Novel compound and organic light-emitting device comprising same

Abstract

The present disclosure relates to a novel organic light-emitting material 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. 10-2023-0055421, filed with the Korean Intellectual Property Office on April 27, 2023, and Korean Patent Application No. 10-2024-0011002, filed with the Korean Intellectual Property Office on January 24, 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 in which electrical energy is converted into light energy by using an organic material. Organic light-emitting devices utilizing the organic light-emitting phenomenon have characteristics such as a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed, and thus many studies have been conducted.

[0005] An organic light-emitting device generally has a structure including an anode, a cathode, and an organic material layer interposed between the anode and the cathode. The organic material layer generally has a multilayer structure including different materials to enhance 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 an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic material layer, electrons are injected from the cathode into the organic material layer, excitons are formed when the injected holes and electrons meet each other, and light is emitted when the excitons fall back to the ground state.

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

[0007] [Prior Art Documents]

[0008] [Patent Documents]

[0009] (Patent Document 1) Korean Patent Laid-Open No. 10-2000-0051826 Summary of the Invention

[0010] Technical Problem

[0011] An object of the present disclosure is to provide novel organic light-emitting materials and organic light-emitting devices comprising the same.

[0012] Technical Solution

[0013] Compounds represented by the following Chemical Formula 1 are provided herein:

[0014] [Chemical Formula 1]

[0015]

[0016] Among them, in Chemical Formula 1,

[0017] Ar1 and Ar2 are each independently a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C containing at least one of N, O, and S 2-60 heteroaryl,

[0018] L1 and L2 are each independently a single bond; a substituted or unsubstituted C 6-60 arylene; or a substituted or unsubstituted C containing at least one of N, O, and S 2-60 heteroarylene,

[0019] Ar3 is a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C containing at least one of N, O, and S 2-60 heteroaryl,

[0020] X1 to X3 are each independently N or CR,

[0021] R is hydrogen; deuterium; a substituted or unsubstituted C 1-60 alkyl; a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C containing at least one of N, O, and S 2-60 heteroaryl,

[0022] D is deuterium,

[0023] a and c are each independently an integer from 0 to 3,

[0024] b and d are each independently an integer from 0 to 4, and

[0025] at least one of a to d is 1 or greater.

[0026] Also provided herein is an organic light-emitting device, which includes: 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 contains a compound represented by Chemical Formula 1.

[0027] Beneficial effects

[0028] The compound represented by Chemical Formula 1 as described above can be used as a material for an organic material layer in an organic light-emitting device, and can improve efficiency, achieve a low driving voltage and / or improve lifetime 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, an electron blocking material, a light-emitting material, a hole blocking material, an electron transport and / or electron injection material. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] 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.

[0030] Figure 2 An example of an organic light-emitting device including a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, an electron blocking layer 8, a light-emitting layer 3, a hole blocking layer 9, an electron injection and transport layer 10, and a cathode 4 is shown. DETAILED DESCRIPTION

[0031] Hereinafter, embodiments of the present disclosure will be described to more fully understand the disclosed subject matter.

[0032] The present disclosure provides a compound represented by Chemical Formula 1.

[0033] As used herein, the symbol or means a bond connected to another substituent.

[0034] As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the following: 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; an arylthio group; an alkylsulfonyl group; an arylsulfonyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroarylamino group; an arylamino group; an arylphosphine group; or a heteroaryl containing one or more of N, O, and S atoms, or unsubstituted or substituted with a substituent in which two or more of the above-exemplified substituents are connected. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, a biphenyl group may be an aryl group, or it may also be interpreted as a substituent in which two phenyl groups are connected. In one example, the term "substituted or unsubstituted" may be understood to mean "unsubstituted or substituted with one or more substituents (e.g., 1 to 5 substituents) selected from the following: deuterium, halogen, C 1-10 alkyl, C 1-10 alkoxy, C 6-20an aryl group, and a C containing one or more heteroatoms selected from N, O, and S 2-20 a heteroaryl group”. In addition, as used herein, the term “substituted with one or more substituents” can be understood to mean, for example, “substituted with 1 to 5 substituents” or “substituted with 1 or 2 substituents”.

[0035] In the present disclosure, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, it may be a substituent having the following structures, but is not limited thereto.

