Novel compounds and organic light-emitting devices containing the same

Abstract

The present invention provides 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 based on Korean Patent Application No. 10-2024-0048065 dated April 9, 2024, and all content disclosed in the said Korean Patent Application 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 light emission phenomena refer to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices that utilize organic light emission phenomena have a wide viewing angle, excellent contrast, and fast response time, and are superior in brightness, driving voltage, and response speed characteristics, and are the subject of much 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 stability 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 into the organic layer at the positive electrode and electrons are injected into the organic layer at the negative electrode. When the injected holes and electrons combine, an exciton is formed, and when the exciton falls back to the ground state, it emits light.

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

[0006] [Patent Document 1] Korean Patent Publication No. 10-2000-0051826

Summary of the Invention

Problems to be Solved by the Invention

[0007] The present invention relates to a novel compound 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 1]

Chemical

Chemical

[0009] Furthermore, the present invention provides an organic light-emitting device 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 represented by the chemical formula 1. [Effects of the Invention]

[0010] The compound represented by chemical formula 1 described above can be used as a material for the organic layer of an organic light-emitting device, and can improve efficiency, low drive voltage, and / or lifespan characteristics in the organic light-emitting device. [Brief explanation of the drawing]

[0011] [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 hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a negative electrode 4. [Modes for carrying out the invention]

[0012] The present invention will be explained in more detail below for better understanding.

[0013] In this specification, [ka] This signifies a bond that is linked to other substituents, and "D" represents deuterium.

[0014] 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; cyano 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 heterocyclic groups containing one or more N, O, and S atoms, or substituted or unsubstituted with substituents in which two or more substituents from the above-mentioned substituents are linked. For example, a "substituent in which two or more substituents are linked" can be a biphenylyl group. That is, a biphenylyl group may also be an aryl group and can be interpreted as a substituent in which two phenyl groups are linked. For example, the term "substituted or unsubstituted" means "unsubstituted or deuterium, halogen, cyano, C 1-10 Alkyl, C 1-10 Alkoxy and C 6-20 The term "substituted with one or more substituents selected from the group consisting of aryl atoms" can be understood as "unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogens, cyano, methyl, ethyl, phenyl, and naphthyl atoms." In this specification, the term "substituted with one or more substituents" can be understood as "substituted with one or the maximum number of substituted hydrogen atoms." Alternatively, in this specification, the term "substituted with one or more substituents" can be understood as "substituted with one to five substituents," or "substituted with one or two substituents."

[0015] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but it is preferably between 1 and 40 carbon atoms. Specifically, substituents can have the following structures, but are not limited thereto. [Chem.]

[0016] In this specification, the ester group can be substituted by an oxygen of the ester group 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, it can be a substituent of the following structural formula, but is not limited thereto. [Chem.]

[0017] In this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, it can be a substituent having the following structure, but is not limited thereto. [Chem.]

[0018] In this specification, the substituted or unsubstituted silyl group means -Si(Z1)(Z2)(Z3), where Z1, Z2, and Z3 are each independently hydrogen, deuterium, substituted or unsubstituted C 1-60 alkyl, substituted or unsubstituted C 1-60 haloalkyl, substituted or unsubstituted C 2-60 alkenyl, substituted or unsubstituted C 2-60 haloalkenyl, or substituted or unsubstituted C 6-60 aryl. According to one embodiment, Z1, Z2, and Z3 are each independently hydrogen, deuterium, substituted or unsubstituted C 1-10 alkyl, substituted or unsubstituted C 1-10 haloalkyl, substituted or unsubstituted C 1-10 haloalkyl, or substituted or unsubstituted C 6-20It can be an aryl group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl groups.

[0019] In this specification, the boron group specifically refers to, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.

[0020] In this specification, examples of halogen groups include fluoro, chloro, bromo, or iodine.

[0021] 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. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to yet another embodiment, specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2 Examples include, but are not limited to, ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, and 2,2-dimethylheptyl.

[0022] 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 yet 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.

[0023] In this specification, the alicyclic group refers to a monovalent substituent derived from a saturated or unsaturated hydrocarbon ring compound that contains only carbon atoms as ring-forming atoms but lacks aromaticity, and is understood to encompass all monocyclic and condensed polycyclic compounds. In one embodiment, the alicyclic group has 3 to 60 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In yet another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. Examples of such alicyclic groups include monocyclic groups such as cycloalkyl groups, bridged hydrocarbon groups, spiro hydrocarbon groups, and substituents derived from hydrogenated derivatives of aromatic hydrocarbon compounds.

