to Rc mentioned above may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 10 carbon atoms, or substituted or unsubstituted heterocyclic group with 2 to 10 carbon atoms; or optionally combined with adjacent groups to form substituted or unsubstituted cyclic groups; or combined with L2 mentioned above.

[0130] In one embodiment of this specification, the Ra to Rc mentioned above may be the same as or different from each other, each being independently hydrogen or deuterium; or optionally combined with adjacent groups to form substituted or unsubstituted cyclic groups; or combined with the L2 mentioned above.

[0131] In one embodiment of this specification, the Ra to Rc mentioned above may be the same as or different from each other, each being hydrogen independently; or optionally combined with adjacent groups to form substituted or unsubstituted cyclic groups.

[0132] In one embodiment of this specification, Ra to Rc may be the same as or different from each other, each being independently deuterium; or optionally combined with adjacent groups to form substituted or unsubstituted cyclic groups; or combined with L2.

[0133] In one embodiment of this specification, the above-mentioned chemical formula 1 is chemical formula 1-1 to chemical formula 1-1.

[0134] Any one of the organic compounds in Formulas 1-4.

[0135]

[0136] In the above chemical formulas 1-1 to 1-4,

[0137] The definitions of L1, L2, Ar2, n, and m are the same as those in Chemical Formula 1 above.

[0138] 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.

[0139] The above R101 to R110 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0140] In this specification, the above chemical formula 1 refers to the above chemical formula 1-1.

[0141] In this specification, the above chemical formula 1 refers to the above chemical formulas 1-2.

[0142] In this specification, the above chemical formula 1 refers to the above chemical formulas 1-3.

[0143] In this specification, the above chemical formula 1 refers to the above chemical formulas 1-4.

[0144] In one embodiment of this specification, the above-mentioned chemical formula 1 is one of the following chemical formulas 1-5 to 5.

[0145] Any one of the organic compounds in Formulas 1-10.

[0146]

[0147]

[0148] In the above chemical formulas 1-5 to 1-10,

[0149] The definitions of L1, L2, Ar1, X, n, and m are the same as those in Chemical Formula 1 above.

[0150] 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.

[0151] The above R201 to R206 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. At least one pair of adjacent R201 to R206 must combine with each other to form more than one substituted or unsubstituted cycloalcohol.

[0152] In this specification, the above chemical formula 1 refers to the above chemical formulas 1-5.

[0153] In this specification, the above chemical formula 1 refers to the above chemical formulas 1-6.

[0154] In this specification, the above chemical formula 1 refers to chemical formulas 1-7.

[0155] In this specification, the above chemical formula 1 refers to the above chemical formulas 1-8.

[0156] In this specification, the above chemical formula 1 refers to chemical formulas 1-9.

[0157] In this specification, the above chemical formula 1 refers to the above chemical formulas 1-10.

[0158] In one embodiment of this specification, R1 to R10, which are not combined with L1 of Formula 1-A and not combined with L2 of Formula 1-B, may be 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.

[0159] In one embodiment of this specification, R1 to R10, which are not combined with L1 of Formula 1-A and not combined with L2 of Formula 1-B, may be the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 60 carbon atoms, substituted or unsubstituted aryl with 6 to 60 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 60 carbon atoms.

[0160] In one embodiment of this specification, R1 to R10, which are not combined with L1 of the above-mentioned chemical formula 1-A and not combined with L2 of chemical formula 1-B, may be the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms.

[0161] In one embodiment of this specification, R1 to R10, which are not combined with L1 of the above-mentioned chemical formula 1-A and are not combined with L2 of chemical formula 1-B, may be the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 20 carbon atoms.

[0162] In one embodiment of this specification, R1 to R10, which are not combined with L1 of the above-mentioned chemical formula 1-A and are not combined with L2 of chemical formula 1-B, may be the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 10 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 10 carbon atoms.

[0163] In one embodiment of this specification, R1 to R10, which are not combined with L1 of Formula 1-A and not combined with L2 of Formula 1-B, may be 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 tetraphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, or substituted or unsubstituted spirodifluorenyl. Substituted or unsubstituted triphenylene, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted naphthobenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted pyrimidinyl.

[0164] In one embodiment of this specification, R1 to R10, which are not bound to L1 of Formula 1-A and not bound to L2 of Formula 1-B, may be the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted phenyl, or deuterated or unsubstituted naphthyl.

[0165] In one embodiment of this specification, R1 to R10, which are not combined with L1 of the above-mentioned chemical formula 1-A and are not combined with L2 of chemical formula 1-B, may be the same as or different from each other, and are each independently hydrogen or deuterium.

[0166] In one embodiment of this specification, R1 to R10, which are not bound to L1 of the above-mentioned chemical formula 1-A and not bound to L2 of chemical formula 1-B, are hydrogen.

[0167] In one embodiment of this specification, R1 to R10, which are not bound to L1 of the above-mentioned chemical formula 1-A and not bound to L2 of chemical formula 1-B, are deuterium.

[0168] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0169] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently directly bonded; substituted or unsubstituted aryl groups with deuterium, alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 30 carbon atoms, aryl groups having 6 to 60 carbon atoms, or heteroaryl groups having 2 to 60 carbon atoms; or substituted or unsubstituted heteroaryl groups with deuterium, alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 30 carbon atoms, aryl groups having 6 to 60 carbon atoms, or heteroaryl groups having 2 to 60 carbon atoms.

[0170] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently directly bonded; aryl groups substituted or unsubstituted with deuterium, alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 30 carbon atoms, or heteroaryl groups having 2 to 30 carbon atoms; or heteroaryl groups substituted or unsubstituted with deuterium, alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 30 carbon atoms, or heteroaryl groups having 2 to 30 carbon atoms.

[0171] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently directly bonded; substituted or unsubstituted aryl groups with deuterium, alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, or heteroaryl groups having 2 to 20 carbon atoms; or substituted or unsubstituted heteroaryl groups with deuterium, alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, or heteroaryl groups having 2 to 20 carbon atoms.

[0172] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently directly bonded; substituted or unsubstituted aryl groups with deuterium, alkyl groups having 1 to 6 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 10 carbon atoms, or heteroaryl groups having 2 to 10 carbon atoms; or substituted or unsubstituted heteroaryl groups with deuterium, alkyl groups having 1 to 6 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 10 carbon atoms, or heteroaryl groups having 2 to 10 carbon atoms.

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

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

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

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

[0177] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each independently is a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted fluorene.

[0178] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each independently is a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted terphenylene.

[0179] In one embodiment of this specification, R101 to R110 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 60 carbon atoms, substituted or unsubstituted aryl with 6 to 60 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 60 carbon atoms, and one of R101 to R108 must be combined with L1.

[0180] In one embodiment of this specification, R101 to R110 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms, and one of R101 to R108 must be combined with L1.

