Compound and organic light-emitting device comprising same

Abstract

Disclosed are a compound of Chemical Formula 1 and an organic light emitting device comprising the same. The compound described in the specification can be used as a material for an organic material layer of an organic light-emitting device. The compound according to at least one exemplary embodiment of the present specification may improve efficiency, achieve low driving voltage, and / or improve lifespan characteristics in an organic light emitting device. In particular, the compounds described in the specification can be used as materials for electron injection and transport layers. Further, an organic light-emitting device in which the compound described in the present specification is used has the effects of low driving voltage, high efficiency, and / or long lifespan compared to an existing organic light-emitting device.

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0130723, filed on September 26, 2024, and Korean Patent Application No. 10-2025-0118231, filed on August 25, 2025, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This specification relates to compounds and organic light-emitting devices containing them. Background Technology

[0004] In this specification, an organic light-emitting device (OLED) is a light-emitting device that uses organic semiconductor materials and requires the exchange of holes and / or electrons between the electrodes and the organic semiconductor material. Based on their working principles, OLEDs can be broadly classified into two types. The first type of OLED is one in which photons flowing from an external light source to the device form excitons in the organic material layer. These excitons are then separated into electrons and holes, which are each transferred to different electrodes and used as current sources (voltage sources). The second type of OLED is one in which holes and / or electrons are injected into the organic semiconductor material layer that forms an interface with the electrodes by applying a voltage or current to two or more electrodes, and the device operates through the injected electrons and holes.

[0005] Organic light emission (OLED) generally refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) typically have a structure comprising an anode, a cathode, and an organic material layer between them. To improve the efficiency and stability of OLEDs, the organic material layer often has a multilayer structure composed of different materials, and can be, for example, composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer. In the structure of an OLED, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode into the organic material layer. When the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons fall back to the ground state. Such OLEDs are known to possess characteristics such as self-emission, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

[0006] In organic light-emitting devices, the materials used as organic material layers can be classified into light-emitting materials and charge-transporting materials according to their functions. Examples include hole injection materials, hole transport materials, electron blocking materials, electron transport materials, and electron injection materials. Light-emitting materials are classified according to their emission color, including materials that emit blue light, materials that emit green light, and materials that emit red light, as well as materials that emit yellow light and materials that emit orange light, which are needed to achieve a much better natural color.

[0007] Furthermore, to improve color purity and luminous efficiency through energy transfer, a host / dopant system can be used as the luminescent material. The principle is that when a small amount of a dopant with a smaller band gap and better luminous efficiency than the host that mainly constitutes the luminescent layer is mixed into the luminescent layer, excitons generated by the host are transferred to the dopant to emit light with high efficiency. In this case, since the wavelength of the host shifts to the wavelength range of the dopant, light with the desired wavelength can be obtained depending on the type of dopant used.

[0008] In order to fully demonstrate the superior characteristics of organic light-emitting devices, the materials constituting the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron blocking materials, electron transport materials, and electron injection materials, need to be supported by stable and effective materials. Therefore, it is necessary to continuously develop new materials.

[0009] [Related Technical Documents]

[0010] [Patent Literature]

[0011] (Patent Document 1) International Patent Publication No. 2017-126443 Summary of the Invention

[0012] This invention aims to provide compounds and organic light-emitting devices containing them.

[0013] An exemplary embodiment of the present invention provides a compound of the following chemical formula 1.

[0014] [Chemical Formula 1]

[0015]

[0016] In chemical formula 1,

[0017] HAr1 is a divalent triazine group, either unsubstituted or substituted with one of the following substituents: deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; or a divalent triazine group, either unsubstituted or substituted with one or two substituents, each independently selected from deuterium, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms. Pyrimidinyl; an unsubstituted or deuterated divalent quinazolinyl; an unsubstituted or substituted divalent benzothiophene-pyrimidinyl with a substituent selected from deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; or an unsubstituted or substituted divalent benzofuran-pyrimidinyl with a substituent selected from deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms.

[0018] HAr2 is a triazine group, either unsubstituted or substituted with two substituents selected independently of deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; or a pyrimidinyl group, either unsubstituted or substituted with one to three substituents selected independently of deuterium, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; or an unsubstituted or substituted triazine group, either substituted or substituted with one to three substituents selected independently of deuterium, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, and substituted aryl groups having 6 to 60 carbon atoms. A quinazolinyl group consisting of an aryl group having 2 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted; a benzothiophene-pyrimidinyl group consisting of an unsubstituted or substituted aryl group having 6 to 60 carbon atoms, substituted or unsubstituted, or a heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted; or a benzofuran-pyrimidinyl group consisting of an unsubstituted or substituted aryl group having 6 to 60 carbon atoms, substituted or unsubstituted, or a heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted.

[0019] L1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0020] Ar1 is an aryl group having 6 to 60 carbon atoms that has one or more cyano groups and is optionally further deuterated.

[0021] Ar21 to Ar23 may be the same as or different from each other, and each is independently hydrogen; deuterium; or aryl groups with 6 to 60 carbon atoms, substituted or unsubstituted.

[0022] R1 and R2 may be the same as or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0023] n is an integer from 1 to 4, and when n is 2 or greater, R1 is either the same or different from each other.

[0024] m is an integer from 1 to 3, and when m is 2 or greater, R² are either the same or different from each other.

[0025] a1, a2, and a3 are each 0 or 1.

[0026] ,as well as

[0027] .

[0028] Another exemplary embodiment provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain the aforementioned compound.

[0029] The compounds of the present invention can be used as materials for organic material layers in organic light-emitting devices. When organic light-emitting devices are manufactured by including the compounds of the present invention, organic light-emitting devices with high efficiency, low voltage and long lifespan characteristics can be obtained. Furthermore, when the compounds of the present invention are included in the electron transport layer of an organic light-emitting device, the high intramolecular polarization results in a high electron transfer effect, making it possible to manufacture organic light-emitting devices with long lifespan characteristics.

[0030] The organic light-emitting device of the present invention is characterized by comprising all of the compounds represented by Chemical Formula 1. In this case, the compounds of the present invention allow for a suitable energy barrier for the LUMO orbital energy at the level of -2.8 eV to -3.2 eV by substituting the linking group between the two heterocyclic groups in the para and meta positions, exhibit high efficiency characteristics by increasing the planarity of the material to maximize electron mobility, and maintain long lifetime characteristics by substituting the cyano group with excellent polarizability. Attached Figure Description

[0031] Figures 1 to 3 An example of an organic light-emitting device according to the present invention is shown. Detailed Implementation

[0032] This instruction manual will be described in more detail below.

[0033] In this specification, when a part "includes" a constituent element, unless otherwise specifically described, this does not mean the exclusion of other constituent elements, but rather that other constituent elements may be included.

[0034] In this specification, when a component is positioned "on" another component, this includes not only the case where one component is in contact with another component, but also the case where there is another component between the two components.

[0035] In this specification, "dashed lines" "This refers to the position where a chemical formula or compound is bonded."

[0036] In this specification, the deuterium substitution rate of a compound can be understood by: calculating the substitution rate based on the maximum value of the distribution of molecular weight at the reaction endpoint using thin-layer chromatography / mass spectrometry (TLC-MS); or by using quantitative analysis using NMR; and by adding DMF as an internal standard and calculating the deuterium substitution rate from the integral of the total peak using the integral rate on 1H NMR.

[0037] In this specification, “X% deuterated”, “X% degree of deuteration”, or “X% deuteration rate” means that X% of the hydrogen atoms at the substituted positions in the corresponding structure are replaced by deuterium.

[0038] In this specification, the hydrogen atoms that can be substituted by deuterium in the corresponding structure can be substituted by deuterium at a rate greater than 0% and 100% or less, 0.1% or greater and 99.99% or less, or up to 100%. For example, when the corresponding structure is dibenzofuran, dibenzofuran is "25% deuterated", the "25% degree of deuteration" of dibenzofuran, or the "25% deuteration rate" of dibenzofuran, can mean that two of the eight hydrogen atoms at the substituted positions of dibenzofuran are substituted by deuterium, and "50% deuteration rate" can mean that four of the eight hydrogen atoms at the substituted positions of dibenzofuran are substituted by deuterium.

[0039] The term “substitution” means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and there are no restrictions on the position to be substituted, as long as the position is where the hydrogen atom is replaced (i.e., the position where the substituent can be replaced), and when two or more hydrogen atoms are replaced, the two or more substituents can be the same as or different from each other.

[0040] In this invention, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; halogen group; cyano (-CN); nitro; hydroxyl; alkyl; cycloalkyl; alkoxy; phosphine oxide; aryloxy; alkylthio; arylthio; alkylsulfonyl; arylsulfonyl; alkenyl; silyl; boronyl; amino; aryl; and heterocyclic groups, substituted with two or more of the exemplified substituents linked together, or without substituents. For example, "substituents linked with two or more substituents" can be biphenyl. That is, biphenyl can also be aryl and can be interpreted as substituents linked with two phenyl groups.

[0041] In this specification, the term "substituted or unsubstituted" means substituted with one or more of the following substituents selected from: deuterium; halogen group; cyano; silyl; alkoxy; aryloxy; alkyl; aryl; and heterocyclic group, substituted with a substituent connected to two or more of the exemplified substituents, or without substituents.

[0042] In this specification, the term "substituted or unsubstituted" means substituted with one or more of the following substituents selected from: deuterium; alkyl; aryl; and heterocyclic, substituted with a substituent linked to two or more of the exemplified substituents, or has no substituents.

[0043] In this specification, the fact that two or more substituents are linked means that the hydrogen of any one substituent is linked to another substituent. For example, isopropyl and phenyl can be linked to each other to become substituents. or .

