Novel compounds and organic light-emitting devices containing the same

Abstract

The present invention relates to a novel compound and an organic light-emitting device containing the same.

Description

[Technical Field]

[0001] [Cross-reference of related applications] This application claims priority rights based on Korean Patent Application No. 10-2022-0149074 dated November 9, 2022, and Korean Patent Application No. 10-2023-0150901 dated November 3, 2023, and all content disclosed in the documents of said Korean Patent Applications is incorporated herein as part of this specification.

[0002] This invention relates to a novel compound and an organic light-emitting device containing the same. [Background technology]

[0003] Generally, organic luminescence refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices that utilize organic luminescence have a wide viewing angle, excellent contrast, and fast response time, and are highly regarded for their brightness, driving voltage, and response speed characteristics, leading to extensive research.

[0004] Organic light-emitting devices generally have a structure that includes a positive electrode, a negative electrode, and an organic layer between the positive and negative electrodes. To improve the efficiency and safety of the organic light-emitting device, the organic layer often consists of a multilayer structure composed 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, when a voltage is applied between the two electrodes, holes are injected from the positive electrode and electrons are injected from the negative electrode into the organic layer. When the injected holes and electrons meet, an exciton is formed, and light is emitted when this exciton returns to the ground state.

[0005] There is a continuous need for the development of new materials for the organic substances used in the aforementioned organic light-emitting devices. [Prior art documents] [Patent Documents]

[0006]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0007] The present invention relates to a novel organic light-emitting material and an organic light-emitting device containing the same.

Means for Solving the Problems

[0008] The present invention provides a compound represented by the following Chemical Formula 1:

Chemical Formula

[0009] In the Chemical Formula 1, Ar1 and Ar2 are each independently a substituted or unsubstituted C 6-60 aryl; or a C 2-60 heteroaryl containing any one or more selected from the group consisting of substituted or unsubstituted N, O, and S, Ar3 is a substituted or unsubstituted C 6-60 aryl, L is a single bond; a substituted or unsubstituted C 6-60 arylene; or a C 2-60 heteroarylene containing any one or more selected from the group consisting of substituted or unsubstituted N, O, and S, R1 to R8 are each independently hydrogen; deuterium; or a substituted or unsubstituted C 6-60 aryl, provided that any one of R1 to R8 is a substituted or unsubstituted phenyl, and any one or more of the rest are deuterium, R9 is hydrogen or deuterium, n is an integer of 1 to 3.

[0010] Furthermore, the present invention provides an organic light-emitting element comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain a compound represented by the chemical formula 1. [Effects of the Invention]

[0011] The compound represented by chemical formula 1 can be used as a material for the organic layer of an organic light-emitting device, and in the organic light-emitting device, it can improve efficiency, lower driving voltage, and / or improve lifetime characteristics. In particular, the compound represented by chemical formula 1 can be used as a light-emitting material. [Brief explanation of the drawing]

[0012] [Figure 1] This shows an example of an organic light-emitting element consisting of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. [Figure 2] This is an example of an organic light-emitting element consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, an electron blocking layer 8, a light-emitting layer 3, a hole blocking layer 9, an electron injection and transport layer 10, and a negative electrode 4. [Modes for carrying out the invention]

[0013] The present invention will be explained in more detail below for better understanding.

[0014] The present invention provides a compound represented by the chemical formula 1. In this specification, [ka] or [ka] This refers to a bond that is linked to another substituent.

[0015] In this specification, the term "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen groups; nitrile groups; nitro groups; hydroxyl groups; carbonyl groups; ester groups; imide groups; amino groups; phosphine oxide groups; alkoxy groups; aryloxy groups; alkylthiooxy groups; arylthiooxy groups; alkylsulfoxy groups; arylsulfoxy groups; silyl groups; boron groups; alkyl groups; cycloalkyl groups; alkenyl groups; aryl groups; aralkyl groups; aralkylkenyl groups; alkylaryl groups; alkylamine groups; aralkylamine groups; heteroarylamine groups; arylamine groups; arylphosphine groups; or heteroaryl groups containing one or more N, O, and S atoms, or substituted or unsubstituted with two or more substituents linked together from the substituents exemplified above. For example, "substituents with two or more substituents linked together" may be biphenyl groups. That is, a biphenyl group may be an aryl group and may be interpreted as a substituent with two phenyl groups linked together.

[0016] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the substituent has the following structure, but is not limited thereto. [ka]

[0017] In this specification, the ester group may be substituted with a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the substituents may be, but are not limited to, those shown in the following structural formulas. [ka]

[0018] In this specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, substituents may have the following structures, but are not limited thereto. [ka]

[0019] In this specification, the silyl group may specifically be, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like.

[0020] In this specification, the boron group may specifically be a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, or the like, but is not limited to these.

[0021] In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0022] In this 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. In one embodiment, the alkyl group has 1 to 20 carbon atoms. In another embodiment, the alkyl group has 1 to 10 carbon atoms. In yet another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of alkyl groups include, but are not limited to, 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.

