Compound and organic light-emitting device containing the same

Abstract

The present invention provides novel compounds and organic light-emitting devices comprising the same.

Description

Technical Field

[0001] Cross-references to related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2019-0139627 filed on November 4, 2019, 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 electroluminescent 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 1) 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] Ar1 is substituted or unsubstituted C 6-60 Aryl,

[0018] Ar2 and Ar3 are each independently hydrogen, or substituted or unsubstituted C 6-60 Aryl,

[0019] L is phenylene, biphenyldiyl, terphenyldiyl, naphthalenediyl, or phenylene substituted by naphthyl,

[0020] R1 to R4 are each independently hydrogen; deuterium; substituted or unsubstituted C 1-60 Alkyl; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 5-60 Heteroaryl,

[0021] a, b, c and d are each independently an integer from 0 to 3.

[0022] In addition, the present invention provides an organic light-emitting device, which includes: a first electrode; a second electrode opposite to the first electrode; and one or more organic layers between the first electrode and the second electrode, wherein one or more of the organic layers contains a compound represented by the chemical formula 1.

[0023] Effects of the Invention

[0024] 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, low 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

[0025] 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 .

[0026] 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 .

[0027] Figure 3The 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, an electron blocking layer 9, a light-emitting layer 7, a hole blocking layer 10, an electron transport layer 8, an electron injection layer 11 and a cathode 4. DETAILED DESCRIPTION

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

[0029] The present invention provides a compound represented by the above Chemical Formula 1.

[0030] In this manual, It represents the bond to other substituents.

[0031] In the present specification, the term "substituted or unsubstituted" means that the group is substituted or unsubstituted with one or more substituents selected from deuterium, halogen group, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, alkoxy group, aryloxy group, alkylthioxy group, arylthioxy group, alkylsulfonyl group, arylsulfoxy group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamino group, aralkylamino group, heteroarylamino group, arylamino group, arylphosphino group, or heterocyclic group containing one or more of N, O and S atoms, or substituted or unsubstituted with substituents formed by connecting two or more substituents among the substituents exemplified above. For example, the "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 in which two phenyl groups are connected.

[0032] 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 group may have the following structure, but is not limited thereto.

[0033]

[0034] 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 group may be a group of the following structural formula, but is not limited thereto.

[0035]

[0036] 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 group may have the following structure, but is not limited thereto.

[0037]

[0038] 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.

[0039] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0040] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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., but not limited thereto.

[0046] 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.

[0047] In this specification, the aryl group in aralkyl, aralkenyl, alkylaryl, and arylamine is the same as the example of the aryl group described above. In this specification, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the example of the alkyl group described above. In this specification, the heteroaryl group in heteroarylamine can be applied to the above description of the heterocyclic group. In this specification, the alkenyl group in aralkenyl is the same as the example of the alkenyl group described above. In this specification, the arylene group is a divalent group, and the above description of the aryl group can be applied. In this specification, the heteroarylene group is a divalent group, and the above description of the heterocyclic group can be applied. In this specification, the hydrocarbon ring is not a monovalent group, but two substituents are combined, and the above description of the aryl group or cycloalkyl group can be applied. In this specification, the heterocycle is not a monovalent group, but two substituents are combined, and the above description of the heterocyclic group can be applied.

[0048] Preferably, Ar1 can be substituted or unsubstituted C 6-20 Aryl, more preferably, Ar1 may be phenyl, phenyl substituted by 1 to 5 deuteriums, biphenyl or naphthyl.

[0049] Preferably, Ar2 and Ar3 may each independently be hydrogen, or a substituted or unsubstituted C 6-20 Aryl, more preferably, may be hydrogen, phenyl, phenyl substituted with 1 to 5 deuteriums; or naphthyl.

[0050] Preferably, L can be any one selected from the following groups:

[0051]

[0052] Preferably, a, b, c and d may each independently be 0 or 1, and more preferably, a, b, c and d may all be 0.

[0053] For example, the compound represented by the above Chemical Formula 1 may be selected from the following compounds:

[0054]

[0055]

[0056]

[0057]

[0058]

[0059] On the other hand, the compound represented by the above Chemical Formula 1 can be produced by a production method as shown in the following Reaction Formula 1.

