Compound, and organic light-emitting element comprising same

Abstract

The present specification relates to: a compound of chemical formula 1; and an organic light-emitting element comprising same.

Description

Compounds and organic light-emitting devices containing the same

[0001] This specification relates to a compound and an organic light-emitting device containing the same.

[0002] This application claims the benefit of the filing date of Korean Patent Application No. 10-2024-0188532 filed with the Korean Intellectual Property Office on December 17, 2024, the entire contents of which are incorporated herein.

[0003] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) that utilize this phenomenon typically have a structure comprising an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to enhance the efficiency and stability of the OLED; for example, it may consist of a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, and an electron injection layer. In the structure of such an OLED, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall back to the ground state.

[0004] The development of new materials for organic light-emitting devices as described above is continuously required.

[0005] The present specification aims to provide a compound and an organic light-emitting device containing the same.

[0006] The present specification provides a compound of the following chemical formula 1.

[0007] [Chemical Formula 1]

[0008]

[0009] In the above chemical formula 1,

[0010] HAr1 and HAr2 are identical or different from each other, each independently substituted or unsubstituted, and are heterocyclic rings comprising two or more heteroatoms selected from the group consisting of N, O and S, and

[0011] L1 and L2 are identical or different from each other, and each is an independently substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0012] n1 and n2 are identical or different from each other and are each independently integers from 1 to 5, and if n2 is 2 or more, L1 and L2 are identical or different from each other, and

[0013] At least one of the above HAr1 and HAr2 is substituted with one or more of the following chemical formula 2, and

[0014] [Chemical Formula 2]

[0015]

[0016] In the above chemical formula 2,

[0017] Z1 is O; or S, and

[0018] L3 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0019] R1 is hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted aryl group; substituted or unsubstituted aryloxy group; substituted or unsubstituted arylthio group; or substituted or unsubstituted heteroaryl group, and

[0020] n3 is an integer from 0 to 5, and if it is 2 or greater, L3 are identical or different from each other, and

[0021] m1 is an integer from 1 to 3, and

[0022] r1 is an integer from 0 to 2, and when r1 is 2, R1 are the same or different.

[0023] r1 is 1 or 2.

[0024] Additionally, the present specification provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound of Formula 1.

[0025] A compound according to one embodiment of the present specification is used in an organic light-emitting device to lower the driving voltage of the organic light-emitting device and improve light efficiency. In addition, the thermal stability of the compound can improve the lifespan characteristics of the device.

[0026] FIGS. 1 and FIGS. 2 illustrate examples of organic light-emitting devices according to one embodiment of the present specification.

[0027] [Explanation of the symbol]

[0028] 101: Board

[0029] 102: Anode

[0030] 103: Hole injection layer

[0031] 104: 1st Precision Transport Layer

[0032] 105: Second Precision Transport Layer

[0033] 106: Emissive layer

[0034] 107: Electron injection and transport layer

[0035] 108: Cathode

[0036] The present specification will be described in more detail below.

[0037] The above chemical formula 1 comprises heterocyclic groups of HAr1 and HAr2, and a 5-membered ring group including a nitrile group is connected to one or more of the heterocyclic groups, having LUMO orbital energies of -2.8 eV to -3.2 EV. Due to the energy barrier in the above range, when applied to a hole blocking layer, electron transport layer, electron injection layer, or electron injection and transport layer of an organic light-emitting diode, the compound of chemical formula 1 exhibits high efficiency characteristics.

[0038] Examples of substituents in this specification are described below, but are not limited thereto.

[0039] In this specification, dotted lines or refers to the connected part.

[0040] In this specification, Cn means n carbon atoms.

[0041] In this specification, “Cn-Cm” means “n to m carbon atoms” or “n to m carbon atoms”.

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

[0043] In this specification, the term “substituted or unsubstituted” means being substituted with one or more substituents selected from the group consisting of deuterium; halogen; nitrile group; alkyl group; silyl group; aryl group; aryloxy group; arylthio group; and heteroaryl group comprising one or more non-carbon atoms, being substituted with two or more of the exemplified substituents linked together, or having no substituents.

[0044] In this specification, the connection of two or more substituents means that a hydrogen of one substituent is connected to another substituent. For example, an isopropyl group and a phenyl group may be connected to become a substituent of an isopropylphenyl group or a phenylpropyl group.

[0045] In this specification, the connection of three substituents includes not only the connection of (substituent 1)-(substituent 2)-(substituent 3) in succession, but also the connection of (substituent 2) and (substituent 3) to (substituent 1). For example, two phenyl groups and isopropyl groups may be connected to form a (2-phenylpropane-2-yl)phenyl group or a 5-isopropyl-[1,1'-biphenyl]-2-yl group substituent. The same applies to the connection of four or more substituents as described above.

[0046] In one embodiment of the present specification, “substituted or unsubstituted” means being substituted with one or more substituents selected from the group consisting of deuterium; halogen; nitrile group; alkyl group; alkylsilyl group; arylsilyl group; aryl group; aryloxy group; arylthio group; and heteroaryl group, being substituted with a substituent connected to two or more substituents selected from said group, or having no substituents.

[0047] In one embodiment of the present specification, “substituted or unsubstituted” means being substituted with one or more substituents selected from the group consisting of deuterium; halogen; nitrile group; C1-C20 alkyl group; C6-C60 aryl group; and C2-C60 heteroaryl group, being substituted with a substituent connected to two or more substituents selected from said group, or having no substituents.

[0048] In one embodiment of the present specification, “substituted or unsubstituted” means being substituted with one or more substituents selected from the group consisting of deuterium; halogen; nitrile group; C1-C10 alkyl group; C6-C30 aryl group; and C2-C30 heteroaryl group, being substituted with a substituent connected to two or more substituents selected from said group, or having no substituents.

[0049] In this specification, examples of halogens include fluorine, chlorine, bromine, or iodine.

[0050] In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30; 1 to 20; 1 to 10; or 1 to 6. Specific examples include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl.

[0051] In this specification, an aryl group refers to a monovalent aromatic hydrocarbon or a derivative of an aromatic hydrocarbon. In this specification, an aromatic hydrocarbon refers to a compound comprising a planar ring in which pi electrons are fully conjugated, and a group derived from an aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed to an aromatic hydrocarbon. Furthermore, in this specification, an aryl group is intended to include a monovalent group in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are connected to each other. The aryl group is not particularly limited, but it is preferred to have 6 to 60 carbon atoms; 6 to 50; 6 to 30; 6 to 25; 6 to 20; 6 to 18; or 6 to 13 carbon atoms, and the aryl group may be monocyclic or polycyclic. Specifically, monocyclic aryl groups may include phenyl groups, biphenyl groups, terphenyl groups, quarterphenyl groups, etc., but are not limited thereto. Specifically, polycyclic aryl groups may include naphthyl groups, anthracenyl groups, phenanthryl groups, triphenyl groups, pyrenyl groups, perylenyl groups, chrysenyl groups, fluorenyl groups, etc., but are not limited thereto.

[0052] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

[0053] In this specification, when it is stated that a fluorenyl group may be substituted, the substituted fluorenyl group includes all compounds in which the substituents of the 5-membered ring of fluorene are spiro-bonded to each other to form an aromatic hydrocarbon ring. The substituted fluorenyl group includes, but is not limited to, 9,9'-spirobifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], etc.

[0054] In this specification, an aryloxy group is one in which an aryl group is connected to an oxygen atom, and an arylthio group is one in which an aryl group is connected to a sulfur atom. The aryl group of an aryloxy group is the same as the examples of aryl groups described above. Specifically, aryloxy groups include phenoxy groups, p-thoryloxy groups, m-thoryloxy groups, 3,5-dimethyl-phenoxy groups, 2,4,6-trimethylphenoxy groups, p-tert-butylphenoxy groups, 3-biphenyloxy groups, 4-biphenyloxy groups, 1-naphthyloxy groups, 2-naphthyloxy groups, 4-methyl-1-naphthyloxy groups, 5-methyl-2-naphthyloxy groups, 1-anthryloxy groups, 2-anthryloxy groups, 9-anthryloxy groups, 1-phenanthryloxy groups, 3-phenanthryloxy groups, 9-phenanthryloxy groups, etc., and arylthio groups include phenylthio groups, 2-methylphenylthio groups, 4-tert-butylphenylthio groups, etc., but are not limited thereto.

