Novel compound and organic light-emitting device using same

Abstract

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

Description

Technical Field

[0001] Cross-references to related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2022-0166942 filed on December 2, 2022 and Korean Patent Application No. 10-2023-0167842 filed on November 28, 2023, and incorporates all the contents disclosed in the documents of the Korean patent applications as part of this specification.

[0003] The present invention relates to novel compounds and organic light-emitting devices comprising the same. Background Art

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

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

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

[0007] Prior art literature

[0008] Patent Literature

[0009] (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826 Summary of the invention

[0010] Technical issues

[0011] The present invention relates to novel compounds and organic light-emitting devices comprising the same.

[0012] Solution to the problem

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

[0014] A compound represented by the following Chemical Formula 1.

[0015] [Chemical formula 1]

[0016]

[0017] In the above chemical formula 1,

[0018] L is a direct bond, or a substituted or unsubstituted C 6-20 The arylene group,

[0019] a is an integer from 0 to 2,

[0020] R1 is independently hydrogen, deuterium, or substituted or unsubstituted naphthyl, and in this case, as a substituent of naphthyl, cyano is excluded,

[0021] n is an integer from 1 to 8, and at least one of R1 is a substituted or unsubstituted naphthyl group,

[0022] R2 is hydrogen or deuterium,

[0023] m is an integer from 0 to 7,

[0024] A is the following chemical formula 2,

[0025] [Chemical formula 2]

[0026]

[0027] In the above chemical formula 2,

[0028] X is N or CR, and at least 2 of X are N,

[0029] R is independently hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 Aryl,

[0030] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroaryl.

[0031] In addition, the present invention provides an organic light-emitting device, comprising: a first electrode, a second electrode arranged opposite to the first electrode, and one or more organic layers arranged between the first electrode and the second electrode, wherein one or more of the organic layers contains a compound represented by the above chemical formula 1.

[0032] Effects of the Invention

[0033] The compound represented by the above chemical formula 1 can be used as a material for an organic layer of an organic light-emitting device, in which improved efficiency, lower driving voltage and / or improved life characteristics can be achieved. In particular, the compound represented by the above chemical formula 1 can be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 The figure shows an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a light-emitting layer 3 , and a cathode 4 .

[0035] Figure 2 The diagram shows an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a hole injection layer 5 , a hole transport layer 6 , a light-emitting layer 7 , an electron transport layer 8 , and a cathode 4 . DETAILED DESCRIPTION

[0036] In the following, the present invention will be described in more detail to help understanding the present invention.

[0037] In this manual, "D" represents a bond to other substituents, and "D" represents deuterium.

[0038] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group Arylthio Alkylsulfonyl Arylsulfonyl Silyl; boryl; alkyl; cycloalkyl; alkenyl; aryl; aralkyl; aralkenyl; alkylaryl; alkylamino; aralkylamino; heteroarylamino; arylamino; arylphosphino; or substituted or unsubstituted with one or more substituents in a heterocyclic group containing one or more N, O and S atoms, or substituted or unsubstituted with a substituent formed by connecting two or more substituents among the substituents exemplified above. For example, "a substituent formed by connecting two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may also be interpreted as a substituent formed by connecting two phenyl groups.

[0039] In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably the number of carbon atoms is 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.

[0040]

[0041] In the present specification, in the ester group, the oxygen of the ester group may be substituted by a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be of the following structural formula, but is not limited thereto.

[0042]

[0043] In the present specification, the number of carbon atoms in the imide group is not particularly limited, but preferably the number of carbon atoms is 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.

[0044]

[0045] In the present specification, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited thereto.

[0046] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0047] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl, but are not limited thereto.

[0048] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0049] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0050] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, yl, fluorenyl, etc., but are not limited to these.

[0051] In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. etc. However, the present invention is not limited thereto.

[0052] In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as hetero elements, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl and dibenzofuranyl, but are not limited thereto.

