Novel compound and organic light-emitting device using same

Abstract

The invention provides a novel compound and an organic light-emitting device using the same.

Description

Technical Field

[0001] This invention relates to novel compounds and organic light-emitting devices containing the same. Background Technology

[0002] Cross-reference with related applications

[0003] This application claims priority based on Korean Patent Application No. 10-2023-0101021, dated August 2, 2023, the entire contents of which are disclosed in the document and are incorporated herein by reference.

[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 0001) Korean Patent Publication No. 10-2000-0051826 Summary of the Invention

[0010] Technical issues

[0011] This invention relates to novel compounds 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] R can be either hydrogen or deuterium independently.

[0018] One of R1 and R2 is a substituent of chemical formula 2 below, and the other is hydrogen or deuterium.

[0019] [Chemical Formula 2]

[0020]

[0021] In the above chemical formula 2,

[0022] L1 and L2 are each independently a single bond, or an unsubstituted or deuterated phenylene.

[0023] Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted tetraphenyl, or any one of the following substituents:

[0024]

[0025] The compound represented by the above chemical formula 1 is either not substituted with deuterium or is substituted with more than one deuterium.

[0026] 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.

[0027] Invention Effects

[0028] 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, hole injection and transport, light emission, electron transport, or electron injection. Attached Figure Description

[0029] 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.

[0030] Figure 2 The 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, a light-emitting layer 7, an electron transport layer 8, and a cathode 4. Detailed Implementation

[0031] The invention will now be described in more detail to aid in understanding.

[0032] In this instruction manual, or This indicates a bond that is linked to other substituents.

[0033] 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 thio ( ), alkylsulfonyl ( ); arylsulfonyl ( ); silyl; boronyl; alkyl; cycloalkyl; alkenyl; aryl; aralkyl; arylene; alkylaryl; alkylamine; aralkylamine; heteroarylamine; arylamine; arylphosphinyl; or a substituent formed by connecting two or more of the above-exemplified substituents, either substituted or unsubstituted, containing one or more of the N, O, and S atoms. For example, "a substituent formed by connecting two or more substituents" can be biphenyl. That is, biphenyl can be aryl, or it can be interpreted as a substituent formed by connecting two phenyl groups.

[0034] 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 compound with the structure shown below, but is not limited thereto.

[0035]

[0036] In this specification, the ester group can be a straight-chain, branched, or cyclic alkyl group with 1 to 25 carbon atoms, or an aryl group with 6 to 25 carbon atoms, in which the oxygen atom is replaced. Specifically, it can be a compound with the following structural formula, but is not limited thereto.

[0037]

[0038] 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 compound with the structure shown below, but is not limited thereto.

[0039]

[0040] In this specification, silanes specifically include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, 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-methylbutyl, 1-ethylbutyl, 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-dimethylpropyl, isohexyl, 2-methylpentyl, 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 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, stilbyl, 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. As a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. As a polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, peryl, thionyl, fluoreneyl, etc., but is not limited thereto.

[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, it can be... Etc. But it is not limited to this.

[0047] In this specification, a heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as heteroelements. The number of carbon atoms is not particularly limited, but preferably 2 to 60. Examples of heterocyclic groups include thiophene, furanyl, pyrrole, imidazole, 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 heterocyclic 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 heterocyclic 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, the heterocyclic group is not a monovalent group but is formed by the combination of two substituents; otherwise, the above description of heterocyclic groups applies.

[0049] In the above chemical formula 1, one or more hydrogen atoms can be substituted by deuterium, that is, the compound represented by the above chemical formula 1 is either not substituted by deuterium or is substituted by one or more deuterium atoms.

[0050] Preferably, L1 and L2 are each independently a single bond or any one of the following groups:

[0051]

[0052] In the above groups, n is an integer from 0 to 4.

[0053] Preferably, Ar1 and Ar2 are each independently a substituent of phenyl, biphenyl, triphenyl, tetraphenyl, or any of the following groups:

[0054]

[0055] The aforementioned Ar1 and Ar2 are each independently unreplaced or not replaced by one or more deuterium or one or more C. 1-5 Alkyl substitution.

[0056] Preferably, Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, or tetraphenyl.

