Heterocyclic compound and organic light-emitting device containing the same

Abstract

The present disclosure provides heterocyclic compounds and organic light-emitting devices including the same.

Description

Technical Field

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of Korean Patent Application No. 10-2018-0114411 filed on September 21, 2018, and Korean Patent Application No. 10-2019-0115650 filed on September 19, 2019, in the Korean Intellectual Property Office, each of which is incorporated herein by reference in its entirety.

[0003] The present disclosure relates to heterocyclic 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 angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed, and therefore 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 between the anode and the cathode. The organic material layer generally has a multilayer structure including different materials to improve the efficiency and stability of the organic light-emitting device, and for example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of the organic light-emitting device, if a voltage is applied between two electrodes, holes are injected from the anode into the organic material layer and electrons are injected from the cathode into the organic material layer, and when the injected holes and electrons meet each other, excitons are formed, and light is emitted when the excitons fall to the ground state again.

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

[0007] [Prior art literature]

[0008] [Patent Document]

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

[0010] Technical issues

[0011] An object of the present disclosure is to provide a heterocyclic compound and an organic light-emitting device including the same.

[0012] Technical Solution

[0013] In one aspect of the present disclosure, a compound represented by the following Chemical Formula 1 is provided:

[0014] [Chemical formula 1]

[0015]

[0016] Wherein, in Chemical Formula 1,

[0017] X is O or S,

[0018] Y1, Y2 and Y3 are each independently CH; or N, provided that at least one of Y1, Y2 and Y3 is N,

[0019] L1 and L2 are each independently a direct bond; a substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing at least one heteroatom selected from N, O and S 5-60 Heteroarylene,

[0020] Ar1 is substituted or unsubstituted C 6-60 Aryl,

[0021] Ar2 and Ar3 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing at least one heteroatom selected from N, O and S 5-60 heteroaryl;

[0022] Provided that when Ar1, Ar2 and Ar3 are all substituted or unsubstituted C 6-60 In the case of an aryl group, any one of Ar1, Ar2 and Ar3 is substituted with 4 or more deuteriums,

[0023] Each R1 is independently hydrogen; deuterium; halogen, or substituted or unsubstituted C 1-60 alkyl,

[0024] Each R2 is independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C 1-60 Alkyl; substituted or unsubstituted C 1-60 Alkoxy; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 1-60 Haloalkyl; substituted or unsubstituted C 1-60 Haloalkoxy; substituted or unsubstituted C 6-60 Arylamine; substituted or unsubstituted C 1-60 Alkylamino; C 1-60 trifluoroalkyl; C 1-60 trifluoroalkoxy; substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing at least one of N, O and S 5-60 heteroaryl, the R2 may be bonded to the carbon atom of carbazole to form a condensed ring,

[0025] m is an integer from 0 to 3,

[0026] n is an integer from 0 to 6, and

[0027] l is 1 or 2.

[0028] In another aspect of the present invention, an organic light-emitting device is provided, which includes: a first electrode; a second electrode arranged opposite to the first electrode; and one or more organic material layers arranged between the first electrode and the second electrode, wherein one or more of the organic material layers contains the compound of the above-mentioned present disclosure.

[0029] Beneficial Effects

[0030] The compound represented by Chemical Formula 1 can be used as a material of an organic material layer of an organic light-emitting device, and can improve efficiency, achieve low driving voltage and / or improve life characteristics in the organic light-emitting device. In particular, the compound represented by Chemical Formula 1 can be used as a hole injection material, a hole transport material, a hole injection and transport material, a light-emitting material, an electron transport material or an electron injection material. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] 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.

[0032] 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 layer 8 and a cathode 4 is shown. Specific implementation plan

[0033] Hereinafter, embodiments of the present disclosure will be described in more detail to help understanding of the present invention.

[0034] One embodiment of the present invention provides a compound represented by the following Chemical Formula 1:

[0035] [Chemical formula 1]

[0036]

[0037] Wherein, in Chemical Formula 1,

[0038] X is O or S,

[0039] Y1, Y2 and Y3 are each independently CH; or N, provided that at least one of Y1, Y2 and Y3 is N,

[0040] L1 and L2 are each independently a direct bond; a substituted or unsubstituted C 6-60or a substituted or unsubstituted C containing at least one heteroatom selected from N, O and S 5-60 Heteroarylene,

[0041] Ar1 is substituted or unsubstituted C 6-60 Aryl,

[0042] Ar2 and Ar3 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing at least one heteroatom selected from N, O and S 5-60 heteroaryl;

[0043] Provided that when Ar1, Ar2 and Ar3 are all substituted or unsubstituted C 6-60 In the case of an aryl group, any one of Ar1, Ar2 and Ar3 is substituted with 4 or more deuterium, wherein Ar1, Ar2 and Ar3 are all substituted or unsubstituted C 6-60 Aryl, which means that they are the same or different substituted or unsubstituted C 6-60 The case of aromatic groups.