[0053] In the present specification, the aryl group in aralkyl, aralkenyl, alkylaryl, and arylamine is the same as the examples of the aryl group described above. In the present specification, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the examples of the alkyl group described above. In the present specification, the heteroaryl group in heteroarylamine can be applied to the above-mentioned description of the heterocyclic group. In the present specification, the alkenyl group in aralkenyl is the same as the examples of the alkenyl group described above. In the present specification, the arylene group is a divalent group, and the above-mentioned description of the aryl group can be applied. In the present specification, the heteroarylene group is a divalent group, and the above-mentioned description of the heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a monovalent group, but two substituents are combined, and the above-mentioned description of the aryl group or cycloalkyl group can be applied. In the present specification, the heterocycle is not a monovalent group, but two substituents are combined, and the above-mentioned description of the heterocyclic group can be applied.

[0054] (Compound)

[0055] The present invention provides a compound represented by the above Chemical Formula 1.

[0056] L is a direct bond, or a substituted or unsubstituted C 6-20 Preferably, L may be a direct bond, a phenylene group, a biphenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group or a terphenylene group. When L is a phenylene group, a biphenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group or a terphenylene group, the above L may be unsubstituted or substituted with one or more deuterium groups.

[0057] a is an integer from 0 to 2.

[0058] R1 is independently hydrogen, deuterium, or substituted or unsubstituted naphthyl, and in this case, cyano is excluded as a substituent of naphthyl. n is an integer of 1 to 8, and at least one of R1 is substituted or unsubstituted naphthyl.

[0059] Specifically, 1 to 3 of R1 are substituted or unsubstituted naphthyl, and the rest are hydrogen or deuterium.

[0060] In addition, the naphthyl group of R1 may be unsubstituted; or may be substituted with one or more deuterium, halogen, C 1-10 Alkyl, C substituted with one or more deuterium or unsubstituted 6-12 The residue is substituted with an aryl group or a six-membered heteroaryl group containing 1 to 3 nitrogen atoms.

[0061] Specifically, the naphthyl group of R1 may be unsubstituted or substituted with one or more deuterium, fluoro, tert-butyl or pyridyl groups.

[0062] R2 is hydrogen or deuterium, and m is an integer from 0 to 7.

[0063] Specifically, R2 may be hydrogen,

[0064] Three of R2 are hydrogen and the remaining four are deuterium.

[0065] Two of R2 are hydrogen and the remaining five are deuterium.

[0066] One of R2 is hydrogen and the other six are deuterium, or

[0067] R2 is deuterium.

[0068] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Preferably, Ar1 and Ar2 are each independently phenyl, biphenyl, naphthyl, phenanthryl, (phenyl) naphthyl, (naphthyl) phenyl, phenylbenzothiazolyl, phenylbenzothiazolyl, Azolyl, benzothiazolyl, benzo oxazolyl, phenylbenzimidazolyl, ethylbenzimidazolyl, methylbenzimidazolyl, benzofuranyl, phenylbenzofuranyl, benzothiophenyl, phenylbenzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, 9-phenylcarbazolyl, anthracenyl, pyrene, fluorenyl or triphenylene.

[0069] More preferably, the phenylbenzothiazolyl group may be a 2-phenylbenzothiazolyl group, a phenylbenzo The oxazolyl group may be 2-phenylbenzo Azolyl, benzothiazolyl can be benzothiazol-2-yl, benzo The azole group can be benzo The oxazol-2-yl group, the phenylbenzimidazolyl group can be N-phenylbenzimidazol-2-yl or 2-phenylbenzimidazol-1-yl group, the ethylbenzimidazolyl group can be N-ethylbenzimidazol-2-yl or 2-ethylbenzimidazol-1-yl group, and the methylbenzimidazolyl group can be N-methylbenzimidazol-2-yl group.

[0070] The above Ar1 and Ar2 may each independently be unsubstituted or substituted with one or more deuterium.

[0071] R can be independently hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 Specifically, R can be hydrogen or deuterium.

[0072] The compound represented by the above Chemical Formula 1 is a compound represented by one of the group consisting of:

[0073]

[0074] The explanations for Ar1, Ar2, L, a, R1, R2, X, n and m are the same as those defined in Chemical Formula 1.

[0075] X is N or CR, and at least two of X are N.

[0076] Specifically,

[0077] The compound represented by Chemical Formula 2 may be represented by one of the group consisting of the following.