[0057] The Ar1 and Ar2 mentioned above are each independently unsubstituted; or substituted by one or more deuterium or one or two methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl groups.

[0058] Preferably, at least one of Ar1 and Ar2 is biphenyl.

[0059] Representative examples of compounds represented by the above chemical formula 1 are shown below. In the following compounds, "Dn" indicates the number of deuterium substitutions. For example, D1 indicates one deuterium substitution, n is 1 or more, and the number of hydrogen atoms in each compound is as follows:

[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]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108] Preferably, in the above "Dn", n is 1 or more, 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, 9 or more, or 10 or more and 40 or less, 39 or less, 38 or less, 37 or less, 36 or less, 35 or less, 34 or less, 33 or less, 32 or less, 31 or less, 30 or less, 29 or less, 28 or less, 27 or less, 26 or less, or 25 or less.

[0109] Furthermore, as an example of the present invention, in the above-described chemical formula 1, when R1 is a substituent of the above-described chemical formula 2, a method for manufacturing the compound represented by the above-described chemical formula 1 is provided as shown in the following reaction formula 1. Additionally, in the above-described chemical formula 1, when R2 is a substituent of the above-described chemical formula 2, it can be manufactured with reference to the following reaction formula 1.

[0110] [Reaction Formula 1]

[0111]

[0112] In reaction formula 1 above, all except X are the same as defined above, where X is a halogen, preferably chlorine or bromine. The above reaction 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.

[0113] 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.

[0114] 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 hole transport auxiliary 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.

[0115] Furthermore, the aforementioned organic layer may include a light-emitting layer comprising a compound represented by the aforementioned chemical formula 1. In particular, the compound according to the invention can be used as a dopant in the light-emitting layer.

[0116] In addition, the aforementioned organic layer may include an electron transport layer or an electron injection layer, which contains a compound represented by the aforementioned chemical formula 1.

[0117] In addition, the aforementioned electron transport layer, electron injection layer, or layer that simultaneously performs electron transport and electron injection contains a compound represented by the aforementioned chemical formula 1.

[0118] In addition, the aforementioned organic layer includes a light-emitting layer and an electron transport layer, wherein the electron transport layer may contain a compound represented by the aforementioned chemical formula 1.

[0119] 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 2 middle.

[0120] 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. In the structure described above, the compound represented by the above chemical formula 1 may be included in the light-emitting layer.

[0121] Figure 2 The 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, a light-emitting layer 7, an electron transport layer 8, and a cathode 4. In the structure described above, the compound represented by the above-described chemical formula 1 may be included in one or more of the hole injection layer, hole transport layer, light-emitting layer, and electron transport layer.

[0122] 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.

[0123] 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.

[0124] 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.

[0125] 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.

[0126] 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.

[0127] 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.

[0128] 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.

[0129] 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.

[0130] 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.

[0131] 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.

[0132] 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, pentane derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds. ), pyrimidine derivatives, etc., but not limited to these.

[0133] As dopant materials, there are aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are aromatic fused-ring derivatives having substituted or unsubstituted aryl amino groups, such as pyrene, anthracene, benzo[a]pyrene, etc., having aryl amino groups. Styrene amine compounds are compounds in which at least one aryl vinyl group is substituted on 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, there are styrene amines, styrene diamines, styrene triamines, styrene tetraamines, etc., but they are not limited to these. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but they are not limited to these.

[0134] 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.

[0135] 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.

[0136] 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.

[0137] Depending on the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0138] 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.

[0139] Preferred embodiments are presented below to aid in understanding the present invention. However, these embodiments are provided merely to facilitate a better understanding of the invention, and the scope of the invention is not limited thereto.

[0140] [Example]

[0141] Example 1: Preparation of Compound 1

[0142]

[0143] Under a nitrogen atmosphere, compound 1 (sub1) (10 g, 34.6 mmol), compound amine 1 (amine1) (11.7 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound 1 (12.9 g, 65% yield).

[0144] MS:[M+H] + =575

[0145] Example 2: Preparation of Compound 2

[0146]

[0147] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 2 (17.2 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 2 (16.8 g, 67% yield).

[0148] MS:[M+H] + =727

[0149] Example 3: Preparation of Compound 3

[0150]

[0151] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 3 (14.5 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 3 (16.7 g, 74% yield).

