Compound and organic light-emitting device containing the same

Abstract

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

Description

Technical Field

[0001] Cross-references to related applications

[0002] This application claims the priority based on Korean Patent Application No. 10-2018-0114406 filed on September 21, 2018 and Korean Patent Application No. 10-2019-0115563 filed on September 19, 2019, and incorporates all the contents disclosed in the documents of the Korean patent applications as a part of this specification.

[0003] The present invention relates to a compound and an organic light-emitting device using the same. Background Art

[0004] Generally speaking, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light-emitting devices using the organic light-emitting phenomenon have wide viewing angles, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, so a lot of research is being carried out.

[0005] An organic light-emitting device generally has a structure including an anode and a cathode and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light-emitting device, the organic layer is usually formed by a multilayer structure composed of different substances, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. For such an organic light-emitting device structure, if 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, and when the excitons transition back to the ground state, light is emitted.

[0006] As for organic substances used for organic light-emitting devices as described above, development of new materials continues to be required.

[0007] Prior art literature

[0008] Patent Literature

[0009] (Patent Document 0001) Korean Patent Publication No. 10-2013-073537 Summary of the invention

[0010] Technical issues

[0011] The present invention relates to a compound and an organic light-emitting device comprising 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] X1, X2 and X3 are each independently CH or N, but two or more of X1, X2 and X3 are N,

[0018] Y is S or O,

[0019] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or C containing one or more heteroatoms selected from N, O and S 5-60 Heteroaryl,

[0020] L1 is a direct bond; substituted or unsubstituted C 6-60 or a C containing one or more heteroatoms selected from N, O and S 5-60 Heteroarylene,

[0021] L2 is a direct bond, or a substituted or unsubstituted C 6-60 Arylene,

[0022] R1 and R2 are each independently hydrogen, or substituted or unsubstituted C 1-60 alkyl,

[0023] m and n are each independently an integer of 0 to 3.

[0024] In addition, the present invention provides an organic light-emitting device, which includes: a first electrode, a second electrode opposite to the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein one or more of the organic layers contains the compound of the present invention.

[0025] Effects of the Invention

[0026] 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, in which improved efficiency, low driving voltage and / or improved life characteristics can be achieved. In particular, the compound represented by the above chemical formula 1 can be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport or electron injection. BRIEF DESCRIPTION OF THE DRAWINGS

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

[0028] Figure 2The diagram shows an example of an organic light-emitting device composed 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 DESCRIPTION

[0029] In the following, the present invention will be described in more detail to help understanding the present invention.

[0030] The present invention provides a compound represented by the following Chemical Formula 1.

[0031] [Chemical formula 1]

[0032]

[0033] In the above chemical formula 1,

[0034] X1, X2 and X3 are each independently CH or N, but two or more of X1, X2 and X3 are N,

[0035] Y is S or O,

[0036] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or C containing one or more heteroatoms selected from N, O and S 5-60 Heteroaryl,

[0037] L1 is a direct bond; substituted or unsubstituted C 6-60 or a C containing one or more heteroatoms selected from N, O and S 5-60 Heteroarylene,

[0038] L2 is a direct bond, or a substituted or unsubstituted C 6-60 Arylene,

[0039] R1 and R2 are each independently hydrogen, or substituted or unsubstituted C 1-60 alkyl,

[0040] m and n are each independently an integer of 0 to 3.

[0041] In this manual, It represents the bond to other substituents.

[0042] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; a halogen group; a nitrile 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 ( Alkyl thioxy); arylthio ( Aryl thioxy); alkylsulfonyl ( Alkyl sulfoxy); arylsulfonyl ( The invention also includes the following: aryl sulfoxyl group, silyl group, boryl group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamino group, aralkylamino group, heteroarylamino group, arylamino group, arylphosphino group, or substituted or unsubstituted with one or more substituents in a heterocyclic group containing one or more N, O and S atoms, or substituted or unsubstituted with a substituent formed by connecting two or more substituents among the substituents exemplified above. For example, "a substituent formed by connecting two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may also be interpreted as a substituent formed by connecting two phenyl groups.

[0043] 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.

[0044]

[0045] In the present specification, in the ester group, 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 group may be a group of the following structural formula, but is not limited thereto.