[0036]

[0037] In the present disclosure, the ester group may have a structure in which the oxygen of the ester group is substituted with a straight-chain, branched-chain, 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 formulas, but is not limited thereto.

[0038]

[0039] In the present disclosure, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group may be a substituent having the following structural formulas, but is not limited thereto.

[0040]

[0041] In the present disclosure, the silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but is not limited thereto.

[0042] In the present disclosure, the boron group specifically includes trimethylboron, triethylboron, tert-butyldimethylboron, triphenylboron, phenylboron, etc., but is not limited thereto.

[0043] In the present disclosure, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

[0044] 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 alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto.

[0045] In the present disclosure, the alkenyl group may be linear or branched, and its carbon number is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to yet another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples 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-(naphthalen-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, styryl, etc., but are not limited thereto.

[0046] In the present disclosure, the cycloalkyl group is not particularly limited, but its carbon number is preferably 3 to 60. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples 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, etc., but are not limited thereto.

[0047] In the present disclosure, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and it may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. As the monocyclic aryl group, the aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. The polycyclic aryl group includes naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, and the like, but is not limited thereto.

[0048] In the present disclosure, the fluorenyl group may be substituted, and two substituents may be connected to each other to form a spiro structure. In the case where the fluorenyl group is substituted, etc. may be formed. However, the structure is not limited thereto.

[0049] In the present disclosure, the heteroaryl group is a heteroaryl group containing one or more of O, N, Si, and S as heteroatoms, and its carbon number is not particularly limited, but preferably 2 to 60. According to one embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to another embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of the heteroaryl group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuryl, phenanthrolinyl, iso oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuryl, etc., but is not limited thereto.

[0050] In the present disclosure, the aryl group in aralkyl, aralkenyl, alkylaryl, and arylamino is the same as the examples of aryl groups defined above. In the present disclosure, the alkyl group in aralkyl, alkylaryl, and alkylamino is the same as the examples of alkyl groups defined above. In the present disclosure, the heteroaryl group in heteroarylamine can be described by applying the description of heteroaryl groups defined above. In the present disclosure, the alkenyl group in aralkenyl is the same as the examples of alkenyl groups defined above. In the present disclosure, the description of aryl groups defined above can be applied, with the difference that the arylene group is a divalent group. In the present disclosure, the description of heteroaryl groups defined above can be applied, with the difference that the heteroarylene group is a divalent group. In the present disclosure, the description of aryl or cycloalkyl groups defined above can be applied, with the difference that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the present disclosure, the description of heteroaryl groups defined above can be applied, with the difference that the heterocyclic ring is not a monovalent group but is formed by combining two substituents.

[0051] Preferably, Ar1 and Ar2 can each independently be a substituted or unsubstituted C 6-20 aryl group; or a substituted or unsubstituted C 2-20 heteroaryl group containing at least one of N, O, and S.

[0052] More preferably, Ar1 and Ar2 can each independently be a phenyl group, a biphenyl group, or a dibenzofuranyl group, wherein the phenyl group, biphenyl group, or dibenzofuranyl group can be unsubstituted or substituted with at least one deuterium.

[0053] Most preferably, Ar1 and Ar2 can each independently be a phenyl group, a phenyl group substituted with 5 deuteriums, a biphenyl group, or a dibenzofuranyl group.

[0054] Preferably, at least one of Ar1 and Ar2 can be a substituted or unsubstituted C 6-20 aryl group.

[0055] Preferably, at least one of Ar1 and Ar2 can be an unsubstituted or deuterium-substituted C 6-20 aryl group.

[0056] More preferably, at least one of Ar1 and Ar2 can be a phenyl group, or a phenyl group substituted with 5 deuteriums.

[0057] Preferably, L1 and L2 can each independently be a single bond; a substituted or unsubstituted C 6-20 arylene group; or a substituted or unsubstituted C 2-20 heteroarylene group containing at least one of N, O, and S.

[0058] More preferably, L1 and L2 can each independently be a single bond; or a substituted or unsubstituted C 6-20 arylene.

[0059] More preferably, L1 and L2 can each independently be a single bond; or a phenyl group which is unsubstituted or substituted with at least one deuterium.

