Novel compound and organic light-emitting device comprising same

Abstract

The present disclosure relates to a novel compound and an organic light emitting device comprising the same.

Description

Technical Field

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of priority of Korean Patent Application No. 10-2023-0035467 filed in the Korean Intellectual Property Office on March 17, 2023, and Korean Patent Application No. 10-2024-0032010 filed in the Korean Intellectual Property Office on March 6, 2024, the disclosures of which are incorporated herein by reference in their entirety.

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

[0004] Generally, the organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic materials. Organic light emitting devices using the organic light emitting phenomenon have characteristics such as wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed, and therefore many studies have been conducted on them.

[0005] An organic light-emitting device generally has a structure including an anode, a cathode, and an organic material layer between the anode and the cathode. The organic material layer generally has a multilayer structure including different materials to improve the efficiency and stability of the organic light-emitting device. For example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of the organic light-emitting device, if a voltage is applied between two electrodes, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode into the organic material layer, and when the injected holes and electrons meet each other, excitons are formed, and light is emitted when the excitons fall to the ground state again.

[0006] There is a continuing need to develop new materials for organic materials used in organic light emitting devices as described above.

[0007] [Prior art literature]

[0008] [Patent Document]

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

[0010] Technical issues

[0011] An object of the present disclosure is to provide a new organic light-emitting material and an organic light-emitting device comprising the same.

[0012] Technical Solution

[0013] Provided herein is a compound represented by the following Chemical Formula 1:

[0014] [Chemical formula 1]

[0015]

[0016] Wherein, in Chemical Formula 1,

[0017] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 Heteroaryl,

[0018] R1 to R8 are each independently hydrogen; deuterium; or substituted or unsubstituted C 6-60 Aryl, provided that at least one of R1 to R8 is deuterium, and

[0019] Ra to Rd are each independently hydrogen; deuterium; or unsubstituted or deuterium-substituted C 6-60 Aryl.

[0020] Also provided herein is an organic light emitting device comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises the compound represented by Chemical Formula 1.

[0021] Beneficial Effects

[0022] The compound represented by Chemical Formula 1 can be used as a material of an organic material layer of an organic light-emitting device, and can improve efficiency, achieve low driving voltage and / or improve life characteristics in the organic light-emitting device. In particular, the compound represented by Chemical Formula 1 can be used as a hole injection material, a hole transport material, a light-emitting material, an electron transport material and / or an electron injection material. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 An example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4 is shown.

[0024] Figure 2 An example of an organic light-emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10 and a cathode 4 is shown. DETAILED DESCRIPTION

[0025] Hereinafter, embodiments of the present disclosure will be described to help understand the disclosed subject matter.

[0026] The present disclosure provides a compound represented by Chemical Formula 1.

[0027] In this disclosure, the symbol It refers to the bond to another substituent.

[0028] In the present disclosure, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the following: deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkylthio group; arylthio group; alkylsulfonyl group; arylsulfonyl group; silyl group; boron 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; and heteroaryl group containing at least one of N, O and S atoms, or unsubstituted or substituted with substituents in which two or more substituents are connected among the substituents exemplified above. For example, "substituents in which two or more substituents are connected" can be biphenyl. That is, the biphenyl group can be an aryl group, or it can be interpreted as a substituent formed by connecting two phenyl groups. In one example, the term "substituted or unsubstituted" can be understood to mean "unsubstituted or substituted with a moiety selected from deuterium, halogen, C 1-10 Alkyl, C 1-10 Alkoxy, C 6-20 One or more substituents in the aryl group, and a C 2-20 In addition, the term “substituted with one or more substituents” as used herein may be understood to mean “substituted with 1 to 5 substituents”, or “substituted with one or two substituents”.

[0029] In the present disclosure, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, it may be a substituent having the following structure, but is not limited thereto.

[0030]

[0031] In the present disclosure, the ester group may have a structure in which 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 substituent having the following structural formula, but is not limited thereto.

[0032]

[0033] In the present disclosure, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25.

[0034] Specifically, the imide group may be a substituent having the following structural formula, but is not limited thereto.

[0035]

[0036] In the present disclosure, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but are not limited thereto.

[0037] In the present disclosure, the boryl group specifically includes a trimethylboryl group, a triethylboryl group, a tert-butyldimethylboryl group, a triphenylboryl group, and a phenylboryl group, but is not limited thereto.

[0038] In the present disclosure, examples of halogen groups include fluorine, chlorine, bromine or iodine.

[0039] In the present disclosure, the alkyl group may be linear or branched, and its carbon number is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number of 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, 5-methylhexyl and the like, but are not limited thereto.

[0040] In the present disclosure, the alkenyl group may be linear or branched, and the carbon number thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another embodiment, the carbon number of the alkenyl group is 2 to 10. According to yet another embodiment, the carbon number of the alkenyl group is 2 to 6. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0041] In the present disclosure, the cycloalkyl group is not particularly limited, but its carbon number is preferably 3 to 60. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specific examples thereof include 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 and the like, but are not limited thereto.