[0044] Each R1 is independently hydrogen; deuterium; halogen, or substituted or unsubstituted C 1-60 alkyl,

[0045] Each R2 is independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C 1-60 Alkyl; substituted or unsubstituted C 1-60 Alkoxy; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 1-60 Haloalkyl; substituted or unsubstituted C 1-60 Haloalkoxy; substituted or unsubstituted C 6-60 Arylamine; substituted or unsubstituted C 1-60 Alkylamino; C 1-60 trifluoroalkyl; C 1-60 trifluoroalkoxy; substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing at least one of N, O and S 5-60 heteroaryl, the R2 may be bonded to the carbon atom of carbazole to form a condensed ring,

[0046] m is an integer from 0 to 3,

[0047] n is an integer from 0 to 6, and

[0048] l is 1 or 2.

[0049] In the above, when Ar1, Ar2 and Ar3 are substituted or unsubstituted C6-60 Aryl means that Ar1, Ar2 and Ar3 are the same or different substituted or unsubstituted C 6-60 The case of aromatic groups.

[0050] As used herein, the symbol and It refers to the bond to another substituent.

[0051] As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the following: deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkylthio group; arylthio group; alkylsulfonyl group; arylsulfonyl group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamino group; aralkylamino group; heteroarylamino group; arylamino group; arylphosphino group; or a heterocyclic group containing at least one of N, O and S atoms, or unsubstituted or substituted with a substituent in which two or more substituents are connected among the substituents exemplified above. For example, "a substituent in which two or more substituents are connected" can be a biphenyl group. That is, the biphenyl group can also be an aryl group, and it can be understood as a substituent in which two phenyl groups are connected.

[0052] In the present specification, the carbon number 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.

[0053]

[0054] In the present specification, the ester group may have a structure in which oxygen of the ester group may be substituted by a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a group having the following structural formula, but is not limited thereto.

[0055]

[0056] In the present specification, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25.

[0057] Specifically, the imide group may be a group having the following structural formula, but is not limited thereto.

[0058]

[0059] In the present specification, the silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but is not limited thereto.

[0060] In the present specification, the boryl group specifically includes a trimethylboryl group, a triethylboryl group, a tert-butyldimethylboryl group, a triphenylboryl group, and a phenylboryl group, but is not limited thereto.

[0061] In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

[0062] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof 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, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0063] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, phenyl group, styryl group, etc., but are not limited thereto.

[0064] In the present specification, the cycloalkyl group is not particularly limited, but the number of carbon atoms thereof is preferably 3 to 60. According to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to yet another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

[0065] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. As a monocyclic aryl group, the aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. Examples of polycyclic aryl groups include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, fluorenyl, etc., but are not limited thereto.

[0066] In the present specification, the fluorenyl group may be substituted, and two substituents may be connected to each other to form a spirocyclic structure. In the case where the fluorenyl group is substituted, Etc. However, the structure is not limited thereto.

[0067] In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl and the like, but are not limited thereto.

[0068] In this specification, the aryl in aralkyl, aralkenyl, alkylaryl and arylamine is the same as the example of the above-mentioned aryl. In this specification, the alkyl in aralkyl, alkylaryl and alkylamine is the same as the example of the above-mentioned alkyl. In this specification, the heteroaryl in heteroarylamine can apply the description of the above-mentioned heteroaryl. In this specification, the alkenyl in aralkenyl is the same as the example of the above-mentioned alkenyl. In this specification, the description of the above-mentioned aryl can be applied, except that the arylene is a divalent group. In this specification, the description of the above-mentioned heteroaryl can be applied, except that the heteroarylene is a divalent group. In this specification, the description of the above-mentioned aryl or cycloalkyl can be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In this specification, the description of the above-mentioned heteroaryl can be applied, except that the heterocycle is not a monovalent group but is formed by combining two substituents.

[0069] Preferably, the compound represented by Chemical Formula 1 may be any one selected from the compounds represented by the following Chemical Formulas 2 to 8:

[0070] [Chemical formula 2]

[0071]

[0072] [Chemical formula 3]

[0073]

[0074] [Chemical formula 4]

[0075]

[0076] [Chemical formula 5]

[0077]

[0078] [Chemical formula 6]

[0079]

[0080] [Chemical formula 7]

[0081]

[0082] [Chemical formula 8]

[0083]

[0084] Wherein, in Chemical Formulas 2 to 8,

[0085] X, Y1, Y2, Y3, L1, L2, Ar1, Ar2, Ar3, R1, R2, m and n are as defined above.

