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. 10-2023-0035468 filed on March 17, 2023 and Korean Patent Application No. 10-2024-0021745 filed on February 15, 2024, and incorporates all the contents disclosed in the documents of the Korean patent applications as part of this specification.

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

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

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

[0006] As for organic substances used for organic light-emitting devices as described above, development of new materials 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 invention relates to a novel organic light-emitting material and an organic light-emitting device 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 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 Heteroaryl,

[0018] R1 to R8 are each independently hydrogen; deuterium; substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 heteroaryl, and at least one of R1 to R8 is deuterium,

[0019] One of Ra to Rd is a substituent represented by the following Chemical Formula 2, and the others are each independently hydrogen or deuterium,

[0020] [Chemical formula 2]

[0021] *-L-R9

[0022] In the above chemical formula 2,

[0023] * is the position connected to the above chemical formula 1,

[0024] L is substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing any one or more selected from N, O and S 2-60 Heteroarylene,

[0025] R9 is substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 Heteroaryl.

[0026] 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.

[0027] Effects of the Invention

[0028] 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, luminescence, electron transport and / or electron injection. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Figure 1 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 is shown.

[0030] 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, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10 and a cathode 4. DETAILED DESCRIPTION

[0031] In the following, the present invention will be described in more detail to help understanding the present invention.

[0032] The present invention provides a compound represented by the above Chemical Formula 1.

[0033] In this manual, or It represents the bond to other substituents.

[0034] 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 heteroaryl 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, a biphenyl group may be an aryl group, or may be interpreted as a substituent formed by connecting two phenyl groups. As an example, the term "substituted or unsubstituted" may be understood as "unsubstituted or selected from deuterium; halogen; C 1-10 Alkyl; C 1-10 Alkoxy; C 6-20 Aryl; and C containing one or more heteroatoms selected from N, O and S 2-20In the present specification, the term “substituted by one or more substituents” may be understood as meaning, for example, “substituted by 1 to 5 substituents” or “substituted by 1 or 2 substituents”.

[0035] 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.

[0036]

[0037] 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 substituents may be of the following structural formulas, but are not limited thereto.

[0038]

[0039] 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.

[0040]

[0041] 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.

[0042] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0043] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0044] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl, but are not limited thereto.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] In the present specification, the heteroaryl group is a heteroaryl 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. According to one embodiment, the number of carbon atoms of the heteroaryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the heteroaryl group is 6 to 20. Examples of the heteroaryl 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.

[0050] 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 heteroaryl 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 heteroaryl group can be applied. In the present specification, the hydrocarbon ring is not a monovalent group, but is formed by combining two substituents, and the above-mentioned description of the aryl group or the cycloalkyl group can be applied. In the present specification, the heteroaryl group is not a monovalent group, but is formed by combining two substituents, and the above-mentioned description of the heteroaryl group can be applied.

[0051] Preferably, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 Heteroaryl.

[0052] More preferably, Ar1 and Ar2 may each independently be a phenyl group, a biphenyl group, a carbazolyl group, a dibenzofuranyl group or a dibenzothiophenyl group, and the above Ar1 and Ar2 may each independently be unsubstituted or substituted with one or more deuterium groups.

[0053] Preferably, at least one of Ar1 and Ar2 may be a phenyl group which is unsubstituted or substituted with one or more deuterium groups.

[0054] Preferably, R1 to R8 are each independently hydrogen; deuterium; substituted or unsubstituted C 6-20 Aryl; or a substituted or unsubstituted C 2-20 The invention further comprises a heteroaryl group, and at least one of R1 to R8 may be deuterated.

[0055] More preferably, R1 to R8 can each independently be hydrogen, deuterium, dibenzofuranyl, dibenzothienyl or phenylcarbazolyl, and the above phenyl, dibenzofuranyl, dibenzothienyl and phenylcarbazolyl can be unsubstituted or substituted by one or more deuteriums, and at least one of R1 to R8 can be deuterium.

[0056] Preferably, six or more of R1 to R8 may be deuterium.

[0057] More preferably, 7 or more of R1 to R8 may be deuterium.

[0058] Preferably, one of Ra to Rd is a substituent represented by the above Chemical Formula 2, and the others may each be hydrogen.

[0059] Preferably, L can be substituted or unsubstituted C 6-20 or a substituted or unsubstituted C containing any one or more selected from N, O and S 2-20 Heteroarylene.

[0060] More preferably, L may be phenylene, naphthalene diyl, anthracene diyl, dibenzothiophene diyl or carbazole diyl, and the above L may be unsubstituted or substituted with one or more deuterium groups.

