Novel compound and organic light-emitting device comprising same

Abstract

The present invention provides a novel compound and an organic light emitting device comprising the same.

Description

Technical Field

[0001] Cross-references to related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2022-0158662 filed on November 23, 2022, and incorporates all the contents disclosed in the document of the Korean Patent Application as a 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 continues to be 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] [Chemical formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] X1 is N or CR, and two or more of X1 are N,

[0018] X2 is N or CR, and two or more of X2 are N,

[0019] R is each independently hydrogen; deuterium; substituted or unsubstituted C 1-60 Alkyl; 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, or combined with any of the adjacent substituents Ar1 to Ar4 to form a substituted or unsubstituted benzene ring,

[0020] Ar1 to Ar4 not bonded to R are each independently substituted or unsubstituted C 6-60 Aryl, but at least one of Ar1 to Ar4 is C substituted by cyano 10-30 Aryl, wherein the above C substituted by cyano 10-30 The aryl group may be substituted with deuterium or not,

[0021] a is an integer from 0 to 4,

[0022] b is an integer from 0 to 4.

[0023] In addition, the present invention provides an organic light-emitting device, which includes: 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.

[0024] Effects of the Invention

[0025] 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

[0026] 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 .

[0027] Figure 2An 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 3 , an electron injection and transport layer 7 , and a cathode 4 is shown. DETAILED DESCRIPTION

[0028] In the following, the present invention will be described in more detail to help understanding the present invention.

[0029] In this manual, It represents the bond to other substituents.

[0030] 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.

[0031] 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 substituent may be a substituent of the following structure, but the substituent is not limited thereto.

[0032]

[0033] In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the substituents may be of the following structural formulas, but are not limited thereto.

[0034]

[0035] In the present specification, the number of carbon atoms in the imide group is not particularly limited, but the number of carbon atoms is preferably 1 to 25. Specifically, the substituent may be a substituent of the following structure, but the substituent is not limited thereto.

[0036]

[0037] 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.

[0038] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0039] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0040] 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, 4-methylhexyl, and 5-methylhexyl.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] The term "aromatic ring" used in this specification is understood to include not only a monocyclic or fused polycyclic ring containing only carbon as a ring-forming atom and having aromaticity in the whole molecule, but also a fused polycyclic ring formed by connecting adjacent substituents of a plurality of fused monocyclic rings such as a fluorene ring. At this time, the number of carbon atoms in the above-mentioned aromatic ring is 6 to 60, or 6 to 30, or 6 to 20, but is not limited thereto. In addition, as the above-mentioned aromatic ring, a benzene ring, a biphenyl ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a fluorene ring, etc., but is not limited thereto.

[0047] 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.

[0048] (Compound)

[0049] The present invention provides a compound represented by the above Chemical Formula 1.

[0050] Preferably, each R is independently hydrogen, deuterium, methyl, or a phenyl group which is substituted or unsubstituted with deuterium, or is combined with any of the adjacent substituents Ar1 to Ar4 to form a benzene ring which is unsubstituted or substituted with one or more deuteriums.

[0051] Preferably, none of Ar1 to Ar4 is bonded to R; or one of Ar1 and Ar2 is bonded to R; or one of Ar3 and Ar4 is bonded to R; or one of Ar1 and Ar2 and one of Ar3 and Ar4 are each bonded to R.

[0052] Preferably, one or two of Ar1 to Ar4 are C substituted by cyano. 10-30 Aryl.

[0053] Preferably, one of Ar1 to Ar4 is a C substituted by a cyano group. 10-30 Aryl; or one of Ar1 and Ar2 and one of Ar3 and Ar4 are each independently C substituted by cyano10-30 Aryl.

[0054] Preferably, the C substituted by cyano 10-30 Aryl is C substituted with a cyano group 10-30 Aryl.

[0055] Preferably, the C substituted by cyano 10-30 The aryl group is a biphenyl group substituted by a cyano group, a naphthyl group substituted by a cyano group, a terphenyl group substituted by a cyano group, a phenylnaphthyl group substituted by a cyano group, or a naphthylphenyl group substituted by a cyano group.