[0044] In this specification, the fact that three substituents are linked to each other includes not only the case where (substituent 1)-(substituent 2)-(substituent 3) are sequentially linked to each other, but also the case where (substituent 2) and (substituent 3) are linked to (substituent 1). For example, two phenyl groups and one isopropyl group can be linked to each other to become substituents. or It also applies to cases where four or more substituents are connected to each other.

[0045] Examples of substituents will be described below; however, substituents are not limited to these.

[0046] Examples of halogen groups in this specification include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0047] In this specification, silane can be derived from the formula... This indicates that Ya, Yb, and Yc can each be hydrogen; substituted or unsubstituted alkyl groups; or substituted or unsubstituted aryl groups. Specific examples of silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc.

[0048] In this specification, the boron group can be derived from the formula... This indicates that Yd and Ye can each be hydrogen; substituted or unsubstituted alkyl groups; or substituted or unsubstituted aryl groups. Specific examples of boron groups include, but are not limited to, dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, phenylboryl, etc.

[0049] In this specification, the alkyl group can be straight-chain or branched, and its number of carbon atoms is not particularly limited, but is preferably from 1 to 60. According to one exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to yet another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc.

[0050] In this specification, propyl includes n-propyl and isopropyl.

[0051] In this specification, the above description of alkyl groups can be applied to arylalkyl groups, except that arylalkyl groups are substituted with aryl groups.

[0052] In this specification, the alkoxy group can be straight-chain, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20. Specific examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, and n-decoxy.

[0053] The substituents described in this specification, including alkyl, alkoxy, and other alkyl moieties, include both straight-chain and branched forms.

[0054] In this specification, the alkenyl group can be straight-chain or branched, and its number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to yet another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, It includes, but is not limited to, styrene, etc.

[0055] In this specification, the alkynyl group, as a substituent containing a triple bond between carbon atoms, can be straight-chain or branched, and its number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms.

[0056] In this specification, cycloalkyl groups are not particularly limited, but preferably have 3 to 60 carbon atoms, and according to one exemplary embodiment, the number of carbon atoms in a cycloalkyl group is 3 to 30. According to another exemplary embodiment, the number of carbon atoms in a cycloalkyl group is 3 to 20. According to yet another embodiment, the number of carbon atoms in a cycloalkyl group is 3 to 6. Specific examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc.

[0057] In this specification, the amino group is Furthermore, the amino group can be substituted with the aforementioned alkyl, aryl, heterocyclic, alkenyl, cycloalkyl, or combinations thereof. The number of carbon atoms in the substituted amino group is not particularly limited, but is preferably from 1 to 30. According to one exemplary embodiment, the amino group has 1 to 20 carbon atoms. According to one exemplary embodiment, the amino group has 1 to 10 carbon atoms. Specific examples of substituted amino groups include, but are not limited to, methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9,9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthraceneamino, dibenzofuranylphenylamino, 9-methylanthraylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenyltolylamino, diphenylamino, etc.

[0058] In this specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and can be a monocyclic aryl or polycyclic aryl. According to one exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to another exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group can be composed of monocyclic or polycyclic aryl groups (bicyclic or more cyclic aryl groups). A monocyclic aryl group can mean a phenyl group; or a group in which two or more phenyl groups are linked. Examples of monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, tetraphenyl, etc. Polycyclic aryl groups can mean a group in which two or more monocyclic groups, such as naphthyl and phenanthrene, are fused. Examples of polycyclic aryl groups include naphthyl, anthraceneyl, phenanthreneyl, pyreneyl, etc. base, It includes, but is not limited to, methyl, fluorene, triphenylene, etc.

[0059] In this specification, the fluorene group may be substituted, and two substituents may bond together to form a spirocyclic structure.

[0060] When the fluorene group is substituted, the substituent can be a spirofluorene group, for example... and and substituted fluorene groups, for example (9,9-dimethylfluorenyl) and (9,9-Diphenylfluorenyl). However, the substituents are not limited to this.

[0061] In this specification, the above description of aryl groups can be applied to aryl groups in aryloxy groups.

[0062] In this specification, a heterocyclic group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and its number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to another embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of heterocyclic groups include, but are not limited to, pyridinyl, pyrroloyl, pyrimidinyl, quinolinyl, pyridazinyl, furanyl, thiopheneyl, imidazoyl, pyrazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocarbazoleyl, naphthobenzofuranyl, benzonaphthothiopheneyl, indocarbazoleyl, triazinyl, etc.

[0063] In this specification, the above description of heterocyclic groups can be applied to heteroaryl groups, except that heteroaryl groups are aromatic.

[0064] In this specification, a heteroaryl group comprises one or more atoms other than carbon (i.e., one or more heteroatoms), and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, etc. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thienyl, furanyl, pyrroleyl, imidazolyl, thiazolyl, etc. azole group, Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazenopyrazinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthridine, phenanthrolinyl, iso Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothiopyrrolyl, phen Thiol, phen Azinyl, phenothiazinyl, dihydroindocarbazolyl, spirofluorene Examples include, but are not limited to, ton-based, spirofluorene-thion-based, etc.

[0065] In this specification, the description of aryl can be applied to arylene, except that arylene is divalent.

[0066] In this specification, the description of heterocyclic groups can be applied to divalent heterocyclic groups, the difference being that the heterocyclic group is divalent.

[0067] In this specification, the description of aryl groups can be applied to ( ) aryl, the difference being that the aryl group is ( (Price)

[0068] In this specification, the description of heterocyclic groups can be applied to ( The difference lies in the fact that the heterocyclic group is ( (Price)

[0069] In this specification, in substituted or unsubstituted rings formed by bonding with adjacent groups, "ring" means a hydrocarbon ring; or a heterocycle.

[0070] The hydrocarbon ring can be an aromatic ring, an aliphatic ring, or a fused ring of aromatic and aliphatic rings, and can be selected from examples of cycloalkyl or aryl groups.

[0071] In this specification, "bonded with an adjacent group to form a ring" means bonded with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a fused ring thereof. A hydrocarbon ring means a ring consisting only of carbon and hydrogen atoms. A heterocycle means a ring containing one or more of N, O, P, S, Si, and Se. In this specification, aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles can be monocyclic or polycyclic.

[0072] In this specification, aliphatic hydrocarbon rings refer to rings consisting only of carbon and hydrogen atoms that are non-aromatic rings. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.

[0073] In this specification, aromatic hydrocarbon rings refer to aromatic rings composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, etc. fluoranthene, triphenylene, phenaene, pyrene, benzo[a]tetraphenyl Aromas include, but are not limited to, pentane, fluorene, indene, acenaphthene, benzo[a]fluorene, spirofluorene, etc. In this specification, the aromatic ring can be interpreted as having the same meaning as the aryl group.

[0074] In this specification, aliphatic heterocycle means an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include ethylene oxide, tetrahydrofuran, and 1,4-dioxane. Alkane, pyrrolidine, piperidine, morpholine, oxacycloheptane, azocyclooctane, thiocane, etc., but not limited to these.

[0075] In this specification, aromatic heterocycle means an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, etc. azole, isotonic azole, thiazole, isothiazole, triazole Diazole, thiadiazole, dithiazole, tetraazole, pyran, thiaran, diazine Azine, thiazide, diazine Indone, triazine, tetraazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthidine, acridine, phenanthridine, diazanaphthalene, triazaindene, indole, indazine, benzothiazole, benzo[a] azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenazine Examples include, but are not limited to, azines, indobenzocarbazole, and indobenzocarbazole.

[0076] In this specification, fused ring means a ring structure in which two or more rings share two or more atoms. Fused ring can be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a fused ring of aromatic hydrocarbon rings and aliphatic hydrocarbon rings, but is not limited thereto.

[0077] In this specification, fused aromatic hydrocarbon cycloyl group means a ring in which two or more aromatic hydrocarbon rings are fused together. Examples of fused aromatic hydrocarbon cycloyl groups may include naphthyl, anthraceneyl, phenanthryl, pyrene, etc. Triphenylene group It includes, but is not limited to, methyl, fluorene, triphenylenyl group, etc.

[0078] Unless otherwise specified in this specification, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. While methods and materials similar to or equivalent to those described herein may be used in practice or testing of exemplary embodiments of the invention, suitable methods and materials will be described below. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, this specification (including definitions) shall prevail unless a specific paragraph is cited. Furthermore, materials, methods, and examples are illustrative only and are not intended to be limiting.

[0079] In this specification, the positions in Formula 1 that can replace hydrogen may be replaced by deuterium.

[0080] In this specification, L1 of Formula 1 can be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and the positions in the aryl group that can replace hydrogen can be deuterated.

[0081] In this specification, Ar1 of chemical formula 1 can be an aryl group having 6 to 60 carbon atoms in which one or more cyano groups are substituted, and the positions in the aryl group that can substitute for hydrogen can be deuterated.

[0082] In this specification, Ar21 to Ar23 of Formula 1 may be the same or different, and may each be an aryl group having 6 to 60 carbon atoms, either substituted or unsubstituted, and the positions in the aryl group that may substitute for hydrogen may be deuterated.

[0083] In this specification, HAr1 of Formula 1 is a divalent triazine group, either unsubstituted or substituted with one of the following substituents: deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; a divalent pyrimidinyl group, either unsubstituted or substituted with one or two substituents selected independently of deuterium, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; an unsubstituted or deuterated divalent quinazolinyl group; or an unsubstituted... A divalent benzothiophene-pyrimidinyl group substituted with one of a substituent selected from deuterium, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a divalent benzofuran-pyrimidinyl group substituted with one of a substituent selected from deuterium, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and wherein the position in the divalent triazine group, divalent pyrimidinyl group, divalent quinazolinyl group, divalent benzothiophene-pyrimidinyl group, or divalent benzofuran-pyrimidinyl group where the hydrogen can be substituted can be deuterated.

