Compounds and organic light emitting devices using the same

Abstract

The present application provides a compound and an organic light emitting device using the same. The compound is represented by the following chemical formula:

Description

[0001] This application is a divisional application of the application filed on February 5, 2020, with application number 202080007245.0 and entitled "Novel Compound and Organic Light-Emitting Device Using the Same" (PCT / KR2020 / 001670, entered the national phase on June 22, 2021). Technical Field

[0002]

[01] This application claims priority based on Korean Patent Application No. 10-2019-0017983, dated February 15, 2019, the entire contents of which are disclosed in the Korean Patent Application document and are incorporated into this specification. 02]

[0004]

[03] This invention relates to compounds and organic light-emitting devices containing the same. Background Technology

[0005]

[04] Generally speaking, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices utilizing organic light emission have wide viewing angles, excellent contrast, fast response times, and excellent brightness, driving voltage, and response speed characteristics, and are therefore the subject of extensive research. 05]

[0007]

[06] Organic light-emitting devices typically have a structure including an anode and a cathode, and an organic layer located between the anode and the cathode. To improve the efficiency and stability of organic light-emitting devices, the organic layer is often formed by a multilayer structure made of different materials, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In 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, an exciton is formed, and when the exciton re-transitions to the ground state, it emits light. 07]

[0009]

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

[0010] [Existing Technical Documents]

[0011] [Patent Literature]

[0012] (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826 Summary of the Invention

[0013] Technical issues

[0014] This invention relates to compounds and organic light-emitting devices containing the same.

[0015] Solution to the problem

[0016] This invention provides compounds represented by the following chemical formula 1:

[0017] [Chemical Formula 1]

[0018]

[0019] In the above chemical formula 1,

[0020] L1 to L3 are each an independent single bond; substituted or unsubstituted C 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 heteroaryl,

[0021] A is phenanthrene, triphenylene, dibenzofuranyl, or dibenzothiophene.

[0022] In this case, A was not replaced, or each of the above terms was independently selected from C. 1-20 Alkyl; C 6-20 aryl; and C containing one or more heteroatoms selected from N, O, and S. 2-20 One or more substituents in a heteroaryl group are substituted.

[0023] B is a substituent represented by the following chemical formula 2.

[0024] Ar is a substituent represented by the following chemical formula 2; substituted or unsubstituted C 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0025] [Chemical Formula 2]

[0026]

[0027] In the above chemical formula 2,

[0028] X is O or S.

[0029] One of R1 to R3 is bonded to L2 or L3, and the others are independently hydrogen; deuterium; substituted or unsubstituted C. 1-60 Alkyl; substituted or unsubstituted C 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0030] However, when L2 or L3 binds to R1 or R2, the unbound R1 or R2 is not hydrogen.

[0031] n is an integer from 1 to 4.

[0032] In addition, the present invention provides an organic light-emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and an organic layer of one or more disposed between the first electrode and the second electrode, wherein one or more of the organic layer comprises a compound represented by the above chemical formula 1.

[0033] Invention Effects

[0034] The compound represented by the above chemical formula 1 can be used as a material for the organic layer of organic light-emitting devices, thereby achieving improved efficiency, lower driving voltage, and / or improved lifetime characteristics in organic light-emitting devices. Attached Figure Description

[0035] Figure 1 The illustration shows an example of an organic light-emitting device consisting 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.

[0036] Figure 2 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, a hole conditioning layer 8, a light-emitting layer 4, an electron conditioning layer 9, an electron injection and transport layer 5, and a cathode 6. Detailed Implementation

[0037] The invention will now be described in more detail to aid in understanding.

[0038] Definition of terms

[0039] In this instruction manual, This indicates a bond that is linked to other substituents.

[0040] In this specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; halogen group; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thio group ( Alkylthioxy); aryl thio ( Aryl thioxy); alkyl sulfonyl ( Alkylsulfoxy); arylsulfonyl ( Aryl sulfoxy; silyl; boronyl; alkyl; cycloalkyl; alkenyl; aryl; aralkyl; arylene; alkylaryl; alkylamine; aralkylamine; heteroarylamine; arylamine; arylphosphinyl; or a substituent consisting of one or more heteroaryl groups containing N, O, and S atoms, substituted or unsubstituted, or substituted or unsubstituted by two or more substituents linked together as exemplified above. For example, "a substituent consisting of two or more substituents linked together" can be biphenyl. That is, biphenyl can be aryl, or it can be interpreted as a substituent consisting of two phenyl groups linked together.

[0041] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but it is preferred to have 1 to 40 carbon atoms. Specifically, it can be a compound with the following structure, but is not limited thereto.

[0042]

[0043] In this specification, the oxygen atom in the ester group may be replaced by a straight-chain, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound with the following structural formula, but is not limited thereto.

[0044]

[0045] In this specification, the number of carbon atoms in the imide group is not particularly limited, but it is preferred to have 1 to 25 carbon atoms. Specifically, it can be a compound with the following structure, but is not limited thereto.