[0055] In the present specification, the heterocyclic group comprises one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may comprise one or more atoms selected from the group consisting of O, N, Si, and S, etc. The number of carbon atoms is not particularly limited, but it is preferred to be 2 to 60; 2 to 50; 2 to 30; 2 to 20; 2 to 18; or 2 to 13 carbon atoms. Examples of heterocyclic groups include thiophene group, furanyl group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group, pyridazine group, pyrazine group, quinoline group, quinazolin group, quinoxaline group, phthalazine group, cinnoline group, pyridopyrimidine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophen group, dibenzothiophen group, benzonaphthiophen group, benzofuran group, dibenzofuran group, naphthobenzofuran group. There are, but are not limited to, phenanthroline, thiazole, isooxazole, oxadiazole, thiadiazole, benzothiazole, phenothiazine, dibenzofuran, dihydrophenothiazine, dihydrobenzisoquinoline, and chromene groups.

[0056] In the present specification, the heterocyclic group may be a monocyclic or polycyclic group, may be an aromatic, aliphatic, or an aromatic and aliphatic condensation ring, and may be selected from examples of the heterocyclic group.

[0057] In this specification, a heteroaryl group refers to a monovalent aromatic heterocycle. Here, an aromatic heterocycle refers to a monovalent group of an aromatic ring or a derivative of an aromatic ring, which includes one or more heteroatoms among O, N, Si, and S in the ring. The derivative of the aromatic ring includes all structures in which an aromatic ring or an aliphatic ring is condensed to an aromatic ring. Furthermore, in this specification, the heteroaryl group is intended to include a monovalent group in which an aromatic ring containing two or more heteroatoms or a derivative of an aromatic ring containing heteroatoms is connected to one another. It is preferable that the number of carbon atoms of the heteroaryl group be 2 to 50; 2 to 30; 2 to 20; 2 to 18; or 2 to 13.

[0058] In this specification, an arylene group refers to a group having two binding sites to an aryl group, i.e., a divalent group. Except for the fact that each of these is a divalent group, the description of the aryl group described above may apply.

[0059] In this specification, a heteroarylene group refers to a heteroaryl group having two binding sites, i.e., a divalent group. Except for the fact that each of these is a divalent group, the description of the heteroaryl group described above may apply.

[0060] The compound of Chemical Formula 1 below will be described in detail below.

[0061] [Chemical Formula 1]

[0062]

[0063] In one embodiment of the present specification, HAr1 and HAr2 are identical or different from each other, and are each independently substituted or unsubstituted, and are heterocyclic rings comprising two or more heteroatoms selected from the group consisting of N, O and S.

[0064] In one embodiment of the present specification, HAr1 and HAr2 are identical or different from each other and each independently comprises two or more heteroatoms selected from the group consisting of N, O, and S, wherein the heterocyclic group comprises one or more N, and HAr is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, alkyl groups, aryl groups, and heterocyclic groups, or with a substituent connected to two or more groups selected from said group.

[0065] In one embodiment of the present specification, HAr1 and HAr2 are identical or different from each other and each independently comprises a five-membered ring or a six-membered ring comprising two or more heteroatoms, and the five-membered ring or the six-membered ring is connected to L1.

[0066] In one embodiment of the present specification, HAr1 and HAr2 are identical or different from each other and each independently comprises a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted pyridazine group; a substituted or unsubstituted pyrazine group; a substituted or unsubstituted triazine group; a substituted or unsubstituted tetrazine group; a substituted or unsubstituted quinazolin group; a substituted or unsubstituted quinoxaline group; a substituted or unsubstituted cinnoline group; a substituted or unsubstituted phthalazine group; a substituted or unsubstituted benzofuropyrimidine group; a substituted or unsubstituted benzothienopyrimidine group; a substituted or unsubstituted benzofuropyridazine group; a substituted or unsubstituted benzothienopyridazine group; a substituted or unsubstituted benzofuropyridazine group; a substituted or unsubstituted benzothienopyridazine group; a substituted or unsubstituted benzofurotriazine group; a substituted or unsubstituted benzothienotriazine group; a substituted or unsubstituted benzothienotriazine group; It is a substituted or unsubstituted benzofurotetrazine group; a substituted or unsubstituted benzothienotetrezine group; a substituted or unsubstituted imidazole group; a substituted or unsubstituted oxazole group; a substituted or unsubstituted thiazole group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted benzoxazole group; or a substituted or unsubstituted benzothiazole group.

[0067] In one embodiment of the present specification, HAr1 and HAr2 are identical or different from each other and are each independently substituted or unsubstituted with R2 or Formula 2 described below.

[0068] In one embodiment of the present specification, HAr1 and HAr2 are homogeneous substituents except for R2 or a substituent of Formula 2. For example, HAr1 and HAr2 are triazine groups, but the substituents connected to (substituting) HAr1 and HAr2 may be the same or different from each other.

[0069] In one embodiment of the present specification, HAr1 and HAr2 are heterogeneous substituents.

[0070] In one embodiment of the present specification, one or more of HAr1 and HAr2 are substituted with the following chemical formula 2.

[0071] [Chemical Formula 2]

[0072]

[0073] In the above chemical formula 2,

[0074] Z1 is O; or S, and

[0075] L3 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0076] R1 is hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted aryl group; substituted or unsubstituted aryloxy group; substituted or unsubstituted arylthio group; or substituted or unsubstituted heteroaryl group, and

[0077] n3 is an integer from 0 to 5, and if it is 2 or greater, L3 are identical or different from each other, and

[0078] m1 is an integer from 1 to 3, and

[0079] r1 is an integer from 0 to 2, and when r1 is 2, R1 are the same or different.

[0080] In one embodiment of the present specification, the HAr1 comprises the chemical formula 2 as a substituent.

[0081] In one embodiment of the present specification, the HAr2 comprises the chemical formula 2 as a substituent.

[0082] In one embodiment of the present specification, HAr1 and HAr2 are identical or different from each other and are each independently of the following chemical formula 101 or 201.

[0083] [Chemical Formula 101]

[0084]

[0085] [Chemical Formula 201]

[0086]

[0087] In the above chemical formulas 101 and 201,

[0088] X1 to X6 are identical or different from each other, and each is independently a heteroatom of N; or CR2, and

[0089] Y1 is a heteroatom selected from the group consisting of NR2, O, and S; or CR22, and

[0090] Y2 to Y5 are identical or different from each other, and each is independently a heteroatom of N; or CR2, and

[0091] At least two of X1 to X6 are the above heteroatoms, and

[0092] At least two of Y1 to Y5 are the above heteroatoms, and

[0093] One of R2 is connected to the above Formula 1, and the remainders are identical or different from one another, each independently hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted aryl group; substituted or unsubstituted aryloxy group; substituted or unsubstituted arylthio group; substituted or unsubstituted heteroaryl group; or the above Formula 2, or are combined with adjacent substituents to form a substituted or unsubstituted ring, and

[0094] In at least one of the above HAr1 and HAr2, 1 or more R2 is the above chemical formula 2.

[0095] In one embodiment of the present specification, HAr1 is the formula 101, and one or more of the R2 of HAr1 are the formula 2.

[0096] In one embodiment of the present specification, HAr1 is the formula 201, and one or more of the R2 of HAr1 are the formula 2.

[0097] In one embodiment of the present specification, the HAr2 is the formula 101, and one or more of the R2 of the HAr2 are the formula 2.

[0098] In one embodiment of the present specification, the HAr2 is the formula 201, and one or more of the R2 of the HAr2 are the formula 2.

[0099] In one embodiment of the present specification, 2 to 5 of X1 to X6 are heteroatoms, and the remainder is CR2.

[0100] In one embodiment of the present specification, 2 to 4 of X1 to X6 are heteroatoms, and the remainder is CR2.

[0101] In one embodiment of the present specification, two or three of X1 to X6 are heteroatoms, and the remainder is CR2.

[0102] In one embodiment of the present specification, the heteroatoms among X1 to X6 include one or more N.

[0103] In one embodiment of the present specification, 2 to 4 of Y1 to Y5 are heteroatoms, and the remainder is CR2 or CR22.

[0104] In one embodiment of the present specification, two or three of Y1 to Y5 are heteroatoms, and the remainder is CR2 or CR22.

[0105] In one embodiment of the present specification, the heteroatoms among Y1 to Y5 include one or more N.

[0106] In one embodiment of the present specification, one of R2 is connected to Formula 1, and the others are identical or different from one another, each independently hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted aryl group; substituted or unsubstituted aryloxy group; substituted or unsubstituted arylthio group; substituted or unsubstituted heteroaryl group; or Formula 2, or are combined with adjacent substituents to form a substituted or unsubstituted ring.

[0107] In one embodiment of the present specification, one of the R2s is connected to Formula 1, and the others are identical or different from one another, each independently hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or Formula 2, or is combined with an adjacent R2 to form a substituted or unsubstituted single to triple ring.

[0108] In one embodiment of the present specification, when two or more R2s are combined to form a ring, the ring is substituted or not substituted with R2.

[0109] In one embodiment of the present specification, when two or more R2s combine to form a ring, the ring is a benzene ring, a benzofuran ring, or a benzothiophene ring.