[0084] In this specification, HAr2 of Formula 1 is a triazine group, either unsubstituted or substituted with two substituents selected independently of deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; a pyrimidinyl group, either unsubstituted or substituted with one to three substituents selected independently of deuterium, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; or an unsubstituted or substituted aryl group having 6 to 60 carbon atoms, and substituted or unsubstituted aryl groups having 2 to 60 carbon atoms. The quinazolinyl group substituted with one of the substituents of a heteroaryl group having 2 to 60 carbon atoms; the benzothiophene-pyrimidinyl group substituted with one of the substituents selected from deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; or the benzofuran-pyrimidinyl group substituted with one of the substituents selected from deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms, and the position in the triazineyl; pyrimidinyl; quinazolinyl; benzothiophene-pyrimidinyl; or benzofuran-pyrimidinyl group where hydrogen can be substituted can be deuterated.

[0085] In this specification, chemical formula 1 is any one of the following chemical formulas 1-1 to 1-5.

[0086] [Chemical Formula 1-1]

[0087]

[0088] [Chemical Formula 1-2]

[0089]

[0090] [Chemical Formulas 1-3]

[0091]

[0092] [Chemical Formulas 1-4]

[0093]

[0094] [Chemical Formulas 1-5]

[0095]

[0096] In chemical formulas 1-1 to 1-5,

[0097] HAr2, L1, Ar1, Ar21 to Ar23, n, m, and a1 to a3 are the same as those defined in Chemical Formula 1.

[0098] R1 and R2 may be the same as or different from each other, and each may independently be hydrogen or deuterium.

[0099] R3 is deuterium; an aryl group with 6 to 60 carbon atoms, substituted or unsubstituted; or a heteroaryl group with 2 to 60 carbon atoms, substituted or unsubstituted.

[0100] R4 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0101] o is 1 or 2, and

[0102] When o is 2, R4 are either the same or different from each other.

[0103] In this specification, the above chemical formula 1 refers to the above chemical formula 1-1.

[0104] In this specification, chemical formula 1 above refers to chemical formulas 1-2 above.

[0105] In this specification, chemical formula 1 refers to chemical formulas 1-3.

[0106] In this specification, chemical formula 1 refers to chemical formulas 1-4.

[0107] In this specification, chemical formula 1 refers to chemical formulas 1-5.

[0108] According to an exemplary embodiment of this specification, HAr1 is a divalent triazine group, either unsubstituted or substituted with one of a substituent selected from deuterium, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or either unsubstituted or substituted with one or two of a substituent selected independently from deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms. A divalent pyrimidinyl group substituted with a substituent; a divalent quinazolinyl group, either unsubstituted or deuterated; a divalent benzothiophene-pyrimidinyl group, either unsubstituted or substituted with a substituent selected from deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; or a divalent benzofuran-pyrimidinyl group, either unsubstituted or substituted with a substituent selected from deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms.

[0109] According to an exemplary embodiment of this specification, HAr1 is a divalent triazine group, either unsubstituted or substituted with one of the following substituents: deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; a divalent pyrimidinyl group, either unsubstituted or substituted with one or two substituents selected independently from deuterium, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; a divalent quinazoline group, either unsubstituted or deuterated; a divalent benzothiophenepyrimidinyl group, either unsubstituted or deuterated; or a divalent benzofuranopyrimidinyl group, either unsubstituted or deuterated.

[0110] According to an exemplary embodiment of this specification, HAr1 is a divalent triazine group, either unsubstituted or substituted with one of a substituent selected from deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; or either unsubstituted or substituted with one or two of a substituent selected independently from deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. A divalent pyrimidinyl group substituted with a substituent; a divalent quinazolinyl group, either unsubstituted or deuterated; a divalent benzothiophene-pyrimidinyl group, either unsubstituted or substituted with a substituent selected from deuterium, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms; or a divalent benzofuran-pyrimidinyl group, either unsubstituted or substituted with a substituent selected from deuterium, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms.

[0111] According to an exemplary embodiment of this specification, HAr1 is a divalent triazine group, either unsubstituted or substituted with one of a substituent selected from deuterium, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; or either unsubstituted or substituted with one or two of a substituent selected independently from deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms. A divalent pyrimidinyl group substituted with a substituent; a divalent quinazolinyl group, either unsubstituted or deuterated; a divalent benzothiophene-pyrimidinyl group, either unsubstituted or substituted with a substituent selected from deuterium, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 20 carbon atoms; or a divalent benzofuran-pyrimidinyl group, either unsubstituted or substituted with a substituent selected from deuterium, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 20 carbon atoms.

[0112] According to an exemplary embodiment of this specification, HAr1 is a divalent triazine group, either unsubstituted or substituted with one of a substituent selected from deuterium, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms; or either unsubstituted or substituted with one or two of a substituent selected independently from deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms. A divalent pyrimidinyl group substituted with a substituent; a divalent quinazoline group, either unsubstituted or deuterated; a divalent benzothiophene-pyrimidinyl group, either unsubstituted or substituted with a substituent selected from deuterium, substituted or unsubstituted aryl groups having 6 to 10 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 10 carbon atoms; or a divalent benzofuran-pyrimidinyl group, either unsubstituted or substituted with a substituent selected from deuterium, substituted or unsubstituted aryl groups having 6 to 10 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 10 carbon atoms.

[0113] According to an exemplary embodiment of this specification, HAr1 is a divalent triazine group, either unsubstituted or substituted with a substituent selected from deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyrimidinyl; or an unsubstituted triazine group, either unsubstituted or substituted with a substituent selected independently from deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted pyridyl. A divalent pyrimidinyl group substituted with one or both of the substituents; a divalent quinazolinyl group, either unsubstituted or deuterated; a divalent benzothiophene-pyrimidinyl group, either unsubstituted or substituted with one of the substituents selected from deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyrimidinyl; or a divalent benzofuran-pyrimidinyl group, either unsubstituted or substituted with one of the substituents selected from deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyrimidinyl.

[0114] According to an exemplary embodiment of this specification, HAr1 is a divalent triazine group that is unsubstituted or substituted with one of the following substituents: deuterium, phenyl, biphenyl, naphthyl, and pyrimidinyl; unsubstituted or substituted alkyl; phenyl, biphenyl, naphthyl, methyl, ethyl, propyl, propyl, and propyl. A divalent pyrimidinyl group substituted with one or both of the substituted pyridyl groups; a divalent quinazoline group that is unsubstituted or deuterated; a divalent benzothiophene-pyrimidinyl group that is unsubstituted or substituted with one of the following substituents: a phenyl group that is unsubstituted or deuterated or alkylated, a biphenyl group that is unsubstituted or deuterated or alkylated, a naphthyl group that is unsubstituted or deuterated or alkylated, and a pyrimidinyl group that is unsubstituted or deuterated or alkylated; or a divalent benzofuran-pyrimidinyl group that is unsubstituted or substituted with one of the following substituents: a phenyl group that is unsubstituted or deuterated or alkylated, a biphenyl group that is unsubstituted or deuterated or alkylated, a naphthyl group that is unsubstituted or deuterated or alkylated, and a pyrimidinyl group that is unsubstituted or deuterated or alkylated.

[0115] According to an exemplary embodiment of this specification, HAr1 is a divalent triazine group that is unsubstituted or substituted with one of the following substituents: deuterium, an unsubstituted or deuterated or alkyl-substituted phenyl group, an unsubstituted or deuterated or alkyl-substituted biphenyl group, an unsubstituted or deuterated or alkyl-substituted naphthyl group, and an unsubstituted or deuterated or alkyl-substituted pyrimidinyl group; or an unsubstituted or deuterated or alkyl-substituted biphenyl group. The following are divalent pyrimidinyl groups substituted with one or both of the following: unsubstituted or deuterated or alkyl-substituted naphthyl; unsubstituted or deuterated or alkyl-substituted methyl; unsubstituted or deuterated or alkyl-substituted ethyl; unsubstituted or deuterated or alkyl-substituted propyl; and unsubstituted or deuterated or alkyl-substituted pyridinyl; unsubstituted or deuterated divalent quinazolinyl; unsubstituted or deuterated divalent benzothiophenepyrimidinyl; or unsubstituted or deuterated divalent benzofuranopyrimidinyl.