[0042] In the present disclosure, the aryl group is not particularly limited, but its carbon number is preferably 6 to 60, and it 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. As a monocyclic aryl group, the aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. Polycyclic aryl groups include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, etc., but not limited thereto.

[0043] In the present disclosure, the fluorenyl group may be substituted, and two substituents may be connected to each other to form a spirocyclic structure. In the case where the fluorenyl group is substituted, Etc. However, the structure is not limited thereto.

[0044] In the present disclosure, the heteroaryl group is a heteroaryl group containing one or more of O, N, Si and S as a heteroatom, and the carbon number thereof is not particularly limited, but is preferably 2 to 60. According to one embodiment, the carbon number of the heteroaryl group is 6 to 30. According to one embodiment, the carbon number of the heteroaryl group is 6 to 20. Examples of the heteroaryl 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, dibenzofuranyl and the like, but are not limited thereto.

[0045] In the present disclosure, the aryl in aralkyl, aralkenyl, alkylaryl and arylamine is the same as the example of aryl as defined above. In the present disclosure, the alkyl in aralkyl, alkylaryl and alkylamine is the same as the example of alkyl as defined above. In the present disclosure, the heteroaryl in heteroarylamine can apply the description of heteroaryl as defined above. In the present disclosure, the alkenyl in aralkenyl is the same as the example of alkenyl as defined above. In the present disclosure, the description of aryl as defined above can be applied, except that arylene is a divalent group. In the present disclosure, the description of heteroaryl as defined above can be applied, except that heteroarylene is a divalent group. In the present disclosure, the description of aryl or cycloalkyl as defined above can be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the present disclosure, the description of heteroaryl as defined above can be applied, except that heteroaryl is not a monovalent group but is formed by combining two substituents.

[0046] Preferably, Ar1 and Ar2 may each independently be a substituted or unsubstituted C 6-20 aryl; or a substituted or unsubstituted C 2-20 Heteroaryl,

[0047] More preferably, Ar1 and Ar2 may each independently be phenyl, biphenyl, dibenzofuranyl or dibenzothiophenyl, wherein Ar1 and Ar2 may each independently be unsubstituted or substituted with at least one deuterium.

[0048] Preferably, at least one of Ar1 and Ar2 may be a phenyl group which is unsubstituted or substituted with at least one deuterium group.

[0049] R1 to R8 are each independently hydrogen; deuterium; or substituted or unsubstituted C 6-20 Aryl, provided that at least one of R1 to R8 may be deuterated.

[0050] More preferably, R1 to R8 may each independently be hydrogen, deuterium, or phenyl substituted with five deuteriums, provided that at least one of R1 to R8 may be deuterium.

[0051] More preferably, R1 to R8 may each independently be deuterium or a phenyl group substituted with five deuteriums, provided that at least one of R1 to R8 may be deuterium.

[0052] Preferably, four or more of R1 to R8 may be deuterium. More preferably, six or more of R1 to R8 may be deuterium. Most preferably, seven or more of R1 to R8 may be deuterium.

[0053] Preferably, Ra to Rd can each independently be hydrogen; deuterium; or unsubstituted or deuterium-substituted C 6-20 Aryl.

[0054] More preferably, Ra to Rd may each independently be hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl or triphenylene, wherein phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl or triphenylene may each independently be unsubstituted or substituted with at least one deuterium.

[0055] More preferably, Ra to Rd may each independently be hydrogen, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl or triphenylene, wherein phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl or triphenylene may each independently be unsubstituted or substituted with at least one deuterium.

[0056] More preferably, any one of Ra to Rd may be phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl or triphenylene, wherein phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl and triphenylene may each independently be unsubstituted or substituted with at least one deuterium, and the remainder may be hydrogen.

[0057] Most preferably, any one of Ra to Rd may be any one selected from the following, and the remainder may be hydrogen:

[0058]

[0059] Representative examples of the compound represented by Chemical Formula 1 are as follows:

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] The compound represented by Chemical Formula 1 can be prepared by a preparation method as shown in the following Reaction Scheme 1 as an example, and other remaining compounds can also be prepared in a similar manner.

[0089] [Reaction Scheme 1]

[0090]

[0091] In Reaction Scheme 1, R1 to R8, Ra to Rd, Ar1 and Ar2 are as defined in Chemical Formula 1, and X is a halogen, preferably X is chlorine or bromine.

[0092] Reaction Scheme 1 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used for the amine substitution reaction can be modified as known in the art. The preparation method can be further presented in the preparation examples described below.

[0093] In addition, according to the present disclosure, there is provided an organic light-emitting device including a compound represented by Chemical Formula 1. In one example, the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.

[0094] The organic material layer of the organic light-emitting device of the present disclosure may have a single-layer structure, or it may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present disclosure may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic layers.

