Novel compound and organic light-emitting device containing the same

Abstract

The present invention provides novel compounds and organic light-emitting devices using the same.

Description

Technical Field

[0001] Cross-references to related applications.

[0002] This application claims priority based on Korean Patent Application No. 10-2020-0097604 filed on August 4, 2020 and Korean Patent Application No. 10-2021-0098044 filed on July 26, 2021, and incorporates all disclosures of the Korean patent applications into this specification.

[0003] The present invention relates to novel compounds and organic light-emitting devices containing the same. Background Art

[0004] Organic light emitting diodes (OLEDs) are currently under extensive research due to their wide viewing angles, excellent contrast, and fast response times, as well as their superior brightness, drive voltage, and response speed.

[0005] An organic light-emitting device typically has a structure comprising an anode, a cathode, and an organic layer positioned between the anode and cathode. To improve the efficiency and stability of an organic light-emitting device, the organic layer is often formed from multiple layers composed of different materials. For example, it can be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an organic light-emitting device structure, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed. When these excitons transition back to the ground state, light is emitted.

[0006] As for organic substances used in the organic light-emitting devices described above, there is a continuous demand for the development of new materials.

[0007] Prior art literature

[0008] Patent Literature

[0009] (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826 Summary of the Invention

[0010] Technical issues

[0011] The present invention relates to novel compounds and organic light-emitting devices containing the same.

[0012] Solution to the problem

[0013] The present invention provides a compound represented by the following Chemical Formula 1:

[0014] [Chemical Formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] X is each independently N or CH, and two or more of the above X are N,

[0018] Y is O or S,

[0019] L is a direct bond, or a substituted or unsubstituted C 6-60 arylene groups,

[0020] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 heteroaryl,

[0021] R1 and R2 are each independently hydrogen or deuterium,

[0022] However, at least one of Ar1 and Ar2 is substituted with one or more deuteriums, or at least one of R1 and R2 is deuterium.

[0023] Effects of the Invention

[0024] The compound represented by the above Chemical Formula 1 can be used as a material for an organic layer of an organic light-emitting device, and can achieve improved efficiency, lower driving voltage, and / or improved lifespan characteristics in the organic light-emitting device.

[0025] In particular, the compound represented by the above Chemical Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emitting, electron transport, or electron injection material. BRIEF DESCRIPTION OF THE DRAWINGS

[0026] Figure 1 An example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a hole transport layer 3 , a light-emitting layer 4 , an electron injection and transport layer 5 , and a cathode 6 is shown.

[0027] Figure 2 The diagram shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6. DETAILED DESCRIPTION

[0028] Hereinafter, the present invention will be described in more detail to facilitate understanding.

[0029] (Definition of terms)

[0030] In this manual, It represents a bond to other substituents.

[0031] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; Arylthio Alkylsulfonyl Arylsulfonyl Silyl; boryl; alkyl; cycloalkyl; alkenyl; aryl; aralkyl; aralkenyl; alkylaryl; alkylamino; aralkylamino; heteroarylamino; arylamino; arylphosphino; or a heteroaryl group containing one or more N, O, and S atoms, which may be substituted or unsubstituted with one or more substituents, or with a substituent consisting of two or more of the substituents listed above. For example, a "substituent consisting of two or more substituents" may be a biphenyl group. That is, a biphenyl group may be an aryl group, or it may be interpreted as a substituent consisting of two phenyl groups linked together.

[0032] In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably the number of carbon atoms is 1 to 40. Specifically, the group may have the following structure, but is not limited thereto.

[0033]

[0034] In the present specification, the oxygen of the ester group may be substituted by a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a group of the following structural formula, but is not limited thereto.

[0035]

[0036] In the present specification, the number of carbon atoms in the imide group is not particularly limited, but preferably the number of carbon atoms is 1 to 25. Specifically, the group may have the following structure, but is not limited thereto.

[0037]

[0038] In the present specification, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited thereto.

[0039] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0040] In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

[0041] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 6. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, and 5-methylhexyl.

[0042] In the present specification, the alkenyl group may be linear 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-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethen-1-yl, 2,2-bis(diphenyl-1-yl)ethen-1-yl, stilbene, and styryl, but are not limited thereto.