[0110] In one embodiment of the present specification, one of R2 is connected to the above formula 1, another is the above formula 2, and one or more of the remainder are substituents that are not hydrogen or deuterium.

[0111] In one embodiment of the present specification, one of R2 is connected to the above formula 1, another is the above formula 2, and one to four of the remainder are substituents that are not hydrogen or deuterium.

[0112] In one embodiment of the present specification, one of R2 is connected to the above formula 1, another is the above formula 2, and one to three of the remainder are substituents that are not hydrogen or deuterium.

[0113] In one embodiment of the present specification, one of R2 is connected to the above formula 1, another is the above formula 2, and one or more of the remainder are substituents that are not hydrogen or deuterium.

[0114] In one embodiment of the present specification, one of the R2s is connected to Formula 1, and the others are identical or different from one another, each independently hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; or Formula 2, or is combined with an adjacent R2 to form a substituted or unsubstituted monocyclic or bicyclic aromatic ring.

[0115] In one embodiment of the present specification, one of the R2s is connected to Formula 1, and the others are identical or different from one another, each independently hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted C1-C10 alkyl group; substituted or unsubstituted C6-C30 aryl group; substituted or unsubstituted C2-C30 heteroaryl group; or Formula 2, or is combined with an adjacent R2 to form a substituted or unsubstituted monocyclic or bicyclic aromatic ring.

[0116] In one embodiment of the present specification, one of the R2s is connected to Formula 1, and the others are identical or different from one another, each independently hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted C1-C6 alkyl group; substituted or unsubstituted C6-C20 aryl group; substituted or unsubstituted C2-C20 heteroaryl group; or Formula 2, or is combined with an adjacent R2 to form a substituted or unsubstituted monocyclic or bicyclic aromatic ring.

[0117] In one embodiment of the present specification, one of the R2s is connected to Formula 1, and the others are identical or different from one another, each independently hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted methyl group; substituted or unsubstituted ethyl group; substituted or unsubstituted propyl group; substituted or unsubstituted butyl group; substituted or unsubstituted phenyl group; substituted or unsubstituted biphenyl group; substituted or unsubstituted terphenyl group; substituted or unsubstituted quadrphenyl group; substituted or unsubstituted naphthyl group; substituted or unsubstituted fluorene group; substituted or unsubstituted anthracene group; substituted or unsubstituted phenanthrene group; substituted or unsubstituted fluoranthen group; substituted or unsubstituted spirobifluorene group; or Formula 2, or is combined with an adjacent R2 to form a substituted or unsubstituted single to triple ring.

[0118] In one embodiment of the present specification, one of the R2s is connected to Formula 1, and the others are identical or different from one another, each independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted isopropyl group; a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted naphthyl-phenyl group; a substituted or unsubstituted phenyl-naphthyl group; a substituted or unsubstituted phenanthrene group; or Formula 2, or is combined with an adjacent R2 to form a substituted or unsubstituted single to triple ring.

[0119] In one embodiment of the present specification, one of R2 is connected to Formula 1, and the others are identical or different from one another and are each independently hydrogen; deuterium; a C1-C20 alkyl group; a C6-C60 aryl group; a C2-C60 heteroaryl group; or Formula 2, and the substituent of R2 is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; a nitrile group; a C1-C20 alkyl group; a C6-C60 aryl group; and a C2-C60 heteroaryl group, or with a substituent connected to two or more groups selected from said group.

[0120] In one embodiment of the present specification, one of R2 is connected to Formula 1, and the others are identical or different from one another and are each independently hydrogen; deuterium; methyl group; ethyl group; propyl group; butyl group; phenyl group; biphenyl group; terphenyl group; naphthyl group; phenanthrene group; or Formula 2, and the substituent of R2 is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; nitrile group; C1-C20 alkyl group; C6-C60 aryl group; and C2-C60 heteroaryl group, or with a substituent connected to two or more groups selected from said group.

[0121] In one embodiment of the present specification, the formula 101 is one of the following formulas 102 to 104.

[0122] [Chemical Formula 102]

[0123]

[0124] [Chemical Formula 103]

[0125]

[0126] [Chemical Formula 104]

[0127]

[0128] In the above chemical formulas 102 to 104,

[0129] X1 to X6 are as defined in the above chemical formula 101, and

[0130] One of R2 is connected to the above Formula 1, and the remainders are identical or different from one another, and each independently hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or the above Formula 2, and

[0131] Z2 is O; S; or NR3, and

[0132] R3 is hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or the above formula 2,

[0133] r3 is an integer from 0 to 4, and if it is 2 or greater, R3 are the same or different from each other.

[0134] In one embodiment of the present specification, Z2 is O; or S.

[0135] In one embodiment of the present specification, R3 is identical to the definition of the substituent of R2.

[0136] In one embodiment of the present specification, R3 is hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; or the formula 2.

[0137] In one embodiment of the present specification, R3 is hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted C1-C10 alkyl group; substituted or unsubstituted C6-C30 aryl group; substituted or unsubstituted C2-C30 heteroaryl group; or the formula 2.

[0138] In one embodiment of the present specification, R3 comprises hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted methyl group; substituted or unsubstituted ethyl group; substituted or unsubstituted propyl group; substituted or unsubstituted butyl group; substituted or unsubstituted phenyl group; substituted or unsubstituted biphenyl group; substituted or unsubstituted terphenyl group; substituted or unsubstituted tetraphenyl group; substituted or unsubstituted naphthyl group; substituted or unsubstituted fluorene group; substituted or unsubstituted anthracene group; substituted or unsubstituted phenanthrene group; substituted or unsubstituted fluoranthene group; substituted or unsubstituted furan group; substituted or unsubstituted thiophene group; substituted or unsubstituted benzofuran group; substituted or unsubstituted benzothiophene group; substituted or unsubstituted dibenzofuran group; substituted or unsubstituted dibenzothiophene group; substituted or unsubstituted carbazole group; Substituted or unsubstituted spiro[fluorene-xanthen] group; substituted or unsubstituted spiro[fluorene-thioxanthen] group; substituted or unsubstituted spiro[benzoflurene-xanthen] group; substituted or unsubstituted spiro[benzoflurene-thioxanthen] group; substituted or unsubstituted spiro[benzoflurene-fluorene] group; substituted or unsubstituted spiro[benzothioxanthen-fluorene] group; or the above chemical formula 2.

[0139] In one embodiment of the present specification, R3 is hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted isopropyl group; a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted naphthyl-phenyl group; a substituted or unsubstituted phenyl-naphthyl group; a substituted or unsubstituted phenanthrene group; or the formula 2.

[0140] In one embodiment of the present specification, R3 is hydrogen; deuterium; phenyl group; biphenyl group; naphthyl group; phenanthrene group; or the formula 2 above, and R3 is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, C6-C30 aryl groups and C2-C30 heteroaryl groups, or with a substituent connected to two or more groups selected from the group.

[0141] In one embodiment of the present specification, the formula 102 is one of the following formulas 111 to 119.

[0142] [Chemical Formula 111]

[0143]

[0144] [Chemical Formula 112]

[0145]

[0146] [Chemical Formula 113]

[0147]

[0148] [Chemical Formula 114]

[0149]

[0150] [Chemical Formula 115]

[0151]

[0152] [Chemical Formula 116]

[0153]

[0154] [Chemical Formula 117]

[0155]

[0156] [Chemical Formula 118]

[0157]

[0158] [Chemical Formula 119]

[0159]

[0160] In the above chemical formulas 111 to 119,

[0161] R2 is as defined in the above chemical formula 102, and

[0162] The dotted line is connected to the above chemical formula 1, and

[0163] r21 is an integer from 0 to 3, and

[0164] r22 is an integer from 0 to 2, and

[0165] r23 is 0 or 1, and

[0166] If r21 is 2 or greater, or r22 is 2, then R2 are the same or different.

[0167] In one embodiment of the present specification, the formula 103 is the following formula 121 or 122.

[0168] [Chemical Formula 121]

[0169]

[0170] [Chemical Formula 122]

[0171]

[0172] In the above chemical formulas 121 and 122,

[0173] Z2, R2, and R3 are as defined in the above chemical formula 103, and

[0174] The dotted line is connected to the above chemical formula 1, and

[0175] r23 is 0 or 1.

[0176] In one embodiment of the present specification, the above chemical formula 104 is the following chemical formula 123.

[0177] [Chemical Formula 123]

[0178]

[0179] In the above chemical formula 123,

[0180] R2 and R3 are as defined in the above chemical formula 104, and

[0181] The dotted line is connected to the above chemical formula 1, and

[0182] r23 is 0 or 1.

[0183] In one embodiment of the present specification, the formula 201 is the following formula 202 or 203.