[0056] Preferably, it is not the above C substituted by cyano 10-30 Ar1 to Ar4 of the aryl group are each independently a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted naphthyl group, a deuterium-substituted or unsubstituted terphenyl group, or a deuterium-substituted or unsubstituted dimethylfluorenyl group, or combine with R to form a deuterium-substituted or unsubstituted benzene ring.

[0057] Preferably, Ar1 and Ar4 are each independently any one selected from the following groups; or one of Ar1 and Ar4 is any one selected from the following groups, and the other is phenyl, phenyl substituted with 1 to 5 deuteriums, biphenyl, naphthyl, terphenyl or dimethylfluorenyl:

[0058]

[0059] Preferably, Ar2 and Ar3 are each independently phenyl, phenyl substituted by 1 to 5 deuteriums, biphenyl, naphthyl, terphenyl or dimethylfluorenyl; or one of Ar2 and Ar3 is phenyl, phenyl substituted by 1 to 5 deuteriums, biphenyl, naphthyl, terphenyl or dimethylfluorenyl, and the other is combined with R to form a benzene ring; or Ar2 and Ar3 are each combined with R to form a benzene ring. Preferably, in claim 1,

[0060] different.

[0061] Preferably, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-8: [Chemical Formula 1-1]

[0062]

[0063] [Chemical formula 1-2]

[0064]

[0065] [Chemical formula 1-3]

[0066]

[0067] [Chemical formula 1-4]

[0068]

[0069] [Chemical formula 1-5]

[0070]

[0071] [Chemical formula 1-6]

[0072]

[0073] [Chemical formula 1-7]

[0074]

[0075] [Chemical formula 1-8]

[0076]

[0077] In the above chemical formulas 1-1 to 1-8,

[0078] Y1 is N,

[0079] n is an integer from 0 to 4,

[0080] X1, X2, Ar1 to Ar4, a and b are the same as defined above.

[0081] Representative examples of the compound represented by the above Chemical Formula 1 are shown below:

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] 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.

[0089] [Reaction 1]

[0090]

[0091] In the above reaction formula 1, X1, X2, R, Ar1 to Ar4, a and b are the same as those defined in the above chemical formula 1, and Z is a halogen, preferably bromine or chlorine.

[0092] The above reaction formula 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups used for the Suzuki coupling reaction can be changed according to the techniques known in the art. The above production method can be further specified in the production examples described below.

[0093] (Organic Light Emitting Devices)

[0094] 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.

[0095] 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, an electron blocking layer, a light-emitting layer, a hole blocking 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.

[0096] At this time, the organic layer including the above compound may be an electron transport layer, an electron injection layer, or an electron injection and transport layer.

[0097] In another 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 this case, the organic layer containing the compound may be an electron injection and transport layer.

[0098] 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 .

[0099] Figure 1The 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.

[0100] 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 3, an electron injection and transport layer 7, and a cathode 4. In the above structure, the compound represented by the above Chemical Formula 1 may be contained in the above hole transport layer.

[0101] 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.

[0102] 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.

[0103] 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.

[0104] 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.

[0105] 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.

[0106] 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.

[0107] 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.

[0108] 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.

[0109] 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.

[0110] The electron blocking layer is a layer formed on the hole transport layer, preferably disposed in contact with the light-emitting layer, which improves the efficiency of the organic light-emitting device by adjusting the hole mobility and preventing the excessive migration of electrons to increase the probability of hole-electron bonding. The electron blocking layer includes an electron blocking substance, and as an example of such an electron blocking substance, an arylamine-based organic substance can be used, but it is not limited thereto.

[0111] 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.

[0112] The above-mentioned light-emitting layer may include a host material and a dopant material. As the host material, there are aromatic fused ring derivatives or heterocyclic compounds. Specifically, as aromatic fused ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0113] 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.