[0086] Preferably, L1 and L2 can each independently be a direct bond or any one selected from the following:

[0087]

[0088] Preferably, Ar1 can be any one selected from the following:

[0089]

[0090] In the above formula,

[0091] a is an integer from 0 to 4,

[0092] b is an integer from 0 to 5,

[0093] c is an integer from 0 to 7,

[0094] d is an integer from 0 to 9, and

[0095] e is an integer from 0 to 11.

[0096] Preferably, Ar1 is each independently unsubstituted or deuterium-substituted phenyl, biphenyl, naphthyl, phenanthryl or triphenylene.

[0097] Preferably, Ar2 and Ar3 may each independently be any one selected from the following:

[0098]

[0099] In the above formula,

[0100] a' is an integer from 0 to 4,

[0101] b' is an integer from 0 to 5,

[0102] c' is an integer from 0 to 7,

[0103] d' is an integer from 0 to 8,

[0104] e' is an integer from 0 to 9, and

[0105] f' is an integer from 0 to 11.

[0106] Preferably, each R1 may be independently hydrogen or deuterium, more preferably hydrogen.

[0107] Preferably, each R2 is independently hydrogen; deuterium; halogen; cyano; methoxy; trifluoromethyl; trifluoromethoxy; phenyl; pyridyl; isoquinolinyl; or any one of the following:

[0108]

[0109] In the above formula, two * are each connected to adjacent carbons of carbazole in Chemical Formula 1, and

[0110] The phenyl group may be substituted with any one selected from halogen, cyano, methoxy, trifluoromethyl and trifluoromethoxy.

[0111] Preferably, in the compound represented by Chemical Formula 1, at least one of L1, Ar2, and Ar3 may include at least one heteroatom selected from N, O, and S.

[0112] Preferably, the compound represented by Chemical Formula 1 may be any one selected from the following:

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150] The compound represented by Chemical Formula 1 according to the present disclosure has structural characteristics that it contains a carbazole-based substituent and a triazine (pyrimidine)-based substituent in one benzene ring of the core structure of dibenzofuran (dibenzothiophene) at the same time, and contains an aryl substituent in another benzene ring, and due to these characteristics, the compound can have improved thermal stability, and at the same time, can have high efficiency, low driving voltage, high brightness and long life. In particular, in the present disclosure, when Ar1, Ar2 and Ar3 are the same or different substituted or unsubstituted C 6-60When the heteroaryl group is substituted with a triazine having strong electronic properties, any one of Ar1, Ar2 and Ar3 is substituted with 4 or more deuteriums, which stabilizes the LUMO. Therefore, compared with an organic light-emitting device using a compound having a structure in which all the terminal Ar1, Ar2 and Ar3 are aryl groups and are not substituted with deuterium, the present disclosure can have improved long-life characteristics. In addition, since the heteroaryl group is substituted on the triazine having strong electronic properties, the balance between holes and electrons is appropriately balanced, which can be beneficial in terms of efficiency and life of the device.

[0151] The compound represented by Chemical Formula 1 can be prepared by the following reaction schemes 1-1 and 1-2.

[0152] [Reaction Scheme 1-1]

[0153]

[0154] [Reaction Scheme 1-2]

[0155]

[0156] In Reaction Schemes 1-1 and 1-2, X' is a halogen, preferably bromine or chlorine, and the remaining substituents are as defined above.

[0157] The above reaction is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactants, catalysts, etc. used for the reaction can be modified as known in the art. The above preparation method can be further implemented in the preparation example described below. In addition, when introducing multiple substituents, it can be achieved by repeating these steps (for example, in reaction scheme 1-1, multiple Ar1 introduction can be achieved by performing the first step several times. In this case, it is also possible to carry out together a protecting group known in the art and a deprotecting group reaction to introduce a desired structure).

[0158] Another embodiment of the present invention provides an organic light-emitting device, which includes the compound represented by Chemical Formula 1. As an example, 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 one or more layers of the organic material layers include the compound represented by Chemical Formula 1.

[0159] The organic material layer of the organic light-emitting device of the present disclosure may have a single-layer structure, or it may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present disclosure may have a structure including a hole injection layer, a hole transport layer, 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 layers.