[0184] [Chemical Formula 202]

[0185]

[0186] [Chemical Formula 203]

[0187]

[0188] In the above chemical formulas 202 and 203,

[0189] Y1 to Y5 are as defined in the above chemical formula 201, and

[0190] One of R2 is connected to the above Formula 1, and the remainders are identical or different from one another, and each independently hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or the above Formula 2, and

[0191] R3 is hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or the above formula 2,

[0192] r3 is an integer from 0 to 4, and if it is 2 or greater, R3 are the same or different from each other.

[0193] R2 and R3 are as described above.

[0194] In one embodiment of the present specification, the formula 202 is the following formula 211.

[0195] [Chemical Formula 211]

[0196]

[0197] In the above chemical formula 211,

[0198] The dotted line is connected to the above chemical formula 1, and

[0199] Y1 is a heteroatom selected from the group consisting of NR2, O, and S.

[0200] In one embodiment of the present specification, the formula 203 is one of the following formulas 212 to 214.

[0201] [Chemical Formula 212]

[0202]

[0203] [Chemical Formula 213]

[0204]

[0205] [Chemical Formula 214]

[0206]

[0207] In the above chemical formulas 212 to 214,

[0208] R2 and R3 are as defined in the above chemical formula 203, and

[0209] The dotted line is connected to the above chemical formula 1, and

[0210] Y1 is a heteroatom selected from the group consisting of O and S.

[0211] The definition of R2 in the above chemical formulas 111 to 119, 121 to 123, and 211 to 214 is the same as the definition of the substituent R2 in chemical formulas 101 and 201, except that one is connected to the above chemical formula 1.

[0212] In one embodiment of the present specification, L1 and L2 are identical or different from each other and are each independently substituted or unsubstituted arylene groups; or substituted or unsubstituted heteroarylene groups.

[0213] In one embodiment of the present specification, L1 and L2 are identical or different from each other and are each independently substituted or unsubstituted C6-C60 arylene groups; or substituted or unsubstituted C2-C60 heteroarylene groups.

[0214] In one embodiment of the present specification, L1 and L2 are identical or different from each other and are each independently substituted or unsubstituted C6-C30 arylene groups; or substituted or unsubstituted C2-C30 heteroarylene groups.

[0215] In one embodiment of the present specification, L1 and L2 are identical or different from each other and are each independently substituted or unsubstituted C6-C20 arylene groups; or substituted or unsubstituted C2-C20 heteroarylene groups.

[0216] In one embodiment of the present specification, L1 and L2 are identical or different from each other and are each independently a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted tetraphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted fluorenylene group; a substituted or unsubstituted anthracenylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted fluoranthenylene group; or a substituted or unsubstituted spirobifluorenylene group.

[0217] In one embodiment of the present specification, L1 to L3 are identical or different from each other and are each independently selected from the following structures.

[0218]

[0219] The above structure is substituted or unsubstituted with deuterium, and

[0220] The dotted line is connected to the above chemical formula 1, and

[0221] Z3 is O; S; NR4; or CR42, and

[0222] R4 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0223] In one embodiment of the present specification, R4 is hydrogen; deuterium; a substituted or unsubstituted C1-C10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

[0224] In one embodiment of the present specification, R4 is a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0225] In one embodiment of the present specification, one or more of L1 and L2 are selected from the following structures.

[0226]

[0227]

[0228] The above structure is substituted or unsubstituted with deuterium.

[0229] In one embodiment of the present specification, when there are multiple L1 or L2, at least one of the multiple L1 or L2 is selected from the structure.

[0230] In one embodiment of the present specification, L1 and L2 are different from each other. For example, even if L1 and L2 are substituted or unsubstituted phenylene groups, L1 and L2 may be different from each other if their connection positions are different.

[0231] In one embodiment of the present specification, L1 and L2 are identical or different from each other and are each independently a phenylene group; a phenylene group substituted with a phenanthrene group; a biphenylene group; a terphenylene group; a naphthylene group; or a phenylene-naphthylene group, and L1 and L2 are substituted or unsubstituted with deuterium.

[0232] In one embodiment of the present specification, Z1 is O; or S.

[0233] In one embodiment of the present specification, L3 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

[0234] In one embodiment of the present specification, L3 is a direct bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group.

[0235] In one embodiment of the present specification, L3 is a direct bond; a substituted or unsubstituted C6-C30 arylene group; or a substituted or unsubstituted C2-C30 heteroarylene group.

[0236] In one embodiment of the present specification, L3 is a direct bond; a substituted or unsubstituted C6-C20 arylene group; or a substituted or unsubstituted C2-C20 heteroarylene group.

[0237] In one embodiment of the present specification, L3 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted phenylene-naphthylene group.

[0238] In one embodiment of the present specification, L3 is selected from a direct coupling or the following structure.

[0239]

[0240]

[0241] The above structure is substituted or unsubstituted with deuterium.

[0242] In one embodiment of the present specification, R1 is hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group.

[0243] In one embodiment of the present specification, R1 is hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C6-C60 aryl group; or substituted or unsubstituted C2-C60 heteroaryl group.

[0244] In one embodiment of the present specification, R1 is hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted C1-C10 alkyl group; substituted or unsubstituted C6-C30 aryl group; or substituted or unsubstituted C2-C30 heteroaryl group.

[0245] In one embodiment of the present specification, R1 is hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted C1-C6 alkyl group; substituted or unsubstituted C6-C20 aryl group; or substituted or unsubstituted C2-C20 heteroaryl group.

[0246] In one embodiment of the present specification, R1 is hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted methyl group; substituted or unsubstituted ethyl group; substituted or unsubstituted propyl group; substituted or unsubstituted butyl group; substituted or unsubstituted phenyl group; substituted or unsubstituted biphenyl group; substituted or unsubstituted terphenyl group; substituted or unsubstituted tetraphenyl group; substituted or unsubstituted naphthyl group; substituted or unsubstituted phenyl-naphthyl group; or substituted or unsubstituted naphthyl-phenyl group.

[0247] In one embodiment of the present specification, R1 is hydrogen; deuterium; a methyl group; or a phenyl group, and R1 is substituted with or unsubstituted with deuterium.

[0248] In one embodiment of the present specification, R1 is hydrogen; or deuterium.

[0249] In one embodiment of the present specification, m1 is an integer from 1 to 3.

[0250] In one embodiment of the present specification, m1 is 1 or 2.

[0251] In one embodiment of the present specification, r1 is 1 or 2.

[0252] In one embodiment of the present specification, m1+r1 is an integer from 1 to 3.

[0253] In one embodiment of the present specification, the formula 2 is selected from the following structures.

[0254]

[0255] In the above structure,

[0256] Z1, L3, n3, R1 and r1 are as defined in Chemical Formula 2 above, and

[0257] The dotted line is connected to the above chemical formula 1, and

[0258] r11 is 0 or 1.

[0259] In one embodiment of the present specification, n1 and n2 are identical or different from each other and are each independently integers from 1 to 5, and if n2 is 2 or more, L1 and L2 are identical or different from each other.

[0260] In one embodiment of the present specification, n1 and n2 are integers from 1 to 3.

[0261] In one embodiment of the present specification, n1 and n2 are 1 or 2.

[0262] In one embodiment of the present specification, n1+n2 is 5 or less.

[0263] In one embodiment of the present specification, n1+n2 is 4 or less.

[0264] In one embodiment of the present specification, n1+n2 is 3 or less.

[0265] In one embodiment of the present specification, HAr1 and HAr2 are identical or different from each other and each independently comprises two or more heteroatoms selected from the group consisting of N, O, and S, wherein HAr1 and HAr2 are heterocyclic groups comprising one or more N, and HAr1 and HAr2 are substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, alkyl groups, and aryl groups, or with substituents connected to two or more groups selected from said group.

[0266] The above L1 and L2 are identical or different from each other and are each independently arylene groups, and the above L1 and L2 are substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, alkyl groups, and aryl groups, or with substituents connected to two or more groups selected from said group.

[0267] The above L3 is a direct bond; or an arylene group, and the above L3 is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, alkyl groups, and aryl groups, or with a substituent connected to two or more groups selected from said group, and

[0268] The above R1 is hydrogen; deuterium; an alkyl group; or an aryl group, and the above R1 is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, and an aryl group, or with a substituent connected to two or more groups selected from said group.

[0269] The number of carbon atoms in the alkyl group is 1 to 30, the number of carbon atoms in the aryl and arylene groups is 6 to 60, and the number of carbon atoms in the heterocyclic group is 2 to 60.

[0270] In one embodiment of the present specification, the compound of Formula 1 is selected from any one of the following compounds.

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278] A compound according to one embodiment of this specification may be prepared by the manufacturing method described below. If necessary, substituents may be added or excluded, and the positions of the substituents may be changed. Additionally, starting materials, reactants, reaction conditions, etc., may be changed based on techniques known in the art.

