Novel compound and organic light-emitting device comprising same

Abstract

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

Description

Technical Field

[0001] Cross - reference to related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2023-0052246 filed on April 20, 2023, and Korean Patent Application No. 10-2024-0048039 filed on April 9, 2024, and includes all the contents disclosed in the documents of the Korean patent applications as part of this specification.

[0003] The present invention 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 using organic substances. Organic light-emitting devices using the organic light-emitting phenomenon have a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a large amount of research is being conducted.

[0005] An organic light-emitting device generally has a structure including an anode and a cathode and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light-emitting device, the organic layer is mostly formed of a multilayer structure formed of different substances, for example, it 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. For such a 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 layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons return to the ground state again.

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

[0007] Prior Art Documents

[0008] Patent Document 1: Korean Patent Publication No. 10-2000-0051826 Summary of the Invention

[0009] Technical Problem

[0010] The present invention relates to novel compounds and organic light-emitting devices comprising the same.

[0011] Solution to the Problem

[0012] The present invention provides a compound represented by the following Chemical Formula 1:

[0013] [Chemical Formula 1]

[0014]

[0015] In the above Chemical Formula 1,

[0016] Y is O or S,

[0017] D is deuterium,

[0018] n and m are each independently an integer from 0 to 3,

[0019] p and q are each independently an integer from 1 to 4,

[0020] R1 and R2 are each independently hydrogen; deuterium; substituted or unsubstituted C 6-24 aryl; or substituted or unsubstituted C containing any one or more of N, O, and S selected from 2-24 heteroaryl,

[0021] However, at least one of R1 and R2 is deuterium; C substituted with more than one deuterium 6-24 aryl; or C substituted with more than one deuterium and containing any one or more of N, O, and S selected from 2-24 heteroaryl,

[0022] L1 is a single bond; substituted or unsubstituted C 6-24 arylene; or substituted or unsubstituted C containing any one or more of N, O, and S selected from 2-24 heteroarylene,

[0023] L2 is substituted or unsubstituted C 6-24 arylene; or substituted or unsubstituted C containing any one or more of N, O, and S selected from 2-24 heteroarylene,

[0024] However, when L1 is a single bond, L2 is substituted or unsubstituted C 6-24 arylene,

[0025] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-24 aryl; or substituted or unsubstituted C containing any one or more of N, O, and S selected from 2-24 heteroaryl.

[0026] In addition, the present invention provides an organic light-emitting device, which includes: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, and one or more of the organic layers contain a compound represented by the above Chemical Formula 1.

[0027] Advantages of the Invention

[0028] The compound represented by the above Chemical Formula 1 can be used as a material for an organic layer of an organic light-emitting device, and can exhibit improved efficiency, lower driving voltage, and / or improved lifetime characteristics in the organic light-emitting device. In particular, the compound represented by the above Chemical Formula 1 can be used as a material for hole injection, hole transport, hole injection and transport, electron blocking, light emission, electron transport, or electron injection. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Figure 1 An example of an organic light-emitting device including a substrate 1, an anode 2, an organic layer 3, and a cathode 4 is illustrated.

[0030] 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 8, a hole blocking layer 9, an electron transport layer 10, an electron injection layer 11, and a cathode 4 is illustrated.

[0031] Figure 3 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 8, a hole blocking layer 9, an electron injection and transport layer 12, and a cathode 4 is illustrated. DETAILED DESCRIPTION OF THE INVENTION

[0032] Hereinafter, the present invention will be described in more detail to assist in understanding the present invention.

[0033] The present invention provides a compound represented by the above Chemical Formula 1.

[0034] In the present specification, represents a bond connected to another substituent.

[0035] In the present specification, the term "substituted or unsubstituted" means being substituted or unsubstituted by one or more substituents selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group 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 heterocyclic group containing one or more of N, O, and S atoms, or being substituted or unsubstituted by a substituent formed by connecting two or more of the above-exemplified substituents. For example, the "substituent formed by connecting two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent formed by connecting two phenyl groups.

[0036] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably it is 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

[0037]

[0038] In this specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound having the following structural formula, but is not limited thereto.

[0039]

[0040] In this specification, the number of carbon atoms in the imide group is not particularly limited, but preferably it is 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

[0041]

[0042] In this specification, examples of the silyl group specifically include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0043] In this specification, examples of the boron group specifically include trimethylboron, triethylboron, tert-butyldimethylboron, triphenylboron, phenylboron, etc., but are not limited thereto.

[0044] In this specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

[0045] In this specification, the above-mentioned alkyl group may be linear or branched, and there is no particular limitation on the number of carbon atoms, but it is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the above-mentioned alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms of the above-mentioned 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, nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto.

[0046] In this specification, the above-mentioned alkenyl group may be linear or branched, and there is no particular limitation on the number of carbon atoms, but it is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the above-mentioned alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above-mentioned alkenyl group is 2 to 6. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethen-1-yl, 2,2-bis(diphenyl-1-yl)ethen-1-yl, stilbenyl, styryl, etc., but are not limited thereto.

[0047] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is 3 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is 3 to 6. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0048] In this specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. 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. Regarding the above aryl group, as the monocyclic aryl group, it may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. As the above polycyclic aryl group, it may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, -yl group, a fluorenyl group, etc., but is not limited thereto.

[0049] In this specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. When the above fluorenyl group is substituted, it may be etc. But it is not limited thereto.

[0050] In this specification, the heterocyclic group is a heterocyclic group containing one or more of N, O, and S as hetero elements, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophenyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, -azolyl group, a diazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidinyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl group, an indolyl group, a carbazolyl group, a benzo -azolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuryl group, a phenanthroline group, an iso -azolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuryl group, etc., but is not limited thereto.