[0060] Most preferably, L1 and L2 can each independently be a single bond or a phenyl group.

[0061] Preferably, at least one of L1 and L2 can be a single bond.

[0062] Preferably, Ar3 can be a substituted or unsubstituted C 6-20 aryl; or a substituted or unsubstituted C containing at least one selected from N, O and S 2-20 heteroaryl.

[0063] More preferably, Ar3 can be a substituted or unsubstituted C 6-20 aryl.

[0064] More preferably, Ar3 can be an unsubstituted or deuterium-substituted C 6-20 aryl.

[0065] More preferably, Ar3 can be a phenyl group or a biphenyl group, wherein the phenyl group or the biphenyl group can be unsubstituted or substituted with at least one deuterium.

[0066] Most preferably, Ar3 can be a phenyl group, a phenyl group substituted with 5 deuteriums, a biphenyl group, or a biphenyl group substituted with 9 deuteriums.

[0067] Preferably, at least one of X1 to X3 can be N, and the remainder can be CR.

[0068] More preferably, at least two of X1 to X3 can be N, and the remainder can be CR.

[0069] Most preferably, X1 to X3 can each be N.

[0070] Preferably, a and c can each be 3, and b and d can each be 4.

[0071] Representative examples of the compound represented by Chemical Formula 1 are as follows:

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083] 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 the remaining other compounds can also be prepared in a similar manner.

[0084] [Reaction Scheme 1]

[0085]

[0086] In Reaction Scheme 1, Ar1 to Ar3, L1, L2, X1 to X3, R, D, and a to d are as defined in Chemical Formula 1, and Z is a halogen. Preferably, Z is chlorine or bromine.

[0087] Reaction Scheme 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups used for the Suzuki coupling reaction can be changed as known in the art. The preparation method can be further presented in the Preparation Examples described below.

[0088] Furthermore, according to the present disclosure, there is provided an organic light-emitting device including the 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 layers contains the compound represented by Chemical Formula 1.

[0089] The organic material layer of the organic light-emitting device of the present disclosure can have a single-layer structure, or it can have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present disclosure can 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 the organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and it can include a smaller number of organic layers.

[0090] In addition, the organic material layer may include a light-emitting layer, and the light-emitting layer may contain a compound represented by Chemical Formula 1.

[0091] 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 shows the structure of an organic light-emitting device according to an embodiment of the present disclosure.

[0092] Figure 1 shows an example of an organic light-emitting device including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. Figure 2 shows an example of an organic light-emitting device including a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, an electron blocking layer 8, a light-emitting layer 3, a hole blocking layer 9, an electron injection and transport layer 10, and a cathode 4. In such a structure, the compound represented by Chemical Formula 1 may be included in the light-emitting layer.

[0093] The organic light-emitting device according to the present disclosure may be manufactured by materials and methods known in the art, except that the light-emitting layer contains the compound according to the present disclosure and is manufactured as described above. 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.

[0094] For example, the organic light-emitting device according to the present disclosure may 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 may be manufactured by: depositing a metal, a conductive metal oxide, or an alloy thereof on the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation 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 methods, the organic light-emitting device may also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0095] In addition, when manufacturing the organic light-emitting device, the compound represented by Chemical Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method. Among them, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying method, roll coating, etc., but is not limited thereto.

[0096] In addition to such methods, 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.

[0097] 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.

[0098] As the anode material, materials having a large work function are generally preferably used so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material 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-(ethylenedioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and the like, but are not limited thereto.

[0099] As the cathode material, materials having a small work function are generally preferably used 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; and the like, but are not limited thereto.

[0100] The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound having the ability to transport holes, and thus has an effect of injecting holes into the anode and an excellent hole injection effect on the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and is further excellent in the ability to form a thin film. Preferably, 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 the hole injection material include metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, conductive polymers based on anthraquinone, polyaniline, and polythiophene, and the like, but are not limited thereto.

[0101] 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 that can receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers in which a conjugated portion and a non-conjugated portion coexist, etc., but are not limited thereto. On the other hand, when two or more materials are used for the hole transport layer, the materials may be divided into a first hole transport layer, a second hole transport layer, etc. according to the order in which they are stacked during manufacturing.

