New Compounds and Organic Light-Emitting Devices Containing the Same

Abstract

The present disclosure relates to novel compounds and organic light emitting devices comprising the same.

Description

Technical Field

[0001] Cross - Reference to Related Applications

[0002] This application claims the benefit of Korean Patent Application No. 10-2021-0030417, filed with the Korean Intellectual Property Office on Mar. 8, 2021, the disclosure of which is incorporated herein by reference in its entirety.

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

[0004] Generally, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic materials. Organic light-emitting devices using the organic light-emitting phenomenon have characteristics such as wide viewing angles, excellent contrast ratios, fast response times, 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 often has a multilayer structure including different materials to improve the efficiency and stability of the organic light-emitting device. For example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of the organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode into the organic material layer. When the injected holes and electrons meet each other, excitons are formed, and light is emitted when the excitons fall back to the ground state again.

[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 0001) Korean Unexamined Patent Publication No. 10-2000-0051826 (Patent Document 0002) U.S. Patent Publication No. 2007-0196692

[0010] (Patent Document 0003) Korean Unexamined Patent Publication No. 10-2017-0048159 (Patent Document 0004) U.S. Patent No. 6821643 Summary of the Invention

[0011] Technical Problem

[0012] The present disclosure relates to novel compounds and organic light-emitting devices including the same.

[0013] Technical Solution

[0014] In the present disclosure, compounds represented by the following Chemical Formula 1 or 2 are provided:

[0015] [Chemical Formula 1]

[0016]

[0017] [Chemical Formula 2]

[0018]

[0019] In Chemical Formula 1 or 2,

[0020] R1 to R4 are each independently hydrogen or deuterium,

[0021] n1 to n4 are integers from 1 to 4,

[0022] L1 and L2 are each independently a direct bond, or a substituted or unsubstituted C 6-60 arylene, and

[0023] Ar1 and Ar2 are each independently a substituent represented by the following Chemical Formula 3,

[0024] [Chemical Formula 3]

[0025]

[0026] In Chemical Formula 3,

[0027] X1 to X5 are each independently N or C(R5), where at least two of X1 to X5 are N, and

[0028] each R5 is independently hydrogen; deuterium; a substituted or unsubstituted C 1-20 alkyl; a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C containing at least one heteroatom selected from N, O, and S 2-60 heteroaryl, or two adjacent R5s combine to form a benzene ring.

[0029] In addition, an organic light-emitting device is provided, 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 of the organic material layers contains at least one of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

[0030] Advantageous Effects

[0031] The compound represented by Chemical Formula 1 or Chemical Formula 2 can be used as a material for an organic material layer of an organic light-emitting device, and can improve the efficiency, low driving voltage, and / or lifetime of the organic light-emitting device. In particular, the compound represented by Chemical Formula 1 can be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection. BRIEF DESCRIPTION OF THE DRAWINGS

[0032] 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.

[0033] 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, a light-emitting layer 7, an electron transport and injection layer 8, and a cathode 4 is shown.

[0034] 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 9, a light-emitting layer 7, a hole blocking layer 10, an electron transport and injection layer 8, and a cathode 4 is shown. DETAILED DESCRIPTION

[0035] Hereinafter, embodiments of the present disclosure will be described in more detail to facilitate understanding of the present invention.

[0036] As used herein, the symbol or means a bond connected to another substituent.

[0037] 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 cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; 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; and a heterocyclic group containing at least one of N, O, and S atoms, or unsubstituted or substituted with two or more substituents selected from the above-exemplified substituents connected to each other. 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.

[0038] In the present disclosure, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group may be a group having the following structural formula, but is not limited thereto.

[0039]

[0040] In the present disclosure, the ester group may have a structure in which the oxygen of the ester group is substituted by 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 group having the following structural formula, but is not limited thereto.

[0041]

[0042] 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 group having the following structural formula, but is not limited thereto.

[0043]

[0044] In the present disclosure, the silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but is not limited thereto.