[0279] For example, the compound of Formula 1 can be synthesized through a Suzuki coupling reaction. It is preferable to perform this in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be modified as known in the art. The above manufacturing method can be further specified in the manufacturing examples described below.

[0280] The present specification provides an organic light-emitting device comprising the aforementioned compound.

[0281] The present specification provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound of Formula 1.

[0282] In this specification, when it is stated that a component is located "on" another component, this includes not only cases where a component is in contact with another component, but also cases where another component exists between the two components.

[0283] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0284] In this specification, the term "layer" is used in a sense compatible with "film" commonly used in the art and refers to a coating that covers a desired area. The size of the "layer" is not limited, and each "layer" may have the same or different size. In one embodiment, the size of the "layer" may be equal to the size of the entire device, correspond to the size of a specific functional area, or be as small as a single subpixel.

[0285] In the present specification, the meaning of a specific A substance being included in a B layer includes both i) one or more types of A substances being included in a single B layer and ii) the B layer being composed of one or more layers and A substance being included in one or more of the multilayer B layers.

[0286] In the present specification, the meaning that a specific A material is included in a C layer or a D layer is that it is included in at least one of the C layers, ii) included in at least one of the D layers, or iii) included in each of the C layers and the D layers.

[0287] The organic layer of the organic light-emitting device of the present specification may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0288] In one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a compound of Formula 1.

[0289] In one embodiment of the present specification, the organic layer comprises an electron injection layer, an electron transport layer, an electron injection and transport layer, or a hole blocking layer, and the electron injection layer, electron transport layer, electron injection and transport layer, or hole blocking layer comprises a compound of Formula 1.

[0290] In one embodiment of the present specification, the electron injection layer, electron transport layer, electron injection and transport layer or hole blocking layer further comprises an n-type dopant.

[0291] The above n-type dopant may be one or more selected from alkali metals and alkaline earth metals.

[0292] When organoalkali metal compounds or organoalkali earth metal compounds are used as n-type dopants, stability regarding holes in the emissive layer can be secured, thereby improving the lifespan of the organic light-emitting device. Additionally, by controlling the ratio of organoalkali metal compounds or organoalkali earth metal compounds to the electron transport layer, the balance between holes and electrons in the emissive layer can be maximized, thereby increasing luminous efficiency.

[0293] According to one embodiment of the present specification, the n-type dopant is 8-hydroxyquinolinate lithium, bis(8-hydroxyquinolinate)zinc, bis(8-hydroxyquinolinate)copper, bis(8-hydroxyquinolinate)manganese, tris(8-hydroxyquinolinate)aluminum, tris(2-methyl-8-hydroxyquinolinate)aluminum, tris(8-hydroxyquinolinate)gallium, bis(10-hydroxybenzo[h]quinolinate)beryllium, bis(10-hydroxybenzo[h]quinolinate)zinc, bis(2-methyl-8-quinolinate)chlorogallium, bis(2-methyl-8-quinolinate)(o-cresolato)gallium, Examples include bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, but are not limited thereto. According to one embodiment, LiQ is more preferred as the n-type dopant.

[0294] The electron injection layer, electron transport layer, electron injection and transport layer, or hole blocking layer may comprise the compound of Formula 1 and the n-type dopant in a weight ratio of 1:9 to 9:1. Preferably, the heterocyclic compound of Formula 1 and the n-type dopant may comprise 2:8 to 8:2, and more preferably 3:7 to 7:3.

[0295] In one embodiment of the present specification, the organic layer further comprises one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0296] In one embodiment of the present specification, the organic light-emitting element comprises: a first electrode; a second electrode provided opposite to the first electrode; a light-emitting layer provided between the first electrode and the second electrode; and one or more organic layers provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0297] In one embodiment of the present specification, the organic layer comprising one or more layers further comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

[0298] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0299] In one embodiment of the present specification, the second electrode is a negative electrode and the second electrode is a positive electrode.

[0300] In one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device of a normal type structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0301] In one embodiment of the present specification, the organic light-emitting device may be an inverted type organic light-emitting device in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0302] For example, the structure of an organic light-emitting device according to one embodiment of the present specification is illustrated in FIGS. 1 and 2. FIGS. 1 and 2 illustrate an organic light-emitting device and are not limited thereto.

[0303] FIG. 1 illustrates the structure of an organic light-emitting device in which an anode (102), a light-emitting layer (106), and a cathode (108) are sequentially stacked on a substrate (101). The compound of Formula 1 is included in the light-emitting layer.

[0304] FIG. 2 illustrates the structure of an organic light-emitting device in which an anode (102), a hole injection layer (103), a first hole transport layer (104), a second hole transport layer (105), a light-emitting layer (106), an electron injection and transport layer (107), and a cathode (108) are sequentially stacked on a substrate (101). According to one embodiment of the present specification, the compound of Formula 1 is included in the electron injection and transport layer (107).

[0305] The organic light-emitting device of this specification can be manufactured using materials and methods known in the art, except that the light-emitting layer comprises the said compound.

[0306] When the above organic light-emitting element includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0307] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, the device can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation, forming an organic layer including a hole injection layer, a hole transport layer, an emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to such a method, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0308] In addition, the compound of Chemical Formula 1 can be formed as an organic layer by vacuum deposition as well as by solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

[0309] In addition to this method, an organic light-emitting diode can also be fabricated by sequentially depositing an organic layer and an anode material from a cathode material onto a substrate. However, the manufacturing method is not limited to this.

[0310] As the anode material, a material with a large work function is generally preferred to facilitate hole injection into the organic layer. Examples include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metal and oxide such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0311] The above-mentioned cathode material is preferably a material with a small work function to facilitate electron injection into an organic layer. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0312] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material may include condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0313] According to one embodiment of the present specification, the host comprises a compound represented by the following chemical formula H-1, but is not limited thereto.

[0314] [Chemical Formula H-1]

[0315]

[0316] In the above chemical formula H-1,

[0317] L20 and L21 are identical or different from each other, and each is independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group, and

[0318] Ar20 and Ar21 are identical or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0319] R2O1 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0320] r201 is an integer from 1 to 8, and if r201 is 2 or more, the 2 or more R201s are the same or different from each other.

[0321] In one embodiment of the present specification, L20 and L21 are identical or different from each other and are each independently directly bonded; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

[0322] In one embodiment of the present specification, L20 and L21 are identical or different from each other and are each independently directly bonded; a phenylene group substituted or unsubstituted with deuterium; a biphenylylene group substituted or unsubstituted with deuterium; a naphthylene group substituted or unsubstituted with deuterium; a dibenzofuran group; or a dibenzothiophene group.

[0323] In one embodiment of the present specification, Ar20 and Ar21 are identical or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; or substituted or unsubstituted monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms.

[0324] In one embodiment of the present specification, Ar20 and Ar21 are identical or different from each other and each independently comprises: a phenyl group substituted or unsubstituted with a deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group substituted or unsubstituted with a deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; and a dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms. Or it is a naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0325] In one embodiment of the present specification, the Ar20 and Ar21 are identical or different from each other and are each independently a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group; a naphthyl group substituted or unsubstituted with deuterium; a thiophene group substituted or unsubstituted with a phenyl group; a phenanthrene group; a dibenzofuran group; a naphthobenzofuran group; a dibenzothiophen group; or a naphthobenzothiophen group.

[0326] In one embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[0327] According to one embodiment of the present specification, the R201 is hydrogen; or a phenyl group.

[0328] According to one embodiment of the present specification, the formula H-1 is represented by the following compound.

[0329]

[0330] The above dopant materials include aromatic amine derivatives, styramine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and periplantene having arylamine groups. In addition, styramine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, wherein one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamine groups are substituted or unsubstituted. Specifically, styramine, styryldiamine, styryltriamine, styryltetraamine, etc. are examples, but are not limited thereto. In addition, metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0331] According to one embodiment of the present specification, the dopant comprises a compound represented by the following chemical formula D-1, but is not limited thereto.

[0332] [Chemical Formula D-1]

[0333]

[0334] In the above chemical formula D-1,

[0335] T1 to T6 are the same or different from one another, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkylsilyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0336] t5 and t6 are integers from 1 to 4, respectively, and

[0337] If the above t5 is 2 or more, the above 2 or more T5s are the same or different from each other, and

[0338] If the above t6 is 2 or more, the above 2 or more T6s are the same or different from each other.

[0339] According to one embodiment of the present specification, T1 to T6 are the same or different from each other and are each independently hydrogen; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted straight-chain or branched-chain alkylsilyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0340] According to one embodiment of the present specification, T1 to T6 are the same or different from each other and are each independently hydrogen; a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a straight-chain or branched-chain alkylsilyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, a cyano group, or a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0341] According to one embodiment of the present specification, T1 to T6 are the same or different from each other and are each independently a phenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of hydrogen; methyl group; ethyl group; isopropyl group; trimethylsilyl group; or deuterium, nitrile group, methyl group, ethyl group, isopropyl group, and trimethylsilyl group, or a substituent connected to a group selected from said group.