[0023] In this 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. In one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. In another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. In yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples include, but are not limited to, 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, stilbenyl group, styrenyl group, etc.

[0024] In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. In one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

[0025] In this specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. In one embodiment, the aryl group has 6 to 30 carbon atoms. In another embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, a phenanthryl group, a pyrenyl group, a perilenyl group, a chrysenyl group, a fluorenyl group, etc., but is not limited thereto.

[0026] In this specification, the fluorenyl group may be substituted, and two substituents can bond to each other to form a spiro structure. When the fluorenyl group is substituted, [ka] Other examples are also acceptable, however, they are not limited to these.

[0027] In this specification, the heteroaryl group is a heteroaryl group containing one or more heteroatoms from O, N, Si, and S, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. In one embodiment, the number of carbon atoms of the heteroaryl group is 6 to 30. In another embodiment, the number of carbon atoms of the heteroaryl group is 6 to 20. Examples of heteroaryl groups include, but are not limited to, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidine, triazine, acridyl, pyridazine, pyrazinyl, quinolinyl, quinazoline, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyradinyl, pyrazinopyradinyl, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazole, phenothiazinyl, and dibenzofuranyl.

[0028] In this specification, the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In this specification, the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the example of the alkyl group described above. In this specification, the heteroaryl among the heteroarylamine is the same as the description of the heteroaryl group described above. In this specification, the alkenyl group among the aralkenyl group is the same as the example of the alkenyl group described above. In this specification, the aryl group among the aralkenyl group is the same as the example of the alkenyl group described above. In this specification, the aryl group among the aralkyl group is the same as the description of the aryl group described above. In this specification, the aryl group among the aralkyl group is the same as the example of the alkenyl group described above. In this specification, the aryl group among the aralkenyl group is the same as the description of the heteroaryl group described above.

[0029] Preferably, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-20 An aryl; or a C containing one or more selected from the group consisting of substituted or unsubstituted N, O, and S. 2-20 Heteroaryl compounds are also acceptable.

[0030] More preferably, Ar1 and Ar2 may each independently be phenyl, biphenylyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl, and each of Ar1 and Ar2 may independently be unsubstituted or substituted with one or more deuterium atoms.

[0031] Most preferably, Ar1 and Ar2 may each be independently selected from the group consisting of the following: [ka]

[0032] Preferably, Ar3 is a substituted or unsubstituted C 6-20 aryl.

[0033] More preferably, Ar3 is phenyl which is unsubstituted or substituted with 1 to 5 deuteriums; or biphenylyl which is unsubstituted or substituted with 1 to 9 deuteriums.

[0034] More preferably, Ar3 may be phenyl, phenyl substituted with 5 deuteriums, biphenylyl, or biphenylyl substituted with 9 deuteriums.

[0035] Preferably, L is a single bond; a substituted or unsubstituted C 6-20 arylene; or a C 2-20 heteroarylene containing any one or more selected from the group consisting of substituted or unsubstituted N, O, and S.

[0036] More preferably, L may be a single bond.

[0037] Preferably, R1 to R8 are each independently hydrogen; deuterium; or a substituted or unsubstituted C 6-20 aryl, but any one of R1 to R8 is a substituted or unsubstituted phenyl, and any one or more of the rest may be deuterium.

[0038] More preferably, R1 to R8 are each independently hydrogen; deuterium; or a substituted or unsubstituted C 6-20 aryl, but any one of R1 to R8 is a phenyl which is unsubstituted or substituted with 1 to 5 deuteriums, and any one or more of the rest may be deuterium.

[0039] More preferably, R1 to R8 are each independently hydrogen; deuterium; or substituted or unsubstituted phenyl, wherein one of R1 to R8 is unsubstituted or phenyl substituted with 1 to 5 deuterium atoms, and one or more of the remaining atoms are deuterium.

[0040] More preferably, R1 to R8 are each independently hydrogen; deuterium; or substituted or unsubstituted C 6-20 Although it is an aryl group, one of R1 to R8 is phenyl or phenyl substituted with five deuterium atoms, and one or more of the remaining atoms may be deuterium.

[0041] More preferably, R1 to R8 are each independently hydrogen; deuterium; or substituted or unsubstituted phenyl, wherein one of R1 to R8 is phenyl or phenyl substituted with five deuterium atoms, and one or more of the remaining atoms are deuterium.

[0042] Most preferably, one of R1 to R8 is phenyl or phenyl substituted with five deuterium atoms, and the rest may be deuterium atoms.

[0043] Preferably, R1 is either unsubstituted or phenyl with 1 to 5 deuterium atoms, and one or more of R2 to R8 are deuterium atoms; R2 is an unsubstituted or deuterium-substituted phenyl compound, and one or more of R1 and R3-R8 are deuterium; R3 is an unsubstituted or deuterium-substituted phenyl, and one or more of R1, R2 and R4-R8 are deuterium; or R4 is an unsubstituted or deuterium-substituted phenyl compound, and one or more of R1-R3 and R5-R8 may be deuterium.

