Compounds and organic light emitting devices comprising the same

Abstract

The present invention provides compounds and organic light emitting devices comprising the same.

Description

Technical Field

[0001] Cross-reference with related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2021-0153680 dated November 10, 2021 and Korean Patent Application No. 10-2022-0147816 dated November 8, 2022, the entire contents disclosed in those Korean patent applications being incorporated into this specification.

[0003] This invention relates to compounds and organic light-emitting devices containing the same. Background Technology

[0004] Organic light emission typically refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) utilizing organic light emission exhibit wide viewing angles, excellent contrast ratios, fast response times, and superior brightness, driving voltage, and response speed characteristics, thus attracting extensive research.

[0005] Organic light-emitting devices (OLEDs) typically have a structure comprising an anode and a cathode, and an organic layer located between the anode and cathode. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multilayer structure composed of different materials, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, they form excitons, which emit light when they re-enter the ground state.

[0006] For organic materials used in organic light-emitting devices as described above, there is a continuous need to develop new materials.

[0007] Existing technical documents

[0008] Patent documents

[0009] (Patent Document 1) Korean Patent Publication No. 10-2000-0051826 Summary of the Invention

[0010] Technical issues

[0011] This invention relates to organic light-emitting materials and organic light-emitting devices containing the same.

[0012] Solution to the problem

[0013] This invention provides compounds represented by the following chemical formula 1:

[0014] [Chemical Formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] X1 to X 10 Let any one of them be N, and the rest be CR.

[0018] Each of the above Rs is independently hydrogen, deuterium, or a substituent represented by the following chemical formula 2.

[0019] [Chemical Formula 2]

[0020]

[0021] In the above chemical formula 2,

[0022] Ar1 and Ar2 are each independently substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing one or more of N, O, and S. 2-60 Heteroaryl groups, but excluding biphenyls substituted with methoxy groups.

[0023] L1 to L3 are each an independent single bond; substituted or unsubstituted C 6-60 aryl; or substituted or unsubstituted C containing one or more of N, O and S. 2-60 Hybrid aryl.

[0024] In addition, the present invention provides an organic light-emitting device, comprising: a first electrode, a second electrode disposed opposite to the first electrode, and an organic layer of one or more disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by the above chemical formula 1.

[0025] Invention Effects

[0026] The compounds represented by the above-described chemical formula 1 can be used as materials for the organic layer of organic light-emitting devices, thereby achieving improved efficiency, lower driving voltage, and / or improved lifetime characteristics in organic light-emitting devices. In particular, the compounds represented by the above-described chemical formula 1 can be used as materials for hole injection, hole transport, light emission, electron transport, and / or electron injection. Attached Figure Description

[0027] Figure 1 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

[0028] Figure 2The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4. Detailed Implementation

[0029] The invention will now be described in more detail to aid in understanding.

[0030] The present invention provides compounds represented by the above chemical formula 1.

[0031] In this instruction manual, This indicates a bond that is linked to other substituents.

[0032] In this specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thio group. aryl thiols alkylsulfonyl arylsulfonyl Silyl; boronyl; alkyl; cycloalkyl; alkenyl; aryl; aralkyl; arylene; alkylaryl; alkylamino; aralkylamino; heteroarylamino; arylamino; arylphosphinyl; or a substituent consisting of one or more heteroaryl groups containing N, O, and S atoms, substituted or unsubstituted, or substituted or unsubstituted by a substituent formed by linking two or more substituents exemplified above. For example, "a substituent formed by linking two or more substituents" can be biphenyl. That is, biphenyl can be aryl, or it can be interpreted as a substituent formed by linking two phenyl groups.

[0033] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but it is preferred to have 1 to 40 carbon atoms. Specifically, it can be a substituent with the following structures, but is not limited thereto.

[0034]

[0035] In this specification, the oxygen in the ester group can be replaced by a straight-chain, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, it can be a substituent of the following structural formula, but is not limited thereto.

[0036]

[0037] In this specification, the number of carbon atoms in the imide group is not particularly limited, but it is preferred to have 1 to 25 carbon atoms. Specifically, it can be a substituent with the following structure, but is not limited thereto.

[0038]

[0039] In this specification, silanes specifically include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc., but are not limited to these.

[0040] In this specification, boron groups specifically include trimethylboronyl, triethylboronyl, tert-butyldimethylboronyl, triphenylboronyl, phenylboronyl, etc., but are not limited to these.

[0041] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine.

[0042] In this specification, the alkyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0043] In this specification, the alkenyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to yet another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, styryl, etc., but are not limited to these.

[0044] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group with 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., are used, but are not limited to these.

[0045] In this specification, the aryl group is not particularly limited, but is preferably an aryl group with 6 to 60 carbon atoms, and can be a monocyclic aryl or polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Regarding the aforementioned aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but is not limited to these. As the aforementioned polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, etc. It includes bases, fluorenes, etc., but is not limited to these.