[0342] According to one embodiment of the present specification, the formula D-1 is represented by the following compound.

[0343]

[0344] The hole injection layer described above is a layer that receives holes from the electrode. It is desirable for the hole injection material to have the ability to transport holes, thereby having an excellent hole receiving effect from the anode and an excellent hole injection effect on the emitting layer or emitting material. In addition, it is desirable for the material to have an excellent ability to prevent the movement of excitons generated in the emitting layer to the electron injection layer or electron injection material. In addition, it is desirable for the material to have an excellent thin film formation ability. Furthermore, it is desirable for the HOMO (highest occupied molecular orbital) of the hole injection material to be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic materials; hexanitrile-hexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; and polythiophene-based conductive polymers such as anthraquinone and polyaniline.

[0345] According to one embodiment of the present specification, the hole injection layer comprises a compound represented by the following chemical formula HI-1, but is not limited thereto.

[0346] [Chemical Formula HI-1]

[0347]

[0348] In the above chemical formula HI-1,

[0349] R301 to R306 are the same or different from one another and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group, and

[0350] L301 and L302 are the same or different from each other and are each independently directly bonded; substituted or unsubstituted arylene groups; or substituted or unsubstituted divalent heterocyclic groups.

[0351] According to the present specification, R301 and R302 are the same or different from each other and are each independently straight-chain or branched-chain alkyl groups having 1 to 30 carbon atoms.

[0352] According to one embodiment of the present specification, R301 and R302 are methyl groups.

[0353] According to one embodiment of the present specification, L301 and L302 are directly coupled.

[0354] According to one embodiment of the present specification, R303 to R306 are the same or different from one another and are each independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heterocyclic groups.

[0355] According to one embodiment of the present specification, R303 to R306 are the same or different from each other and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0356] According to one embodiment of the present specification, R303 to R306 are the same or different from each other and are each independently a phenyl group; or a carbazole group substituted or unsubstituted with a phenyl group.

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

[0358]

[0359] The hole transport layer described above is a layer that receives holes from the hole injection layer and transports them to the emissive layer. As for the hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the emissive layer, and a material with high mobility for holes, is preferred. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited thereto. Additionally, the hole transport layer may have a multilayer structure. For example, it may include a first hole transport layer and a second hole transport layer.

[0360] According to one embodiment of the present specification, the hole transport layer comprises a compound represented by the following chemical formula HT-1, but is not limited thereto.

[0361] [Chemical Formula HT-1]

[0362]

[0363] In the above chemical formula HT-1,

[0364] At least one of X'1 to X'6 is N, and the rest are CH, and

[0365] R309 to R314 are the same or different from each other and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0366] According to one embodiment of the present specification, X'1 to X'6 are N.

[0367] According to one embodiment of the present specification, R309 to R314 are cyano groups.

[0368] According to one embodiment of the present specification, the chemical formula HT-1 is represented by the following compound.

[0369]

[0370] According to one embodiment of the present specification, the hole transport layer comprises a compound represented by the following chemical formula HT-2, but is not limited thereto.

[0371] [Chemical Formula HT-2]

[0372]

[0373] In the above chemical formula HT-2,

[0374] R315 to R317 are the same or different from one another and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring, and

[0375] r315 is an integer from 1 to 5, and if r315 is 2 or more, the 2 or more R315s are the same or different from each other,

[0376] r316 is an integer from 1 to 5, and if r316 is 2 or more, the 2 or more R316s are the same or different from each other.

[0377] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

[0378] According to one embodiment of the present specification, the R317 is any one selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; and combinations thereof.

[0379] According to one embodiment of the present specification, R315 and R316 are the same or different from each other and are each independently substituted or unsubstituted aryl groups, or they combine with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0380] According to one embodiment of the present specification, R315 and R316 are the same or different from each other and are each independently a phenyl group, or they combine with adjacent groups to form an indene ring that is substituted or unsubstituted with an ethyl group.

[0381] According to one embodiment of the present specification, the chemical formula HT-2 is represented by the following compound.

[0382]

[0383] The electron transport layer described above is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. As for the electron transport material, it is a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, and a material with high electron mobility is preferred. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material as in the prior art. In particular, a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically, examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum layer or a silver layer.

[0384] The electron injection layer described above is a layer that receives electrons from an electrode. It is desirable for the electron injection material to have excellent electron transport ability, an electron reception effect from the cathode, and an excellent electron injection effect on the emitting layer or emitting material. In addition, it is desirable for the material to prevent excitons generated in the emitting layer from moving to the hole injection layer and to have excellent thin film formation ability. Specifically, examples include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but are not limited thereto.

[0385] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, Examples include bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, but are not limited thereto.

[0386] The above electron blocking layer is a layer capable of improving the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. Known materials may be used without limitation and can be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that performs both hole injection and hole transport simultaneously.

[0387] The hole blocking layer described above is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc. are used, but are not limited thereto.

[0388] The organic light-emitting device according to the present specification may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0389] The above organic light-emitting element may be included in various electronic devices. For example, an electronic device including the above organic light-emitting element may be a light-emitting device, an authentication device, a display device, a lighting device, a mobile terminal, a wearable device, and various other electronic devices. Specifically, the above display device may include a TV, a monitor, a smartphone, a tablet, a laptop display, a smartwatch, a vehicle cluster, a VR / AR display, etc.

[0390] Hereinafter, in order to specifically explain the present specification, examples and comparative examples will be described in detail. However, the examples and comparative examples according to the present specification may be modified in various different forms, and the scope of the present specification is not to be interpreted as being limited to the examples and comparative examples described below. The examples and comparative examples of the present specification are provided to more completely explain the present specification to those with average knowledge in the art.

[0391] [Preparation Example]

[0392] Preparation Example 1-1: Preparation of Compound E1

[0393]

[0394] Under a nitrogen atmosphere, E1-P1-A (20 g, 85.1 mmol) and E1-P1-B (16.3 g, 85.1 mmol) were added to 400 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (35.3 g, 255.2 mmol) was dissolved in 35 ml of water and added, and after sufficient stirring, tetracitriphenyl-phosphinopalladium (2.9 g, 2.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, separated into organic and water layers, and the organic layer was distilled. This was dissolved again in 400 ml of chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. A white solid compound E1-P1 (11.8 g, 63%, MS: [M+H]+ = 220) was prepared by recrystallizing the concentrated compound with chloroform and ethyl acetate.

[0395]

[0396] Under a nitrogen atmosphere, E1-P1 (20 g, 91 mmol) and bis(pinacollato)diborone (23.1 g, 91 mmol) were added to 400 ml of 1,4-Dioxane and stirred and refluxed. Subsequently, tripotassium phosphate (58 g, 273.1 mmol) was added and stirred thoroughly, after which palladium dibenzylideneacetone palladium (1.6 g, 2.7 mmol) and tricyclohexylphosphine (1.5 g, 5.5 mmol) were added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was dissolved in 300 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. A white solid compound E1-P2 (20.4g, 72%, MS: [M+H]+ = 312) was prepared by recrystallizing the concentrated compound with chloroform and ethanol.

[0397]

[0398] Under a nitrogen atmosphere, E1-P2 (20 g, 64.3 mmol) and E1-P3-A (17.1 g, 64.3 mmol) were added to 400 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (26.6 g, 192.8 mmol) was dissolved in 27 ml of water and added, and after sufficient stirring, tetracitriphenyl-phosphinopalladium (2.2 g, 1.9 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, separated into organic and water layers, and the organic layer was distilled. This was dissolved again in 500 ml of chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. A white solid compound E1-P3 (13.2 g, 55%, MS: [M+H]+ = 375) was prepared by recrystallizing the concentrated compound with chloroform and ethyl acetate.

[0399]

[0400] Under a nitrogen atmosphere, E1-P3 (20 g, 53.4 mmol) and E1-B (31.3 g, 53.4 mmol) were added to 400 ml of 1,4-Dioxane and stirred and refluxed. Subsequently, tripotassium phosphate (34 g, 160.1 mmol) dissolved in 34 ml of water was added and stirred thoroughly, after which dibenzylideneacetone palladium (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. After reacting for 5 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 1300 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. A yellow solid compound E1 (6.4g, 15%, MS: [M+H]+ = 800) was prepared by recrystallizing the concentrated compound with chloroform and ethyl acetate.