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

[0096] In addition, the organic material layer may include a hole transport layer, a hole injection layer, or a layer that simultaneously performs hole transport and hole injection, wherein the hole transport layer, the hole injection layer, or the layer that simultaneously performs hole transport and hole injection may contain the compound represented by Chemical Formula 1.

[0097] In addition, the organic material layer may include an electron transport layer, an electron injection layer, or an electron injection and transport layer, wherein the electron transport layer, the electron injection layer, or the electron injection and transport layer may include the compound represented by Chemical Formula 1.

[0098] In addition, the organic light-emitting device according to the present disclosure may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present disclosure may be an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, Figure 1 and Figure 2 The structure of an organic light emitting device according to an embodiment of the present disclosure is shown.

[0099] Figure 1 An example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4 is shown. Figure 2An example of an organic light-emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10 and a cathode 4 is shown.

[0100] In such a structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer.

[0101] The organic light emitting device according to the present disclosure can be manufactured by materials and methods known in the art, except that at least one of the organic material layers contains the compound represented by Chemical Formula 1. In addition, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0102] For example, an organic light-emitting device according to the present disclosure can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting device can be manufactured by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method to form an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the anode, and then depositing a material that can be used as a cathode on the organic material layer. In addition to such a method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0103] In addition, when manufacturing an organic light-emitting device, the compound represented by Chemical Formula 1 can be formed into an organic material layer by a solution coating method and a vacuum deposition method. The solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0104] In addition to such a method, an organic light emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Publication WO2003 / 012890). However, the manufacturing method is not limited thereto.

[0105] In one example, the first electrode is an anode and the second electrode is a cathode, or alternatively, the first electrode is a cathode and the second electrode is an anode.

[0106] As the anode material, it is generally preferred to use a material with a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of anode materials include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; 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; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; etc., but are not limited thereto.

[0107] As the cathode material, it is generally preferred to use a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; etc., but are not limited thereto.

[0108] The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably such a compound: it has the ability to transport holes, so it has the effect of injecting holes in the anode and the excellent hole injection effect on the light-emitting layer or the light-emitting material, preventing the excitons generated in the light-emitting layer from moving to the hole injection layer or the electron injection material, and is also excellent in the ability to form a thin film. It is preferred that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, polyaniline and polythiophene conductive polymers, but are not limited to this.

[0109] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport material is suitably a material having a large hole mobility, which can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers having both conjugated and non-conjugated parts, etc., but are not limited thereto.

[0110] The electron blocking layer means a layer disposed between the hole transport layer and the light emitting layer to prevent the electrons injected in the cathode from transferring to the hole transport layer without recombining in the light emitting layer, which may also be referred to as an electron suppression layer or an electron blocking layer. The electron blocking layer is preferably a material having a smaller electron affinity than the electron transport layer.

[0111] The light-emitting material is preferably a material that can receive holes and electrons respectively transmitted from the hole transport layer and the electron transport layer, and combine the holes and electrons to emit light in the visible light region, and has good quantum efficiency for fluorescence or phosphorescence. Specific examples of the light-emitting material include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; diphenylethylene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo-based azoles, benzothiazole-based and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorenes; rubrene; and the like, but are not limited thereto.

[0112] The light-emitting layer may include a host material and a dopant material. The host material includes fused aromatic ring derivatives, heterocyclic compounds, and the like. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like. Examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

[0113] Examples of dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is a substituted or unsubstituted fused aromatic ring derivative having an arylamino group, and examples thereof include pyrene, anthracene, Diindenopyrene, etc. The styrylamine compound is a compound in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, wherein one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino are substituted or unsubstituted. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but are not limited thereto. In addition, the metal complex includes iridium complex, platinum complex, etc., but are not limited thereto.

[0114] The hole blocking layer is a layer disposed between the electron transport layer and the light emitting layer to prevent holes injected in the anode from being transferred to the electron transport layer without being recombined in the light emitting layer. The hole blocking layer is preferably a material with large ionization energy.

[0115] The electron transport layer is a layer that can receive electrons from the electron injection layer and transfer the electrons to the light-emitting layer, and the electron transport material is suitably a material that can well receive electron injection from the cathode and transfer the electrons to the light-emitting layer, and has a large electron mobility. Specific examples of electron transport materials include: Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to conventional techniques. In particular, suitable examples of cathode materials are typical materials with low work functions, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

[0116] The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound that has the ability to transport electrons, has an effect of injecting electrons from the cathode and an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents the excitons generated by the light-emitting layer from moving to the hole injection layer, and is also excellent in the ability to form a thin film. Specific examples of the electron injection layer include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, etc., and derivatives thereof; metal complex compounds; nitrogen-containing 5-membered ring derivatives; etc., but not limited thereto.

[0117] Examples of metal complex compounds include 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, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0118] Meanwhile, in the present disclosure, an “electron injection and transport layer” is a layer that functions as both an electron injection layer and an electron transport layer, and materials that function as each layer may be used alone or stacked and used in combination, but are not limited thereto.