[0051] In this specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamino group is the same as the exemplified aryl group above. In this specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the exemplified alkyl group above. In this specification, the heteroaryl group in the heteroarylamine may apply the above description regarding the heterocyclic group. In this specification, the alkenyl group in the aralkenyl group is the same as the exemplified alkenyl group above. In this specification, the arylene group is a divalent group, and in addition, the above description regarding the aryl group may be applied. In this specification, the heteroarylene group is a divalent group, and in addition, the above description regarding the heterocyclic group may be applied. In this specification, the hydrocarbon ring is not a monovalent group, but is formed by combining two substituents, and in addition, the above description regarding the aryl group or the cycloalkyl group may be applied. In this specification, the heterocycle is not a monovalent group, but is formed by combining two substituents, and in addition, the above description regarding the heterocyclic group may be applied.

[0052] The above Chemical Formula 1 has a structure in which a triazine substituent is connected to the 1-carbon of a dibenzofuran or dibenzothiophene ring and a carbazole substituent is included at the 6-carbon. At this time, the carbazole ring included in the above Chemical Formula 1 contains one or more deuteriums and / or includes an aryl or heteroaryl group substituted with one or more deuteriums. Due to satisfying such structural characteristics, the compound represented by the above Chemical Formula 1 is used in an organic light-emitting device and can reduce the driving voltage and significantly improve the lifetime characteristics.

[0053] Preferably, each of R1 and R2 is independently hydrogen, deuterium, a phenyl group which is substituted or unsubstituted with one or more deuteriums, a biphenyl group which is substituted or unsubstituted with one or more deuteriums, or a terphenyl group which is substituted or unsubstituted with one or more deuteriums.

[0054] L1 is a single bond, a phenylene group, a biphenyldiyl group, a terphenyldiyl group, a naphthalenediyl group, a dibenzofurandiyl group, or a dibenzothiophenediyl group. Except when the above L1 is a single bond, L1 may be unsubstituted or substituted with one or more deuteriums.

[0055] L2 is a phenylene group, a biphenyldiyl group, a terphenyldiyl group, an anthracenediyl group, a triphenylenediyl group, a dimethylfluorenediyl group, a dibenzofurandiyl group, or a dibenzothiophenediyl group. The above L2 may be unsubstituted or substituted with one or more deuteriums.

[0056] Preferably, L2 is a substituted or unsubstituted C 6-24 arylene group.

[0057] More preferably, L2 is a phenylene group, a biphenyldiyl group, a terphenyldiyl group, an anthracenediyl group, a triphenylenediyl group, or a dimethylfluorenediyl group, and the above L2 may be unsubstituted or substituted with one or more deuteriums.

[0058] More preferably, L2 is a phenylene group, a biphenyldiyl group, or a terphenyldiyl group, and the above L2 may be unsubstituted or substituted with one or more deuteriums.

[0059] Preferably, L2 may be a terphenyldiyl group which is unsubstituted or substituted with one or more deuteriums.

[0060] Preferably, each of Ar1 and Ar2 is independently a phenyl group, a biphenyl group, a dimethylfluorenyl group, a dibenzofuran group, or a dibenzothiophene group. Each of the above Ar1 and Ar2 may be independently unsubstituted or substituted with one or more deuteriums.

[0061] Representative examples of the compound represented by the above Chemical Formula 1 are as follows:

[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]

[0089]

[0090]

[0091]

[0092] In addition, the present invention provides a method for manufacturing a compound represented by the above Chemical Formula 1. As an example, the compound represented by the above Chemical Formula 1 can be manufactured by the manufacturing method shown in Reaction Formula 1 below.

[0093] [Reaction Formula 1]

[0094]

[0095] In the above Reaction Formula 1, Y, D, m, n, p, q, R1, R2, L1, L2, Ar1 and Ar2 are the same as defined in the above Chemical Formula 1, X is a halogen, and preferably, X is fluorine, chlorine or bromine.

[0096] The above Reaction Formula 1 is an amine substitution reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reaction groups for the amine substitution reaction can be changed according to the techniques known in the art. The above manufacturing method can be more specific in the manufacturing examples described later.

[0097] In addition, the present invention provides an organic light-emitting device including the compound represented by the above Chemical Formula 1. As an example, the present invention provides an organic light-emitting device including: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, and one or more of the organic layers contain the compound represented by the above Chemical Formula 1.

[0098] The organic layer of the organic light-emitting device of the present invention can be formed of a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto, and it can include a smaller number of organic layers.

[0099] In addition, the above organic layer can include a light-emitting layer, and the light-emitting layer contains the compound represented by the above Chemical Formula 1. In particular, the compound according to the present invention can be used as a host of the light-emitting layer.

[0100] In addition, the above organic layer can include a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer contains the compound represented by the above Chemical Formula 1.

[0101] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. Further, the organic light-emitting device according to the present invention may be an organic light-emitting device having an inverted structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structural example of the organic light-emitting device according to an embodiment of the present invention is illustrated in Figures 1 to 3 .

[0102] Figure 1 An example of an organic light-emitting device composed of a substrate 1, an anode 2, an organic layer 3, and a cathode 4 is illustrated. In the structure described above, the compound represented by Chemical Formula 1 may be included in the organic layer.

[0103] Figure 2 An example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron transport layer 10, an electron injection layer 11, and a cathode 4 is illustrated. In the structure described above, the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the electron blocking layer, the light-emitting layer, the hole blocking layer, the electron transport layer, and the electron injection layer.

[0104] Figure 3 An example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 12, and a cathode 4 is illustrated. In the structure described above, the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the electron blocking layer, the light-emitting layer, the hole blocking layer, and the electron injection and transport layer. As an example, it may be included in the light-emitting layer.

[0105] The organic light-emitting device according to the present invention may be manufactured using materials and methods known in the art, in addition to including the compound represented by Chemical Formula 1 in one or more of the organic layers. Further, when the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0106] For example, an organic light-emitting device according to the present invention can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be manufactured as follows: using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal, a conductive metal oxide, or an alloy thereof is evaporated on the substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode. After that, a substance that can be used as a cathode is evaporated on the organic layer to manufacture the device. In addition to this method, an organic light-emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on the substrate.