[0401]

[0402] Preparation Example 1-2: Preparation of Compound E2

[0403]

[0404] Compound E2 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0405] MS: [M+H]+ = 724

[0406]

[0407] Preparation Examples 1-3: Preparation of Compound E3

[0408]

[0409] Compound E3 was prepared in the same manner as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0410] MS: [M+H]+ = 724

[0411]

[0412] Preparation Examples 1-4: Preparation of Compound E4

[0413]

[0414] Compound E4 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0415] MS: [M+H]+ = 749

[0416]

[0417] Preparation Examples 1-5: Preparation of Compound E5

[0418]

[0419] Compound E5 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0420] MS: [M+H]+ = 828

[0421]

[0422] Preparation Examples 1-6: Preparation of Compound E6

[0423]

[0424] Compound E6 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0425] MS: [M+H]+ = 876

[0426]

[0427] Preparation Examples 1-7: Preparation of Compound E7

[0428]

[0429] Compound E7 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the above reaction scheme.

[0430] MS: [M+H]+ = 800

[0431]

[0432] Preparation Examples 1-8: Preparation of Compound E8

[0433]

[0434] Compound E8 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0435] MS: [M+H]+ = 1002

[0436]

[0437] Preparation Examples 1-9: Preparation of Compound E9

[0438]

[0439] Compound E9 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0440] MS: [M+H]+ = 848

[0441]

[0442] Preparation Examples 1-10: Preparation of Compound E10

[0443]

[0444] Compound E10 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the above reaction scheme.

[0445] MS: [M+H]+ = 829

[0446]

[0447] Preparation Examples 1-11: Preparation of Compound E11

[0448]

[0449] Compound E11 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0450] MS: [M+H]+ = 850

[0451]

[0452] Preparation Examples 1-12: Preparation of Compound E12

[0453]

[0454] Compound E12 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0455] MS: [M+H]+ = 800

[0456]

[0457] Preparation Example 1-13: Preparation of Compound E13

[0458]

[0459] Compound E13 was prepared in the same manner as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0460] MS: [M+H]+ = 876

[0461]

[0462] Preparation Examples 1-14: Preparation of Compound E14

[0463]

[0464] Compound E14 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0465] MS: [M+H]+ = 925

[0466]

[0467] Preparation Example 1-15: Preparation of Compound E15

[0468]

[0469] Compound E15 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0470] MS: [M+H]+ = 900

[0471]

[0472] Preparation Example 1-16: Preparation of Compound E16

[0473]

[0474] Compound E16 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0475] MS: [M+H]+ = 800

[0476]

[0477] Preparation Example 1-17: Preparation of Compound E17

[0478]

[0479] Compound E17 was prepared in the same manner as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0480] MS: [M+H]+ = 876

[0481]

[0482] Preparation Example 1-18: Preparation of Compound E18

[0483]

[0484] Compound E18 was prepared in the same manner as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the above reaction scheme.

[0485] MS: [M+H]+ = 899

[0486]

[0487] Preparation Example 1-19: Preparation of Compound E19

[0488]

[0489] Compound E19 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0490] MS: [M+H]+ = 800

[0491]

[0492] Preparation Example 1-20: Preparation of Compound E20

[0493]

[0494] Compound E20 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0495] MS: [M+H]+ = 841

[0496]

[0497] Preparation Example 1-21: Preparation of Compound E21

[0498]

[0499] Compound E21 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0500] MS: [M+H]+ = 784

[0501]

[0502] Preparation Example 1-22: Preparation of Compound E22

[0503]

[0504] Compound E22 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0505] MS: [M+H]+ = 708

[0506]

[0507] Preparation Example 1-23: Preparation of Compound E23

[0508]

[0509] Compound E23 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0510] MS: [M+H]+ = 784

[0511]

[0512] Preparation Example 1-24: Preparation of Compound E24

[0513]

[0514] Compound E24 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0515] MS: [M+H]+ = 860

[0516]

[0517] Preparation Example 1-25: Preparation of Compound E25

[0518]

[0519] Compound E25 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0520] MS: [M+H]+ = 784

[0521]

[0522] Preparation Example 1-26: Preparation of Compound E26

[0523]

[0524] Compound E26 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0525] MS: [M+H]+ = 797

[0526]

[0527] Preparation Example 1-27: Preparation of Compound E27

[0528]

[0529] Compound E27 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0530] MS: [M+H]+ = 784

[0531]

[0532] Preparation Example 1-28: Preparation of Compound E28

[0533]

[0534] Compound E28 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0535] MS: [M+H]+ = 834

[0536]

[0537] Preparation Example 1-29: Preparation of Compound E29

[0538]

[0539] Compound E29 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0540] MS: [M+H]+ = 833

[0541]

[0542] Preparation Example 1-30: Preparation of Compound E30

[0543]

[0544] Compound E30 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the above reaction scheme.

[0545] MS: [M+H]+ = 808

[0546]

[0547] Preparation Example 1-31: Preparation of Compound E31

[0548]

[0549] Compound E31 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0550] MS: [M+H]+ = 758

[0551]

[0552] Preparation Example 1-32: Preparation of Compound E32

[0553]

[0554] Compound E32 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0555] MS: [M+H]+ = 860

[0556]

[0557] Preparation Example 1-33: Preparation of Compound E33

[0558]

[0559] Compound E33 was prepared in the same manner as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0560] MS: [M+H]+ = 784

[0561]

[0562] Preparation Example 1-34: Preparation of Compound E34

[0563]

[0564] Compound E34 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0565] MS: [M+H]+ = 784

[0566]

[0567] Preparation Example 1-35: Preparation of Compound E35

[0568]

[0569] Compound E35 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0570] MS: [M+H]+ = 784

[0571]

[0572] Preparation Example 1-36: Preparation of Compound E36

[0573]

[0574] Compound E36 was prepared in the same manner as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0575] MS: [M+H]+ = 860

[0576]

[0577] Preparation Example 1-37: Preparation of Compound E37

[0578]

[0579] Compound E37 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0580] MS: [M+H]+ = 860

[0581]

[0582] Preparation Example 1-38: Preparation of Compound E38

[0583]

[0584] Compound E38 was prepared in the same manner as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the above reaction scheme.

[0585] MS: [M+H]+ = 888

[0586]

[0587] Preparation Example 1-39: Preparation of Compound E39

[0588]

[0589] Compound E39 was prepared in the same manner as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0590] MS: [M+H]+ = 808

[0591]

[0592] Preparation Example 1-40: Preparation of Compound E40

[0593]

[0594] Compound E40 was prepared in the same manner as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the above reaction scheme.

[0595] MS: [M+H]+ = 792

[0596] [Example]

[0597] Example 1-1

[0598] A glass substrate coated with an indium tin oxide (ITO) thin film to a thickness of 1,000 Å was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. products were used as the detergent, and distilled water that had been filtered twice using a Millipore Co. filter was used. After cleaning the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol as solvents, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes and then transported to a vacuum deposition machine.

[0599] A hole injection layer was formed by thermal vacuum deposition of the following compound HI-A to a thickness of 600 Å on the ITO transparent electrode prepared in this way. A first hole transport layer and a second hole transport layer were formed by sequentially vacuum depositing the following compound HAT to a thickness of 50 Å and the following compound HT-A to a thickness of 60 Å on the hole injection layer.

[0600] Next, a light-emitting layer was formed by vacuum depositing the following compounds BH and BD in a weight ratio of 25:1 on the second hole transport layer with a film thickness of 200 Å.

[0601] An electron injection and transport layer with a thickness of 350 Å was formed by vacuum depositing the previously prepared compound E1 and the following compound LiQ in a weight ratio of 1:1 on the above-mentioned light-emitting layer. A cathode was formed by sequentially depositing lithium fluoride (LiF) with a thickness of 10 Å and aluminum with a thickness of 1000 Å on the above-mentioned electron injection and transport layer.

[0602]

[0603] In the above process, the deposition rate of the organic material was maintained at 0.4 Å / sec to 0.9 Å / sec, while the deposition rates of lithium fluoride and aluminum for the cathode were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 1 * 10 -7 torr to 5 * 10 -5 An organic light-emitting diode was fabricated by maintaining torr.

[0604] Examples 1-2 to 1-40

[0605] An organic light-emitting diode was manufactured in the same manner as in Example 1-1, except that compounds E2 to E40 listed in Table 1 below were used instead of compound E1 of Example 1-1.

[0606]

[0607]

[0608] Comparative Examples 1-1 to 1-8

[0609] An organic light-emitting diode was prepared in the same manner as in Example 1-1, except that compounds ET-1 to ET-8 of Table 1 below were used respectively instead of compound E1 of Example 1-1. The structures of compounds ET-1 to ET-8 of Table 1 below are as follows.

[0610]

[0611]

[0612] [Experimental Example]

[0613] For the organic light-emitting diodes prepared in Examples 1-1 to 1-40 and Comparative Examples 1-1 to 1-8 above, 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm². 2 The time (T90) to reach 90% of the initial brightness at the current density was measured. The results are shown in Table 1 below.

