Compound and organic light-emitting device containing the same

Abstract

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

Description

Technical Field

[0001] Cross-references to related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2019-0099096 filed on August 13, 2019 and Korean Patent Application No. 10-2020-0097410 filed on August 4, 2020, and incorporates all the contents disclosed in the documents of the Korean patent applications as a part of this specification.

[0003] The present invention relates to a compound and an organic light-emitting device comprising the same. Background Art

[0004] Generally speaking, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light-emitting devices using the organic light-emitting phenomenon have wide viewing angles, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, so a lot of research is being carried out.

[0005] An organic light-emitting device generally has a structure including an anode and a cathode and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light-emitting device, the organic layer is usually formed by a multilayer structure composed of different substances, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. For such an organic light-emitting device structure, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons re-transition to the ground state, light is emitted.

[0006] As for organic substances used for organic light-emitting devices as described above, development of new materials continues to be required.

[0007] Prior art literature

[0008] Patent Literature

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

[0010] Technical issues

[0011] The present invention relates to a compound and an organic light-emitting device comprising the same.

[0012] Solution to the problem

[0013] The present invention provides a compound represented by the following Chemical Formula 1:

[0014] [Chemical formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] X is O or S,

[0018] X1 to X3 are each independently CH or N, and at least one of X1 to X3 is N,

[0019] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroaryl,

[0020] R1 to R3 are each independently hydrogen (H); deuterium (D); substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroaryl,

[0021] At least one of R1 to R3 is deuterium (D), or at least one of Ar1, Ar2 and R1 to R3 is C substituted with one or more deuterium (D). 6-60 Aryl,

[0022] n and m are each independently an integer from 1 to 3,

[0023] o is an integer from 1 to 8.

[0024] In addition, the present invention provides an organic light-emitting device, which includes: a first electrode, a second electrode opposite to the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein one or more of the organic layers contains the compound represented by the above chemical formula 1.

[0025] Effects of the Invention

[0026] The compound represented by the above Chemical Formula 1 may be used as a material of an organic layer of an organic light-emitting device, and may achieve improved efficiency, lower driving voltage, and / or improved lifespan characteristics in the organic light-emitting device.

[0027] In particular, the compound represented by the above Chemical Formula 1 may 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

[0028] Figure 1An example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a hole transport layer 3 , a light-emitting layer 4 , an electron injection and transport layer 5 , and a cathode 6 is shown.

[0029] Figure 2 The diagram shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6. DETAILED DESCRIPTION

[0030] In the following, the present invention will be described in more detail to help understanding the present invention.

[0031] (Definition of terms)

[0032] In this manual, It represents the bond to other substituents.

[0033] In the present specification, the term "substituted or unsubstituted" refers to a group selected from 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 ( Alkyl thioxy); arylthio ( Aryl thioxy); alkylsulfonyl ( Alkyl sulfoxy); arylsulfonyl ( The invention also includes the following: aryl sulfoxyl group, silyl group, boryl 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 substituted or unsubstituted with one or more substituents of heteroaryl group containing one or more N, O and S atoms, or substituted or unsubstituted with substituents formed by connecting two or more substituents among the substituents exemplified above. For example, "substituent formed by connecting two or more substituents" may be biphenyl group. That is, biphenyl group may be an aryl group, and may also be interpreted as a substituent formed by connecting two phenyl groups.

[0034] In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably the number of carbon atoms is 1 to 40. Specifically, the group may have the following structure, but is not limited thereto.

[0035]

[0036] In the present specification, in the ester group, the oxygen of the ester group may be substituted by a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the group may be a group of the following structural formula, but is not limited thereto.

[0037]

[0038] In the present specification, the number of carbon atoms in the imide group is not particularly limited, but the number of carbon atoms is preferably 1 to 25. Specifically, the group may have the following structure, but is not limited thereto.

[0039]

[0040] In the present specification, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited thereto.

[0041] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0042] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0043] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl, but are not limited thereto.