[0061] Most preferably, L may be a phenylene group, a dibenzofurandiyl group or a carbazolediyl group.

[0062] Preferably, R9 can be substituted or unsubstituted C 6-20 Aryl; or a substituted or unsubstituted C 2-20 Heteroaryl.

[0063] More preferably, it may be a substituted or unsubstituted C 2-20 Heteroaryl.

[0064] More preferably, R9 may be phenyl, carbazolyl, dibenzofuranyl, dibenzothienyl or phenyldibenzothienyl, and the above R9 may be unsubstituted or substituted with one or more deuteriums.

[0065] Most preferably, R9 may be phenyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl.

[0066] Representative examples of the compound represented by the above Chemical Formula 1 are shown below:

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082] As an example, the compound represented by the above Chemical Formula 1 can be produced by the production method shown in the following Reaction 1, and the remaining compounds can also be produced by similar methods.

[0083] [Reaction 1]

[0084]

[0085] In the above reaction formula 1, R1 to R8, Ra to Rd, Ar1 and Ar2 are the same as those defined in the above chemical formula 1, and X is a halogen, preferably, X is chlorine or bromine.

[0086] The above reaction formula 1 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used for the amine substitution 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.

[0087] 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.

[0088] 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.

[0089] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1.

[0090] In addition, the organic layer may include a hole transport layer, a hole injection layer, or a layer that simultaneously transports and injects holes, and the hole transport layer, the hole injection layer, or the layer that simultaneously transports and injects holes may include the compound represented by Chemical Formula 1.

[0091] In addition, the organic layer may include an electron transport layer, an electron injection layer, or an electron injection and transport layer, and the electron transport layer, the electron injection layer, or the electron injection and transport layer may include the compound represented by Chemical Formula 1.

[0092] 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 Figure 2 .

[0093] Figure 1 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 is shown. 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, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10 and a cathode 4.

[0094] In the structure as described above, the compound represented by the above Chemical Formula 1 may be included in the above light emitting layer.

[0095] 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.

[0096] 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.

[0097] 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.

[0098] 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.

[0099] 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.

[0100] 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.

[0101] 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.

[0102] 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.

[0103] 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.

[0104] The electron blocking layer is a layer placed between the hole transport layer and the light-emitting layer to prevent the electrons injected from the cathode from being transferred to the hole transport layer without being recombined in the light-emitting layer, and is also called an electron suppression layer or an electron blocking layer. It is preferred to use a substance with a lower electrophilicity than that of the electron transport layer in the electron blocking layer.

[0105] 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.

[0106] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material includes an aromatic fused ring derivative or a heterocyclic compound. Specifically, as an aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0107] 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.

[0108] The hole blocking layer is a layer placed between the electron transport layer and the light emitting layer to prevent the holes injected from the anode from being transferred to the electron transport layer without recombination in the light emitting layer. It is also called a hole suppression layer or a hole blocking layer. It is preferred to use a material with high ionization energy in the hole blocking layer.

[0109] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer. Materials with large electron mobility are suitable. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are common materials with low work function and accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.

[0110] The electron injection layer is a layer for injecting electrons from the electrode, and preferably uses the following compounds: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have 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.

[0111] 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.

[0112] On the other hand, in the present invention, the "electron injection and transport layer" is a layer that functions as both the electron injection layer and the electron transport layer, and substances that function as the above layers may be used alone or in combination, but are not limited thereto.

[0113] 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.

[0114] 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 being included in an organic light-emitting device.

[0115] The following examples are provided to help understand the present invention in more detail. However, the following examples are only used to illustrate the present invention, and the content of the present invention is not limited to the following examples.

[0116] [Manufacturing example]

[0117] Preparation Example 1: Preparation of Compound S1

[0118]

[0119] Step 1) Preparation of compound S1-1

[0120] Under nitrogen atmosphere, (5-chloro-2-fluorophenyl)boronic acid (40 g, 229.4 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (61.4 g, 229.4 mmol) were added to 600 ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (95.1 g, 688.2 mmol) was dissolved in 95 ml of water and added. After sufficient stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (3.4 g, 4.6 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The product was again put into 830 mL of toluene to dissolve, washed with water twice, and then the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by passing through a silica gel column using toluene and ethyl acetate to produce a gray solid compound S1-1 (63.9 g, 77%, MS: [M+H] + =362.8).