[0119] The organic light emitting device according to the present disclosure may be a bottom emission type device, a top emission type device, or a double-sided emission type device, and in particular, it may be a bottom emission type light emitting device requiring relatively high light emission efficiency.

[0120] Furthermore, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

[0121] Hereinafter, the embodiments are described in more detail to help understand the present disclosure. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present disclosure.

[0122] [Preparation Example]

[0123] Preparation Example A: Preparation of Compound A1

[0124]

[0125] Preparation of compound A1-1

[0126] Under nitrogen atmosphere, (5-chloro-2-fluorophenyl)boric acid (40g, 229.4mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (61.4g, 229.4mmol) are added to 400ml tetrahydrofuran, and the mixture is stirred and refluxed. Then, potassium carbonate (95.1g, 688.2mmol) is dissolved in 95ml water, added thereto, stirred thoroughly, and then [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (3.4g, 4.6mmol) is added. After reacting for 11 hours, the reaction mixture is cooled to room temperature, the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is added again to 830mL toluene and dissolved, washed twice with water, and the organic layer is separated. Anhydrous magnesium sulfate is added thereto, stirred, filtered, and the filtrate is distilled under reduced pressure. The concentrated compound was purified by silica gel column using toluene and ethyl acetate to prepare compound A1-1 (58.9 g, 71%, MS: [M+H]+=362.8) as a gray solid.

[0127] 2) Preparation of Compound A1

[0128] A1-1 (50g, 138.2mmol) and bis(pinacol) diboron (38.7g, 165.8mmol) were added to 750ml of Diox under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium acetate (39.9g, 414.6mmol) was added thereto, stirred thoroughly, and then palladium dibenzylideneacetone palladium (2.4g, 4.1mmol) and tricyclohexylphosphine (2.3g, 8.3mmol) were added. After reacting for 5 hours, the reaction mixture was cooled to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. It was added again to 626mL toluene and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound A1 (53.3g, 85%, MS: [M+H] + = 454.3) as a yellow solid.

[0129] Preparation Example B: Preparation of Compound B1

[0130]

[0131] Compound B1 (35.3 g, 73%, MS: [M+H]+=530.4) was prepared in the same manner as in the preparation method of compound A1, except that in Preparation Example A, 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0132] Preparation Example C: Preparation of Compound C1

[0133]

[0134] 1) Preparation of Compound C1-1

[0135] Under nitrogen atmosphere, (4-chloro-2-fluorophenyl)boric acid (40g, 229.4mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (61.4g, 229.4mmol) are added to 400ml tetrahydrofuran, and the mixture is stirred and refluxed. Then, potassium carbonate (95.1g, 688.2mmol) is dissolved in 95ml water, added thereto, stirred thoroughly, and then [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (3.4g, 4.6mmol) is added. After reacting for 6 hours, the reaction mixture is cooled to room temperature, the organic layer and the water layer are separated, and the organic layer is then distilled. It is added again to 830mL toluene and dissolved, washed twice with water, and the organic layer is separated. Anhydrous magnesium sulfate is added thereto, stirred, filtered, and the filtrate is distilled under reduced pressure. The concentrated compound was purified by silica gel column using toluene and ethyl acetate to prepare compound C1-1 (66.4 g, 80%, MS: [M+H]+=362.8) as a gray solid.

[0136] 2) Preparation of Compound C1

[0137] Under nitrogen atmosphere, C1-1 (40g, 110.6mmol) and bis (pinacol) diboron (30.9g, 132.7mmol) are added to 600ml of Diox, and the mixture is stirred and refluxed. Then, potassium acetate (31.9g, 331.7mmol) is added thereto, fully stirred, then palladium dibenzylideneacetone palladium (1.9g, 3.3mmol) and tricyclohexylphosphine (1.9g, 6.6mmol) are added. After reacting for 6 hours, the reaction mixture is cooled to room temperature, the organic layer is filtered to remove salt, and the filtered organic layer is then distilled. It is added again to 501mL chloroform and dissolved, washed twice with water, and the organic layer is separated. Anhydrous magnesium sulfate is added thereto, stirred, filtered, and the filtrate is distilled under reduced pressure. The concentrated compound was purified by silica gel column using chloroform and ethyl acetate to prepare Compound C1 (31.6 g, 63%, MS: [M+H]+=454.3) as a gray solid.

