Novel compounds and organic light-emitting devices comprising the same

Abstract

This invention provides novel compounds and organic light-emitting devices utilizing the same.

Description

Technical Field

[0001] Cross-reference with related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2022-0046807, dated April 15, 2022, the entire contents of which are disclosed in the document and are incorporated herein by reference.

[0003] This invention relates to novel 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, an exciton is formed. When this exciton re-enters the ground state, it emits light.

[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 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 or 2:

[0014] [Chemical Formula 1]

[0015]

[0016] [Chemical Formula 2]

[0017]

[0018] In the above chemical formulas 1 and 2,

[0019] X is O or S.

[0020] R represents C with or without substitution. 6-60 aryl, where one of R1 to R8 is a substituent represented by the following chemical formula 3, and the remainder is hydrogen or deuterium; or

[0021] R is a substituent represented by chemical formula 3, where R1 to R8 are each independently hydrogen or deuterium.

[0022] [Chemical Formula 3]

[0023]

[0024] In the above chemical formula 3,

[0025] L represents a single bond; C is either substituted or unsubstituted. 6-60 aryl; or substituted or unsubstituted C containing one or more of N, O and S. 2-60 Hybrid aryl,

[0026] L1 and L2 are each independent single bonds; 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,

[0027] 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 Mixed aromatics,

[0028] When R is a substituent represented by the above chemical formula 3, the following structures are excluded from the substituents represented by the above chemical formula 3:

[0029]

[0030] 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 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 chemical formula 1 or 2.

[0031] Invention Effects

[0032] The compounds represented by the above-mentioned chemical formula 1 or 2 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-mentioned chemical formula 1 or 2 can be used as materials for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection. Attached Figure Description

[0033] 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.

[0034] 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

[0035] The invention will now be described in more detail to aid in understanding.

[0036] In this instruction manual, Or it can represent a bond that is linked to other substituents.

[0037] 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 heterocyclic group containing one or more of the N, O, and S atoms, substituted or unsubstituted, or substituted or unsubstituted by two or more of the substituents exemplified above. For example, "a substituent formed by two or more substituents" can be biphenyl. That is, biphenyl can be aryl, or it can be interpreted as a substituent formed by two phenyl groups linked together.

[0038] 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 group with the following structure, but is not limited thereto.

[0039]

[0040] In this specification, the oxygen atom in the ester group may 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 may be a group with the following structural formula, but is not limited thereto.

[0041]

[0042] 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 group with the following structure, but is not limited thereto.

[0043]

[0044] In this specification, silanes specifically include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc., but are not limited to these.

[0045] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine.

[0046] 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, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] 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 become... Etc. But it is not limited to this.

[0051] 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 is 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.

[0052] 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 heterocycle is not a monovalent group but is formed by the combination of two substituents; otherwise, the above description of heterocyclic groups applies.

[0053] In chemical formula 1 or 2 above, one or more hydrogen atoms can be replaced by deuterium.

[0054] Preferably, R is phenyl, biphenyl or naphthyl, one of R1 to R8 is a substituent represented by the above chemical formula 3, and the rest are hydrogen or deuterium.

[0055] Preferably, when R is a substituent represented by the above chemical formula 3, L is a single bond, phenylene, biphenyldiyl, or naphthylene, L1 and L2 are each independently a single bond, phenylene, biphenyldiyl, or naphthylene, and Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, (phenyl)naphthyl, (naphthyl)phenyl, phenanthrene, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothiopheneyl, carbazole-9-yl, or 9-phenyl-carbazoleyl, wherein Ar1 and Ar2 are not both phenyl and not both biphenyl-4-yl.

[0056] Preferably, L is a single bond, phenylene, biphenyl dimethyl or naphthylene.

[0057] Preferably, L1 and L2 are each independently a single bond, a phenylene group, a biphenyl dimethyl group, or a naphthylene group.