[0046] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure. When the fluorene group is substituted as described above, it can be used to... etc., but not limited to this.

[0047] In this specification, a heteroaryl group is a heteroaryl group containing one or more of O, N, Si, and S as heteroelements. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to another embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of heteroaryl groups include thiophene, furanyl, pyrrole, imidazolyl, and thiazolyl. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, iso Azolyl, thiadiazolyl, phenthiazinyl, and dibenzofuranyl groups, but not limited to these.

[0048] In this specification, the aryl groups in aralkyl, aryl-alkenyl, alkylaryl, and arylamine are the same as those exemplified above. In this specification, the alkyl groups in aralkyl, alkylaryl, and alkylamine are the same as those exemplified above. In this specification, the heteroaryl groups in heteroarylamines are subject to the above description of heteroaryl groups. In this specification, the alkenyl groups in aryl-alkenyl are the same as those exemplified above. In this specification, arylene is a divalent group; otherwise, the above description of aryl groups applies. In this specification, heteroarylene is a divalent group; otherwise, the above description of heteroaryl groups applies. In this specification, the hydrocarbon ring is not a monovalent group but is formed by the combination of two substituents; otherwise, the above description of aryl or cycloalkyl groups applies. In this specification, heteroaryl is not a monovalent group but is formed by the combination of two substituents; otherwise, the above description of heteroaryl groups applies.

[0049] Preferably, the above chemical formula 1 can be represented by any one of the following chemical formulas 1-1 to 1-10:

[0050]

[0051] In the above chemical formulas 1-1 to 1-10,

[0052] R is defined in the same way as in chemical formula 1 above.

[0053] Preferably, in the above chemical formula 1, any one of R is a substituent represented by the above chemical formula 2, and the remainder can be hydrogen or deuterium. More preferably, any one of R is a substituent represented by the above chemical formula 2, and the remainder can be hydrogen.

[0054] Preferably, Ar1 and Ar2 can each be independently substituted or unsubstituted C. 6-30 aryl; or substituted or unsubstituted C containing one or more of N, O, and S. 2-30 The aryl group, but excluding biphenyl substituted with a methoxy group, is preferred. More preferably, Ar1 and Ar2 can each independently be phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, dibenzofuranyl, dibenzothiopheneyl, or phenylcarbazoyl, wherein Ar1 and Ar2 may be unsubstituted or substituted with one or more deuterium groups. Most preferably, Ar1 and Ar2 can each independently be any one selected from the group consisting of:

[0055]

[0056] Preferably, L1 to L3 can each be a single bond independently; substituted or unsubstituted C 6-20aryl; or substituted or unsubstituted C containing one or more of N, O and S. 2-20 Heteroaryl. More preferably, each of L1 to L3 can independently be a single bond, phenylene, naphthyl, dimethylfluorenediyl, diphenylfluorenediyl, or carbazolediyl. When L1 to L3 are phenylene, naphthyl, dimethylfluorenediyl, diphenylfluorenediyl, or carbazolediyl, L1 to L3 can be unsubstituted or substituted with one or more deuterium atoms. Most preferably, each of L1 to L3 can independently be a single bond, or selected from any of the following groups:

[0057]

[0058] Preferably, L1 can be a single bond, or an unsubstituted or deuterated phenylene.

[0059] Representative examples of compounds represented by the above chemical formula 1 are shown below:

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094] In the compound represented by the above chemical formula 1, X1 is N, X2 is a substituent represented by chemical formula 2, and X3 to X... 10 When CR and L1 are not single bonds, as an example, it can be manufactured as shown in reaction formula 1 below, where X1 is N, X2 is a substituent represented by chemical formula 2, and X3 to X... 10 When CR is a single bond and L1 is a single bond, as an example, it can be manufactured by the method shown in reaction formula 2 below. Other compounds can also be manufactured in a similar manner.

[0095] [Reaction Formula 1]

[0096]

[0097] [Reaction 2]

[0098]

[0099] In the above reaction formulas 1 and 2, R, L2, L3, Ar1 and Ar2 are defined as in the above chemical formula 1, and Z1 and Z2 are each independently halogens, preferably, Z1 and Z2 are each independently chlorine or bromine.

[0100] Reaction formula 1 described above is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base. The reactive group used in the Suzuki coupling reaction can be modified according to techniques known in the art. Furthermore, reaction formula 2 described above is an amine substitution reaction, preferably carried out in the presence of a palladium catalyst and a base. The reactive group used in the amine substitution reaction can be modified according to techniques known in the art. The above manufacturing method can be further specified in the manufacturing examples described later.

[0101] Furthermore, the present invention provides an organic light-emitting device comprising a compound represented by the above-described chemical formula 1. As an example, the present invention provides an organic light-emitting device comprising: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by the above-described chemical formula 1.

[0102] The organic layer of the organic light-emitting device of the present invention can be formed as a single layer or as a multilayer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of the present invention can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer as organic layers. However, the structure of the organic light-emitting device is not limited to this and may include fewer organic layers.