[0102] The electron blocking layer means a layer provided between the hole transport layer and the light-emitting layer to prevent electrons injected from the cathode from being transferred to the hole transport layer and recombining in the light-emitting layer, and it 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.

[0103] The light-emitting material is preferably a material that can receive holes and electrons respectively transported from the hole transport layer and the electron transport layer, 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 tris(8-hydroxyquinoline)aluminum (Alq3); carbazole-based compounds; distyrylbenzene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds based on benzoxazole, benzothiazole, and benzimidazole; polymers based on poly(p-phenylenevinylene) (PPV); spiro compounds; polyfluorene; rubrene; and the like, but are not limited thereto.

[0104] The light-emitting layer may contain a host material and a dopant material. The host material includes fused aromatic ring derivatives, heterocyclic-containing compounds, etc. Specific examples of the fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc. Examples of the heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto. Preferably, the compound represented by Chemical Formula 1 can be used as the host material.

[0105] Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is a fused aromatic ring derivative having an arylamino group that is substituted or unsubstituted, and examples thereof include pyrene, anthracene, , indeno[1,2,3-cd]pyrene, etc. The styrylamine compound is a compound in which at least one arylvinyl group is substituted in the substituted or unsubstituted arylamine, and 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 an iridium complex, a platinum complex, etc., but is not limited thereto.

[0106] The hole blocking layer is a layer provided between the electron transport layer and the light emitting layer to prevent the holes injected from the anode from being transferred to the electron transport layer and not recombining in the light emitting layer, and it can also be referred to as a hole suppression layer. The hole blocking layer is preferably a material having a large ionization energy.

[0107] The electron transport layer is a layer that can receive electrons from the electron injection layer and transport 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, transfer the electrons to the light emitting layer, and has a large electron mobility. Specific examples of the electron transport material include: an Al complex of 8-hydroxyquinoline; a complex containing Alq3; an organic radical compound; a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer can be used together with any desired cathode material used according to conventional techniques. In particular, suitable examples of the cathode material are typical materials having a low work function followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum layer or a silver layer in each case.

[0108] 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 the effect of injecting electrons from the cathode, and has an excellent effect of injecting electrons into the light emitting layer or the light emitting material, prevents excitons generated by the light emitting layer from moving to the hole injection layer, and also has excellent ability to form a thin film. Specific examples of the electron injection layer include fluorenone, anthraquinodimethane, biphenylquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluoreneylidene methane, anthrone, etc., and their derivatives; metal complex compounds; nitrogen-containing 5-membered ring derivatives; and so on, but are not limited thereto.

[0109] Examples of metal complex compounds include, but are not limited to, lithium 8-hydroxyquinolate, zinc bis(8-hydroxyquinolate), copper bis(8-hydroxyquinolate), manganese bis(8-hydroxyquinolate), aluminum tris(8-hydroxyquinolate), aluminum tris(2-methyl-8-hydroxyquinolate), gallium tris(8-hydroxyquinolate), beryllium bis(10-hydroxybenzo[h]quinolate), zinc bis(10-hydroxybenzo[h]quinolate), chloro-gallium bis(2-methyl-8-quinolate), gallium bis(2-methyl-8-quinolate)(o-cresol), aluminum bis(2-methyl-8-quinolate)(1-naphthol), gallium bis(2-methyl-8-quinolate)(2-naphthol), etc.

[0110] On the other hand, in the present disclosure, the "electron injection and transport layer" is a layer that functions as both an electron injection layer and an electron transport layer, and the materials that function as each layer can be used alone or stacked and combined, but are not limited thereto.

[0111] The organic light-emitting device according to the present disclosure can be a bottom-emission device, a top-emission device, or a double-sided emission device. In particular, it can be a bottom-emission light-emitting device that requires relatively high luminous efficiency.

[0112] In addition, in addition to the organic light-emitting device, the compound represented by Chemical Formula 1 can also be included in an organic solar cell or an organic transistor.

[0113] Hereinafter, the embodiments will be 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.