[0044] more, R1 is either unsubstituted or phenyl substituted with 1 to 5 deuterium atoms, and R2 to R8 are deuterium atoms; R2 is either unsubstituted or phenyl substituted with 1 to 5 deuterium atoms, and R1 and R3-R8 are deuterium atoms; R3 is an unsubstituted or deuterium-substituted phenyl, and R1, R2 and R4-R8 are deuterium; or R4 is an unsubstituted or deuterium-substituted phenyl compound, and R1-R3 and R5-R8 may be deuterium compounds.

[0045] Most preferably, R1 is either unsubstituted or phenyl substituted with five deuterium atoms, and R2-R8 are deuterium atoms; R2 is either unsubstituted or phenyl substituted with five deuterium atoms, and R1 and R3-R8 are deuterium atoms; R3 is an unsubstituted or five deuterium-substituted phenyl, and R1, R2 and R4-R8 are deuterium; or R4 is an unsubstituted or five-deuterium substituted phenyl compound, and R1-R3 and R5-R8 may be deuterium compounds.

[0046] Typical examples of compounds represented by the aforementioned chemical formula 1 are as follows:

[0047] [ka]

[0048] [ka]

[0049] [ka]

[0050] [ka]

[0051] [ka]

[0052] [ka]

[0053] [ka]

[0054] [ka]

[0055] [ka]

[0056] [ka]

[0057] The compound represented by the aforementioned chemical formula 1 can be produced, for example, by the manufacturing method shown in reaction equation 1 below, and the remaining compounds can be produced in a similar manner. [ka]

[0058] In the above reaction formula 1, Ar1 to Ar3, L, R1 to R9 and n are the same as those defined in the above chemical formula 1, and X is a halogen, preferably X is fluorine, chloro or bromo.

[0059] The reaction 1 described above is preferably carried out as an amine substitution reaction in the presence of a palladium catalyst and a base, and the reactive group for the amine substitution reaction can be changed as is known in the art. The production method can be further elaborated in the production examples described later.

[0060] Furthermore, the present invention provides an organic light-emitting device comprising a compound represented by the chemical formula 1. As an example, the present invention provides an organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by the chemical formula 1.

[0061] The organic layer of the organic light-emitting element of the present invention may have a tomographic structure, but it may also have a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure in which the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and so on. However, the structure of the organic light-emitting element is not limited to this and may include fewer organic layers.

[0062] Furthermore, the organic layer may include a light-emitting layer, and the light-emitting layer may include a compound represented by the chemical formula 1.

[0063] Furthermore, the organic layer may include a hole transport layer, a hole injection layer, or a layer that performs both hole transport and hole injection simultaneously, and the hole transport layer, hole injection layer, or layer that performs both hole transport and hole injection simultaneously may include the compound represented by chemical formula 1.

[0064] Furthermore, the organic layer may include an electron transport layer, an electron injection layer, or an electron injection and transport layer, and the electron transport layer, electron injection layer, or electron injection and transport layer may include a compound represented by chemical formula 1.

[0065] Furthermore, the organic light-emitting element according to the present invention may be an organic light-emitting element with a normal type structure in which a positive electrode, one or more organic layers, and a negative electrode are sequentially stacked on a substrate. Alternatively, the organic light-emitting element according to the present invention may be an inverted type structure in which a negative electrode, one or more organic layers, and a positive electrode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting element according to one embodiment of the present invention is illustrated in Figures 1 and 2.

[0066] Figure 1 shows an example of an organic light-emitting element consisting of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. Figure 2 shows an example of an organic light-emitting element consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, an electron barrier layer 8, a light-emitting layer 3, a hole blocking layer 9, an electron injection and transport layer 10, and a negative electrode 4. In such a structure, the compound represented by chemical formula 1 may be included in the compound layer.

[0067] The organic light-emitting element according to the present invention is manufactured using materials and methods known in the art, except that one or more of the organic layers contain a compound represented by the chemical formula 1. Furthermore, if the organic light-emitting element includes multiple organic layers, the organic layers may be formed from the same substance or different substances.

[0068] For example, the organic light-emitting element 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, a positive electrode can be formed by depositing a metal or a conductive metal oxide, or an alloy thereof, onto the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation. An organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer can then be formed on top of the positive electrode, and finally, a material that can be used as a negative electrode can be deposited on top of that. In addition to this method, an organic light-emitting element can also be made by sequentially depositing the negative electrode material, the organic layer, and the positive electrode material onto the substrate.

[0069] Furthermore, the compound represented by chemical formula 1 can be formed as an organic layer not only by vacuum deposition during the manufacture of organic light-emitting devices but also by solution coating methods. Here, solution coating methods include, but are not limited to, spin coating, dip coating, doctor blade, inkjet printing, screen printing, spray method, and roll coating.

[0070] In addition to this method, organic light-emitting diodes can also be manufactured by sequentially depositing a negative electrode material, an organic layer, and a positive electrode material onto a substrate (WO2003 / 012890). However, the manufacturing method is not limited to this.