[0152] MS:[M+H] + =651

[0153] Example 4: Preparation of Compound 4

[0154]

[0155] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 4 (19.8 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 4 (18 g, 65% yield).

[0156] MS:[M+H] + =799

[0157] Example 5: Preparation of Compound 5

[0158]

[0159] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 5 (13.9 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 5 (11 g, 50% yield).

[0160] MS:[M+H] + =637

[0161] Example 6: Preparation of Compound 6

[0162]

[0163] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 6 (12.1 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 6 (11.4 g, 56% yield).

[0164] MS:[M+H] + =587

[0165] Example 7: Preparation of Compound 7

[0166]

[0167] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 7 (16.6 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 7 (15.7 g, 64% yield).

[0168] MS:[M+H] + =709

[0169] Example 8: Preparation of Compound 8

[0170]

[0171] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 8 (12.6 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 8 (13.5 g, 65% yield).

[0172] MS:[M+H] + =599

[0173] Example 9: Preparation of Compound 9

[0174]

[0175] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 9 (14.2 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 9 (13.3 g, 60% yield).

[0176] MS:[M+H] + =643

[0177] Example 10: Preparation of Compound 10

[0178]

[0179] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 10 (18.3 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 10 (15.2 g, 58% yield).

[0180] MS:[M+H] + =757

[0181] Example 11: Preparation of Compound 11

[0182]

[0183] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 11 (18.3 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 11 (13.9 g, 53% yield).

[0184] MS:[M+H] + =757

[0185] Example 12: Preparation of Compound 12

[0186]

[0187] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 12 (18.5 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 12 (18.5 g, 70% yield).

[0188] MS:[M+H] + =763

[0189] Example 13: Preparation of Compound 13

[0190]

[0191] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 13 (16.5 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 13 (15.9 g, 65% yield).

[0192] MS:[M+H] + =707

[0193] Example 14: Preparation of Compound 14

[0194]

[0195] Under a nitrogen atmosphere, compound 2 (10 g, 34.6 mmol), compound amine 14 (14.5 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 14 (17.3 g, 77% yield).

[0196] MS:[M+H] + =651

[0197] Example 15: Preparation of Compound 15

[0198]

[0199] Under a nitrogen atmosphere, compound 2 (10 g, 34.6 mmol), compound amine 15 (14.5 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 15 (15.8 g, 70% yield).

[0200] MS:[M+H] + =651

[0201] Example 16: Preparation of Compound 16

[0202]

[0203] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 16 (17.2 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 16_P1 (19.9 g, 79% yield).

[0204] MS:[M+H] + =727

[0205] Compound 16_P1 (10 g, 13.8 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In another container, deuterium oxide (9.9 g, 495.9 mmol) was added to trifluoromethanesulfonic anhydride (23.3 g, 82.7 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was then distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 16 (D18, 6.5 g, yield 63%).

[0206] MS:[M+H] + =745

[0207] Example 17: Preparation of Compound 17

[0208]

[0209] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 17 (14.5 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 17_P1 (14.9 g, 66% yield).

[0210] MS:[M+H] + =651

[0211] Compound 17_P1 (10 g, 15.4 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In a separate container, deuterium oxide (11.1 g, 554 mmol) was added to trifluoromethanesulfonic anhydride (26 g, 92.3 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 17 (D22, 6.3 g, 61% yield).

[0212] MS:[M+H] + =673

[0213] Example 18: Preparation of Compound 18

[0214]

[0215] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 18 (12.3 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 18_P1 (15.1 g, 74% yield).

[0216] MS:[M+H] + =591

[0217] Compound 18_P1 (10 g, 17 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In another container, deuterium oxide (12.2 g, 610.3 mmol) was added to trifluoromethanesulfonic anhydride (28.7 g, 101.7 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 18 (D15, 7.3 g, 71% yield).

[0218] MS:[M+H] + =606

[0219] Example 19: Preparation of Compound 19

[0220]

[0221] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 19 (15.6 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 19_P1 (17.9 g, 76% yield).