[0181] In one embodiment of this specification, R101 to R110 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 20 carbon atoms, and one of R101 to R108 must be combined with L1.

[0182] In one embodiment of this specification, R101 to R110 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 10 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 10 carbon atoms, and one of R101 to R108 must be combined with L1.

[0183] In one embodiment of this specification, R101 to R110 may be the same as or different from each other, and each independently represents hydrogen, deuterium, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted spirodifluorenyl, or substituted or unsubstituted The triphenylene, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted naphthobenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted pyrimidinyl, wherein one of the above R101 to R108 must be combined with L1.

[0184] X above can be O or S.

[0185] X is O above.

[0186] X above is S.

[0187] In one embodiment of this specification, R201 to R206 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. At least one pair of adjacent R201 to R206 must combine with each other to form more than one substituted or unsubstituted cyclogroup.

[0188] In one embodiment of this specification, R201 to R206 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. At least one pair of adjacent R201 to R204 must combine with each other to form more than one substituted or unsubstituted cycloalcohol.

[0189] In one embodiment of this specification, R201 to R206 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 60 carbon atoms, substituted or unsubstituted aryl with 6 to 60 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 60 carbon atoms. At least one pair of adjacent R201 to R206 must be combined with each other to form more than one substituted or unsubstituted cyclogroup.

[0190] In one embodiment of this specification, R201 to R206 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 60 carbon atoms, substituted or unsubstituted aryl with 6 to 60 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 60 carbon atoms. At least one pair of adjacent R201 to R204 must be combined with each other to form more than one substituted or unsubstituted cyclogroup.

[0191] In one embodiment of this specification, R201 to R206 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms. At least one pair of adjacent R201 to R206 must be combined with each other to form more than one substituted or unsubstituted cyclogroup.

[0192] In one embodiment of this specification, R201 to R206 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms. At least one pair of adjacent R201 to R204 must be combined with each other to form more than one substituted or unsubstituted cycloalcoholic group.

[0193] In one embodiment of this specification, R201 to R206 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 20 carbon atoms. At least one pair of adjacent R201 to R206 must be combined with each other to form more than one substituted or unsubstituted cycloalloy.

[0194] In one embodiment of this specification, R201 to R206 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 20 carbon atoms. At least one pair of adjacent R201 to R204 must be combined with each other to form more than one substituted or unsubstituted cyclogroup.

[0195] In one embodiment of this specification, R201 to R206 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 10 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 10 carbon atoms. At least one pair of adjacent R201 to R206 must be combined with each other to form more than one substituted or unsubstituted cyclogroup.

[0196] In one embodiment of this specification, R201 to R206 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 10 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 10 carbon atoms. At least one pair of adjacent R201 to R204 must be combined with each other to form more than one substituted or unsubstituted cycloalloy.

[0197] In one embodiment of this specification, R201 to R206 may be the same as or different from each other, and each independently represents hydrogen, deuterium, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted adamantyl, etc. The following are substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted naphthobenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted pyrimidinyl, wherein at least one adjacent pair of the above R201 to R206 must combine with each other to form more than one substituted or unsubstituted cyclic group.

[0198] In one embodiment of this specification, R201 to R204 may be the same as or different from each other, and each independently represents hydrogen, deuterium, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted adamantyl, etc. The following are substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted naphthobenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted pyrimidinyl, wherein at least one adjacent pair of the above R201 to R204 must combine with each other to form more than one substituted or unsubstituted cyclic group.

[0199] In one embodiment of this specification, any one of the substituted or unsubstituted cyclogroups, or R201 to R206 that does not form the substituted or unsubstituted cyclogroups, is combined with L2.

[0200] In one embodiment of this specification, the substituted or unsubstituted cyclic group is bonded to L2.

[0201] In one embodiment of this specification, any one of R201 to R206, which does not form the aforementioned substituted or unsubstituted cyclic groups, is combined with L2.

[0202] In one embodiment of this specification, n is an integer from 1 to 4.

[0203] In one embodiment of this specification, n is 4.

[0204] In one embodiment of this specification, n is 3.

[0205] In one embodiment of this specification, n is 2.

[0206] In one embodiment of this specification, n is 1.

[0207] In one embodiment of this specification, m is an integer from 1 to 4.

[0208] In one embodiment of this specification, m is 4.

[0209] In one embodiment of this specification, m is 3.

[0210] In one embodiment of this specification, m is 2.

[0211] In one embodiment of this specification, m is 1.

[0212] According to one embodiment of this specification, R9 of chemical formula 1 is combined with L1 of chemical formula 1-A, and R10 of chemical formula 1 is combined with L2 of chemical formula 1-B.

[0213] In the above chemical formula 1, R1 to R8 are all deuterium.

[0214] According to one embodiment of this specification, the deuterium substitution rate of the above-described chemical formula 1 is 15% or more.

[0215] According to one embodiment of this specification, the deuterium substitution rate of the above-described chemical formula 1 is 30% or more.

[0216] According to one embodiment of this specification, the deuterium substitution rate of the above-described chemical formula 1 is 40% or more.

[0217] According to one embodiment of this specification, the deuterium substitution rate of the above-described chemical formula 1 is 50% or more.

[0218] According to one embodiment of this specification, the deuterium substitution rate of the above-described chemical formula 1 is 60% or more.

[0219] According to one embodiment of this specification, the deuterium substitution rate of the above-described chemical formula 1 is 70% or more.

[0220] According to one embodiment of this specification, the deuterium substitution rate of the above-described chemical formula 1 is 80% or more.

[0221] According to one embodiment of this specification, the deuterium substitution rate of the above-described chemical formula 1 is 90% or more.

[0222] According to one embodiment of this specification, the deuterium substitution rate of the above-described chemical formula 1 is 100%.

[0223] According to one embodiment of this specification, when the above-described chemical formula 1 contains deuterium, it has the following effects. Specifically, the physicochemical properties of the chemical bonds related to deuterium, such as bond length, differ from those of hydrogen. Compared to the CH bond, the CD bond has a smaller stretching amplitude, so the van der Waals radius of deuterium is smaller than that of hydrogen. Generally, the CD bond is shorter and stronger than the CH bond. Therefore, when hydrogen at the substituted position in the above-described chemical formula 1 is replaced by deuterium, the ground state energy decreases, the bond length of deuterium and carbon becomes shorter, and thus the molecular hardcore volume shrinks. This reduces electrical polarizability and weakens intermolecular interactions, thereby increasing the film volume. Furthermore, this property can create an effect of reducing the crystallinity of the film, i.e., creating an amorphous state, which can generally effectively improve the lifetime and driving characteristics of organic light-emitting devices, and further improve heat resistance compared to existing organic light-emitting devices.

[0224] In this specification, "containing deuterium", "deuterated" or "deuterated" means that hydrogen at a substituted position in a compound is replaced by deuterium.

[0225] In this specification, "per-deuterated" 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".