[0078]

[0079] The explanations for Ar1, Ar2 and R are the same as those defined in Chemical Formula 2.

[0080] The compound represented by the above Chemical Formula 1 is any one selected from the group consisting of:

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100] In addition, the above-mentioned compound may contain no deuterium or may contain one or more deuterium.

[0101] When the above-mentioned compound contains deuterium, the deuterium substitution rate of the compound can be 1% to 100%. Specifically, the deuterium substitution rate of the above-mentioned compound can be 5% or more, 10% or more, 20% or more, 25% or more, 30% or more, 40% or more, or 50% or more and 100% or less, 90% or less, 80% or less, or 70% or less. The deuterium substitution rate of such a compound is calculated as the ratio of the number of deuteriums substituted in the chemical formula to the total number of hydrogens that can exist. In this case, the number of deuteriums substituted can be obtained by MALDI-TOF MS (Matrix-Assisted Laser Desorption / Ionization Time-of-Flight Mass Spectrometer) analysis.

[0102] As an example, the compound may contain no deuterium or may contain 1 to 60 deuteriums. Specifically, when the compound contains deuterium, the compound may contain 1 or more, 3 or more, 5 or more, 7 or more, 10 or more, 12 or more, 15 or more, 18 or more, 20 or more, 22 or more, 25 or more, 28 or more, or 30 or more and 60 or less, 56 or less, 50 or less, 45 or less, 40 or less, or 35 or less deuteriums.

[0103] In addition, the present invention provides a method for producing the compound represented by the above Chemical Formula 1 as shown in the following Reaction Formula 1.

[0104] [Reaction 1]

[0105]

[0106] The explanations for Ar1, Ar2, L, a, R1, R2, X, n and m are the same as those defined in Chemical Formula 1. Y, Z and Z' are halogen, preferably bromine or chlorine.

[0107] Steps 2 and 3 of reaction formula 1 are Suzuki coupling reactions, preferably carried out in the presence of a palladium catalyst, and the reactive groups used for the Suzuki coupling reaction can be changed according to techniques known in the art. The above-mentioned production method can be further embodied in the production examples and synthesis examples described later.

[0108] In addition, the present invention provides an organic light-emitting device including the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light-emitting device, which includes: a first electrode, a second electrode disposed opposite to the above first electrode, and one or more organic layers disposed between the above first electrode and the above second electrode, wherein one or more of the organic layers includes the compound represented by the above chemical formula 1.

[0109] The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0110] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by the above Chemical Formula 1. In particular, the compound according to the present invention may be used as a host of the light-emitting layer. In particular, the compound according to the present invention may be used as a red host of the light-emitting layer.

[0111] In addition, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by Chemical Formula 1.

[0112] In addition, the electron transport layer, the electron injection layer, or the layer that simultaneously transports and injects electrons contains the compound represented by Chemical Formula 1.

[0113] In addition, the organic layer includes a light emitting layer and an electron transport layer, and the electron transport layer may include the compound represented by Chemical Formula 1.

[0114] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having an inverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to one embodiment of the present invention is shown in FIG. Figure 1 and 2 .

[0115] Figure 1 The figure shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In the above structure, the compound represented by the above chemical formula 1 may be contained in the above light emitting layer.

[0116] Figure 2 The diagram shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4. In the structure described above, the compound represented by the above chemical formula 1 may be contained in one or more of the above hole injection layer, hole transport layer, light-emitting layer, and electron transport layer.

[0117] The organic light-emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers contains the compound represented by the above Chemical Formula 1. In addition, when the organic light-emitting device includes a plurality of organic layers, the organic layers can be formed of the same substance or different substances.

[0118] For example, the organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, it can be manufactured as follows: a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation is used to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode substance, an organic layer, and an anode substance on a substrate.

[0119] In addition, the compound represented by the above chemical formula 1 can be used not only by vacuum evaporation method but also by solution coating method to form an organic layer when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating method, dip coating method, blade coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited to these.

[0120] In addition to these methods, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003 / 012890). However, the manufacturing method is not limited to this.