[0044] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms 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 another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are 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-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0045] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0046] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group having aromaticity. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, Base, etc., but not limited to this.

[0047] In the present specification, the heteroaryl group is a heteroaryl group containing one or more of O, N, Si and S as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of the heteroaryl group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl and dibenzofuranyl, but are not limited thereto.

[0048] In this specification, the aryl group in aralkyl, aralkenyl, alkylaryl, arylamine, and arylsilyl is the same as the example of the aryl group described above. In this specification, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the example of the alkyl group described above. In this specification, the heteroaryl group in heteroarylamine can be applied to the above description of heteroaryl. In this specification, the alkenyl group in aralkenyl is the same as the example of the alkenyl. In this specification, the arylene group is a divalent group, and the above description of aryl can be applied. In this specification, the heteroarylene group is a divalent group, and the above description of heteroaryl can be applied. In this specification, the hydrocarbon ring is not a monovalent group, but two substituents are combined, and the above description of aryl or cycloalkyl can be applied. In this specification, the heterocycle is not a monovalent group, but two substituents are combined, and the above description of heteroaryl can be applied.

[0049] (Compound)

[0050] The present invention provides a compound represented by the above Chemical Formula 1.

[0051] In the above Chemical Formula 1, X1 to X3 are each independently CH or N, and at least one of X1 to X3 is N. For example, X1 to X3 may all be N.

[0052] The compound represented by the above Chemical Formula 1 has a structure based on dibenzofuran or dibenzothiophene as a core and 1,3,5-triazine and carbazole bonded to both sides of the core.

[0053] Here, the binding position of 1,3,5-triazine is not particularly limited, but the binding position of carbazole is limited to carbon number 7 of the core. Such a binding position of carbazole corresponds to a structure that adjusts the HOMO and LUMO energy levels of the compound without reducing the function of other substituents (i.e., 1,3,5-triazine), thereby adjusting the energy barrier with the organic layer.

[0054] In addition, the compound represented by the above Chemical Formula 1 includes at least one deuterium (D) in the molecule, and can more stably adjust the energy barrier with the organic layer.

[0055] Therefore, the compound represented by Chemical Formula 1 can be used as a host material of the light-emitting layer in an organic electroluminescent device due to the structure of 1,3,5-triazine and carbazole bonded to both sides of the dibenzofuran or dibenzothiophene core, the bonding position of carbazole and the synergistic effect of one or more deuterium contained in the molecule, thereby achieving low voltage, high efficiency, and especially long life characteristics.

[0056] Hereinafter, the above Chemical Formula 1 and the compounds represented by the Chemical Formula are described in detail as follows.

[0057] The compound represented by the above Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-4:

[0058] [Chemical formula 1-1]

[0059]

[0060] [Chemical formula 1-2]

[0061]

[0062] [Chemical formula 1-3]

[0063]

[0064] [Chemical formula 1-4]

[0065]

[0066] In the above Chemical Formulae 1-1 to 1-4, each substituent is as described above.

[0067] In the above Chemical Formula 1, X is O or S.

[0068] Ar1 and Ar2 may each independently be a substituted or unsubstituted C 6-30 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-30 Heteroaryl.

[0069] For example, Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, carbazole-9-yl, phenylcarbazole-9-yl or 9-phenyl-9H-carbazole, and the above Ar1 and Ar2 can each independently be unsubstituted or substituted by one or more deuterium (D).

[0070] R1 to R3 may each independently be hydrogen (H); deuterium (D); substituted or unsubstituted C 6-30 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-30 Heteroaryl.

[0071] For example, R1 and R2 may each independently be hydrogen (H); deuterium (D); or phenyl which is unsubstituted or substituted by one or more deuterium (D). In addition, R3 may be hydrogen (H), deuterium (D), phenyl which is unsubstituted or substituted by one or more deuterium (D), dibenzofuranyl which is unsubstituted or substituted by one or more deuterium (D), or dibenzothienyl which is unsubstituted or substituted by one or more deuterium (D).