[0043] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 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. Specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

[0044] In this specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group having aromaticity. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, Base, etc., but not limited to this.

[0045] In the present specification, the heteroaryl group is a heteroaryl group containing one or more of O, N, Si and S as hetero elements, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of the heteroaryl group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo[omicron] oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl and dibenzofuranyl, etc., but are not limited thereto.

[0046] In this specification, the aryl group in aralkyl, aralkenyl, alkylaryl, arylamine, and arylsilyl groups is the same as the examples of aryl groups described above. In this specification, the alkyl group in aralkyl, alkylaryl, and alkylamine groups is the same as the examples of alkyl groups described above. In this specification, the heteroaryl group in heteroarylamine is the same as the examples of heteroaryl groups described above. In this specification, the alkenyl group in aralkenyl is the same as the examples of alkenyl groups described above. In this specification, the description of aryl groups described above is applicable except that an arylene group is a divalent group. In this specification, the description of heteroarylene groups described above is applicable except that a heteroarylene group is a divalent group. In this specification, the description of heteroaryl groups described above is applicable except that a hydrocarbon ring is not a monovalent group but is formed by bonding two substituents. In this specification, the description of aryl or cycloalkyl groups described above is applicable except that a heterocycle is not a monovalent group but is formed by bonding two substituents. In this specification, the description of heteroaryl groups described above is applicable except that a heterocycle is not a monovalent group but is formed by bonding two substituents.

[0047] (Compound)

[0048] The present invention provides a compound represented by the above Chemical Formula 1.

[0049] Next, the above Chemical Formula 1 and the compounds represented by the Chemical Formula are described in detail.

[0050] Each X is independently N or CH, and two or more of the Xs are N. Specifically, all Xs may be N.

[0051] Y is O or S, for example, it can be O.

[0052] L can be a direct bond, substituted or unsubstituted C 6-60 For example, L can be a direct bond, a phenylene group, or a biphenylene group.

[0053] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroaryl.

[0054] Specifically, Ar1 and Ar2 can each independently be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a naphthylphenyl group, a phenanthrenyl group, a dimethylfluorenyl group, a carbazol-9-yl group, a 9-phenyl-9H-carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group. In this case, Ar1 and Ar2 can be unsubstituted or substituted with one or more deuterium groups.

[0055] For example, Ar1 and Ar2 can each independently be an unsubstituted biphenyl group, a terphenyl group, a naphthyl group, a naphthylphenyl group, a phenanthrenyl group, a dimethylfluorenyl group, a carbazole-9-yl group, a 9-phenyl-9H-carbazole group, a dibenzofuranyl group, or a dibenzothienyl group; or a phenyl group that is unsubstituted or substituted with 5 deuterium groups.

[0056] R1 and R2 can each independently be hydrogen or deuterium.

[0057] However, the above Chemical Formula 1 satisfies the above definition, and at least one of Ar1 and Ar2 is substituted with one or more deuteriums, or at least one of R1 and R2 is deuterium.

[0058] For example, the compound represented by the above Chemical Formula 1 may be any one selected from the following compounds:

[0059]

[0060]

[0061]

[0062]

[0063]

[0064] In addition, the present invention provides a method for producing the compound represented by the above Chemical Formula 1 as shown in the following Reaction Formula 1.

[0065] [Reaction formula 1]

[0066]

[0067] In the above Reaction Formula 1, the definitions of X, Y, L, Ar1, Ar2, R1 and R2 are the same as those in Chemical Formula 1. In addition, in Reaction Formula 1, Z is a halogen, preferably chlorine.

[0068] The above reaction formula 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base. The reactive groups used in the Suzuki coupling reaction can be changed according to techniques known in the art. The above production method can be further specified in the production examples described below.

[0069] (Organic Light-Emitting Devices)

[0070] In another aspect, the present invention provides an organic light-emitting device comprising the compound represented by Chemical Formula 1. As an example, the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode disposed opposite 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 the compound represented by Chemical Formula 1.

[0071] The organic layer of the organic light-emitting device of the present invention may be formed of a single layer structure, but may also be formed of a multilayer structure comprising two or more organic layers stacked together. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like as organic layers. However, the structure of the organic light-emitting device is not limited to this, and may include a smaller number of organic layers.