[0103] In addition, the aforementioned organic layer may include a light-emitting layer, which may contain a compound represented by the aforementioned chemical formula 1.

[0104] Furthermore, the aforementioned organic layer may include a hole transport layer, a hole injection layer, a layer that simultaneously performs hole transport and hole injection, or an electron blocking layer. The aforementioned hole transport layer, hole injection layer, layer that simultaneously performs hole transport and hole injection, or electron blocking layer may contain a compound represented by Chemical Formula 1. Preferably, the aforementioned hole transport layer, hole injection layer, or electron blocking layer may contain a compound represented by Chemical Formula 1. More preferably, the aforementioned electron blocking layer may contain a compound represented by Chemical Formula 1.

[0105] Furthermore, the organic light-emitting device according to the present invention can be a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. Additionally, the organic light-emitting device according to the present invention can be a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated below. Figure 1 and Figure 2 middle.

[0106] Figure 1 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. Figure 2 The illustration shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4. In the structure described above, the compound represented by Chemical Formula 1 may be included in the hole injection layer, the hole transport layer, the electron blocking layer, or the light-emitting layer. Preferably, the compound represented by Chemical Formula 1 may be included in the hole injection layer, the hole transport layer, or the electron blocking layer. More preferably, the compound represented by Chemical Formula 1 may be included in the electron blocking layer.

[0107] The organic light-emitting device according to the present invention, except that one or more of the organic layers contain a compound represented by the above-described chemical formula 1, can be manufactured using materials and methods known in the art. Furthermore, when the organic light-emitting device comprises a plurality of organic layers, the organic layers can be formed from the same substance or different substances.

[0108] For example, the organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be achieved by: depositing a metal or a conductive metal oxide or alloy thereof onto the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; then forming an organic layer comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the anode; and finally depositing a material suitable for use as a cathode onto the organic layer. Alternatively, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto the substrate.

[0109] Furthermore, the compound represented by the above chemical formula 1 can be used to form an organic layer in the manufacture of organic light-emitting devices not only by vacuum evaporation but also by solution coating. Here, solution coating refers to methods such as spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, and roller coating, but is not limited to these.

[0110] In addition to these methods, organic light-emitting devices can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003 / 012890). However, the manufacturing method is not limited to these methods.

[0111] As an example, the first electrode is the anode and the second electrode is the cathode, or the first electrode is the cathode and the second electrode is the anode.

[0112] As the aforementioned anode material, a material with a high work function is preferred in order to facilitate the injection of holes into the organic layer. Specific examples of the aforementioned anode materials include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0113] As the cathode material described above, a material with a low work function is generally preferred in order to facilitate the injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer structures such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0114] The aforementioned hole injection layer is a layer that injects holes from the electrode. Preferably, the hole injection material is a compound that possesses the ability to transport holes, the effect of injecting holes from the anode, excellent hole injection performance for the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material, and exhibits excellent thin film formation capability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between that of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile hexaazabenzophenanthrene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and conductive polymers based on polyaniline and polythiophene.

[0115] The aforementioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is a substance capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer; substances with high hole mobility are suitable. Specific examples include aryl amine-based organic compounds, conductive polymers, and block copolymers that simultaneously contain conjugated and non-conjugated portions, but are not limited to these.

[0116] The aforementioned electron blocking layer is a layer placed between the hole transport layer and the light-emitting layer to prevent electrons injected from the cathode from recombining in the light-emitting layer and transferring to the hole transport layer. It is also called an electron blocking layer. Preferably, the electron blocking layer is made of a material with lower electron affinity than the electron transport layer. More preferably, it may contain a compound represented by the above-described chemical formula 1 as the electron blocking layer.

[0117] The aforementioned luminescent material is capable of receiving holes and electrons from the hole transport layer and electron transport layer, respectively, and combining them to emit light in the visible light region. Preferably, it is a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complex (Alq3); carbazole compounds; diluted styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Compounds including azoles, benzothiazoles and benzimidazoles; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, fluorene, etc., but not limited to these.

[0118] The aforementioned luminescent layer may comprise a host material and a dopant material. The host material may be an aromatic fused-ring derivative or a heterocyclic compound. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but are not limited to these.

[0119] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are aromatic fused-ring derivatives with substituted or unsubstituted aryl amino groups, such as pyrene, anthracene, etc. Styrene compounds, such as diindene[3]pyrene, are compounds in which at least one aryl vinyl group is substituted onto a substituted or unsubstituted aryl amine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, styrene, styrene diamine, styrene triamine, styrene tetraamine, etc., are examples, but are not limited thereto. Furthermore, as metal complexes, iridium complexes, platinum complexes, etc., are examples, but are not limited thereto. As an example, any one or more of the following groups can be used as dopant materials, but are not limited thereto:

[0120]

[0121]

[0122] The aforementioned hole-blocking layer is a layer placed between the electron transport layer and the light-emitting layer to prevent holes injected from the anode from recombining in the light-emitting layer and transferring to the electron transport layer. It is also called a hole suppression layer. The hole-blocking layer is preferably made of a material with a high ionization energy.