[0045] In the present disclosure, the boron group specifically includes trimethylboron, triethylboron, tert-butyldimethylboron, triphenylboron, phenylboron, etc., but is not limited thereto.

[0046] In the present disclosure, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

[0047] In the present disclosure, the alkyl group may be straight-chain or branched-chain, and the number of its carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited thereto.

[0048] In the present disclosure, the alkenyl may be linear or branched, and there is no particular limitation on the number of carbon atoms thereof, but it is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl is 2 to 6. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylethenyl-1-yl, 2-phenylethenyl-1-yl, 2,2-diphenylethenyl-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethenyl-1-yl, 2,2-bis(diphenyl-1-yl)ethenyl-1-yl, stilbenyl, styryl, etc., but are not limited thereto.

[0049] In the present disclosure, the cycloalkyl has no particular limitation, but the number of carbon atoms thereof is preferably 3 to 60. According to one embodiment, the number of carbon atoms of the cycloalkyl is 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl is 3 to 20. According to another embodiment, the number of carbon atoms of the cycloalkyl is 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0050] In the present disclosure, the aryl has no particular limitation, but the number of carbon atoms thereof is preferably 6 to 60, and it may be a monocyclic aryl or a polycyclic aryl. According to one embodiment, the number of carbon atoms of the aryl is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl is 6 to 20. Monocyclic aryls include phenyl, biphenyl, terphenyl, etc., but are not limited thereto. Polycyclic aryls include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, yl, fluorenyl, etc., but are not limited thereto.

[0051] In the present disclosure, the fluorenyl may be substituted, and two substituents may be bonded to each other to form a spiro ring structure. When the fluorenyl is substituted, etc. may be formed. However, the structure is not limited thereto.

[0052] In the present disclosure, the heterocyclic group is a heterocyclic group containing at least one heteroatom selected from O, N, Si, and S as a hetero element, and there is no particular limitation on the number of carbon atoms thereof, but it is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, azolyl, Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, iso azolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, etc., but not limited thereto.

[0053] In the present disclosure, the aryl in aralkyl, aralkenyl, alkylaryl, and arylamino is the same as the aforementioned examples of aryl. In the present disclosure, the alkyl in aralkyl, alkylaryl, and alkylamino is the same as the aforementioned examples of alkyl. In the present disclosure, the heteroaryl in heteroarylamine can apply the aforementioned description of heterocyclic group. In the present disclosure, the alkenyl in aralkenyl is the same as the aforementioned examples of alkenyl. In the present disclosure, the aforementioned description of aryl can be applied, with the difference that the arylene is a divalent group. In the present disclosure, the aforementioned description of heterocyclic group can be applied, with the difference that the heteroarylene is a divalent group. In the present disclosure, the aforementioned description of aryl or cycloalkyl 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 aforementioned description of heterocyclic group can be applied, with the difference that the heterocycle is not a monovalent group but is formed by combining two substituents.

[0054] (Compound)

[0055] In the present disclosure, a compound represented by the above Chemical Formula 1 or 2 is provided.

[0056] Preferably, Chemical Formula 1 can be represented by the following Chemical Formula 1-1, and Chemical Formula 2 can be represented by the following Chemical Formula 2-1:

[0057] [Chemical Formula 1-1]

[0058]

[0059] [Chemical Formula 2-1]

[0060]

[0061] In Chemical Formula 1-1 or 2-1,

[0062] L1, L2, Ar1, and Ar2 are as defined above.

[0063] Preferably, L1 and L2 are each independently a direct bond, a phenylene group, or a biphenyldiyl group.

[0064] Preferably, each of Ar1 and Ar2 is independently any one selected from the following:

[0065]

[0066] Among the above groups,

[0067] R5 is as defined above.

[0068] Preferably, each R5 is independently hydrogen; deuterium; methyl; tert-butyl; phenyl; biphenyl; terphenyl; naphthyl; pyridyl; furyl or thienyl, or two adjacent R5s combine to form a benzene ring, and the phenyl, biphenyl, terphenyl, naphthyl, pyridyl, furyl or thienyl is each independently unsubstituted or substituted with deuterium, methyl or tert-butyl.