[0160] In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer for simultaneous hole injection and transport, wherein the hole injection layer, the hole transport layer, or the layer for simultaneous hole injection and transport contains the compound represented by Chemical Formula 1.

[0161] In addition, the organic material layer may include a light emitting layer, wherein the light emitting layer includes the compound represented by Chemical Formula 1.

[0162] In addition, the organic material layer may include an electron transport layer or an electron injection layer, wherein the electron transport layer or the electron injection layer includes the compound represented by Chemical Formula 1.

[0163] In addition, the electron transport layer, the electron injection layer, and the layer for simultaneous electron injection and electron transport contain the compound represented by Chemical Formula 1. In particular, the compound represented by Chemical Formula 1 according to the present disclosure has excellent thermal stability, a deep HOMO level of 6.0 eV or higher, high triplet energy (ET) and hole stability. In addition, when the compound represented by Chemical Formula 1 is used as an organic material layer capable of simultaneous electron injection and electron transport, an n-type dopant used in the art can be mixed and used.

[0164] In addition, the organic material layer includes a light emitting layer and an electron transport layer, wherein the electron transport layer may include the compound represented by Chemical Formula 1.

[0165] 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, in Figure 1 and Figure 2 The structure of an organic light emitting device according to an embodiment of the present disclosure is shown in FIG.

[0166] 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 this structure, the compound represented by Chemical Formula 1 may be contained in the light emitting layer.

[0167] 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 layer 8, and a cathode 4 is shown. In this structure, the compound represented by Chemical Formula 1 may be contained in one or more of the hole injection layer, the hole transport layer, the light-emitting layer, and the electron transport layer.

[0168] The organic light-emitting device according to the present disclosure can be manufactured by materials and methods known in the art, except that one or more of the organic material layers contain the compound represented by Chemical Formula 1. In addition, when the organic light-emitting device includes multiple organic material layers, the organic material layers can be formed of the same or different materials.

[0169] For example, an organic light-emitting device according to the present disclosure can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting device can be manufactured by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate to form an anode using a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method, forming an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the anode, and then depositing a material that can be used as a cathode on the organic material layer. In addition to such a method, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0170] In addition, when manufacturing an organic light-emitting device, the compound represented by Chemical Formula 1 can be formed into an organic material layer by a solution coating method and a vacuum deposition method. Here, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0171] In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Publication WO 2003 / 012890). However, the manufacturing method is not limited thereto.

[0172] As an example, the first electrode is an anode and the second electrode is a cathode, or alternatively the first electrode is a cathode and the second electrode is an anode.

[0173] As the anode material, generally, it is preferred to use a material having a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of anode materials include metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, etc., but are not limited thereto.

[0174] As the cathode material, generally, it is preferred to use a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0175] The hole injection material is a layer for injecting holes from the electrode, and the hole injection material is preferably such a compound: it has the ability to transport holes, so as to have a hole injection effect in the anode and an excellent hole injection effect on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and the ability to form a thin film is excellent. 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 hole injection materials include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, conductive polymers based on polyaniline and based on polythiophene, etc., but are not limited thereto.

[0176] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and is suitably a material having a large mobility for holes, which can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers in which conjugated parts and non-conjugated parts exist simultaneously, etc., but are not limited thereto.

[0177] The light-emitting material is preferably a material that can receive holes and electrons respectively transferred from the hole transport layer and the electron transport layer, and combine the holes and electrons to emit light in the visible light region, and has good quantum efficiency for fluorescence or phosphorescence. Specific examples of the light-emitting material include 8-hydroxyquinoline aluminum complex (Alq3); carbazole-based compounds; diphenylethylene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo-based Compounds of oxazole, benzothiazole and benzimidazole; polymers based on poly(p-phenylenevinylene) (PPV); spiro compounds; polyfluorene; rubrene, etc., but are not limited thereto.

[0178] The light-emitting layer may include a host material and a dopant material. The host material may be a fused aromatic ring derivative, a heterocyclic compound, etc. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc. Examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0179] Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivatives are substituted or unsubstituted fused aromatic ring derivatives having an arylamino group, examples of which include pyrene, anthracene, Diindenopyrene, etc. The styrylamine compound is a compound in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, wherein one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino are substituted or unsubstituted. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but are not limited thereto. In addition, the metal complex includes iridium complex, platinum complex, etc., but are not limited thereto.