[0222] MS:[M+H] + =683

[0223] Compound 19_P1 (10 g, 14.7 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In a separate container, deuterium oxide (10.6 g, 527.9 mmol) was added to trifluoromethanesulfonic anhydride (24.8 g, 88 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 19 (D15, 6.1 g, 60% yield).

[0224] MS:[M+H] + =698

[0225] Example 20: Preparation of Compound 20

[0226]

[0227] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 20 (15.8 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 20_P1 (18.1 g, 76% yield).

[0228] MS:[M+H] + =687

[0229] Compound 20_P1 (10 g, 14.6 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In another container, deuterium oxide (10.5 g, 524.8 mmol) was added to trifluoromethanesulfonic anhydride (24.7 g, 87.5 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 20 (D19, 6.9 g, 67% yield).

[0230] MS:[M+H] + =706

[0231] Example 21: Preparation of Compound 21

[0232]

[0233] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 21 (15.6 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 21_P1 (17.5 g, 74% yield).

[0234] MS:[M+H] + =683

[0235] Compound 21_P1 (10 g, 14.7 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In a separate container, deuterium oxide (10.6 g, 527.9 mmol) was added to trifluoromethanesulfonic anhydride (24.8 g, 88 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 21 (D17, 6.3 g, 61% yield).

[0236] MS:[M+H] + =700

[0237] Example 22: Preparation of Compound 22

[0238]

[0239] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 22 (11.9 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 22_P1 (12 g, 60% yield).

[0240] MS:[M+H] + =581

[0241] Compound 22_P1 (10 g, 17.2 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In another container, deuterium oxide (12.4 g, 620.9 mmol) was added to trifluoromethanesulfonic anhydride (29.2 g, 103.5 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 22 (D18, 7.4 g, 72% yield).

[0242] MS:[M+H] + =599

[0243] Example 23: Preparation of Compound 23

[0244]

[0245] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 23 (15.5 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 23_P1 (17.7 g, 75% yield).

[0246] MS:[M+H] + =681

[0247] Compound 23_P1 (10 g, 14.7 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In another container, deuterium oxide (10.6 g, 529.5 mmol) was added to trifluoromethanesulfonic anhydride (24.9 g, 88.2 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 23 (D25, 7.6 g, 73% yield).

[0248] MS:[M+H] + =706

[0249] Example 24: Preparation of Compound 24

[0250]

[0251] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 24 (19.5 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 24_P1 (16.9 g, 62% yield).

[0252] MS:[M+H] + =789

[0253] Compound 24_P1 (10 g, 12.7 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In another container, deuterium oxide (9.1 g, 456.8 mmol) was added to trifluoromethanesulfonic anhydride (21.5 g, 76.1 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 24 (D22, 7.3 g, 71% yield).

[0254] MS:[M+H] + =811

[0255] Example 25: Preparation of Compound 25

[0256]

[0257] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 25 (16.5 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 25_P1 (16.4 g, 67% yield).

[0258] MS:[M+H] + =707

[0259] Compound 25_P1 (10 g, 14.2 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In another container, deuterium oxide (10.2 g, 510 mmol) was added to trifluoromethanesulfonic anhydride (24 g, 85 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 25 (D20, 7.4 g, 72% yield).

[0260] MS:[M+H] + =727

[0261] Example 26: Preparation of Compound 26

[0262]

[0263] Under a nitrogen atmosphere, compound 2 (10 g, 34.6 mmol), compound amine 26 (14.5 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 26_P1 (14.9 g, 66% yield).

[0264] MS:[M+H] + =651

[0265] Compound 26_P1 (10 g, 15.4 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In a separate container, deuterium oxide (11.1 g, 554 mmol) was added to trifluoromethanesulfonic anhydride (26 g, 92.3 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 26 (D18, 6.7 g, 65% yield).

[0266] MS:[M+H] + =669

[0267] Example 27: Preparation of Compound 27

[0268]

[0269] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 27 (14.5 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 27_P1 (11.9 g, 53% yield).

[0270] MS:[M+H] + =651)

[0271] Compound 27_P1 (10 g, 15.4 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In another container, deuterium oxide (12.3 g, 615.5 mmol) was added to trifluoromethanesulfonic anhydride (43.4 g, 153.9 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 10 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 27 (D31, 6.3 g, 60% yield).