[0138] Preparation Example D: Preparation of Compound D1

[0139]

[0140] Compound D1 (30.5 g, 70%, MS: [M+H]+=461.2) was prepared in the same manner as in the preparation method of compound A1, except that in Preparation Example A, 2-chloro-4,6-bis(phenyl-2,3,4,5-d4)-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0141] Preparation Example E: Preparation of Compound E1

[0142]

[0143] Compound E1 (35.8 g, 77%, MS: [M+H]+=529) was prepared in the same manner as in the preparation method of compound A1, except that in Preparation Example A, 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0144] Preparation Example 1: Preparation of Compound 1

[0145]

[0146] Step 1) Preparation of compound Sub 1

[0147] A1 (36g, 79.4mmol) and 3-bromo-1,1'-biphenyl (18.5g, 79.4mmol) were added to 720ml tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (32.9g, 238.2mmol) was then dissolved in 33ml water, added thereto, stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium (0.8g, 1.6mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature and the resulting solid was filtered. The solid was added to 1904mL chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound Sub 1 (28.9g, 76%, MS: [M+H] + = 480.6) as a gray solid.

[0148] Step 2) Preparation of Compound 1

[0149] Compound Sub 1 (40 g, 83.4 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (14.5 g, 83.4 mmol) were added to 320 ml of dimethylacetamide under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, tripotassium phosphate (53.1 g, 250.2 mmol) was added thereto, stirred thoroughly, and then reacted for 1 hour. The reaction mixture was cooled to room temperature, the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was added again to 1583 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound 1 (30.1 g, 57%, MS: [M+H] + = 633.8) as a yellow solid.

[0150] Preparation Example 2: Preparation of Compound 2

[0151]

[0152] Step 1) Preparation of compound Sub 2

[0153] Compound A1 (36g, 79.4mmol) and 4-iodo-1,1'-biphenyl (22.2g, 79.4mmol) were added to 720ml tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (32.9g, 238.2mmol) was then dissolved in 33ml water, added thereto, stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium (0.8g, 1.6mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature and the resulting solid was filtered. The solid was added to 1904mL chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound Sub 2 (34.7g, 91%, MS: [M+H] + = 480.6) as a red solid.

[0154] Step 2) Preparation of Compound 2

[0155] Compound Sub 2 (40 g, 83.4 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (14.5 g, 83.4 mmol) were added to 320 ml of dimethylacetamide under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, tripotassium phosphate (53.1 g, 250.2 mmol) was added thereto, stirred thoroughly, and then reacted for 1 hour. The reaction mixture was cooled to room temperature, the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was added again to 1583 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound 2 (41.7 g, 79%, MS: [M+H] + = 633.8) as a yellow solid.

[0156] Preparation Example 3: Preparation of Compound 3

[0157]

[0158] Step 1) Preparation of compound Sub 3

[0159] Compound A1 (36 g, 79.4 mmol) and 5'-bromo-1,1':3',1"-terphenyl (24.6 g, 79.4 mmol) were added to 720 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (32.9 g, 238.2 mmol) was dissolved in 33 ml of water, added thereto, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium (0.8 g, 1.6 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the obtained solid was filtered. The solid was added to 2206 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare Compound Sub 3 (27.4 g, 62%, MS: [M+H]+=556.7) as a gray solid.

[0160] Step 2) Preparation of compound 3

[0161] Compound Sub 3 (40 g, 72 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (12.5 g, 72 mmol) were added to 320 ml of dimethylacetamide under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, tripotassium phosphate (45.8 g, 216 mmol) was added thereto, stirred thoroughly, and then reacted for 2 hours. The reaction mixture was cooled to room temperature, the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was added again to 1531 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound 3 (40.8 g, 80%, MS: [M+H] + = 709.9) as a yellow solid.

[0162] Preparation Example 4: Preparation of Compound 4

[0163]

[0164] Step 1) Preparation of compound Sub 4

[0165] Compound A1 (30 g, 66.2 mmol) and bromobenzene (10.4 g, 66.2 mmol) were added to 300 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (27.4 g, 198.5 mmol) was then dissolved in 27 ml of water, added thereto, stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium (0.7 g, 1.3 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature and the resulting solid was filtered. The solid was added to 1335 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound Sub 4 (19.5 g, 73%, MS: [M+H] + = 404.5) as a gray solid.

[0166] Step 2) Preparation of Compound 4

[0167] Compound Sub 4 (30 g, 74.4 mmol) and 3-(phenyl-2,4,6-d3)-9H-carbazole-1,2,4,5,6,8-d6 (18.8 g, 74.4 mmol) were added to 240 ml of methylacetamide under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium phosphate (47.4 g, 223.1 mmol) was added thereto, stirred thoroughly, and then reacted for 1 hour. The reaction mixture was cooled to room temperature, the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was added again to 1418 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound 4 (32.1 g, 68%, MS: [M+H] + = 636.8) as a yellow solid.

[0168] Preparation Example 5: Preparation of Compound 5

[0169]

[0170] Step 1) Preparation of compound Sub 5

[0171] Compound B1 (30 g, 56.7 mmol) and bromobenzene (8.9 g, 56.7 mmol) were added to 450 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.5 g, 170 mmol) was then dissolved in 23 ml of water, added thereto, stirred thoroughly, and then [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.8 g, 1.1 mmol) was added. After reacting for 12 hours, the reaction mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was added again to 272 mL of toluene and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using toluene and ethyl acetate to prepare compound Sub 5 (16.6 g, 61%, MS: [M+H] + = 480.6) as a gray solid.