[0058] Preferably, Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, (phenyl)naphthyl, (naphthyl)phenyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothiopheneyl, carbazole-9-yl or 9-phenyl-carbazoleyl.

[0059] Preferably, Ar1 and Ar2 are different from each other.

[0060] Representative examples of compounds represented by chemical formula 1 or 2 are shown below:

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081] On the other hand, as an example, the present invention provides methods for manufacturing compounds represented by the above-described chemical formula 1, as shown in reaction formulas 1 and 2 below, respectively. Reaction formula 1 below indicates the case where R is a substituent represented by the above-described chemical formula 3, and reaction formula 2 below indicates the case where one of R1 to R8 is a substituent represented by the above-described chemical formula 3. Compounds represented by the above-described chemical formula 2 can also be manufactured with reference to the following reaction formulas:

[0082] [Reaction Formula 1]

[0083]

[0084] [Reaction 2]

[0085]

[0086] In reaction formulas 1 and 2 above, the definitions of all elements except X1 are the same as those described above, where X1 is a halogen, more preferably chlorine or bromine. The above reaction, as a Suzuki coupling reaction or an amine substitution reaction, is preferably carried out in the presence of a palladium catalyst and a base. The reactive group used in such a 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.

[0087] Furthermore, the present invention provides an organic light-emitting device comprising a compound represented by the above-described chemical formula 1 or 2. 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 or 2.

[0088] 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.

[0089] Furthermore, the aforementioned organic layer may include a light-emitting layer comprising a compound represented by chemical formula 1 or 2. In particular, the compound according to the invention may be used as the host of the light-emitting layer.

[0090] 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 or 2.

[0091] 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 or 2.

[0092] 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 or 2.

[0093] 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 .

[0094] 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, a compound represented by chemical formula 1 or 2 may be included in the light-emitting layer.

[0095] 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, a compound represented by the above chemical formula 1 or 2 may be included in one or more of the above-described hole injection layer, hole transport layer, light-emitting layer, and electron transport layer.

[0096] The organic light-emitting device according to the present invention, except that one or more of the organic layers contain compounds represented by the above-described chemical formula 1 or 2, 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.

[0097] 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.

[0098] Furthermore, compounds represented by the aforementioned chemical formula 1 or 2 can be used to form organic layers 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.

[0099] 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.

[0100] 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.

[0101] 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.

[0102] 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.

[0103] 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.

[0104] 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.

[0105] 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 of the azole, benzothiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV) polymers; spirocyclic compounds; polyfluorene, fluorene, etc., but not limited to these.

[0106] 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.

[0107] 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. Diindrone pyrene, etc., styrylamine compounds are compounds in which at least one aryl vinyl group is substituted onto a substituted or unsubstituted arylamine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamines, styryldiamines, styryltriamines, styryltetraamines, etc., but they are not limited to these. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but they are not limited to these.

[0108] 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.

[0109] 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 light-emitting material, prevent excitons generated in the light-emitting layer from migrating to the hole injection layer, and possess excellent thin-film forming 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.

[0110] 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.

[0111] 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.

[0112] In addition, compounds represented by the above chemical formula 1 or 2 can be included not only in organic light-emitting devices, but also in organic solar cells or organic transistors.

[0113] Preferred embodiments are presented below to aid in understanding the invention. However, these embodiments are provided merely for the purpose of facilitating a clearer understanding of the invention, and the invention is not intended to be limited thereto.