[0072] n and m are each independently an integer of 1 to 3; o is an integer of 1 to 8.

[0073] The above-mentioned compound may contain at least one, specifically at least two, for example at least five, deuterium (D) in the molecule.

[0074] Here, the above-mentioned compound can increase the device life in proportion to the number of deuterium in the molecule. Specifically, compared with a compound having 1 deuterium in the molecule, when a compound having 2 or more deuterium, for example 5 or more deuterium, is used, the device life can be further increased. In other words, the more compounds with more deuterium in the molecule are used, the longer the device life tends to be.

[0075] Specifically, at least one of R1 to R3 may be deuterium (D). Different from this, at least one of Ar1, Ar2 and R1 to R3 may be a C substituted with one or more deuterium (D). 6-30 Aryl.

[0076] For example, at least one of R1 to R3 is deuterium (D), or at least one of Ar1, Ar2 and R1 to R3 may be a phenyl group substituted with one or more deuterium (D); or a biphenyl group substituted with one or more deuterium (D).

[0077] Here, the phenyl group substituted with one or more deuterium (D) groups and the biphenyl group substituted with one or more deuterium (D) groups may be a phenyl group substituted with five deuterium (D) groups and a biphenyl group substituted with five deuterium (D) groups, respectively.

[0078] Representative examples of the compound represented by the above Chemical Formula 1 are shown below:

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[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]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161] The compound represented by the above Chemical Formula 1 can be produced according to a series of steps of the following Reaction Formulas 1-1 to 1-3.

[0162] [Reaction formula 1-1]

[0163]

[0164] [Reaction 1-2]

[0165]

[0166] [Reaction 1-3]

[0167]

[0168] In the above reaction formulae 1-1 to 1-3, the definitions of the substituents are as described above. However, the above reaction formulae 1-1 to 1-3 are examples, and the compound represented by the above chemical formula 1 can be produced by referring to the synthesis examples described later.

[0169] (Organic Light Emitting Devices)

[0170] On the other hand, the present invention provides an organic light-emitting device including the compound represented by the above Chemical Formula 1. As an example, the present invention provides an organic light-emitting device, which includes: a first electrode, a second electrode provided opposite to the above first electrode, and one or more organic layers provided between the above first electrode and the above second electrode, wherein one or more of the organic layers includes the compound represented by the above Chemical Formula 1.

[0171] The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention 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 layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0172] In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or the layer that simultaneously injects and transports holes includes the compound represented by Chemical Formula 1.

[0173] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by the chemical formula 1. In this case, the light-emitting layer may further include a compound represented by the following chemical formula 2.

[0174] [Chemical formula 2]

[0175]

[0176] In the above chemical formula 2,

[0177] Ar3 and Ar4 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 Heteroaryl,

[0178] R4 and R5 are each independently hydrogen; deuterium; halogen; cyano; nitro; amino; substituted or unsubstituted C 1-60 Alkyl; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 2-60 Alkenyl; substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 Heteroaryl,

[0179] a and b are each independently an integer of 1 to 7.

[0180] More specifically, Ar3 and Ar4 are each independently phenyl, biphenyl, phenylbiphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl or dimethylfluorenyl; R4 and R5 may both be hydrogen.

[0181] For example, Ar3 and Ar4 are each independently phenyl, biphenyl, phenylbiphenyl, naphthyl or dimethylfluorenyl; R4 and R5 may both be hydrogen.

[0182] Representative examples of the compound represented by the above Chemical Formula 2 are shown below:

[0183]

[0184]

[0185]

[0186] The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including, in addition to the light-emitting layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number or a larger number of organic layers.

[0187] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device of a structure (normal type) in which the first electrode is an anode and the second electrode is a cathode, and an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device of an inverse structure (inverted type) in which the first electrode is a cathode and the second electrode is an anode, and a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to one embodiment of the present invention is shown in FIG. Figure 1 and Figure 2 .