[0172] Step 2) Preparation of Compound 5

[0173] Compound Sub 5 (30 g, 62.6 mmol) and 9H-carbazole-d8 (11 g, 62.6 mmol) were added to 240 ml of dimethylacetamide under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, tripotassium phosphate (39.8 g, 187.7 mmol) was added thereto, stirred thoroughly, and then reacted for 1 hour. The reaction mixture was cooled to room temperature, the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was added again to 1191 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound 5 (20.7 g, 52%, MS: [M+H] + = 635.8) as a yellow solid.

[0174] Preparation Example 6: Preparation of Compound 6

[0175]

[0176] Step 1) Preparation of compound Sub 6

[0177] Compound C1 (35g, 77.2mmol) and 4-iodo-1,1'-biphenyl (21.6g, 77.2mmol) were added to 350ml tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (32g, 231.6mmol) was then dissolved in 32ml water, added thereto, stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium (0.8g, 1.5mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature and the resulting solid was filtered. The solid was added to 1851mL chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound Sub 6 (29.3g, 79%, MS: [M+H] + = 480.6) as a gray solid.

[0178] Step 2) Preparation of Compound 6

[0179] Compound Sub 6 (25 g, 52.1 mmol) and 9H-carbazole-d8 (9.1 g, 52.1 mmol) were added to 200 ml of dimethylacetamide under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, tripotassium phosphate (33.2 g, 156.4 mmol) was added thereto, stirred thoroughly, and then reacted for 2 hours. The reaction mixture was cooled to room temperature, the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was added again to 993 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound 6 (17.5 g, 53%, MS: [M+H] + = 635.8) as a yellow solid.

[0180] Preparation Example 7: Preparation of Compound 7

[0181]

[0182] Compound 7 (29.5 g, 66%, MS: [M+H]+=715.9) was prepared in the same manner as in the preparation method of compound 6, except that in Preparation Example 6, 3-(phenyl-d5)-9H-carbazole-1,2,4,5,6,7,8-d7 was used instead of 9H-carbazole-d8.

[0183] Preparation Example 8: Preparation of Compound 8

[0184]

[0185] Step 1) Preparation of Compound F1

[0186] Compound F1 (39.4 g, 75%, MS: [M+H]+=544.4) was prepared in the same manner as in the preparation method of compound A1, except that in Preparation Example 1, 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0187] Step 2) Preparation of compound Sub 7

[0188] Compound F1 (35 g, 64.4 mmol) and 3-bromo-1,1'-biphenyl (15 g, 64.4 mmol) were added to 350 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (26.7 g, 193.2 mmol) was then dissolved in 27 ml of water, added thereto, stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium (0.7 g, 1.3 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature and the resulting solid was filtered. The solid was added to 1834 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound Sub 7 (22.4 g, 61%, MS: [M+H] + = 570.6) as a gray solid.

[0189] Step 3) Preparation of Compound 8

[0190] Compound Sub 7 (30 g, 52.7 mmol) and 9H-carbazole-d8 (9.2 g, 52.7 mmol) were added to 240 ml of dimethylacetamide under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, tripotassium phosphate (33.5 g, 158 mmol) was added thereto, stirred thoroughly, and then reacted for 3 hours. The reaction mixture was cooled to room temperature, the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was added again to 1142 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound 8 (25.5 g, 67%, MS: [M+H] + = 723.9) as a yellow solid.

[0191] Preparation Example 9: Preparation of Compound 9

[0192]

[0193] Compound 9 (34.1 g, 69%, MS: [M+H]+=806) was prepared in the same manner as in the preparation method of compound 8, except that in Preparation Example 8, 3-(phenyl-d5)-9H-carbazole-1,2,4,5,6,7,8-d7 was used instead of 9H-carbazole-d8.

[0194] Preparation Example 10: Preparation of Compound 10

[0195]

[0196] Step 1) Preparation of Compound G1

[0197] Compound G1 (26.6 g, 52%, MS: [M+H]+=560.5) was prepared in the same manner as in the preparation method of compound A1, except that in Preparation Example 1, 2-chloro-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0198] Step 2) Preparation of compound Sub 8

[0199] Compound Sub 8 (26.4 g, 72%, MS: [M+H]+=586.7) was prepared in the same manner as in the preparation method of Compound Sub 7, except that in Preparation Example 8, Compound G1 was used instead of Compound F1.

[0200] Step 3) Preparation of compound 10

[0201] Compound Sub 8 (25 g, 42.7 mmol) and 9H-carbazole-d8 (7.5 g, 42.7 mmol) were added to 200 ml of dimethylacetamide under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, tripotassium phosphate (27.2 g, 128.1 mmol) was added thereto, stirred thoroughly, and then reacted for 2 hours. The reaction mixture was cooled to room temperature, the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was added again to 949 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound 10 (25.3 g, 80%, MS: [M+H] + = 742) as a yellow solid.