[0272] MS:[M+H] + =682

[0273] Example 28: Preparation of Compound 28

[0274]

[0275] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 28 (15.1 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 28_P1 (16.9 g, 73% yield).

[0276] MS:[M+H] + =669

[0277] Compound 28_P1 (10 g, 15 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In another container, deuterium oxide (12 g, 598.9 mmol) was added to trifluoromethanesulfonic anhydride (42.2 g, 149.7 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 10 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 28 (D28, 6.6 g, 63% yield).

[0278] MS:[M+H] + =697

[0279] Example 29: Preparation of Compound 29

[0280]

[0281] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 29 (18.3 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 29_P1 (15.7 g, 60% yield).

[0282] MS:[M+H] + =757

[0283] Compound 29_P1 (10 g, 13.2 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In another container, deuterium oxide (10.6 g, 529.1 mmol) was added to trifluoromethanesulfonic anhydride (37.3 g, 132.3 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 10 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 29 (D34, 6.7 g, 64% yield).

[0284] MS:[M+H] + =791

[0285] Example 30: Preparation of Compound 30

[0286]

[0287] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 30 (20.4 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 30_P1 (20.6 g, 73% yield).

[0288] MS:[M+H] + =815

[0289] Compound 30_P1 (10 g, 12.3 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In another container, deuterium oxide (9.8 g, 491.3 mmol) was added to trifluoromethanesulfonic anhydride (34.7 g, 122.8 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 10 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 30 (D30, 6.5 g, 63% yield).

[0290] MS:[M+H] + =845

[0291] Example 31: Preparation of Compound 31

[0292]

[0293] Under a nitrogen atmosphere, compound 1 (10 g, 34.6 mmol), compound amine 31 (13.7 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 31_P1 (15.5 g, 71% yield).

[0294] MS:[M+H] + =631

[0295] Compound 31_P1 (10 g, 15.9 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In another container, deuterium oxide (12.7 g, 635.1 mmol) was added to trifluoromethanesulfonic anhydride (44.8 g, 158.8 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 10 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 31 (D28, 7.3 g, 70% yield).

[0296] MS:[M+H] + =659

[0297] Example 32: Preparation of Compound 32

[0298]

[0299] Under a nitrogen atmosphere, compound 2 (10 g, 34.6 mmol), compound amine 32 (14.5 g, 36.4 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 32_P1 (17.8 g, 79% yield).

[0300] MS:[M+H] + =651

[0301] Compound 32_P1 (10 g, 15.4 mmol) was added to 1,2,4-trichlorobenzene (200 ml) and stirred at room temperature. In another container, deuterium oxide (12.3 g, 615.5 mmol) was added to trifluoromethanesulfonic anhydride (43.4 g, 153.9 mmol) at 0 °C and stirred for 10 hours to prepare a solution. Then, a mixture of trifluoromethanesulfonic anhydride and deuterium oxide was added dropwise to the prepared 1,2,4-trichlorobenzene solution, and the mixture was heated to 140 °C and maintained with stirring. After reacting for 10 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give compound 32 (D32, 7.4 g, 71% yield).

[0302] MS:[M+H] + =683

[0303] [Experimental Example]

[0304] Experimental Example 1

[0305] A glass substrate coated with an ITO (indium tin oxide) film at a thickness of 1000 Å was immersed in distilled water containing detergent and ultrasonically washed. 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 ultrasonic washing was repeated twice with distilled water for 10 minutes each time. 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.

[0306] On the prepared ITO transparent electrode, as a hole injection layer, the following HI-1 compound is formed to a thickness of 1100 Å, and the following A-1 compound is p-doped at a concentration of 1.5%. On the hole injection layer, the following HT-1 compound is vacuum-deposited to form a hole transport layer with a thickness of 800 Å. On the hole transport layer, the aforementioned compound 1 is thermally vacuum-deposited to a thickness of 100 Å to form a hole transport auxiliary layer. On the hole transport auxiliary layer, the following BH-1 and BD-1 compounds are vacuum-deposited at a weight ratio of 25:1 to a thickness of 250 Å to form a light-emitting layer. On the light-emitting layer, the following HB-1 compound is vacuum-deposited to a thickness of 50 Å to form a hole blocking layer. On the hole blocking layer, the following ET-1 and LiQ compounds are thermally vacuum-deposited at a weight ratio of 1:1 to a thickness of 310 Å to form an electron transport and electron injection layer. On the aforementioned electron transport and electron injection layers, lithium fluoride (LiF) with a thickness of 12 Å and aluminum with a thickness of 1000 Å are sequentially vapor-deposited to form a cathode, thereby fabricating an organic light-emitting device.