[0046]

[0047] In the present specification, the number of carbon atoms in the imide group is not particularly limited, but the number of carbon atoms is preferably 1 to 25. Specifically, the group may have the following structure, but is not limited thereto.

[0048]

[0049] 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.

[0050] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0051] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0052] In the present 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 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, and 5-methylhexyl, but are not limited thereto.

[0053] 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 number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are 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-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0054] In the present 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. Specifically, there are 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., but are not limited thereto.

[0055] In the present 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. 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 it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, yl, fluorenyl, etc., but are not limited to these.

[0056] In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. etc. However, the present invention is not limited thereto.

[0057] In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl and dibenzofuranyl, but are not limited thereto.

[0058] In this specification, the aryl group in aralkyl, aralkenyl, alkylaryl, and arylamine is the same as the example of the aryl group described above. In this specification, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the example of the alkyl group described above. In this specification, the heteroaryl group in heteroarylamine can be applied to the above description of the heterocyclic group. In this specification, the alkenyl group in aralkenyl is the same as the example of the alkenyl group described above. In this specification, the arylene group is a divalent group, and the above description of the aryl group can be applied. In this specification, the heteroarylene group is a divalent group, and the above description of the heterocyclic group can be applied. In this specification, the hydrocarbon ring is not a monovalent group, but is formed by combining two substituents, and the above description of the aryl group or cycloalkyl group can be applied. In this specification, the heterocycle is not a monovalent group, but is formed by combining two substituents, and the above description of the heterocyclic group can be applied.

[0059] Preferably, the compound represented by the above Chemical Formula 1 may be any one selected from the compounds represented by the following Chemical Formulas 2 to 5:

[0060] [Chemical formula 2]

[0061]

[0062] [Chemical formula 3]

[0063]

[0064] [Chemical formula 4]

[0065]

[0066] [Chemical formula 5]

[0067]

[0068] In the above chemical formulas 2 to 5,

[0069] X1, X2, X3, Y, L1, L2, R1, R2, Ar1, Ar2, m and n are the same as defined above.

[0070] Preferably, Ar1 and Ar2 can each independently be any one selected from the following groups:

[0071]

[0072] Preferably, L1 may be a direct bond or a phenylene group.

[0073] Preferably, L2 may be a direct bond, a phenylene group or a naphthylene group.

[0074] Preferably, R1 and R2 may each independently be hydrogen.

[0075] Preferably, m and n may be 0 or 1 each independently.

[0076] Preferably, the compound represented by the above Chemical Formula 1 may be any one selected from the following compounds:

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084] The compound represented by Chemical Formula 1 according to the present invention is prepared by The azole (benzothiazole) contains a triazine group on the benzene ring side and an N-substituted carbazole group on the heterocyclic side, so that the electron mobility is significantly improved, and therefore, it can have high efficiency, low driving voltage, high brightness, long life, etc.

[0085] The compound represented by the above Chemical Formula 1 can be produced by the following Reaction Formulas 1-1 and 1-2.

[0086] [Reaction formula 1-1]

[0087]

[0088] [Reaction 1-2]

[0089]

[0090] In the above reaction formula 1, X is a halogen, preferably bromine or chlorine, and the description of the remaining substituents is the same as the above definitions.

[0091] The above reaction is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactants and catalysts used in the above reaction can be changed according to the techniques known in the art. The above production method can be further embodied in the production examples described below.

[0092] In addition, the present invention provides an organic light-emitting device including the compound represented by the above Chemical Formula 1. As an example, the present invention provides an organic light-emitting device, including: a first electrode, a second electrode provided opposite to the above first electrode, and one or more organic layers provided between the above first electrode and the above second electrode, wherein one or more of the organic layers includes the compound represented by the above Chemical Formula 1.

[0093] The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. 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, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0094] 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, the hole transport layer, or the layer that simultaneously injects and transports holes includes the compound represented by Chemical Formula 1.

[0095] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1.

[0096] In addition, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by Chemical Formula 1.

[0097] In addition, the electron transport layer, the electron injection layer, or the layer that simultaneously performs electron injection and electron transport contains the compound represented by the above chemical formula 1. In particular, the compound represented by the chemical formula 1 according to the present invention has excellent thermal stability, a high HOMO energy level of 6.0 eV or more, a high triplet energy (ET), and hole stability. In addition, when the compound represented by the above chemical formula 1 is used for an organic layer that can simultaneously perform electron injection and electron transport, an n-type dopant used in this field can be mixed and used.