[0046]

[0047] In this specification, silanes specifically include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc., but are not limited to these.

[0048] In this specification, boron groups specifically include trimethylboronyl, triethylboronyl, tert-butyldimethylboronyl, triphenylboronyl, phenylboronyl, etc., but are not limited to these.

[0049] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine.

[0050] In this specification, the alkyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of alkyl groups 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, 5-methylhexyl, etc., but are not limited to these.

[0051] In this specification, the alkenyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to yet another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples 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, styryl, styryl, etc., but are not limited to these.

[0052] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group with 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, 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., are used, but are not limited to these.

[0053] In this specification, the aryl group is not particularly limited, but is preferably an aryl group with 6 to 60 carbon atoms, and can be a monocyclic aryl or polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Regarding the aforementioned aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but is not limited to these. As the aforementioned polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, etc. It includes bases, fluorenes, etc., but is not limited to these.

[0054] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure. When the fluorene group is substituted as described above, it can be used to... Etc. But it is not limited to this.

[0055] In this specification, a heteroaryl group is a heteroaryl group containing one or more of O, N, Si, and S as heteroatoms. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of heteroaryl groups include thienyl, furanyl, pyrroleyl, imidazolyl, and thiazolyl. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, iso Azolyl, thiadiazolyl, phenthiazinyl, and dibenzofuranyl groups, but not limited to these.

[0056] In this specification, the aryl groups in aralkyl, aryl-alkenyl, alkylaryl, arylamino, and arylsilyl are the same as those exemplified above. In this specification, the alkyl groups in aralkyl, alkylaryl, and alkylamino are the same as those exemplified above. In this specification, the heteroaryl groups in heteroarylamines are subject to the above descriptions regarding heteroaryl groups. In this specification, the alkenyl groups in aryl-alkenyl are the same as those exemplified above. In this specification, arylene is a divalent group; otherwise, the above descriptions regarding aryl groups apply. In this specification, heteroarylene is a divalent group; otherwise, the above descriptions regarding heteroaryl groups apply. In this specification, the hydrocarbon ring is not a monovalent group but is formed by the combination of two substituents; otherwise, the above descriptions regarding aryl or cycloalkyl groups apply. In this specification, the heterocycle is not a monovalent group but is formed by the combination of two substituents; otherwise, the above descriptions regarding heteroaryl groups apply.

[0057] compound

[0058] On the other hand, the present invention provides amine compounds represented by the above-described chemical formula 1.

[0059] The amine compounds represented by the above-described chemical formula 1 contain any one of the substituents selected from phenanthrene, triphenylene, dibenzofuranyl, and dibenzothiophene, as well as any one of the substituents selected from benzofuranyl and benzothiophene, thereby enabling organic light-emitting devices (OLEDs) employing these compounds to achieve high efficiency, low driving voltage, and long lifetime. Furthermore, when the aforementioned benzofuranyl or benzothiophene substituents are represented by the above-described chemical formula 2, in the case where L2 or L3 is combined with R1 or R2 of the above-described chemical formula 2, OLEDs employing compounds where the uncombined R1 or R2 is hydrogen exhibit higher voltage, lower efficiency, and poorer lifetime characteristics compared to OLEDs employing compounds represented by the above-described chemical formula 1, as can be confirmed in the comparative examples described later, and are therefore excluded from the present invention.

[0060] In the above chemical formula 1, preferably, L1 to L3 are each independently a single bond, a phenylene group, a biphenyl dimethyl group, or a naphthylene group.

[0061] More preferably, L1 to L3 are each independently a single bond, or selected from any one of the following groups:

[0062]

[0063] Preferably, A is phenanthrene, triphenylene, dibenzofuranyl, or dibenzothiophene, wherein A is not substituted or is independently selected from C. 1-20 Alkyl and C 6-60 One to three substituents in the aryl group are substituted.

[0064] More preferably, A is represented by any one of the following chemical formulas a1 to a4.

[0065]

[0066] In the above chemical formulas a1 to a4,

[0067] R can be either hydrogen or C independently. 6-20 Aryl.

[0068] In this case, the two Rs in chemical formulas a3 and a4 can be the same or different from each other; for example, each R can be hydrogen, phenyl, or naphthyl.

[0069] Preferably, in the above chemical formula 2, R1 to R3, which are not combined with L2 or L3, are each independently hydrogen, deuterium, and C. 1-10 Alkyl or C 6-20 Aryl groups, where n is 1, 2, or 3. In this case, when n is 2 or more, R3 groups are either the same or different.

[0070] More preferably, the substituent represented by the above chemical formula 2 is represented by any one of the following chemical formulas b1 to b3:

[0071]

[0072] In the above chemical formulas b1 to b3,

[0073] X is O or S.

[0074] R1 and R2 are each independently C 1-10 Alkyl or C 6-20 Aryl,

[0075] R3 and R1' to R3' are each independently hydrogen and C. 1-10 Alkyl, C 6-20 aryl, or C containing heteroatoms O or S 2-20 In heteroaryl compounds, the two R3 groups in the chemical formula b2 can be the same or different from each other.