[0024] Specifically, examples of the aforementioned cycloalkyl groups 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] Furthermore, examples of the aforementioned crosslinking hydrocarbon groups include, but are not limited to, bicyclo[1.1.0]butyl, bicyclo[2.2.1]heptyl, bicyclo[4.2.0]octa-1,3,5-trienyl, adamantyl, and dekalinyl.

[0026] Examples of the aforementioned spirocyclic hydrocarbon group include, but are not limited to, spiro[3.4]octyl and spiro[5.5]undecanyl.

[0027] Furthermore, substituents derived from hydrogenated derivatives of aromatic hydrocarbon compounds refer to substituents derived from compounds in which hydrogen is added to some of the unsaturated bonds of monocyclic or polycyclic aromatic hydrocarbon compounds. Examples of such substituents include, but are not limited to, 1H-indenyl, 2H-indenyl, 4H-indenyl, 2,3-dihydro-1H-indenyl, 1,4-dihydronaphthalenyl, 1,2,3,4-tetrahydronaphthalenyl, 6,7,8,9-tetrahydro-5H-benzo[7]annulenyl, and 6,7-dihydro-5H-benzocycloheptenyl.

[0028] In this specification, an aryl group is understood to mean a substituent derived from a monocyclic or fused polycyclic compound that is aromatic while containing only carbon as a ring-forming atom, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60. In one embodiment, the number of carbon atoms of the aryl group is 6 to 30. In another embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group can be a monocyclic aryl group such as a phenyl group, a biphenylyl group, a terphenylyl group, etc., but is not limited thereto. The polycyclic aryl group can 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.

[0029] In this specification, the fluorenyl group can be substituted, and two substituents can bond to each other to form a spiro structure. When the fluorenyl group is substituted, [ka] It can become, for example, but is not limited to these.

[0030] In this specification, a heterocyclic group refers to a monovalent substituent derived from a monocyclic or fused polycyclic compound that further contains one or more heteroatoms selected from O, N, Si, and S as ring-forming atoms in addition to carbon, and is understood to encompass all substituents, both aromatic and non-aromatic. In one embodiment, the heterocyclic group has 2 to 60 carbon atoms. In another embodiment, the heterocyclic group has 2 to 30 carbon atoms. In yet another embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of such heterocyclic groups include heteroaryl groups and substituents derived from hydrogenated derivatives of heteroaromatic compounds.

[0031] Specifically, the heteroaryl group refers to a substituent derived from a monocyclic or fused polycyclic compound that further contains one or more heteroatoms selected from N, O, and S as ring-forming atoms in addition to carbon, and refers to an aromatic substituent. In one embodiment, the heteroaryl group has 2 to 60 carbon atoms. In yet another embodiment, the heteroaryl group has 2 to 30 carbon atoms. In yet another embodiment, the heteroaryl group has 2 to 20 carbon atoms. Examples of the heteroaryl groups mentioned above include, but are not limited to, thiophenyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridinyl, bipyridinyl, pyrimidinyl, triazinyl, acridinyl, pyridadinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyradinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, dibenzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, and phenothiazinyl.

[0032] Furthermore, substituents derived from hydrogenated derivatives of the heteroaromatic compounds refer to substituents derived from compounds in which hydrogen has been added to some of the unsaturated bonds of monocyclic or polycyclic heteroaromatic compounds. Examples of such substituents include, but are not limited to, 1,3-dihydroisobenzofuranyl, 2,3-dihydrobenzofuranyl, 1,3-dihydrobenzo[c]thiophenyl, and 2,3-dihydro[b]thiophenyl.