[0116] According to an exemplary embodiment of this specification, HAr2 is a triazine group, either unsubstituted or substituted with two substituents selected independently of deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; a pyrimidinyl group, either unsubstituted or substituted with one to three substituents selected independently of deuterium, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; or an unsubstituted or substituted triazine group, substituted or substituted triazine group, substituted triazine group, and substituted triazine group having 6 to 60 carbon atoms, and substituted triazine group having 2 to 60 carbon atoms; or a pyrimidinyl group, either unsubstituted or substituted triazine group, substituted triazine group, and substituted triazine group having 6 to 60 carbon atoms, and substituted triazine group having 2 to 60 carbon atoms. A quinazolinyl group consisting of an unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a benzothiophene-pyrimidinyl group consisting of an unsubstituted or substituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a benzofuran-pyrimidinyl group consisting of an unsubstituted or substituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0117] According to an exemplary embodiment of this specification, HAr2 is a triazine group, either unsubstituted or substituted with two substituents selected independently of deuterium, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms; a pyrimidinyl group, either unsubstituted or substituted with one to three substituents selected independently of deuterium, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms; or an unsubstituted or substituted triazine group, substituted or un ... A quinazolinyl group consisting of an unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; a benzothiophene-pyrimidinyl group consisting of an unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; or a benzofuran-pyrimidinyl group consisting of an unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0118] According to an exemplary embodiment of this specification, HAr2 is a triazine group, either unsubstituted or substituted with two substituents selected independently of deuterium, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 20 carbon atoms; a pyrimidinyl group, either unsubstituted or substituted with one to three substituents selected independently of deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 20 carbon atoms; or an unsubstituted or substituted triazine group, substituted or substituted triazine group, substituted triazine group, and substituted triazine group having 6 to 20 carbon atoms, and substituted triazine group having 2 to 20 carbon atoms; or a pyrimidinyl group, either unsubstituted or substituted triazine group, substituted triazine group, and substituted triazine group having 6 to 20 carbon atoms, and substituted triazine group having 2 to 20 carbon atoms. A quinazolinyl group consisting of an unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; a benzothiophene-pyrimidinyl group consisting of an unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; or a benzofuran-pyrimidinyl group consisting of an unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0119] According to an exemplary embodiment of this specification, HAr2 is a triazine group, unsubstituted or substituted with two substituents selected independently of deuterium, substituted or unsubstituted aryl groups having 6 to 10 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 10 carbon atoms; a pyrimidinyl group, unsubstituted or substituted with one to three substituents selected independently of deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 10 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 10 carbon atoms; or an unsubstituted or substituted triazine group, substituted or substituted triazine group, substituted triazine group, and substituted triazine group having 6 to 10 carbon atoms, and substituted triazine group having 2 to 10 carbon atoms; or a pyrimidinyl group, unsubstituted or substituted triazine group, substituted triazine group, and substituted triazine group having 1 to 10 carbon atoms, and substituted triazine group having 6 to 10 carbon atoms, and substituted triazine group having 2 to 10 carbon atoms. A quinazolinyl group consisting of an unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms; a benzothiophene-pyrimidinyl group consisting of an unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms; or a benzofuran-pyrimidinyl group consisting of an unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

[0120] According to an exemplary embodiment of this specification, HAr2 is a triazine group, either unsubstituted or substituted with two substituents selected independently of deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyrimidinyl; or a pyrimidinyl group, either unsubstituted or substituted with one to three substituents selected independently of deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted pyridinyl; or a triazine group substituted with two substituents selected independently of deuterium, substituted phenyl, substituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted pyridinyl; or a triazine group substituted with one to three substituents selected from deuterium, substituted phenyl, substituted biphenyl, substituted naphthyl, substituted methyl, substituted ethyl, ... pyridinyl; or a triazine group substituted with one to three substituents selected from deuterium, substituted phenyl, substituted biphenyl, substituted naphthyl, substituted methyl, substituted ethyl, substituted propyl, and substituted pyridinyl; or a triazine group substituted with one to three substituents selected from deuterium, substituted phenyl, substituted biphenyl, substituted methyl, substituted ethyl, substituted propyl, and substituted pyridinyl; or a triazine group substituted with Quinazolinyl group substituted with one of the following substituents: a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and a substituted or unsubstituted naphthyl group; benzothiophene-pyrimidinyl group substituted with one of the following substituents: a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted pyrimidinyl group; or benzofuran-pyrimidinyl group substituted with one of the following substituents: a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted pyrimidinyl group.

[0121] According to an exemplary embodiment of this specification, HAr2 is a triazine group that is unsubstituted or substituted with two substituents selected independently of deuterium, unsubstituted or deuterated or alkyl-substituted phenyl, unsubstituted or deuterated or alkyl-substituted biphenyl, unsubstituted or deuterated or alkyl-substituted naphthyl, and unsubstituted or deuterated or alkyl-substituted pyrimidinyl; unsubstituted or substituted with two substituents selected independently of deuterium, unsubstituted or deuterated or alkyl-substituted phenyl, unsubstituted or deuterated or alkyl-substituted bi ... Pyrimidinyl groups substituted with one to three substituents from the following: alkyl-substituted biphenyl, unsubstituted or deuterated or alkyl-substituted naphthyl, unsubstituted or deuterated or alkyl-substituted methyl, unsubstituted or deuterated or alkyl-substituted ethyl, unsubstituted or deuterated or alkyl-substituted propyl, and unsubstituted or deuterated or alkyl-substituted pyridinyl; unsubstituted or deuterated or alkyl-substituted phenyl, unsubstituted or deuterated or alkyl-substituted biphenyl, and unsubstituted or deuterated or alkyl-substituted pyridinyl. A quinazolinyl group substituted with one of the following substituents: a naphthyl group substituted with deuterium or an alkyl group; a phenyl group substituted with one of the following substituents: an unsubstituted phenyl group substituted with deuterium or an alkyl group; a biphenyl group substituted with one of the following substituents: an unsubstituted naphthyl group substituted with deuterium or an alkyl group; a methyl group substituted with one of the following substituents: an ethyl group substituted with one of the following substituents: an ethyl group substituted with one of the following substituents: an unsubstituted propyl group substituted with one of the following substituents: an unsubstituted pyridyl ... The substituted benzothiophene-pyrimidinyl; or the benzofuran-pyrimidinyl, unsubstituted or substituted with one of the following: deuterium, unsubstituted or substituted with deuterium or alkyl, biphenyl, unsubstituted or substituted with deuterium or alkyl, naphthyl, unsubstituted or substituted with deuterium or alkyl, methyl, unsubstituted or substituted with deuterium or alkyl, ethyl, unsubstituted or substituted with deuterium or alkyl, propyl, and pyridinyl, unsubstituted or substituted with deuterium or alkyl.

[0122] According to one exemplary embodiment of this specification, L1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0123] According to one exemplary embodiment of this specification, L1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0124] According to one exemplary embodiment of this specification, L1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0125] According to an exemplary embodiment of this specification, L1 is a substituted or unsubstituted phenylene; a substituted or unsubstituted divalent biphenyl; a substituted or unsubstituted divalent triphenyl; a substituted or unsubstituted divalent naphthyl; a substituted or unsubstituted divalent anthraceneyl; or a substituted or unsubstituted divalent phenanthryl.

[0126] According to an exemplary embodiment of this specification, L1 is an unsubstituted or deuterated or alkyl-substituted phenylene; an unsubstituted or deuterated or alkyl-substituted diphenyl; an unsubstituted or deuterated or alkyl-substituted diphenyl; an unsubstituted or deuterated or alkyl-substituted dinaphthyl; an unsubstituted or deuterated or alkyl-substituted dianthryl; or an unsubstituted or deuterated or alkyl-substituted diphenyl.

[0127] According to an exemplary embodiment of this specification, L1 is an unsubstituted or deuterated, alkyl, or aryl substituted phenylene; an unsubstituted or deuterated, alkyl, or aryl substituted diphenyl; an unsubstituted or deuterated, alkyl, or aryl substituted diphenyl; an unsubstituted or deuterated, alkyl, or aryl substituted dinaphthyl; an unsubstituted or deuterated, alkyl, or aryl substituted dianthryl; or an unsubstituted or deuterated, alkyl, or aryl substituted diphenyl.

[0128] In one exemplary embodiment of this specification, L1 is represented by any of the following structural formulas.

[0129]

[0130]

[0131] The structure can be unsubstituted or deuterated, and

[0132] In structural formulas, dashed lines indicate bonding positions.

[0133] According to an exemplary embodiment of this specification, Ar1 is an aryl group having 6 to 60 carbon atoms that has one or more cyano groups and is optionally further deuterated.

[0134] According to an exemplary embodiment of this specification, Ar1 is an aryl group having 6 to 60 carbon atoms that has a cyano group and is optionally further deuterated.

[0135] According to an exemplary embodiment of this specification, Ar1 is an aryl group having 6 to 60 carbon atoms that has two cyano groups and is optionally further deuterated.

[0136] According to an exemplary embodiment of this specification, Ar1 is an aryl group having 6 to 60 carbon atoms that has one or two cyano groups and is optionally further deuterated.

[0137] According to an exemplary embodiment of this specification, Ar1 is an aryl group having three cyano groups and optionally further deuterated to have 6 to 60 carbon atoms.

[0138] According to an exemplary embodiment of this specification, Ar1 is an aryl group having 6 to 30 carbon atoms that has one or more cyano groups and is optionally further deuterated.

[0139] According to an exemplary embodiment of this specification, Ar1 is an aryl group having 6 to 20 carbon atoms that has one or more cyano groups and is optionally further deuterated.

[0140] According to an exemplary embodiment of this specification, Ar1 is an aryl group having 6 to 10 carbon atoms that has one or more cyano groups and is optionally further deuterated.

[0141] According to an exemplary embodiment of this specification, Ar1 is a phenyl group substituted with one or more cyano groups and optionally further substituted with deuterium; a naphthyl group substituted with one or more cyano groups and optionally further substituted with deuterium; a biphenyl group substituted with one or more cyano groups and optionally further substituted with deuterium; or a terphenyl group substituted with cyano groups and optionally further substituted with deuterium.

[0142] According to an exemplary embodiment of this specification, Ar1 is represented by any of the following structural formulas.

[0143]

[0144]

[0145]

[0146] The structure can be unsubstituted or deuterated, and

[0147] In structural formulas, dashed lines indicate bonding positions.

[0148] According to an exemplary embodiment of this specification, Ar21 to Ar23 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0149] According to one exemplary embodiment of this specification, Ar21 to Ar23 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0150] According to an exemplary embodiment of this specification, Ar21 to Ar23 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0151] According to an exemplary embodiment of this specification, Ar21 to Ar23 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted phenanthryl; or a substituted or unsubstituted anthraceneyl.

[0152] According to an exemplary embodiment of this specification, Ar21 to Ar23 may be the same as or different from each other, and each independently is an unsubstituted or deuterated or alkyl-substituted phenyl; an unsubstituted or deuterated or alkyl-substituted biphenyl; an unsubstituted or deuterated or alkyl-substituted terphenyl; an unsubstituted or deuterated or alkyl-substituted naphthyl; an unsubstituted or deuterated or alkyl-substituted phenanthryl; or an unsubstituted or deuterated or alkyl-substituted anthraceneyl.