[0107] In addition, the compound represented by Chemical Formula 1 above can form an organic layer not only by using a vacuum evaporation method but also by using a solution coating method when manufacturing an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

[0108] In addition to these methods, an organic light-emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on the substrate (WO 2003 / 012890). However, the manufacturing method is not limited thereto.

[0109] As an example, the above first electrode is an anode, the above second electrode is a cathode, or the above first electrode is a cathode and the above second electrode is an anode.

[0110] As the above anode substance, usually, in order to enable holes to be smoothly injected into the organic layer, a substance with a large work function is preferred. Specific examples of the above anode substance 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; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0111] As the above cathode substance, usually, in order to enable electrons to be easily injected into the organic layer, a substance with a small work function is preferred. Specific examples of the above cathode substance include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure substances such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0112] The above hole injection layer is a layer that injects holes from the electrode. As a hole injection material, the following compounds are preferred: compounds having the ability to transport holes, having the effect of injecting holes from the anode, having an excellent hole injection effect on the light-emitting layer or light-emitting material, preventing excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material, and having excellent thin film forming ability. 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 layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic compounds, hexanitrile hexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinone, and conductive polymers such as polyaniline and polythiophene, but are not limited thereto.

[0113] The above 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 a material that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer, and a material with a large hole mobility is suitable. Specific examples include arylamine-based organic compounds, conductive polymers, and block copolymers having both a conjugated part and a non-conjugated part, but are not limited thereto.

[0114] The above electron blocking layer inhibits the electrons injected from the cathode from recombining in the light-emitting layer but transferring to the anode side, thereby playing a role in improving the efficiency of the organic light-emitting device.

[0115] The above light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include tris(8-hydroxyquinoline)aluminum (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole, and benzimidazole-based compounds; poly(p-phenylene vinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited thereto.

[0116] The above light-emitting layer may contain a host material and a dopant material. As the host material, there are aromatic condensed ring derivatives or heterocyclic compounds, etc. Specifically, as aromatic condensed ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds Pyrimidine derivatives and the like, but not limited thereto. In particular, in the present invention, the compound represented by the above chemical formula 1 can be used as the host material of the light-emitting layer, and in this case, low voltage, high efficiency and / or long life characteristics of the organic light-emitting device can be obtained.

[0117] As the dopant material, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and there are pyrene, anthracene, dinaphthoanthracene, etc. having an arylamino group. The styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino groups. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as the metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0118] The above hole-inhibiting layer is a layer disposed between the electron-transporting layer and the light-emitting layer to prevent the holes injected from the anode from recombining in the light-emitting layer but transferring to the electron-transporting layer, and is also called a hole-blocking layer. A substance with a large ionization energy is preferably used in the hole-inhibiting layer.

[0119] The above electron-transporting layer is a layer that receives electrons from the electron-injecting layer and transports the electrons to the light-emitting layer. The electron-transporting material is a material that can receive electrons well from the cathode and transfer them to the light-emitting layer, and a material with a large electron mobility is suitable. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavone-metal complexes, etc., but not limited thereto. The electron-transporting layer can be used together with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are common materials having a low work function and accompanied by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium and samarium, each accompanied by an aluminum layer or a silver layer in each case.

[0120] The above electron-injecting layer is a layer that injects electrons from the electrode, and preferably uses the following compounds: compounds having the ability to transport electrons, having the effect of injecting electrons from the cathode, having an excellent electron-injecting effect on the light-emitting layer or the light-emitting material, preventing excitons generated in the light-emitting layer from migrating to the hole-injecting layer, and having excellent thin-film forming ability. Specifically, there are fluorenone, anthraquinodimethane, biphenylenequinone, thiopyran dioxide, oxazole, Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorene methane, anthrone, etc. and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, etc., but not limited thereto.

[0121] Examples of the metal coordination compounds include lithium 8-hydroxyquinoline, zinc bis(8-hydroxyquinoline), copper bis(8-hydroxyquinoline), manganese bis(8-hydroxyquinoline), aluminum tris(8-hydroxyquinoline), aluminum tris(2-methyl-8-hydroxyquinoline), gallium tris(8-hydroxyquinoline), beryllium bis(10-hydroxybenzo[h]quinoline), zinc bis(10-hydroxybenzo[h]quinoline), gallium chloride bis(2-methyl-8-hydroxyquinoline), gallium (o-cresol) bis(2-methyl-8-hydroxyquinoline), aluminum (1-naphthol) bis(2-methyl-8-hydroxyquinoline), gallium (2-naphthol) bis(2-methyl-8-hydroxyquinoline), etc., but not limited thereto.

[0122] According to an embodiment of the present invention, the above electron transport material and electron injection material can be simultaneously vapor-deposited to form a single layer such as an electron injection and transport layer.

[0123] According to the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0124] In addition, the compound represented by the above Chemical Formula 1 can be included not only in an organic light-emitting device but also in an organic solar cell or an organic transistor.

[0125] The manufacture of the compound represented by the above Chemical Formula 1 and the organic light-emitting device including the same will be specifically described in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

[0126] [Synthesis Example]

[0127] Synthesis Example 1: Synthesis of Compound 1

[0128]

[0129] (Synthesis of Intermediate 1-1)

[0130] Under a nitrogen atmosphere, 1-bromo-7-chlorodibenzo[b,d]furan (33.5 g, 119 mmol) and bis(pinacolato)diboron (30.5 g, 130.9 mmol) were added to 670 ml of di- In dioxane, stir and reflux. Then, add potassium acetate (34.3 g, 357 mmol), and after sufficient stirring, add [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (2.6 g, 3.6 mmol). After reacting for 7 hours, cool to room temperature, filter the organic layer to remove salts, and then distill the filtered organic layer. Redissolve it in 391 ml of chloroform, wash it twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and then distill the filtrate under reduced pressure. Recrystallize the concentrated compound from chloroform and ethanol to obtain a gray solid compound 1-1 (34 g, 87%, MS: [M+H] + = 329.6).