[0071] For example, the first electrode is a positive electrode and the second electrode is a negative electrode, or the first electrode is a negative electrode and the second electrode is a positive electrode.

[0072] As the positive electrode material, a material with a large work function is preferred so that hole implantation into the organic layer proceeds smoothly. Specific examples of the positive electrode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

[0073] The anode material is preferably a material with a small work function so that electron injection into the organic layer is easily facilitated. Specific examples of the anode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer materials such as LiF / Al or LiO2 / Al.

[0074] The hole injection layer is a layer into which holes are injected from the electrode. The hole injection material is preferably a compound that has the ability to transport holes, has a hole injection effect at the positive electrode, has an excellent hole injection effect on the light-emitting layer or light-emitting material, prevents the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material, and has excellent thin-film formation ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile-hexazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and polyaniline and polythiophene-based conductive polymers.

[0075] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is a material that can receive holes from the positive electrode or hole injection layer and transfer them to the light-emitting layer, and is suitable if it has high mobility for holes. Specific examples include arylamine-based organic compounds, conductive polymers, and block copolymers in which conjugated and unconjugated parts are present together, but the material is not limited to these. For example, if two or more hole transport materials are used, they can be mixed and used, or the first, second, and subsequent hole transport layers can be manufactured without mixing.

[0076] The electron-blocking layer is a layer placed between the hole transport layer and the light-emitting layer to prevent electrons injected from the negative electrode from being recombined in the light-emitting layer and instead passing to the hole transport layer. It is sometimes called an electron-suppressing layer. A material with a lower electron affinity than the electron transport layer is preferred for the electron-blocking layer.

[0077] The aforementioned light-emitting material is a material that can emit light in the visible light region by transporting and combining holes and electrons from a hole transport layer and an electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence and phosphorescence. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complexes (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole, and benzoimidazole compounds; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc.

[0078] The light-emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocycle-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluorantene compounds, etc., and heterocycle-containing compounds include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc. Preferably, the compound represented by chemical formula 1 can be used as a host. The compound represented by chemical formula 1 can be used as a cohost together with other host substances.

[0079] Examples of dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluorantene compounds, and metal complexes. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, chrysene, and perifurantene, which have arylamino groups. Styrylamine compounds are compounds in which at least one arylvinyl group is substituted onto a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamino groups are substituted or unsubstituted. Specifically, examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. Examples of metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0080] The aforementioned hole blocking layer is a layer placed between the electron transport layer and the light-emitting layer to prevent holes injected from the positive electrode from passing to the electron transport layer without being recombined in the light-emitting layer, and is sometimes called a hole suppression layer. A material with a high ionization energy is preferred as the hole blocking layer.

[0081] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. Suitable electron transport materials are those that can readily receive electron injections from the negative electrode and transfer them to the light-emitting layer, and that have high electron mobility. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material, as used in conventional techniques. In particular, suitable cathode materials are ordinary materials with a low work function followed by an aluminum or silver layer. Specifically, these include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0082] The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an excellent electron injection effect from the negative electrode and an excellent electron injection effect on the light-emitting layer or light-emitting material, prevents the movement of excitons generated in the light-emitting layer to the hole injection layer, and is preferably a compound with excellent thin-film formation ability. Specifically, this includes, but is not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0083] Examples of the aforementioned metal complex compounds include, but are not limited to, 8-hydroxyquinolina tritium, bis(8-hydroxyquinolina)zinc, bis(8-hydroxyquinolina)copper, bis(8-hydroxyquinolina)manganese, tris(8-hydroxyquinolina)aluminum, tris(2-methyl-8-hydroxyquinolina)aluminum, tris(8-hydroxyquinolina)gallium, bis(10-hydroxybenzo[h]quinolina)beryllium, bis(10-hydroxybenzo[h]quinolina)zinc, bis(2-methyl-8-quinolina)chlorogallium, bis(2-methyl-8-quinolina)(o-crezolat)gallium, bis(2-methyl-8-quinolina)(1-naphthorato)aluminum, and bis(2-methyl-8-quinolina)(2-naphthorato)gallium.

[0084] On the other hand, in the present invention, the "electron injection and transport layer" is a layer that performs both the electron injection layer and the electron transport layer, and the materials that perform each of the layers may be used individually or in combination, but are not limited thereto.

[0085] The organic light-emitting element according to the present invention is a bottom emission element, a top emission element, or a double-sided light-emitting element, and may be a bottom emission element in which a relatively high luminous efficiency is required.

[0086] Furthermore, the compound represented by chemical formula 1 may be included not only in organic light-emitting devices but also in organic solar cells or organic transistors.