[0076] Most preferably, in the above chemical formulas b1 and b2,

[0077] R1 is methyl, ethyl, phenyl, biphenyl, or naphthyl.

[0078] R2 is methyl, ethyl, phenyl, or biphenyl.

[0079] R3 can be hydrogen, methyl, or phenyl independently.

[0080] In the above chemical formula b3,

[0081] R1' to R3' are each independently hydrogen, methyl, isopropyl, naphthyl, phenyl, or dibenzothiophene.

[0082] Preferably, Ar is a substituent represented by the above chemical formula 2; selected from any one aryl group among phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, spiro[cyclopentane-1,9'-fluorenyl]yl and spiro[cyclohexane-1,9'-fluorenyl]yl; or selected from any one heteroaryl group among dibenzofuranyl, dibenzothiophenyl and carbazoleyl.

[0083] In this configuration, the aforementioned aryl or heteroaryl groups are either independently unsubstituted or independently selected from deuterium, C, etc. 1-10 Alkyl and C 6-20 One to five substituents in the aryl group are substituted.

[0084] More preferably, the aforementioned aryl or heteroaryl groups are each independently unsubstituted or substituted by one to five substituents selected independently from deuterium, methyl, and phenyl.

[0085] Most preferably, Ar is selected from any one of the following groups:

[0086]

[0087] Among the above groups,

[0088] Y is O, S, N (phenyl) or C (methyl)2.

[0089] Preferably, the above-mentioned compound is represented by any one of the following chemical formulas 1-1 to 1-6:

[0090]

[0091] In the above chemical formulas 1-1 to 1-6,

[0092] The descriptions of L1 to L3, B, and Ar are the same as those in the definitions in Chemical Formula 1 above.

[0093] Q is either O or S.

[0094] R is hydrogen, phenyl, or naphthyl.

[0095] Representative examples of compounds represented by the above chemical formula 1 are shown below:

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102] On the other hand, as an example, the compound represented by the above chemical formula 1 can be manufactured by the manufacturing method shown in reaction formula 1 below. The above manufacturing method can be further specified in the manufacturing examples described later.

[0103] [Reaction Formula 1]

[0104]

[0105] In the above reaction formula 1, each X' is an independent halogen, preferably bromine or chlorine, and the definitions of the remaining substituents are the same as those described above.

[0106] Step 1-1 above involves introducing an SM2 radical into the primary amine of the starting material SM1 to produce intermediate compound X (INT.X), and step 1-2 involves introducing an SM3 radical into the secondary amine of intermediate compound X (INT.X) to produce the compound represented by the above chemical formula 1 as a tertiary amine compound. Both steps 1-1 and 1-2 are carried out via a Buchwald-Hartwig reaction, preferably in the presence of a palladium catalyst. This manufacturing method can be further specified in the manufacturing examples described later.

[0107] Organic light-emitting devices

[0108] On the other hand, the present invention provides an organic light-emitting device comprising a compound represented by the above-described chemical formula 1. As an example, the present invention provides an organic light-emitting device comprising: 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 a compound represented by the above-described chemical formula 1.

[0109] The organic layer of the organic light-emitting device of the present invention can be formed as a single-layer structure or as a multi-layer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of the present invention can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer as organic layers. However, the structure of the organic light-emitting device is not limited to this and may include fewer organic layers.

[0110] In addition, the aforementioned organic layer may include a hole injection layer, a hole transport layer, or a layer that performs both hole injection and transport simultaneously, wherein the aforementioned hole injection layer, hole transport layer, or layer that performs both hole injection and transport simultaneously comprises a compound represented by the aforementioned chemical formula 1.

[0111] In addition, the aforementioned organic layer may include a light-emitting layer, which contains a compound represented by the aforementioned chemical formula 1.

[0112] The organic layer of the organic light-emitting device of the present invention can be formed as a single-layer structure or as a multi-layer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of the present invention may have a structure that, in addition to the light-emitting layer, includes 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 organic layers. However, the structure of the organic light-emitting device is not limited to this, and may include fewer or more organic layers.

[0113] Furthermore, the organic light-emitting device according to the present invention can be an organic light-emitting device with the first electrode as the anode, the second electrode as the cathode, and an anode, one or more organic layers, and a cathode sequentially stacked on a substrate (normal type). Additionally, the organic light-emitting device according to the present invention can be an organic light-emitting device with the first electrode as the cathode, the second electrode as the anode, and a cathode, one or more organic layers, and an anode sequentially stacked on a substrate (inverted type). For example, the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated below. Figure 1 and 2 .

[0114] Figure 1 The illustration shows an example of an organic light-emitting device consisting 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 structure described above, the compound represented by the above chemical formula 1 may be included in the hole transport layer.

[0115] Figure 2 The illustration shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, a hole modulation layer 8, a light-emitting layer 4, an electron modulation 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 included in the hole transport layer and the hole modulation layer, or may be included in both the hole transport layer and the hole modulation layer.