[0131] (Synthesis of Intermediate 1-2)

[0132] Under a nitrogen atmosphere, add compound 1-1 (37 g, 112.6 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (30.1 g, 112.6 mmol) to 740 ml of THF, stir and reflux. Then, dissolve potassium carbonate (46.7 g, 337.8 mmol) in 47 ml of water and add it. After sufficient stirring, add tetrakis(triphenylphosphine)palladium(0) (3.9 g, 3.4 mmol). After reacting for 8 hours, cool to room temperature and filter the resulting solid. Dissolve the solid in 1466 ml of chloroform, wash it twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and then distill the filtrate under reduced pressure. Recrystallize the concentrated compound from chloroform and ethyl acetate to obtain a yellow solid compound 1-2 (34.2 g, 70%, MS: [M+H] + = 434.9).

[0133] (Synthesis of Intermediate 1-3)

[0134] Under a nitrogen atmosphere, add compound 1-2 (34.2 g, 78.8 mmol) and bis(pinacolato)diboron (22 g, 86.7 mmol) to 684 ml of di In an alkane, stir and reflux. Then, add potassium acetate (22.7 g, 236.5 mmol), and after sufficient stirring, add [1,1'-bis(diphenylphosphino)ferrocene] palladium(II) dichloride (1.7 g, 2.4 mmol). After reacting for 3 hours, cool to room temperature, filter the organic layer to remove salts, and then distill the filtered organic layer. Redissolve it in 414 ml of chloroform, wash twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and then distill the filtrate under reduced pressure. Recrystallize the concentrated compound from chloroform and ethanol to obtain a gray solid compound 1-3 (28.2 g, 68%, MS: [M+H] + = 526.4).

[0135] (Synthesis of Intermediate 1-4)

[0136] Under a nitrogen atmosphere, add compound 1-3 (28.2 g, 53.7 mmol) and 1-chloro-2-fluorobenzene (7 g, 53.7 mmol) to 564 ml of THF, stir and reflux. Then, dissolve potassium carbonate (22.3 g, 161 mmol) in 22 ml of water and add it. After sufficient stirring, add tetrakis(triphenylphosphine)palladium(0) (1.9 g, 1.6 mmol). After reacting for 8 hours, cool to room temperature and filter the resulting solid. Dissolve the solid in 795 ml of chloroform, wash twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and then distill the filtrate under reduced pressure. Recrystallize the concentrated compound from chloroform and ethyl acetate to obtain a white solid compound 1-4 (16.7 g, 63%, MS: [M+H] + = 494.5).

[0137] (Synthesis of Compound 1)

[0138] Under a nitrogen atmosphere, add compound 1-4 (16.7 g, 33.8 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (5.9 g, 33.8 mmol) to 334 ml of dimethylformamide, stir and reflux. Then, add cesium carbonate (33.1 g, 101.5 mmol). After sufficient stirring, react for 3 hours, cool to room temperature, and filter the resulting solid. Dissolve the solid in 657 ml of toluene, wash twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and then distill the filtrate under reduced pressure. Recrystallize the concentrated compound from toluene and ethyl acetate to obtain a white solid compound 1 (11.4 g, 52%, MS: [M+H] += 647.8).

[0139] Synthesis Example 2: Synthesis of Compound 2

[0140]

[0141] (Synthesis of Intermediate 2-1)

[0142] Under a nitrogen atmosphere, Compound 1-3 (40 g, 76.1 mmol) and 1-chloro-3-fluorobenzene (9.9 g, 76.1 mmol) were added to 800 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (31.6 g, 228.4 mmol) was dissolved in 32 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (2.6 g, 2.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was added to 1127 ml of chloroform and dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give a white solid compound 2-1 (23.7 g, 63%, MS: [M+H] + = 494.5).

[0143] (Synthesis of Compound 2)

[0144] Under a nitrogen atmosphere, Compound 2-1 (23.7 g, 48 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (8.3 g, 48 mmol) were added to 474 ml of dimethylformamide, and the mixture was stirred and refluxed. Then, cesium carbonate (46.9 g, 144.1 mmol) was added, and after thorough stirring, the reaction was carried out for 4 hours. After cooling to room temperature, the resulting solid was filtered. The solid was added to 932 ml of toluene and dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to give a white solid compound 2 (20.8 g, 67%, MS: [M+H] + = 647.8).

[0145] Synthesis Example 3: Synthesis of Compound 3

[0146]

[0147] (Synthesis of Intermediate 3-1)

[0148] Under a nitrogen atmosphere, compound 1-3 (34 g, 64.7 mmol) and 3-chloro-5-fluoro-1,1'-biphenyl (13.4 g, 64.7 mmol) were added to 680 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (26.8 g, 194.1 mmol) was dissolved in 27 ml of water and added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (2.2 g, 1.9 mmol) was added. After reacting for 8 hours, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was added to 1106 ml of chloroform and dissolved. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, the mixture was filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a white solid compound 3-1 (19.5 g, 53%, MS: [M+H] + = 570.6).

[0149] (Synthesis of Compound 3)

[0150] Under a nitrogen atmosphere, compound 3-1 (19.5 g, 34.2 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (5.9 g, 34.2 mmol) were added to 390 ml of dimethylformamide, and the mixture was stirred and refluxed. Then, cesium carbonate (33.5 g, 102.7 mmol) was added. After thorough stirring, the reaction was carried out for 6 hours. After cooling to room temperature, the resulting solid was filtered. The solid was added to 742 ml of toluene and dissolved. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, the mixture was filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to obtain a white solid compound 3 (13.4 g, 54%, MS: [M+H] + = 723.9).