[0114] [Example]

[0115] Example 1

[0116]

[0117] Under a nitrogen atmosphere, compound sub1 (15 g, 40.1 mmol), amine 1 (13.5 g, 42.1 mmol), and sodium tert-butoxide (5.8 g, 60.1 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 13.3 g of compound 1. (Yield 54%, MS: [M+H)) + =615)

[0118] Example 2

[0119]

[0120] Under a nitrogen atmosphere, compound 1 (15 g, 40.1 mmol), compound amine 2 (14.1 g, 42.1 mmol), and sodium tert-butoxide (5.8 g, 60.1 mmol) were added to xylene (300 mL), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. The reaction was stopped after 5 hours, 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 13.1 g of compound 2. (Yield 52%, MS: [M+H)) + =629)

[0121] Example 3

[0122]

[0123] Under a nitrogen atmosphere, compound 1 (15 g, 40.1 mmol), compound amine 3 (14.1 g, 42.1 mmol), and sodium tert-butoxide (5.8 g, 60.1 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 13.8 g of compound 3. (Yield 55%, MS: [M+H)) + =629)

[0124] Example 4

[0125]

[0126] Under a nitrogen atmosphere, compound 1 (15 g, 40.1 mmol), compound amine 4 (17.3 g, 42.1 mmol), and sodium tert-butoxide (5.8 g, 60.1 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 19.7 g of compound 4. (Yield 70%, MS: [M+H)) + =704)

[0127] Example 5

[0128]

[0129] Compound 1 (15 g, 40.1 mmol) and compound amine 5 (19.2 g, 42.1 mmol) were added to THF (300 ml), stirred, and refluxed. Then, potassium carbonate (16.6 g, 120.2 mmol) was dissolved in water (100 ml) and added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 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 22.3 g of compound 5. (Yield 79%, MS: [M+H)) + =705)

[0130] Example 6

[0131]

[0132] Compound 1 (15 g, 40.1 mmol) and compound amine 6 (18.6 g, 42.1 mmol) were added to THF (300 ml), stirred, and refluxed. Then, potassium carbonate (16.6 g, 120.2 mmol) was dissolved in water (100 ml) and added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 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 21.6 g of compound 6. (Yield 78%, MS: [M+H)) + =691)

[0133] Example 7

[0134]

[0135] Under a nitrogen atmosphere, compound 2 (15 g, 40.1 mmol), compound amine 7 (14.7 g, 42.1 mmol), and sodium tert-butoxide (5.8 g, 60.1 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 15.7 g of compound 7. (Yield 61%, MS: [M+H)) + =643)

[0136] Example 8

[0137]

[0138] Compound 3 (15 g, 33.3 mmol) and compound amine 8 (18.1 g, 35 mmol) were added to THF (300 ml), stirred, and refluxed. Then, potassium carbonate (13.8 g, 99.9 mmol) was dissolved in water (100 ml) and added, stirred thoroughly, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol). 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 17.4 g of compound 8. (Yield 62%, MS: [M+H)) + =843)

[0139] Example 9

[0140]

[0141] Compound 4 (15 g, 40.1 mmol) and amine 9 (19.8 g, 42.1 mmol) were added to THF (300 ml) and stirred under reflux. Then, potassium carbonate (16.6 g, 120.2 mmol) was dissolved in water (100 ml) and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 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 22.8 g of compound 9. (Yield 79%, MS: [M+H])+ =721)

[0142] Example 10

[0143]

[0144] Under a nitrogen atmosphere, compound 4 (15 g, 40.1 mmol), compound amine 10 (14.5 g, 42.1 mmol), and sodium tert-butoxide (5.8 g, 60.1 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 15.1 g of compound 10. (Yield 59%, MS: [M+H)) + =639)

[0145] Example 11

[0146]

[0147] Under a nitrogen atmosphere, compound 5 (15 g, 40.1 mmol), compound amine 11 (15.2 g, 42.1 mmol), and sodium tert-butoxide (5.8 g, 60.1 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 16.5 g of compound 11. (Yield 63%, MS: [M+H)) + =655)

[0148] Example 12

[0149]

[0150] Under a nitrogen atmosphere, compound 6 (15 g, 59.1 mmol), compound amine 12 (21.7 g, 62.1 mmol), and sodium tert-butoxide (8.5 g, 88.7 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was stopped, 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 21.4 g of compound 12. (Yield 64%, MS: [M+H)) + =567)

[0151] Example 13

[0152]