[0116] The organic light-emitting device according to the present invention, except that one or more of the organic layers contain a compound represented by the above-described chemical formula 1, can be manufactured using materials and methods known in the art. Furthermore, when the organic light-emitting device comprises a plurality of organic layers, the organic layers can be formed from the same substance or different substances.

[0117] 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. This can be achieved by: depositing a metal or a conductive metal oxide or alloy thereof onto the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; then forming an organic layer comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the anode; and finally depositing a material suitable for use as a cathode onto the organic layer. Alternatively, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto the substrate.

[0118] Furthermore, the compound represented by the above chemical formula 1 can be used to form an organic layer in the manufacture of organic light-emitting devices not only by vacuum evaporation but also by solution coating. Here, solution coating refers to methods such as spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, and roller coating, but is not limited to these.

[0119] In addition to these methods, organic light-emitting devices 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 these methods.

[0120] As an example, the first electrode is the anode and the second electrode is the cathode, or the first electrode is the cathode and the second electrode is the anode.

[0121] As the aforementioned anode material, a material with a high work function is preferred in order to facilitate the injection of holes into the organic layer. Specific examples of the aforementioned anode materials include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0122] As the cathode material described above, a material with a low work function is generally preferred in order to facilitate the injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer structures such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0123] The aforementioned hole injection layer is a layer that injects holes from the electrode. Preferably, the hole injection material is a compound that possesses the ability to transport holes, the effect of injecting holes from the anode, excellent hole injection performance for the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material, and exhibits excellent thin film formation capability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between that of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile hexaazabenzophenanthrene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and conductive polymers such as polyaniline and polythiophene.

[0124] The aforementioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. As a hole transport material, it is suitable to be a material capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer, and a material with high hole mobility is preferred. As the aforementioned hole transport material, compounds represented by the aforementioned chemical formula 1 can be used, or aryl amine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions can be used, but are not limited to these.

[0125] The aforementioned hole modulation layer refers to a layer formed on the aforementioned hole transport layer, preferably disposed in contact with the light-emitting layer, which improves the efficiency of organic light-emitting devices by adjusting the hole mobility, preventing excessive electron migration, and thus preventing excessive electron-hole binding. The aforementioned hole modulation layer contains a hole modulation material. Examples of such a material include compounds represented by the aforementioned chemical formula 1, or aryl amine-based organic compounds, but are not limited to these.

[0126] The aforementioned luminescent materials are those capable of receiving holes and electrons from the hole transport layer and electron transport layer, respectively, and combining them to emit light in the visible light region. Preferably, these materials possess high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complexes (Alq3); carbazole compounds; diluted styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Compounds including azoles, benzothiazoles and benzimidazoles; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, fluorene, etc., but not limited to these.

[0127] The aforementioned luminescent layer may comprise a host material and a dopant material, as described above. The host material may also comprise aromatic fused-ring derivatives or heterocyclic compounds. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds. Pyrimidine derivatives, etc., but not limited to these.

[0128] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are aromatic fused-ring derivatives with substituted or unsubstituted aryl amino groups, such as pyrene, anthracene, etc. Diindrone pyrene, etc., styrylamine compounds are compounds in which at least one aryl vinyl group is substituted onto a substituted or unsubstituted arylamine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamines, styryldiamines, styryltriamines, styryltetraamines, etc., but they are not limited to these. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but they are not limited to these.

[0129] The aforementioned electronic regulation layer refers to a layer formed on the light-emitting layer, preferably in contact with it, that improves the efficiency of the organic light-emitting device by regulating electron mobility, preventing excessive hole migration, and thus increasing the probability of hole-electron binding. This electronic regulation layer contains an electronic regulation material; examples of such materials include azazine derivatives, triazole derivatives, etc. Compounds containing electron-withdrawing groups, such as diazole derivatives, phenanthrene-rhein derivatives, and phosphine oxide derivatives, are included, but are not limited to these.

[0130] The aforementioned electron injection and transport layer is a layer that injects electrons from the electrode and transports the received electrons to the light-emitting layer, simultaneously functioning as an electron transport layer and an electron injection layer, and is formed on the aforementioned light-emitting layer or the aforementioned electron regulation layer. Such an electron injection and transport material is one that can effectively inject electrons from the cathode and transfer them to the light-emitting layer; materials with high electron mobility are suitable. Specific examples of electron injection and transport materials include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, triazine derivatives, etc., but are not limited to these. Alternatively, it can be combined with fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives may be used together, but are not limited to these.

[0131] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, 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, but are not limited to these.

[0132] Depending on the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0133] In addition, the compound represented by the above chemical formula 1 can be included not only in organic light-emitting devices, but also in organic solar cells or organic transistors.

[0134] The manufacture of compounds represented by the above chemical formula 1 and organic light-emitting devices containing them is specifically described in the following examples. However, the following examples are for illustrative purposes only and the scope of the invention is not limited thereto.

[0135] Synthetic Example 1: Production of Substituents

[0136] In order to introduce the substituent represented by the above chemical formula 2 into the compound represented by the above chemical formula 1, intermediate compounds INT.(b1), INT.(b2) and INT.(b3) were prepared by using the following reaction formulas 2-1, 2-2 and 2-3, respectively.