[0226] In this specification, "X% deuterated", "degree of deuteration X%", or "deuteration rate X%" means that X% of the hydrogens at the substituted positions in the structure are replaced with deuterium. For example, when the structure is dibenzofuran, "25% deuterated" of the aforementioned dibenzofuran, "degree of deuteration 25%" of the aforementioned dibenzofuran, or "deuteration rate 25%" of the aforementioned dibenzofuran means that 2 out of the 8 hydrogens at the substituted positions in the aforementioned dibenzofuran are replaced with deuterium.

[0227] In this specification, "degree of deuteration" or "deuteration substitution rate" can be determined by nuclear magnetic resonance spectroscopy (NMR spectroscopy). 1 The assay was confirmed using known methods such as HNMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry).

[0228] Specifically, through nuclear magnetic resonance spectroscopy (NMR spectroscopy) 1When analyzing "degree of deuteration" or "deuteration substitution rate" using ¹H NMR, DMF (dimethylformamide) can be added as an internal standard. 1 The integration ratio on H NMR is used to calculate the degree of deuteration or the rate of deuteration substitution from the total peak.

[0229] Additionally, when analyzing "degree of deuteration" or "deuteration substitution rate" using TLC / MS (thin-layer chromatography / mass spectrometry), the substitution rate can be calculated based on the maximum value (intermediate value) of the molecular weight distribution at the end of the reaction. For example, when analyzing the degree of deuteration of compound A below, the molecular weight of the starting material is 506. When specifying... Figure 3 When the maximum molecular weight (median value) of compound A in the MS chart is 527, 21 of the 26 substituted hydrogen positions in the starting material are replaced with deuterium, so it can be calculated that about 81% of the hydrogen is deuterated.

[0230]

[0231] In this specification, D represents deuterium.

[0232] In one embodiment of this specification, the above-mentioned chemical formula 1 is any one of the following organic compounds.

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243] The organic compound of Formula 1 according to one embodiment of this specification can be manufactured with a core structure as described in the manufacturing examples below. Substituents can be combined by methods known in the art, and the type, position, or number of substituents can be varied according to techniques known in the art.

[0244] In this specification, by introducing various substituents into the core structure of the organic compound of the above-described chemical formula 1, compounds with various band gaps can be synthesized. Furthermore, in this specification, by introducing various substituents into the core structure of the structure described above, the HOMO and LUMO energy levels of the compound can also be tuned.

[0245] In addition, this specification provides organic light-emitting devices that contain the organic compounds mentioned above.

[0246] In this specification, when it is stated that a component is "on" another component, it includes not only the case where one component is connected to another component, but also the case where there are other components between the two components.

[0247] The organic light-emitting device according to this specification is characterized in that it comprises: 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 comprises an organic compound represented by the above-described chemical formula 1.

[0248] The organic layers of the organic light-emitting device described in this specification can be formed as a single layer or as a multilayer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of this invention can have a structure comprising one or more of the following as organic layers: a hole transport layer, a hole injection layer, a hole modulation layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, an electron modulation layer, and an electron transport and injection layer. However, the structure of the organic light-emitting device described in this specification is not limited thereto, and may include fewer or more organic layers.

[0249] In the organic light-emitting device described in this specification, the organic light-emitting device includes a light-emitting layer, which may contain the aforementioned organic compound.

[0250] For example, an organic compound containing the above chemical formula 1 can be used as the host of the light-emitting layer.

[0251] According to one embodiment of this specification, the light-emitting layer includes a dopant, and the dopant includes a fluorescent dopant.

[0252] According to one embodiment of this specification, the fluorescent dopant is a pyrene compound or a non-pyrene compound.

[0253] According to one embodiment of this specification, the above-mentioned non-pyrene compounds include boron compounds.

[0254] According to one embodiment of this specification, the light-emitting layer further comprises one or more main components that are different from the compound of Chemical Formula 1.

[0255] In one embodiment of this specification, the main body, which is different from the compound of chemical formula 1 described above, comprises a compound of chemical formula H-1.

[0256] In one embodiment of this specification, the light-emitting layer of the organic light-emitting device comprises the organic compound as a main body, and also comprises a main body different from the organic compound, represented by the following chemical formula H-1.

[0257]

[0258] In the above chemical formula H-1,

[0259] L301 and L302 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0260] Ar301 and Ar302 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0261] 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.

[0262] r301 is an integer from 1 to 7. When r301 is 2 or more, two or more r301s are the same or different from each other.

[0263] According to one embodiment of this specification, the above chemical formula H-1 is represented by the following compound.

[0264]

[0265] For any subject that is different from the compound of Formula 1 above, as long as it is different from Formula 1 above and is an anthracene-based subject used in this technical field, it may be used without restriction and is not limited thereto.

[0266] According to one embodiment of this specification, the light-emitting layer comprises a host and a dopant.

[0267] According to one embodiment of this specification, the light-emitting layer comprises a host and a dopant, wherein the host comprises a compound represented by the above chemical formula 1.

[0268] According to one embodiment of this specification, the dopant is a blue dopant.

[0269] According to one embodiment of this specification, the above-described organic light-emitting device is a blue organic light-emitting device.

[0270] According to one embodiment of this specification, the light-emitting layer comprises a host and a dopant, the host comprising a compound represented by the above chemical formula 1, and the dopant comprising one or more selected from pyrene compounds and non-pyrene compounds.

[0271] According to one embodiment of this specification, the light-emitting layer comprises a host and a dopant, wherein the weight ratio of the host to the dopant of the light-emitting layer is 8:2 to 99:1.

[0272] According to one embodiment of this specification, the light-emitting layer comprises a host and a dopant, wherein the weight ratio of the host to the dopant of the light-emitting layer is 8:2 to 95:5.

[0273] According to one embodiment of this specification, the light-emitting layer comprises a substrate and a dopant, wherein the weight ratio of the substrate to the dopant is 90:10 to 99:1.

[0274] According to another embodiment of this specification, a covering layer is further provided on the opposite side of at least one of the first electrode and the second electrode, which is opposite to the side of the organic layer.

[0275] The aforementioned capping layer is formed to prevent a large amount of light loss due to total internal reflection in organic light-emitting devices. The capping layer has the property of fully protecting the underlying cathode and light-emitting layer from external moisture penetration or contamination, and its high refractive index can prevent light loss due to total internal reflection.

[0276] According to another embodiment of this specification, the aforementioned covering layer may be respectively disposed on the opposite side of the surface of the first electrode that is opposite to the surface of the organic layer and on the opposite side of the surface of the second electrode that is opposite to the surface of the organic layer.

[0277] According to another embodiment of this specification, the aforementioned covering layer may be disposed on the opposite side of the surface of the first electrode that is opposite to the surface of the organic layer.

[0278] According to another embodiment of this specification, the aforementioned covering layer may be disposed on the opposite side of the second electrode to the side opposite to the organic layer.