[0614]

[0615] Classification Compound Voltage (V) (@10 mA / cm²) 2 )Efficiency (cd / A)(@10 mA / cm 2 Color coordinates (x, y) Lifespan (hr) (T90 at 20 mA / cm 2Example 1-1 E14.28 4.62 (0.138, 0.113) 192 Example 1-2 E24.24 4.71 (0.138, 0.112) 173 Example 1-3 E34.26 4.72 (0.138, 0.112) 175 Example 1-4 E44.45 4.39 (0.138, 0.113) 244 Example 1-5 E54.38 4.48 (0.138, 0.113) 171 Example 1-6 E64.30 4.77 (0.138, 0.113) 168 Example 1-7 E74.34 4.75 (0.138, 0.112) 173 Example 1-8E84.374.50(0.138, 0.113)190 Example 1-9E94.344.38(0.138, 0.113)154 Example 1-10E104.434.44(0.138, 0.112)166 Example 1-11E114.344.67(0.138, 0.112)185 Example 1-12E124.194.73(0.138, 0.113)196 Example 1-13E134.264.78(0.138, 0.112)176 Example 1-14E144.414.42(0.138, 0.112)172 Example 1-15E154.414.53(0.138, 0.112)205 Example 1-16E164.204.79(0.138, 0.112)171 ​​Example 1-17E174.284.66(0.138, 0.112)213 Example 1-18E184.384.53(0.138, 0.112)164 Example 1-19E194.194.73(0.138, 0.113)198 Example 1-20E204.474.35(0.138, 0.112)162 Example 1-21E214.244.68(0.138, 0.113)186 Example 1-22E224.284.69(0.138, 0.113)185 Example 1-23E234.224.80(0.138, 0.112)178 Example 1-24E244.264.78(0.138, 0.112)185 Example 1-25E254.274.78(0.138, 0.113)181 Example 1-26E264.344.57(0.138, 0.112)172 Example 1-27E274.244.72(0.138, 0.112)198 Example 1-28E284.324.63(0.138, 0.112)216 Example 1-29E294.414.49(0.138, 0.113)183 Example 1-30E304.504.35(0.138, 0.112)202 Example 1-31E314.394.65(0.138, 0.112)207 Example 1-32E324.294.65(0.138, 0.113)214 Example 1-33E334.224.77(0.138, 0.112)188 Example 1-34E344.274.70(0.138, 0.112)195 Example 1-35E354.224.82(0.138, 0.113)173 Example 1-36E364.294.74(0.138, 0.112)182 Example 1-37E374.224.72(0.138, 0.112)185 Example 1-38E384.454.39(0.138, 0.112)169 Example 1-39E394.284.62(0.138, 0.112)204 Example 1-40E404.224.77(0.138, 0.112)201 Comparative Example 1-1ET-15.842.17(0.138, 0.113)77 Comparative Example 1-2 ET-25.75 2.00(0.138, 0.112)80 Comparative Example 1-3 ET-35.39 2.04(0.138, 0.112)108 Comparative Example 1-4 ET-45.80 1.96(0.138, 0.112)62 Comparative Example 1-5 ET-56.29 1.30(0.138, 0.112)46 Comparative Example 1-6 ET-66.36 1.28(0.138, 0.113)42 Comparative Example 1-7 ET-74.41 3.48(0.138, 0.112)38 Comparative Example 1-8 ET-84.47 3.30(0.138, 0.112)40.

[0616] As described in Table 1 above, the organic light-emitting devices of Examples 1-1 to 1-40, in which the compound represented by Formula 1 according to the present specification was used in the electron injection and electron transport layers of the organic light-emitting device, exhibited low driving voltage and excellent characteristics in terms of efficiency and lifespan.

Claims

1. Compound of Chemical Formula 1 below: [Chemical Formula 1] In the above chemical formula 1, HAr1 and HAr2 are identical or different from each other, each independently substituted or unsubstituted, and are heterocyclic rings comprising two or more heteroatoms selected from the group consisting of N, O and S, and L1 and L2 are identical or different from each other, and each is an independently substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and n1 and n2 are identical or different from each other and are each independently integers from 1 to 5, and if n2 is 2 or more, L1 and L2 are identical or different from each other, and At least one of the above HAr1 and HAr2 is substituted with one or more of the following chemical formula 2, and [Chemical Formula 2] In the above chemical formula 2, Z1 is O; or S, and L3 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and R1 is hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted aryl group; substituted or unsubstituted aryloxy group; substituted or unsubstituted arylthio group; or substituted or unsubstituted heteroaryl group, and n3 is an integer from 0 to 5, and if it is 2 or greater, L3 are identical or different from each other, and m1 is an integer from 1 to 3, and r1 is an integer from 0 to 2, and when r1 is 2, R1 are the same or different.

2. In Claim 1, The above HAr1 and HAr2 are identical or different from each other, and each independently has the following chemical formula 101 or 201: [Chemical Formula 101] [Chemical Formula 201] In the above chemical formulas 101 and 201, X1 to X6 are identical or different from each other, and each is independently a heteroatom of N; or CR2, and Y1 is a heteroatom selected from the group consisting of NR2, O, and S; or CR22, and Y2 to Y5 are identical or different from each other, and each is independently a heteroatom of N; or CR2, and At least two of X1 to X6 are the above heteroatoms, and At least two of Y1 to Y5 are the above heteroatoms, and One of R2 is connected to the above Formula 1, and the remainders are identical or different from one another, each independently hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted aryl group; substituted or unsubstituted aryloxy group; substituted or unsubstituted arylthio group; substituted or unsubstituted heteroaryl group; or the above Formula 2, or is combined with adjacent substituents to form a substituted or unsubstituted ring, and In at least one of the above HAr1 and HAr2, 1 or more R2 is the above chemical formula 2.

3. In Claim 2, The above chemical formula 101 is a compound that is one of the following chemical formulas 102 to 104: [Chemical Formula 102] [Chemical Formula 103] [Chemical Formula 104] In the above chemical formulas 102 to 104, X1 to X6 are as defined in the above chemical formula 101, and One of R2 is connected to the above Formula 1, and the remainders are identical or different from one another, and each independently hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or the above Formula 2, and Z2 is O; S; or NR3, and R3 is hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or the above formula 2, r3 is an integer from 0 to 4, and if it is 2 or greater, R3 are the same or different from each other.

4. In Claim 2, The above chemical formula 201 is a compound having the following chemical formula 202 or 203: [Chemical Formula 202] [Chemical Formula 203] In the above chemical formulas 202 and 203, Y1 to Y5 are as defined in the above chemical formula 201, and One of R2 is connected to the above Formula 1, and the remainders are identical or different from one another, and each independently hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or the above Formula 2, and R3 is hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or the above formula 2, r3 is an integer from 0 to 4, and if it is 2 or greater, R3 are the same or different from each other.

5. In Claim 1, The above L1 to L3 are compounds that are identical or different from each other and are each independently selected from the following structures: The above structure is substituted or unsubstituted with deuterium, and The dotted line is connected to the above chemical formula 1, and Z3 is O; S; NR4; or CR42, and R4 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

6. In Claim 1, Compounds in which at least one of the above L1 and L2 is selected from the following structures: The above structure is substituted or unsubstituted with deuterium.

7. In Claim 1, The above HAr1 and HAr2 are identical or different from each other and each independently comprises two or more heteroatoms selected from the group consisting of N, O, and S, wherein they are heterocyclic rings comprising one or more N, and the above HAr1 and HAr2 are substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, alkyl groups, and aryl groups, or with substituents connected to two or more groups selected from said group. The above L1 and L2 are identical or different from each other and are each independently arylene groups, and the above L1 and L2 are substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, alkyl groups, and aryl groups, or with substituents connected to two or more groups selected from said group. The above L3 is a direct bond; or an arylene group, and the above L3 is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, alkyl groups, and aryl groups, or with a substituent connected to two or more groups selected from said group, and The above R1 is hydrogen; deuterium; an alkyl group; or an aryl group, and the above R1 is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, and an aryl group, or with a substituent connected to two or more groups selected from said group. A compound in which the carbon number of the alkyl group is 1 to 30, the carbon number of the aryl group and the arylene group is 6 to 60, and the carbon number of the heterocyclic group is 2 to 60.

8. A compound according to Claim 1, wherein the compound of Formula 1 is any one selected from the following compounds: .

9. An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound according to any one of claims 1 to 8.

10. In Claim 9, The above organic layer includes an electron injection layer, an electron transport layer, an electron injection and transport layer, or a hole blocking layer, and An organic light-emitting device in which the electron injection layer, electron transport layer, electron injection and transport layer, or hole blocking layer comprises the above compound.

11. An organic light-emitting device according to claim 10, wherein the electron injection layer, electron transport layer, electron injection and transport layer or hole blocking layer further comprises an n-type dopant.

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