[0033] In this specification, the aryl group in aralkyl groups, aralkenyl groups, alkylaryl groups, arylamine groups, and arylsilyl groups is the same as the examples of aryl groups described above. In this specification, the alkyl group in aralkyl groups, alkylaryl groups, and alkylamine groups is the same as the examples of alkyl groups described above. In this specification, the heteroaryl in heteroarylamines can be described using the description of heteroaryls described above. In this specification, the alkenyl group in aralkenyl groups is the same as the examples of alkenyl groups described above. In this specification, the description of aryl groups described above can be described using the description of aryl groups described above, except that arylenes are divalent groups. In this specification, the heteroaryl in heteroarylenes can be described using the description of heteroaryls described above, except that heteroarylenes are divalent groups. In this specification, the hydrocarbon ring can be described using the description of aryl groups or cycloalkyl groups described above, except that a hydrocarbon ring is formed by the bonding of two substituents, not a monovalent group. In this specification, the heteroaryl in heterocycles can be described using the description of heteroaryls described above, except that a heterocycle is formed by the bonding of two substituents, not a monovalent group.

[0034] In this specification, “deuterated or deuterated” means that at least one of the substituted hydrogen atoms in the compound, divalent linking group, or monovalent substituent is substituted with deuterium.

[0035] Furthermore, the phrase "unsubstituted or deuterium-substituted" or "deuterium-substituted or unsubstituted" means "unsubstituted or one to the maximum number of substituteable hydrogen atoms are substituted with deuterium." For example, the term "unsubstituted or deuterium-substituted phenanthryl" can be understood as "unsubstituted or phenanthryl with one to nine deuterium atoms," considering that the maximum number of deuterium-substituted hydrogen atoms in a phenanthryl structure is nine.

[0036] Furthermore, the term "deuterated structure" encompasses all compounds, divalent linking groups, or monovalent substituents in which at least one hydrogen atom is substituted with deuterium. For example, the deuterated structure of phenyl can be understood as referring to all monovalent substituents in which at least one substitutable hydrogen atom within the phenyl group is substituted with deuterium, as shown below. [ka]

[0037] Furthermore, the "deuterium substitution rate" or "degree of deuteration" of a compound means the ratio, calculated as a percentage, of the number of substituted deuterium atoms to the total number of hydrogen atoms that can exist in the compound (the sum of the number of hydrogen atoms that can be substituted with deuterium and the number of substituted deuterium atoms). Therefore, a "deuterium substitution rate" or "degree of deuteration" of a compound being "K%" means that K% of the hydrogen atoms that can be substituted with deuterium in the compound have been substituted with deuterium.

[0038] At this time, the "deuterium substitution rate" or "degree of deuteration" is determined by MALDI-TOF MS (Matrix-Assisted Laser Desorption / Ionization Time-of-Flight Mass Spectrometer), nuclear magnetic resonance spectroscopy ( 1 The deuterium can be measured by commonly known methods such as 1H NMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry). More specifically, when using MALDI-TOF MS, the "deuterium substitution rate" or "degree of deuteration" can be determined by first finding the number of deuterium atoms substituted in the compound through MALDI-TOF MS analysis, and then calculating the ratio of the number of substituted deuterium atoms to the total number of hydrogen atoms that may exist in the compound as a percentage.

[0039] (compound)

[0040] The present invention provides a compound represented by the chemical formula 1.

[0041] Preferably, the chemical formula 1 is represented by one of the following chemical formulas 1-1 to 1-3. [Case 1-1] [ka] [Formation 1-2] [ka] [Case 1-3] [ka] In the above chemical formulas 1-1 to 1-3, HAr1 and HAr2 are defined as described above. c, f, and h are each independent integers between 0 and 5. e and g are independent integers between 0 and 4.

[0042] Preferably, Ra and Rb are each independently hydrogen, deuterium, or unsubstituted or substituted with one or more deuterium atoms. 2-60 It is Ariel.

[0043] More preferably, Ra and Rb are each independently hydrogen, deuterium, phenyl, or biphenylyl, wherein the phenyl and biphenylyl are either unsubstituted or substituted with one or more deuterium atoms.

[0044] Preferably, Ra and Rb are each independently hydrogen or deuterium; or one of Ra and Rb is unsubstituted or substituted with one or more deuterium atoms in a phenyl molecule, or unsubstituted or substituted with one or more deuterium atoms in a biphenylyl molecule, and the remainder is hydrogen or deuterium.

[0045] More preferably, Ra is hydrogen, deuterium, unsubstituted or deuterium-substituted phenyl, or unsubstituted or deuterium-substituted biphenylyl, and Rb is hydrogen, deuterium, unsubstituted or deuterium-substituted phenyl, or unsubstituted or deuterium-substituted biphenylyl.