[0188] Figure 1 The diagram shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron injection and transport layer 5, and a cathode 6. In the above structure, the compound represented by the above Chemical Formula 1 may be contained in the above hole transport layer.

[0189] Figure 2 The diagram shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6. In the structure described above, the compound represented by the above chemical formula 1 may be contained in the above hole injection layer, hole transport layer, or electron suppression layer.

[0190] The organic light-emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers contains the compound represented by the above Chemical Formula 1. In addition, when the organic light-emitting device includes a plurality of organic layers, the organic layers can be formed of the same substance or different substances.

[0191] For example, the organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, it can be manufactured as follows: a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation is used to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode substance, an organic layer, and an anode substance on a substrate.

[0192] In addition, the compound represented by the above chemical formula 1 can be used not only by vacuum evaporation method but also by solution coating method to form an organic layer when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating method, dip coating method, blade coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited to these.

[0193] In addition to these methods, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003 / 012890). However, the manufacturing method is not limited to this.

[0194] As an 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.

[0195] As the above-mentioned anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of the above-mentioned anode material include metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), 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, but are not limited thereto.

[0196] In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function. 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.

[0197] The hole injection layer is a layer for injecting holes from the electrode. As a hole injection material, it is preferably a compound having the ability to transport holes, the effect of injecting holes from the anode, an excellent hole injection effect for the light-emitting layer or the light-emitting material, and a compound having excellent thin film forming ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyanilines, and polythiophene conductive polymers, but are not limited thereto.

[0198] The hole transport layer is a layer that receives holes from the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. A material with a large mobility of holes is suitable. As the hole transport material, a compound represented by the above chemical formula 1 is used, or an arylamine-based organic substance, a conductive polymer, and a block copolymer having both a conjugated portion and a non-conjugated portion can be used, but it is not limited thereto.

[0199] The electron suppression layer is formed on the hole transport layer, preferably in contact with the light-emitting layer, and improves the efficiency of the organic light-emitting device by adjusting the hole mobility, preventing the excessive migration of electrons, and increasing the probability of the combination between holes and electrons. The electron suppression layer includes an electron blocking substance. As an example of such an electron blocking substance, a compound represented by the above chemical formula 1 or an arylamine-based organic substance can be used, but it is not limited thereto.

[0200] The above-mentioned luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo The present invention includes, but is not limited to, oxazole, benzothiazole and benzimidazole compounds; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene; rubrene, etc.

[0201] The above-mentioned light-emitting layer may include a host material and a dopant material as described above. The host material may also include an aromatic fused ring derivative or a heterocyclic compound. Specifically, as an aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0202] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamino groups, and there are pyrene, anthracene, , diindenopyrene, etc. The styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as a metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0203] The hole blocking layer is formed on the light-emitting layer, preferably in contact with the light-emitting layer, and improves the efficiency of the organic light-emitting device by adjusting the electron mobility, preventing the excessive migration of holes, and increasing the probability of the combination between holes and electrons. The hole blocking layer contains a hole blocking substance. Examples of such a hole blocking substance include azine derivatives including triazine, triazole derivatives, Compounds into which an electron-withdrawing group is introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, phosphine oxide derivatives, and the like.

[0204] The electron injection and transport layer is a layer that simultaneously injects electrons from the electrode and transports the received electrons to the electron transport layer and the electron injection layer, and is formed on the above-mentioned light-emitting layer or the above-mentioned hole blocking layer. Such electron injection and transport substances are substances that can well receive electrons from the cathode and transfer them to the light-emitting layer, and substances with high electron mobility are suitable. Specific examples of electron injection and transport substances include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, triazine derivatives, etc., but are not limited to these. Alternatively, it can also be combined with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone and the like, and derivatives thereof, metal coordination compounds, or nitrogen-containing five-membered ring derivatives and the like can be used together, but are not limited thereto.

[0205] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

[0206] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0207] In addition, the compound represented by the above Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

[0208] The following will explain the functions and effects of the invention in more detail through specific embodiments of the invention. However, these are provided as examples of the invention, and the scope of the invention is not limited in any sense by them.