[0069] Preferably, each of Ar1 and Ar2 is independently any one selected from the following:

[0070]

[0071]

[0072] Representative examples of the compounds represented by Chemical Formula 1 or 2 are as follows:

[0073]

[0074]

[0075]

[0076]

[0077]

[0078] In addition, methods for preparing the compounds represented by Chemical Formula 1 or 2 are provided, as shown in Reaction Schemes 1 to 4 below.

[0079] [Reaction Scheme 1]

[0080]

[0081] [Reaction Scheme 2]

[0082]

[0083] [Reaction Scheme 3]

[0084]

[0085] [Reaction Scheme 4]

[0086]

[0087] In Reaction Schemes 1 to 4, each L is independently L1 or L2; each Ar is independently Ar1 or Ar2; each R is independently any one of R1 to R4; and each n is independently any one of n1 to n4. In addition, L1, L2, Ar1, Ar2, R1 to R4, and n1 to n4 are as defined above, X is a halogen, preferably bromine or chlorine.

[0088] (Organic light-emitting device)

[0089] In addition, according to another aspect of the present disclosure, there is provided an organic light-emitting device including at least one of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2. As an example, there is provided 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 of the organic material layers includes at least one of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2.

[0090] The organic material layer of the organic light-emitting device of the present disclosure may have a single-layer structure, or it may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present disclosure may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic material layers.

[0091] In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may include at least one of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2.

[0092] In addition, the organic material layer may include a light-emitting layer, and the light-emitting layer may include at least one of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2.

[0093] In addition, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include at least one of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2.

[0094] In addition, the electron transport layer, the electron injection layer, or the electron transport and injection layer may include at least one of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2.

[0095] The organic material layer may include an electron blocking layer, and the electron blocking layer is included between the anode and the light-emitting layer. The electron blocking layer may contain at least one of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2.

[0096] In addition, the organic material layer may include a light-emitting layer and an electron transport layer, and the electron transport layer may contain at least one of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2.

[0097] The organic material layer may include a hole blocking layer, and the hole blocking layer is included between the cathode and the light-emitting layer. The hole blocking layer is used to improve the efficiency of the organic light-emitting device by suppressing the transfer of holes injected from the anode to the cathode without recombination in the light-emitting layer. The hole blocking layer may contain at least one of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2.

[0098] Preferably, the organic material layer is an electron transport layer, an electron injection layer, or an electron transport and injection layer.

[0099] Preferably, the electron transport layer, the electron injection layer, or the electron transport and injection layer may further contain a compound represented by the following Chemical Formula 4:

[0100] [Chemical Formula 4]

[0101]

[0102] 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, the structure of an organic light-emitting device according to an embodiment of the present disclosure is shown in Figures 1 to 3 is shown.

[0103] 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. In such a structure, at least one of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2 may be included in the light-emitting layer.

[0104] 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, a light-emitting layer 7, an electron transport and injection layer 8, and a cathode 4 is shown. In such a structure, at least one of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2 may be included in at least one of the hole injection layer, the hole transport layer, the light-emitting layer, and the electron transport and injection layer.

[0105] 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 9, a light emitting layer 7, a hole blocking layer 10, an electron transport and injection layer 8, and a cathode 4 is shown. In such a structure, at least one of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 may be included in at least one layer among the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, and the electron transport and injection layer.

[0106] The organic light emitting device according to the present disclosure can be manufactured using materials and methods known in the art, except that at least one layer of the organic material layers includes at least one of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2. 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.

[0107] For example, the organic light emitting device according to the present disclosure can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light emitting device can be manufactured by: depositing a metal, a conductive metal oxide, or an alloy thereof on 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 a method, the 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.

[0108] In addition, when manufacturing the organic light emitting device, at least one of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 can be formed into an organic material layer by a solution coating method as well as a vacuum deposition method. Herein, 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.