[0121] Step 2) Preparation of compound S1

[0122] Under nitrogen atmosphere, S1-1 (30 g, 82.9 mmol) and bis(pinacolato)diboron (23.2 g, 99.5 mmol) were added to 450 ml of distilled water. alkane (Diox), stirring and reflux. Then, potassium acetate (23.9 g, 248.8 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (1.4 g, 2.5 mmol) and tricyclohexylphosphine (1.4 g, 5 mmol) were added. After reacting for 6 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was again put into 451 mL of chloroform to dissolve, and after washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to produce a yellow solid compound S1 (32.4 g, 72%, MS: [M+H] + =544.4).

[0123] Preparation Example 2: Preparation of Compound S2

[0124]

[0125] Compound S2 (39.4 g, 75%, MS: [M+H]) was prepared by the same method as that of Compound S1 except that 9-(4-chloro-6-phenyl-1,3,5-triazine-2-yl)-9H-carbazole was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in Preparation Example 1. + =543.4).

[0126] Preparation Example 3: Preparation of Compound S3

[0127]

[0128] Compound S3 (46.2 g, 79%, MS: [M+H]) was prepared by the same method as that of Compound S1 except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in Preparation Example 1. + =530.4).

[0129] Preparation Example 4: Preparation of Compound S4

[0130]

[0131] Compound S4 (34.7 g, 77%, MS: [M+H]) was prepared by the same method as that of Compound S1 except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine in Preparation Example 1. + =544.4).

[0132] Preparation Example 5: Preparation of Compound S5

[0133]

[0134] Compound S5 (32.1 g, 70%, MS: [M+H]) was prepared by the same method as that of Compound S1 except that (3-chloro-2-fluorophenyl)boronic acid was used instead of (5-chloro-2-fluorophenyl)boronic acid in Preparation Example 1. + =453).

[0135] [Synthesis example]

[0136] Synthesis Example 1: Synthesis of Compound 1

[0137]

[0138] Step 1) Synthesis of Int1

[0139] Under nitrogen atmosphere, compound S1 (30 g, 66.2 mmol) and 9-(3-bromophenyl)-9H-carbazole (9-(3-bromophenyl)-9H-carbazole) (21.3 g, 66.2 mmol) were added to 300 ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (27.4 g, 198.5 mmol) was dissolved in 27 ml of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0.7 g, 1.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature and the generated solid was filtered. The solid was added to 1882 mL of chloroform and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column using chloroform and ethyl acetate to produce a gray solid compound Int1 (31.6 g, 84%, MS: [M+H] + =569.7).

[0140] Step 2) Synthesis of Compound 1

[0141] Under nitrogen atmosphere, compound Int1 (25 g, 44 mmol) and 9H-carbazole-d6 (7.6 g, 44 mmol) were added to 200 ml of dimethylformamide, stirred and refluxed. Then, potassium phosphate (28 g, 131.9 mmol) was added, stirred thoroughly, reacted for 3 hours, cooled to room temperature, filtered the organic layer to remove salt, and then the filtered organic layer was distilled. It was added again to 952 mL of chloroform to dissolve, washed with water twice, separated the organic layer, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column using chloroform and ethyl acetate to produce a yellow solid compound 1 (19.7 g, 62%, MS: [M+H] + =722.9).

[0142] Synthesis Example 2: Synthesis of Compound 2

[0143]

[0144] In Synthesis Example 1, except that 9-(2-bromophenyl)-9H-carbazole was used instead of 9-(3-bromophenyl)-9H-carbazole, a compound 2 (22.5 g, 71%, MS: [M+H]) was prepared by the same method as the method for preparing compound 1. + =722.9).

[0145] Synthesis Example 3: Synthesis of Compound 3

[0146]

[0147] In Synthesis Example 1, except that 9H-carbazole-d6 was replaced with 3-phenyl-9H-carbazole-d12, compound 3 (27.6 g, 78%, MS: [M+H] + =805).

[0148] Synthesis Example 4: Synthesis of Compound 4

[0149]

[0150] In Synthesis Example 1, except that 9-(3-bromophenyl)-9H-carbazole was replaced by 3-(4-chlorophenyl)dibenzo[b,d]furan and 9H-carbazole-d6 was replaced by 9H-carbazole-d8, a compound 4 (17.2 g, 54%, MS: [M+H]) was prepared by the same method as the method for preparing compound 1. + =725.9).

[0151] Synthesis Example 5: Synthesis of Compound 5

[0152]

[0153] In Synthesis Example 1, except that 9-(3-bromophenyl)-9H-carbazole was replaced by 4-bromo-6-phenyldibenzo[b,d]thiophene and 9H-carbazole-d6 was replaced by 9H-carbazole-d8, a compound 5 (20.5 g, 63%, MS: [M+H]) was prepared by the same method as the method for preparing compound 1. + =742).