[0114] [Preparation Example]

[0115] Preparation Example 1: Preparation of Compound GH1

[0116] (Preparation Example 1-1: Preparation of Compound GH1-a)

[0117]

[0118] Under a nitrogen atmosphere, 4-bromo-9-phenyl-9H-carbazole (30 g, 93.1 mmol) and 4-chloro-9H-carbazole (18.8 g, 93.1 mmol) were added to 450 ml of xylene, and the mixture was stirred and refluxed. Then, sodium tert-butoxide (26.8 g, 279.3 mmol) was added thereto, the mixture was stirred well, and then bis(tri-tert-butylphosphine)palladium (1.4 g, 2.8 mmol) 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 825 ml of chloroform, dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a white solid compound GH1-a (31.3 g, 76%, MS: [M+H] + = 444).

[0119] (Preparation Example 1-2: Preparation of Compound GH1-b)

[0120]

[0121] Compound GH1-a (25 g, 56.4 mmol) and aluminum chloride (AlCl3) (6.8 g, 28.2 mmol) were added to C6D- (800 ml), and the mixture was stirred for 3 hours. After the reaction was completed, D2O (100 ml) was added, stirred for 30 minutes, and then trimethylamine (10 ml) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over anhydrous magnesium sulfate, the organic solvent was removed under reduced pressure, and the resulting product was purified by column chromatography to prepare compound GH1-b (22.9 g, 88%, [M+H] + = 463).

[0122] (Preparation Example 1-3: Preparation of Compound GH1-c)

[0123]

[0124] Under a nitrogen atmosphere, compound GH1-b (50 g, 108.2 mmol) and bis(pinacolato)diboron (27.7 g, 119 mmol) were added to 1000 ml of Diox. The mixture was stirred and refluxed. Then, potassium acetate (31.2 g, 324.6 mmol) was added thereto, and the mixture was stirred well. Then, palladium dibenzylideneacetone palladium (1.9 g, 3.2 mmol) and tricyclohexylphosphine (1.8 g, 6.5 mmol) were added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the resulting solid was filtered. The solid was added to 1797 ml of chloroform, dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to obtain a gray solid compound GH1-c (50.3 g, 84%, MS: [M+H] + = 554).

[0125] (Preparation Example 1-4: Preparation of Compound GH1)

[0126]

[0127] Under a nitrogen atmosphere, compound GH1-c (30 g, 54.2 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (14.5 g, 54.2 mmol) were added to 900 ml of tetrahydrofuran. The mixture was stirred and refluxed. Then, potassium carbonate (22.5 g, 162.6 mmol) was dissolved in 22 ml of water and added thereto. The mixture was stirred well, and then tetrakis(triphenylphosphine)palladium (1.9 g, 1.6 mmol) was added. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and then the resulting solid was filtered. The solid was added to 1785 ml of chloroform, dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a white solid compound GH1 (22.9 g, 64%, MS: [M+H] + = 659).

[0128] Preparation Example 2: Preparation of Compound GH2

[0129]

[0130] Compound GH2 ([M+H] + = 669) was prepared in the same manner as in the preparation method of Preparation Example 1-4, except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0131] Preparation Example 3: Preparation of Compound GH3

[0132] (Preparation Example 3-1: Preparation of Compound GH3-a)

[0133]

[0134] Compound GH3-a ([M+H] + = 443) was prepared in the same manner as in the preparation method of Preparation Example 1-1, except that 2-chloro-9H-carbazole was used instead of 4-chloro-9H-carbazole.

[0135] (Preparation Example 3-2: Preparation of Compound GH3-b)

[0136]

[0137] Compound GH3-b ([M+H] + = 463) was prepared in the same manner as in the preparation method of Preparation Example 1-2, except that Compound GH3-a was used instead of Compound GH1-a.

[0138] (Preparation Example 3-3: Preparation of Compound GH3-c)

[0139]

[0140] Compound GH3-c ([M+H] + = 554) was prepared in the same manner as in the preparation method of Preparation Example 1-3, except that Compound GH3-b was used instead of Compound GH1-b.

[0141] (Preparation Example 3-4: Preparation of Compound GH3)

[0142]

[0143] Compound GH3 ([M+H] + = 669) was prepared in the same manner as in the preparation method of Preparation Example 1-4, except that Compound GH3-c was used instead of Compound GH1-c and 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0144] Preparation Example 4: Preparation of Compound GH4

[0145] (Preparation Example 4-1: Preparation of Compound GH4-a)

[0146]

[0147] Compound GH4-a ([M+H]) was prepared in the same manner as in the preparation method of Preparation Example 1-1 + = 443), except that 2-bromo-9-phenyl-9H-carbazole was used instead of 4-bromo-9-phenyl-9H-carbazole and 2-chloro-9H-carbazole was used instead of 4-chloro-9H-carbazole.