[0072] In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, hole transport layer, or layer that simultaneously injects and transports holes may contain the compound represented by Chemical Formula 1.

[0073] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1.

[0074] The organic layer of the organic light-emitting device of the present invention may be a single-layer structure, but may also be a multilayer structure comprising two or more organic layers stacked together. For example, the organic light-emitting device of the present invention may include, in addition to the light-emitting layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode. However, the structure of the organic light-emitting device is not limited to this, and may include a fewer or greater number of organic layers.

[0075] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device of a structure (normal type) in which the first electrode is an anode and the second electrode is a cathode, and an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device of an inverted structure (inverted type) in which the first electrode is a cathode and the second electrode is an anode, and 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 one embodiment of the present invention is shown in FIG. Figure 1 and 2 .

[0076] Figure 1 The diagram shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6. In the above structure, the compound represented by Chemical Formula 1 may be contained in the hole transport layer.

[0077] Figure 2 The figure shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6. In the above structure, the compound represented by Chemical Formula 1 can be contained in the hole injection layer, the hole transport layer, or the electron suppression layer.

[0078] The organic light-emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers contains the compound represented by Chemical Formula 1. Furthermore, when the organic light-emitting device includes multiple organic layers, the organic layers can be formed of the same substance or different substances.

[0079] For example, an 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. In this case, the device can be manufactured as follows: a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode. An organic layer comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is then formed on the anode. A cathode material is then deposited on the organic layer. Alternatively, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0080] Furthermore, when manufacturing an organic light-emitting device, the compound represented by Chemical Formula 1 can be applied not only by vacuum evaporation but also by solution coating to form an organic layer. Solution coating methods include, but are not limited to, spin coating, dip coating, doctor blade coating, inkjet printing, screen printing, spraying, and roller coating.

[0081] In addition to this method, an organic light-emitting device 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 this.

[0082] As an example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

[0083] The anode material is preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of the anode material include, but are not limited to, 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-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0084] The cathode material is preferably one with a low work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0085] The hole injection layer is a layer that injects holes from the electrode. As a hole injection material, it is preferably a compound that has the ability to transport holes, has the effect of injecting holes from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film forming ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyaniline, and polythiophene conductive polymers, but are not limited thereto.

[0086] The 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 material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. Materials with high hole mobility are suitable. The hole transport material can be a compound represented by Chemical Formula 1, or an arylamine-based organic compound, a conductive polymer, or a block copolymer containing both conjugated and non-conjugated portions, but is not limited thereto.

[0087] The electron suppression layer is formed on the hole transport layer, preferably in contact with the light-emitting layer, and improves the efficiency of the organic light-emitting device by regulating hole mobility, preventing excessive electron migration, and increasing the probability of hole-electron bonding. The electron suppression layer comprises an electron-blocking substance. Examples of such electron-blocking substances include, but are not limited to, the compound represented by Chemical Formula 1 or an arylamine-based organic substance.

[0088] The above-mentioned luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light range. It is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo azole, benzothiazole and benzimidazole compounds; poly(p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorene; rubrene, etc., but are not limited thereto.

[0089] The above-mentioned light-emitting layer may include a host material and a dopant material as described above. The host material may also include an aromatic fused ring derivative or a heterocyclic compound. Specifically, as an aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited thereto.

[0090] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, , diindenopyrene, etc. Styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specific examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetramine. Furthermore, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0091] The hole blocking layer is a layer formed on the light-emitting layer, preferably in contact with the light-emitting layer, and improves the efficiency of the organic light-emitting layer device by adjusting the electron mobility, preventing excessive migration of holes, and increasing the probability of hole-electron bonding. The hole blocking layer contains a hole blocking substance. Examples of such hole blocking substances include azine derivatives including triazine, triazole derivatives, Compounds into which electron-withdrawing groups are introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, phosphine oxide derivatives, and the like.