[0153] Compound 6 (15 g, 59.1 mmol) and compound amine 13 (28.2 g, 62.1 mmol) were added to THF (300 ml), stirred, and refluxed. Then, potassium carbonate (24.5 g, 177.4 mmol) was dissolved in water (100 ml) and added. 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 23.4 g of compound 13. (Yield 63%, MS: [M+H)) + =628)

[0154] Example 14

[0155]

[0156] Compound 6 (15 g, 59.1 mmol) and compound amine 14 (32.9 g, 62.1 mmol) were added to THF (300 ml), stirred, and refluxed. Then, potassium carbonate (24.5 g, 177.4 mmol) was dissolved in water (100 ml) and added. 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 30.8 g of compound 14. (Yield 74%, MS: [M+H)) + =704)

[0157] Example 15

[0158]

[0159] Under a nitrogen atmosphere, compound 6 (15 g, 59.1 mmol), compound amine 15 (25.5 g, 62.1 mmol), and sodium tert-butoxide (8.5 g, 88.7 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was stopped, 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 21.5 g of compound 15. (Yield 58%, MS: [M+H)) + =628)

[0160] Example 16

[0161]

[0162] Under a nitrogen atmosphere, compound 7 (15 g, 40.1 mmol), compound amine 16 (17.7 g, 42.1 mmol), and sodium tert-butoxide (5.8 g, 60.1 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 17.7 g of compound 16. (Yield 62%, MS: [M+H)) +=715)

[0163] Example 17

[0164]

[0165] Under a nitrogen atmosphere, compound 7 (15 g, 40.1 mmol), compound amine 17 (14.1 g, 42.1 mmol), and sodium tert-butoxide (5.8 g, 60.1 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 17.1 g of compound 17. (Yield 63%, MS: [M+H)) + =679)

[0166] Example 18

[0167]

[0168] Under a nitrogen atmosphere, compound 8 (15 g, 40.1 mmol), compound amine 18 (17.3 g, 42.1 mmol), and sodium tert-butoxide (5.8 g, 60.1 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 16.6 g of compound 18. (Yield 55%, MS: [M+H)) + =754)

[0169] Example 19

[0170]

[0171] Compound 9 (15 g, 40.1 mmol) and amine 19 (20.3 g, 42.1 mmol) were added to THF (300 ml) and stirred under reflux. Then, potassium carbonate (16.6 g, 120.2 mmol) was dissolved in water (100 ml) and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 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 18.4 g of compound 19. (Yield 63%, MS: [M+H)) + =731)

[0172] Example 20

[0173]

[0174] Under a nitrogen atmosphere, compound 9 (15 g, 40.1 mmol), compound amine 20 (17.3 g, 42.1 mmol), and sodium tert-butoxide (5.8 g, 60.1 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 16.3 g of compound 20. (Yield 58%, MS: [M+H)) + =704)

[0175] Example 21

[0176]

[0177] Under a nitrogen atmosphere, compound 10 (15 g, 40.1 mmol), compound amine 21 (14.1 g, 42.1 mmol), and sodium tert-butoxide (5.8 g, 60.1 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 16.6 g of compound 21. (Yield 66%, MS: [M+H)) +=629)

[0178] Example 22

[0179]

[0180] Under a nitrogen atmosphere, compound 10 (15 g, 40.1 mmol), compound amine 22 (15.2 g, 42.1 mmol), and sodium tert-butoxide (5.8 g, 60.1 mmol) were added to xylene (300 mL), stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 15.2 g of compound 22. (Yield 52%, MS: [M+H)) + =731)

[0181] Example 23

[0182]

[0183] Compound 11 (15 g, 59.1 mmol) and amine 23 (28.9 g, 62.1 mmol) were added to THF (300 ml), stirred, and refluxed. Then, potassium carbonate (24.5 g, 177.4 mmol) was dissolved in water (100 ml) and added. 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 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 27.2 g of compound 23. (Yield 72%, MS: [M+H]) + =639)