[0046] Preferably, R2 to R9 are each independently hydrogen, deuterium, or unsubstituted or substituted with one or more deuterium atoms. 2-60 It is an aryl group, and at least one of R2-R9 is deuterium.

[0047] More preferably, R2 to R9 are each independently hydrogen, deuterium, phenyl, or biphenylyl, and at least one of R2 to R9 is deuterium; the phenyl and biphenylyl are either unsubstituted or substituted with one or more deuterium atoms.

[0048] Preferably, seven or more of R2 to R9 are deuterium atoms.

[0049] More preferably, seven of R2 to R9 are deuterium, and one of them is either unsubstituted or phenyl substituted with one or more deuterium atoms, or biphenylyl substituted with one or more deuterium atoms; or eight of R2 to R9 may be deuterium.

[0050] Preferably, HAr1 and HAr2 are each independently one substituent selected from the group consisting of the following: [ka] [ka] [ka] [ka]

[0051] Preferably, HAr1 and HAr2 are identical to each other.

[0052] Typical examples of compounds represented by the aforementioned chemical formula 1 are as follows: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0053] On the other hand, the compound represented by chemical formula 1 can be produced by a manufacturing method such as the reaction shown in reaction equation 1 below, as an example. [Reaction Equation 1] [ka]

[0054] In the above reaction formula 1, the definitions of the remaining substituents excluding Y are as defined in the above chemical formula 1, where Y is a halogen, and preferably Y is fluoro or chloro.

[0055] The reaction formula 1 described above is a Suzuki coupling reaction and an amine substitution reaction, which are preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for each reaction can be changed as known in the art. The production method can be further elaborated in the production examples described later.

[0056] (Organic light-emitting device) 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 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 comprises a compound represented by the chemical formula 1.

[0057] The organic layer of the organic light-emitting element of the present invention may consist of a tomographic structure, but it may also consist of 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 suppression layer, an emissive layer, an electron transport layer, an electron injection layer, and so on. However, the structure of the organic light-emitting element is not limited thereto and may include even fewer organic layers.

[0058] Furthermore, the organic layer may include a light-emitting layer, in which case the organic layer containing the compound represented by chemical formula 1 may be the light-emitting layer.

[0059] In one embodiment, the organic layer may include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron injection and transport layer, in which case the organic layer containing the compound may be a light-emitting layer.

[0060] Furthermore, the organic light-emitting element according to the present invention can 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 can be an organic light-emitting element with 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.

[0061] Figure 1 shows an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. In such a structure, the compound represented by chemical formula 1 can be included in the light-emitting layer.

[0062] Figure 2 shows an example of an organic light-emitting element comprising a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a negative electrode 4. In such a structure, the compound represented by chemical formula 1 can be included in the light-emitting layer.

[0063] The organic light-emitting element according to the present invention can be 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 can be formed from the same substance or other substances.

[0064] 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 a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation, then forming an organic layer on top of that, which includes a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and finally depositing a material that can be used as a negative electrode on top of that. In addition to such methods, 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 a substrate.

[0065] Furthermore, the compound represented by chemical formula 1 can be formed in an organic layer not only by vacuum deposition but also by solution coating during the manufacture of organic light-emitting devices. Here, solution coating means, but is not limited to, spin coating, dip coating, doctor bladeding, inkjet printing, screen printing, spray coating, roll coating, etc.

[0066] In addition to this method, organic light-emitting diodes can also be manufactured by sequentially depositing the negative electrode material, organic layer, and positive electrode material onto a substrate (WO2003 / 012890). However, the manufacturing method is not limited to this.

[0067] 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.

[0068] As the positive electrode material, a material with a large work function is preferred to facilitate hole implantation into the organic layer. Specific examples of the positive electrode material include, but are not limited to, metals or alloys thereof such as vanadium, chromium, copper, zinc, and gold; 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.

[0069] The negative electrode 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 negative electrode material include, but are not limited to, metals or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; and multilayer materials such as LiF / Al or LiO2 / Al.

[0070] The hole injection layer is a layer that injects holes from the electrode. The hole injection material is preferably a compound that has the ability to transport holes, has an excellent hole injection effect on the positive electrode, and 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.