[0151] Synthesis Example 4: Synthesis of Compound 4

[0152]

[0153] (Synthesis of Intermediate 4-1)

[0154] Under a nitrogen atmosphere, compound 1-3 (41 g, 78 mmol) and 3-chloro-3'-fluoro-1,1'-biphenyl (16.1 g, 78 mmol) were added to 820 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (32.4 g, 234.1 mmol) was dissolved in 32 ml of water and added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (2.7 g, 2.3 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 dissolved in 1334 ml of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a white solid compound 4-1 (33.3 g, 75%, MS: [M+H] + = 570.6).

[0155] (Synthesis of Compound 4)

[0156] Under a nitrogen atmosphere, compound 4-1 (33.3 g, 58.5 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (10.1 g, 58.5 mmol) were added to 666 ml of dimethylformamide, and the mixture was stirred and refluxed. Then, cesium carbonate (57.1 g, 175.4 mmol) was added. After thorough stirring, the reaction was carried out for 5 hours, and after cooling to room temperature, the resulting solid was filtered. The solid was dissolved in 1268 ml of toluene, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to obtain a white solid compound 4 (26.2 g, 62%, MS: [M+H] + = 723.9).

[0157] Synthesis Example 5: Synthesis of Compound 5

[0158]

[0159] (Synthesis of Intermediate 5-1)

[0160] Under a nitrogen atmosphere, 1-bromo-7-chlorodibenzo[b,d]furan-2,3,4,6,8,9-d6 (52 g, 180.8 mmol) and bis(pinacolato)diboron (46.4 g, 198.9 mmol) were added to 1040 ml of di In an alkane, stir and reflux. Then, potassium acetate (52.1 g, 542.5 mmol) was added, and after sufficient stirring, [1,1'-bis(diphenylphosphino)ferrocene] palladium(II) dichloride (4 g, 5.4 mmol) was added. After reacting for 7 hours, it was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. It was redissolved in 605 ml of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound 5-1 (53.3 g, 88%, MS: [M+H] + = 335.6).

[0161] (Synthesis of Intermediate 5-2)

[0162] Under a nitrogen atmosphere, compound 5-1 (53.3 g, 159.3 mmol) and 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (54.8 g, 159.3 mmol) were added to 1066 ml of THF, and stirred and refluxed. Then, potassium carbonate (66 g, 477.8 mmol) was dissolved in 66 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (5.5 g, 4.8 mmol) was added. After reacting for 6 hours, it was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 2466 ml of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a yellow solid compound 5-2 (64.9 g, 79%, MS: [M+H] + = 517).

[0163] (Synthesis of Intermediate 5-3)

[0164] Under a nitrogen atmosphere, compound 5-2 (64.9 g, 125.8 mmol) and bis(pinacolato)diboron (35.1 g, 138.3 mmol) were added to 1298 ml of di In an alkane, stir and reflux. Then, add potassium acetate (36.3 g, 377.3 mmol). After sufficient stirring, add dichlorobis[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) (2.8 g, 3.8 mmol). After reacting for 6 hours, cool to room temperature. Filter the organic layer to remove salts, and then distill the filtered organic layer. Redissolve it in 764 ml of chloroform, wash twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and distill the filtrate under reduced pressure. Recrystallize the concentrated compound from chloroform and ethanol to obtain a gray solid compound 5-3 (55.8 g, 73%, MS: [M+H] + = 608.6).

[0165] (Synthesis of Intermediate 5-4)

[0166] Under a nitrogen atmosphere, add compound 5-3 (55.8 g, 91.8 mmol) and 4-chloro-4'-fluoro-1,1'-biphenyl (19 g, 91.8 mmol) to 1116 ml of THF, stir and reflux. Then, dissolve potassium carbonate (38.1 g, 275.5 mmol) in 38 ml of water and add it. After sufficient stirring, add tetrakis(triphenylphosphine)palladium(0) (3.2 g, 2.8 mmol). After reacting for 8 hours, cool to room temperature and filter the resulting solid. Dissolve the solid in 1796 ml of chloroform, wash twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and distill the filtrate under reduced pressure. Recrystallize the concentrated compound from chloroform and ethyl acetate to obtain a white solid compound 5-4 (35.9 g, 60%, MS: [M+H] + = 652.8).

[0167] (Synthesis of Compound 5)

[0168] Under a nitrogen atmosphere, add compound 5-4 (35.9 g, 55.1 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (9.5 g, 55.1 mmol) to 718 ml of dimethylformamide, stir and reflux. Then, add cesium carbonate (53.8 g, 165.2 mmol). After sufficient stirring, react for 3 hours, cool to room temperature, and filter the resulting solid. Dissolve the solid in 1330 ml of toluene, wash twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and distill the filtrate under reduced pressure. Recrystallize the concentrated compound from toluene and ethyl acetate to obtain a white solid compound 5 (35.5 g, 80%, MS: [M+H] + = 806).

[0169] Synthesis Example 6: Synthesis of Compound 6

[0170]

[0171] (Synthesis of Intermediate 6-1)

[0172] Under a nitrogen atmosphere, Compound 1-1 (40 g, 121.7 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine

[0173] (47.3 g, 121.7 mmol) were added to 800 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (50.5 g, 365.2 mmol) was dissolved in 50 ml of water and added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (4.2 g, 3.7 mmol) was added. After reacting for 7 hours, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was added to 1862 ml of chloroform and dissolved. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give a white solid compound 6-1 (31 g, 50%, MS: [M+H] + = 511).

[0174] (Synthesis of Intermediate 6-2)

[0175] Under a nitrogen atmosphere, Compound 6-1 (31 g, 60.8 mmol) and bis(pinacolato)diboron (17 g, 66.9 mmol) were added to 620 ml of di ane, and the mixture was stirred and refluxed. Then, potassium acetate (17.5 g, 182.4 mmol) was added. After thorough stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.3 g, 1.8 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was distilled. It was added again to 366 ml of chloroform and dissolved. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to give a gray solid compound 6-2 (27.1 g, 74%, MS: [M+H] + = 602.5).