[0184] Example 24

[0185]

[0186] Compound 12 (15 g, 40.1 mmol) and amine 24 (22.3 g, 42.1 mmol) were added to THF (300 ml) and stirred under reflux. Then, potassium carbonate (16.6 g, 120.2 mmol) was dissolved in water (100 ml) and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 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 21.2 g of compound 24. (Yield 68%, MS: [M+H)) + =780)

[0187] Example 25

[0188]

[0189] Compound 13 (15 g, 40.1 mmol) and amine 25 (20.3 g, 42.1 mmol) were added to THF (300 ml), stirred, and refluxed. Then, potassium carbonate (16.6 g, 120.2 mmol) was dissolved in water (100 ml) and added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 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 19.6 g of compound 25. (Yield 67%, MS: [M+H)) + =731)

[0190] Example 26

[0191]

[0192] Under a nitrogen atmosphere, compound 14 (15 g, 38.4 mmol), amine 26 (17.1 g, 40.4 mmol), and sodium tert-butoxide (5.5 g, 57.6 mmol) were added to xylene (300 mL) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. The reaction was stopped after 5 hours, 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 18.9 g of compound 26. (Yield 67%, MS: [M+H)) + =734)

[0193] Example 27

[0194]

[0195] Under a nitrogen atmosphere, compound 14 (15 g, 38.4 mmol), compound amine 27 (14.7 g, 40.4 mmol), and sodium tert-butoxide (5.5 g, 57.6 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 17.9 g of compound 27. (Yield 69%, MS: [M+H)) + =675)

[0196] Example 28

[0197]

[0198] Compound 14 (15 g, 38.4 mmol) and amine 28 (20.9 g, 40.4 mmol) were added to THF (300 ml), stirred, and refluxed. Then, potassium carbonate (15.9 g, 115.3 mmol) was dissolved in water (100 ml) and added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 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 21 g of compound 28. (Yield 70%, MS: [M+H)) +=783)

[0199] Example 29

[0200]

[0201] Under a nitrogen atmosphere, compound 14 (15 g, 38.4 mmol), compound amine 29 (14.7 g, 40.4 mmol), and sodium tert-butoxide (5.5 g, 57.6 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. The reaction was stopped after 5 hours, 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 15.3 g of compound 29. (Yield 55%, MS: [M+H)) + =725)

[0202] Example 30

[0203]

[0204] Compound 15 (15 g, 38.4 mmol) and compound amine 30 (19 g, 40.4 mmol) were added to THF (300 ml), stirred, and refluxed. Then, potassium carbonate (15.9 g, 115.3 mmol) was dissolved in water (100 ml) and added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 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 19.2 g of compound 30. (Yield 68%, MS: [M+H)) + =737)

[0205] Example 31

[0206]

[0207] Under a nitrogen atmosphere, compound 16 (15 g, 55.6 mmol), amine 31 (15.1 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. The reaction was stopped after 5 hours, 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 17.5 g of compound 31. (Yield 64%, MS: [M+H)) + =493)

[0208] Example 32

[0209]

[0210] Under a nitrogen atmosphere, compound 16 (15 g, 55.6 mmol), compound amine 32 (21.1 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was stopped, 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 21.1 g of compound 32. (Yield 64%, MS: [M+H)) + =595)

[0211] Example 33

[0212]

[0213] Under a nitrogen atmosphere, compound 16 (15 g, 55.6 mmol), compound amine 33 (20.5 g, 58.4 mmol), and sodium tert-butoxide (8 g, 83.4 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was stopped, 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 20.1 g of compound 33. (Yield 62%, MS: [M+H)) + =585)

[0214] Example 34

[0215]

[0216] Compound 16 (15 g, 55.6 mmol) and amine 34 (31 g, 58.4 mmol) were added to THF (300 ml) and stirred under reflux. Then, potassium carbonate (23.1 g, 166.8 mmol) was dissolved in water (100 ml) 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 32 g of compound 34. (Yield 80%, MS: [M+H)) + =720)