[0180] 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 is appropriately a material that can well receive electrons from the cathode and transport the electrons to the light-emitting layer, and has a large electron mobility. Specific examples of electron transport materials include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used with any desired cathode material used according to the relevant technology. In particular, suitable examples of cathode materials are typical materials with low work functions, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

[0181] The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound that has the ability to transport electrons, has an effect of injecting electrons from the cathode and an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents the excitons generated by the light-emitting layer from moving to the hole injection layer, and is also excellent in the ability to form a thin film. Specific examples of the electron injection layer include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, The examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, and their derivatives, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like.

[0182] The metal complex compounds include 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) chlorogallium, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0183] The organic light emitting device according to the present disclosure may be a front-side emission type, a rear-side emission type, or a double-side emission type according to the materials used.

[0184] Furthermore, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

[0185] The preparation of the compound represented by Chemical Formula 1 and an organic light-emitting device including 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.

[0186] <Preparation Example>

[0187] Preparation Example 1-1: Preparation of Intermediate Compound B

[0188]

[0189] Compound a-1 (4-iododibenzothiophene) (20 g, 96.73 mmol) was added to a dry round-bottom flask under a nitrogen atmosphere, and 500 ml of chloroform was then added thereto. Then, 2.5 eq of bromine (12.4 ml, 24.1 mmol) was added dropwise and reacted at room temperature for 12 hours. After the reaction was complete, the mixture was extracted with dichloromethane and sodium thiosulfate aqueous solution, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtered organic layer was concentrated under reduced pressure, and then crystallized from ethyl acetate and hexane to obtain white compound A1-1 (28 g, 75%, MS: [M+H] + =388).

[0190] Preparation Examples 1-2 to 1-8: Preparation of Intermediate Compound B

[0191] Intermediate Compound B was prepared in the same manner as the method for preparing Compound A1-1, except that Reactant A shown in the following Table 1 was used as a reactant instead of Compound a-1 (4-iododibenzothiophene) in Preparation Example 1-1.

[0192] [Table 1]

[0193]

[0194]

[0195] Preparation Example 2-1: Preparation of Intermediate Compound D

[0196]

[0197] Compound A1-1 (20 g, 51.41 mmol) and compound c-1 (phenylboronic acid) (6.27 g, 51.41 mmol) were dissolved in tetrahydrofuran (150 mL) under a nitrogen atmosphere, potassium carbonate (21.3 g, 154.2 mmol) was dissolved in water (50 mL) and added thereto, and tetrakis (triphenylphosphine) palladium (1.8 g, 1.54 mmol) was added, and the mixture was heated and stirred at 60° C. for 9 hours. The temperature was lowered to room temperature, and the reaction mixture was filtered, washed with water and ethanol and dried to prepare compound A2-1 (15.2 g, yield: 87%, MS: [M+H] + =338).

[0198] Preparation Examples 2-2 to 2-9: Preparation of Intermediate Compound D

[0199] Intermediate Compound D was prepared in the same manner as in Preparation Example 2-1, except that Intermediate Compound B and Intermediate Compound C shown in Table 2 below were used instead of Compound A1-1 and Compound c-1 (phenylboronic acid) in Preparation Example 2-1.

[0200] [Table 2]

[0201]

[0202]

[0203] Preparation Example 3-1: Preparation of Intermediate Compound F

[0204]

[0205] Under a nitrogen atmosphere, compound A2-1 (15 g, 44.22 mmol) and compound e-1 (9H-carbazole) (7.39 g, 44.22 mmol) were dissolved in xylene (150 mL), NaOtBu (6.4 g, 66.32 mmol) was added thereto, bis(tri-tert-butylphosphine)palladium (0) (0.7 g, 1.33 mmol) was added, and the mixture was heated and stirred for 12 hours. The temperature was lowered to room temperature, and the reaction mixture was filtered, washed with water and ethanol and dried to prepare compound A1-1 (13.9 g, yield: 74%, MS: [M+H] + =426).

[0206] Preparation Examples 3-2 to 3-10: Preparation of Intermediate Compound F

[0207] Intermediate Compound F was prepared in the same manner as in Preparation Example 3-1, except that Intermediate Compound D and Intermediate Compound E shown in Table 3 below were used instead of Compound A2-1 and Compound e-1 (phenylboronic acid) in Preparation Example 3-1.