[0176] (Synthesis of Intermediate 6-3)

[0177] Under a nitrogen atmosphere, compound 6-2 (27.1 g, 45.1 mmol) and 1-chloro-3-fluorobenzene (5.9 g, 45.1 mmol) were added to 542 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.7 g, 135.2 mmol) was dissolved in 19 ml of water and added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.4 mmol) was added. After reacting for 7 hours, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was added to 792 ml of chloroform and dissolved. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 6-3 (15.3 g, 58%, MS: [M+H] + = 587.1).

[0178] (Synthesis of Compound 6)

[0179] Under a nitrogen atmosphere, compound 6-3 (15.3 g, 26.1 mmol) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (4.6 g, 26.1 mmol) were added to 306 ml of dimethylformamide, and the mixture was stirred and refluxed. Then, cesium carbonate (25.5 g, 78.3 mmol) was added. After thorough stirring, the reaction was carried out for 7 hours. After cooling to room temperature, the resulting solid was filtered. The solid was added to 568 ml of toluene and dissolved. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 6 (9.7 g, 51%, MS: [M+H] + = 725.9).

[0180] Synthesis Example 7: Synthesis of Compound 7

[0181]

[0182] (Synthesis of Intermediate 7-1)

[0183] Under a nitrogen atmosphere, compound 1-1 (38 g, 115.6 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (41.4 g, 115.6 mmol) were added to 760 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (47.9 g, 346.9 mmol) was dissolved in 48 ml of water and added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (4 g, 3.5 mmol) was added. After reacting for 6 hours, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was added to 1818 ml of chloroform and dissolved. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 7-1 (43 g, 71%, MS: [M+H] + = 525).

[0184] (Synthesis of Intermediate 7-2)

[0185] Under a nitrogen atmosphere, compound 7-1 (43 g, 82.1 mmol) and bis(pinacolato)diboron (22.9 g, 90.3 mmol) were added to 860 ml of di ane, and the mixture was stirred and refluxed. Then, potassium acetate (23.7 g, 246.2 mmol) was added. After thorough stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.8 g, 2.5 mmol) was added. After reacting 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 505 ml of chloroform and dissolved. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound 7-2 (33.3 g, 66%, MS: [M+H] + = 616.5).

[0186] (Synthesis of Intermediate 7-3)

[0187] Under a nitrogen atmosphere, compound 7-2 (33.3 g, 54.1 mmol) and 2-chloro-4'-fluoro-1,1'-biphenyl (11.2 g, 54.1 mmol) were added to 666 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 162.3 mmol) was dissolved in 22 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.9 g, 1.6 mmol) 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 1071 ml of chloroform and dissolved. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 7-3 (20.7 g, 58%, MS: [M+H] + = 660.7).

[0188] (Synthesis of Compound 7)

[0189] Under a nitrogen atmosphere, compound 7-3 (20.7 g, 31.4 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (5.4 g, 31.4 mmol) were added to 414 ml of dimethylformamide, and the mixture was stirred and refluxed. Then, cesium carbonate (30.7 g, 94.1 mmol) was added. After sufficient stirring, the reaction was carried out for 6 hours. After cooling to room temperature, the resulting solid was filtered. The solid was added to 765 ml of toluene and dissolved. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 7 (15.8 g, 62%, MS: [M+H] + = 814).

[0190] Synthesis Example 8: Synthesis of Compound 8

[0191]

[0192] (Synthesis of Intermediate 8-1)

[0193] Under a nitrogen atmosphere, compound 1-1 (57 g, 173.5 mmol) and 2-(4-bromophenyl)-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine (85.8 g, 173.5 mmol) were added to 1140 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (71.9 g, 520.4 mmol) was dissolved in 72 ml of water and added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (6 g, 5.2 mmol) was added. After reacting for 8 hours, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was added to 3206 ml of chloroform and dissolved. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, the mixture was filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 8-1 (73.7 g, 69%, MS: [M+H] + = 617.1).

[0194] (Synthesis of Intermediate 8-2)

[0195] Under a nitrogen atmosphere, compound 8-1 (73.7 g, 119.6 mmol) and bis(pinacolato)diboron (33.4 g, 131.6 mmol) were added to 1474 ml of di ane, and the mixture was stirred and refluxed. Then, potassium acetate (34.5 g, 358.8 mmol) was added. After thorough stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (2.6 g, 3.6 mmol) was added. After reacting for 5 hours, the reaction mixture was cooled to room temperature. After the organic layer was filtered to remove salts, the filtered organic layer was distilled. It was added again to 846 ml of chloroform and dissolved. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, the mixture was filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound 8-2 (68.6 g, 81%, MS: [M+H] + = 708.7).

[0196] (Synthesis of Intermediate 8-3)

[0197] Under a nitrogen atmosphere, compound 8-2 (68.6 g, 96.9 mmol) and 1-chloro-4-fluorobenzene (12.7 g, 96.9 mmol) were added to 1372 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (40.2 g, 290.8 mmol) was dissolved in 40 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (3.4 g, 2.9 mmol) was added. After reacting for 9 hours, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was added to 1965 ml of chloroform and dissolved. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a white solid compound 8-3 (51.1 g, 78%, MS: [M+H] + = 676.8).

[0198] (Synthesis of Compound 8)

[0199] Under a nitrogen atmosphere, compound 8-3 (51.1 g, 75.6 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (13.1 g, 75.6 mmol) were added to 1022 ml of dimethylformamide, and the mixture was stirred and refluxed. Then, cesium carbonate (73.9 g, 226.8 mmol) was added. After sufficient stirring, the reaction was carried out for 3 hours. After cooling to room temperature, the resulting solid was filtered. The solid was added to 1881 ml of toluene and dissolved. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to obtain a white solid compound 8 (37.6 g, 60%, MS: [M+H] + = 830).