[0123] The aforementioned electron transport layer is the layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is one that can effectively receive electrons from the cathode and transfer them to the light-emitting layer; materials with high electron mobility are suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are common materials with low work functions and accompanied by an aluminum or silver layer. Specifically, these are cesium, barium, calcium, ytterbium, and samarium, each accompanied by an aluminum or silver layer.

[0124] The aforementioned electron injection layer is a layer that injects electrons from the electrode. Preferably, compounds are those that possess electron transport capabilities, effectively inject electrons from the cathode, exhibit excellent electron injection performance for the light-emitting layer or material, prevent excitons generated in the light-emitting layer from migrating to the hole injection layer, and demonstrate excellent thin-film formation ability. Specifically, these include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0125] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium, but are not limited to these.

[0126] On the other hand, in this invention, the "hole injection and transport layer" is a layer that simultaneously performs the functions of the hole injection layer and the hole transport layer. It can be a substance that performs the functions of each of the above layers, either alone or in combination, but is not limited to this.

[0127] The organic light-emitting device according to the present invention can be a bottom-emission device, a top-emission device, or a bidirectional light-emitting device, and in particular, it can be a bottom-emission device that requires relatively high luminous efficiency.

[0128] In addition, the compound represented by the above chemical formula 1 can be included not only in organic light-emitting devices, but also in organic solar cells or organic transistors.

[0129] The manufacture of compounds represented by the above chemical formula 1 and organic light-emitting devices containing them is specifically described in the following synthesis examples and embodiments. However, the following examples are for illustrative purposes only and the scope of the invention is not limited thereto.

[0130] Manufacturing Example 1

[0131]

[0132] 5-Bromo-2-chloropyridin-4-amine (15 g, 72.3 mmol) and (2-methoxynaphthalen-1-yl)boronic acid (15.3 g, 75.9 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (30 g, 216.9 mmol) was dissolved in 100 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14 g of compound A-1-1_P1. (Yield 68%, MS: [M+H)) + =285)

[0133] Compound A-1-1_P1 (15 g, 52.7 mmol) and HBF4 (9.3 g, 105.4 mmol) were added to 150 mL of acetonitrile and stirred. Then, NaNO2 (14.6 g, 105.4 mmol) was dissolved in 30 mL of water and slowly added at 0 °C. After reacting for 8 hours, the mixture was heated to room temperature and diluted with 300 mL of water. The solution was dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.9 g of compound A-1-1. (Yield 52%, MS: [M+H]) + =254)

[0134] Manufacturing Example 2

[0135]

[0136] 4-bromopyridin-3-amine (15 g, 86.7 mmol) and (4-chloro-2-methoxynaphthalen-1-yl)boronic acid (21.5 g, 91 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (35.9 g, 260.1 mmol) was dissolved in 100 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.9 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.5 g of compound A-2-4_P1. (Yield 67%, MS: [M+H]) + =285)

[0137] Compound A-2-4_P1 (15 g, 52.7 mmol) and HBF4 (9.3 g, 105.4 mmol) were added to 150 mL of acetonitrile and stirred. Then, NaNO2 (14.6 g, 105.4 mmol) was dissolved in 30 mL of water and slowly added at 0 °C. After reacting for 10 hours, the mixture was heated to room temperature and diluted with 300 mL of water. The solution was dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.7 g of compound A-2-4. (Yield 50%, MS: [M+H]) + =254)

[0138] Manufacturing Example 3

[0139]

[0140] 3-bromopyridin-2-amine (15 g, 86.7 mmol) and (5-chloro-2-methoxynaphthalen-1-yl)boronic acid (21.5 g, 91 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (35.9 g, 260.1 mmol) was dissolved in 100 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.9 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.7 g of compound A-3-5_P1. (Yield 72%, MS: [M+H]) + =285)

[0141] Compound A-3-5_P1 (15 g, 52.7 mmol) and HBF4 (9.3 g, 105.4 mmol) were added to 150 mL of acetonitrile and stirred. Then, NaNO2 (14.6 g, 105.4 mmol) was dissolved in 30 mL of water and slowly added at 0 °C. After reacting for 9 hours, the mixture was heated to room temperature and diluted with 300 mL of water. The solution was dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 7.1 g of compound A-3-5. (Yield 53%, MS: [M+H]) + =254)

[0142] Manufacturing Example 4

[0143]

[0144] 2-Bromopyridin-3-amine (15 g, 86.7 mmol) and (5-chloro-2-methoxynaphthyl-1-yl)boronic acid (21.5 g, 91 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (35.9 g, 260.1 mmol) was dissolved in 100 mL of water and added, stirred thoroughly, followed by bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.9 mmol). After reacting for 4 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.2 g of compound A-4-6_P1. (Yield 70%, MS: [M+H]) + =285)