[0154] Synthesis Example 6: Synthesis of Compound 6

[0155]

[0156] In Synthesis Example 1, except that 9-(3-bromophenyl)-9H-carbazole was replaced by 3-bromo-9-phenyl-9H-carbazole and 9H-carbazole-d6 was replaced by 9H-carbazole-d8, a compound 6 (19.1 g, 60%, MS: [M+H]) was prepared by the same method as the method for preparing compound 1. + =724.9).

[0157] Synthesis Example 7: Synthesis of Compound 7

[0158]

[0159] Step 1) Synthesis of compound Int6

[0160] Under nitrogen atmosphere, compound S2 (35 g, 64.5 mmol) and 9-(3-bromophenyl)-9H-carbazole (20.8 g, 64.5 mmol) were added to 350 ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (26.8 g, 193.6 mmol) was dissolved in 27 ml of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0.7 g, 1.3 mmol) was added. After reacting for 3 hours, the resulting solid was filtered after cooling to room temperature. The solid was added to 2122 mL of chloroform and dissolved. After washing 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 using chloroform and ethyl acetate to produce a gray solid compound Int6 (33.5 g, 79%, MS: [M+H] + =658.8).

[0161] Step 2) Synthesis of Compound 7

[0162] Under a nitrogen atmosphere, compound Int6 (25 g, 38 mmol) and 9H-carbazole-d8 (6.7 g, 38 mmol) were added to 200 ml of dimethylformamide, stirred and refluxed. Then, potassium phosphate (24.2 g, 114 mmol) was added, stirred thoroughly, reacted for 3 hours, cooled to room temperature, filtered the organic layer to remove the salt, and then the filtered organic layer was distilled. It was put into 927 mL of chloroform again to dissolve, washed with water twice, separated the organic layer, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column using chloroform and ethyl acetate to produce a yellow solid compound 7 (16.4 g, 53%, MS: [M+H] + =814).

[0163] Synthesis Example 8: Synthesis of Compound 8

[0164]

[0165] In Synthesis Example 7, except that 9H-carbazole-d8 was replaced with 3-phenyl-9H-carbazole-d12, compound 8 (18 g, 53%, MS: [M+H] + =894.1).

[0166] Synthesis Example 9: Synthesis of Compound 9

[0167]

[0168] In Synthesis Example 7, Compound 9 (22.8 g, 75%, MS: [M+H]) was prepared by the same production method as that of Compound 1, except that Compound S2 was used in place of Compound S3. + =801).

[0169] Synthesis Example 10: Synthesis of Compound 10

[0170]

[0171] In Synthesis Example 7, Compound S2 was replaced by Compound S3, and 9-(3-bromophenyl)-9H-carbazole was replaced by 9-(2-bromophenyl)-9H-carbazole. Compound 10 (24 g, 79%, MS: [M+H]) was prepared by the same method as that of Compound 1. + =801).

[0172] Synthesis Example 11: Synthesis of Compound 11

[0173]

[0174] In Synthesis Example 7, Compound 12 (16.4 g, 53%, MS: [M+H]) was prepared by the same production method as that of Compound 1, except that Compound S2 was used in place of Compound S4. + =815).

[0175] Synthesis Example 12: Synthesis of Compound 12

[0176]

[0177] In Synthesis Example 7, Compound S2 was replaced by Compound S4, and 9-(3-bromophenyl)-9H-carbazole was replaced by 9-(2-bromophenyl)-9H-carbazole. Compound 12 (15.8 g, 51%, MS: [M+H]) was prepared by the same method as that of Compound 1. + =815).

[0178] Synthesis Example 13: Synthesis of Compound 13

[0179]

[0180] In Synthesis Example 1, except that 9H-carbazole-d6 was replaced with 9H-carbazole-d8, a compound 13 (15.5 g, 50%, MS: [M+H]) was prepared by the same method as that of the compound 1. + =723).

[0181] Synthesis Example 14: Synthesis of Compound 14

[0182]

[0183] In Synthesis Example 7, Compound 14 (12.1 g, 40%, MS: [M+H]) was prepared by the same production method as that of Compound 1, except that Compound S2 was replaced by Compound S5. + =723).

[0184] [Example]

[0185] Example 1: Fabrication of an organic light-emitting device

[0186] ITO (Indium Tin Oxide) 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.