[0114] The hole blocking layer is a layer formed on the light-emitting layer, preferably in contact with the light-emitting layer, and improves the efficiency of the organic light-emitting device by adjusting the electron mobility and preventing the excessive migration of holes to increase the probability of hole-electron bonding. The hole blocking layer contains a hole blocking substance. Examples of such a hole blocking substance include azine derivatives containing triazine, triazole derivatives, Compounds into which an electron-withdrawing group is introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, phosphine oxide derivatives, and the like.

[0115] The electron injection and transport layer is a layer that injects electrons from the electrode and transports the received electrons to the light-emitting layer, and acts as an electron transport layer and an electron injection layer at the same time, and is formed on the light-emitting layer or the hole blocking layer. Such an electron injection and transport substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and a substance with a large electron mobility is suitable. As such an electron injection and transport layer substance, a compound represented by the above chemical formula 1 can be used. As examples of other electron injection and transport substances, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, triazine derivatives, etc., but are not limited to these. Alternatively, it can also be combined with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone and the like, and derivatives thereof, metal coordination compounds, or nitrogen-containing five-membered ring derivatives and the like can be used together, but are not limited thereto.

[0116] The electron injection and transport layer may also be formed as a separate layer such as an electron injection layer and an electron transport layer. In this case, the electron transport layer is formed on the light-emitting layer or the hole blocking layer, and as the electron transport material contained in the electron transport layer, the electron injection and transport material mentioned above can be used. In addition, the electron injection layer is formed on the electron transport layer, and as the electron injection material contained in the electron injection layer, LiF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, etc. and their derivatives, metal coordination compounds and nitrogen-containing five-membered ring derivatives, etc.

[0117] 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-hydroxyquinoline) gallium chloride, bis(2-methyl-8-hydroxyquinoline)(o-cresol) gallium, bis(2-methyl-8-hydroxyquinoline)(1-naphthol) aluminum, and bis(2-methyl-8-hydroxyquinoline)(2-naphthol) gallium.

[0118] In one embodiment, the electron transport layer, the electron injection layer, or the electron injection and transport layer of the organic light-emitting device may include the compound represented by the above chemical formula 1 and the above metal coordination compound. In this case, the electron transport layer, the electron injection layer, or the electron injection and transport layer may include the compound represented by the above chemical formula 1 and the above metal coordination compound in a weight ratio of 10:90 to 90:10, a weight ratio of 30:70 to 70:30, or a weight ratio of 50:50.

[0119] 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.

[0120] In addition, the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to being included in an organic light-emitting device.

[0121] In order to help understand the present invention, preferred embodiments are provided below. However, the following embodiments are provided only to make the present invention easier to understand, and the content of the present invention is not limited thereto.

[0122] [Example]

[0123] Example 1: Preparation of Compound E1

[0124]

[0125] Under nitrogen atmosphere, E1-A (20 g, 45 mmol) and E1-B (19.6 g, 45 mmol) were added to 400 ml of distilled water. alkane (Diox), stirring and reflux. Then, potassium phosphate (28.6g, 134.9mmol) was dissolved in 29ml of water and added. After sufficient stirring, dibenzylideneacetone palladium (0.8g, 1.3mmol) and tricyclohexylphosphine (0.8g, 2.7mmol) were added. After reacting for 7 hours, the reaction mixture was cooled to room temperature and the generated solid was filtered. The solid was dissolved in 968mL of chloroform, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a yellow solid compound E1 (4.8g, 15%).

[0126] MS:[M+H] + =718

[0127] Example 2: Preparation of Compound E2

[0128]

[0129] The compound E2 was produced by the same method as in Example 1 except that the starting materials were used as in the above reaction formula.

[0130] MS:[M+H] + =718

[0131] Example 3: Preparation of Compound E3

[0132]

[0133] The compound E3 was produced by the same method as in Example 1 except that the starting materials were used as in the above reaction formula.

[0134] MS:[M+H] + =768

[0135] Example 4: Preparation of Compound E4

[0136]

[0137] The compound E4 was produced by the same method as in Example 1 except that the starting materials were used as in the above reaction formula.