[0209] Synthesis Example 1: Synthesis of Intermediate A

[0210]

[0211] Under nitrogen atmosphere, 6-bromo-3-chlorodibenzo[b,d]furan (20 g, 71 mmol) and bis(pinacolato)diboron (18 g, 71 mmol) were added to 400 ml of distilled water. alkane (Diox), stirring and reflux. Then, potassium phosphate tripotassium (45.2g, 213.1mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium (1.2g, 2.1mmol) and tricyclohexylphosphine (1.2g, 4.3mmol) were added. After reacting for 6 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. The obtained product was again added to 20 times 467mL of chloroform and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a white solid compound A (11.9g, 51%, MS: [M+H] + =329.6).

[0212] Synthesis Example 2: Synthesis of Intermediate B

[0213]

[0214] In Synthesis Example 1, Intermediate B was produced by the same production method as that of Intermediate A, except that 3-bromo-7-chlorodibenzo[b,d]furan was used instead of 6-bromo-3-chlorodibenzo[b,d]furan. (MS[M+H] + =329.6)

[0215] Synthesis Example 3: Synthesis of Intermediate C

[0216]

[0217] In Synthesis Example 1, Intermediate C was produced by the same production method as that of Intermediate A, except that 2-bromo-7-chlorodibenzo[b,d]furan was used instead of 6-bromo-3-chlorodibenzo[b,d]furan. (MS[M+H] + =329.6)

[0218] Synthesis Example 4: Synthesis of Intermediate D

[0219]

[0220] In Synthesis Example 1, Intermediate D was produced by the same production method as that of Intermediate A, except that 1-bromo-7-chlorodibenzo[b,d]furan was used instead of 6-bromo-3-chlorodibenzo[b,d]furan. (MS[M+H]+ =329.6)

[0221] Synthesis Example 5: Synthesis of Compound 1

[0222] Step 1) Synthesis of intermediate A-1

[0223]

[0224] Under nitrogen atmosphere, A (15 g, 53.3 mmol) and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine (14.5 g, 53.3 mmol) were added to 300 ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (22.1 g, 159.8 mmol) was dissolved in 22 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (1.8 g, 1.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was again added to 50 times 1169 mL of chloroform and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound A-1 (14.7 g, 63%, MS: [M+H] + =439.9).

[0225] Step 2) Synthesis of Compound 1

[0226]

[0227] Under nitrogen atmosphere, A-1 (20 g, 45.6 mmol) and 3-phenyl-9H-carbazole (3-pheny l-9H-carbazole) (11.1 g, 45.6 mmol) were added to 400 ml of xylene, stirred and refluxed. Then, sodium tert-butoxide (13.1 g, 136.7 mmol) was added, and after sufficient stirring, bis(tri-tert-butylphosphine) palladium (0.7 g, 1.4 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. The obtained product was again added to 50 times 1471 mL of chloroform and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by passing through a silica gel column using chloroform and ethyl acetate to produce a white solid compound compound 1 (18.5 g, 63%, MS: [M+H] + =646.8).

[0228] Synthesis Example 6: Synthesis of Compound 2

[0229]

[0230] In Synthesis Example 5, Compound 2 was produced by the same production method as that of Compound 1, except that 4-phenyl-9H-carbazole was used instead of 3-phenyl-9H-carbazole. ([M+H] + =646.8)

[0231] Synthesis Example 7: Synthesis of Compound 3

[0232]

[0233] In step 1 of Synthesis Example 5, 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine, and in step 2, 2-(phenyl-d5)-9H-carbazole was used instead of 3-phenyl-9H-carbazole. Compound 3 was produced by the same production method as the production method of compound 1. ([M+H] + =646.8)

[0234] Synthesis Example 8: Synthesis of Compound 4

[0235]

[0236] In step 1 of Synthesis Example 5, 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine was used instead of 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine, and in step 2, 3-phenyl-9H-carbazole was replaced with 2,4-diphenyl-9H-carbazol. Compound 4 was produced by the same production method as that of Compound 1. ([M+H] + =727.9)