[0071] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. Suitable hole transport materials are those with high mobility for holes, capable of receiving holes from the positive electrode or hole injection layer and transferring them to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

[0072] The electron-blocking layer is formed on the hole transport layer, preferably in contact with the light-emitting layer, and plays a role in improving the efficiency of the organic light-emitting device by adjusting the hole mobility, preventing excessive electron movement, and increasing the probability of hole-electron bonding. The electron-blocking layer includes an electron-blocking material, and examples of such electron-blocking materials include, but are not limited to, arylamine-based organic compounds.

[0073] The aforementioned light-emitting material is preferably a material that can emit light in the visible light region by receiving and combining holes and electrons from a hole transport layer and an electron transport layer, respectively, and is characterized by 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, benzthiazole, and benzimidazole compounds; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc.

[0074] 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 may include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc.

[0075] Examples of dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluorantene compounds, and metal complexes. Specifically, aromatic amine derivatives include 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 which are substituted or unsubstituted with substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamino groups (one or more). 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.

[0076] The hole-blocking layer is formed on the light-emitting layer, preferably in contact with the light-emitting layer, and plays a role in improving the efficiency of the organic light-emitting device by adjusting electron mobility, preventing excessive hole movement, and increasing the probability of hole-electron bonding. The hole-blocking layer contains a hole-blocking substance, and examples of such hole-blocking substances include, but are not limited to, compounds into which electron-withdrawing groups have been introduced, such as triazine-containing azine derivatives; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; and phosphine oxide derivatives.

[0077] The electron injection and transport layer is a layer that simultaneously performs the roles of an electron transport layer and an electron injection layer, injecting electrons from the electrode and transporting the received electrons to the light-emitting layer, and is formed on the light-emitting layer or the hole blocking layer. Suitable electron injection and transport materials are those with high electron mobility, which can reliably inject electrons from the negative electrode and transfer them to the light-emitting layer. Compounds represented by chemical formula 1 can be used as such electron injection and transport layer materials. Examples of additional electron injection and transport materials include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes; triazine derivatives, etc. Alternatively, they can be used together with, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, etc. and their derivatives, metal complex compounds, or nitrogen-containing five-membered ring derivatives, etc.

[0078] The electron injection and transport layers can also be formed as separate layers, such as an electron injection layer and an electron transport layer. In such cases, the electron transport layer is formed on the light-emitting layer or the hole-blocking layer, and the electron injection and transport materials described above can be used as the electron transport material contained in the electron transport layer. Alternatively, the electron injection layer can be formed on the electron transport layer, and the electron injection material contained in the electron injection layer can be LiF, NaCl, CsF, Li2O, BaO, 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.

[0079] 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-hydroxyquinolina)chlorogallium, bis(2-methyl-8-hydroxyquinolina)(o-crezolat)gallium, bis(2-methyl-8-hydroxyquinolina)(1-naphthorato)aluminum, and bis(2-methyl-8-hydroxyquinolina)(2-naphthorato)gallium.

[0080] In one embodiment, the electron injection and transport layer or electron transport layer of the organic light-emitting element may contain both the compound represented by chemical formula 1 and the metal complex compound. In this case, the electron injection and transport layer or electron transport layer may contain the compound represented by chemical formula 1 and the metal complex compound in a weight ratio of 10:90 to 90:10, 30:70 to 70:30, or 50:50.

[0081] The organic light-emitting element according to the present invention may be a bottom-emitting element, a top-emitting element, or a double-sided light-emitting element, and can be a bottom-emitting element in particular where a relatively high luminous efficiency is required.

[0082] Furthermore, the compounds according to the present invention can be included not only in organic light-emitting devices but also in organic solar cells or organic transistors.

[0083] The manufacture of the compound represented by the above chemical formula 1 and the organic light-emitting element containing it will be specifically described in the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of the present invention.

[0084] [Manufacturing example]

[0085] Manufacturing Example 1: Manufacturing of Compound GH1 [ka]

[0086] Preparation of compound GH1-a Under a nitrogen atmosphere, 2-([1,1'-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine (50 g, 165.5 mmol) and (2-fluorophenyl)boronic acid (50.9 g, 364.0 mmol) were added to 500 ml of tetrahydrofuran and stirred under reflux. Then, potassium carbonate (68.6 g, 496.4 mmol) dissolved in 69 ml of water was added and stirred thoroughly, after which tetrakistriphenyl-phosphinopalladium (5.7 g, 5 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and aqueous layer were separated, and the organic layer was distilled. This was then added again to 1395 ml of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to produce a white solid compound GH1-a (50.2 g, 72%). MS:[M+H] + =422.5