[0060] [Reaction 1]

[0061]

[0062] In the above reaction formula 1, T is a halogen, preferably bromine or chlorine, and the definitions of other substituents are the same as those described above.

[0063] Specifically, the compound represented by the above chemical formula 1 is manufactured by combining the starting material through the Suzuki coupling reaction. Such a Suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group for the Suzuki coupling reaction can be changed according to the technology known in the art. The above-mentioned manufacturing method can be more specific in the manufacturing example described later.

[0064] 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 first electrode; and one or more organic layers between the first electrode and the second electrode, wherein one or more of the organic layers includes the compound represented by the above Chemical Formula 1.

[0065] The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer 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.

[0066] In addition, the above-mentioned organic layer may include a hole injection layer, a hole transport layer, a layer for simultaneous hole injection and transport, or an electron blocking layer, and the above-mentioned hole injection layer, hole transport layer, a layer for simultaneous hole injection and transport, or an electron blocking layer may contain the compound represented by the above-mentioned Chemical Formula 1.

[0067] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer may include the compound represented by the chemical formula 1. In this case, the compound represented by the chemical formula 1 may be used as a host substance in the light-emitting layer, and more specifically, the compound represented by the chemical formula 1 may be used as a host substance in the light-emitting layer of a green organic light-emitting device.

[0068] In addition, the light-emitting layer may include two or more hosts. When the light-emitting layer includes two or more hosts, one or more of the hosts may be a compound represented by Chemical Formula 1.

[0069] In addition, the above-mentioned organic layer may include a hole blocking layer, an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the above-mentioned hole blocking layer, electron transport layer, electron injection layer, or a layer that simultaneously performs electron transport and electron injection may contain the compound represented by the above-mentioned Chemical Formula 1.

[0070] In addition, the light-emitting layer may further include a compound represented by the following chemical formula 2:

[0071] [Chemical formula 2]

[0072]

[0073] In the above chemical formula 2,

[0074] Ar4 and Ar5 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 5-60 Heteroaryl,

[0075] R5 and R6 are each independently hydrogen; deuterium; halogen; cyano; nitro; amino; substituted or unsubstituted C 1-60 Alkyl; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 2-60 Alkenyl; substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 5-60 Heteroaryl,

[0076] e and f are each independently an integer from 0 to 7.

[0077] Preferably, Ar4 and Ar5 can each independently be a substituted or unsubstituted C 6-20 Aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 5-20 The heteroaryl group may more preferably be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothienyl group or a dimethylfluorenyl group.

[0078] Preferably, R5 and R6 may both be hydrogen.

[0079] For example, the compound represented by the above Chemical Formula 2 may be selected from the following compounds:

[0080]

[0081]

[0082]

[0083]

[0084] 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 a reverse 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. Figures 1 to 3 .

[0085] 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.

[0086] 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.

[0087] Figure 3 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, an electron blocking layer 9, a light-emitting layer 7, a hole blocking layer 10, an electron transport layer 8, an electron injection layer 11, 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, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, and electron injection layer.

[0088] 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.

[0089] 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.

[0090] 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.

[0091] 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.

[0092] 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.

[0093] 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.

[0094] 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.

[0095] 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.

[0096] 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. A material with a large hole mobility is suitable. Specific examples include arylamine organics, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited thereto.

[0097] The electron blocking layer is formed on the hole transport layer, preferably in contact with the light-emitting layer, and improves the probability of hole-electron bonding by adjusting the hole mobility and preventing excessive electron migration, thereby improving the efficiency of the organic light-emitting device. The electron blocking layer contains an electron blocking substance, and as such an electron blocking substance, a substance having a stable structure that prevents electrons from flowing out of the light-emitting layer is suitable. As a specific example, an arylamine-based organic substance can be used, but it is not limited to this.

[0098] The above-mentioned 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 preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo azole, benzothiazole and benzimidazole compounds; poly(p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorene; rubrene, etc., but are not limited thereto.

[0099] The 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 the aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as the heterocyclic compound, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but it is not limited thereto.

[0100] 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.