[0092] The electron injection and transport layer is a layer that injects electrons from the electrode and transports the received electrons to the light-emitting layer, and plays the role of both an electron transport layer and an electron injection layer, and is formed on the light-emitting layer or the hole blocking layer. Such electron injection and transport substances are substances that can well receive electrons from the cathode and transfer them to the light-emitting layer, and substances with high electron mobility are suitable. As specific examples of electron injection and transport substances, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, triazine derivatives, etc., but are not limited to these. Alternatively, it can also be combined with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and the like, as well as their derivatives, metal coordination compounds, or nitrogen-containing five-membered ring derivatives, are used together, but are not limited thereto.

[0093] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)gallium chloride, bis(2-methyl-8-quinolinato)(o-cresol)gallium, bis(2-methyl-8-quinolinato)(1-naphthol)aluminum, and bis(2-methyl-8-quinolinato)(2-naphthol)gallium.

[0094] The organic light-emitting device according to the present invention may be a bottom emission device, a top emission device, or a bidirectional light-emitting device. In particular, it may be a bottom emission device requiring relatively high luminous efficiency.

[0095] In addition, the compound represented by the above Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to being included in an organic light-emitting device.

[0096] [Example 1]

[0097] Example 1-1: Preparation of compound substance (sub) 1-2

[0098] First, compound A-1 was produced as shown below.

[0099]

[0100] Under a nitrogen atmosphere, 2-bromo-6-fluorophenol (100 g, 526.5 mmol) and (2-chloro-6-fluorophenyl)boric acid (91.6 g, 526.5 mmol) were added to tetrahydrofuran (2000 ml), stirred and refluxed. Then, potassium carbonate (218.3 g, 1579.4 mmol) was dissolved in water (218 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (18.2 g, 15.8 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was again added to chloroform (2527 mL) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a black solid compound A-1 (97.3 g, yield 77%, MS: [M+H]+ =241).

[0101] Then, as shown below, Compound A-2 was produced from Compound A-1.

[0102]

[0103] Under a nitrogen atmosphere, A-1 (50 g, 208.3 mmol) and N-bromosuccinimide (37.1 g, 208.3 mmol) were added to chloroform (250 ml), stirred and cooled to 0 ° C. Then, after reacting for 4 hours, the mixture was cooled to room temperature and added to water. Then, the organic layer and the aqueous layer were separated, and the organic layer was concentrated. It was again added to chloroform (662 mL) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column using chloroform and ethyl acetate to produce a white solid compound A-2 (48.3 g, yield 73%, MS: [M+H] + =318.9).

[0104] Then, as shown below, compound A-3 was produced from compound A-2.

[0105]

[0106] Under a nitrogen atmosphere, A-2 (30 g, 100 mmol) was added to dimethylformamide (150 ml), potassium carbonate was added, and the mixture was stirred and heated to 140 ° C. Then, after reacting for 7 hours, the mixture was cooled to room temperature and water was added. Then, the generated solid was filtered. It was again added to chloroform (280 mL) and dissolved, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column using chloroform and ethyl acetate to produce a white solid compound A-3 (21.6 g, yield 77%, MS: [M+H] + =280.9).

[0107] Then, compound A-4 was produced from compound A-3 as shown below.

[0108]

[0109] Under a nitrogen atmosphere, A-3 (20 g, 67.1 mmol) and phenylboronic acid (8.2 g, 67.1 mmol) were added to tetrahydrofuran (400 ml), refluxed and stirred. Then, potassium carbonate (27.8 g, 201.4 mmol) was dissolved in water (28 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (0) (2.3 g, 2 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature and the generated solid was filtered. The solid was added to chloroform (994 mL) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound A-4 (13.3 g, yield 67%, MS: [M+H] + =297).

[0110] Then, as shown below, compound substance 1-1 was produced from compound A-4.

[0111]

[0112] Under a nitrogen atmosphere, A-4 (20 g, 67.6 mmol) and 9H-carbazole-1,3,4,5,6,8-D6 (11.7 g, 67.6 mmol) were added to xylene (400 ml), stirred and refluxed. Then, sodium tert-butoxide (19.5 g, 202.7 mmol) was added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (1 g, 2 mmol) was added. After reacting for 5 hours, the reaction mixture was cooled to room temperature and the generated solid was filtered. The solid was dissolved in chloroform (910 mL), washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column using chloroform and ethyl acetate to produce a white solid compound substance 1-1 (18.8 g, yield 62%, MS: [M+H] + =450.2).