[0087] The present invention will be described in more detail below to aid in understanding it. However, the following examples are for illustrative purposes only, and the content of the present invention is not limited to the following examples. [Examples]

[0088] [Manufacturing example] Manufacturing Example 1: Manufacturing of Compound GH1 [ka]

[0089] (Manufacturing Example 1-1) Manufacturing of Compound 1(a)P-1 Under a nitrogen atmosphere, 1-bromo-9H-carbazole (50 g, 203.2 mmol) and TfOH (10 ml) were placed in C6D6 (500 ml) and stirred at 40°C for 4 hours. After the reaction was complete, the mixture was cooled to room temperature, and D2O (100 ml) was added and stirred for 30 minutes, after which trimethylamine (12 ml) was added dropwise. The reaction mixture was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried over MgSO4 and recrystallized with ethanol to obtain 44.5 g of compound 1(a)P-1. (Yield 87%, MS[M+H]) + =254)

[0090] (Manufacturing Example 1-2) Manufacturing of Compound 1(a) Under a nitrogen atmosphere, compound 1(a)P-1 (30 g, 118.5 mmol) and phenylboronic acid (14.4 g, 118.5 mmol) were added to 600 ml of tetrahydrofuran and stirred under reflux. Then, potassium carbonate (49.1 g, 355.5 mmol) dissolved in 49 ml of water was added and stirred thoroughly, followed by the addition of tetrakistriphenyl-phosphinopalladium (4.1 g, 3.6 mmol). After 2 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered off. The solid was dissolved in 1483 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound 1(a) (21.4 g, 72%, MS:[M+H]). + They manufactured (=251.4)

[0091] [ka]

[0092] (Manufacturing Examples 1-3) Manufacturing of Compound GH1P-1 Under a nitrogen atmosphere, 2-([1,1'-biphenyl]-3-yl)-4-3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazine (30 g, 68.5 mmol) and (phenyl-d5)boronic acid (8.7 g, 68.5 mmol) were added to 600 ml of tetrahydrofuran and stirred under reflux. Then, potassium carbonate (28.4 g, 205.5 mmol) dissolved in 28 ml of water was added and stirred thoroughly. Tetrakistriphenyl-phosphinopalladium (2.4 g, 2.1 mmol) was added. After the reaction for 2 hours, the mixture was cooled to room temperature and the resulting solid was filtered off. The solid was dissolved in 1660 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, then the mixture was filtered and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound GH1P-1 (22.9g, 69%, MS:[M+H]). + They manufactured (=485.6).

[0093] (Manufacturing Examples 1-4) Manufacturing of Compound GH1 Under a nitrogen atmosphere, GH1P-1 (30 g, 61.9 mmol) and 1(a) (15.5 g, 61.9 mmol) were added to 600 ml of tetrahydrofuran and stirred under reflux. Then, potassium carbonate (25.7 g, 185.7 mmol) dissolved in 26 ml of water was added and stirred thoroughly, followed by the addition of tetrakistriphenyl-phosphinopalladium (2.1 g, 1.9 mmol). After 2 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered off. The solid was dissolved in 2213 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound GH1 (26.1 g, 59%, MS:[M+H]). + They manufactured (=715.9).

[0094] Manufacturing Example 2: Manufacturing of Compound GH2 [ka]

[0095] (Manufacturing Example 2-1) Manufacturing of Compound 2(a) Except for using (phenyl-d5)boronic acid instead of phenylboronic acid, the white solid compound 2(a) (22.4g, 74%, MS:[M+H]) was prepared in the same manner as in Preparation Example 1-2. + They manufactured (=256.4).

[0096] [ka]

[0097] (Production Example 2-2) Production of Compound GH2P-1 Except for using 2-(3-chloro-4-fluorophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-3-yl)-4-(3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazine and (phenyl-d5)boronic acid instead of (phenyl-d5)boronic acid, a white solid compound GH2P-1 (25.2g, 77%, MS:[M+H]) was prepared in the same manner as in Preparation Examples 1-3, except that 2-(3-chloro-4-fluorophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine was used and (phenyl-d5)boronic acid was used instead of (phenyl-d5)boronic acid. + They manufactured (=494.5).

[0098] (Manufacturing Example 2-3) Manufacturing of Compound GH2 The yellow solid compound GH2 (29.7g, 67%, MS:[M+H]) was prepared in the same manner as in Preparation Examples 1-4, except that compound GH2P-1 was used instead of compound GH1P-1 and compound 2(a) was used instead of compound 1(a). + They manufactured (=729.9).

[0099] Manufacturing Example 3: Manufacturing of Compound GH3

[0100] [ka]

[0101] (Manufacturing Example 3-1) Manufacturing of Compound 3(a)P-1 Except for using 2-bromo-9H-carbazole instead of 1-bromo-9H-carbazole, the white solid compound 3(a)P-1 (42.5 g, yield 83%, MS[M+H]) was prepared in the same manner as in Preparation Example 1-1. + They manufactured (=254).

[0102] (Manufacturing Example 3-2) Manufacturing of Compound 3(a) Except for using compound 3(a)P-1 instead of compound 2(a)P-1, the same method as in Preparation Example 2-2 was used to prepare a white solid compound 3(a) (20.6g, 68%, MS:[M+H]+ They manufactured (=256.4).