[0098] In addition, the organic layer includes a light emitting layer and an electron transport layer, and the electron transport layer may include the compound represented by Chemical Formula 1.

[0099] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which 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 having an inverse 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 one embodiment of the present invention is shown in FIG. Figure 1 and Figure 2 .

[0100] Figure 1 The figure shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In the above structure, the compound represented by the above Chemical Formula 1 may be contained in the above light emitting layer.

[0101] 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 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4. In the structure described above, the compound represented by the above chemical formula 1 may be contained in one or more of the above hole injection layer, hole transport layer, light-emitting layer, and electron transport layer.

[0102] 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 the above Chemical Formula 1. In addition, when the organic light-emitting device includes a plurality of organic layers, the organic layers can be formed of the same substance or different substances.

[0103] 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. In this case, it can be manufactured as follows: a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation is used to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode substance, an organic layer, and an anode substance on a substrate.

[0104] In addition, the compound represented by the above chemical formula 1 can be used not only by vacuum evaporation method but also by solution coating method to form an organic layer when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating method, dip coating method, blade coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited to these.

[0105] In addition to these methods, 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.

[0106] 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.

[0107] As the above-mentioned anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of the above-mentioned anode material include metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0108] In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function. 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 alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0109] The hole injection layer is a layer for injecting holes from the electrode. As a hole injection material, it is preferably a compound having the ability to transport holes, the effect of injecting holes from the anode, an excellent hole injection effect for the light-emitting layer or the light-emitting material, and a compound having excellent thin film forming ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. 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. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyanilines, and polythiophene conductive polymers, but are not limited thereto.

[0110] The hole transport layer is a layer that receives holes from the hole injection layer and transfers the holes 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. A material with a large hole mobility is suitable. Specific examples include arylamine organics, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited thereto.

[0111] 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 region, and 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.

[0112] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material includes 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 to these.

[0113] 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, and there are pyrene, anthracene, , diindenopyrene, etc. The styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as a metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0114] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. As an electron transport material, it is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer. Materials with large electron mobility are suitable. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxy copper-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 function and accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.

[0115] The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound that has the ability to transport electrons, has the effect of injecting electrons from the cathode, has an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from migrating to the hole injection layer, and has excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0116] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, 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.

[0117] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0118] 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 an organic light emitting device.

[0119] Preparation Example 1: Preparation of Intermediate Compound A1

[0120]

[0121] Preparation of Compound A1-1

[0122] 2,6-dichlorobenzo[d]thiazole (30 g, 0.147 mol), 9H-carbazole (24.6 g, 0.147 mol) and potassium phosphate (62.40 g, 0.294 mol) were added to dimethylacetamide (300 mL) and refluxed. After reflux for 12 hours, the reaction was completed and cooled to room temperature. After filtration, the mixture was washed with water and ethanol and dried to obtain compound A1-1 (37.9 g, yield 77%; MS: [M+H] + =335).

[0123] Preparation of Compound A1

[0124] Compound A1-1 (37.9 g, 88.9 mmol) was dissolved in 1,4-dihydrochloric acid. alkane (500ml). After adding bis(pinacolato)diboron (33.9g, 133.4mmol), potassium acetate (potassium acetate) (26.2g, 266.7mmol) and Pd(dppf)Cl2 (1.9g, 2.68mmol), stir at 120°C for 8 hours. After the reaction is completed, cool to room temperature and then filter. The filtered solution is distilled to remove the solvent. After extraction with chloroform and water, the organic layer is dried with MgSO4, concentrated, and recrystallized with ethyl acetate to obtain the intermediate compound A1 (32.0g, yield 85%; MS: [M+H] + =503).

[0125] Preparation Example 2: Preparation of Intermediate Compound B1

[0126]

[0127] Preparation of compound B1-1

[0128] (4-(9H-carbazol-9-yl)phenyl)boronicacid (25 g, 87.1 mmol) and 2,6-dichlorobenzo[d]thiazole (17.8 g, 87.1 mmol) were added to distilled water. Then, cesium carbonate (85.1 g, 261.2 mmol) was dissolved in water (100 mL), added to a round-bottom flask, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (1.4 g, 2.6 mmol) was added, and after reflux for 3 hours, the reaction was completed and cooled to room temperature. After filtering, the mixture was washed with water and ethanol and dried to obtain compound B1-1 (28.5 g, yield 80%; MS: [M+H] + =411).