[0217] Example 35

[0218]

[0219] Under a nitrogen atmosphere, compound 17 (15 g, 38.4 mmol), compound amine 35 (11.9 g, 40.4 mmol), and sodium tert-butoxide (5.5 g, 57.6 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 15.6 g of compound 35. (Yield 67%, MS: [M+H)) + =605)

[0220] Example 36

[0221]

[0222] Under a nitrogen atmosphere, compound 18 (15 g, 38.4 mmol), compound amine 36 (18.6 g, 40.4 mmol), and sodium tert-butoxide (5.5 g, 57.6 mmol) were added to xylene (300 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 18.6 g of compound 36. (Yield 63%, MS: [M+H)) + =770)

[0223] Example 37

[0224]

[0225] Under a nitrogen atmosphere, compound 19 (15 g, 38.4 mmol), compound amine 37 (16.6 g, 40.4 mmol), and sodium tert-butoxide (5.5 g, 57.6 mmol) were added to xylene (300 mL) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. The reaction was stopped after 5 hours, 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 16.9 g of compound 37. (Yield 61%, MS: [M+H)) + =720)

[0226] Example 38

[0227]

[0228] Compound 20 (15 g, 32.2 mmol) and amine 38 (17.9 g, 33.8 mmol) were added to THF (300 ml) and stirred under reflux. Then, potassium carbonate (13.3 g, 96.5 mmol) was dissolved in water (100 ml) and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 19.6 g of compound 38. (Yield 70%, MS: [M+H)) +=872)

[0229] Example 39

[0230]

[0231] Compound 21 (15 g, 38.4 mmol) and amine 39 (21.4 g, 40.4 mmol) were added to THF (300 ml) and stirred under reflux. Then, potassium carbonate (15.9 g, 115.3 mmol) was dissolved in water (100 ml) and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 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 23.8 g of compound 39. (Yield 78%, MS: [M+H]) + =796)

[0232] Example 40

[0233]

[0234] Under a nitrogen atmosphere, compound 22 (15 g, 38.4 mmol), compound amine 40 (16.6 g, 40.4 mmol), and sodium tert-butoxide (5.5 g, 57.6 mmol) were added to xylene (300 mL) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 5 hours, the reaction was stopped, 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 15.8 g of compound 40. (Yield 57%, MS: [M+H)) + =720)

[0235] [Experimental Example]

[0236] Experimental Example 1

[0237] 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.

[0238] On the prepared ITO transparent electrode, as a hole injection layer, the following HI-1 compound is applied... The thickness is formed by p-doping the following A-1 compound at a concentration of 1.5%. The following HT-1 compound is then vacuum-deposited onto the hole-implanted layer to form a film thickness. A hole transport layer. On the aforementioned hole transport layer, the following EB-1 compound is vacuum-deposited to form a film with a thickness of [insert thickness here]. An electron blocking layer was then formed. Next, on the electron blocking layer, the compound 1 manufactured above and the Dp-39 compound described below were vacuum-deposited at a weight ratio of 98:2 to form a film with a thickness of [missing information]. The light-emitting layer is formed by vacuum evaporation of the HB-1 compound onto the aforementioned light-emitting layer, thereby creating a film with a thickness of [insert thickness here]. A hole-blocking layer is formed. Next, the ET-1 compound and the LiQ compound are vacuum-deposited onto the hole-blocking layer at a weight ratio of 2:1 to form a film with a thickness of [insert thickness here]. An electron injection and transport layer. On the aforementioned electron injection and transport layer, lithium fluoride (LiF) is sequentially... The thickness, using aluminum The cathode is formed by vapor deposition of a certain thickness, thereby manufacturing organic light-emitting devices.

[0239]

[0240] 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 x 10 during evaporation. -7 ~5x10 -6 This led to the creation of organic light-emitting devices.