[0101] The hole blocking layer is formed on the light-emitting layer. Specifically, the hole blocking layer is provided in contact with the light-emitting layer, and improves the probability of hole-electron combination by preventing excessive migration of holes, thereby improving the efficiency of the organic light-emitting device. The hole blocking layer contains a hole blocking substance. As such a hole blocking substance, a substance having a stable structure that prevents holes from flowing out of the light-emitting layer is suitable. As the hole blocking substance, azine derivatives including triazine; triazole derivatives; Compounds into which electron-withdrawing groups are introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, and phosphine oxide derivatives.

[0102] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. As an electron transport material, it 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 together 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.

[0103] 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.

[0104] 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.

[0105] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0106] 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.

[0107] 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.

[0108] [Synthesis example]

[0109] Synthesis Example 1: Synthesis of Intermediate A

[0110] Step 1) Synthesis of intermediate A-1

[0111]

[0112] Under nitrogen atmosphere, 2,4,6-trichloro-1,3,5-triazine (15 g, 81.3 mmol) and dibenzo[b,d]thiophen-4-yl boronicacid (18.6 g, 81.3 mmol) were added to 225 ml of THF, stirred and refluxed. Then, potassium carbonate (33.7 g, 244 mmol) was dissolved in 101 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (0) (2.8 g, 2.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. The product was dissolved in chloroform again, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.5 g of intermediate A-1. (Yield 72%, MS: [M+H] + =333).

[0113] Step 2) Synthesis of Intermediate A

[0114]

[0115] Under a nitrogen atmosphere, intermediate A-1 (15 g, 45.2 mmol) and phenylboronic acid (5.5 g, 45.2 mmol) were added to 225 ml of THF, stirred and refluxed. Then, potassium carbonate (18.7 g, 135.5 mmol) was dissolved in 56 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.4 mmol) was added. After reacting for 9 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, 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 purified by silica gel column chromatography to produce 12.2 g of intermediate A. (Yield 72%, MS: [M+H] + =375).

[0116] Synthesis Example 2: Synthesis of Intermediate B

[0117]

[0118] In step 2 of Synthesis Example 1, intermediate B was produced by the same production method as the production method of intermediate A, except that [1,1'-biphenyl]-3-ylboronic acid was used instead of phenylboronic acid. (MS[M+H] + =451).

[0119] Synthesis Example 3: Synthesis of Intermediate C

[0120]

[0121] In Synthesis Example 1, Intermediate C was produced by the same production method as that of Intermediate A, except that (9-phenyldibenzo[b,d]thiophen-4-yl)boronic acid was used instead of dibenzo[b,d]thiophen-4-ylboronic acid and [1,1'-biphenyl]-3-ylboronic acid was used instead of phenylboronic acid. (MS[M+H] + =527).

[0122] Synthesis Example 4: Synthesis of Intermediate D

[0123]

[0124] In Synthesis Example 1, Intermediate D was produced by the same production method as that of Intermediate A, except that (6-phenyldibenzo[b,d]thiophen-4-yl)boronic acid was used instead of dibenzo[b,d]thiophen-4-ylboronic acid. (MS[M+H] + =451).

[0125] Synthesis Example 5: Synthesis of Intermediate E

[0126]

[0127] Intermediate E was produced by the same production method as the production method of Intermediate A except that (phenyl-d5)boronic acid was used in place of phenylboronic acid in Step 2 of Synthesis Example 1. (MS[M+H] + =380).

[0128] Synthesis Example 6: Synthesis of Intermediate F

[0129]

[0130] In Synthesis Example 1, Intermediate F was produced by the same production method as the production method of Intermediate A, except that (6-(phenyl-d5)dibenzo[b,d]thiophen-4-yl)boronic acid was used instead of dibenzo[b,d]thiophen-4-ylboronic acid. (MS[M+H] + =456).

[0131] Synthesis Example 7: Synthesis of Compound 1

[0132]

[0133] Under a nitrogen atmosphere, intermediate A (15 g, 40.1 mmol) and intermediate a (11.6 g, 40.1 mmol) were added to 225 ml of THF, stirred and refluxed. Then, potassium carbonate (16.6 g, 120.4 mmol) was dissolved in 50 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.4 g, 1.2 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, 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. After the concentrated compound was purified by silica gel column chromatography, 7.2 g of compound 1 was produced by sublimation purification. (Yield 31%, MS: [M+H] + =583).