[0129] Preparation of Compound B1

[0130] B1-1 (18 g, 43.8 mmol) was dissolved in 1,4-dichlorobenzene. alkane (500ml). After adding bis(pinacolato)diboron (16.7g, 65.7mmol), potassium acetate (12.9g, 131.41mmol) and Pd(PCy)2.(OAc)2 (1g, 1.31mmol), stir at 120°C for 8 hours. After the reaction is completed, cool to room temperature and then filter. Distill the filtered solution to remove the solvent. After extraction with chloroform and water, the organic layer is dried over MgSO4, concentrated, and recrystallized from ethanol to obtain compound B1 (18.3g, yield 83%; MS: [M+H]+ =411).

[0131] Preparation Example 3: Preparation of Intermediate Compound C1

[0132]

[0133] Preparation of Compound C1-1

[0134] (3-(9H-carbazol-9-yl)phenyl)boronicacid (20 g, 69.7 mmol) and 2,6-dichlorobenzo[d]thiazole (14.2 g, 69.7 mmol) were added to distilled water. Then, cesium carbonate (68.1 g, 209.0 mmol) was dissolved in water (100 mL), added to a round-bottom flask, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (1.1 g, 2.1 mmol) was added, and after reflux for 3 hours, the reaction was completed and cooled to room temperature. After filtration, the mixture was washed with water and ethanol and dried to obtain compound C1-1 (20 g, yield 70%; MS: [M+H] + =395).

[0135] Preparation of Compound C1

[0136] C1-1 (20 g, 48.7 mmol) was dissolved in 1,4-dihydrochloric acid. alkane (500ml). After adding bis(pinacolato)diboron (18.5g, 73.0mmol), potassium acetate (14.3g, 146.0mmol) and Pd(PCy)2.(OAc)2 (1.1g, 1.46mmol), stir at 120°C for 8 hours. After the reaction is completed, cool to room temperature and then filter. Distill the filtered solution to remove the solvent. After extraction with chloroform and water, the organic layer is dried with MgSO4, concentrated, and recrystallized with ethanol to obtain compound C1 (18g, yield 74%; MS: [M+H] + =487).

[0137] Example 1: Preparation of Compound 1

[0138]

[0139] The intermediate compound 1A (15 g, 35.2 mmol) synthesized in Preparation Example 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) (9.4 g, 35.2 mmol) were added to tetrahydrofuran (150 ml). Then, calcium carbonate (19.5 g, 140.8 mmol) was dissolved in water (50 mL), added to a round-bottom flask, and refluxed. Then, tetrakis(triphenylphosphine)palladium (0) (1.2 g, 3 mol%) was added, and after refluxing for 3 hours, the reaction was cooled to room temperature when it was finished. After filtering, it was washed with water and ethanol, then dissolved in chloroform, extracted with water, and the organic layer was dried with magnesium sulfate. Then, the organic layer was distilled under reduced pressure and recrystallized with ethyl acetate. The generated solid was filtered and dried to produce compound 1 (12.5 g, 67%, MS: [M+H] + =532).

[0140] Example 2: Preparation of Compound 2

[0141]

[0142] The intermediate compound 1A (15 g, 35.2 mmol) synthesized in Preparation Example 1 and 2-([1,1'-biphenyl]-4-yl)-4-(4-bromophenyl)-6-phenyl-1,3,5-triazine (2-([1,1'-biphenyl]-4-yl)-4-(4-bromophenyl)-6-phenyl-1,3,5-triazine) (16.3 g, 35.2 mmol) were added to tetrahydrofuran (150 ml). Then, calcium carbonate (19.5 g, 140.8 mmol) was dissolved in water (50 mL), added to a round-bottom flask, and refluxed. Then, tetrakis(triphenylphosphine)palladium(0) (1.2 g, 3 mol%) was added, and after reflux for 3 hours, the reaction was completed and cooled to room temperature. After filtering, the mixture was washed with water and ethanol, dissolved in chloroform, extracted with water, and the organic layer was dried with magnesium sulfate. Then, the organic layer was distilled under reduced pressure and recrystallized from ethyl acetate. The generated solid was filtered and dried to produce compound 2 (17.6 g, 73%, MS: [M+H] + =684).