[0279] According to one embodiment of this specification, the above-mentioned organic light-emitting device further includes one or more layers selected from hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer, electron modulation layer and hole modulation layer.

[0280] According to one embodiment of this specification, the organic light-emitting device includes a first electrode; a second electrode; a light-emitting layer disposed between the first electrode and the second electrode; and two or more organic layers disposed between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0281] According to one embodiment of this specification, the two or more organic layers between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, may be selected from 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 modulation layer, an electron modulation layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer.

[0282] According to one embodiment of this specification, two or more hole transport layers are included between the light-emitting layer and the first electrode. These two or more hole transport layers may contain the same or different materials.

[0283] According to one embodiment of this specification, the first electrode is an anode or a cathode.

[0284] According to one embodiment of this specification, the second electrode is a cathode or an anode.

[0285] According to one embodiment of this specification, the above-mentioned organic light-emitting device may be an organic light-emitting device with an anode, one or more organic layers and a cathode sequentially stacked on a substrate (normal type).

[0286] According to one embodiment of this specification, the organic light-emitting device can be an organic light-emitting device with a reverse structure (inverted type) in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate.

[0287] For example, the structure of an organic light-emitting device according to one embodiment of this specification is illustrated in... Figure 1 and 2 The above. Figure 1 and 2 Organic light-emitting devices are illustrated, but not limited to them.

[0288] Figure 1 The diagram illustrates the structure of an organic light-emitting device in which a first electrode 2, a light-emitting layer 4, and a second electrode 3 are sequentially stacked on a substrate 1. The aforementioned compound is contained within the light-emitting layer.

[0289] Figure 2 The diagram illustrates the structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, a hole modulation layer 7, a light-emitting layer 4, an electron modulation 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 aforementioned compound is contained within the light-emitting layer.

[0290] The organic light-emitting device described in this specification, except that the light-emitting layer contains the aforementioned compound, namely the compound of chemical formula 1, can be manufactured using materials and methods known in the art.

[0291] When the aforementioned organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed from the same substance or different substances.

[0292] For example, the organic light-emitting device of this specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be achieved by: depositing a metal or a conductive metal oxide or alloy thereof onto the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; then forming an organic layer on the anode, comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer; and finally depositing a material suitable for use as a cathode onto the organic layer. Alternatively, the organic light-emitting device can also be manufactured by sequentially depositing a second electrode material, an organic layer, and a first electrode material onto the substrate.

[0293] Furthermore, the compound represented by the above chemical formula 1 can be used to form an organic layer in the manufacture of organic light-emitting devices not only by vacuum evaporation but also by solution coating. Here, solution coating refers to methods such as spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, and roller coating, but is not limited to these.

[0294] In addition to these methods, organic light-emitting devices can also be fabricated by sequentially depositing a second electrode material, an organic layer, and a first electrode material on a substrate. However, the manufacturing method is not limited to these methods.

[0295] As the first electrode material mentioned above, a material with a high work function is preferred in order to facilitate the injection of holes into the organic layer. For example, 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-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but not limited to these.

[0296] As the second electrode material mentioned above, a material with a low work function is generally preferred in order to facilitate the injection of electrons into the organic layer. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer materials such as LiF / Al or LiO2 / Al, etc., are used, but are not limited to these.

[0297] The aforementioned light-emitting layer may comprise a host material and a dopant material. When the light-emitting layer includes a material other than the one comprising a compound of chemical formula 1 according to an embodiment of this specification, the host material may be an aromatic fused-ring derivative and / or an aromatic non-fused-ring derivative or a heterocyclic compound. Specifically, as aromatic fused-ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, fluoranthene compounds, etc.; as heterocyclic compounds, there are dibenzofuran derivatives, ladder-type furans, etc. Pyrimidine derivatives, etc., but not limited to these.

[0298] According to one embodiment of this specification, the above-described subject comprises, but is not limited to, a compound represented by the above-described chemical formula 2.

[0299] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are aromatic fused-ring derivatives with substituted or unsubstituted aryl amine groups, such as pyrene, anthracene, etc., which have aryl amine groups. Diindrone pyrene, etc. Furthermore, styrylamine compounds are compounds in which at least one aryl vinyl group is substituted onto a substituted or unsubstituted arylamine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups. Specifically, there are styrylamines, styryldiamines, styryltriamines, styryltetraamines, etc., but they are not limited to these. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but they are not limited to these.

[0300] According to one embodiment of this specification, the dopant material comprises, but is not limited to, a compound with the following chemical formula D-1 or D-2.

[0301]

[0302]

[0303] In the above chemical formula D-1,

[0304] L101 and L102 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group.

[0305] Ar101 to Ar104 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0306]

[0307] In the above chemical formula D-2,

[0308] T1 to T5 may be the same as or different from each other, and each is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted amino, or substituted or unsubstituted aryl.

[0309] t3 and t4 are each integers from 1 to 4.

[0310] t5 is an integer from 1 to 3.

[0311] When t3 is 2 or more, the two or more T3 values ​​are either the same or different from each other.

[0312] When t4 is 2 or more, the two or more T4 values ​​are either the same or different from each other.

[0313] When t5 is 2 or more, the two or more T5s mentioned above are either the same or different from each other.

[0314] According to one embodiment of this specification, L101 and L102 are directly bonded.

[0315] According to one embodiment of this specification, Ar101 to Ar104 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms.

[0316] According to one embodiment of this specification, Ar101 to Ar104 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms substituted or unsubstituted by a straight-chain or branched alkyl group with 1 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group with 2 to 30 carbon atoms.

[0317] According to one embodiment of this specification, Ar101 to Ar104 may be the same as or different from each other, and each is independently a phenyl substituted with methyl or a dibenzofuranyl.

[0318] According to one embodiment of this specification, the above chemical formula D-1 is represented by the following compound.

[0319]

[0320] According to one embodiment of this specification, T1 to T5 may be the same as or different from each other, and each is independently hydrogen, a straight-chain or branched alkyl group with 1 to 30 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic arylamine group with 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0321] According to one embodiment of this specification, T1 to T5 may be the same as or different from each other, and each is independently hydrogen, a straight-chain 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 substituted or unsubstituted by a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0322] According to one embodiment of this specification, T1 to T5 may be the same as or different from each other, and each is independently hydrogen, methyl, tert-butyl, diphenylamino, or phenyl substituted with or unsubstituted with methyl or tert-butyl.

[0323] According to one embodiment of this specification, the above chemical formula D-2 is represented by the following compound.

[0324]

[0325] The aforementioned 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, the effect of receiving holes from the anode, and an excellent hole injection effect on the light-emitting layer or light-emitting material. Furthermore, it is preferably a material with excellent ability to prevent excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material. Furthermore, it is preferably a material with excellent thin film forming ability. Furthermore, it is preferable 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, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds; hexanitrile hexaazabenzophenanthrene-based organic compounds; quinacridone-based organic compounds; perylene-based organic compounds; anthraquinones, polyaniline, and polythiophene-based conductive polymers.