[0103] [ka]

[0104] (Manufacturing Example 3-3) Manufacturing of Compound GH3P-1 Except for using 2-(3-chloro-4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-3-yl)-4-(3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazine, a white solid compound GH3P-1 (16.2g, 66%, MS:[M+H]) was prepared in the same manner as in Preparation Examples 1-3. + They manufactured (=404.5).

[0105] (Manufacturing Example 3-4) Manufacturing of Compound GH3 The yellow solid compound GH3 (28g, 59%, MS:[M+H]) was prepared in the same manner as in Preparation Example 1-4, except that compound GH3P-1 was used instead of compound GH1P-1 and compound 3(a) was used instead of compound 1(a). + They manufactured (=639.8).

[0106] Manufacturing Example 4: Manufacturing of Compound GH4 [ka]

[0107] (Manufacturing Example 4-1) Manufacturing of Compound 4(a) Except for using phenylboronic acid instead of (phenyl-d5)boronic acid, the white solid compound 4(a) (23.4g, 79%, MS:[M+H]) was prepared in the same manner as in Preparation Example 3-2. + They manufactured (=251.4)

[0108] [ka]

[0109] (Manufacturing Example 4-2) Manufacturing of Compound GH4P-1 Except for using 2-(3-chloro-4-fluorophenyl)-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-3-yl)-4-(3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazine and using phenylboronic acid instead of (phenyl-d5)boronic acid, a white solid compound GH4P-1 (26.4g, 80%, MS:[M+H]) was prepared in the same manner as in Preparation Examples 1-3. + They manufactured (=515.6).

[0110] (Manufacturing Example 4-3) Manufacturing of Compound GH4 The yellow solid compound GH4 (28.7g, 66%, MS:[M+H]) was prepared in the same manner as in Preparation Examples 1-4, except that compound GH4P-1 was used instead of compound GH1P-1 and compound 4(a) was used instead of compound 1(a). + They manufactured (=746).

[0111] Manufacturing Example 5: Manufacturing of Compound GH5 [ka]

[0112] (Manufacturing Example 5-1) Manufacturing of Compound 5(a)P-1 Except for using 3-bromo-9H-carbazole instead of 1-bromo-9H-carbazole, the white solid compound 3(a)P-1 (46.1 g, yield 90%, MS[M+H]) was prepared in the same manner as in Preparation Example 1-1. + They manufactured (=254).

[0113] (Manufacturing Example 5-2) Manufacturing of Compound 5(a) Except for using compound 5(a)P-1 instead of compound 2(a)P-1, a white solid compound 5(a) (21.8g, 72%, MS:[M+H]) was prepared in the same manner as in Preparation Example 2-2. + They manufactured (=256.4).

[0114] [ka]

[0115] (Manufacturing Example 5-3) Manufacturing of Compound GH5P-1 Except for using 2-(3-chloro-4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-3-yl)-4-(3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazine, the white solid compound GH5P-1 (23g, 68%, MS:[M+H]) was prepared in the same manner as in Preparation Examples 1-3. + They manufactured (=409.5).

[0116] (Manufacturing Example 5-4) Manufacturing of Compound GH5 The yellow solid compound GH5 (24.1g, 51%, MS:[M+H]) was prepared in the same manner as in Preparation Example 1-4, except that compound GH5P-1 was used instead of compound GH1P-1 and compound 5(a) was used instead of compound 1(a). + They manufactured (=644.9).

[0117] Manufacturing Example 6: Manufacturing of Compound GH6 [ka]

[0118] (Production Example 6-1) Production of Compound GH6P-1 Except for using 2-([1,1'-biphenyl]-4-yl)-4-(3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-3-yl)-4-(3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazine, a white solid compound GH6P-1 (21.2 g, 64%, MS:[M+H]) was prepared in the same manner as in Preparation Examples 1-3. + They manufactured (=485.6).

[0119] (Manufacturing Example 6-2) Manufacturing of Compound GH6 The yellow solid compound GH6 (24.8g, 56%, MS:[M+H]) was prepared in the same manner as in Preparation Example 1-4, except that compound GH6P-1 was used instead of compound GH1P-1 and compound 6(a) was used instead of compound 1(a). + They manufactured (=715.9).

[0120] (Manufacturing Example 7) Manufacturing of compound GH7 [ka]

[0121] (Production Example 7-1) Production of Compound GH7P-1 Except for using 4-bromo-1,1'-biphenyl instead of (phenyl-d5)boronic acid, the white solid compound GH7P-1 (27.8g, 70%, MS:[M+H]) was prepared in the same manner as in Preparation Example 5-3. + They manufactured (=480.6).

[0122] (Manufacturing Example 7-2) Manufacturing of Compound GH7 The yellow solid compound GH6 (23.7g, 53%, MS:[M+H]) was prepared in the same manner as in Preparation Example 1-4, except that compound GH7P-1 was used instead of compound GH1P-1 and compound 5(a) was used instead of compound 1(a). + They manufactured (=715.9).