[0109] In addition to such a method, the 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.

[0110] For example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

[0111] As an anode material, a material with a large work function is 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 their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and so on, but not limited thereto.

[0112] As a cathode material, a material with a small work function is 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 their alloys; multilayer structure materials such as LiF / Al or LiO2 / Al; and so on, but not limited thereto.

[0113] The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, thus having the effect of injecting holes into the anode and an excellent hole injection effect on the light-emitting layer or light-emitting material, preventing excitons generated in the light-emitting layer from moving to the electron injection layer or electron injection material, and having excellent 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, anthraquinone, conductive polymers based on polyaniline and polythiophene, etc., but not limited thereto.

[0114] In addition, 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 with a large hole mobility, which can receive holes from the anode or 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 part and a non-conjugated part coexist, etc., but not limited thereto.

[0115] The light-emitting material is suitably a material that can emit light in the visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer respectively to combine them and has good quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include tris(8-hydroxyquinoline)aluminum (Alq3); carbazole-based compounds; distyryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; based on benzo Oxazoles, benzothiazole-based and benzimidazole-based compounds; polymers based on poly(phenylene vinylene) (PPV); spiro compounds; polyfluorene; rubrene; and the like, but not limited thereto.

[0116] In addition, the light-emitting layer may include a host material and a dopant material. The host material may be a fused aromatic ring derivative or a heterocyclic compound. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc. Examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but not limited thereto.

[0117] The dopant material includes 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 which is substituted or unsubstituted, and examples thereof include pyrene, anthracene, , diindenopyrene, etc. having an arylamino group. 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 not limited thereto. In addition, the metal complex includes iridium complexes, platinum complexes, etc., but not limited thereto.

[0118] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport material used is preferably a material that can well receive electrons from the cathode, transfer the electrons to the light-emitting layer, and has a large electron mobility. Specifically, examples thereof may include: an Al complex of 8-hydroxyquinoline; a complex containing Alq3; an organic radical compound; a hydroxyflavone-metal complex; and the like, but not limited thereto. The electron transport layer can be used together with any desired cathode material as used according to the related art. In particular, suitable examples of the cathode material are typical materials having a low work function and 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.

[0119] The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound that has the ability to transport electrons, has an effect of injecting electrons from the cathode, and 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 is also excellent in the ability to form a thin film. Specific examples thereof include: fluorenone, anthraquinodimethane, biphenylenequinone, thiopyran dioxide, oxazoles, Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorene methane, anthrone, etc., and their derivatives; metal complex compounds; nitrogen-containing 5-membered ring derivatives; etc., but not limited thereto.

[0120] Examples of metal complex 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), chloro gallium bis(2-methyl-8-quinoline), gallium bis(2-methyl-8-quinoline)(o-cresol), aluminum bis(2-methyl-8-quinoline)(1-naphthol), gallium bis(2-methyl-8-quinoline)(2-naphthol), etc., but not limited thereto.

[0121] Depending on the materials used, the organic light-emitting device according to the present disclosure can be a front emission type, a back emission type, or a double-sided emission type.

[0122] In addition, in addition to the organic light-emitting device, the compounds according to the present disclosure can also be included in organic solar cells or organic transistors.

[0123] The preparation of the compound represented by Chemical Formula 1 or Chemical Formula 2 and the organic light-emitting device containing the same will be described in detail in the following examples. However, these examples are presented for illustrative purposes only and are not intended to limit the scope of the present disclosure.

[0124] [Examples]

[0125] Example 1: Preparation of Compound E1

[0126]

[0127] Under a nitrogen atmosphere, E1-A (20 g, 64.1 mmol) and E1-B (55.8 g, 128.2 mmol) were added to tetrahydrofuran (400 ml), and the mixture was stirred and refluxed. Then, potassium carbonate (26.6 g, 192.3 mmol) was dissolved in water (27 ml) and then added thereto. Thereafter, it was stirred well, and then tetrakis(triphenylphosphine)palladium (2.2 g, 1.9 mmol) was added. After reacting for 1 hour, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was redissolved in chloroform (20 times, 986 mL) and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to prepare Compound E1 (32.5 g, 66%) in the form of a white solid.