[0134] Synthesis Example 8: Synthesis of Compound 2

[0135]

[0136] In Synthesis Example 7, except that Intermediate b was used instead of Intermediate a, Compound 2 was produced by the same production method as that of Compound 1. (MS[M+H] + =659).

[0137] Synthesis Example 9: Synthesis of Compound 3

[0138]

[0139] In Synthesis Example 7, except that Intermediate B was used instead of Intermediate A, Compound 3 was produced by the same production method as that of Compound 1. (MS[M+H] + =659).

[0140] Synthesis Example 10: Synthesis of Compound 4

[0141]

[0142] In Synthesis Example 7, except that Intermediate C was used instead of Intermediate A, Compound 4 was produced by the same production method as that of Compound 1. (MS[M+H] + =735).

[0143] Synthesis Example 11: Synthesis of Compound 5

[0144]

[0145] In Synthesis Example 7, except that Intermediate D was used instead of Intermediate A, Compound 5 was produced by the same production method as that of Compound 1. (MS[M+H] + =659).

[0146] Synthesis Example 12: Synthesis of Compound 6

[0147]

[0148] In Synthesis Example 7, except that Intermediate E was used instead of Intermediate A and Intermediate c was used instead of Intermediate a, Compound 6 was produced by the same production method as that of Compound 1. (MS[M+H] + =664).

[0149] Synthesis Example 13: Synthesis of Compound 7

[0150]

[0151] In Synthesis Example 7, except that Intermediate F was used instead of Intermediate A and Intermediate d was used instead of Intermediate a, Compound 7 was produced by the same production method as that of Compound 1. (MS[M+H] + =664).

[0152] [Experimental example]

[0153] Experimental Example 1

[0154] ITO (Indium Tin Oxide) The glass substrate coated with a film of a thickness of 10000 is placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent uses a product of Fischer Co., and the distilled water uses distilled water filtered twice by a filter manufactured by Millipore Co. After the ITO is washed for 30 minutes, ultrasonic washing is repeated twice with distilled water for 10 minutes. After the distilled water washing is completed, ultrasonic washing is 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 is cleaned for 5 minutes using oxygen plasma, the substrate is transported to a vacuum evaporator.

[0155] On the thus prepared ITO transparent electrode, the following HT-A compound and the following PD compound were added at a weight ratio of 95:5 and Then, only the following HT-A compound is deposited with a thickness of The hole transport layer was formed by evaporation of a thickness of 1000 nm. On the hole transport layer, the following HT-B compound was deposited at On the electron blocking layer, the compound 1 prepared above and the following GD compound were added at a weight ratio of 85:15 and The following ET-A compound was deposited on the luminous layer in a vacuum evaporation process with a thickness of 1000 nm. On the hole blocking layer, the following ET-B compound and the following Liq compound were added at a weight ratio of 2:1 and Then, LiF and magnesium were deposited at a weight ratio of 1:1 and The electron transport and injection layer is formed by vacuum evaporation of a thickness of 1:1. On the electron injection layer, magnesium and silver are deposited in a weight ratio of 1:4 and A cathode is formed by evaporation with a thickness of , thereby manufacturing an organic light-emitting device.

[0156]

[0157] In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at cathode maintains The evaporation rate of silver and magnesium is maintained The evaporation speed is 2×10 -7 ~5×10 -6 A support is provided to produce an organic light-emitting device.

[0158] Experimental Examples 2 to 7

[0159] An organic light-emitting device was manufactured by the same method as in Experimental Example 1 except that the compounds described in Table 1 below were used instead of Compound 1.

[0160] Experimental Examples 8 to 11

[0161] An organic light-emitting device was manufactured by the same method as in Experimental Example 1 except that the compounds described in Table 1 below were used instead of Compound 1. The ratio of each compound in Table 1 below refers to a weight ratio, and Compounds PGH-1 and PGH-2 are shown below.

[0162]

[0163] Comparative Experimental Examples 1 to 4

[0164] An organic light-emitting device was manufactured by the same method as in Experimental Example 1 except that the compounds described in Table 1 below were used instead of Compound 1. In Table 1 below, compounds GH-A, GH-B, GH-C, and GH-D are respectively as shown below.