[0113] Then, as shown below, Compound Material 1-2 was produced from Compound Material 1-1.

[0114]

[0115] Under nitrogen atmosphere, material 1-1 (15 g, 33.4 mmol) and bis(pinacolato)diboron (9.3 g, 36.7 mmol) were added to distilled water. The mixture was added to oxane (300ml), stirred and refluxed. Then, potassium acetate (9.6g, 100.2mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium (0) (0.6g, 1mmol) and tricyclohexylphosphine (0.6g, 2mmol) were added. After reacting for 6 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was again added to chloroform (181mL) and dissolved, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a white solid compound substance 1-2 (16.1g, yield 89%, MS: [M+H] + =542.3).

[0116] Example 1-2: Preparation of Compound 2-2

[0117] As shown below, compound substance 2-1 was produced from compound A-4.

[0118]

[0119] Under a nitrogen atmosphere, A-4 (20 g, 37.6 mmol) and 9H-carbazole-1,2,3,4,5,6,7,8-D8 (6.6 g, 37.6 mmol) were added to diphenylmethane (400 ml), stirred and refluxed. Then, sodium tert-butoxide (10.8 g, 112.8 mmol) was added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.6 g, 1.1 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature and the generated solid was filtered. The solid was added to chloroform (509 mL) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column using chloroform and ethyl acetate to produce a light yellow solid compound substance 2-1 (11.2 g, yield 66%, MS: [M+H] + =452.2).

[0120] Then, Compound Material 2-2 was produced from Compound Material 2-1.

[0121]

[0122] Under nitrogen atmosphere, material 2-1 (15 g, 33.2 mmol) and bis(pinacolato)diboron (9.3 g, 36.6 mmol) were added to distilled water. The mixture was added to oxane (300 ml), stirred and refluxed. Then, potassium acetate (9.6 g, 99.7 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium (0) (0.6 g, 1 mmol) and tricyclohexylphosphine (0.6 g, 2 mmol) were added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was again added to chloroform (181 mL) and dissolved, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound substance 2-2 (9.6 g, yield 53%, MS: [M+H] + =544.3).

[0123] Example 1-3: Preparation of Compound 3-2

[0124] As shown below, compound B-1 was produced from compound A-3.

[0125]

[0126] Under a nitrogen atmosphere, A-3 (20 g, 67.1 mmol) and [1,1'-biphenyl]-3-ylboronic acid (13.3 g, 67.1 mmol) were added to tetrahydrofuran (400 ml), stirred and refluxed. Then, potassium carbonate (27.8 g, 201.4 mmol) was dissolved in water (28 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (2.3 g, 2 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was again added to chloroform (500 mL) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound B-1 (15.7 g, yield 63%, MS: [M+H] + =373.1).

[0127] Then, compound substance 3-1 was produced from compound B-1.

[0128]

[0129] Under a nitrogen atmosphere, B-1 (20 g, 53.8 mmol) and 9H-carbazole-1,3,4,5,6,8-D6 (9.3 g, 53.8 mmol) were added to diphenylmethane (400 ml), stirred and refluxed. Then, sodium tert-butoxide (15.5 g, 161.3 mmol) was added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.8 g, 1.6 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature and the generated solid was filtered. The solid was added to chloroform (847 mL) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column using chloroform and ethyl acetate to produce a white solid compound substance 3-1 (21.5 g, yield 76%, MS: [M+H] + =526.2).

[0130] Then, Compound Material 3-2 was produced from Compound Material 3-1.

[0131]

[0132] Under nitrogen atmosphere, material 3-1 (15 g, 28.6 mmol) and bis(pinacolato)diboron (8 g, 31.4 mmol) were added to distilled water. The mixture was added to oxane (300ml), stirred and refluxed. Then, potassium acetate (8.2g, 85.7mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium (0) (0.5g, 0.9mmol) and tricyclohexylphosphine (0.5g, 1.7mmol) were added. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was again added to chloroform (176mL) and dissolved, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound substance 3-2 (13.4g, yield 76%, MS: [M+H] + =618.3).