[0128] MS: [M+H] + = 769

[0129] Example 2: Preparation of Compound E2

[0130]

[0131] Compound E2 was prepared in the same manner as in Example 1, except that the respective starting materials were used as in the above reaction scheme.

[0132] MS: [M+H] + = 767

[0133] Example 3: Preparation of Compound E3

[0134]

[0135] Compound E3 was prepared in the same manner as in Example 1, except that the respective starting materials were used as in the above reaction scheme.

[0136] MS: [M+H] + = 715

[0137] Example 4: Preparation of Compound E4

[0138]

[0139] Compound E4 was prepared in the same manner as in Example 1, except that the respective starting materials were used as in the above reaction scheme.

[0140] MS: [M+H] + = 615

[0141] Example 5: Preparation of Compound E5

[0142]

[0143] Compound E5 was prepared in the same manner as in Example 1, except that the respective starting materials were used as in the above reaction scheme.

[0144] MS: [M+H] + = 619

[0145] Example 6: Preparation of Compound E6

[0146]

[0147] Compound E6 was prepared in the same manner as in Example 1, except that the respective starting materials were used as in the above reaction scheme.

[0148] MS: [M+H] + = 715

[0149] Example 7: Preparation of Compound E7

[0150]

[0151] Compound E7 was prepared in the same manner as in Example 1, except that the respective starting materials were used as in the above reaction scheme.

[0152] MS: [M+H] + = 919

[0153] Example 8: Preparation of Compound E8

[0154]

[0155] Under a nitrogen atmosphere, E8-A (20 g, 47.6 mmol) and E8-B (28 g, 47.6 mmol) were added to 1,4-d ane (400 ml), and the mixture was stirred and refluxed. Then, tripotassium phosphate (30.3 g, 142.9 mmol) was dissolved in water (30 ml) and then added thereto. Thereafter, it was stirred well, and then dibenzylideneacetone palladium (0.8 g, 1.4 mmol) and tricyclohexylphosphine (0.8 g, 2.9 mmol) were added. After reacting for 5 hours, it was cooled to room temperature, and the resulting solid was filtered. The resulting solid was redissolved in chloroform (30-fold, 1207 mL) and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare Compound E8 (6 g, 15%) in the form of a white solid.

[0156] MS: [M+H] + = 845

[0157] Example 9: Preparation of Compound E9

[0158]

[0159] Compound E9 was prepared in the same manner as in Example 8, except that the respective starting materials were used as in the above reaction scheme.

[0160] MS: [M+H] + = 769

[0161] Example 10: Preparation of Compound E10

[0162]

[0163] Compound E10 was prepared in the same manner as in Example 8, except that the respective starting materials were used as in the above reaction scheme.

[0164] MS: [M+H] + = 843

[0165] Example 11: Preparation of Compound E11

[0166]

[0167] Compound E11 was prepared in the same manner as in Example 1, except that the respective starting materials were used as in the above reaction scheme.

[0168] MS: [M+H] + = 769

[0169] Example 12: Preparation of Compound E12

[0170]

[0171] Compound E12 was prepared in the same manner as in Example 1, except that the respective starting materials were used as in the above reaction scheme.

[0172] MS: [M+H] + = 715

[0173] Example 13: Preparation of Compound E13

[0174]

[0175] Compound E13 was prepared in the same manner as in Example 1, except that the respective starting materials were used as in the above reaction scheme.

[0176] MS: [M+H] + = 795

[0177] Example 14: Preparation of Compound E14

[0178]

[0179] Compound E14 was prepared in the same manner as in Example 1, except that the respective starting materials were used as in the above reaction scheme.

[0180] MS: [M+H] + = 869

[0181] Example 15: Preparation of Compound E15

[0182]

[0183] Compound E15 was prepared in the same manner as in Example 1, except that the respective starting materials were used as in the above reaction scheme.