[0165]

[0166] Comparison of Experimental Examples 5 and 6

[0167] An organic light-emitting device was manufactured by the same method as in Experimental Example 1 except that the compounds described in Table 1 below were used instead of Compound 1. The ratio of each compound in Table 1 below refers to a weight ratio, and compounds GH-A, GH-C, PGH-1, and PGH-2 are the same as described above.

[0168] The voltage, efficiency, and life (T95) of the organic light-emitting devices manufactured in the above-mentioned experimental examples and comparative experimental examples were measured by applying current. The results are shown in Table 1 below. The voltage and efficiency were measured by applying 10 mA / cm 2 In addition, T95 in Table 1 below refers to the current density of 20 mA / cm 2 The time taken for the initial brightness to drop to 95% is measured.

[0169] [Table 1]

[0170]

[0171] As shown in Table 1 above, it can be seen that Experimental Examples 1 to 7 using a compound of [Chemical Formula 1] in which 4-dibenzothiophene is substituted in triazine and 3-dibenzofuran having a connecting group is substituted on the other side have improved performance in terms of driving voltage, efficiency, and life compared to Comparative Experimental Examples 1 to 4.

[0172] The distribution of molecular orbitals of dibenzothiophene and dibenzofuran is different from each other. The 4th position of dibenzothiophene and the 3rd position of dibenzofuran are both positions where HOMO and LUMO are distributed simultaneously. When the position is substituted, it plays a favorable role in the distribution and migration of electrons in the molecule, so the injection, transmission and stability of the charge are improved. Moreover, it can be confirmed that when used as a main body together with the compound represented by Chemical Formula 2 of the present invention, it is also conducive to the formation of an exciplex, thereby showing the characteristic effects of low voltage, high efficiency and long life to a greater extent.

[0173] [Explanation of symbols]

[0174] 1: Substrate 2: Anode

[0175] 3: Light-emitting layer 4: Cathode

[0176] 5: Hole injection layer 6: Hole transport layer

[0177] 7: Light-emitting layer 8: Electron transport layer

[0178] 9: Electron blocking layer 10: Hole blocking layer

[0179] 11: Electron injection layer.

Claims

1. A compound represented by the following chemical formula 1: Chemical formula 1 In the chemical formula 1, Ar1 is phenyl, phenyl substituted by 1 to 5 deuteriums, biphenyl or naphthyl, Ar2 and Ar3 are each independently hydrogen, phenyl, phenyl substituted with 1 to 5 deuteriums, or naphthyl, L is phenylene, biphenyldiyl, terphenyldiyl, naphthalenediyl, or phenylene substituted by naphthyl, R1 to R4 are each independently hydrogen; or deuterium; a, b, c and d are each independently an integer from 0 to 3.

2. The compound according to claim 1, wherein L is any one selected from the following groups:

3. The compound according to claim 1, wherein a, b, c and d are all 0.

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

5. An organic light-emitting device, wherein: include: a first electrode; a second electrode disposed opposite to the first electrode; and comprising one or more organic layers 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 4.

6. The organic light emitting device according to claim 5, wherein: The organic layer containing the compound is a light-emitting layer.

7. The organic light emitting device according to claim 6, wherein: The light-emitting layer further comprises a compound represented by the following Chemical Formula 2: Chemical formula 2 In the chemical formula 2, Ar4 and Ar5 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 5-60 Heteroaryl, R5 and R6 are each independently hydrogen; deuterium; halogen; cyano; nitro; amino; substituted or unsubstituted C 1-60 Alkyl; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 2-60 Alkenyl; substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 5-60 Heteroaryl, e and f are each independently an integer from 0 to 7, The term "substituted or unsubstituted" refers to being substituted or unsubstituted with one or more substituents 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, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, or a heterocyclic group containing one or more of N, O and S atoms, or being substituted with a substituent formed by connecting two or more of the above substituents. Wherein the ester group is selected from the following groups:

8. The organic light emitting device according to claim 7, wherein: Ar4 and Ar5 are each independently phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl or dimethylfluorenyl.

9. The organic light emitting device according to claim 7, wherein: R5 and R6 are both hydrogen.

10. The organic light emitting device according to claim 7, wherein: The compound represented by the chemical formula 2 is any one selected from the following compounds:

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