[0148] (Preparation Example 4-2: Preparation of Compound GH4-b)

[0149]

[0150] Compound GH4-b ([M+H]) was prepared in the same manner as in the preparation method of Preparation Example 1-2 + = 463), except that Compound GH4-a was used instead of Compound GH1-a.

[0151] (Preparation Example 4-3: Preparation of Compound GH4-c)

[0152]

[0153] Compound GH4-c ([M+H]) was prepared in the same manner as in the preparation method of Preparation Example 1-3 + = 554), except that Compound GH4-b was used instead of Compound GH1-b.

[0154] (Preparation Example 4-4: Preparation of Compound GH4)

[0155]

[0156] Compound GH4 ([M+H]) was prepared in the same manner as in the preparation method of Preparation Example 1-4 + = 735), except that Compound GH4-c was used instead of Compound GH1-c and 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.

[0157] Preparation Example 5: Preparation of Compound GH5

[0158] (Preparation Example 5-1: Preparation of Compound GH5-a)

[0159]

[0160] Compound GH5-a ([M+H]) was prepared in the same manner as in the preparation method of Preparation Example 1-1 += 443), except that 3-bromo-9-phenyl-9H-carbazole is used instead of 4-bromo-9-phenyl-9H-carbazole and 1-chloro-9H-carbazole is used instead of 4-chloro-9H-carbazole.

[0161] (Preparation Example 5-2: Preparation of Compound GH5-b)

[0162]

[0163] Compound GH5-b ([M+H] was prepared in the same manner as in the preparation method of Preparation Example 1-2 + = 463), except that Compound GH5-a is used instead of Compound GH1-a.

[0164] (Preparation Example 5-3: Preparation of Compound GH5-c)

[0165]

[0166] Compound GH5-c ([M+H] was prepared in the same manner as in the preparation method of Preparation Example 1-3 + = 554), except that Compound GH5-b is used instead of Compound GH1-b.

[0167] (Preparation Example 5-4: Preparation of Compound GH5)

[0168]

[0169] Compound GH5 ([M+H] was prepared in the same manner as in the preparation method of Preparation Example 1-4 + = 669), except that Compound GH5-c is used instead of Compound GH1-c and 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine is used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0170] Preparation Example 6: Preparation of Compound GH6

[0171] (Preparation Example 6-1: Preparation of Compound GH6-a)

[0172]

[0173] Compound GH6-a ([M+H] was prepared in the same manner as in the preparation method of Preparation Example 1-1 + = 443), except that 1-bromo-9-phenyl-9H-carbazole is used instead of 4-bromo-9-phenyl-9H-carbazole and 3-chloro-9H-carbazole is used instead of 4-chloro-9H-carbazole.

[0174] (Preparation Example 6-2: Preparation of Compound GH6-b)

[0175]

[0176] Compound GH6-b ([M+H] + =463) was prepared in the same manner as in the preparation method of Preparation Example 1-2, except that compound GH6-a was used instead of compound GH1-a.

[0177] (Preparation Example 6-3: Preparation of Compound GH6-c)

[0178]

[0179] Compound GH6-c ([M+H] + =554) was prepared in the same manner as in the preparation method of Preparation Example 1-3, except that compound GH6-b was used instead of compound GH1-b.

[0180] (Preparation Example 6-4: Preparation of Compound GH6)

[0181]

[0182] Compound GH6 ([M+H] + =669) was prepared in the same manner as in the preparation method of Preparation Example 1-4, except that compound GH6-c was used instead of compound GH1-c and 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0183] Preparation Example 7: Preparation of Compound GH7

[0184] (Preparation Example 7-1: Preparation of Compound GH7-a)

[0185]

[0186] Compound GH7-a ([M+H] + =520) was prepared in the same manner as in the preparation method of Preparation Example 1-1, except that 9-([1,1'-biphenyl]-3-yl)-1-bromo-9H-carbazole was used instead of 4-bromo-9-phenyl-9H-carbazole.