[0143] Example 3: Preparation of Compound 3

[0144]

[0145] The intermediate compound 1A (15 g, 35.2 mmol) synthesized in Preparation Example 1 and 2-(4-bromophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (16.8 g, 35.2 mmol) were added to tetrahydrofuran (150 ml). Then, calcium carbonate (19.5 g, 140.8 mmol) was dissolved in water (50 mL), added to a round-bottom flask, and refluxed. Then, tetrakis(triphenylphosphine)palladium(0) (1.2 g, 3 mol%) was added, and after reflux for 3 hours, the reaction was completed and cooled to room temperature. After filtration, the mixture was washed with water and ethanol, dissolved in chloroform, extracted with water, and the organic layer was dried with magnesium sulfate. Then, the organic layer was distilled under reduced pressure and recrystallized from ethyl acetate. The generated solid was filtered and dried to produce compound 3 (10.3 g, 42%, MS: [M+H] + =698).

[0146] Example 4: Preparation of Compound 4

[0147]

[0148] The intermediate compound 1A (15 g, 35.2 mmol) synthesized in Preparation Example 1 and 9-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole (16.8 g, 35.2 mmol) were added to tetrahydrofuran (150 ml). Then, calcium carbonate (19.5 g, 140.8 mmol) was dissolved in water (50 mL), added to a round-bottom flask, and refluxed. Then, tetrakis(triphenylphosphine)palladium(0) (1.2 g, 3 mol%) was added, and after reflux for 3 hours, the reaction was completed and cooled to room temperature. After filtering, it was washed with water and ethanol, then dissolved in chloroform, extracted with water, and the organic layer was dried with magnesium sulfate. Then, the organic layer was distilled under reduced pressure and recrystallized with ethyl acetate. The generated solid was filtered and dried to prepare compound 4 (11.5 g, 47%, MS: [M+H] + =697).

[0149] Example 5: Preparation of Compound 5

[0150]

[0151] The intermediate compound A1 synthesized in Preparation Example 1 (15 g, 35.2 mmol) and 2-(4-bromophenyl)-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine (17.4 g, 35.2 mmol) were added to tetrahydrofuran (150 ml). Then, calcium carbonate (19.5 g, 140.8 mmol) was dissolved in water (50 mL), added to a round-bottom flask, and refluxed. Then, tetrakis(triphenylphosphine)palladium(0) (1.2 g, 3 mol%) was added, and after reflux for 3 hours, the reaction was completed and cooled to room temperature. After filtering, the mixture was washed with water and ethanol, then dissolved in chloroform, extracted with water, and the organic layer was dried with magnesium sulfate. Then, the organic layer was distilled under reduced pressure and recrystallized from ethyl acetate. The generated solid was filtered and dried to produce compound 5 (16.1 g, 64%, MS: [M+H] + =714).

[0152] Example 6: Preparation of Compound 6

[0153]

[0154] The intermediate compound B1 (15 g, 29.9 mmol) synthesized in Preparation Example 2 and 2-chloro-4,6-diphenyl-1,3,5-triazine (8.0 g, 29.9 mmol) were added to tetrahydrofuran (150 ml). Then, calcium carbonate (16.5 g, 119.5 mmol) was dissolved in water (40 mL), added to a round-bottom flask, and refluxed. Then, tetrakis(triphenylphosphine)palladium(0) (1.0 g, 3 mol%) was added, and after refluxing for 3 hours, the reaction was cooled to room temperature when it was finished. After filtering, it was washed with water and ethanol, then dissolved in chloroform, extracted with water, and the organic layer was dried with magnesium sulfate. Then, the organic layer was distilled under reduced pressure and recrystallized with ethyl acetate. The generated solid was filtered and dried to produce compound 6 (12.7 g, 70%, MS: [M+H] + =608).