[0121] As an example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

[0122] As the above-mentioned anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of the above-mentioned anode material include metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0123] In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0124] The hole injection layer is a layer for injecting holes from the electrode. As a hole injection material, it is preferably a compound having the ability to transport holes, the effect of injecting holes from the anode, an excellent hole injection effect for the light-emitting layer or the light-emitting material, and a compound having excellent thin film forming ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyaniline and polythiophene conductive polymers, but are not limited thereto.

[0125] The hole transport layer is a layer that receives holes from the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. Materials with high hole mobility are suitable. Specific examples include arylamine organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited thereto.

[0126] The luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo Compounds of the oxazole, benzothiazole and benzimidazole series; poly(p-phenylene vinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0127] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material includes an aromatic fused ring derivative or a heterocyclic compound. Specifically, as an aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0128] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamino groups, and there are pyrene, anthracene, The styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as a metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0129] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer. Materials with large electron mobility are suitable. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are common materials with low work function and accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.

[0130] The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound that has the ability to transport electrons, has the effect of injecting electrons from the cathode, has an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from migrating to the hole injection layer, and has excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0131] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

[0132] The organic light-emitting device according to the present invention may be a bottom emission device, a top emission device, or a bidirectional light-emitting device, and in particular, may be a bottom emission device requiring relatively high light-emitting efficiency.

[0133] In addition, the compound represented by the above Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

[0134] The preparation of the compound represented by the above Chemical Formula 1 and the organic light-emitting device including the same is specifically described in the following examples. However, the following examples are used to illustrate the present invention, and the scope of the present invention is not limited thereto.

[0135] [Synthesis example]

[0136] Synthesis Example 1: Synthesis of Compound 1

[0137]

[0138] Step 1) Synthesis of compound 1-a

[0139] Under nitrogen atmosphere, 4'-bromo-2-chlorospiro[fluorene-9,9'-xanthene] (50 g, 112.2 mmol) and bis(pinacolato)diboron (28.5 g, 112.2 mmol) were added to 1000 ml of distilled water. alkane (Diox), stirring and reflux. Then, potassium acetate (71.4 g, 336.5 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (0.6 g, 1.1 mmol) and dicyclohexylphosphine (0.4 g, 2.2 mmol) were added. After reacting for 4 hours, the organic layer was cooled to room temperature, filtered, and after removing the salt, the filtered organic layer was distilled. It was put into 10 times 553 mL of chloroform again to dissolve, washed with water twice, separated the organic layer, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a white solid compound 1-a (44.2 g, yield 80%, MS: [M+H] + =493.8).

[0140] Step 2) Synthesis of compound 1-b

[0141] Under nitrogen atmosphere, compound 1-a (50g, 101.5mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (27.2g, 101.5mmol) were added to 1000ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (32.3g, 304.4mmol) was dissolved in 32ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (3.5g, 3mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was again added to 20 times 1304mL of toluene to dissolve, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 1-b (42.4g, yield 65%, MS: [M+H] + =643.6).

[0142] Step 3) Synthesis of Compound 1

[0143] Under nitrogen atmosphere, compound 1-b (50g, 77.8mmol) and naphthalene-1-ylboric acid (13.4g, 77.8mmol) were added to 1000ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (24.7g, 233.4mmol) was dissolved in 25ml of water and put into the mixture. After sufficient stirring, tetrakis(triphenylphosphine)palladium (2.7g, 2.3mmol) was put into the mixture. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was put into 20 times 1073mL of toluene again and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 1 (40.2g, yield 75%, MS: [M+H]+ =690.3).

[0144] Synthesis Example 2: Synthesis of Compound 2

[0145]

[0146] In Synthesis Example 1, 4'-bromo-2-chlorospiro[fluorene-9,9'-xanthene], 2-chloro-4,6-diphenyl-1,3,5-triazine and naphthalene-1-ylboronic acid were replaced with 3'-bromo-4-chlorospiro[fluorene-9,9'-xanthene], 4-chloro-2,6-diphenylpyrimidine and naphthalene-2-ylboronic acid. Compound 2 (MS: [M+H]) was prepared by the same production method as the production method of compound 1. + =689.3).