[0200] Synthesis Example 9: Synthesis of Compound 9

[0201]

[0202] (Synthesis of Intermediate 9-1)

[0203] Under a nitrogen atmosphere, 1-bromo-7-chlorodibenzo[b,d]thiophene (36 g, 121 mmol) and bis(pinacolato)diboron (33.8 g, 133.1 mmol) were added to 720 ml of di In an alkane, stir and reflux. Then, add potassium acetate (34.9 g, 362.9 mmol). After stirring well, add [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (2.7 g, 3.6 mmol). After reacting for 3 hours, cool to room temperature. Filter the organic layer to remove salts, and then distill the filtered organic layer. Redissolve it in 417 ml of chloroform, wash twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and then distill the filtrate under reduced pressure. Recrystallize the concentrated compound from chloroform and ethanol to obtain a gray solid compound 9-1 (30 g, 72%, MS: [M+H] + = 345.7).

[0204] (Synthesis of Intermediate 9-2)

[0205] Under a nitrogen atmosphere, add compound 9-1 (30 g, 87 mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (29.9 g, 87 mmol) to 600 ml of THF, stir and reflux. Then, dissolve potassium carbonate (36.1 g, 261.1 mmol) in 36 ml of water and add it. After stirring well, add tetrakis(triphenylphosphine)palladium(0) (3 g, 2.6 mmol). After reacting for 8 hours, cool to room temperature and filter the resulting solid. Dissolve the solid in 1374 ml of chloroform, wash twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and then distill the filtrate under reduced pressure. Recrystallize the concentrated compound from chloroform and ethyl acetate to obtain a yellow solid compound 9-2 (27 g, 59%, MS: [M+H] + = 527.1).

[0206] (Synthesis of Intermediate 9-3)

[0207] Under a nitrogen atmosphere, add compound 9-2 (27 g, 51.3 mmol) and bis(pinacolato)diboron (14.3 g, 56.5 mmol) to 540 ml of di In an alkane, stir and reflux. Then, add potassium acetate (14.8 g, 154 mmol). After sufficient stirring, add [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.1 g, 1.5 mmol). After reacting for 7 hours, cool to room temperature. After filtering the organic layer to remove salts, distill the filtered organic layer. Redissolve it in 317 ml of chloroform, wash twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and distill the filtrate under reduced pressure. Recrystallize the concentrated compound from chloroform and ethanol to obtain a gray solid compound 9-3 (20.6 g, 65%, MS: [M+H] + = 618.6).

[0208] (Synthesis of Intermediate 9-4)

[0209] Under a nitrogen atmosphere, add compound 9-3 (20.6 g, 33.4 mmol) and 1-chloro-3-fluorobenzene (4.4 g, 33.4 mmol) to 412 ml of THF, stir and reflux. Then, dissolve potassium carbonate (13.8 g, 100.1 mmol) in 14 ml of water and add it. After sufficient stirring, add tetrakis(triphenylphosphine)palladium(0) (1.2 g, 1 mmol). After reacting for 9 hours, cool to room temperature and filter the resulting solid. Dissolve the solid in 586 ml of chloroform, wash twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and distill the filtrate under reduced pressure. Recrystallize the concentrated compound from chloroform and ethyl acetate to obtain a white solid compound 9-4 (12.3 g, 63%, MS: [M+H] + = 586.7).

[0210] (Synthesis of Compound 9)

[0211] Under a nitrogen atmosphere, add compound 9-4 (12.3 g, 21 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (3.6 g, 21 mmol) to 246 ml of dimethylformamide, stir and reflux. Then, add cesium carbonate (20.5 g, 63 mmol). After sufficient stirring, react for 6 hours. After cooling to room temperature, filter the resulting solid. Dissolve the solid in 466 ml of toluene, wash twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and distill the filtrate under reduced pressure. Recrystallize the concentrated compound from toluene and ethyl acetate to obtain a white solid compound 9 (11.9 g, 77%, MS: [M+H] + = 739.9).

[0212] [Examples]

[0213] Example 1

[0214] A glass substrate coated with ITO (Indium Tin Oxide) as a thin film with a thickness of was placed in distilled water dissolved with a detergent and washed using ultrasonic waves. At this time, the detergent used was a product of Fischer Co., and the distilled water used was distilled water filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol and then dried, and it was transported to a plasma cleaner. In addition, using oxygen plasma, the above substrate was cleaned for 5 minutes, and then the substrate was transported to a vacuum evaporation machine.

[0215] On the ITO transparent electrode prepared in this way, as a hole injection layer, the following compound HT-A and the following compound PD were thermally vacuum-evaporated at a weight ratio of 95:5 with a thickness of , and then only the following compound HT-A was evaporated with a thickness of to form a hole transport layer. On the above hole transport layer, the following compound HT-B was thermally vacuum-evaporated with a thickness of to form an electron blocking layer (electron suppression layer). On the above electron blocking layer, the previously manufactured compound 1 and the following compound GD were vacuum-evaporated at a weight ratio of 85:15 with a thickness of to form a light-emitting layer. On the above light-emitting layer, the following compound ET-A was vacuum-evaporated with a thickness of to form a hole blocking layer. On the above hole blocking layer, the following compound ET-B and the following Liq compound were thermally vacuum-evaporated at a weight ratio of 2:1 with a thickness of , and then LiF and magnesium were vacuum-evaporated at a weight ratio of 1:1 with a thickness of to form an electron injection and transport layer. On the above electron injection and transport layer, magnesium and silver were evaporated at a weight ratio of 1:4 with a thickness of to form a cathode, thereby manufacturing an organic light-emitting device.

[0216]

[0217] In the above process, the evaporation rate of the organic matter was maintained at The lithium fluoride of the cathode was maintained at The evaporation rate of silver and magnesium was maintained at During evaporation, the vacuum degree was maintained at 2×10 -7 ~5×10 -6A support was used to fabricate an organic light-emitting device.

[0218] Examples 2 to 13 and Comparative Examples 1 to 10

[0219] In Example 1 above, the compound described in Table 1 below was used instead of Compound 1, and an organic light-emitting device was fabricated by the same method as in Example 1 except for this.