[0208] [Table 3]

[0209]

[0210]

[0211]

[0212] Preparation Example 4-1: Preparation of Compound A1-4

[0213]

[0214] Under nitrogen atmosphere, in a dry round-bottom flask, compound A3-1 (14 g, 32.90 mmol) was dissolved in 150 mL THF, 1.6 M n-BuLi (26.73 mL, 42.77 mmol) was slowly added dropwise at -78 ° C, and the mixture was stirred at room temperature for 1 hour. Isopropyl borate (i-PrO) 3B (26.5 mL, 115.1 mmol) was added dropwise to the reaction mixture at -78 ° C, and then stirred at room temperature for 1 hour. After the reaction was completed, the mixture was extracted with aqueous ammonium chloride at room temperature, and the organic layer was dried with MgSO4, concentrated, and recrystallized from ethyl acetate to obtain compound A4-1. (10 g, yield: 65%, MS: [M+H] + =470)

[0215] Preparation Examples 4-2 to 4-10: Preparation of Intermediate Compound G

[0216] Intermediate Compound G was prepared in the same manner as in Preparation Example 4-1, except that Intermediate Compound F shown in the following Table 4 was used instead of Compound A3-1 in Preparation Example 4-1.

[0217] [Table 4]

[0218]

[0219]

[0220]

[0221] <Example>

[0222] Example 1: Preparation of Compound 1

[0223]

[0224] After compound A4-1 (15 g, 31.96 mmol) and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine (8.71 g, 31.96 mmol) were dissolved in THF (150 mL), potassium carbonate (13.3 g, 211.10 mmol) was added, and tetrakis (triphenylphosphine) palladium (1.1 g, 0.96 mmol) was added, and the mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature, and the water layer was separated and removed. The resultant was dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, recrystallized using ethyl acetate, filtered and dried to prepare compound 1 (15.7 g, yield: 74%, MS: [M+H] + =662).

[0225] Example 2: Preparation of Compound 2

[0226]

[0227] Compound 2 was prepared in the same manner as for the preparation of Compound 1, except that Compound A4-5 was used instead of Compound A4-1. (15.0 g, yield: 71%, MS: [M+H] + =662)

[0228] Example 3: Preparation of Compound 3

[0229]

[0230] Compound 3 was prepared in the same manner as for the preparation of compound 1, except that compound A4-3 was used instead of compound A4-1. (15.0 g, yield: 71%, MS: [M+H] + =667)

[0231] Example 4: Preparation of Compound 4

[0232]

[0233] Compound 4 was prepared in the same manner as for the preparation of compound 1, except that compound A4-2 was used instead of compound A4-1. (16.0 g, yield: 82%, MS: [M+H] + =827)

[0234] Example 5: Preparation of Compound 5

[0235]

[0236] Compound 5 was prepared in the same manner as for the method for preparing compound 1, except that compound A4-6 and 2-chloro-4-(phenanthren-2-yl)-6-(phenyl-d5)-1,3,5-triazine were used instead of compound A4-2 and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine. (16.0 g, yield: 82%, MS: [M+H] + =827)

[0237] Example 6: Preparation of Compound 6

[0238]

[0239] Compound 6 was prepared in the same manner as for the preparation of compound 1, except that compound A4-6 and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-(phenyl-d5)-1,3,5-triazine were used instead of compound A4-1 and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine. (17.8 g, yield: 74%, MS: [M+H] + =752)

[0240] Example 7: Preparation of Compound 7

[0241]

[0242] Compound 7 was prepared in the same manner as for the preparation of compound 1, except that 9-(4-chloro-6-(phenyl-d5)-1,3,5-triazine-2-yl)-9H-carbazole was used instead of 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine. (16.5 g, yield: 69%, MS: [M+H] + =751)

[0243] Example 8: Preparation of Compound 8

[0244]

[0245] Compound 8 was prepared in the same manner as the method for preparing compound 1, except that compound A4-5 and 2-chloro-4-(dibenzo[b,d]thiophene-4-yl)-6-(phenyl-d5)-1,3,5-triazine were used instead of compound A4-1 and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine. (18.9 g, yield: 77%, MS: [M+H] + =768)

[0246] Example 9: Preparation of Compound 9

[0247]

[0248] Compound 9 was prepared in the same manner as for the preparation of compound 1, except that compound A4-4 and 9-(4-chloro-6-(phenyl-d5)-1,3,5-triazine-2-yl)-9H-carbazole were used instead of compound A4-1 and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine. (14.8 g, yield: 65%, MS: [M+H] + =827)

[0249] Example 10: Preparation of Compound 10

[0250]

[0251] Compound 10 was prepared in the same manner as the method for preparing compound 1, except that compound A4-3 and 2-(8-chlorodibenzo[b,d]furan-1-yl)-4,6-diphenyl-1,3,5-triazine were used instead of compound A4-1 and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine. (18.3 g, yield: 70%, MS: [M+H] + =828)

[0252] Example 11: Preparation of Compound 11

[0253]