[0187] (Preparation Example 7-2: Preparation of Compound GH7-b)

[0188]

[0189] Compound GH7-b ([M+H]+ = 543), except that compound GH7-a is used instead of compound GH1-a.

[0190] (Preparation Example 7-3: Preparation of Compound GH7-c)

[0191]

[0192] Compound GH7-c ([M+H] + = 634) was prepared in the same manner as in the preparation method of Preparation Example 1-3, except that compound GH7-b was used instead of compound GH1-b.

[0193] (Preparation Example 7-4: Preparation of Compound GH7)

[0194]

[0195] Compound GH7 ([M+H] + = 740) was prepared in the same manner as in the preparation method of Preparation Example 1-4, except that compound GH7-c was used instead of compound GH1-c.

[0196] Preparation Example 8: Preparation of Compound GH8

[0197] (Preparation Example 8-1: Preparation of Compound GH8-a)

[0198]

[0199] Compound GH8-a ([M+H] + = 458) was prepared in the same manner as in the preparation method of Preparation Example 1-1, except that 2-bromo-9-phenyl-9H-carbazole-1,3,4,5,6,7,8-d7 was used instead of 4-bromo-9-phenyl-9H-carbazole and 4-chloro-9H-carbazole-1,2,3,5,6,7,8-d7 was used instead of 4-chloro-9H-carbazole.

[0200] (Preparation Example 8-2: Preparation of Compound GH8-b)

[0201]

[0202] Compound GH8-b ([M+H] + = 549) was prepared in the same manner as in the preparation method of Preparation Example 1-3, except that compound GH8-a was used instead of compound GH1-b.

[0203] (Preparation Example 8-3: Preparation of Compound GH8)

[0204]

[0205] Compound GH8 ([M+H] was prepared in the same manner as in the preparation methods of Preparation Examples 1-4 + = 744), except that compound GH8-b was used instead of compound GH1-c and 2-chloro-4-(dibenz[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0206] [Experimental Example]

[0207] Experimental Example 1

[0208] A glass substrate coated with an ITO (indium tin oxide) thin film with a thickness of 100 nm was placed in distilled water containing a detergent dissolved therein, and ultrasonic washing was performed. At this time, the detergent used was a product commercially available from Fisher Co., and the distilled water was distilled water filtered twice using a filter commercially available from Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After washing with distilled water was completed, the substrate was ultrasonically washed and dried with isopropyl alcohol, acetone, and methanol solvents, and then transferred to a plasma cleaner. Then, the substrate was cleaned with oxygen plasma for 5 minutes and then transferred to a vacuum evaporator.

[0209] On the ITO transparent electrode thus prepared, the following compound HI-A was thermally vacuum deposited to a thickness of 60 nm to form a hole injection layer.

[0210] On the hole injection layer, the following compound HAT was vacuum deposited to form a first hole transport layer with a thickness of 5 nm, and on the first hole transport layer, the following compound HT-A was vacuum deposited to form a second hole transport layer with a thickness of 50 nm.

[0211] On the hole transport layer, the following compound HT-B was thermally vacuum deposited to a thickness of 45 nm to form an electron blocking layer. The previously prepared compound GH1 was mixed with the following compound GH-P at a weight ratio of 1:1, and then vacuum deposited on the electron blocking layer with the following compound GD at a weight ratio of 90:10 to a thickness of 40 nm to form a light emitting layer. On the light emitting layer, the following compound ET-A was vacuum deposited to a thickness of 5 nm to form a hole blocking layer. On the hole blocking layer, the following compound ET-B and the following compound LiQ were vacuum deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 35 nm.

[0212] Lithium fluoride (LiF) and aluminum were sequentially deposited on the electron injection and transport layer to have thicknesses of 1 nm and 100 nm, respectively, to form a cathode, thereby manufacturing an organic light emitting device.

[0213]

[0214] During the above process, the vacuum deposition rate of the organic material was maintained at 0.04 nm / sec to 0.09 nm / sec, the deposition rate of lithium fluoride was maintained at 0.03 nm / sec, and the deposition rate of aluminum was maintained at 0.2 nm / sec. The degree of vacuum during deposition was maintained at 1×10 -7 Torr to 5×10 -5 Torr.