[0137] [Reaction 2-1]

[0138]

[0139] In reaction formula 2-1 above, X' is a halogen, and the explanations for the other substituents are the same as above. Step 2-1a is the step of introducing a bromine group into the starting material SM1(b1), and step 2-1b is the step of introducing a linking group through the Suzuki coupling reaction, thereby producing the intermediate compound INT.(b1). However, when L2 is a single bond, step 2-1b can be omitted. The specific manufacturing method is shown below.

[0140] 1) Step 2-1a: Preparation of intermediate compound SM2(b1)

[0141] SM1(b1) (1 equivalent) was dissolved in excess THF. The temperature was lowered to -78°C, and 2.5 M n-BuLi (1 equivalent) was added dropwise. After stirring for 3 hours, N-bromosuccinimide (1 equivalent) was added. The reaction mixture was then heated to room temperature and stirred for 10 hours. 1 N HCl (excess) was added to terminate the reaction. After the reaction was complete, the solvent was removed by chromatography, and the residue was subjected to silica gel column chromatography (ethyl acetate / hexane 1:15) to produce the title compound.

[0142] 2) Step 2-1b: Manufacturing of intermediate compound INT.(b1)

[0143] SM2(b1) (1 equivalent) and SM3 (1.02 equivalent) were added to tetrahydrofuran (excess), followed by the addition of 2M aqueous potassium carbonate solution (30 v / v relative to THF), and then tetra(triphenylphosphine)palladium (2 mol%). The mixture was heated and stirred for 10 hours. The temperature was lowered to room temperature, and after the reaction was stopped, the aqueous potassium carbonate solution was removed, and the mixture was subjected to layer separation. After solvent removal, the mixture was vacuum distilled and recrystallized from ethyl acetate and hexane to obtain the title compound.

[0144] [Reaction 2-2]

[0145]

[0146] In reaction formula 2-2 above, X' is a halogen, and the explanations for the other substituents are the same as above. Step 2-2a above is the step of introducing a bromine group into the starting material SM1(b2), and step 2-2b above is the step of introducing a linking group through the Suzuki coupling reaction, thereby producing the intermediate compound INT.(b2). However, when L2 is a single bond, step 2-2b can be omitted. The specific manufacturing method is as follows:

[0147] 1) Step 2-2a: Preparation of intermediate compound SM2(b2)

[0148] SM1(b2) (1 equivalent) was dissolved in excess DMF, and the temperature was lowered to 0°C. After the temperature stabilized, N-bromosuccinimide (1 equivalent) was added. Then, the reactants were heated to room temperature and stirred for 1 hour. Finally, 1N HCl (excess) was added to terminate the reaction. After the reaction was complete, the solvent was removed by chromatography, and the residue was subjected to silica gel column chromatography (ethyl acetate / hexane 1:15) to obtain the title compound.

[0149] 2) Step 2-2b: Preparation of intermediate compound INT.(b2)

[0150] In step 2-1b above, SM2(b2) was used instead of SM2(b1) as the starting material. Otherwise, the title compound was obtained by the same method as in step 2-1b above.

[0151] [Reaction 2-3]

[0152]

[0153] In reaction formula 2-3 above, X' is a halogen, and the explanations for the remaining substituents are the same as above. Step 2-3 above is the step of introducing a linking group through the Suzuki coupling reaction to produce the intermediate compound INT.(b3). At this time, the starting material SM1(b3) can be produced by methods known in journals such as "Potent and selective non-benzodioxole-containing endothelin-A receptor antagonists (Journal of Medicinal Chemistry, 1997, vol. 40, #3, pp. 322-330)" and "Zeolite-catalyzed synthesis of 2,3-unsubstituted benzo[b]furans via the intramolecular cyclization of 2-aryloxyacetaldehydeacetals (Tetrahedron, 2015, vol. 71, #29, pp. 4835-4841)". When L2 is a single bond, step 2-3 can be omitted. The specific manufacturing method is shown below.

[0154] 1) Steps 2-3: Preparation of intermediate compound INT.(b3)

[0155] In step 2-1b above, SM1(b3) was used instead of SM2(b1) as the starting material. Otherwise, the title compound was obtained by the same method as in step 2-1b above.

[0156] The intermediate compounds listed in Table 1 below were obtained using the methods described in reactions 2-1 to 2-3 above, and their respective yields and MS data are shown below.

[0157] [Table 1]

[0158]

[0159]

[0160]

[0161] Synthesis Example 2: Preparation of compounds 1 to 21 represented by chemical formula 1

[0162] The compound represented by the above chemical formula 1 was produced by the following reaction formula 1.

[0163] [Reaction Formula 1]

[0164]

[0165] In reaction formula 1 above, X' is independently a halogen, preferably bromine or chlorine, and the definitions of the remaining substituents are the same as described above. The specific manufacturing method is shown below.