[0145] Compound A-4-6_P1 (15 g, 52.7 mmol) and HBF4 (9.3 g, 105.4 mmol) were added to 150 mL of acetonitrile and stirred. Then, NaNO2 (14.6 g, 105.4 mmol) was dissolved in 30 mL of water and slowly added at 0 °C. After reacting for 10 hours, the mixture was heated to room temperature and diluted with 300 mL of water. The solution was dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.7 g of compound A-4-6. (Yield 73%, MS: [M+H]) + =254)

[0146] Manufacturing Example 5

[0147]

[0148] 2-Bromo-6-chloroaniline (15 g, 72.6 mmol) and (3-methoxyisoquinolin-4-yl)boronicacid (15.5 g, 76.3 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (30.1 g, 217.9 mmol) was dissolved in 100 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.8 g of compound A-5-3_P1. (Yield 67%, MS: [M+H]) + =285)

[0149] Compound A-5-3_P1 (15 g, 52.7 mmol) and HBF4 (9.3 g, 105.4 mmol) were added to 150 mL of acetonitrile and stirred. Then, NaNO2 (14.6 g, 105.4 mmol) was dissolved in 30 mL of water and slowly added at 0 °C. After reacting for 10 hours, the mixture was heated to room temperature and diluted with 300 mL of water. The solution was dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 8.3 g of compound A-5-3. (Yield 62%, MS: [M+H]) + =254)

[0150] Manufacturing Example 6

[0151]

[0152] 2-Bromoaniline (15 g, 87.2 mmol) and (7-chloro-3-methoxyquinolin-4-yl)boronic acid (21.7 g, 91.5 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (36.2 g, 261.6 mmol) was dissolved in 100 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.9 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.6 g of compound A-6-6_P1. (Yield 75%, MS: [M+H]) + =285)

[0153] Compound A-6-6_P1 (15 g, 52.7 mmol) and HBF4 (9.3 g, 105.4 mmol) were added to 150 mL of acetonitrile and stirred. Then, NaNO2 (14.6 g, 105.4 mmol) was dissolved in 30 mL of water and slowly added at 0 °C. After reacting for 8 hours, the mixture was heated to room temperature and diluted with 300 mL of water. The solution was dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 7.7 g of compound A-6-6. (Yield 58%, MS: [M+H]) + =254)

[0154] Manufacturing Example 7

[0155]

[0156] 2-Bromoaniline (15 g, 87.2 mmol) and (7-chloro-6-methoxyquinolin-5-yl)boronic acid (21.7 g, 91.5 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (36.2 g, 261.6 mmol) was dissolved in 100 mL of water and added, stirred thoroughly, followed by bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.9 mmol). After reacting for 5 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.1 g of compound A-7-4_P1. (Yield 73%, MS: [M+H]) + =285)

[0157] Compound A-7-4_P1 (15 g, 52.7 mmol) and HBF4 (9.3 g, 105.4 mmol) were added to 150 mL of acetonitrile and stirred. Then, NaNO2 (14.6 g, 105.4 mmol) was dissolved in 30 mL of water and slowly added at 0 °C. After reacting for 10 hours, the mixture was heated to room temperature and diluted with 300 mL of water. The solution was dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 7.9 g of compound A-7-4. (Yield 59%, MS: [M+H]) + =254)

[0158] Manufacturing Example 8

[0159]

[0160] 2-Bromoaniline (15 g, 87.2 mmol) and (3-chloro-6-methoxyisoquinolin-5-yl)boronic acid (21.7 g, 91.5 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (36.2 g, 261.6 mmol) was dissolved in 100 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.9 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.3 g of compound A-8-7_P1. (Yield 74%, MS: [M+H]) + =285)

[0161] Compound A-8-7_P1 (15 g, 52.7 mmol) and HBF4 (9.3 g, 105.4 mmol) were added to 150 mL of acetonitrile and stirred. Then, NaNO2 (14.6 g, 105.4 mmol) was dissolved in 30 mL of water and slowly added at 0 °C. After reacting for 8 hours, the mixture was heated to room temperature and diluted with 300 mL of water. The solution was dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.7 g of compound A-8-7. (Yield 50%, MS: [M+H]) + =254)

[0162] Manufacturing Example 9

[0163]

[0164] 2-Bromo-4-chloroaniline (15 g, 72.6 mmol) and (7-methoxyisoquinolin-8-yl)boronic acid (15.5 g, 76.3 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (30.1 g, 217.9 mmol) was dissolved in 100 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.2 g of compound A-9-1_P1. (Yield 69%, MS: [M+H]) + =285)

[0165] Compound A-9-1_P1 (15 g, 52.7 mmol) and HBF4 (9.3 g, 105.4 mmol) were added to 150 mL of acetonitrile and stirred. Then, NaNO2 (14.6 g, 105.4 mmol) was dissolved in 30 mL of water and slowly added at 0 °C. After reacting for 10 hours, the mixture was heated to room temperature and diluted with 300 mL of water. The solution was dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.9 g of compound A-9-1. (Yield 74%, MS: [M+H]) + =254)