[0254] Compound 11 was prepared in the same manner as for the preparation of compound 1, except that compound B4-1 was used instead of compound A4-1. (16.2 g, yield: 76%, MS: [M+H] + =646)

[0255] Example 12: Preparation of Compound 12

[0256]

[0257] Compound 12 was prepared in the same manner as the method for preparing compound 1, except that compound B4-2 and 9-(4-chloro-6-(phenyl-d5)-1,3,5-triazine-2-yl)-9H-carbazole were used instead of compound A4-1 and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine. (19.3 g, yield: 80%, MS: [M+H] + =730)

[0258] Example 13: Preparation of Compound 13

[0259]

[0260] Compound 13 was prepared in the same manner as the method for preparing compound 1, except that compound B4-3 and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-(phenyl-d5)-1,3,5-triazine were used instead of compound A4-1 and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine. (16.6 g, yield: 68%, MS: [M+H] + =736)

[0261] Example 14: Preparation of Compound 14

[0262]

[0263] Compound 14 was prepared in the same manner as the method for preparing compound 1, except that compound B4-2 and 9-(4-chloro-6-phenyl-1,3,5-triazine-2-yl)-4-(phenyl-d5)-9H-carbazole were used instead of compound A4-1 and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine. (19.3 g, yield: 72%, MS: [M+H] + =811)

[0264] Example 15: Preparation of Compound 15

[0265]

[0266] Compound 15 was prepared in the same manner as for the preparation of compound 1, except that compound B4-4 and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine were used instead of compound A4-4 and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine. (18.8 g, yield: 78%, MS: [M+H] + =736)

[0267] [Experimental example]

[0268] Experimental Example 1

[0269] The ITO (indium tin oxide) that is coated with thickness as 130nm is put into the distilled water that is dissolved with detergent therein as the glass substrate of film, and carries out ultrasonic cleaning.In this case, the product made by Fischer Co. is used as detergent, and as distilled water, the distilled water filtered twice through the filter made by Millipore Co. is used.After ITO was cleaned for 30 minutes, distilled water was used to repeat ultrasonic cleaning twice for 10 minutes.After finishing with distilled water cleaning, substrate was carried out ultrasonic cleaning with the solvent of isopropyl alcohol, acetone and methanol, dried, then transferred to plasma cleaner.In addition, oxygen plasma was used to clean substrate for 5 minutes, then transferred to vacuum deposition device.

[0270] On the ITO transparent electrode thus prepared, the following compound HI-1 is thermally vacuum deposited to a thickness of 5 nm to form a hole injection layer. The following compound HT-1 is thermally vacuum deposited on the hole injection layer to a thickness of 25 nm to form a hole transport layer, and the following compound HT-2 is vacuum deposited on the HT-1 deposited layer to a thickness of 5 nm to form an electron blocking layer. Then, the previously prepared compound 1 and the following compound Dp-25 are co-deposited on the HT-2 deposited layer at a weight ratio of 88:12 to form a light-emitting layer with a thickness of 40 nm. The following compound ET-1 is vacuum deposited on the light-emitting layer to a thickness of 25 nm to form an electron transport layer, and the following compound ET-2 and LiQ are vacuum deposited (with a thickness of 10 nm) on the electron transport layer at a weight ratio of 98:2 to form an electron injection layer.

[0271] Aluminum was deposited on the electron injection layer to a thickness of 100 nm to form a cathode.

[0272]

[0273] In the above process, the vapor deposition rate of the organic material was maintained at 0.04 nm / sec to 0.07 nm / sec, the deposition rate of aluminum was maintained at 0.2 nm / sec, and the vacuum degree during deposition was maintained at 1×10 -7 Up to 5×10 -8 Entrust.

[0274] Experimental Examples 2 to 21 and Comparative Experimental Examples 1 to 9

[0275] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compounds shown in Table 1 below were used instead of Compound 1 in Experimental Example 1.

[0276] For reference, in Experimental Examples 16 to 21 and Comparative Experimental Examples 7 to 9, organic light-emitting devices were manufactured by using the compounds shown in Table 5 below in a weight ratio of 1:1 instead of Compound 1 in Experimental Example 1. For example, in Experimental Example 16, Compound 1 and Compound H-2 were used in a weight ratio of 1:1 instead of Compound 1 in Experimental Example 1.

[0277]

[0278] For the organic light-emitting devices of the experimental example and the comparative example, a 10 mA / cm 2 The voltage, efficiency, luminescent color and lifetime were measured at a current density of , and the results are shown in Table 5 below. In this case, T 95 This means that the current density is 20 mA / cm 2 When the initial brightness is set to 100%, the time required for the brightness to decrease to 95% is shown.