[0123] (Manufacturing Example 8) Manufacturing of Compound GH8 [ka]

[0124] (Production Example 8-1) Production of Compound GH8P-1 Except for using 9-(4-(3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole instead of 2-(3-chloro-4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine, a white solid compound GH8P-1 (22.2 g, 67%, MS:[M+H]) was prepared in the same manner as in Preparation Example 5-3. + They manufactured (=498.6).

[0125] (Manufacturing Example 8-2) Manufacturing of Compound GH8 The yellow solid compound GH8 (22.5g, 51%, MS:[M+H]) was prepared in the same manner as in Preparation Example 1-4, except that compound GH8P-1 was used instead of compound GH1P-1 and compound 5(a) was used instead of compound 1(a). + They manufactured (=734).

[0126] Manufacturing Example 9: Manufacturing of Compound GH9 [ka]

[0127] (Production Example 9-1) Production of Compound 9(a)P-1 Except for using 4-bromo-9H-carbazole instead of 1-bromo-9H-carbazole, the white solid compound 9(a)P-1 (43.9g, yield 86%, MS[M+H]) was prepared in the same manner as in Preparation Example 1-1. + They manufactured (=254).

[0128] (Production Example 9-2) Production of Compound 9(a) Except for using compound 9(a)P-1 instead of compound 1(a)P-1 and phenylboronic acid instead of (phenyl-d5)boronic acid, a white solid compound 9(a) (20.5g, 69%, MS:[M+H]) was prepared in the same manner as in Preparation Example 2-2. + They manufactured (=251.4)

[0129] [ka]

[0130] (Production Example 9-3) Production of Compound GH9 The yellow solid compound GH9 (24g, 51%, MS:[M+H]) was prepared in the same manner as in Preparation Example 3-4, except that compound 9(a) was used instead of compound 3(a). + They manufactured (=634.8).

[0131] Manufacturing Example 10: Manufacturing of Compound GH10 [ka]

[0132] (Manufacturing Example 10-1) Manufacturing of Compound 10(a) Except for using (phenyl-d5)boronic acid instead of phenylboronic acid, the white solid compound 10(a) (21.5g, 71%, MS:[M+H]) was prepared in the same manner as in Preparation Example 9-1. + They manufactured (=256.4). [ka]

[0133] (Production Example 10-2) Production of Compound GH10P-1 Except for using 2-(3-chloro-4-fluorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine instead of 2-(3-chloro-4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine, the white solid compound GH10P-1 (24.2g, 74%, MS:[M+H]) was prepared in the same manner as in Preparation Example 3-3. + They manufactured (=494.5).

[0134] (Manufacturing Example 10-3) Manufacturing of Compound GH10 The yellow solid compound GH10 (27.5g, 62%, MS:[M+H]) was prepared in the same manner as in Preparation Example 3-4, except that compound 10(a) was used instead of compound 3(a) and compound GH10P-1 was used instead of compound GH3P-1. + They manufactured (=729.9).

[0135] [Examples] (Example 1) A glass substrate coated with a 100 nm thick ITO (indium tin oxide) film was ultrasonically cleaned in distilled water containing detergent. Fischer Co. detergent was used, and distilled water that had been secondarily filtered through a Millipore Co. filter was used. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes each time. After the distilled water cleaning, ultrasonic cleaning was performed again with isopropyl alcohol, acetone, and methanol solvents, followed by drying and transport to a plasma cleaning machine. Alternatively, the substrate was cleaned using oxygen plasma for 5 minutes before being transported to a vacuum deposition apparatus.

[0136] A hole injection layer was formed on the prepared ITO transparent electrode by thermal vacuum deposition of the following compound HI-A to a thickness of 60 nm.

[0137] A first hole transport layer with a thickness of 5 nm was formed by vacuum deposition of the compound HAT described below onto the hole injection layer, and a second hole transport layer with a thickness of 50 nm was formed by vacuum deposition of the compound HT-A described below onto the first hole transport layer.

[0138] An electron-blocking layer was formed on the hole transport layer by thermal vacuum deposition of the compound HT-B to a thickness of 45 nm. On the electron-blocking layer, the previously prepared compound GH1 was mixed with the compound GH-H in a 1:1 weight ratio, and then vacuum-deposited with the compound GD in a 90:10 weight ratio to a thickness of 40 nm to form an emissive layer. On the emissive layer, a hole-blocking layer was formed by vacuum-depositing the compound ET-A to a thickness of 5 nm. On the hole-blocking layer, an electron-injection and transport layer with a thickness of 35 nm was formed by vacuum-depositing the compound ET-B and the compound LiQ in a 1:1 weight ratio.

[0139] After depositing lithium fluoride (LiF) to a thickness of 1 nm onto the electron injection and transport layer, aluminum was subsequently deposited to a thickness of 100 nm to form a negative electrode, thereby manufacturing an organic light-emitting element.

[0140] [ka]

[0141] During the process described above, the deposition rate of organic materials was maintained at 0.04 nm / sec to 0.09 nm / sec, the deposition rate of lithium fluoride was maintained at 0.03 nm / sec, and the deposition rate of aluminum was maintained at 0.2 nm / sec. The vacuum level during deposition was 1 × 10⁻⁶. -7 torr~5×10 -5 Torr was maintained.