[0202] Preparation Example 11: Preparation of Compound 11

[0203]

[0204] Compound 11 (21.5 g, 70%, MS: [M+H]+=634) was prepared in the same manner as in the preparation method of Compound 2, except that in Preparation Example 2, 9H-carbazole-d8 was used instead of 9H-carbazole-d6.

[0205] Preparation Example 12: Preparation of Compound 12

[0206]

[0207] Step 1) Preparation of compound Sub 9

[0208] Compound D1 (35g, 75.9mmol) and 4-iodo-1,1'-biphenyl (21.2g, 75.9mmol) were added to 350ml tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (31.5g, 227.6mmol) was then dissolved in 31ml water, added thereto, stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium (0.8g, 1.5mmol) was added. After reacting for 5 hours, the reaction mixture was cooled to room temperature and the resulting solid was filtered. The solid was added to 1850mL chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound Sub 9 (27g, 73%, MS: [M+H] + = 488) as a gray solid.

[0209] Step 2) Preparation of compound 12

[0210] Compound Sub 9 (25 g, 51.3 mmol) and 9H-carbazole-1,2,3,4,5,6,8-d7 (8.9 g, 51.3 mmol) were added to 200 ml of dimethylacetamide under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, tripotassium phosphate (32.6 g, 153.8 mmol) was added thereto, stirred thoroughly, and then reacted for 1 hour. The reaction mixture was cooled to room temperature, the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was added again to 987 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound 12 (17.4 g, 53%, MS: [M+H] + = 642) as a yellow solid.

[0211] Preparation Example 13: Preparation of Compound 13

[0212]

[0213] Step 1) Preparation of compound Sub 10

[0214] Compound D1 (35g, 75.9mmol) and 3-bromo-1,1'-biphenyl (17.7g, 75.9mmol) were added to 350ml tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (31.5g, 227.6mmol) was then dissolved in 31ml water, added thereto, stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium (0.8g, 1.5mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature and the resulting solid was filtered. The solid was added to 1850mL chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound Sub 10 (29.2g, 79%, MS: [M+H] + = 488.6) as a gray solid.

[0215] Step 2) Preparation of compound 13

[0216] Compound Sub 10 (25 g, 51.3 mmol) and 4-(phenyl-d5)-9H-carbazole-1,5,6,8-d4 (12.9 g, 51.3 mmol) were added to 200 ml of dimethylacetamide under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, tripotassium phosphate (32.6 g, 153.8 mmol) was added thereto, stirred thoroughly, and then reacted for 2 hours. The reaction mixture was cooled to room temperature, the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was added again to 1093 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound 13 (23.7 g, 65%, MS: [M+H] + = 720) as a yellow solid.

[0217] Preparation Example 14: Preparation of Compound 14

[0218]

[0219] Step 1) Preparation of compound Sub 11

[0220] Compound E1 (35g, 66.1mmol) and bromobenzene (10.4g, 66.1mmol) were added to 350ml tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (27.4g, 198.3mmol) was then dissolved in 27ml water, added thereto, stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium (0.7g, 1.3mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature and the resulting solid was filtered. The solid was added to 1585mL chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound Sub 11 (25.4g, 80%, MS: [M+H] + = 480.6) as a gray solid.

[0221] Step 2) Preparation of compound 14

[0222] Compound Sub 11 (25 g, 52.1 mmol) and 4-(phenyl-d5)-9H-carbazole-2,5,6,8-d4 (13.2 g, 52.1 mmol) were added to 200 ml of dimethylacetamide under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, tripotassium phosphate (33.2 g, 156.4 mmol) was added thereto, stirred thoroughly, and then reacted for 3 hours. The reaction mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. It was added again to 1099 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare compound 14 (23.1 g, 63%, MS: [M+H] + = 712) as a yellow solid.

[0223] Example

[0224] Example 1: Fabrication of an organic light-emitting device

[0225] It is coated with a thickness of The glass substrate with ITO (indium tin oxide) as film is put into the distilled water in which detergent is dissolved, and ultrasonic cleaning is carried out. The product manufactured by Fischer Co. is used as detergent, and the distilled water filtered twice by the filter manufactured by Millipore Co. is used as distilled water. After ITO is cleaned for 30 minutes, ultrasonic cleaning is repeated twice with distilled water for 10 minutes. After cleaning with distilled water, the substrate is ultrasonically cleaned with isopropyl alcohol, acetone and methanol solvent, dried, and then transferred to a plasma cleaner. In addition, the substrate is cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum deposition machine.