[0166] Manufacturing Example 10

[0167]

[0168] 2-Bromoaniline (15 g, 87.2 mmol) and (5-chloro-7-methoxyquinolin-8-yl)boronic acid (21.7 g, 91.5 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (36.2 g, 261.6 mmol) was dissolved in 100 mL of water and added, stirred thoroughly, followed by bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.9 mmol). After reacting for 4 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.1 g of compound A-10-5_P1. (Yield 73%, MS: [M+H]) + =285)

[0169] Compound A-10-5_P1 (15 g, 52.7 mmol) and HBF4 (9.3 g, 105.4 mmol) were added to 150 mL of acetonitrile and stirred. Then, NaNO2 (14.6 g, 105.4 mmol) was dissolved in 30 mL of water and slowly added at 0 °C. After reacting for 8 hours, the mixture was heated to room temperature and diluted with 300 mL of water. The solution was dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 8.4 g of compound A-10-5. (Yield 63%, MS: [M+H]) + =254)

[0170] Precursor substances other than the precursor compounds synthesized in Manufacturing Examples 1 to 10 described above were obtained through different intermediates and by the method described above. The obtained precursor substances were used to manufacture the compounds of the synthesis examples described later.

[0171] Synthesis example 1

[0172]

[0173] Compound A-4-8 (15 g, 59.1 mmol) and compound amine 1 (32.5 g, 62.1 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (24.5 g, 177.3 mmol) was dissolved in 100 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25.8 g of compound 1. (Yield 71%, MS: [M+H)) + =615)

[0174] Synthesis example 2

[0175]

[0176] Under a nitrogen atmosphere, compound A-4-3 (15 g, 59.1 mmol), compound amine 2 (18.3 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 20.6 g of compound 2. (Yield 68%, MS: [M+H)) + =513)

[0177] Synthesis example 3

[0178]

[0179] Under a nitrogen atmosphere, compound A-4-1 (15 g, 59.1 mmol), compound amine 3 (22.4 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 23.6 g of compound 3. (Yield 69%, MS: [M+H)) + =579)

[0180] Synthesis example 4

[0181]

[0182] Under a nitrogen atmosphere, compound A-1-3 (15 g, 59.1 mmol), compound amine 4 (22.4 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 20.9 g of compound 4. (Yield 61%, MS: [M+H)) + =579)

[0183] Synthesis example 5

[0184]

[0185] Under a nitrogen atmosphere, compound A-1-1 (15 g, 59.1 mmol), compound amine 5 (20 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 21 g of compound 5. (Yield 66%, MS: [M+H)) + =539)

[0186] Synthesis example 6

[0187]

[0188] Under a nitrogen atmosphere, compound A-1-5 (15 g, 59.1 mmol), compound amine 6 (23.7 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 24.8 g of compound 6. (Yield 70%, MS: [M+H)) + =599)

[0189] Synthesis Example 7

[0190]

[0191] Under a nitrogen atmosphere, compound A-2-7 (15 g, 59.1 mmol), compound amine 7 (21.7 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 24.8 g of compound 7. (Yield 74%, MS: [M+H)) + =567)

[0192] Synthesis example 8

[0193]

[0194] Under a nitrogen atmosphere, compound A-2-7 (15 g, 59.1 mmol), compound amine 8 (25.5 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 26.7 g of compound 8. (Yield 72%, MS: [M+H)) + =628)

[0195] Synthesis example 9

[0196]

[0197] Compound A-2-5 (15 g, 59.1 mmol) and compound amine 9 (30.9 g, 62.1 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (24.5 g, 177.3 mmol) was dissolved in 100 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.1 g of compound 9. (Yield 75%, MS: [M+H)) + =589)

[0198] Synthesis example 10

[0199]

[0200] Under a nitrogen atmosphere, compound A-2-2 (15 g, 59.1 mmol), compound amine 10 (23.1 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 21.9 g of compound 10. (Yield 63%, MS: [M+H)) +=589)

[0201] Synthesis example 11

[0202]

[0203] Under a nitrogen atmosphere, compound A-2-1 (15 g, 59.1 mmol), compound amine 11 (24.7 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 26.1 g of compound 11. (Yield 72%, MS: [M+H)) + =615)

[0204] Synthesis example 12

[0205]

[0206] Under a nitrogen atmosphere, compound A-3-7 (15 g, 59.1 mmol), compound amine 12 (20.8 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 24.5 g of compound 12. (Yield 75%, MS: [M+H)) + =553)

[0207] Synthesis example 13

[0208]

[0209] Under a nitrogen atmosphere, compound A-3-8 (15 g, 59.1 mmol), compound amine 13 (24.7 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 22.5 g of compound 13. (Yield 62%, MS: [M+H)) + =615)

[0210] Synthesis example 14

[0211]