[0237] Synthesis Example 9: Synthesis of Compound 5

[0238]

[0239] In step 1 of Synthesis Example 5, intermediate A was replaced with intermediate B, and in step 2, 3-phenyl-9H-carbazole was replaced with 9H-carbazole. Compound 5 was produced by the same production method as that of compound 1. ([M+H] + =570.7)

[0240] Synthesis Example 10: Synthesis of Compound 6

[0241]

[0242] Step 1) In Synthesis Example 1, intermediate E was produced by the same production method as intermediate A, except that 3-bromo-7-chlorodibenzo[b,d]furan-1,2,4,6,8,9-d6 was used instead of 6-bromo-3-chlorodibenzo[b,d]furan.

[0243] Step 2) In Synthesis Example 9, except that B was replaced by Intermediate E and 9H-carbazole was replaced by 3-phenyl-9H-carbazole, Compound 6 was prepared by the same method as that of Compound 5. ([M+H] + =646.7)

[0244] Synthesis Example 11: Synthesis of Compound 7

[0245]

[0246] In Synthesis Example 9, Compound 7 was produced by the same production method as that of Compound 5, except that 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine was used instead of 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine. ([M+H] + =575.7)

[0247] Synthesis Example 12: Synthesis of Compound 8

[0248]

[0249] In Synthesis Example 9, Compound 8 was produced by the same production method as that of Compound 5, except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine, and 9H-carbazole was used instead of 3-phenyl-9H-carbazole-1,2,4,5,6,7,8-d7. ([M+H] + =738.9)

[0250] Synthesis Example 13: Synthesis of Compound 9

[0251]

[0252] In Synthesis Example 9, Compound 9 was produced by the same production method as that of Compound 5, except that 2-([1,1'-biphenyl]-4-yl)-4-(7-chlorodibenzo[b,d]furan-3-yl)-6-(phenyl-d5)-1,3,5-triazine was used instead of 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine. ([M+H] + =646.8)

[0253] Synthesis Example 14: Synthesis of Compound 10

[0254]

[0255] In step 1 of Synthesis Example 5, intermediate A was replaced with intermediate C, and in step 2, 3-phenyl-9H-carbazole was replaced with 9H-carbazole. Compound 10 was produced by the same production method as that of compound 1. ([M+H] + =570.7)

[0256] Synthesis Example 15: Synthesis of Compound 11

[0257]

[0258] Compound 11 was prepared by the same method as that of Compound 1, except that Intermediate A was replaced with Intermediate D in Step 1 of Synthesis Example 5. ([M+H] + =646.8)

[0259] Synthesis Example 16: Synthesis of Compound 12

[0260]

[0261] In step 1 of Synthesis Example 15, compound 12 was produced by the same production method as compound 11, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine, and 9H-carbazole-1,2,3,4,5,6,7,8-d8 was used instead of 3-phenyl-9H-carbazole in step 2. ([M+H] + =649.8)

[0262] Synthesis Example 17: Synthesis of Compound 13

[0263]

[0264] Step 1) In Synthesis Example 4, except that 1-bromo-7-chlorodibenzo[b,d]furan was replaced with 1-bromo-7-chlorodibenzo[b,d]furan-2,3,4,6,8,9-d6, Intermediate F was produced by the same production method as that of Intermediate D.