[0087] Production of compound GH1 Under a nitrogen atmosphere, GH1-a (30 g, 71.2 mmol) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (27.5 g, 156.6 mmol) were added to 450 ml of dimethylformamide and stirred and refluxed. Then, tripotassium phosphate (45.3 g, 213.5 mmol) was added and stirred thoroughly. After reacting for 6 hours, the mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was then added again to 1042 mL of chloroform and dissolved, 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 produce the yellow solid compound GH1 (28.1 g, 54%). MS:[M+H] + =733

[0088] Manufacturing Example 2: Manufacturing of Compound GH2 [ka]

[0089] Preparation of compound GH2-a Compound GH2-a was prepared in the same manner as the method for producing compound GH1-a, except that 2,4-dichloro-6-phenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine. MS:[M+H] + =345.5

[0090] Manufacturing of compound GH2 Compound GH2 was produced in the same manner as the method for producing compound GH1, except that compound GH2-a was used instead of compound GH1-a, and 4-(phenyl-d5)-9H-carbazole-1,2,3,4,5,6,7,8-d7 was used instead of 9H-carbazole-1,2,3,4,5,6,7,8-d8. MS:[M+H] + =817

[0091] Manufacturing Example 3: Manufacturing of Compound GH3 [ka]

[0092] Preparation of compound GH3-a Compound GH3-a was prepared in the same manner as the method for producing compound GH1-a, except that 2-([1,1'-biphenyl]-3-yl)-4,6-dichloro-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine. MS:[M+H] + =422.5

[0093] Production of compound GH3 Compound GH3 was produced in the same manner as the method for producing compound GH1, except that compound GH3-a was used instead of compound GH1-a, and 3-(phenyl-d5)-9H-carbazole-1,2,4,5,6,7,8-d7 was used instead of 9H-carbazole-1,2,4,5,6,7,8-d8. MS:[M+H] + =893.2

[0094] Manufacturing Example 4: Manufacturing of Compound GH4 [ka]

[0095] Preparation of compound GH4-a Compound GH4-a was produced in the same manner as the method for producing compound GH1-a, except that 2,4-dichloro-6-phenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)boronic acid, and 3-fluoro-[1,1'-biphenyl]-4-yl)boronic acid was used instead of (2-fluorophenyl)boronic acid. MS:[M+H] + =498.5

[0096] Manufacturing of compound GH4 Compound GH4 was produced in the same manner as the method for producing compound GH1, except that compound GH4-a was used instead of compound GH1-a, and 4-(phenyl-d5)-9H-carbazole-1,2,3,4,5,6,7,8-d7 was used instead of 9H-carbazole-1,2,3,4,5,6,7,8-d8. MS:[M+H] + =809

[0097] Manufacturing Example 5: Manufacturing of Compound GH5 [ka]

[0098] Preparation of compound GH5-a Compound GH5-a was prepared in the same manner as the method for producing compound GH1-a, except that 2,4-dichloro-6-(phenyl-d5)-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine, and (3-fluoro-[1,1'-biphenyl]-4-yl)boronic acid was used instead of (2-fluorophenyl)boronic acid. MS:[M+H] + = 503.6

[0099] Manufacturing of compound GH5 Compound GH5 was produced in the same manner as the method for producing compound GH1, except that compound GH5-a was used instead of compound GH1-a, and 2-(phenyl-d5)-9H-carbazole-1,3,4,5,6,7,8-d7 was used instead of 9H-carbazole-1,2,3,4,5,6,7,8-d8. MS:[M+H] + =974

[0100] Manufacturing Example 6: Manufacturing of Compound GH6 [ka]

[0101] Preparation of compound GH6-a Under a nitrogen atmosphere, 4-bromo-9H-carbazole-1,2,3,4,5,6,7,8-d7 (50 g, 197.5 mmol) and ([1,1'-biphenyl]-3-yl-d9)boronic acid (40.9 g, 197.5 mmol) were added to 500 ml of tetrahydrofuran and stirred under reflux. Then, potassium carbonate (81.9 g, 592.5 mmol) was dissolved in 82 ml of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (6.8 g, 5.9 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. This was dissolved again in 994 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to produce a beige solid compound GH6-a (39.8 g, 60%). MS:[M+H] + =336.5