[0215] Examples 2 to 8 and Comparative Examples 1 to 5

[0216] An organic light-emitting device was fabricated in the same manner as in Example 1, except that the compound listed in Table 1 below was used instead of compound GH1 in Example 1. In Table 1 below, the structures of compounds GH9 to GH13 are as follows.

[0217]

[0218] [Experimental Example]

[0219] The voltage, efficiency, emission color, and lifetime (T 95 ) were measured by applying an electric current to the organic light-emitting devices fabricated in Examples 1 to 8 and Comparative Examples 1 to 5, and the results are shown in Table 1 below. At this time, the voltage and efficiency were measured by applying a current density of 10 mA / cm 2 , and T 95 means the time (hours) required for the luminance to decrease to 95% of the initial luminance at a current density of 10 mA / cm 2 .

[0220] [Table 1]

[0221]

[0222] As shown in Table 1, it was determined that the organic light-emitting device of one embodiment exhibited more excellent characteristics in terms of voltage, efficiency, and lifetime compared to the organic light-emitting devices containing un-deuterium-substituted compounds GH9, GH10, GH12, or GH13. In addition, even when deuterium was substituted in compound GH11 in which substituents other than carbazole were deuterium-substituted, it was found that when the substitution position was not carbazole, the voltage, efficiency, and lifetime were all inferior to those of the organic light-emitting device of the example.

[0223] Therefore, as shown in Table 1, it can be determined that when the compound represented by Chemical Formula 1 is used as the host for an organic light-emitting device, it exhibits characteristics of low voltage, high efficiency, and long lifetime.

[0224] [Explanation of Reference Numerals]

[0225] 1: Substrate 2: Anode

[0226] 3: Light-emitting layer 4: Cathode

[0227] 5: Hole injection layer 6: First hole transport layer

[0228] 7: Second hole transport layer 8: Electron blocking layer

[0229] 9: Hole blocking layer 10: Electron injection and transport layer

Claims

1. A compound represented by the following Chemical Formula 1: [Chemical Formula 1] Among them, In Chemical Formula 1, Ar1 and Ar2 are each independently a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl containing at least one selected from N, O and S, L1 and L2 are each independently a single bond; a substituted or unsubstituted C 6-60 arylene; or a substituted or unsubstituted C 2-60 heteroarylene containing at least one selected from N, O, and S, Ar3 is a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl containing at least one selected from N, O, and S, X1 to X3 are each independently N or CR, R is hydrogen; deuterium; substituted or unsubstituted C 1-60 alkyl; substituted or unsubstituted C 6-60 aryl; or substituted or unsubstituted C containing at least one selected from N, O and S 2-60 heteroaryl, D is deuterium, a and c are each independently an integer from 0 to 3, b and d are each independently an integer from 0 to 4, and at least one of a to d is 1 or greater.

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

3. The compound according to claim 1, wherein: Ar1 and Ar2 are each independently phenyl, phenyl substituted with 5 deuteriums, biphenyl, or dibenzofuranyl.

4. The compound according to claim 1, wherein: At least one of Ar1 and Ar2 is phenyl, or phenyl substituted with 5 deuteriums.

5. The compound according to claim 1, wherein: L1 and L2 are each independently a single bond, or phenylene which is unsubstituted or substituted with at least one deuterium.

6. The compound according to claim 1, wherein: L1 and L2 are each independently a single bond, or phenylene.

7. The compound according to claim 1, wherein: At least one of L1 and L2 is a single bond.

8. The compound according to claim 1, wherein: Ar3 is phenyl or biphenyl, wherein the phenyl or biphenyl is unsubstituted or substituted with at least one deuterium.

9. The compound according to claim 1, wherein: Ar3 is phenyl, phenyl substituted with 5 deuteriums, biphenyl, or biphenyl substituted with 9 deuteriums.

10. The compound according to claim 1, wherein: X1 to X3 are each N.

11. The compound according to claim 1, wherein: a and c are each 3, and b and d are each 4.

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

13. An organic light emitting device, comprising: First electrode; A second electrode arranged to face 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 contains the compound according to any one of claims 1 to 12.

14. The organic light-emitting device according to claim 13, wherein: The organic material layer is a light-emitting layer.

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