[0265] Step 2) In Synthesis Example 5, Intermediate A was replaced with Intermediate F, 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine, and 3-phenyl-9H-carbazole was replaced with 9H-carbazole. Compound 13 was prepared by the same preparation method as Compound 1. ([M+H] + =661.8)

[0266] Synthesis Example 18: Synthesis of Compound 14

[0267]

[0268] In step 1 of Synthesis Example 15, 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and in step 2, 4-(phenyl-d5)-9H-carbazole was used instead of 3-phenyl-9H-carbazole. Compound 14 was produced by the same production method as that of Compound 11. ([M+H] + =646.8)

[0269] Example 1

[0270] ITO (Indium Tin Oxide) The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0271] On the ITO transparent electrode prepared in this way, the following HT-A and 5 wt% PD were added in the form of Then, only HT-A material is deposited with a thickness of On the hole transport layer, as an electron blocking layer, the following HT-B was deposited with a thickness of Then, the main body was formed by using compound 1 as the first main body and GH-A as the second main body in a weight ratio of 40:60, and GD was used as a dopant at 15 wt % of the main body. Next, as a hole blocking layer, the following ET-A was deposited with Next, as an electron transport and injection layer, the following ET-B and Liq were mixed in a ratio of 2:1 and Then, LiF and magnesium were deposited in a ratio of 1:1 and On the electron injection layer, magnesium and silver are deposited in a ratio of 1:4 and A cathode is formed by evaporation with a thickness of , thereby manufacturing an organic light-emitting device.

[0272]

[0273] Examples 2 to 14, and Comparative Examples 1 to 6

[0274] Organic light-emitting devices of Examples 2 to 14 and Comparative Examples 1 to 6 were prepared in the same manner as in Example 1, except that the host material was changed to the compounds listed in Table 1 below. In this case, when a mixture of two compounds was used as the host, the weight ratio between the host compounds is indicated in brackets.

[0275]

[0276] <Experimental Example: Device Characteristics Evaluation>

[0277] The organic light-emitting devices prepared in Examples 1 to 14 and Comparative Examples 1 to 6 were heat-treated in an oven at 100°C for 30 minutes, then taken out and current was applied. The voltage, efficiency and life (T95) were measured. The results are shown in Table 1 below. At this time, the voltage and efficiency were measured by applying 10 mA / cm 2 T95 is measured at a current density of 20 mA / cm 2 The time (hr) when the initial brightness drops to 95%.

[0278] [Table 1]

[0279] According to the above Table 1, an organic light emitting electroluminescent device using the compound represented by the above Chemical Formula 1 as a host material of a light emitting layer obtains advantages in voltage and efficiency, and in particular, can achieve long life characteristics.

[0280] In particular, when comparing compounds having the same or similar skeleton as that of Chemical Formula 1 above but with different carbazole bonding positions and deuterium substitution, it is found that the voltage, efficiency, and particularly the life of the device are significantly affected.

[0281] Comparative Examples 2 and 4 use compounds having the same or similar skeletons as Comparative Examples 5 and 6 and different carbazole bonding positions as the host material of the light-emitting layer. In addition, Examples 11 and 9 use compounds having the same or similar skeletons as Comparative Examples 2 and 4 and different deuterium substitution and carbazole bonding positions as the host material of the light-emitting layer.

[0282] Here, it was confirmed that Examples 11 and 9 had a reduced voltage, improved efficiency, and particularly significantly increased lifespan of the device when compared not only to Comparative Examples 5 and 6 but also to Comparative Examples 2 and 4.

[0283] On the other hand, Examples 8 and 9 respectively used compounds having the same or similar skeletons as Comparative Examples 3 and 4 and differing in whether they were substituted with deuterium as host substances. Here, it was confirmed that the voltage of the device of Examples 8 and 9 was reduced, the efficiency was improved, and the life was significantly increased, in particular, compared with Comparative Examples 3 and 4.

[0284] In addition, Examples 11 and 12 respectively use compounds having the same or similar skeletons as Comparative Examples 1 and 2 and differing in whether they are substituted with deuterium as host substances. Here, it was confirmed that Examples 11 and 12 each had a reduced voltage, improved efficiency, and, in particular, significantly increased lifespan of the device compared to Comparative Examples 1 and 2.