[0102] Preparation of compound GH6-b Under a nitrogen atmosphere, GH2-a (30 g, 86.9 mmol) and GH6-a (29.1 g, 86.9 mmol) were added to 450 ml of dimethylformamide and stirred and refluxed. Then, tripotassium phosphate (55.3 g, 260.6 mmol) was added and stirred thoroughly. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was then added again to 1148 ml of chloroform and dissolved, and after washing twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to produce the yellow solid compound GH6-b (28.7 g, 50%). MS:[M+H] + =661.9

[0103] Production of compound GH6 Compound GH6 was produced in the same manner as the method for producing compound GH6-b, except that compound GH6-b was used instead of compound GH2-a, and 9H-carbazole-1,2,3,4,5,6,7,8-d8 was used instead of compound GH6-a. MS:[M+H] + =817

[0104] Manufacturing Example 7: Manufacturing of Compound GH7 [ka]

[0105] Preparation of compound GH7-a Under a nitrogen atmosphere, 2,4-dichloro-6-phenyl-1,3,5-triazine (50 g, 221.2 mmol) and (4-fluoro-[1,1':3',1''-terphenyl]-3-yl)boronic acid (64.6 g, 221.2 mmol) were added to 500 ml of tetrahydrofuran and stirred under reflux. Then, potassium carbonate (91.7 g, 663.5 mmol) was dissolved in 92 ml of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (7.7 g, 6.6 mmol) was added. After reacting for 2 hours and cooling to room temperature, the organic layer and aqueous layer were separated, and the organic layer was distilled. This was then dissolved again in 969 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the filtrate was filtered and distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to produce a white solid compound GH7-a (63.9 g, 66%). MS:[M+H] + =438.9

[0106] Preparation of compound GH7-b Compound GH7-b was produced in the same manner as the method for producing compound GH7-a, except that compound GH7-a was used instead of 2,4-dichloro-6-phenyl-1,3,5-triazine, and (2-fluorophenyl)boronic acid was used instead of 4-fluoro-[1,1':3',1''-terphenyl]-3-yl)boronic acid. MS:[M+H] + =498.5

[0107] Manufacturing of compound GH7 Compound GH7 was produced in the same manner as the method for producing compound GH1, except that compound GH7-b was used instead of compound GH1-a. MS:[M+H] + =809.1

[0108] Manufacturing Example 8: Manufacturing of Compound GH8 [ka]

[0109] Manufacturing of GH8-a Compound GH8-a was produced in the same manner as the method for producing compound GH1-a, except that 2,4-dichloro-6-phenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine, and (3-fluoro-[1,1'-biphenyl]-4-yl)boronic acid was used instead of (2-fluorophenyl)boronic acid. MS:[M+H] + =498.5

[0110] Manufacturing of compound GH8 Compound GH8 was produced in the same manner as the method for producing compound GH1, except that compound GH8-a was used instead of compound GH1-a, and 4-(phenyl-d5)-9H-carbazole-1,2,3,4,5,6,7,8-d7 was used instead of 9H-carbazole-1,2,3,4,5,6,7,8-d8. MS:[M+H] + =809.1

[0111] [Examples]

[0112] 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. products were used as the detergent, and Millipore Co. filters were used to filter the distilled water twice. 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, the substrate was ultrasonically cleaned with isopropyl alcohol, acetone, and methanol solvents, dried, and then transported to a plasma cleaning machine. Alternatively, the substrate was cleaned using oxygen plasma for 5 minutes before being transported to a vacuum deposition chamber.

[0113] A hole injection layer was formed on the prepared ITO transparent electrode by thermal vacuum deposition of the compound HI-A to a thickness of 60 nm. A first hole transport layer with a thickness of 5 nm was formed on the hole injection layer by vacuum deposition of the compound HAT, and a second hole transport layer with a thickness of 50 nm was formed on the first hole transport layer by vacuum deposition of the compound HT-A. An electron barrier layer was formed on the hole transport layer by thermal vacuum deposition of the compound HT-B to a thickness of 45 nm.

[0114] On the electron-blocking layer, the previously prepared compound GH1 was mixed with the compound GH-P 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 electron-emitting layer. On the electron-emitting layer, the compound ET-A was vacuum-deposited to a thickness of 5 nm to form a hole-blocking layer. On the electron-blocking layer, the compound ET-B and the compound LiQ were vacuum-deposited in a 1:1 weight ratio to form an electron-injection and transport layer with a thickness of 35 nm.