[0142] (Examples 2-10 and Comparative Examples 1-6) An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds listed in Table 1 below were used instead of compound 1.

[0143] In Table 1 below, the structures of compounds GHA to GHF are as follows: [ka]

[0144] [Example of experiment] Current was applied to the organic light-emitting elements fabricated in Examples 1 to 10 and Comparative Examples 1 to 6, and the voltage, efficiency, emission color, and lifetime (T95) were measured. The results are shown in Table 1 below. At this time, the voltage and efficiency were 10 mA / cm². 2 The current density was applied and measured, and T95 measured a current density of 20 mA / cm². 2 This refers to the time (hr) until the initial brightness decreases to 95%.

[0145] [Table 1]

[0146] The compound represented by Chemical Formula 1 of the present invention is designed in such a way that steric hindrance is induced by introducing a substituted / unsubstituted phenyl group at the Ar3 position, resulting in a twisted structure between the triazine and carbazole portions. In this case, the electron-donating properties of the carbazole substituent increase the overall molecular stability, and the electron distribution is separated, resulting in additional charge transfer (CT) properties, which in turn leads to an improvement in voltage / efficiency characteristics.

[0147] However, in this case, there is a high possibility that molecular stability problems will arise due to the electron deficiency phenomenon of the carbazole substituent. To solve this, we were able to confirm that substituting deuterium into the carbazole substituent had a significantly greater effect on increasing the lifetime compared to other parts. Furthermore, by introducing additional phenyl groups, we were able to improve efficiency and lifetime by adjusting the electron distribution and balance.

[0148] In Comparative Example 1, the absence of a substituent at the Ar3 position of chemical formula 1 resulted in a flat overall molecular structure, confirming that the aforementioned effect could not be achieved. In Comparative Example 4, the phenyl group was introduced at a different position, resulting in insufficient steric hindrance and thus a failure to demonstrate a sufficient improvement effect. In Comparative Example 5, the substitution of an additional carbazole group with the carbazole group prevented the electron-donating role of the carbazole substituent from being fully realized, leading to a decrease in efficiency and lifetime. It was found that when a heterocycle such as a carbazole group is added to carbazole, it directly affects the electronic properties of the original carbazole substituent, resulting in inferior physical properties when applied to organic light-emitting devices. In Comparative Example 6, a fluorene substituent was introduced, but it was confirmed that not only was insufficient steric hindrance not provided to the carbazole group, but the stability of the fluorene substituent decreased, leading to a sharp decline in lifetime. [Explanation of Symbols]

[0149] 1: Circuit board 2: Positive electrode 3: Emitting layer 4: Negative electrode 5: Hole injection layer 6: First hole transport layer 7: Second hole transport layer 8: Electron barrier layer 9: Hole blocking layer 10: Electron injection and transport layer

Claims

1. The compound represented by the following chemical formula 1: 【Chemistry 1】 In the aforementioned chemical formula 1, Ar １ and Ar ２ These are, independently, substitutional or non-substitutional C. ６－６０ A C comprising one or more elements selected from the group consisting of aryl, substituted or unsubstituted N, O, and S. ２－６０ It is a heteroaryl, Ar ３ C is either substituted or non-substituted. ６－６０ It is Ariel, L is a single bond; or C is substituted or unsubstituted. ６－６０ It is arrine, R １ ~R ８ Any one of them is phenyl which is unsubstituted or substituted with 1 to 5 deuteriums, and the rest are deuteriums, R ９ is hydrogen or deuterium, n is an integer between 1 and 3.

2. Ar １ and Ar ２ These are, independently, phenyl, biphenylyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl, The Ar １ and Ar ２ The compound according to claim 1, wherein each of the elements is independently unsubstituted or substituted with one or more deuterium atoms.

3. Ar １ and Ar ２ The compound according to claim 1, wherein each is independently selected from the group consisting of the following. 【Chemistry 2】

4. Ar ３ The compound according to claim 1, wherein is an unsubstituted or deuterium-substituted phenyl; or an unsubstituted or deuterium-substituted biphenylyl.

5. The compound according to claim 1, wherein L is a single bond.

6. R １ However, it is an unsubstituted or deuterium-substituted phenyl, R ２ ~R ８ Is it deuterium? R ２ However, it is an unsubstituted or deuterium-substituted phenyl, R １ and R ３ ~R ８ Is it deuterium? R ３ However, it is an unsubstituted or deuterium-substituted phenyl, R １ , R ２ and R ４ ~R ８ Is it deuterium; or R ４ However, it is an unsubstituted or deuterium-substituted phenyl, R １ ~R ３ and R ５ ~R ８ The compound according to claim 1, wherein the compound is deuterium.

7. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is one selected from the group consisting of the following. 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】

8. An organic light-emitting element comprising a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain a compound according to any one of claims 1 to 7.

9. The organic light-emitting element according to claim 8, wherein the organic layer is a light-emitting layer.

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