[0187] On the ITO transparent electrode prepared in this way, the following compound HT-A and the following compound PD were mixed at a weight ratio of 95:5 and at a ratio of 1:1. Then, only the following compound HT-A was 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 compound HT-B was deposited at a thickness of On the electron blocking layer, the compound 1 prepared above and the following compound GD were added at a weight ratio of 85:15 and 1:1. The following compound ET-A was deposited on the luminescent layer in a thickness of On the hole blocking layer, the following compound ET-B and the following compound Liq were added at a weight ratio of 2:1 and at a thickness of 1:1. Then, LiF and magnesium were deposited at a weight ratio of 1:1. 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.

[0188]

[0189] In the above process, the evaporation rate of organic matter is maintained The evaporation rate of magnesium and silver is maintained During evaporation, the vacuum degree is maintained at 2*10 -7 ~5*10 -6 A support is provided to produce an organic light-emitting device.

[0190] Examples 2 to 14 and Comparative Examples 1 to 11

[0191] Organic light-emitting devices of Examples 2 to 14 and Comparative Examples 1 to 11 were prepared in the same manner as in Example 1 except that the host material was changed as shown in Table 1. In Table 1, compounds GH-A to GH-K are shown below.

[0192]

[0193] [Experimental example]

[0194] The voltage, efficiency, and life (T95) of the organic light-emitting devices manufactured in the above-mentioned examples and comparative 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 The T95 in Table 1 below refers to the current density at 20 mA / cm 2 The time required for the initial brightness to decrease to 95% was measured at a current density of 1.54 W / m.

[0195] [Table 1]

[0196]

[0197] In the molecule of the compound represented by Chemical Formula 1, the polycyclic nitrogen-containing heterocyclic substituent functioning as an electron donor and the monocyclic nitrogen-containing heterocyclic ring functioning as an electron acceptor are bonded to each other at ortho positions, and thus intra charge transfer can be easily performed.

[0198] In addition, the compound in which the nitrogen-containing heterocyclic rings that function as electron donors are bonded to each other at the para position has high molecular stability, which is advantageous for the transport of holes and electrons.

[0199] Therefore, as shown in the above Table 1, it can be confirmed that when the compound of Chemical Formula 1 is used as a host of an organic light-emitting device, it exhibits characteristics of low voltage, high efficiency, and long life.

[0200] [Explanation of symbols]

[0201] 1: Substrate 2: Anode

[0202] 3: Light-emitting layer 4: Cathode

[0203] 5: Hole injection layer 6: Hole transport layer

[0204] 7: Electron blocking layer 8: Hole blocking layer

[0205] 9: Electron transport layer 10: Electron injection layer.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 Heteroaryl, R1 to R8 are each independently hydrogen; deuterium; substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 heteroaryl, and at least one of R1 to R8 is deuterium, One of Ra to Rd is a substituent represented by the following Chemical Formula 2, and the others are each independently hydrogen or deuterium, [Chemical formula 2] <h2 style=";text-align:left;direction:ltr"> ＊ <h2 style=";text-align:left;direction:ltr"> -L-R9 In the chemical formula 2, * is the position connected to the chemical formula 1, L is substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing any one or more selected from N, O and S 2-60 Heteroarylene, R9 is substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 Heteroaryl.

2. The compound according to claim 1, wherein Ar1 and Ar2 are each independently phenyl, biphenyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl, The Ar1 and Ar2 are each independently unsubstituted or substituted with one or more deuterium.

3. The compound according to claim 1, wherein At least one of Ar1 and Ar2 is a phenyl group which is unsubstituted or substituted with one or more deuterium groups.

4. The compound according to claim 1, wherein R1 to R8 are each independently hydrogen, deuterium, phenyl, dibenzofuranyl, dibenzothienyl or phenylcarbazolyl, wherein the phenyl, dibenzofuranyl, dibenzothienyl and phenylcarbazolyl are unsubstituted or substituted with one or more deuteriums, And at least one of R1 to R8 is deuterium.

5. The compound according to claim 1, wherein Seven or more of R1 to R8 are deuterium.

6. The compound according to claim 1, wherein One of Ra to Rd is a substituent represented by the Chemical Formula 2, and the others are each hydrogen.

7. The compound according to claim 1, wherein L is phenylene, naphthalene diyl, anthracene diyl, dibenzothiophene diyl or carbazole diyl, The L is unsubstituted or substituted with more than one deuterium.

8. The compound according to claim 1, wherein R9 is phenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl or phenyldibenzothiophenyl, The R9 is unsubstituted or substituted with one or more deuterium.

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

10. 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 9.

11. The organic light emitting device according to claim 10, wherein: The organic layer is a light-emitting layer.

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