[0285] In summary, it can be seen that the compound represented by the above chemical formula 1 can be used as the main material of the light-emitting layer in an organic electroluminescent device due to the synergistic effect of the structure of 1,3,5-triazine and carbazole bonded to both sides of the dibenzofuran or dibenzothiophene core, the bonding position of carbazole (bonded to carbon No. 7 of the above core), and the presence of one or more (specifically two or more, for example, five or more) deuterium in the molecule, thereby achieving low voltage, high efficiency, and especially long life characteristics.

[0286] In other words, an organic electroluminescent device using the compound represented by the above Chemical Formula 1 as a host substance of a light-emitting layer obtains advantages in voltage and efficiency, and in particular, can achieve long life characteristics.

[0287] [Explanation of symbols]

[0288] 1: Substrate 2: Anode

[0289] 3: Hole transport layer 4: Light-emitting layer

[0290] 5: Electron injection and transport layer 6: Cathode

[0291] 7: Hole injection layer 8: Electron suppression layer

[0292] 9: Hole blocking layer.

Claims

1. A compound represented by any one of the following chemical formulas 1-1, 1-3 and 1-4: Chemical formula 1-1 Chemical formula 1-3 Chemical formula 1-4 in, In the chemical formulas 1-1, 1-3 and 1-4, X is O or S, X1 to X3 are each independently CH or N, provided that at least one of X1 to X3 is N, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-30 Aryl; or a substituted or unsubstituted C containing any one heteroatom selected from N, O and S 2-30 Heteroaryl, R1 and R2 are each independently hydrogen (H); deuterium (D); or phenyl which is unsubstituted or substituted with one or more deuterium (D), R3 is hydrogen (H), deuterium (D), phenyl which is unsubstituted or substituted by one or more deuterium (D), dibenzofuranyl which is unsubstituted or substituted by one or more deuterium (D), or dibenzothienyl which is unsubstituted or substituted by one or more deuterium (D), wherein at least one of R1 to R3 is deuterium (D), or At least one of Ar1, Ar2 and R1 to R3 is a phenyl group substituted with one or more deuterium (D) groups, or a biphenyl group substituted with one or more deuterium (D) groups, n and m are each independently an integer from 1 to 3, and o is an integer from 1 to 8, and The term "substituted or unsubstituted" means unsubstituted or selected from deuterium, halogen groups, C 1-20 Alkyl and C 6-30 The aryl group is substituted by one or more substituents, or by a substituent formed by connecting two or more substituents among the substituents, The compounds described do not include:

2. The compound according to claim 1, wherein X1 to X3 are all N.

3. The compound according to claim 1, wherein Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, carbazole-9-yl, phenylcarbazole-9-yl or 9-phenyl-9H-carbazole, wherein Ar1 and Ar2 are each independently unsubstituted or substituted with one or more deuterium (D).

4. The compound according to claim 1, wherein At least 2 deuterium (D) are present in the molecule of the compound.

5. The compound according to claim 1, wherein The phenyl group substituted with one or more deuterium (D) and the biphenyl group substituted with one or more deuterium (D) are respectively a phenyl group substituted with five deuterium (D) and a biphenyl group substituted with five deuterium (D).

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

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

8. The organic light emitting device according to claim 7, wherein: The organic layer includes a light-emitting layer, and the light-emitting layer contains the compound.

9. The organic light emitting device according to claim 8, wherein: The light-emitting layer further comprises a compound represented by the following Chemical Formula 2: Chemical formula 2 Wherein, in the chemical formula 2, Ar3 and Ar4 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 Heteroaryl, R4 and R5 are each independently hydrogen; deuterium; halogen; cyano; nitro; amino; substituted or unsubstituted C 1-60 Alkyl; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 2-60 Alkenyl; substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 Heteroaryl, and a and b are each independently an integer of 1 to 7.

10. The organic light emitting device according to claim 9, wherein: Ar3 and Ar4 are each independently phenyl, biphenyl, phenylbiphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl or dimethylfluorenyl.

11. The organic light emitting device according to claim 9, wherein: R4 and R5 are both hydrogen.

12. The organic light emitting device according to claim 9, wherein: The compound represented by the chemical formula 2 is any one selected from the following compounds:

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