[0153] According to an exemplary embodiment of this specification, Ar21 to Ar23 may be the same as or different from each other, and each is independently an unsubstituted or deuterated, alkyl or aryl substituted phenyl; an unsubstituted or deuterated, alkyl or aryl substituted biphenyl; an unsubstituted or deuterated, alkyl or aryl substituted terphenyl; an unsubstituted or deuterated, alkyl or aryl substituted naphthyl; an unsubstituted or deuterated, alkyl or aryl substituted phenanthryl; or an unsubstituted or deuterated, alkyl or aryl substituted anthracene.

[0154] According to an exemplary embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0155] According to one exemplary embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently hydrogen or deuterium.

[0156] According to an exemplary embodiment of this specification, both R1 and R2 are deuterium.

[0157] According to one exemplary embodiment of this specification, R1 and R2 are both hydrogen.

[0158] According to an exemplary embodiment of this specification, chemical formula 1 is any one of the following chemical formulas 1-A to 1-C.

[0159] [Chemical Formula 1-A]

[0160]

[0161] [Chemical Formula 1-B]

[0162]

[0163] [Chemical Formula 1-C]

[0164]

[0165] In chemical formulas 1-A to 1-C,

[0166] HAr1, HAr2, L1, Ar1, Ar21 to Ar23, R1, R2, n and m are the same as those defined in Formula 1, and a1 to a3 are 1.

[0167] According to an exemplary embodiment of this specification, chemical formula 1-3 is either chemical formula 1-3-1 or 1-3-2.

[0168] [Chemical Formula 1-3-1]

[0169]

[0170] [Chemical Formula 1-3-2]

[0171]

[0172] In chemical formulas 1-3-1 and 1-3-2,

[0173] Ar1, Ar21 to Ar23, HAr2, L1, R1, R2, a1 to a3, m and n are the same as those defined in chemical formulas 1-3.

[0174] According to an exemplary embodiment of this specification, chemical formula 1-4 is either chemical formula 1-4-1 or 1-4-2.

[0175] [Chemical Formula 1-4-1]

[0176]

[0177] [Chemical Formula 1-4-2]

[0178]

[0179] In chemical formulas 1-4-1 and 1-4-2,

[0180] Ar1, Ar21 to Ar23, HAr2, L1, R1, R2, a1 to a3, m and n are the same as those defined in chemical formulas 1-4.

[0181] According to an exemplary embodiment of this specification, chemical formula 1-5 is either chemical formula 1-5-1 or 1-5-2.

[0182] [Chemical Formula 1-5-1]

[0183]

[0184] [Chemical Formula 1-5-2]

[0185]

[0186] In chemical formulas 1-5-1 and 1-5-2,

[0187] Ar1, Ar21 to Ar23, HAr2, L1, R1, R2, a1 to a3, m and n are the same as those defined in chemical formulas 1-5.

[0188] In this specification, chemical formula 1-3 refers to the above chemical formula 1-3-1.

[0189] In this specification, chemical formula 1-3 is chemical formula 1-3-2 above.

[0190] In this specification, chemical formula 1-4 refers to the above chemical formula 1-4-1.

[0191] In this specification, chemical formula 1-4 is chemical formula 1-4-2 above.

[0192] In this specification, chemical formula 1-5 refers to the above chemical formula 1-5-1.

[0193] In this specification, chemical formula 1-5 refers to the above chemical formula 1-5-2.

[0194] According to an exemplary embodiment of this specification, R3 is deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0195] According to an exemplary embodiment of this specification, R3 is deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0196] According to an exemplary embodiment of this specification, R3 is deuterium; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0197] According to an exemplary embodiment of this specification, R3 is deuterium; a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

[0198] According to an exemplary embodiment of this specification, R3 is deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; or substituted or unsubstituted pyridyl.

[0199] According to an exemplary embodiment of this specification, R3 is deuterium; an unsubstituted or deuterated, methyl, or pyrimidinium-substituted phenyl group; an unsubstituted or deuterated, methyl, or pyrimidinium-substituted biphenyl group; an unsubstituted or deuterated, methyl, or pyrimidinium-substituted naphthyl group; or an unsubstituted or deuterated, methyl, or pyrimidinium-substituted pyridyl group.

[0200] According to an exemplary embodiment of this specification, R4 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0201] According to an exemplary embodiment of this specification, R4 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0202] According to an exemplary embodiment of this specification, R4 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0203] According to an exemplary embodiment of this specification, R4 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

[0204] According to an exemplary embodiment of this specification, R4 is hydrogen; deuterium; methyl; ethyl; propyl; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; or substituted or unsubstituted pyridyl.

[0205] According to an exemplary embodiment of this specification, R4 is hydrogen; deuterium; methyl; ethyl; propyl; unsubstituted or deuterated or alkyl-substituted phenyl; unsubstituted or deuterated or alkyl-substituted biphenyl; unsubstituted or deuterated or alkyl-substituted naphthyl; or unsubstituted or deuterated or alkyl-substituted pyridyl.

[0206] According to one exemplary embodiment of this specification, n is an integer from 1 to 4.

[0207] According to one exemplary embodiment of this specification, n is 1.

[0208] According to one exemplary embodiment of this specification, n is 2.

[0209] According to one exemplary embodiment of this specification, n is 3.

[0210] According to one exemplary embodiment of this specification, n is 4.

[0211] According to one exemplary embodiment of this specification, m is an integer from 1 to 3.

[0212] According to one exemplary embodiment of this specification, m is 1.

[0213] According to one exemplary embodiment of this specification, m is 2.

[0214] According to one exemplary embodiment of this specification, m is 3.

[0215] According to one exemplary embodiment of this specification, o is 1 or 2.

[0216] According to one exemplary embodiment of this specification, o is 1.

[0217] According to one exemplary embodiment of this specification, o is 2.

[0218] According to one exemplary embodiment of this specification, a1 is 0 or 1.

[0219] According to one exemplary embodiment of this specification, a1 is 0.

[0220] According to one exemplary embodiment of this specification, a1 is 1.

[0221] According to one exemplary embodiment of this specification, a2 is 0 or 1.

[0222] According to one exemplary embodiment of this specification, a2 is 0.

[0223] According to one exemplary embodiment of this specification, a2 is 1.

[0224] According to one exemplary embodiment of this specification, a3 is 0 or 1.

[0225] According to one exemplary embodiment of this specification, a3 is 0.

[0226] According to one exemplary embodiment of this specification, a3 is 1.

[0227] According to one exemplary embodiment of this specification, chemical formula 1 is any of the following structural formulas.

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is 30% or greater.

[0236] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is 40% or greater.

[0237] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is 50% or greater.

[0238] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is 60% or greater.

[0239] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is 70% or greater.

[0240] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is 80% or greater.

[0241] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is 90% or greater.

[0242] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is 100%.

[0243] Substituents of compounds of Formula 1 can be bonded by methods known in the art, and the type and position of substituents or the number of substituents can be varied according to techniques known in the art.

[0244] Furthermore, various substituents can be introduced into the core structure having the above-described structure to synthesize compounds with the inherent properties of the introduced substituents. For example, substituents commonly used in hole injection layer materials, hole transport materials, light-emitting layer materials, and electron transport layer materials for manufacturing organic light-emitting devices can be introduced into the core structure to synthesize materials that meet the requirements of each organic material layer.

[0245] Furthermore, the organic light-emitting device according to the present invention comprises: a first electrode; a second electrode disposed facing the first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain the aforementioned compound.

[0246] The organic light-emitting device of the present invention can be manufactured using typical manufacturing methods and materials for organic light-emitting devices, except that the above-mentioned compound is used to form an organic material layer having one or more layers.

[0247] When manufacturing organic light-emitting devices, the compound can be formed into an organic material layer not only by vacuum deposition but also by solution coating. In this document, solution coating refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, etc., but is not limited to these.

[0248] The organic material layer of the organic light-emitting device of the present invention can be a single-layer structure, or it can be a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention can have a structure comprising a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting holes, a light-emitting layer, an electron transport layer, an electron injection layer, etc., as organic material layers. However, the structure of the organic light-emitting device is not limited to this, and it can include fewer or more organic material layers.

[0249] In the organic light-emitting device of the present invention, the organic material layer may include one or more layers of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and one or more of the layers may contain a compound represented by chemical formula 1.

[0250] In another organic light-emitting device, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer may contain a compound represented by chemical formula 1.

[0251] In the organic light-emitting device of the present invention, the electron injection and transport layer comprises a compound of chemical formula 1 and a metal complex.

[0252] In the organic light-emitting device of the present invention, the organic material layer may include one or more layers such as a hole injection layer, a hole transport layer, and a layer that simultaneously injects and transports holes, and one or more of the layers may contain a compound represented by chemical formula 1.

[0253] In yet another organic light-emitting device, the organic material layer may include a hole injection layer or a hole transport layer, and the hole transport layer or hole injection layer may contain a compound represented by chemical formula 1.

[0254] In one exemplary embodiment of this specification, the first electrode is an anode and the second electrode is a cathode.

[0255] According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

[0256] (1) Anode / hole transport layer / light-emitting layer / cathode

[0257] (2) Anode / hole injection layer / hole transport layer / light emission layer / cathode

[0258] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0259] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0260] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0261] (6) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / cathode

[0262] (7) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0263] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / cathode

[0264] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0265] (10) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0266] (11) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0267] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emission layer / electron transport layer / cathode

[0268] (13) Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0269] (14) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0270] (15) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0271] (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0272] (17) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0273] (18) Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron injection and transport layer / Cathode

[0274] (19) Anode / hole injection layer / hole transport layer / light emission layer / electron injection and transport layer / cathode

[0275] (20) Anode / Hole injection layer / First hole transport layer / Second hole transport layer / Light emission layer / Electron injection and transport layer / Cathode

[0276] The organic light-emitting device of the present invention can have the following structure: Figure 1 and Figure 3 The structures shown are examples of, but not limited to, those described.