[0326] According to one embodiment of this specification, the hole injection layer comprises, but is not limited to, a compound represented by the chemical formula HI-1.

[0327]

[0328] In the above chemical formula HI-1,

[0329] At least one of X'1 to X'6 is N, and the rest are CH.

[0330] R309 to R314 may be the same as or different from each other, and each is independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or combined with adjacent groups to form substituted or unsubstituted rings.

[0331] According to one embodiment of this specification, X'1 to X'6 are N.

[0332] According to one embodiment of this specification, R309 to R314 are cyano groups.

[0333] According to one embodiment of this specification, the above chemical formula HI-1 is represented by the following compound.

[0334]

[0335] The aforementioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The 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, and is preferably a substance with a high hole mobility. Specific examples include arylamine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0336] According to one embodiment of this specification, the hole transport layer or hole modulation layer comprises, but is not limited to, a compound with the chemical formula HT-1.

[0337]

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

[0339] R315 to R317 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or may be combined with adjacent groups to form substituted or unsubstituted rings.

[0340] r315 is an integer from 1 to 5. When r315 is 2 or more, two or more of the above R315 are either the same or different from each other.

[0341] r316 is an integer from 1 to 5. When r316 is 2 or more, two or more of the above R316 are the same or different from each other.

[0342] According to one embodiment of this specification, R317 is selected from any one of substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, and combinations thereof.

[0343] According to one embodiment of this specification, R317 is selected from carbazolyl, phenyl, biphenyl, fluorenyl, and combinations thereof.

[0344] According to one embodiment of this specification, R315 and R316 may be the same as or different from each other, each being independently a substituted or unsubstituted aryl group, or combined with adjacent groups to form an alkyl-substituted aromatic hydrocarbon ring.

[0345] According to one embodiment of this specification, R315 and R316 may be the same as or different from each other, each being independently phenyl or phenanthrene, or combined with adjacent groups to form methyl-substituted indene.

[0346] According to one embodiment of this specification, the above chemical formula HT-1 is represented by any one of the following compounds.

[0347]

[0348] The aforementioned hole modulation layer is a layer that improves device lifetime and efficiency by regulating the smooth injection of holes from the hole transport layer into the light-emitting layer and preventing electrons injected from the electron injection layer from passing through the light-emitting layer into the hole injection layer. It can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and a layer that simultaneously performs hole injection and hole transport. Known materials can be used without restriction.

[0349] The material of the hole regulation layer described above can be an example of the chemical formula HT-I, but is not limited thereto.

[0350] The aforementioned electron conditioning layer is a layer that regulates the smooth injection of electrons from the electron transport layer into the light-emitting layer, and can use known materials without restriction.

[0351] According to one embodiment of this specification, the above-mentioned electronic conditioning layer comprises, but is not limited to, a compound with the following chemical formula EG-1.

[0352]

[0353]

[0354] In the above chemical formula EG-1,

[0355] At least one of G1 to G18 is -L5-Ar5, and the rest are hydrogen, or G1 and G18 are connected by -L51- to form a substituted or unsubstituted ring.

[0356] L5 is a directly bonded, substituted, or unsubstituted aryl group.

[0357] Ar5 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0358] L51 is either O or S.

[0359] According to one embodiment of this specification, L51 is O.

[0360] According to one embodiment of this specification, L51 is S.

[0361] According to one embodiment of this specification, G1 and G18 are connected by -L51- to form substituted or unsubstituted heterocyclic rings.

[0362] According to one embodiment of this specification, G1 and G18 are connected by -L51- to form a substituted or unsubstituted thiol ring or a substituted or unsubstituted thiol ring.

[0363] According to one embodiment of this specification, G1 and G18 are connected by -O- to form a substituted or unsubstituted thallium ring.

[0364] According to one embodiment of this specification, G1 and G18 are connected by -S- to form a substituted or unsubstituted thioxanthate ring.

[0365] According to one embodiment of this specification, G1 and G18 are connected by -O- to form a thorium ring.

[0366] According to one embodiment of this specification, G1 and G18 are connected by -S- to form a thiotonium ring.

[0367] According to one embodiment of this specification, L5 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms that is directly bonded, substituted, or unsubstituted.

[0368] According to one embodiment of this specification, L5 is a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms that is directly bonded, substituted, or unsubstituted.

[0369] According to one embodiment of this specification, L5 is a directly bonded, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0370] According to one embodiment of this specification, L5 is a directly bonded, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0371] According to one embodiment of this specification, L5 is directly bonded or phenylene.

[0372] According to one embodiment of this specification, Ar5 is a substituted or unsubstituted triazine group.

[0373] According to one embodiment of this specification, the Ar5 mentioned above is a triazine group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0374] According to one embodiment of this specification, Ar5 is a triazine group substituted with phenyl.

[0375] According to one embodiment of this specification, the above-mentioned EG-1 is represented by the following compound.

[0376]

[0377] The aforementioned electron transport layer is the layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a substance capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, preferably a substance with high electron mobility. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, and hydroxyflavonoid-metal complexes, but are not limited to these. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, suitable cathode materials are generally materials with low work functions and accompanied by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium are examples, each accompanied by an aluminum or silver layer.

[0378] According to one embodiment of this specification, the electron transport layer comprises, but is not limited to, a compound with the chemical formula ET-1.

[0379]

[0380]

[0381] In the above chemical formula ET-1,

[0382] At least one of Z11 to Z13 is N, and the rest are CH.

[0383] L601 is a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0384] Ar601 and Ar602 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0385] l601 is an integer from 1 to 5. When l601 is 2 or more, the two or more l601 are the same or different from each other.

[0386] According to one embodiment of this specification, L601 is a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

[0387] According to one embodiment of this specification, L601 is phenylene, biphenylene, or naphthylene.

[0388] According to one embodiment of this specification, Ar601 and Ar602 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0389] According to one embodiment of this specification, Ar601 and Ar602 are phenyl groups.

[0390] According to one embodiment of this specification, the above-mentioned chemical formula ET-1 is represented by the following compound.

[0391]

[0392] The aforementioned electron injection layer is a layer that receives electrons from the electrode. Preferably, the electron injection material is one that exhibits excellent electron transport capabilities, effectively receives electrons from the second electrode, and provides excellent electron injection for the light-emitting layer or light-emitting material. Furthermore, it is preferably a material that prevents excitons generated in the light-emitting layer from migrating to the hole injection layer and possesses excellent thin film formation capabilities. Specifically, materials such as fluorenone, anthraquinone dimethyl ether, biphenylquinone, and thiamethoxam dioxide are preferred. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0393] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium, but are not limited to these.