[0184] MS: [M+H] + = 919

[0185] Example 16: Preparation of Compound E16

[0186]

[0187] Compound E16 was prepared in the same manner as in Example 8, except that the respective starting materials were used as in the above reaction scheme.

[0188] MS: [M+H] + = 768

[0189] Example 17: Preparation of Compound E17

[0190]

[0191] Compound E17 was prepared in the same manner as in Example 8, except that the respective starting materials were used as in the above reaction scheme.

[0192] MS: [M+H] + = 845

[0193] Example 18: Preparation of Compound E18

[0194]

[0195] Compound E18 was prepared in the same manner as in Example 8, except that the respective starting materials were used as in the above reaction scheme.

[0196] MS: [M+H] + = 775

[0197] Example 19: Preparation of Compound E19

[0198]

[0199] Compound E19 was prepared in the same manner as in Example 1, except that the respective starting materials were used as in the above reaction scheme.

[0200] MS: [M+H] + = 921

[0201] Example 20: Preparation of Compound E20

[0202]

[0203] Compound E20 was prepared in the same manner as in Example 1, except that the respective starting materials were used as in the above reaction scheme.

[0204] MS: [M+H] + = 919

[0205] [Experimental Example]

[0206] Experimental Example 1

[0207] A glass substrate with ITO (indium tin oxide) coated thereon as a thin film with a thickness of was placed in distilled water in which a detergent was dissolved and ultrasonically cleaned. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as the distilled water. After cleaning the ITO for 30 minutes, ultrasonic cleaning was repeated twice for 10 minutes using distilled water. After cleaning was completed with distilled water, the substrate was ultrasonically cleaned with isopropyl alcohol, acetone, and methanol solvents, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned with oxygen plasma for 5 minutes and then transferred to a vacuum depositor.

[0208] On the prepared ITO transparent electrode, the following compound HI-A was thermally vacuum deposited to a thickness of to form a hole injection layer. On the hole injection layer, hexanitrile hexaazatriphenylene (HAT, ) having the following formula and the following compound HT-A were sequentially vacuum deposited to form a hole transport layer.

[0209] Then, the following compounds BH and BD were vacuum deposited on the hole transport layer at a weight ratio of 25:1 to a thickness of to form a light-emitting layer.

[0210] The compound E1 of Example 1 and the following compound LiQ (lithium quinolate) were vacuum deposited on the light-emitting layer at a weight ratio of 1:1 to a thickness of to form an electron transport and injection layer. On the electron transport and injection layer, lithium fluoride (LiF) and aluminum were sequentially deposited to thicknesses of and to form a cathode.

[0211]

[0212] During the above process, the deposition rate of the organic material was maintained at to The deposition rate of lithium fluoride of the cathode was maintained at and maintain the deposition rate of aluminum at In addition, maintain the degree of vacuum during deposition at 1×10 -7 Torr to 5×10 -8 Torr, thereby manufacturing an organic light-emitting device.

[0213] Experimental Examples 2 to 20

[0214] Manufacture an organic light-emitting device in the same manner as in Experimental Example 1, except that the compound shown in Table 1 is used instead of the compound of Example 1.

[0215] Comparative Experimental Examples 1 to 19

[0216] Manufacture an organic light-emitting device in the same manner as in Experimental Example 1, except that the compound shown in Table 1 is used instead of the compound of Example 1. At this time, the compounds ET-1 to ET-19 listed in Table 1 are as follows.

[0217]

[0218] For the organic light-emitting devices prepared in the experimental examples and comparative experimental examples, measure the driving voltage, luminous efficiency, and chromaticity coordinates at a current density of 10 mA / cm 2 . In addition, measure T 90 , where the T 90 is the time required for the initial luminance to decrease to 90% at a current density of 20 mA / cm 2 . The results are shown in Table 1 below.

[0219] [Table 1]

[0220]

[0221]

[0222] As shown in Table 1, the compound represented by Chemical Formula 1 or 2 of the present disclosure can be used in the organic material layer capable of simultaneously performing electron transport and electron injection in an organic light-emitting device.