[0133] [Example 2]

[0134] Example 2-1: Preparation of Compound 1

[0135]

[0136] Under a nitrogen atmosphere, substance 1-2 (10 g, 18.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (4.9 g, 18.5 mmol) were added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.7 g, 55.4 mmol) was dissolved in water (8 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was again added to chloroform (239 mL) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound compound 1 (7.6 g, yield 64%, MS: [M+H] + =647.3).

[0137] Example 2-2: Preparation of Compound 2

[0138]

[0139] Under a nitrogen atmosphere, substance 1-2 (10 g, 18.5 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.3 g, 18.5 mmol) were added to tetrahydrofuran (200 ml), stirred, and refluxed. Potassium carbonate (7.7 g, 55.4 mmol) was then added to the mixture, stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature, and the organic and aqueous layers were separated and distilled. The organic layer was dissolved in chloroform (267 mL) again, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound 2 (8.8 g, yield 66%, MS: [M+H] + =723.3).

[0140] Example 2-3: Preparation of Compound 3

[0141]

[0142] Under a nitrogen atmosphere, substance 1-2 (10 g, 18.5 mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.3 g, 18.5 mmol) were added to tetrahydrofuran (200 ml), stirred, and refluxed. Potassium carbonate (7.7 g, 55.4 mmol) was then added to the mixture, stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 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 and distilled. The organic layer was dissolved in chloroform (267 mL) again, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound 3 (7.7 g, yield 58%, MS: [M+H] + =723.3).

[0143] Example 2-4: Preparation of Compound 4

[0144]

[0145] Under a nitrogen atmosphere, substance 1-2 (10 g, 18.5 mmol) and 2-chloro-4-(naphthalene-2-yl)-6-phenyl-1,3,5-triazine (6.9 g, 18.5 mmol) were added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.7 g, 55.4 mmol) was dissolved in water (8 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was again added to chloroform (257 mL) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound compound 4 (7.1 g, yield 55%, MS: [M+H] + =697.3).

[0146] Example 2-5: Preparation of Compound 5

[0147]

[0148] Under a nitrogen atmosphere, substance 1-2 (10 g, 18.5 mmol) and 2-chloro-4-(naphthalene-1-yl)-6-phenyl-1,3,5-triazine (6.9 g, 18.5 mmol) were added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.7 g, 55.4 mmol) was dissolved in water (8 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was again added to chloroform (257 mL) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound compound 5 (7.5 g, yield 58%, MS: [M+H] + =697.3).

[0149] Example 2-6: Preparation of Compound 6

[0150]

[0151] Under a nitrogen atmosphere, substance 1-2 (10 g, 18.5 mmol) and 9-(4-chloro-6-phenyl-1,3,5-triazine-2-yl)-9H-carbazole (6.6 g, 18.5 mmol) were added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.7 g, 55.4 mmol) was dissolved in water (8 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was again added to chloroform (272 mL) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound compound 6 (9.9 g, yield 73%, MS: [M+H] + =736.3).

[0152] Example 2-7: Preparation of Compound 7

[0153]

[0154] Under a nitrogen atmosphere, Substance 1-2 (10 g, 18.5 mmol) and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (6.6 g, 18.5 mmol) were added to tetrahydrofuran (200 ml), stirred, and refluxed. Potassium carbonate (7.7 g, 55.4 mmol) was then added to the solution in water (8 ml). After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated and distilled. The organic layer was dissolved in chloroform (272 mL) again, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound 7 (10.7 g, yield 79%, MS: [M+H] + =737.3).

[0155] Example 2-8: Preparation of Compound 8

[0156]

[0157] Under a nitrogen atmosphere, Substance 1-2 (10 g, 18.5 mmol) and 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (6.6 g, 18.5 mmol) were added to tetrahydrofuran (200 ml), stirred, and refluxed. Potassium carbonate (7.7 g, 55.4 mmol) was then added to the mixture, stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature, and the organic and aqueous layers were separated and distilled. The organic layer was dissolved in chloroform (272 mL) again, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound 8 (10.9 g, yield 80%, MS: [M+H] + =737.3).