[0279] [Table 5]

[0280]

[0281]

[0282]

[0283] Experimental Examples 1 to 15 and Comparative Experimental Examples 1 to 6 are examples of devices in which a single host is used for the light-emitting layer. Compounds C1 to C3 used in Comparative Experimental Examples 1 to 3 are compounds in which Ar1 of dibenzothiophene is hydrogen, or Ar1, Ar2, and Ar3 are all substituted with unsubstituted aryl groups. According to Table 5, examples of devices of Experimental Examples 1 to 3 are compounds in which Ar1, Ar2, and Ar3 are all aryl groups and deuterium substituted. It can be determined that the lifespan characteristics are superior by about 21% to 40% compared to Comparative Experimental Examples 1 to 3.

[0284] Compounds C4 to C6 used in Comparative Experimental Examples 4 to 6 are compounds in which Ar1 of dibenzofuran is hydrogen, or Ar1, Ar2, and Ar3 are all substituted with unsubstituted aryl groups. The example of the device of Experimental Example 11 in Table 5 is a compound in which Ar1, Ar2, and Ar3 are all aryl groups and are substituted with deuterium. It can be confirmed that the lifespan characteristics are superior by about 11% to 21% compared with Comparative Experimental Examples 1 to 3.

[0285] The compounds used in Experimental Examples 6 to 9 and Experimental Examples 12 to 15 were compounds in which Ar1 and Ar2 were substituted with deuterium or heteroaryl groups. It was confirmed that the lifespan characteristics were superior by about 11% to 26% compared to Comparative Experimental Examples 1 to 6 in which Ar1 and Ar2 were substituted with only aryl groups.

[0286] Experimental Examples 16 to 21 are examples of devices in which two types of hosts are used for the light-emitting layer. Even when two types of hosts are used for the light-emitting layer, it can be determined that the devices of Experimental Examples 16 to 21 using the compounds of the present disclosure have excellent current efficiency and life characteristics compared to the devices of Comparative Experimental Examples 7 to 9.

[0287] <Description of symbols>

[0288] 1: Substrate 2: Anode

[0289] 3: Light-emitting layer 4: Cathode

[0290] 5: Hole injection layer 6: Hole transport layer

[0291] 7: Light-emitting layer 8: Electron transport layer

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] in, In Chemical Formula 1, X is O or S, Y1, Y2 and Y3 are each independently CH; or N, provided that at least one of Y1, Y2 and Y3 is N, L1 and L2 are each independently a direct bond; or selected from any one of the following: Ar1 is any one selected from the following: In the above formula, a is an integer from 0 to 4, b is an integer from 0 to 5, c is an integer from 0 to 7, d is an integer from 0 to 9, and e is an integer from 0 to 11, Ar2 and Ar3 are each independently any one selected from the following: In the above formula, a' is an integer from 0 to 4, b' is an integer from 0 to 5, c' is an integer from 0 to 7, d' is an integer from 0 to 8, e' is an integer from 0 to 9, and f' is an integer from 0 to 11, Provided that when Ar1, Ar2 and Ar3 are all substituted or unsubstituted C 6-60 In the case of an aryl group, any one of Ar1, Ar2 and Ar3 is substituted with 4 or more deuteriums, Each R1 is independently hydrogen; deuterium; or C 1-60 alkyl, Each R2 is independently hydrogen; deuterium; halogen; cyano; methoxy; trifluoromethyl; trifluoromethoxy; phenyl; pyridyl; isoquinolyl; or any one of the following, In the above formula, two * are each connected to adjacent carbons of carbazole in Chemical Formula 1, and The phenyl group is unsubstituted or substituted by any one selected from halogen, cyano, methoxy, trifluoromethyl and trifluoromethoxy, m is an integer from 0 to 3, n is an integer from 0 to 6, and l is 1 or 2.

2. The compound according to claim 1, The compound represented by Chemical Formula 1 is any one selected from the compounds represented by the following Chemical Formulas 2 to 8: [Chemical formula 2] [Chemical formula 3] [Chemical formula 4] [Chemical formula 5] [Chemical formula 6] [Chemical formula 7] [Chemical formula 8] in, In Chemical Formulas 2 to 8, X, Y1, Y2, Y3, L1, L2, Ar1, Ar2, Ar3, R1, R2, m and n are as defined in claim 1.

3. The compound according to claim 1, wherein each R1 is independently hydrogen or deuterium.

4. A compound selected from any one of the following 5. An organic light-emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound according to any one of claims 1 to 4.

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