[0212] Under a nitrogen atmosphere, compound A-5-2 (15 g, 59.1 mmol), compound amine 14 (25.5 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 22.7 g of compound 14. (Yield 61%, MS: [M+H)) + =629)

[0213] Synthesis Example 15

[0214]

[0215] Compound A-5-7 (15 g, 59.1 mmol) and compound amine 15 (34.4 g, 62.1 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (24.5 g, 177.3 mmol) was dissolved in 100 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24 g of compound 15. (Yield 63%, MS: [M+H)) +=645)

[0216] Synthesis example 16

[0217]

[0218] Under a nitrogen atmosphere, compound A-6-2 (15 g, 59.1 mmol), compound amine 16 (30.1 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 29.1 g of compound 16. (Yield 70%, MS: [M+H)) + =703)

[0219] Synthesis Example 17

[0220]

[0221] Under a nitrogen atmosphere, compound A-6-7 (15 g, 59.1 mmol), compound amine 17 (24.7 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 22.9 g of compound 17. (Yield 63%, MS: [M+H)) + =615)

[0222] Synthesis Example 18

[0223]

[0224] Compound A-7-2 (15 g, 59.1 mmol) and compound amine 18 (30.9 g, 62.1 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (24.5 g, 177.3 mmol) was dissolved in 100 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.6 g of compound 18. (Yield 62%, MS: [M+H)) + =589)

[0225] Synthesis example 19

[0226]

[0227] Under a nitrogen atmosphere, compound A-7-4 (15 g, 59.1 mmol), compound amine 19 (22.7 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 23.1 g of compound 19. (Yield 67%, MS: [M+H)) + =583)

[0228] Synthesis example 20

[0229]

[0230] Under a nitrogen atmosphere, compound A-7-1 (15 g, 59.1 mmol), compound amine 20 (23.1 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 24.7 g of compound 20. (Yield 71%, MS: [M+H))+ =589)

[0231] Synthesis Example 21

[0232]

[0233] Under a nitrogen atmosphere, compound A-8-1 (15 g, 59.1 mmol), compound amine 21 (26.2 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 28.3 g of compound 21. (Yield 75%, MS: [M+H)) + =639)

[0234] Synthesis example 22

[0235]

[0236] Under a nitrogen atmosphere, compound A-8-5 (15 g, 59.1 mmol), compound amine 22 (30.1 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 31.1 g of compound 22. (Yield 75%, MS: [M+H)) + =703)

[0237] Synthesis example 23

[0238]

[0239] Compound A-9-1 (15 g, 59.1 mmol) and compound amine 23 (29.6 g, 62.1 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (24.5 g, 177.3 mmol) was dissolved in 100 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.1 g of compound 23. (Yield 73%, MS: [M+H)) + =559)

[0240] Synthesis example 24

[0241]

[0242] Under a nitrogen atmosphere, compound A-9-5 (15 g, 59.1 mmol), compound amine 24 (30 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 28.2 g of compound 24. (Yield 68%, MS: [M+H)) + =701)

[0243] Synthesis example 25

[0244]

[0245] Compound A-9-4 (15 g, 59.1 mmol) and compound amine 25 (27.8 g, 62.1 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (24.5 g, 177.3 mmol) was dissolved in 100 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.9 g of compound 25. (Yield 75%, MS: [M+H]) + =539)

[0246] Synthesis Example 26

[0247]

[0248] Under a nitrogen atmosphere, compound A-10-2 (15 g, 59.1 mmol), compound amine 26 (20 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 20.4 g of compound 26. (Yield 64%, MS: [M+H)) + =539)

[0249] Synthesis Example 27

[0250]

[0251] Under a nitrogen atmosphere, compound A-10-7 (15 g, 59.1 mmol), compound amine 27 (21.4 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 23.9 g of compound 27. (Yield 72%, MS: [M+H))+ =563)

[0252] Synthesis example 28

[0253]

[0254] Under a nitrogen atmosphere, compound A-10-8 (15 g, 59.1 mmol), compound amine 28 (26.5 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 24 g of compound 28. (Yield 63%, MS: [M+H)) + =645)

[0255] Synthesis Example 29

[0256]

[0257] Under a nitrogen atmosphere, compound A-10-5 (15 g, 59.1 mmol), compound amine 29 (25.5 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 24.1 g of compound 29. (Yield 65%, MS: [M+H)) + =628)

[0258] Example 1

[0259] ITO (indium tin oxide) is used as A glass substrate coated with a thin film of ITO was immersed in distilled water containing detergent and washed using ultrasound. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for 10 minutes of ultrasonic washing. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0260] On the prepared ITO transparent electrode, as a hole injection layer, the following compound HI-1 is applied... The thickness is formed by p-doping compound A-1 at a concentration of 1.5% by weight. Compound HT-1 is then vacuum-deposited onto the hole-implanted layer to form a film thickness. The hole transport layer. Next, on the aforementioned hole transport layer, at a film thickness of... The compound 1 manufactured above was vacuum-deposited to form an electron blocking layer. Next, on the compound 1, compound RH-1 as the host and compound Dp-7 as the dopant were vacuum-deposited at a weight ratio of 98:2 to form... A red luminescent layer of a certain thickness. On the aforementioned luminescent layer, a film thickness of... A hole-blocking layer was formed by vacuum evaporation of the following compound HB-1. Next, the following compound ET-1 and the following compound LiQ were vacuum evaporated onto the hole-blocking layer in a 2:1 weight ratio, thereby achieving... The thickness forms an electron injection and transport layer. On this electron injection and transport layer, lithium fluoride (LiF) is sequentially applied... The thickness, using aluminum The cathode is formed by vapor deposition of a certain thickness.