[0158] Example 2-9: Preparation of Compound 9

[0159]

[0160] Under a nitrogen atmosphere, Substance 1-2 (10 g, 18.5 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (6.6 g, 18.5 mmol) were added to tetrahydrofuran (200 ml), stirred, and refluxed. Potassium carbonate (7.7 g, 55.4 mmol) was then added to the mixture, stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 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 and distilled. The organic layer was dissolved in chloroform (267 mL) again, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound 9 (8.3 g, yield 62%, MS: [M+H] + =723.3).

[0161] Example 2-10: Preparation of Compound 10

[0162]

[0163] Under a nitrogen atmosphere, substance 1-2 (10 g, 18.5 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine (6.9 g, 18.5 mmol) were added to tetrahydrofuran (200 ml), stirred, and refluxed. Potassium carbonate (7.7 g, 55.4 mmol) was then added to the mixture, stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated and distilled. The organic layer was dissolved in chloroform (278 mL) again, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound 10 (10.1 g, yield 73%, MS: [M+H] + =753.3).

[0164] Example 2-11: Preparation of Compound 11

[0165]

[0166] Under a nitrogen atmosphere, substance 1-2 (10 g, 18.5 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-1-yl)-6-phenyl-1,3,5-triazine (6.9 g, 18.5 mmol) were added to tetrahydrofuran (200 ml), stirred, and refluxed. Potassium carbonate (7.7 g, 55.4 mmol) was then added to the mixture, stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated and distilled. The organic layer was dissolved in chloroform (268 mL) again, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound 11 (10 g, yield 75%, MS: [M+H] + =726.3).

[0167] Example 2-12: Preparation of Compound 12

[0168]

[0169] Under a nitrogen atmosphere, substance 2-2 (10 g, 18.4 mmol) and 9-(4-chloro-6-phenyl-1,3,5-triazine-2-yl)-9H-carbazole (6.5 g, 18.4 mmol) were added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.6 g, 55.2 mmol) was dissolved in water (8 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was again added to chloroform (271 mL) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound compound 12 (8.3 g, yield 61%, MS: [M+H] + =738).

[0170] Example 2-13: Preparation of Compound 13

[0171]

[0172] Under a nitrogen atmosphere, substance 1-2 (10 g, 18.5 mmol) and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine (5 g, 18.5 mmol) were added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.7 g, 55.4 mmol) was dissolved in water (8 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was again added to chloroform (241 mL) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound compound 13 (9 g, yield 75%, MS: [M+H] + =652.3).

[0173] Example 2-14: Preparation of Compound 14

[0174]

[0175] Under a nitrogen atmosphere, substance 1-2 (10 g, 18.5 mmol) and 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.1 g, 18.5 mmol) were added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.7 g, 55.4 mmol) was dissolved in water (8 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was again added to chloroform (243 mL) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound compound 14 (8.9 g, yield 73%, MS: [M+H] + =657.3).

[0176] Example 2-15: Preparation of Compound 15

[0177]

[0178] Under a nitrogen atmosphere, substance 2-2 (10 g, 18.4 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (5.4 g, 18.4 mmol) were added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.6 g, 55.2 mmol) was dissolved in water (8 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was again added to chloroform (239 mL) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound compound 15 (8.6 g, yield 72%, MS: [M+H] + =649.3).

[0179] Example 2-16: Preparation of Compound 16

[0180]

[0181] Under a nitrogen atmosphere, substance 3-2 (10 g, 16.1 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (4.3 g, 16.1 mmol) were added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (6.7 g, 48.4 mmol) was dissolved in water (7 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was again added to chloroform (234 mL) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a light yellow solid compound compound 16 (8.8 g, yield 75%, MS: [M+H] + =725.3).

[0182] [Experimental example]

[0183] Experimental Example 1

[0184] ITO (indium tin oxide) The thickness of the glass substrate coated with a film is placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent uses Fischer Co. products, and the distilled water uses distilled water filtered twice by a filter manufactured by Millipore Co. After the ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed and dried with a solvent of isopropyl alcohol, acetone, and methanol, and then the substrate is transported to a plasma cleaning machine. In addition, after the above-mentioned substrate is cleaned for 5 minutes, the substrate is transported to a vacuum deposition machine.