[0277] Figure 1 An example is shown of an organic light-emitting device in which an anode 2, an organic material layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In the above structure, a compound represented by chemical formula 1 may be included in the organic material layer 3.

[0278] Figure 2 An example is shown of an organic light-emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, an electron injection and transport layer 9, and a cathode 4 are sequentially stacked on a substrate 1. A compound represented by chemical formula 1 may be included in the electron injection and transport layer 9.

[0279] Figure 3 An example is shown of an organic light-emitting device in which an anode 2, a hole injection layer 5, a first hole transport layer 6-1, a second hole transport layer 6-2, an electron blocking layer 7, a light-emitting layer 8, an electron injection and transport layer 9, and a cathode 4 are sequentially stacked on a substrate 1. A compound represented by chemical formula 1 may be included in the electron injection and transport layer 9.

[0280] For example, the organic light-emitting device according to the present invention can be manufactured by depositing a metal or a conductive metal oxide or alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation to form an anode; forming an organic material layer on the anode having one or more layers selected from a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons; and then depositing a material that can be used as a cathode on the organic material layer. In addition to the methods described above, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0281] The organic material layer can have a multilayer structure including, but is not limited to, a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and can also have a single-layer structure. Furthermore, various polymer materials can be used to manufacture the organic material layer into a smaller number of layers using methods such as solvent methods (e.g., spin coating, dip coating, doctor blade coating, screen printing, inkjet printing) or thermal transfer methods instead of deposition methods.

[0282] The anode is the electrode for injecting holes, and as the anode material, a material with a high work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of anode materials that can be used in this invention 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); and combinations of metals and oxides, such as... or Conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline; etc., but not limited thereto.

[0283] The cathode is the electrode into which electrons are injected, and as a cathode material, a material with a low work function is generally preferred to facilitate the injection of electrons into the organic material layer. Specific examples of cathode materials 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… or ; and so on, but not limited to these.

[0284] The hole injection layer is a layer that facilitates the injection of holes from the anode into the light-emitting layer. The hole injection material is preferably a material capable of effectively receiving holes from the anode at low voltages, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. Specific examples of hole injection materials include metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile-based hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, and others. Organic materials, anthraquinone, conductive polymers based on polyaniline and polythiophene, etc., but not limited to these. The thickness of the hole injection layer can be from 1 nm to 150 nm. When the thickness of the hole injection layer is 1 nm or greater, there is an advantage in preventing the degradation of hole injection characteristics. When the thickness of the hole injection layer is 150 nm or less, there is an advantage in preventing the increase of the driving voltage to improve hole movement due to the hole injection layer being too thick.

[0285] According to one exemplary embodiment of this specification, the hole injection layer may be a compound with the following chemical formula HI-1.

[0286] [Chemical formula HI-1]

[0287]

[0288] In the chemical formula HI-1,

[0289] R201 to R204 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, or bonded to an adjacent group to form a substituted or unsubstituted ring, and

[0290] In one exemplary embodiment of this specification, R201 to R204 may be the same as or different from each other, and are substituted or unsubstituted alkyl groups; substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups, or bonded to adjacent groups to form substituted or unsubstituted rings.

[0291] In one exemplary embodiment of this specification, R201 to R204 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0292] In one exemplary embodiment of this specification, R201 to R204 may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0293] In one exemplary embodiment of this specification, R201 to R204 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0294] In one exemplary embodiment of this specification, R202 and R204 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group.

[0295] In one exemplary embodiment of this specification, R201 and R203 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0296] In one exemplary embodiment of this specification, R201 and R203 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0297] In one exemplary embodiment of this specification, R201 and R203 may be the same as or different from each other, and each may be independently a substituted or unsubstituted phenyl group.

[0298] In one exemplary embodiment of this specification, R202 and R204 may be the same as or different from each other, and each is independently a substituted or unsubstituted heteroaryl group.

[0299] In one exemplary embodiment of this specification, R202 and R204 may be the same as or different from each other, and each is independently a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0300] In one exemplary embodiment of this specification, R202 and R204 may be the same as or different from each other, and each is independently a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

[0301] In one exemplary embodiment of this specification, R202 and R204 may be the same as or different from each other, and each is independently a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted dibenzothiophenyl; or a substituted or unsubstituted carbazoleyl.

[0302] In one exemplary embodiment of this specification, R202 and R204 may be the same as or different from each other, and each is independently an unsubstituted or aryl-substituted carbazolyl group.

[0303] In one exemplary embodiment of this specification, R202 and R204 may be the same as or different from each other, and each is independently an unsubstituted or phenyl-substituted carbazole group.

[0304] In one exemplary embodiment of this specification, the chemical formula HI-1 is represented by the following compound.

[0305]

[0306] The hole transport layer can perform the function of smoothly transporting holes. Suitable hole transport materials are those with high hole mobility that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0307] According to one exemplary embodiment of this specification, the hole transport layer comprises, but is not limited to, a compound with the chemical formula HT-1.

[0308] [Chemical formula HT-1]

[0309]

[0310] In the chemical formula HT-1,

[0311] to At least one of them is N, and the rest are CH, and

[0312] R309 to R314 may be the same as or different from each other, and each is independently hydrogen; deuterium; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, or bonded to an adjacent group to form a substituted or unsubstituted ring.

[0313] According to an exemplary embodiment of this specification to Let N be the number of elements in the array.

[0314] According to an exemplary embodiment of this specification, R309 to R314 are cyano groups.

[0315] According to one exemplary embodiment of this specification, chemical formula HT-1 may include the following compounds.

[0316]

[0317] According to one exemplary embodiment of this specification, the hole transport layer comprises, but is not limited to, a compound represented by the chemical formula HT-2.

[0318] [Chemical formula HT-2]

[0319]

[0320] In the chemical formula HT-2,

[0321] R315 to R317 may be the same as or different from each other, and each is independently selected from hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; and combinations thereof, or bonded to adjacent groups to form substituted or unsubstituted rings.

[0322] r315 is an integer from 1 to 5, and when r315 is 2 or greater, two or more R315s are the same or different from each other.

[0323] r316 is an integer from 1 to 5, and when r316 is 2 or greater, two or more R316 are the same or different from each other.

[0324] According to an exemplary embodiment of this specification, R317 is selected from any of the following: substituted or unsubstituted aryl groups; substituted or unsubstituted heteroaryl groups; and combinations thereof.

[0325] According to an exemplary embodiment of this specification, R317 is a substituted or unsubstituted phenyl group; or a substituted or unsubstituted fluorenyl group; or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

[0326] According to one exemplary embodiment of this specification, R317 is an unsubstituted or alkyl- or aryl-substituted fluorenyl group.

[0327] According to one exemplary embodiment of this specification, R315 and R316 may be the same as or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted carbazole group.

[0328] According to one exemplary embodiment of this specification, R315 and R316 may be the same as or different from each other, and each is independently hydrogen; deuterium; phenyl; or unsubstituted or biphenyl-substituted carbazole group.

[0329] According to one exemplary embodiment of this specification, the chemical formula HT-2 is represented by the following compound.

[0330]

[0331] According to one exemplary embodiment of this specification, the hole transport layer may comprise a compound of chemical formula HT-1 and / or a compound of chemical formula HT-2.

[0332] According to an exemplary embodiment of this specification, the hole transport layer may consist of a first hole transport layer and a second hole transport layer.

[0333] According to one exemplary embodiment of this specification, the first hole transport layer may comprise a compound of the chemical formula HT-1.

[0334] According to one exemplary embodiment of this specification, the second hole transport layer may comprise a compound of the chemical formula HT-2.

[0335] An electron blocking layer may be disposed between the hole transport layer and the light-emitting layer. The spirocyclic compound described above or other materials known in the art can be used as the electron blocking layer.

[0336] The luminescent layer can emit red, green, or blue light and can be composed of phosphorescent or fluorescent materials. The luminescent material is capable of receiving and combining holes and electrons from the hole transport layer and electron transport layer, respectively, to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include: 8-hydroxy-quinoline aluminum complexes (… ); Carbazole-based compounds; Dipolystyrene-based compounds; ; 10-hydroxybenzoquinoline-metal compounds; based on benzoquinoline Zyrazoles, benzothiazole-based and benzimidazole-based compounds; polymers based on poly(p-phenylenevinylene) (PPV); spirocyclic compounds; polyfluorene; red fluorene; etc., but not limited to these.

[0337] Examples of host materials used for the luminescent layer include fused aromatic ring derivatives or heterocyclic compounds. Specifically, examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, and fluoranthene compounds, while examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but are not limited to these examples.

[0338] According to one exemplary embodiment of this specification, the body comprises, but is not limited to, a compound of the following chemical formula H-1.

[0339] [Chemical formula H-1]

[0340]

[0341] In chemical formula H-1,

[0342] L20 and L21 may be the same as or different from each other, and each is independently a direct bond; a substituted or unsubstituted aryl group; or a substituted or unsubstituted divalent heterocyclic group.

[0343] Ar20 and Ar21 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group.

[0344] R201 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0345] r201 is an integer from 1 to 8, and when r201 is 2 or greater, two or more R201s are the same or different from each other.

[0346] In one exemplary embodiment of this specification, L20 and L21 may be the same as or different from each other, and each is independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

[0347] In one exemplary embodiment of this specification, L20 and L21 may be the same as or different from each other, and each is independently a direct bond; an unsubstituted or deuterated phenylene; an unsubstituted or deuterated biphenylene; an unsubstituted or deuterated naphthylene; a divalent dibenzofuranyl; or a divalent dibenzothiopheneyl.