[0147] Synthesis Example 3: Synthesis of Compound 3

[0148]

[0149] In Synthesis Example 1, 4'-bromo-2-chlorospiro[fluorene-9,9'-xanthene] and 2-chloro-4,6-diphenyl-1,3,5-triazine were replaced with 2'-bromo-4-chlorospiro[fluorene-9,9'-xanthene] and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-(naphthalene-1-yl)-1,3,5-triazine. Compound 3 (MS: [M+H]) was prepared by the same preparation method as that of Compound 1. + =830.3).

[0150] Synthesis Example 4: Synthesis of Compound 4

[0151]

[0152] In Synthesis Example 1, 4'-bromo-2-chlorospiro[fluorene-9,9'-xanthene], 2-chloro-4,6-diphenyl-1,3,5-triazine and naphthalene-1-ylboronic acid were replaced with 4'-bromo-4-chlorospiro[fluorene-9,9'-xanthene], 2-chloro-4-(dibenzo[b,d]thiophen-1-yl)-6-phenyl-1,3,5-triazine and (4-(tert-butyl)naphthalene-1-yl)boronic acid. Compound 4 (MS: [M+H]) was prepared by the same production method as the production method of Compound 1. + =852.3).

[0153] Synthesis Example 5: Synthesis of Compound 5

[0154]

[0155] In Synthesis Example 1, 4'-bromo-2-chlorospiro[fluorene-9,9'-xanthene] and 2-chloro-4,6-diphenyl-1,3,5-triazine were replaced with 4'-bromo-2,7-dichlorospiro[fluorene-9,9'-xanthene]-2',3,3',4,5,5',6,6',7'-d9 and 2-chloro-4,6-diphenylpyrimidine. Compound 5 (MS: [M+H]) was prepared by the same preparation method as that of Compound 1. + =824.4).

[0156] Synthesis Example 6: Synthesis of Compound 6

[0157]

[0158] In Synthesis Example 1, 4'-bromo-2-chlorospiro[fluorene-9,9'-xanthene], 2-chloro-4,6-diphenyl-1,3,5-triazine and naphthalene-1-ylboronic acid were replaced with 2'-bromo-4-chlorospiro[fluorene-9,9'-xanthene], 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine and naphthalene-2-ylboronic acid. Compound 6 (MS: [M+H]) was prepared by the same preparation method as the preparation method of Compound 1. + =766.3).

[0159] Synthesis Example 7: Synthesis of Compound 7

[0160]

[0161] In Synthesis Example 1, 4'-bromo-2-chlorospiro[fluorene-9,9'-xanthene], 2-chloro-4,6-diphenyl-1,3,5-triazine and naphthalene-1-ylboronic acid were replaced with 3'-bromo-2-chlorospiro[fluorene-9,9'-xanthene], 2,2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine and naphthalene-2-ylboronic acid. Compound 7 (MS: [M+H]) was prepared by the same production method as the production method of Compound 1. + =842.3).

[0162] Synthesis Example 8: Synthesis of Compound 8

[0163]

[0164] In Synthesis Example 1, 4'-bromo-2-chlorospiro[fluorene-9,9'-xanthene], 2-chloro-4,6-diphenyl-1,3,5-triazine and naphthalene-1-ylboronic acid were replaced with 4'-bromo-4-chlorospiro[fluorene-9,9'-xanthene], 4-(1-bromonaphthalene-2-yl)-2,6-diphenylpyrimidine and naphthalene-2-ylboronic acid. Compound 8 (MS: [M+H]) was prepared by the same preparation method as the preparation method of Compound 1. + =815.3).

[0165] Synthesis Example 9: Synthesis of Compound 9

[0166]

[0167] In Synthesis Example 1, 4'-bromo-2-chlorospiro[fluorene-9,9'-xanthene], 2-chloro-4,6-diphenyl-1,3,5-triazine and naphthalene-1-ylboronic acid were replaced with 2'-bromo-3-chlorospiro[fluorene-9,9'-xanthene], 2-(4-(3-bromonaphthalene-1-yl)phenyl)-4,6-diphenylpyrimidine and naphthalene-2-ylboronic acid. Compound 9 (MS: [M+H]) was prepared by the same production method as the production method of Compound 1. + =891.3).