[0261]

[0262] During the above process, the evaporation rate of organic matter is maintained. Lithium fluoride maintenance of the cathode The evaporation rate of aluminum maintains The evaporation rate is such that the vacuum level is maintained at 2*10 during evaporation. -7 ~5*10 -6 This led to the creation of organic light-emitting devices.

[0263] Examples 2 to 29

[0264] In the organic light-emitting device of Example 1, compound 1 was replaced by the compound listed in Table 1 below. Otherwise, the organic light-emitting device was manufactured by the same method as in Example 1 above.

[0265] Comparative Examples 1 to 6

[0266] In the organic light-emitting device of Example 1, compound 1 was replaced by the compound listed in Table 1 below. Otherwise, the organic light-emitting device was manufactured by the same method as in Example 1 above. The structures of compounds C-1 to C-6 in Table 1 are shown below.

[0267]

[0268] Experimental Example

[0269] When a current was applied to the organic light-emitting devices manufactured in Examples 1 to 29 and Comparative Examples 1 to 6, the current (15 mA / cm²) was measured. 2 Voltage and efficiency are shown in Table 1 below. Lifetime T95 refers to the time required for the brightness to decrease from the initial brightness (6000 nits) to 95%.

[0270] [Table 1]

[0271]

[0272]

[0273] When an electric current was applied to the organic light-emitting devices prepared according to Examples 1 to 29 and Comparative Examples 1 to 6, the results shown in Table 1 were obtained. As the material constituting the red organic light-emitting device of Example 1, in addition to compound 1, conventionally widely used materials were used, and compound Dp-7 was used as a dopant for the red light-emitting layer.

[0274] Comparative Examples 1 to 6 used C-1 to C-6 instead of Compound 1 to fabricate organic light-emitting devices. As shown in Table 1 above, when the compounds of the present invention are used as electron blocking layers, the driving voltage is lower and the efficiency is higher compared to the comparative example materials, indicating that energy transfer from the host to the red dopant is well formed. Furthermore, it can be seen that while maintaining high efficiency, lifetime characteristics are also significantly improved. This can be attributed to the higher stability of the compounds of the present invention for electrons and holes compared to the comparative example compounds.

[0275] In summary, it can be confirmed that using the compounds of the present invention as electron blocking layers in red light-emitting layers can improve the driving voltage, luminous efficiency, and lifetime characteristics of organic light-emitting devices.

[0276] [Symbol Explanation]

[0277] 1: Substrate 2: Anode

[0278] 3: Light-emitting layer 4: Cathode

[0279] 5: Hole injection layer; 6: Hole transport layer

[0280] 7: Electron blocking layer; 8: Hole blocking layer

[0281] 9: Electron injection and transport layer.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, X1 to X 10 Let any one of them be N, and the rest be CR. Any one of R is a substituent represented by the chemical formula 2, and the rest are hydrogen or deuterium. [Chemical Formula 2] In the chemical formula 2, Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, diphenylfluorenyl, spirodifluorenyl, dibenzofuranyl, dibenzothiopheneyl, or phenylcarbazoyl. Ar1 and Ar2 were either not substituted or were substituted by more than one deuterium. L1 is a single bond, or an unsubstituted or deuterated phenylene, L2 and L3 are each independently a single bond, a phenylene group, or a naphthyl group, and When L2 and L3 are phenylene or naphthyl, L2 and L3 are either unsubstituted or substituted with one or more deuterium atoms.

2. The compound according to claim 1, wherein, Ar1 and Ar2 are each independently selected from any of the following groups: 。 3. The compound according to claim 1, wherein, L1 to L3 are each independently a single bond or a phenylene group. When L1 to L3 are phenylene, L1 to L3 are either unsubstituted or substituted with one or more deuterium atoms.

4. The compound according to claim 1, wherein, L1 is a single bond or can be selected from any of the following groups: L2 to L3 are each independently a single bond or selected from any of the following groups: 。 5. The compound according to claim 1, wherein, L1 is a single bond.

6. A compound that is selected from any one of the following groups: 。 7. An organic light-emitting device, wherein, include: A first electrode, a second electrode disposed opposite to the first electrode, and an organic layer of one or more layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to claim 1.

8. The organic light-emitting device according to claim 7, wherein, The organic layer is a hole injection layer, a hole transport layer, or an electron blocking layer.

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