[0220] In Examples 10 to 13 and Comparative Examples 6 to 10, the compound described in Table 1 below was used instead of Compound 1 at a weight ratio of 1:1 to fabricate an organic light-emitting device. Taking Example 8 as an example, in Example 1, Compound 1 and Compound H-2 were used instead of Compound 1 at a weight ratio of 1:1.

[0221] The structures of Compound H-2 and C1 to C3 in Table 1 below are shown as follows.

[0222]

[0223] [Experimental Example]

[0224] A current was applied to the organic light-emitting devices fabricated in the above Examples and Comparative Examples to measure the voltage, efficiency, and lifetime (T95), and the results are shown in Table 1 below. At this time, the voltage and efficiency were measured at a current density of 10 mA / cm 2 . In addition, T95 in Table 1 below represents the time measured when the initial brightness decreased to 95% at a current density of 20 mA / cm 2 .

[0225] [Table 1]

[0226]

[0227] Examples 1 to 9 and Comparative Examples 1 to 5 are device examples using a single host in the light-emitting layer.

[0228] It can be confirmed that Examples 1 to 9 significantly improved the lifetime compared with Comparative Example 1 or 2 because they contain a carbazole substituent substituted with deuterium.

[0229] Comparative Example 3 is a device example using a compound in which the carbazole substituent is deuterium-substituted, but the binding position of the substituent to the dibenzofuran parent nucleus is different from that of Chemical Formula 1. Referring to the results of Comparative Example 3, it can be confirmed that the thermal properties of the material are significantly changed according to the binding positions of the two substituents (deuterium-substituted carbazole and triazine ring) on the dibenzofuran or dibenzothiophene parent nucleus, showing different physical properties. Specifically, when the two substituents are para-bonded with respect to the parent nucleus as in Comparative Example 3, the sublimation temperature is significantly increased. Therefore, when manufacturing an organic light-emitting device, problems are likely to be caused by high temperature during the evaporation process. For this reason, it can be confirmed that the physical properties of Comparative Example 3 are inferior overall compared to Examples 1 to 9.

[0230] The compounds of Comparative Examples 4 and 5 are cases where L1 in Chemical Formula 1 is a single bond and L2 is a heteroaryl (dibenzofuran or dibenzothiophene). In such a structure, the energy electron cloud exhibits an extremely separated form, and the LUMO electron cloud is long and widely distributed. Therefore, Comparative Examples 4 and 5 show inferior lifetime characteristics compared to the Examples.

[0231] Examples 10 to 13 and Comparative Examples 6 to 10 are device examples using two hosts in the light-emitting layer. Even when two hosts are used in the light-emitting layer, it can be confirmed that the devices of Examples 10 to 13 using the compounds of the present invention have higher efficiency, especially significantly improved lifetime characteristics, compared to the devices of Comparative Examples 6 to 10.

[0232] Therefore, from the results of Table 1 above, it can be confirmed that when the compound of Chemical Formula 1 is used as the host of an organic light-emitting device, it exhibits characteristics of low voltage, high efficiency, and long lifetime.

[0233] [Symbol Explanation]

[0234] 1: Substrate 2: Anode

[0235] 3: Organic layer 4: Cathode

[0236] 5: Hole injection layer 6: Hole transport layer

[0237] 7: Electron blocking layer 8: Light-emitting layer

[0238] 9: Hole blocking layer 10: Electron transport layer

[0239] 11: Electron injection layer 12: Electron injection and transport layer.

Claims

1. A compound represented by the following Chemical Formula 1: [Chemical Formula 1] In the Chemical Formula 1, Y is O or S, D is deuterium, n and m are each independently an integer from 0 to 3, p and q are each independently an integer from 1 to 4, R1 and R2 are each independently hydrogen; deuterium; substituted or unsubstituted C 6-24 aryl; or substituted or unsubstituted C containing any one or more selected from N, O, and S 2-24 heteroaryl, However, at least one of R1 and R2 is deuterium; C substituted with one or more deuteriums 6-24 Aryl; or C substituted with one or more deuteriums containing any one or more selected from N, O and S 2-24 heteroaryl, L1 is a single bond; a substituted or unsubstituted C 6-24 arylene; or a substituted or unsubstituted C containing any one or more selected from N, O, and S 2-24 heteroarylene, L2 is a substituted or unsubstituted C 6-24 arylene; or a substituted or unsubstituted C 2-24 heteroarylene containing any one or more selected from N, O and S, However, when L1 is a single bond, L2 is a substituted or unsubstituted C 6-24 arylene group Ar1 and Ar2 are each independently substituted or unsubstituted C 6-24 Aryl; or substituted or unsubstituted C containing any one or more selected from N, O and S 2-24 Heteroaryl.

2. The compound according to claim 1, wherein R1 and R2 are each independently hydrogen, deuterium, a phenyl group which is substituted or unsubstituted with one or more deuteriums, a biphenyl group which is substituted or unsubstituted with one or more deuteriums, or a terphenyl group which is substituted or unsubstituted with one or more deuteriums.

3. The compound according to claim 1, wherein L1 is a single bond, a phenylene group, a biphenyldiyl group, a terphenyldiyl group, a naphthalenediyl group, a dibenzofurandiyl group or a dibenzothiophenediyl group, the L1 is unsubstituted or substituted with one or more deuteriums.

4. The compound according to claim 1, wherein L2 is a phenylene group, a biphenyldiyl group, a terphenyldiyl group, an anthracenediyl group, a triphenylenediyl group, a dimethylfluorenediyl group, a dibenzofurandiyl group or a dibenzothiophenediyl group, the L2 is unsubstituted or substituted with one or more deuteriums.

5. The compound according to claim 1, wherein Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, a dimethylfluorenyl group, a dibenzofuranyl group or a dibenzothiophenyl group, the Ar1 and Ar2 are each independently unsubstituted or substituted with one or more deuteriums.

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

7. An organic light-emitting device, wherein: Including: A first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound according to any one of claims 1 to 6.

8. The organic light emitting device according to claim 7, wherein: The organic layer containing the compound is a light-emitting layer.

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