[0223] When comparing Experimental Examples 1 to 20 and Comparative Experimental Examples 1 to 11 in Table 1, it is determined that the organic light-emitting device of the present disclosure containing the heterocyclic compound of Chemical Formula 1 or 2 has significantly superior efficiency and lifetime compared to the organic light-emitting device containing the compound in which the phenyl group substituted between Ar1 and Ar2 has less than four biphenyl groups.

[0224] When comparing Experimental Examples 1 to 20 in Table 1 with Comparative Experimental Examples 12 to 17, it was determined that the organic light-emitting device including the heterocyclic compound represented by Chemical Formula 1 or 2 of the present disclosure has significantly superior efficiency and lifetime compared to the organic light-emitting device including the compound in which the quaterphenyl is substituted at a substitution position different from that of the present disclosure.

[0225] When comparing Experimental Examples 1 to 20 in Table 1 with Comparative Experimental Example 18, it was determined that the organic light-emitting device including the heterocyclic compound represented by Chemical Formula 1 or 2 of the present disclosure has significantly superior efficiency and lifetime compared to the organic light-emitting device including the compound in which naphthalene is substituted between Ar1 and Ar2.

[0226] When comparing Experimental Examples 1 to 20 in Table 1 with Comparative Experimental Example 19, it was determined that the organic light-emitting device including the heterocyclic compound represented by Chemical Formula 1 or 2 of the present disclosure has significantly superior efficiency and lifetime compared to the organic light-emitting device including the compound in which a heteroaryl is further substituted to the sub-quaterphenyl.

[0227] [Description of Reference Numerals]

[0228] 1: Substrate 2: Anode

[0229] 3: Light-emitting layer 4: Cathode

[0230] 5: Hole injection layer 6: Hole transport layer

[0231] 7: Light-emitting layer 8: Electron transport and injection layer

[0232] 9: Electron blocking layer 10: Hole blocking layer

Claims

1. A compound represented by the following Chemical Formula 1 or 2: [Chemical Formula 1] [Chemical Formula 2] In Chemical Formula 1 or 2, R1 to R4 are each independently hydrogen or deuterium, n1 to n4 are integers from 1 to 4, L1 and L2 are each independently a direct bond, a phenylene group, or a biphenyldiyl group, and Ar1 and Ar2 are each independently a substituent represented by the following Chemical Formula 3, [Chemical Formula 3] In Chemical Formula 3, X1 to X5 are each independently N or CR5, where at least two of X1 to X5 are N, and each R5 is independently hydrogen, deuterium, methyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, furyl, or thienyl, or two adjacent R5s combine to form a benzene ring; and the phenyl, biphenyl, terphenyl, naphthyl, pyridyl, furyl, or thienyl is each independently unsubstituted or substituted with deuterium, methyl, or tert-butyl.

2. The compound according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 1-1, and Chemical Formula 2 is represented by the following Chemical Formula 2-1: [Chemical Formula 1-1] [Chemical Formula 2-1] In Chemical Formula 1-1 or 2-1, L1, L2, Ar1, and Ar2 are as defined in claim 1.

3. The compound according to claim 1, wherein Ar1 and Ar2 are each independently any one selected from the following: In the above groups, R5 is as defined in claim 1.

4. The compound according to claim 1, wherein Ar1 and Ar2 are each independently any one selected from the following:

5. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 or 2 is any one selected from the following compounds:

6. An organic light emitting device, comprising: A first electrode; A second electrode disposed opposite to the first electrode; And one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound according to any one of claims 1 to 5.

7. The organic light-emitting device according to claim 6, wherein the organic material layer is an electron transport layer, an electron injection layer, or an electron transport and injection layer.

8. The organic light-emitting device according to claim 7, wherein the electron transport layer, the electron injection layer, or the electron transport and injection layer further contains a compound represented by the following Chemical Formula 4: [Chemical Formula 4]

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