[0348] In one exemplary embodiment of this specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[0349] In one exemplary embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0350] In one exemplary embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

[0351] In one exemplary embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each is independently a phenyl group that is unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group that is unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group that is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a biphenyl group that is unsubstituted or substituted with a biphenyl group having 6 to 30 carbon atoms. Thiophene group substituted with monocyclic or polycyclic aryl groups; dibenzofuran group substituted with monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms; naphthobenzofuran group substituted with monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms; dibenzothiophene group substituted with monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms; or naphthobenzothiophene group substituted with monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms.

[0352] In one exemplary embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each independently represents an unsubstituted or deuterated phenyl group; an unsubstituted or deuterated biphenyl group; a terphenyl group; an unsubstituted or deuterated naphthyl group; an unsubstituted or phenyl-substituted thiophene group; a phenanthryl group; a dibenzofuranyl group; a naphthobenzofuranyl group; a dibenzothiophene group; or a naphthobenzothiophene group.

[0353] In one exemplary embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each is independently phenyl, 1-naphthyl, or 2-naphthyl.

[0354] According to one exemplary embodiment of this specification, R201 is hydrogen or naphthyl.

[0355] According to one exemplary embodiment of this specification, chemical formula H-1 may include the following compounds.

[0356]

[0357] When the emitting layer emits red light, phosphorescent materials such as bis(1-phenylisoquinoline) iridium acetylacetonate (PIQIr(acac)), bis(1-phenylquinoline) iridium acetylacetonate (PQIr(acac)), tris(1-phenylquinoline) iridium (PQIr), or octaethylporphyrin platinum (PtOEP) can be used, or fluorescent materials such as tris(8-hydroxyquinoline) aluminum ( Phosphorescent dopants can be used, however, they are not limited to this. When the emitting layer emits green light, phosphorescent materials such as planar tris(2-phenylpyridine)iridium (P-I) can be used. ) or fluorescent materials such as tris(8-hydroxyquinoline)aluminum ( Phosphorescent materials can be used as luminescent dopants, but are not limited to this. When the luminescent layer emits blue light, phosphorescent materials such as... Alternatively, fluorescent materials such as spiro-DPVBi, spiro-6P, stilbene (DSB), stilbene arylene (DSA), PFO-based polymers, or PPV-based polymers may be used as luminescent dopants; however, luminescent dopants are not limited to these.

[0358] In one exemplary embodiment of this specification, the dopant comprises a compound with the following chemical formula D-1.

[0359] [Chemical Formula D-1]

[0360]

[0361] In chemical formula D-1,

[0362] R101 to R104 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; substituted or unsubstituted heterocyclic; or substituted or unsubstituted silyl.

[0363] L401 and L402 may be identical or different from each other, and each is independently a direct bond; or a substituted or unsubstituted aryl group.

[0364] R401 to R404 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group.

[0365] r1 to r4 are integers from 0 to 2, and

[0366] When r1 to r4 are 2 or greater, R101 to R104 in each bracket are either the same or different from each other.

[0367] In one exemplary embodiment of this specification, R101 to R104 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted silyl.

[0368] In one exemplary embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted silyl.

[0369] In one exemplary embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; or unsubstituted or alkyl-substituted silyl.

[0370] In one exemplary embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently hydrogen; deuterium; or unsubstituted or methyl-substituted silyl group.

[0371] In one exemplary embodiment of this specification, R103 and R104 may be the same as or different from each other, and each is independently hydrogen; or deuterium.

[0372] In one exemplary embodiment of this specification, L401 and L402 are each direct keys.

[0373] In one exemplary embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0374] In one exemplary embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic aryl; or a substituted or unsubstituted polycyclic aryl; or a substituted or unsubstituted heterocyclic group.

[0375] In one exemplary embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted anthraquinyl; a substituted or unsubstituted phenanthryl; a substituted or unsubstituted triphenylene; a substituted or unsubstituted pyrene; or a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiopheneyl.

[0376] In one exemplary embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; or a substituted or unsubstituted dibenzofuranyl.

[0377] In one exemplary embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently a phenyl substituted with one or more of an unsubstituted or substituted alkyl, a substituted or unsubstituted silyl, or a substituted or unsubstituted aryl.

[0378] In one exemplary embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently a phenyl group that is unsubstituted or substituted with one or more substituents selected from methyl, tert-butyl, propyl, isopropyl, trimethylsilyl, cyano, and unsubstituted or alkyl-substituted phenyl groups.

[0379] In one exemplary embodiment of this specification, chemical formula D-1 is represented by the following compound.

[0380]

[0381] A hole blocking layer may be disposed between the electron transport layer and the light-emitting layer, and materials known in the art may be used.

[0382] The electron transport layer performs the function of smoothly transporting electrons. Suitable electron transport materials are those with high electron mobility that can effectively receive electrons from the cathode and transfer them to the emitting layer. Specific examples include: Al complexes of 8-hydroxyquinoline; containing... Complexes; organic free radical compounds; hydroxyflavonoid-metal complexes; etc., but not limited to these. The thickness of the electron transport layer can be from 1 nm to 50 nm. When the thickness of the electron transport layer is 1 nm or greater, there is an advantage in preventing the degradation of electron transport properties. When the thickness of the electron transport layer is 50 nm or less, there is an advantage in preventing the increase of the driving voltage to improve electron movement due to the electron transport layer being too thick.

[0383] The electron injection layer can perform the function of smoothly injecting electrons. Preferred electron injection materials are compounds that possess the ability to transport electrons, the effect of injecting electrons from the cathode, and an excellent effect of injecting electrons into the light-emitting layer or light-emitting material, preventing excitons generated by the light-emitting layer from migrating to the hole injection layer, and also exhibiting excellent thin film formation capabilities. Specific examples include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, diazole, triazole, imidazole, Tetracarboxylic acids, fluorenemethane, anthrone, and their derivatives; metal complexes; nitrogen-containing 5-membered ring derivatives; and so on, but not limited to these.

[0384] Electron injection and transport layers can be fabricated by appropriately selecting the materials used for the electron injection and electron transport layers.

[0385] The electron injection and transport layer can be fabricated using a compound of chemical formula 1.

[0386] Electron injection and transport layers can be fabricated using compounds of Formula 1 and metal complexes together.

[0387] The electron injection and transport layer comprises compounds of Formula 1 and metal complexes in a weight ratio of 1:10 to 10:1.

[0388] The electron injection and transport layer comprises a compound of formula 1 and a metal complex in a weight ratio of 1:3 to 3:1.

[0389] Metal complex compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)chlorogallium, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc., but are not limited to these.

[0390] A hole blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed under the same conditions as a hole injection layer. Specific examples may include... Diazole derivatives, triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc., but not limited to these.

[0391] Depending on the material to be used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a dual-emitting type.

[0392] The organic light-emitting device of the present invention can be manufactured using typical manufacturing methods and materials for organic light-emitting devices, except that the above-mentioned compound is used to form an organic material layer having one or more layers.

[0393] [Preparation Example]

[0394] Preparation Example 1-1: Preparation of Compound E1

[0395]

[0396] E1-A (20 g, 38.4 mmol) and E1-B (16.7 g, 38.4 mmol) were placed in 400 ml of 1,4-dioxanone under a nitrogen atmosphere. The mixture was stirred and refluxed in alkane. Tripotassium phosphate (24.4 g, 115.2 mmol) was then dissolved in 24 mL of water, and the resulting solution was introduced into the mixture. The mixture was stirred thoroughly, and then palladium dibenzylacetone (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.6 g, 2.3 mmol) were introduced. After 6 hours of reaction, the product was cooled to room temperature, and the resulting solid was filtered. The solid was added to 900 mL of chloroform and dissolved therein. The solution was washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added to the solution, and the resulting mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare E1 (4.6 g, 15%), a yellow solid. ).

[0397] Preparation Example 1-2: Preparation of Compound E2

[0398]

[0399] Compound E2 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0400]

[0401] Preparation Examples 1-3: Preparation of Compound E3

[0402]

[0403] Compound E3 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0404]

[0405] Preparation Examples 1-4: Preparation of Compound E4

[0406]

[0407] Compound E4 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0408]

[0409] Preparation Examples 1-5: Preparation of Compound E5

[0410]

[0411] Compound E5 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0412]

[0413] Preparation Examples 1-6: Preparation of Compound E6

[0414]

[0415] Compound E6 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0416]

[0417] Preparation Examples 1-7: Preparation of Compound E7

[0418]

[0419] Compound E7 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0420]

[0421] Preparation Examples 1-8: Preparation of Compound E8

[0422]

[0423] Compound E8 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0424]

[0425] Preparation Examples 1-9: Preparation of Compound E9

[0426]

[0427] Compound E9 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0428]

[0429] Preparation Examples 1-10: Preparation of Compound E10

[0430]

[0431] Compound E10 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0432]

[0433] Preparation Examples 1-11: Preparation of Compound E11

[0434]

[0435] Compound E11 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0436]

[0437] Preparation Examples 1-12: Preparation of Compound E12

[0438]

[0439] Compound E12 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0440]

[0441] Preparation Examples 1-13: Preparation of Compound E13

[0442]

[0443] Compound E13 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0444]

[0445] Preparation Examples 1-14: Preparation of Compound E14

[0446]

[0447] Compound E14 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0448]

[0449] Preparation Examples 1-15: Preparation of Compound E15

[0450]

[0451] Compound E15 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0452]

[0453] Preparation Examples 1-16: Preparation of Compound E16

[0454]

[0455] Compound E16 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0456]

[0457] Preparation Examples 1-17: Preparation of Compound E17

[0458]

[0459] Compound E17 was prepared in the same manner as in Preparation Example 1-1, except that the starting materials were used as in the reaction scheme.