[0115] After depositing lithium fluoride (LiF) to a thickness of 1 nm onto the electron injection and transport layer, aluminum was then deposited to a thickness of 100 nm to form a negative electrode, thereby manufacturing an organic light-emitting element. [ka]

[0116] During the above process, 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*10⁻¹⁰. -7 torr~5*10 -5 Torr was maintained.

[0117] Examples 2-8 and Comparative Examples 1-5 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 GH1. In Table 1 below, the structures of compounds GH9 to GH13 are as follows. [ka]

[0118] Experimental example Current was applied to the organic light-emitting elements fabricated in Examples 1 to 8 and Comparative Examples 1 to 3, 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 measured by applying the current, and T95 had a current density of 10 mA / cm². 2 This refers to the time (hr) until the initial brightness decreases to 95%. [Table 1]

[0119] As shown in Table 1 above, it was confirmed that the organic light-emitting devices of the examples manufactured using the compound represented by chemical formula 1 of the present invention exhibited lower driving voltage and superior efficiency and lifespan compared to the organic light-emitting devices of the comparative examples. [Explanation of Symbols]

[0120] 1: Circuit board 2: Positive electrode 3: Emitting layer 4: Negative electrode 5: Hole injection layer 6: Hole transport layer 7: Electron barrier layer 8: Hole blocking layer 9: Electron injection and transport layer

Claims

1. The compound represented by the following chemical formula 1: [Chemical formula 1] 【Chemistry 1】 In the aforementioned chemical formula 1, Ar １ and Ar ２ Each is independently hydrogen, deuterium, or an unsubstituted or deuterium-substituted phenyl. However, Ar １ and Ar ２ Except when all of them are phenyl, R １ Each is independently hydrogen or deuterium. HAr １ and HAr ２ Each of these is an independent substituent represented by the following chemical formula 2: [Chemical 2] 【Chemistry 2】 In the aforementioned chemical formula 2, D is deuterium, Ra and Rb are, independently, hydrogen, deuterium, or substituted or unsubstituted C. ６－６０ It is Ariel, Rc is hydrogen or deuterium, R ２ ~R ９ each independently represents hydrogen, deuterium, or a substituted or unsubstituted C ６－６０ aryl, and at least one of R ２ ~R ９ is deuterium, a is an integer between 0 and 3. b is either 0 or 1.

2. The aforementioned chemical formula 1 is represented by one of the following chemical formulas 1-1 to 1-3. The compound according to claim 1: [Chemical formula 1-1] 【Transformation 3】 [Chemical formula 1-2] 【Chemistry 4】 [Chemical formula 1-3] 【Transformation 5】 In the above chemical formulas 1-1 to 1-3, HAr １ and HAr ２ This is as defined in claim 1, c, f, and h are each independent integers between 0 and 5. e and g are independent integers between 0 and 4.

3. Ra and Rb are independently hydrogen, deuterium, phenyl, or biphenylyl. The phenyl and biphenylyl compounds are either unsubstituted or substituted with one or more deuterium atoms. The compound according to claim 1.

4. Ra and Rb are independently hydrogen or deuterium, or Either Ra or Rb is an unsubstituted or deuterium-substituted phenyl, or an unsubstituted or deuterium-substituted biphenylyl, and the remainder is hydrogen or deuterium. The compound according to claim 1.

5. R ２ ~R ９ Each of these is independently hydrogen, deuterium, phenyl, or biphenylyl, and R ２ ~R ９ At least one of them is deuterium, The phenyl and biphenylyl compounds are either unsubstituted or substituted with one or more deuterium atoms. The compound according to claim 1.

6. R ２ ~R ９ Seven or more of them are deuterium. The compound according to claim 1.

7. HAr １ and HAr ２ Each of these is independently one substituent selected from the group consisting of the following: The compound according to claim 1. 【Transformation 6】 【Transformation 7】 【Transformation 8】

8. HAr １ and HAr ２ They are identical to each other. The compound according to claim 1.

9. The compound represented by the aforementioned chemical formula 1 is one selected from the group consisting of the following compounds: The compound according to claim 1. 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】

10. 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 9.

11. The organic light-emitting element according to claim 10, wherein the organic layer containing the compound is a light-emitting layer.

Images