[0155] Example 7: Preparation of Compound 7

[0156]

[0157] The intermediate compound C1 (15 g, 30.9 mmol) synthesized in Preparation Example 3 and 2-chloro-4,6-diphenyl-1,3,5-triazine (8.2 g, 30.9 mmol) were added to tetrahydrofuran (150 ml). Then, calcium carbonate (17.1 g, 123.4 mmol) was dissolved in water (40 mL), added to a round-bottom flask, and refluxed. Then, tetrakis(triphenylphosphine)palladium (0) (1.1 g, 3 mol%) was added, and after refluxing for 3 hours, the reaction was cooled to room temperature when it was finished. After filtering, it was washed with water and ethanol, then dissolved in chloroform, extracted with water, and the organic layer was dried with magnesium sulfate. Then, the organic layer was distilled under reduced pressure and recrystallized with ethyl acetate. The generated solid was filtered and dried to produce compound 7 (6.0 g, 33%, MS: [M+H] + =592).

[0158] [Experimental example]

[0159] Experimental Example 1-1

[0160] ITO (indium tin oxide) is used The glass substrate coated with a film of a thickness of 10000 is placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent uses a product of Fischer Co., and the distilled water uses distilled water filtered twice by a filter manufactured by Millipore Co. After the ITO is washed for 30 minutes, ultrasonic washing is repeated twice with distilled water for 10 minutes. After the distilled water washing is completed, ultrasonic washing is carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate is cleaned for 5 minutes using oxygen plasma, the substrate is transported to a vacuum evaporator.

[0161] 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 deposited at 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 deposited at On the HT-2 evaporated film, as a light-emitting layer, the compound 1 prepared in Example 1 and the following YGH1 compound and the phosphorescent dopant YGD-1 were co-evaporated in a ratio of 44:44:12 to form an electron blocking layer. On the above-mentioned luminescent layer, the following ET-1 compound was added in the amount of The following ET-2 compound was further deposited with a thickness of Aluminum was deposited on the electron injection layer with a thickness of 1000 nm and 2% by weight of Li to form an electron transport layer and an electron injection layer. A thickness of is evaporated to form a cathode.

[0162]

[0163] In the above process, the evaporation rate of organic matter is maintained Aluminum maintenance The evaporation speed is 1×10 -7 ~5×10 -8 Entrust.

[0164] Experimental Examples 1-2 to 1-7

[0165] An organic light-emitting device was manufactured by the same method as in Experimental Example 1-1, except that the compounds listed in Table 1 below were used instead of Compound 1 of Example 1.

[0166] Comparative Experimental Examples 1-1 to 1-4

[0167] In Experimental Example 1-1, an organic light-emitting device was manufactured by the same method as in Experimental Example 1-1, except that the compound described in Table 1 below was used instead of Compound 1 of Example 1. The compounds CE1 to CE4 of Table 1 below are as follows.

[0168]

[0169] The organic light emitting devices in the above experimental examples and comparative experimental examples were tested at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 50 mA / cm 2 The time required for the luminance to reach 95% of the initial luminance (LT95) was measured at a current density of . The results are shown in Table 1 below.

[0170]

Table 1

[0171]

[0172] As shown in Table 1, it was confirmed that when the compound of the present invention was used as a light-emitting layer substance, it exhibited excellent properties in terms of efficiency and lifetime compared with the comparative experimental examples.

[0173]

Explanation of symbols

[0174] 1: Substrate 2: Anode

[0175] 3: Light-emitting layer 4: Cathode

[0176] 5: Hole injection layer 6: Hole transport layer

[0177] 7: Light-emitting layer 8: Electron transport layer.

Claims

1. A compound represented by the following chemical formula 1: Chemical formula 1 In the chemical formula 1, X1, X2 and X3 are each independently CH or N, provided that at least 2 of X1, X2 and X3 are N, Y is S or O, Ar1 and Ar2 are each independently selected from any one of the following groups: L1 is a direct bond; or a phenylene group, L2 is a direct bond, a phenylene group or a naphthylene group, R1 and R2 are each independently hydrogen, m and n are each independently an integer of 0 to 3.

2. The compound according to claim 1, wherein The compound represented by the chemical formula 1 is any one selected from the compounds represented by the following chemical formulas 2 to 5: Chemical formula 2 Chemical formula 3 Chemical formula 4 Chemical formula 5 In the chemical formulae 2 to 5, X1, X2, X3, Y, L1, L2, Ar1, Ar2, R1, R2, m and n are the same as defined in claim 1.

3. The compound according to claim 1, wherein m and n are each independently 0 or 1.

4. The compound according to claim 1, wherein The compound represented by the 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 contain the compound according to any one of claims 1 to 4.

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