[0168] Synthesis Example 10: Synthesis of Compound 10

[0169]

[0170] In Synthesis Example 1, 4'-bromo-2-chlorospiro[fluorene-9,9'-xanthene], 2-chloro-4,6-diphenyl-1,3,5-triazine and naphthalene-1-ylboronic acid were replaced with 3'-bromo-4-chlorospiro[fluorene-9,9'-xanthene], 3-(4-(3'-bromo-[1,1'-biphenyl]-3-yl)-6-phenylpyrimidin-2-yl)-9-phenyl-9H-carbazole and (4-phenylnaphthalene-1-yl)boronic acid. Compound 10 (MS: [M+H]) was prepared by the same production method as the production method of Compound 1. + =1082.4).

[0171] Experimental Example 1

[0172] ITO (indium tin oxide) is used The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0173] On the ITO transparent electrode prepared in this way, the following compound HI-A was applied as The hole injection layer was formed by thermal vacuum deposition of a thickness of 1000 mm / s. On the hole injection layer, hexanitrile hexaazatriphenylene (hexaazatriphenylene; HAT, ) and the following compound HT-A The hole transport layer is formed by vacuum deposition.

[0174] Next, on the hole transport layer, a film with a thickness of The following compounds BH and BD were vacuum deposited at a weight ratio of 25:1 to form a light-emitting layer.

[0175] On the above-mentioned light-emitting layer, the compound 1 prepared in Synthesis Example 1 and the following compound [LiQ] (lithium quinolate) were vacuum-deposited at a weight ratio of 1:1, thereby On the electron transport and injection layer, lithium fluoride (LiF) is sequentially The thickness of the aluminum A cathode is formed by evaporation with a thickness of .

[0176]

[0177] In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at the cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 1×10 -7 ~5×10 -8 A support is provided to produce an organic light-emitting device.

[0178] Experimental Examples 2 to 10

[0179] An organic light-emitting device was manufactured by the same method as in Experimental Example 1, except that the compound shown in Table 1 below was used instead of Compound 1 in Synthesis Example 1.

[0180] Comparative Experimental Examples 1 to 8

[0181] An organic light-emitting device was manufactured by the same method as in Experimental Example 1, except that the compound in Table 1 below was used instead of Compound 1 in Synthesis Example 1. Compounds ET-1 to ET-8 used in Table 1 below are as follows.

[0182]

[0183] For the organic light-emitting devices manufactured in the above experimental examples and comparative experimental examples, the 2 The driving voltage, luminous efficiency and color coordinates were measured at a current density of 20 mA / cm 2 The time (T 90 ). The results are shown in the following Table 1.

[0184] [Table 1]

[0185]

[0186] As shown in Table 1, it was confirmed that the organic light-emitting device using the compound represented by Chemical Formula 1 of the present invention had good voltage, efficiency and / or lifetime (T 90 ) showed excellent characteristics.

[0187] Comparing Experimental Examples 1 to 10 of Table 1 with Comparative Experimental Examples 1 to 5, the organic light-emitting device including the compound of Chemical Formula 1 of the present invention is substituted with an N-containing ring having electron transport properties on the xanthene side and a naphthyl group on the fluorene side, thereby variously adjusting the electron transport capability. Therefore, it can be confirmed that compared with the organic light-emitting device substituted with a substituent on the fluorene side or substituted at the opposite position thereof, it shows significantly excellent characteristics in terms of efficiency and lifespan.

[0188] Comparing Experimental Examples 1 to 10 in Table 1 with Comparative Experimental Example 6, the organic light-emitting device including the compound of Chemical Formula 1 of the present invention is advantageous in variously adjusting the electron transport capability because both Ar1 and Ar2 on the N-containing ring having electron transport characteristics are substituted with aryl groups. Therefore, it can be confirmed that compared with the organic light-emitting device substituted with alkyl groups on the N-containing ring, it shows significantly superior characteristics in terms of efficiency and lifespan.