[0241] Experimental Examples 2 to 40

[0242] Organic light-emitting devices were manufactured using the compounds listed in Table 1 below instead of compound 1, except that the method was the same as that used in Experimental Example 1 above.

[0243] Comparative Experiment Examples 1 to 8

[0244] Organic light-emitting devices were fabricated using the compounds listed in Table 2 below instead of compound 1, except that the method was the same as in Experimental Example 1 described above. The compounds listed in Table 2 below are shown below.

[0245]

[0246] A current (10 mA / cm²) was applied to the organic light-emitting devices fabricated in the above experimental and comparative experimental examples. 2 At the baseline, voltage and efficiency were measured, and the results are shown in Tables 1 and 2 below. Here, lifetime T95 refers to the time (hr) required for the brightness to decrease from its initial brightness to 95%.

[0247] [Table 1]

[0248]

[0249]

[0250]

[0251] [Table 2]

[0252]

[0253] [Symbol Explanation]

[0254] 1: Substrate 2: Anode

[0255] 3: Light-emitting layer 4: Cathode

[0256] 5: Hole injection layer; 6: Hole transport layer

[0257] 7: Light-emitting layer; 8: Electron transport layer.

Claims

1. A compound represented by the following chemical formula 1 or 2: [Chemical Formula 1] [Chemical Formula 2] In the chemical formulas 1 and 2, X is O or S. R represents C with or without substitution. 6-60 aryl, where one of R1 to R8 is a substituent represented by the following chemical formula 3, and the remainder is hydrogen or deuterium; or R is a substituent represented by chemical formula 3, where R1 to R8 are each independently hydrogen or deuterium. [Chemical Formula 3] In the chemical formula 3, L represents a single bond; C is either substituted or unsubstituted. 6-60 aryl; or substituted or unsubstituted C containing one or more of N, O and S. 2-60 Hybrid aryl, L1 and L2 are each independent single bonds; 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, Ar1 and Ar2 are each independently substituted or unsubstituted C. 6-60 aryl, or substituted or unsubstituted C, comprising one or more Cs selected from N, O, and S. 2-60 Mixed aromatics, The term "substituted or unsubstituted" refers to a group selected from deuterium; halogen group; nitrile group; nitro group; hydroxyl group; C 1-10 Alkyl; and C 6-30 One or more substituents in the aryl group are substituted or unsubstituted. in, When R is a substituent represented by chemical formula 3, the following structures are excluded from the substituents represented by chemical formula 3: 。 2. The compound according to claim 1, wherein, R is phenyl, biphenyl, or naphthyl. One of R1 to R8 is a substituent represented by the chemical formula 3, and the rest are hydrogen or deuterium.

3. The compound according to claim 1, wherein, When R is a substituent represented by the chemical formula 3, L can be a single bond, phenylene, biphenyl dimethyl, or naphthylene. L1 and L2 are each independently a single bond, phenylene, biphenyl diyl, or naphthylene. Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothiopheneyl, carbazole-9-yl or 9-phenyl-carbazoleyl, wherein Ar1 and Ar2 are not both phenyl and not both biphenyl-4-yl.

4. The compound according to claim 1, wherein, L can be a single bond, phenylene, biphenyl dimethyl, or naphthylene.

5. The compound according to claim 1, wherein, L1 and L2 are each independently a single bond, phenylene, biphenyl dimethyl, or naphthylene.

6. The compound according to claim 1, wherein, Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothiopheneyl, carbazole-9-yl or 9-phenyl-carbazoleyl.

7. The compound according to claim 1, wherein, Ar1 and Ar2 are different from each other.

8. The compound according to claim 1, wherein, The compound represented by chemical formula 1 or chemical formula 2 is selected from any one of the following compounds: 。 9. 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 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 8.

10. The organic light-emitting device according to claim 9, wherein, The organic layer containing the compound is a light-emitting layer.

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