[0226] On the thus prepared ITO transparent electrode, the following compound HT-A and the following compound PD were thermally vacuum deposited at a weight ratio of 95:5. Then only the following compound HT-A is deposited to The following compound HT-B was thermally vacuum deposited on the hole transport layer to form a hole transport layer. The previously prepared compound 1 and the following compounds GD were vacuum deposited on the electron blocking layer at a weight ratio of 85:15. The following compounds ET-A to ET-B were vacuum deposited on the luminescent layer. The following compound ET-B and the following compound Liq were thermally vacuum deposited on the hole blocking layer at a weight ratio of 2:1 to form a hole blocking layer. Then, Lif and Mg were vacuum deposited at a weight ratio of 1:1. Magnesium and silver were deposited on the electron injection layer in a weight ratio of 1:4. A cathode is formed by coating a film of a thickness of , thereby completing the manufacture of an organic light-emitting device.

[0227]

[0228] During the above process, the vapor deposition rate of the organic material is maintained at / second to / sec, maintaining the deposition rate of magnesium and silver at / sec, and the vacuum degree during deposition was maintained at 2*10 -7 Up to 5*10 -6 Support, thereby manufacturing an organic light-emitting device.

[0229] Examples 2 to 12 and Comparative Examples 1 to 9

[0230] Organic light-emitting devices of Examples 2 to 12 and Comparative Examples 1 to 9 were manufactured in the same manner as in Example 1, except that the host material was changed as shown in Table 1 below. In Table 1, compounds GH-A, GH-B, GH-C, GH-D, GH-E, GH-F, GH-G, GH-H, and GH-I are each as follows. 14 This means that 14 hydrogens in the compound given in brackets are replaced by deuterium.

[0231]

[0232] [Experimental example]

[0233] The voltage, efficiency and lifespan (T95) were measured by applying current to the organic light emitting devices manufactured in the examples and comparative examples, and the results are shown in the following Table 1. At this time, the voltage and efficiency were measured by applying 10 mA / cm 2 In addition, T95 shown in Table 1 means the current density at 20 mA / cm 2 The time required for the brightness to decrease to 95% of the initial brightness at a current density of .

[0234] [Table 1]

[0235]

[0236] The compound represented by Chemical Formula 1 has a structure in which a polycyclic nitrogen-containing heterocyclic substituent serving as an intramolecular electron donor and a monocyclic nitrogen-containing heterocyclic ring serving as an electron acceptor are bonded to each other at an ortho position, which makes it possible to easily achieve internal charge transfer.

[0237] Furthermore, a compound in which a benzene ring serving as an electron donor within a molecule and a polycyclic nitrogen-containing heterocycle are bonded to each other at the para position has high molecular stability and facilitates the transport of both holes and electrons.

[0238] Therefore, as shown in Table 1, it can be confirmed that when the compound of Chemical Formula 1 is used as a host of an organic light emitting device, characteristics of low voltage, high efficiency, and long lifespan occur.

[0239] [Explanation of Reference Numerals]

[0240] 1: Substrate 2: Anode

[0241] 3: Light-emitting layer 4: Cathode

[0242] 5: Hole injection layer 6: Hole transport layer

[0243] 7: Electron blocking layer 8: Hole blocking layer

[0244] 9: Electron transport layer 10: Electron injection layer

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] In Chemical Formula 1, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 Heteroaryl, R1 to R8 are each independently hydrogen; deuterium; or substituted or unsubstituted C 6-60 Aryl, provided that at least one of R1 to R8 is deuterium, and Ra to Rd are each independently hydrogen; deuterium; or unsubstituted or deuterium-substituted C 6-60 Aryl.

2. The compound according to claim 1, wherein: Ar1 and Ar2 are each independently phenyl, biphenyl, dibenzofuranyl, or dibenzothiophenyl, wherein Ar1 and Ar2 are each independently unsubstituted or substituted with at least one deuterium.

3. The compound according to claim 1, wherein: At least one of Ar1 and Ar2 is a phenyl group which is unsubstituted or substituted with at least one deuterium group.

4. The compound according to claim 1, wherein: R1 to R8 are each independently hydrogen, deuterium, or phenyl substituted with five deuteriums, provided that at least one of R1 to R8 is deuterium.

5. The compound according to claim 1, wherein: Four or more of R1 to R8 are deuterium.

6. The compound according to claim 1, wherein: Ra to Rd are each independently hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl or triphenylene, wherein the phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl or triphenylene group is each independently unsubstituted or substituted with at least one deuterium.

7. The compound according to claim 1, wherein: Ra to Rd are each independently hydrogen, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl or triphenylene, wherein the phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl or triphenylene group is each independently unsubstituted or substituted with at least one deuterium.

8. The compound according to claim 1, wherein: Any one of R to Rd is phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl or triphenylene, wherein the phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl and triphenylene are each independently unsubstituted or substituted with at least one deuterium, and The remainder is hydrogen.

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

10. An organic light-emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layers comprises the compound according to any one of claims 1 to 9.

11. The organic light emitting device according to claim 10, wherein: The organic material layer is a light-emitting layer.

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