[0138] MS:[M+H] + =807

[0139] Example 5: Preparation of Compound E5

[0140]

[0141] The compound E5 was produced by the same method as in Example 1 except that the starting materials were used as in the above reaction formula.

[0142] MS:[M+H] + =691

[0143] Example 6: Preparation of Compound E6

[0144]

[0145] The compound E6 was produced by the same method as in Example 1 except that the starting materials were used as in the above reaction formula.

[0146] MS:[M+H] + =718

[0147] Example 7: Preparation of Compound E7

[0148]

[0149] The compound E7 was produced by the same method as in Example 1 except that the starting materials were used as in the above reaction formula.

[0150] MS:[M+H] + =793

[0151] Example 8: Preparation of Compound E8

[0152]

[0153] The compound E8 was produced by the same method as in Example 1 except that the starting materials were used as in the above reaction formula.

[0154] MS:[M+H] + =718

[0155] Example 9: Preparation of Compound E9

[0156]

[0157] The compound E9 was produced by the same method as in Example 1 except that the starting materials were used as in the above reaction formula.

[0158] MS:[M+H] + =819

[0159] Example 10: Preparation of Compound E10

[0160]

[0161] The compound E10 was produced by the same method as in Example 1 except that the starting materials were used as in the above reaction formula.

[0162] MS:[M+H] + =870

[0163] Example 11: Preparation of Compound E11

[0164]

[0165] The compound E11 was produced by the same method as in Example 1 except that the starting materials were used as in the above reaction formula.

[0166] MS:[M+H] + =723

[0167] [Experimental example]

[0168] Experimental Example 1

[0169] 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.

[0170] 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.

[0171] 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. On the above-mentioned light-emitting layer, the compound E1 prepared in Example 1 and the following compound LiQ (lithium quinolate) were vacuum-deposited at a weight ratio of 1:1 to form a light-emitting layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A cathode is formed by evaporation with a thickness of .

[0172]

[0173] In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at 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.

[0174] Experimental Examples 2 to 11

[0175] 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 E1 in Experimental Example 1.

[0176] Comparative Experimental Examples 1 to 8

[0177] An organic light-emitting device was manufactured by the same method as in Experimental Example 1, except that the compounds in Table 1 below were used instead of Compound E1 in Experimental Example 1. Compounds ET-1 to ET-6 used in Table 1 below are as follows.

[0178]

[0179] 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 (T90) until the initial luminance reaches 90% was measured at a current density of . The results are shown in Table 1 below.

[0180]

Table 1

[0181]

[0182] As described in Table 1, it was confirmed that the organic light emitting device using the compound represented by Chemical Formula 1 of the present invention exhibited excellent characteristics in voltage, efficiency and / or lifespan (T90).

[0183] By comparing Experimental Examples 1 to 11 in Table 1 above with Comparative Experimental Examples 1 to 4, it can be confirmed that the organic light-emitting device comprising the compound of Chemical Formula 1 of the present invention shows significantly superior characteristics in terms of efficiency compared to the organic light-emitting device using a cyano compound in which one of Ar1 to Ar4 is substituted by an aromatic group having less than 10 carbon atoms.

[0184] By comparing Experimental Examples 1 to 11 and Comparative Experimental Examples 5 to 7 in Table 1 above, it can be confirmed that the organic light-emitting device including the compound of Chemical Formula 1 of the present invention shows significantly superior characteristics in terms of efficiency compared with the organic light-emitting device using a biphenylene compound different from Chemical Formula 1.

[0185] By comparing Experimental Examples 1 to 11 in Table 1 and Comparative Experimental Example 8, it can be confirmed that the organic light-emitting device including the compound of Chemical Formula 1 of the present invention exhibits significantly superior characteristics in terms of life compared to the organic light-emitting device using the compound not substituted by a cyano group.