[0394] According to one embodiment of this specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. The electron injection and transport layer may use the materials exemplified in the electron transport layer and electron injection layer, but is not limited thereto.

[0395] According to one embodiment of this specification, the electron injection and transport layer may further comprise a metal coordination compound. The metal coordination compound is as described above.

[0396] The aforementioned hole conditioning layer is a layer that prevents electrons injected from the electron injection layer from passing through the light-emitting layer into the hole injection layer, thereby improving the device's lifetime and efficiency. Known materials can be used without limitation, and it can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and a layer that simultaneously performs hole injection and hole transport.

[0397] The aforementioned electron conditioning layer is a layer that prevents holes from reaching the cathode, and it can typically be formed using the same conditions as the electron injection layer. Specifically, there are... Diazole derivatives or triazole derivatives, phenanthrene-rhein derivatives, aluminum complexes, etc., but not limited to these.

[0398] The aforementioned capping layer is formed to prevent the loss of a large amount of light through total internal reflection in organic light-emitting devices. The capping layer has the property of fully protecting the underlying cathode and light-emitting layer from external moisture penetration or contamination. It has a high refractive index to prevent light loss due to total internal reflection and can use existing materials without restriction.

[0399] According to one embodiment of this specification, the aforementioned covering layer comprises a compound represented by the following chemical formula CP-1, but is not limited thereto.

[0400]

[0401]

[0402] In the above chemical formula CP-1,

[0403] L501 and L502 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.

[0404] R501 and Ar501 to Ar504 may be the same as or different from each other, each being independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent groups may combine to form a substituted or unsubstituted ring.

[0405] According to one embodiment of this specification, L501 and L502 may be the same as or different from each other, and each is independently a monocyclic or polycyclic arylene group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0406] According to one embodiment of this specification, L501 and L502 are phenylene oxides.

[0407] According to one embodiment of this specification, R501 and Ar501 to Ar504 may be the same as or different from each other, each being independently a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heterocyclic monocyclic or polycyclic group with 2 to 30 substituted or unsubstituted carbon atoms formed by combining with adjacent groups.

[0408] According to one embodiment of this specification, R501 and Ar501 to Ar504 are phenyl groups, or they are combined with adjacent groups to form phenyl-substituted or unsubstituted carbazoles.

[0409] According to one embodiment of this specification, the above-mentioned Ar501 and L501 are combined to form a phenyl-substituted carbazole.

[0410] According to one embodiment of this specification, the above-mentioned Ar503 and L503 are combined to form a phenyl-substituted carbazole.

[0411] According to one embodiment of this specification, the above-mentioned chemical formula CP-1 is represented by the following compound.

[0412]

[0413] Depending on the materials used, the organic light-emitting device according to this specification can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0414] The organic light-emitting device according to this specification can be included in and used in various electronic devices. For example, the aforementioned electronic devices can be display panels, touch panels, solar modules, lighting devices, etc., and are not limited thereto.

[0415] The following detailed description, using embodiments, aims to provide a more specific explanation of this specification. However, the embodiments described herein can be modified in various ways and are not intended to limit the scope of this application to the embodiments detailed below. These embodiments are provided to provide a more complete explanation of this specification to those skilled in the art.

[0416] Manufacturing Example 1 (Synthesis of Chemical Formula 1)

[0417] 1) Synthesis of chemical formula A1

[0418]

[0419] SM1 (A0, 1 equivalent) and SM2 (1.1 equivalent) were added to tetrahydrofuran (THF) (excess), followed by the addition of 2M aqueous potassium carbonate solution (30 v / v relative to THF), and then tetra(triphenylphosphine)palladium (2 mol%). The mixture was heated and stirred at 85°C for 10 hours. After cooling to room temperature and stopping the reaction, the aqueous potassium carbonate solution was removed, and column chromatography was performed using hexane and ethyl acetate to produce the above-mentioned chemical formulas A1 (A1-1 to A1-5).

[0420] In the above-mentioned synthesis method of chemical formula A1, SM1 and SM2 were replaced with the substances listed in Table 1 below. Otherwise, A1-1 to A1-5 of [Table 1] were synthesized by the same method.

[0421] Table 1

[0422]

[0423] 2) Synthesis of chemical formulas A2 and B2

[0424]

[0425] SM1 (one of A1 or B0, 1 equivalent) and SM2 (one of P1 or P2, 1.1 equivalent) were added to tetrahydrofuran (THF) (in excess), followed by the addition of 2M aqueous potassium carbonate solution (30 v / v relative to THF), and then tetra(triphenylphosphine)palladium (2 mol%). The mixture was heated and stirred at 85°C for 10 hours. After cooling to room temperature and terminating the reaction, the aqueous potassium carbonate solution was removed, and column chromatography with hexane and ethyl acetate was performed to produce the above-mentioned chemical formulas A2 and B2 (A2-1 to A2-3 and B2-1 to B2-5).

[0426] In the above-mentioned synthesis methods of chemical formulas A2 and B2, SM1 and SM2 were replaced with the substances listed in Tables 2 and 3 below. Otherwise, A2-1 to A2-3 in [Table 2] and B2-1 to B2-5 in [Table 3] were synthesized by the same method.

[0427] Table 2

[0428]

[0429] Table 3

[0430]

[0431] 3) Synthesis of chemical formulas A3 and B3

[0432]

[0433] Add SM1 (one of A1, A2, B0, and B2, 1 equivalent) and SM2 (1.3 equivalent) to 1,4-di Add potassium acetate (3 equivalents) to alkylene (12 times <mass ratio> relative to SM1), stir and reflux. Add bis(diphenylphosphine)ferrocene palladium dichloride (0.05 equivalents) to 1,4-dialkylene oxide. After stirring in alkane for 5 minutes, the mixture was added. After 2 hours, once the reaction was confirmed to be complete, it was cooled to room temperature. Ethanol and water were added, and the mixture was filtered. It was then purified by recrystallization with ethyl acetate and ethanol to produce the above-mentioned chemical formulas A3 and B3 (A3-1 to A3-8 and B3-1 to B3-31).

[0434] In the above synthesis methods of chemical formulas A3 and B3, SM1 and SM2 were replaced with the substances listed in Tables 4 and 5 below. Otherwise, A3-1 to A3-8 in [Table 4] and B3-1 to B3-31 in [Table 5] were synthesized by the same method.

[0435] Table 4

[0436]

[0437]

[0438] Table 5

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445] In the synthesis of the above chemical formula B3, B3-1 to B3-25 were synthesized with reference to LGC KR 2024-0003039A, KR 2024-0003040 A, and KR 2024-0002594 A, and B3-26 to B3-31 were synthesized with reference to LGC KR 2024-0007056A.

[0446] 4) Synthesis of Int 1.