[0166] 1) Step 1-1: Preparation of intermediate compounds INT.X (X1 to X21)

[0167] SM1 (1 equivalent), SM2 (1.02 equivalent), and sodium tert-butoxide (1.4 equivalent) were added to xylene, heated and stirred, and then refluxed. [bis(tri-tert-butylphosphine)]palladium (1 mol%) was added. The temperature was then lowered to room temperature, and after the reaction was complete, recrystallization was performed using tetrahydrofuran and ethyl acetate to obtain intermediate compounds X1 to X21 as shown in Table 2 below. Their yields and MS data are shown below.

[0168] [Table 2]

[0169]

[0170]

[0171]

[0172]

[0173] 2) Steps 1-2: Preparation of final compounds 1 to 21

[0174] Intermediate compound INT.X (1 equivalent), SM3 (1.02 equivalent), and sodium tert-butoxide (1.4 equivalent) were added to xylene, heated and stirred, and then refluxed. [bis(tri-tert-butylphosphine)]palladium (1 mol%) was added. The temperature was then lowered to room temperature, and after the reaction was completed, recrystallization was performed using tetrahydrofuran and ethyl acetate to obtain the final compounds 1 to 21 described below. Their yields and MS data are shown in Table 3.

[0175]

[0176]

[0177] [Table 3]

[0178]

[0179] Synthesis Example 3: Preparation of Compound 22 represented by Chemical Formula 1

[0180] The final compound 22, represented by the above chemical formula 1, was produced by the same substituents *-L2-B and *-L3-Ar via the following reaction formula 1'.

[0181] [Reaction 1']

[0182]

[0183] In the above reaction formula 1', X' is a halogen, preferably bromine or chlorine, and the definitions of the remaining substituents are the same as those described above. Specifically, the process was carried out in the same manner as step 1-1 of synthetic example 2, thereby obtaining the final compound 22 described above. The yield and MS data are shown in Table 4.

[0184] [Table 4]

[0185]

[0186] Example 1: OLED Manufacturing

[0187] ITO (Indium Tin Oxide) A glass substrate (Corning 7059 glass) with a thin film of ITO coating was immersed in distilled water containing a dispersant and washed using ultrasound. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for 10 minutes of ultrasonic washing. Following the distilled water washing, the substrate was then ultrasonically washed sequentially with isopropanol, acetone, and methanol, and then dried.

[0188] On the prepared ITO transparent electrode, HI-1 (hexanitrilehexaazatriphenylene) was applied... A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. Compound 1, synthesized in Synthesis Example 2, is then applied to the hole injection layer as a material for transporting holes. After vacuum evaporation, HT2 is then deposited onto the hole transport layer at a film thickness of [insert thickness here]. Vacuum evaporation is performed to form a hole-conditioning layer.

[0189] Then, on the aforementioned hole modulation layer, as a light-emitting layer, a compound of host BH1 and dopant BD1 (25:1) is applied... Vacuum evaporation is performed on the thickness.

[0190] Then, the E1 compound After forming the electronic conditioning layer by vapor deposition, E2 compound and Liq are vapor deposited in a 1:1 ratio (wt%). Thus, thermal vacuum evaporation was performed sequentially as both the electron injection and transport layers. On the aforementioned electron injection and transport layers, lithium fluoride (LiF) was sequentially deposited... The thickness, using aluminum The cathode is formed by vapor deposition of a certain thickness, thereby manufacturing organic light-emitting devices.

[0191] During the above process, the evaporation rate of organic matter is maintained. Lithium fluoride maintenance The evaporation rate of aluminum maintains The evaporation rate.

[0192] Examples 2 to 7 and Comparative Examples 1 to 3

[0193] The organic light-emitting device was manufactured by the same method as in Example 1 above, except that the compound described in Table 5 below was used instead of compound 1 used in the hole transport layer.

[0194] The compounds used in the above embodiments and comparative examples are shown below.

[0195]

[0196] Experimental Example 1

[0197] When current was applied to the organic light-emitting devices manufactured in Examples 1 to 7 and Comparative Examples 1 to 3 above, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 5 below. Here, T95 refers to the time required for the brightness to decrease from the initial brightness to 95%.

[0198] [Table 5]

[0199]

[0200] As shown in Table 5 above, it can be confirmed that the organic light-emitting device using the compound of the present invention as the hole transport layer material exhibits superior characteristics in terms of driving voltage, efficiency, and lifetime compared to the organic light-emitting device using the comparative example compound as the hole transport layer material, due to the smooth injection of holes into the light-emitting layer and the balance of holes and electrons in the organic light-emitting device based on the chemical structure.

[0201] Example 8: OLED Manufacturing

[0202] ITO (Indium Tin Oxide) A glass substrate (Corning 7059 glass) with a thin film of ITO was immersed in distilled water containing a dispersant and washed using ultrasound. The detergent used was from Fischer, and the distilled water was filtered twice using a Millipore filter. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for 10 minutes each time, followed by ultrasonic washing. After the distilled water washing, the substrate was ultrasonically washed sequentially with isopropanol, acetone, and methanol, and then dried.