[0185] On the ITO transparent electrode prepared in this way, the following HI-1 compound was applied as The hole injection layer was formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, the following HT-1 compound was added as The hole transport layer was formed by thermal vacuum deposition of a thickness of 1000 nm. On the HT-1 vapor-deposited film, the following HT-2 compound was added to form a hole transport layer. The electron blocking layer is formed by vacuum deposition of a thickness of 1000 nm.

[0186] On the HT-2 evaporated film, as a light-emitting layer, the compound 1 prepared in Example 2-1, the following YGH-1 compound, and the phosphorescent dopant YGD-1 were co-evaporated at a weight ratio of 44:44:12 to form On the above-mentioned luminescent layer, the following ET-1 compound was added as The electron transport layer was formed by vacuum evaporation of a thickness of 1000 nm. On the electron transport layer, the following ET-2 compound and Li were vacuum evaporated at a weight ratio of 98:2 to form On the electron injection layer, A cathode is formed by vapor-depositing aluminum to a thickness of 100 Å.

[0187]

[0188] In the above process, the evaporation rate of organic matter is maintained at Aluminum maintenance The evaporation speed is 1×10 -7 ~5×10 -8 Entrust.

[0189] Experimental Examples 2 to 10

[0190] An organic light-emitting device was manufactured by the same method as in Experimental Example 1, except that the compounds listed in Table 1 below were used instead of Compound 1 in Example 2-1.

[0191] Comparative Experimental Examples 1 to 3

[0192] An organic light-emitting device was manufactured by the same method as in Experimental Example 1, except that the compounds listed in Table 1 below were used instead of Compound 1 of Example 2-1. The compounds CE1 to CE3 in Table 1 below are as follows.

[0193]

[0194] In the above experimental examples and comparative experimental examples, the organic light emitting device was operated at 10 mA / cm 2 The voltage and efficiency were measured at a current density of 50 mA / cm 2 The lifetime was measured at a current density of 1.5 Å, and the results are shown in Table 1. LT95 represents the time required to achieve 95% of the initial luminance.

[0195] [Table 1]

[0196] [Table 1]

[0197]

[0198] As shown in Table 1 above, the compounds of the present invention, when used as light-emitting layer materials, exhibit superior efficiency and lifetime compared to the comparative experimental examples. Substitution of the dibenzofuranyl group as a core substituent with a triazine or carbazolyl group demonstrates increased electronic stability. In particular, substitution of one or more deuterium groups on the additional aryl and carbazolyl groups exhibits superior lifetime enhancement. This also demonstrates increased electronic stability.

[0199] [Explanation of symbols]

[0200] 1: Substrate 2: Anode

[0201] 3: Hole transport layer 4: Light-emitting layer

[0202] 5: Electron injection and transport layer 6: Cathode

[0203] 7: Hole injection layer 8: Electron suppression layer

[0204] 9: Hole blocking layer.

Claims

1. A compound represented by the following chemical formula 1: Chemical formula 1 In the chemical formula 1, X is each independently N or CH, and two or more of the X are N, Y is O or S, L is a C that is directly bonded, or substituted or unsubstituted with one or more deuteriums. 6-20 arylene groups, Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, phenanthrenyl, dimethylfluorenyl, carbazol-9-yl, 9-phenyl-9H-carbazolyl, dibenzofuranyl or dibenzothiophenyl, wherein Ar1 and Ar2 are unsubstituted or substituted with one or more deuteriums, R1 and R2 are each independently hydrogen or deuterium, However, at least one of Ar1 and Ar2 is substituted with one or more deuteriums, or at least one of R1 and R2 is deuterium, and Provided that the compound represented by Chemical Formula 1 does not include the following compounds:

2. The compound according to claim 1, wherein L is a direct bond, a phenylene group, or a biphenylene group.

3. The compound according to claim 1, wherein All X are N.

4. The compound according to claim 1, wherein The compound represented by Chemical Formula 1 is any one selected from the following compounds:

5. An organic light-emitting device, wherein: include: 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 the compound according to any one of claims 1 to 4. The organic light-emitting device according to claim 5 , wherein: The organic layer containing the compound is a light-emitting layer.

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