[0189] By comparing Experimental Examples 1 to 10 in Table 1 with Comparative Experimental Example 7, the organic light-emitting device including the compound of Chemical Formula 1 of the present invention can variously adjust the electron transport capability due to the introduction of the naphthyl group in R1. Therefore, it can be confirmed that compared with the organic light-emitting device not substituted with the naphthyl group, it shows significantly superior characteristics in terms of efficiency and lifespan.

[0190] By comparing Experimental Examples 1 to 10 of Table 1 with Comparative Experimental Example 8, it can be confirmed that L of the organic light-emitting device including the compound of Chemical Formula 1 of the present invention is a substituted and unsubstituted aryl group, which is advantageous in terms of thermal stability. Therefore, it can be confirmed that compared with an organic light-emitting device in which L is substituted by a heteroaryl group and an alkyl group having inferior characteristics in terms of thermal stability, significantly superior characteristics are shown in terms of efficiency and life characteristics.

[0191] [Explanation of symbols]

[0192] 1: Substrate 2: Anode

[0193] 3: Light-emitting layer 4: Cathode

[0194] 5: Hole injection layer 6: Hole transport layer

[0195] 7: Light-emitting layer 8: Electron transport layer.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, L is a direct bond, or a substituted or unsubstituted C 6-20 The arylene group, a is an integer from 0 to 2, R 1 are each independently hydrogen, deuterium, or a substituted or unsubstituted naphthyl group, and in this case, as a substituent of the naphthyl group, cyano group is excluded, n is an integer from 1 to 8, and R 1 At least one of is a substituted or unsubstituted naphthyl group, R 2 is hydrogen or deuterium, m is an integer from 0 to 7, A is the following chemical formula 2, [Chemical formula 2] In the chemical formula 2, X is N or CR, and at least 2 of X are N, R is independently hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 Aryl, Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroaryl.

2. The compound according to claim 1, in, The compound represented by the chemical formula 1 is represented by one of the group consisting of: For Ar 1 ,Ar 2 , L, a, R 1 , R 2 The descriptions of , X, n and m are the same as those defined in claim 1.

3. The compound according to claim 1, in, The compound represented by the chemical formula 2 is represented by one of the group consisting of: For Ar 1 ,Ar 2 The descriptions of R are the same as those defined in claim 1.

4. The compound according to claim 1, in, L is a direct bond, a phenylene group, a biphenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group or a terphenylene group, When L is phenylene, biphenylene, naphthylene, anthrylene, phenanthrylene or terphenylene, these are unsubstituted or substituted with one or more deuterium groups.

5. The compound according to claim 1, in, Ar 1 and Ar 2 Each of the following is independently phenyl, biphenyl, naphthyl, phenanthryl, (phenyl)naphthyl, (naphthyl)phenyl, phenylbenzothiazolyl, phenylbenzo Azolyl, benzothiazolyl, benzo oxazolyl, phenylbenzimidazolyl, ethylbenzimidazolyl, methylbenzimidazolyl, benzofuranyl, phenylbenzofuranyl, benzothiophenyl, phenylbenzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, 9-phenylcarbazolyl, anthracenyl, pyrene, fluorenyl or triphenylene, The Ar 1 and Ar 2 Each is independently unsubstituted or substituted with one or more deuterium.

6. The compound according to claim 1, in, R is hydrogen or deuterium.

7. The compound according to claim 1, in, R 1 1 to 3 of them are substituted or unsubstituted naphthyl, and the rest are hydrogen or deuterium.

8. The compound according to claim 1, in, R 1 The naphthyl group is unsubstituted; or is replaced by one or more deuterium, halogen, C 1-10 Alkyl, C substituted with one or more deuterium or unsubstituted 6-12 aryl, or a six-membered heteroaryl containing 1 to 3 N atoms.

9. The compound according to claim 1, in, R is hydrogen or deuterium.

10. The compound according to claim 1, in, The compound represented by the chemical formula 1 is any one selected from the group consisting of:

11. An organic light emitting device, include: A first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 10.

12. The organic light emitting device according to claim 11, in, The organic layer containing the compound is a light-emitting layer or an electron transporting layer.

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