[0447]

[0448] After adding SM1 (one of A3, 1 equivalent) and SM2 (1 equivalent) to tetrahydrofuran (excess), 2M of potassium carbonate aqueous solution (30 v / v relative to THF) was added, followed by the addition of tetra(triphenylphosphine)palladium (2 mol%). The mixture was heated and stirred at 85°C for 10 hours. The temperature was then lowered to room temperature, and after the reaction was complete, the potassium carbonate aqueous solution was removed. Layer separation was performed, and the mixture was recrystallized from chloroform and ethyl acetate to produce the above-mentioned chemical formula int. (int 1-1. to int 1-14.).

[0449] In the synthesis method of the above chemical formula int 1., SM1 and SM2 were replaced with the substances in Table 6 below. Otherwise, int 1-1 to int 1-14 of [Table 6] were synthesized by the same method.

[0450] Table 6

[0451]

[0452]

[0453]

[0454] 5) Synthesis of Int 2.

[0455]

[0456] SM1 (one of int 1., 1 equivalent) was dissolved in chloroform (excess), and the temperature was lowered to 0°C. After stabilization, N-bromosuccinimide (NBS) (1 equivalent) was dissolved in dimethylformamide (DMF) (excess) and added dropwise. The reactants were then heated to room temperature and stirred for 1 hour. 1N HCl (excess) was added to terminate the reaction. After the reaction was complete, layer separation was performed. After removing the solvent, the residue was subjected to silica gel column chromatography (ethyl acetate / hexane 1:15) to produce int 2. (int 2-1. to int 2-14.).

[0457] In the synthesis method of the above chemical formula int 2., SM1 and SM2 were replaced with the substances in Table 7 below. Otherwise, int 2-1 to int 2-14 of [Table 7] were synthesized by the same method.

[0458] Table 7

[0459]

[0460]

[0461]

[0462] 6) Synthesis of Chemical Formula 1

[0463]

[0464] After adding SM1 (one of int 2., 1 equivalent) and SM2 (1.1 equivalent) to tetrahydrofuran (excess), 2M aqueous potassium carbonate solution (30 v / v relative to THF) was added, followed by the addition of tetra(triphenylphosphine)palladium (2 mol%). The mixture was heated and stirred at 85°C for 10 hours. After cooling to room temperature and stopping the reaction, the aqueous potassium carbonate solution was removed, and column chromatography was performed using hexane and ethyl acetate to produce the above-mentioned chemical formula 1 (compounds 1 to 31).

[0465] In the above-mentioned synthesis method of chemical formula int., SM1 and SM2 were replaced with the substances in Table 8 below. Otherwise, compounds 1 to 31 in [Table 8] were synthesized by the same method.

[0466] Table 8

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473] 7) Synthesis of chemical formula 1D

[0474] The reactants (1 equivalent) and trifluoromethanesulfonic acid (catalyst (cat.)) were added to C6D6 (10–50 times the mass of the reactants), and the mixture was stirred at 70°C for 10 to 100 minutes. After the reaction was complete, D2O (excess) was added, and the mixture was stirred for 30 minutes, followed by the dropwise addition of trimethylamine (excess). The reaction mixture was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried over MgSO4 and recrystallized by heating with toluene to obtain the products (compounds 32 to 35) listed in Table 9 below.

[0475] Table 9

[0476]

[0477] The products vary in degree of deuterium substitution depending on the reaction time, based on the maximum m / z (M + The value determines the substitution rate.

[0478] <Example 1> Manufacturing of OLEDs

[0479] ITO / Ag / ITO will be used as the anode. The vapor-deposited substrate was cut into 50mm × 50mm × 0.5mm pieces and placed in distilled water containing a dispersant. It was then ultrasonically washed. The detergent used was from Fischer Co., and the distilled water was filtered twice using a Millipore Co. filter. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for 10 minutes of ultrasonic washing. Following the distilled water washing, the substrate was ultrasonically washed sequentially with isopropanol, acetone, and methanol, and then dried.

[0480] On the anode prepared in this way, HI-1 is... A hole injection layer is formed by thermal vacuum evaporation of a material of a certain thickness. On this hole injection layer, HT1, the material used to transport holes, is applied at a thickness of [insert thickness here]. A hole transport layer is formed by vacuum evaporation. Then, EB1 is used. A hole modulation layer is formed. Then, as the light-emitting layer, the host compound 1 synthesized in Manufacturing Example 1 and the dopant BD1 (2 wt%) are used... The thickness is formed by vacuum evaporation. Then, HB1 is deposited. To form an electronic regulation layer, compounds ET1 and Liq are mixed in a 5:5 (mass ratio) to form a layer of thickness. The electron transport layer. Sequentially... A thick film of magnesium and lithium fluoride (LiF) forms the electron injection layer. <eil>Subsequently, as the cathode, it is formed using magnesium and silver (1:4). Then, CP1 is vapor-deposited. Thus, the device was completed. During the above process, the evaporation rate of the organic material was maintained. / sec.

[0481]

[0482] [Comparative Examples 1 to 8 and Examples 2 to 39]

[0483] In Comparative Examples 1 to 8 and Examples 2 to 39 described above, the substances described in Table 10 below were used as materials for the light-emitting layer, and the devices were manufactured by the same method as in Example 1 described above.

[0484] For the devices manufactured in Comparative Examples 1 to 8 and Examples 1 to 39 above, at 20 mA / cm 2 The driving voltage, luminous efficiency, and time to reach 95% relative to the initial luminance (LT95) were measured at a current density. The results are shown below [Table 10].

[0485]

[0486] Table 10

[0487]

[0488]

[0489]

[0490] The results of [Table 10] above are as follows: a device structure having a light-emitting layer, and the main body of the light-emitting layer is a single body, while the compound for which protection is sought in this application constitutes the main body of the light-emitting layer.

[0491] Comparative Example 1 involved the bonding of phenanthrene at position 3 to anthracene at position 10, the bonding of unsubstituted benzofuran at position 2 to anthracene at position 9, and the introduction of deuterium into both anthracene and the unsubstituted benzofuran. The difference in this application is that an additional substituent is present when the benzofuran at position 2 bonds to anthracene at position 9. It can be confirmed that the compounds of the embodiments of this application, due to the introduction of a benzofuran core fused with benzene or benzofuran, exhibit structural stability and carrier injection and migration rates different from the comparative examples, demonstrating superior performance in this device structure, particularly in terms of voltage and lifetime.

[0492] Furthermore, Examples 14 to 17 exhibited superior device characteristics compared to Comparative Examples 1 and 2 by further introducing substituents into the phenanthrene nucleus under the conditions described above.

[0493] As can be seen from Examples 22 to 25, the electrical characteristics can be adjusted by introducing connecting clusters, which can improve the lifespan while maintaining the advantages of the corresponding structure.

[0494] As can be seen from Examples 26 to 31, benzofuran nuclei fused with benzofuran were introduced, showing advantages in terms of voltage.