[0460]

[0461] [Example]

[0462] Example 1-1

[0463] A thin coating with a thickness of A glass substrate of tin oxide (ITO) was immersed in distilled water containing a cleaning agent and ultrasonically washed. In this case, a product manufactured by Fischer Co. was used as the cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice for 10 minutes each time using distilled water. After washing with distilled water, ultrasonic washing was performed using isopropanol, acetone, and methanol solvents, and the resulting product was dried and then transported to a plasma cleaner. Furthermore, the substrate was cleaned using oxygen plasma for 5 minutes before being transported to a vacuum depositor.

[0464] The following compound HI-A was thermally vacuum deposited onto the prepared transparent ITO electrode to a thickness of [thickness value missing]. This forms a hole injection layer. Compounds HAT and HT-A are sequentially vacuum-deposited onto the hole injection layer to thicknesses of [thickness values ​​to be specified]. and This forms the first hole transport layer and the second hole transport layer.

[0465] Subsequently, compounds BH and BD were vacuum deposited on the second hole transport layer at a weight ratio of 25:1 until the film thickness was [missing information]. This forms a light-emitting layer.

[0466] Previously prepared compound E1 and the following compound LiQ were vacuum deposited on the luminescent layer at a 1:1 weight ratio, thereby forming a layer with a thickness of [missing information]. Electron injection and transport layers were constructed. Lithium fluoride (LiF) and aluminum were sequentially deposited on the electron injection and transport layers to thicknesses of [thickness values ​​missing]. and This forms the cathode.

[0467]

[0468] In the aforementioned process, the deposition rate of organic materials is maintained at / seconds / second, maintaining the deposition rates of lithium fluoride and aluminum at the cathode at respectively / second and / second, and maintaining the vacuum level during deposition. Entrust to This allows for the fabrication of organic light-emitting devices.

[0469] Examples 1-2 to 1-17

[0470] Organic light-emitting devices were manufactured in the same manner as in Examples 1-1, except that compounds E2 to E17 described in Table 1 below were used instead of compound E1 in Examples 1-1.

[0471] Comparative Examples 1-1 to 1-11

[0472] Organic light-emitting devices were manufactured in the same manner as in Examples 1-1, except that compounds ET-1 to ET-11 from Table 1 below were used instead of compound E1 in Examples 1-1. The structures of compounds ET-1 to ET-11 in Table 1 below are as follows.

[0473]

[0474] [Experimental Example]

[0475] For the organic light-emitting devices manufactured in Examples 1-1 to 1-17 and Comparative Examples 1-1 to 1-11, in The driving voltage and luminous efficiency were measured at current density, and... The time (T90) for the light intensity to reach 90% of the initial brightness was measured at a given current density. The results are shown in Table 1 below.

[0476] [Table 1]

[0477]

[0478] As shown in Table 1 above, compared with Comparative Examples 1-1 to 1-11, the organic light-emitting devices of Examples 1-1 to 1-17, in which compounds represented by Chemical Formula 1 according to this specification are used in the electron injection and electron transport layers of the organic light-emitting device, exhibit low driving voltage and excellent characteristics in terms of efficiency and / or lifetime.

[0479] Specifically, compounds ET-1 to ET-5 differ from the compounds of Formula 1 of this application in that they do not have a linking group corresponding to L in Formula 1 of this application; compounds ET-6 and ET-7 differ from the compounds of Formula 1 of this application in that they do not have aryl groups corresponding to Ar21 to Ar23 in Formula 1 of this application; compounds ET-8 and ET-9 differ from the compounds of Formula 1 of this application in that they do not have aryl groups substituted with cyano groups corresponding to Ar1 in Formula 1 of this application; compound ET-10 differs from the compounds of Formula 1 of this application in that the aryl groups of Ar21 to Ar23 in Formula 1 of this application have different substituent positions; and compound ET-11 differs from the compounds of Formula 1 of this application in that it does not have -CN (cyano).

[0480] As described above, Comparative Examples 1-1 to 1-11 using compounds ET-1 to ET-11 exhibit higher driving voltage, lower efficiency, and / or lower lifetime characteristics than Examples 1-1 to 1-17 using compounds of Formula 1 of this application due to the reduced electron mobility caused by the increased energy barrier with the light-emitting layer.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] ， in, In chemical formula 1, HAr1 is a divalent triazine group, either unsubstituted or substituted with one of the following substituents: deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; or a divalent triazine group, either unsubstituted or substituted with one or two substituents, each independently selected from deuterium, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms. Pyrimidinyl; an unsubstituted or deuterated divalent quinazolinyl; an unsubstituted or substituted divalent benzothiophene-pyrimidinyl with a substituent selected from deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; or an unsubstituted or substituted divalent benzofuran-pyrimidinyl with a substituent selected from deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms. HAr2 is a triazine group, either unsubstituted or substituted with two substituents selected independently of deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; or a pyrimidinyl group, either unsubstituted or substituted with one to three substituents selected independently of deuterium, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; or an unsubstituted or substituted triazine group, either substituted or substituted with one to three substituents selected independently of deuterium, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, and substituted aryl groups having 6 to 60 carbon atoms. A quinazolinyl group consisting of an aryl group having 2 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted; a benzothiophene-pyrimidinyl group consisting of an unsubstituted or substituted aryl group having 6 to 60 carbon atoms, substituted or unsubstituted, or a heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted; or a benzofuran-pyrimidinyl group consisting of an unsubstituted or substituted aryl group having 6 to 60 carbon atoms, substituted or unsubstituted, or a heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted. L1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms. Ar1 is an aryl group having 6 to 60 carbon atoms that has one or more cyano groups and is optionally further deuterated. Ar21 to Ar23 may be the same as or different from each other, and each is independently hydrogen; deuterium; or aryl groups with 6 to 60 carbon atoms, substituted or unsubstituted. R1 and R2 may be the same as or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. n is an integer from 1 to 4, and when n is 2 or greater, R1 is either the same or different from each other. m is an integer from 1 to 3, and when m is 2 or greater, R² are either the same or different from each other. a1, a2, and a3 are each 0 or 1. ,as well as 。 2. The compound according to claim 1, wherein chemical formula 1 is any one of the following chemical formulas 1-1 to 1-5: ， [Chemical Formula 1-2] ， [Chemical Formulas 1-3] ， [Chemical Formulas 1-4] ， [Chemical Formulas 1-5] ， In chemical formulas 1-1 to 1-5, HAr2, L1, Ar1, Ar21 to Ar23, n, m, and a1 to a3 are the same as those defined in Chemical Formula 1. R1 and R2 may be the same as or different from each other, and each may independently be hydrogen or deuterium. R3 is deuterium; an aryl group with 6 to 60 carbon atoms, substituted or unsubstituted; or a heteroaryl group with 2 to 60 carbon atoms, substituted or unsubstituted. R4 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms. o is 1 or 2, and When o is 2, R4 are either the same or different from each other.

3. The compound according to claim 1, wherein Ar1 is a phenyl group substituted with one or more cyano groups and optionally further substituted with deuterium; a naphthyl group substituted with one or more cyano groups and optionally further substituted with deuterium; a biphenyl group substituted with one or more cyano groups and optionally further substituted with deuterium; or a terphenyl group substituted with one or more cyano groups and optionally further substituted with deuterium.

4. The compound according to claim 1, wherein HAr1 is a divalent triazine group substituted with one of the following substituents: deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyrimidinyl; unsubstituted or substituted with one of the following substituents: deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted pyridyl. A divalent pyrimidinyl group substituted with one or two substituents; a divalent quinazolinyl group, either unsubstituted or deuterated; a divalent benzothiophene-pyrimidinyl group, either unsubstituted or substituted with a substituent selected from deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyrimidinyl; or a divalent benzofuran-pyrimidinyl group, either unsubstituted or substituted with a substituent selected from deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyrimidinyl.

5. The compound according to claim 1, wherein Ar21 to Ar23 are the same or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted phenanthryl; or a substituted or unsubstituted anthraceneyl.

6. The compound according to claim 1, wherein L1 is a substituted or unsubstituted phenylene; a substituted or unsubstituted divalent biphenyl; a substituted or unsubstituted divalent triphenyl; a substituted or unsubstituted divalent naphthyl; a substituted or unsubstituted divalent anthraceneyl; or a substituted or unsubstituted divalent phenanthryl.

7. The compound according to claim 2, wherein R3 is a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; or a substituted or unsubstituted pyrimidinyl.

8. The compound according to claim 2, wherein R4 is hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted methyl; substituted or unsubstituted ethyl; substituted or unsubstituted propyl; or substituted or unsubstituted pyrimidinyl.

9. The compound according to claim 1, wherein HAr2 is a triazine group, unsubstituted or substituted with two substituents selected independently of deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyrimidinyl; a pyrimidinyl group, unsubstituted or substituted with one to three substituents selected independently of deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted pyridinyl; or a triazine group, unsubstituted or substituted with two substituents selected independently of deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted pyrimidinyl. A quinazolinyl group substituted with one of the substituents of a substituted or unsubstituted naphthyl group; a benzothiophene-pyrimidinyl group substituted with one of the substituents selected from deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted pyridyl; or a benzofuran-pyrimidinyl group substituted with one of the substituents selected from deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted pyridyl.

10. The compound according to claim 1, wherein chemical formula 1 is any of the following structural formulas: ， ， ， ， ， ， 。 11. An organic light-emitting device, comprising: First electrode; Second electrode; as well as An organic material layer having one or more layers is disposed between the first electrode and the second electrode. One or more of the organic material layers contain a compound according to any one of claims 1 to 10.

12. The organic light-emitting device of claim 11, wherein the organic material layer comprises one or more layers of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and one or more of the layers contains the compound.

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