[0203] On the prepared ITO transparent electrode, HI-1 (hexanitrilehexaazatriphenylene) was applied... A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. On this hole injection layer, HT1 [material missing] is used as a material to transport holes. After vacuum evaporation, compound 2 synthesized in synthesis example 2 is then applied to the hole transport layer to achieve a film thickness of [insert thickness here]. Vacuum evaporation is performed to form a hole conditioning layer.

[0204] Then, on the aforementioned hole modulation layer, as a light-emitting layer, a compound of host BH1 and dopant BD1 (25:1) is applied... Vacuum evaporation is performed on the thickness.

[0205] Then, the E1 compound After forming the electronic conditioning layer by vapor deposition, E2 compound and Liq are vapor deposited in a 1:1 ratio (wt%). Thus, thermal vacuum evaporation was performed sequentially as both the electron injection and transport layers. On the aforementioned electron injection and transport layers, lithium fluoride (LiF) was sequentially deposited... The thickness, using aluminum The cathode is formed by vapor deposition of a certain thickness, thereby manufacturing organic light-emitting devices.

[0206] During the above process, the evaporation rate of organic matter is maintained. Lithium fluoride maintenance The evaporation rate of aluminum maintains The evaporation rate.

[0207] Examples 9 to 29 and Comparative Examples 4 to 7

[0208] The organic light-emitting device was manufactured by the same method as in Example 8 above, except that the compounds listed in Table 6 below were used instead of compound HT1 used in the hole transport layer and compound 2 used in the hole modulation layer.

[0209] Experimental Example 2

[0210] When current was applied to the organic light-emitting devices manufactured in Examples 8 to 29 and Comparative Examples 4 to 7 above, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 6 below. Here, T95 refers to the time required for the brightness to decrease from the initial brightness to 95%.

[0211] [Table 6]

[0212]

[0213]

[0214] As shown in Table 6 above, it can be confirmed that organic light-emitting devices using the compounds of the present invention as hole conditioning layer materials or simultaneously as hole conditioning layer materials and hole transport layer materials exhibit superior characteristics in terms of driving voltage, efficiency, and lifetime compared to organic light-emitting devices using comparative example compounds, due to the smooth injection of holes into the light-emitting layer and the balance of holes and electrons in the organic light-emitting device based on the chemical structure.

[0215] [Symbol Explanation]

[0216] 1: Substrate 2: Anode

[0217] 3: Hole transport layer 4: Emissive layer

[0218] 5: Electron injection and transport layer; 6: Cathode

[0219] 7: Hole injection layer; 8: Hole regulation layer

[0220] 9: Electronic regulation layer.

[0221] The following content corresponds to the original claims in the parent application and is incorporated herein as part of the specification:

[0222] 1. A compound represented by the following chemical formula 1:

[0223] Chemical Formula 1

[0224]

[0225] In the chemical formula 1,

[0226] L1 to L3 are each an independent single bond; substituted or unsubstituted C 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 heteroaryl,

[0227] A is phenanthrene, triphenylene, dibenzofuranyl, or dibenzothiophene.

[0228] Wherein, A is not replaced, or is independently selected from C. 1-20 Alkyl; C 6-20 aryl; and C containing one or more heteroatoms selected from N, O, and S. 2-20 One or more substituents in a heteroaryl group are substituted.

[0229] B is a substituent represented by the following chemical formula 2.

[0230] Ar is a substituent represented by the following chemical formula 2; substituted or unsubstituted C 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0231] Chemical formula 2

[0232]

[0233] In the chemical formula 2,

[0234] X is O or S.

[0235] One of R1 to R3 is bonded to L2 or L3, and the others are independently hydrogen; deuterium; substituted or unsubstituted C. 1-60 Alkyl; substituted or unsubstituted C 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0236] However, when L2 or L3 binds to R1 or R2, the unbound R1 or R2 is not hydrogen.

[0237] n is an integer from 1 to 4.

[0238] 2. The compound according to item 1, wherein L1 to L3 are each independently a single bond, a phenylene group, a biphenyl dimethyl group, or a naphthylene group.

[0239] 3. The compound according to item 1, wherein A is represented by any one of the following chemical formulas a1 to a4:

[0240]

[0241] In the chemical formulas a1 to a4,

[0242] R can be either hydrogen or C independently. 6-20 Aryl.

[0243] 4. The compound according to item 1, wherein the substituent represented by chemical formula 2 is represented by any one of the following chemical formulas b1 to b3:

[0244]

[0245] In the chemical formulas b1 to b3,

[0246] X is O or S.

[0247] R1 and R2 are each independently C 1-10 Alkyl or C 6-20 Aryl,

[0248] R3 and R1' to R3' are each independently hydrogen and C. 1-10 Alkyl, C 6-20 aryl, or C containing heteroatoms O or S 2-20 Mixed aromatic compounds.

[0249] 5. The compound according to item 4, wherein, in the chemical formulas b1 and b2,

[0250] R1 is methyl, ethyl, phenyl, biphenyl, or naphthyl.