[0186] [Explanation of symbols]

[0187] 1: Substrate 2: Anode

[0188] 3: Light-emitting layer 4: Cathode

[0189] 5: Hole injection layer 6: Hole transport layer

[0190] 7: Electron injection and transport layer.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, X1 is N or CR, and two or more of X1 are N, X2 is N or CR, and two or more of X2 are N, R is each independently hydrogen; deuterium; substituted or unsubstituted C 1-60 Alkyl; 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, or combined with any of the adjacent substituents Ar1 to Ar4 to form a substituted or unsubstituted benzene ring, Ar1 to Ar4 not bonded to R are each independently substituted or unsubstituted C 6-60 Aryl, but at least one of Ar1 to Ar4 is C substituted by cyano 10-30 Aryl, wherein The C substituted by cyano 10-30 The aryl group may be substituted with deuterium or not, a is an integer from 0 to 4, b is an integer from 0 to 4.

2. The compound according to claim 1, wherein Each R is independently hydrogen, deuterium, methyl, or a phenyl group which may be substituted with deuterium, or is combined with any of the adjacent substituents Ar1 to Ar4 to form a benzene ring which may be substituted with one or more deuteriums.

3. The compound according to claim 1, wherein None of Ar1 to Ar4 is bound to R; or One of Ar1 and Ar2 is bound to R; or One of Ar3 and Ar4 is combined with R; or One of Ar1 and Ar2 and one of Ar3 and Ar4 are each bonded to R.

4. The compound according to claim 1, wherein One or two of Ar1 to Ar4 are C substituted by cyano 10-30 Aryl.

5. The compound according to claim 1, wherein One of Ar1 to Ar4 is C substituted by cyano 10-30 Aryl; or One of Ar1 and Ar2 and one of Ar3 and Ar4 are each independently C substituted by cyano 10-30 Aryl.

6. The compound according to claim 1, wherein The C substituted by cyano 10-30 Aryl is C substituted with a cyano group 10-30 Aryl.

7. The compound according to claim 1, wherein The C substituted by cyano 10-30 The aryl group is a biphenyl group substituted by a cyano group, a naphthyl group substituted by a cyano group, a terphenyl group substituted by a cyano group, a phenylnaphthyl group substituted by a cyano group, or a naphthylphenyl group substituted by a cyano group.

8. The compound according to claim 1, wherein It is not the C substituted by cyano 10-30 Ar1 to Ar4 of the aryl group are each independently a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted naphthyl group, a deuterium-substituted or unsubstituted terphenyl group, or a deuterium-substituted or unsubstituted dimethylfluorenyl group, or combine with R to form a deuterium-substituted or unsubstituted benzene ring.

9. The compound according to claim 1, wherein Ar1 and Ar4 are each independently selected from any one of the following groups; or One of Ar1 and Ar4 is any one selected from the following groups, and the other is phenyl, phenyl substituted with 1 to 5 deuteriums, biphenyl, naphthyl, terphenyl or dimethylfluorenyl:

10. The compound according to claim 1, wherein Ar2 and Ar3 are each independently phenyl, phenyl substituted with 1 to 5 deuterium groups, biphenyl, naphthyl, terphenyl or dimethylfluorenyl; or One of Ar2 and Ar3 is phenyl, phenyl substituted by 1 to 5 deuteriums, biphenyl, naphthyl, terphenyl or dimethylfluorenyl, and the other is combined with R to form a benzene ring; or Ar2 and Ar3 each combine with R to form a benzene ring.

11. The compound according to claim 1, wherein different.

12. The compound according to claim 1, wherein The chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-8: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] [Chemical formula 1-5] [Chemical formula 1-6] [Chemical formula 1-7] [Chemical formula 1-8] In the chemical formulas 1-1 to 1-8, Y1 is N, n is an integer from 0 to 4, X1, X2, Ar1 to Ar4, a and b are the same as defined in claim 1.

13. The compound according to claim 1, wherein The compound represented by the chemical formula 1 is any one selected from the following compounds:

14. An organic light emitting device, comprising: A first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 13.

15. The organic light emitting device according to claim 14, wherein: The organic layer containing the compound is an electron injection and transport layer.

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