[0495] Furthermore, Examples 32 to 35 showed an average lifetime improvement of 10 to 15% through further deuterium substitution, and although there were disadvantages in terms of cost, they showed the effect of further improving lifetime. Examples 36 to 39 involved changes in dopant (pyrene dopant -> boron dopant), which maintained the trend of the device while keeping the dopant characteristics changed. Therefore, when various dopants were introduced, the consistency of the device could be shown.

[0496] <Example 40> OLED Manufacturing

[0497] ITO / Ag / ITO will be used as the anode. The vapor-deposited substrate was cut into 50mm × 50mm × 0.5mm pieces and placed in distilled water containing a dispersant. It was then ultrasonically washed. The detergent used was from Fischer Pharmaceuticals, and the distilled water was filtered twice using a Millipore filter. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for 10 minutes each time. Following the distilled water washing, the substrate was ultrasonically washed in the following order: isopropanol, acetone, and methanol, and then dried.

[0498] On the anode prepared in this way, HI-1 is... A hole injection layer is formed by thermal vacuum evaporation of a material of a certain thickness. On this hole injection layer, HT1, the material used to transport holes, is applied at a thickness of [insert thickness here]. A hole transport layer is formed by vacuum evaporation. Then, EB1 is used. A hole modulation layer is formed. Then, as the light-emitting layer, the host compound 2 synthesized in Manufacturing Example 1 is mixed with BH13 and dopant BD1 (2 wt%). A light-emitting layer is formed by vacuum co-evaporation of a material of a certain thickness. Then, HB1 is deposited... To form an electronic regulation layer, compounds ET1 and Liq are mixed in a 5:5 (mass ratio) to form a layer of thickness. The electron transport layer. Sequentially... A thick film of magnesium and lithium fluoride (LiF) forms the electron injection layer. <eil>Subsequently, as the cathode, it is formed using magnesium and silver (1:4). Then, CP1 is vapor-deposited. The device was thus completed. During the above process, the evaporation rate of the organic material was maintained. / sec.

[0499]

[0500] [Comparative Examples 9 to 14 and Examples 41 to 44]

[0501] In Comparative Examples 9 to 14 and Examples 41 to 44 described above, the substances listed in Table 2 below were used as the materials for the light-emitting layer. Otherwise, the devices were manufactured using the same method as in Example 27 described above.

[0502] However, the following embodiment is used: as shown in [Table 11], the light-emitting layer is formed by co-evaporating two types of substrates using different evaporation sources during device fabrication.

[0503] The devices manufactured in Comparative Examples 9 to 14 and Examples 40 to 44 were tested at 20 mA / cm. 2 The driving voltage, luminous efficiency, and time to reach 95% of the initial luminance (LT95) were measured at a current density. The results are shown below [Table 11].

[0504] Table 11

[0505]

[0506] The results in Table 11 above show the case where the main body of the luminescent layer is composed of a mixed body (a body composed of two anthracene species).

[0507] Comparative Examples 9 to 12 illustrate, as comparative examples, the formation of a mixed matrix of widely used aryl anthracene compounds BH13 and BH14 with BH1, BH2, BH3, and BH4 in the structure of this application. It was observed that devices with the corresponding combinations of light-emitting layers showed partially improved device results in terms of voltage, efficiency, and lifetime. Furthermore, Comparative Examples 13 to 14 showed the same trend even when boron-based blue dopants were applied.

[0508] Examples 40 to 44 are device results observed when compounds 28 to 31 from the examples of the claimed compound are mixed with the preceding BH13 or BH14. It can be seen that the compounds of the claimed compound, which have superior properties compared to Comparative Examples 9 to 14, also exhibit the same trend under mixed-body conditions.< / eil> < / eil>

Claims

1. An organic compound of chemical formula 1: [Chemical Formula 1] In the chemical formula 1, One or more of R1 to R10 are combined with L1 of the chemical formula 1-A. One or more of R1 to R10 that are not bound to L1 of chemical formula 1-A are bound to L2 of chemical formula 1-B. R1 to R10, which are not combined with L1 of Formula 1-A and not combined with L2 of Formula 1-B, may be 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. L1 and L2 may be the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. n and m are each integers from 1 to 4. Ar1 has the following chemical formula 1-C, [Chemical Formula 1-C] In the chemical formula 1-C, R101 to R110 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, wherein one of R101 to R108 must be combined with L1. Ar2 has the following chemical formula 1-D. [Chemical Formula 1-D] In the chemical formula 1-D, X is O or S. R201 to R206 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. At least one adjacent pair of R201 to R206 must combine with each other to form more than one substituted or unsubstituted cycloalloy. The substituted or unsubstituted cyclogroup, or any one of R201 to R206 that does not form the substituted or unsubstituted cyclogroup, binds to L2. * indicates the site where it combines with chemical formula 1.

2. The organic compound according to claim 1, wherein, The substituted or unsubstituted cycloalcoholic group of the chemical formula 1-D is any one of the following 1-D-1 to 1-D-8: In the chemical formulas 1-D-1 to 1-D-8, Ra to Rc may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group; or optionally combined with adjacent groups to form substituted or unsubstituted cyclic groups; or combined with said L2, p is an integer from 1 to 4. When p is 2 or more, two or more of Ra, Rb, or Rc are the same or different from each other. q is an integer from 1 to 5. When q is 2 or more, two or more Rb or Rc are the same or different from each other. r is an integer from 1 to 6. When r is 2 or more, two or more Ra are the same or different from each other. * indicates a pair of adjacent sites that bind to each other in the R201 to R206 of chemical formula 1-D.

3. 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, 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. R101 to R110 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

4. 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, 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. R201 to R206 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. At least one pair of adjacent R201 to R206 must combine with each other to form more than one substituted or unsubstituted cyclogroup.

5. The organic compound according to claim 1, wherein, R9 of chemical formula 1 combines with L1 of chemical formula 1-A, R10 of chemical formula 1 combines with L2 of chemical formula 1-B, and R1 to R8 of chemical formula 1 are all deuterium.

6. The organic compound according to claim 1, wherein, The deuterium substitution rate of chemical formula 1 is 15% or more.

7. The organic compound according to claim 1, wherein, 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 disposed between the anode and the cathode, wherein one or more of the organic layers comprise an organic compound as described in 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, which contains the organic compound.

10. The organic light-emitting device according to claim 9, wherein, The light-emitting layer contains the organic compound as the main body of the light-emitting layer.

11. The organic light-emitting device according to claim 9, wherein, The luminescent layer comprises the organic compound as the main component, and also comprises a main component different from the organic compound, represented by the following chemical formula H-1: [Chemical formula H-1] In the chemical formula H-1, L301 and L302 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. Ar301 and Ar302 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic. R301 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. r301 is an integer from 1 to 7. When r301 is 2 or more, two or more r301s are the same or different from each other.

12. The organic light-emitting device according to claim 10, wherein, The light-emitting layer comprises the organic compound as the main component and also contains dopants.

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