[0251] R2 is methyl, ethyl, phenyl, or biphenyl.

[0252] R3 can be hydrogen, methyl, or phenyl independently.

[0253] In the chemical formula b3,

[0254] R1' to R3' are each independently hydrogen, methyl, isopropyl, naphthyl, phenyl, or dibenzothiophene.

[0255] 6. The compound according to claim 1, wherein Ar is a substituent represented by the chemical formula 2; selected from any one aryl group chosen from phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, spiro[cyclopentane-1,9'-fluorenyl]yl and spiro[cyclohexane-1,9'-fluorenyl]yl; or selected from any one heteroaryl group chosen from dibenzofuranyl, dibenzothiophenyl and carbazoleyl.

[0256] In this embodiment, each of the aryl or heteroaryl groups is independently unsubstituted or independently selected from deuterium, C 1-10 Alkyl and C 6-20 One to five substituents in the aryl group are substituted.

[0257] 7. The compound according to item 6, wherein Ar is selected from any one of the following groups:

[0258]

[0259] In the group,

[0260] Y is O, S, N (phenyl) or C (methyl)2.

[0261] 8. The compound according to claim 1, wherein the compound is represented by any one of the following chemical formulas 1-1 to 1-6:

[0262]

[0263] In the chemical formulas 1-1 to 1-6,

[0264] The descriptions of L1 to L3, B, and Ar are the same as those in item 1.

[0265] Q is either O or S.

[0266] R is hydrogen, phenyl, or naphthyl.

[0267] 9. The compound according to claim 1, wherein the compound is selected from any one of the following compounds:

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274] 10. An organic light-emitting device, comprising: 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 a compound as described in any one of claims 1 to 9.

Claims

1. A compound represented by the following chemical formula 1: Chemical Formula 1 In the chemical formula 1, L1 and L3 are each independent single bonds; or C bonds that are either substituted with deuterium or not substituted. 6-60 Alpha-aryl L2 is a single bond, a phenylene group, or a naphthylene group. A is dibenzofuranyl or dibenzothiopheneyl. in, A is optionally defined by one or more Cs. 6-20 Aryl substitution, B is a substituent represented by the following chemical formula 2. Ar is selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, and fluorene. Ar is optionally and independently selected from deuterium and C. 1-10 Alkyl and C 6-20 One to five substituents in the aryl group are substituted. Chemical formula 2 In the chemical formula 2, X is O or S. One of R1 and R3 binds to L2, and the other is hydrogen; deuterium; C substituted or unsubstituted with deuterium. 1-60 Alkyl; C substituted or unsubstituted with deuterium 6-60 aryl; or deuterated or unsubstituted C containing a heteroatom selected from O and S. 2-60 Mixed aromatics, R2 represents hydrogen; deuterium; or C atoms that are substituted with or unsubstituted with deuterium. 1-60 Alkyl groups; or C groups that are deuterated or unsubstituted. 6-60 Aryl, However, when L2 combines with R1, R2 is not hydrogen. n is an integer from 1 to 4.

2. The compound according to claim 1, wherein, L1 and L3 are each independently a single bond, phenylene, biphenyl dimethyl, or naphthylene.

3. The compound according to claim 1, wherein, A can be represented by any one of the following chemical formulas a3 to a4: In the chemical formulas a3 and a4, R can be either hydrogen or C independently. 6-20 Aryl.

4. The compound according to claim 1, wherein, The substituent represented by chemical formula 2 is represented by any one of the following chemical formulas b1 and b3: In the chemical formulas b1 and b3, X is O or S. R2 is C 1-10 Alkyl or C 6-20 Aryl, R1' is hydrogen, C 1-10 Alkyl, C 6-20 aryl, or C containing heteroatoms O or S 2-20 Mixed aromatics, R3, R2', and R3' are each independently hydrogen and C. 1-10 Alkyl, or C 6-20 Aryl.

5. The compound according to claim 4, wherein, In the chemical formula b1, R2 is methyl, ethyl, phenyl, or biphenyl. R3 can be hydrogen, methyl, or phenyl independently. In the chemical formula b3, R1' can be hydrogen, methyl, isopropyl, naphthyl, phenyl, or dibenzothiophene. R2' and R3' can each be hydrogen, methyl, isopropyl, naphthyl, or phenyl.

6. The compound according to claim 1, wherein, Ar is selected from any one of the following groups: 。 7. The compound according to claim 1, wherein, The compound is represented by any one of the following chemical formulas 1-4 to 1-6: In the chemical formulas 1-4 to 1-6, The descriptions of L1 to L3, B, and Ar are the same as those in claim 1. Q is either O or S. In chemical formulas 1-4, R is hydrogen, phenyl, or naphthyl, while in chemical formulas 1-5 and 1-6, R is phenyl or naphthyl.

8. The compound according to claim 1, wherein, The compound is selected from any one of the following compounds: 。 9. An organic light-emitting device, wherein, include: First electrode; A second electrode disposed opposite to the first electrode; And an organic layer of one or more layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound of any one of claims 1 to 8.

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