[0307]

[0308] During the above process, the evaporation rate of organic materials was maintained at 0.4~0.7 Å / s, the evaporation rate of lithium fluoride at the cathode was maintained at 0.3 Å / s, and the evaporation rate of aluminum was maintained at 2 Å / s. During evaporation, the vacuum level was maintained at 2 x 0. -7 ~5x10 -6 This led to the creation of organic light-emitting devices.

[0309] Experimental Examples 2 to 32

[0310] Organic light-emitting devices were fabricated using the compounds listed in Table 1 below instead of compound 1, except that organic light-emitting devices were fabricated using the same method as in Experimental Example 1 above.

[0311] Comparative Experiment Examples 1 to 6

[0312] Organic light-emitting devices were fabricated using the compounds listed in Table 1 below instead of compound 1, except that the methods described in Experimental Example 1 above were also used. The compounds C-1 to C-6 listed in Table 1 below are shown below.

[0313]

[0314] An application of 15 mA / cm² was applied to the organic light-emitting devices fabricated in the above experimental and comparative experimental examples. 2 When the current was applied, the voltage and efficiency were measured, and the results are shown in Table 1 below. Lifetime LT95 refers to the time required for the brightness to decrease from the initial brightness (1000 nits) to 95%.

[0315] [Table 1]

[0316]

[0317]

[0318] As shown in the experimental examples in Table 1 above, the compounds of the present invention are used as hole transport auxiliary layers in the blue light-emitting layer. When compared with the compounds in the comparative experimental examples, it was confirmed that the organic light-emitting devices using the compounds of the present invention exhibited improved driving voltage, efficiency, and lifetime. Furthermore, it was confirmed that the lifetime characteristics of the deuterium-substituted compounds were further improved. It was determined that the compounds of the present invention contribute to the stability of excitons formed within the light-emitting layer, thereby demonstrating an effect of improving the characteristics of the organic light-emitting device.

[0319] [Symbol Explanation]

[0320] 1: Substrate 2: Anode

[0321] 3: Light-emitting layer 4: Cathode

[0322] 5: Hole injection layer; 6: Hole transport layer

[0323] 7: Light-emitting layer; 8: Electron transport layer.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, R can be either hydrogen or deuterium independently. One of R1 and R2 is a substituent of chemical formula 2 below, and the other is hydrogen or deuterium. [Chemical Formula 2] In the chemical formula 2, L1 and L2 are each independently a single bond, or an unsubstituted or deuterated phenylene. Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted tetraphenyl, or any one of the following substituents: The compound represented by the chemical formula 1 is either not substituted with deuterium or is substituted with more than one deuterium.

2. The compound according to claim 1, wherein, L1 and L2 are each independently a single bond, or any of the following groups: In the group, n is an integer from 0 to 4.

3. The compound according to claim 1, wherein, Ar1 and Ar2 are each independently a substituent of phenyl, biphenyl, triphenyl, tetraphenyl, or any of the following groups. Ar1 and Ar2 are each independently unsubstituted or replaced by one or more deuterium or one or more C. 1-5 Alkyl substitution.

4. The compound according to claim 1, wherein, Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, or tetraphenyl. Ar1 and Ar2 are each independently unsubstituted; or substituted by one or more deuterium groups or by one or two methyl, ethyl, propyl, isopropyl, butyl, isobutyl, or tert-butyl groups.

5. The compound according to claim 1, wherein, The compound represented by the chemical formula 1 is selected from any one of the following compounds: In the compound, "Dn" represents the number of deuterium substitutions.

6. 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 any one of claims 1 to 5.

7. The organic light-emitting device according to claim 6, wherein, The organic layer containing the compound is a light-emitting layer, a hole transport auxiliary layer, or a hole transport layer.

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