Novel compound and organic light emitting device comprising the same

Abstract

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

Description

Technology Field

[0001] The present invention relates to a novel compound and an organic light-emitting device containing the same. Background Technology

[0003] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting diodes (OLEDs) utilizing this phenomenon possess wide viewing angles, excellent contrast, and fast response times, and are being extensively researched due to their superior characteristics in terms of brightness, driving voltage, and response speed.

[0005] Organic light-emitting diodes generally have a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode. To increase the efficiency and stability of the organic light-emitting diode, the organic layer is often composed of a multilayer structure made of different materials, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light-emitting diode, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed, and light is emitted when this exciton falls back to the ground state.

[0007] There is a continuous demand for the development of new materials for organic materials used in organic light-emitting devices as described above. Prior art literature

[0009] Korean Patent Publication No. 10-2000-0051826 The problem to be solved

[0010] The present invention relates to a novel organic light-emitting material and an organic light-emitting device comprising the same. means of solving the problem

[0012] The present invention provides a compound represented by the following chemical formula 1:

[0013] [Chemical Formula 1]

[0014]

[0015] In the above chemical formula 1,

[0016] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 aryl; or C comprising any one or more selected from the group consisting of substituted or unsubstituted O and S. 2-60 It is heteroaryl, and

[0017] R1 to R8 are each independently hydrogen; deuterium; or substituted or unsubstituted C 6-60 It is an aryl, wherein at least one of R1 to R8 is deuterium, and

[0018] Ra to Rd are each independently hydrogen; deuterium; or unsubstituted or deuterium-substituted C 6-60 It is Aril.

[0020] In addition, the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound represented by Chemical Formula 1. Effects of the invention

[0022] The compound represented by Chemical Formula 1 described above can be used as a material for the organic layer of an organic light-emitting device, and can improve efficiency, low driving voltage, and / or lifespan characteristics in the organic light-emitting device. In particular, the compound represented by Chemical Formula 1 described above can be used as a material for hole injection, hole transport, light emission, electron transport, and / or electron injection. Brief explanation of the drawing

[0024] FIG. 1 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4). FIG. 2 illustrates an example of an organic light-emitting device comprising 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). Specific details for implementing the invention

[0025] The present invention will be described in more detail below to aid in understanding.

[0027] The present invention provides a compound represented by the above chemical formula 1.

[0029] In this specification, or means a bond connected to another substituent.

[0031] In this specification, the term “substituted or unsubstituted” means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thioxy group; aryl thioxy group; alkyl sulfoxy group; aryl sulfoxy group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamine group; aralkylamine group; heteroarylamine group; arylamine group; arylphosphine group; or heteroaryl group comprising one or more of N, O, and S atoms, or substituted or unsubstituted with two or more of the exemplified substituents connected. For example, “substituents connected with two or more substituents” may be a biphenyl group. In other words, the biphenyl group can be an aryl group or can be interpreted as a substituent consisting of two connected phenyl groups. For example, the term "substituted or unsubstituted" refers to "unsubstituted, or deuterium, halogen, C 1-10 Alkyl, C 1-10 Alkoxy, C 6-20 C comprising aryl and one or more heteroatoms among N, O, and S 2-20It may be understood to mean "substituted with one or more substituents selected from the group consisting of heteroaryls, for example, one to five substituents." Additionally, in this specification, the term "substituted with one or more substituents" may be understood to mean, for example, "substituted with one to five substituents" or "substituted with one or two substituents."

[0033] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but it is preferred to have 1 to 40 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.

[0034]

[0036] In the present specification, the oxygen of the ester group may be substituted with a straight-chain, branched-chain, or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a substituent of the following structural formula, but is not limited thereto.

[0037]

[0039] In the present specification, the number of carbon atoms in the imide group is not particularly limited, but it is preferred to have 1 to 25 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.

[0040]

[0042] In this specification, the silyl groups specifically include, but are not limited to, trimethylsilyl groups, triethylsilyl groups, t-butyldimethylsilyl groups, vinyldimethylsilyl groups, propyldimethylsilyl groups, triphenylsilyl groups, diphenylsilyl groups, phenylsilyl groups, etc.

[0044] In this specification, boron groups specifically include trimethylboron groups, triethylboron groups, t-butyldimethylboron groups, triphenylboron groups, phenylboron groups, etc., but are not limited thereto.

[0046] In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0048] In the present specification, the alkyl group may be a straight chain or a branched chain, and while the number of carbon atoms is not particularly limited, it is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of alkyl groups 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, Examples include 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0050] In the present specification, the alkenyl group may be a straight chain or a branched chain, 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 yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited to these.

[0052] In the present specification, the cycloalkyl group is not particularly limited, but it is preferable that it has 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, 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. are used, but are not limited thereto.

[0054] In this specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. As a monocyclic aryl group, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. As a polycyclic aryl group, the aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

[0056] In this specification, the fluorenyl group may be substituted, and two substituents may combine to form a spiro structure. When the fluorenyl group is substituted, It can be the backbone. However, it is not limited to this.

[0058] In the present specification, the heteroaryl group is a heteroaryl group comprising one or more of O, N, Si, and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 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 heteroaryl groups include thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazine, acridyl, pyridazine, pyrazinyl, quinolinyl, quinazolin, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophen, dibenzothiophen, benzofuranyl, phenanthroline, isooxazolyl, thiadiazole, phenothiazinyl, and There are dibenzofuranyl groups, etc., but are not limited to these.

[0060] In this specification, the aryl group among the aralkyl group, ar alkenyl group, alkylaryl group, and arylamine group is the same as the examples of aryl groups described above. In this specification, the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the examples of alkyl groups described above. In this specification, the description regarding the heteroaryl group described above may be applied to the heteroaryl group among the heteroaryl amines. In this specification, the alkenyl group among the ar alkenyl group is the same as the examples of alkenyl groups described above. In this specification, the description regarding the aryl group described above may be applied to the arylene except that it is a divalent group. In this specification, the description regarding the heteroaryl group described above may be applied to the heteroaryl group except that the heteroarylene is a divalent group. In this specification, the description regarding the aryl group or cycloalkyl group described above may be applied except that the hydrocarbon ring is not monovalent and is formed by the combination of two substituents. In this specification, the description of the heteroaryl group described above may apply except that the heteroaryl is not a monovalent group and is formed by the combination of two substituents.

[0062] Preferably, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-20 aryl; or C comprising any one or more selected from the group consisting of substituted or unsubstituted O and S. 2-20 It can be heteroaryl.

[0063] More preferably, Ar1 and Ar2 may each independently be phenyl, biphenyllyl, dibenzofuranyl, or dibenzothiophenyl, and Ar1 and Ar2 may each independently be unsubstituted or substituted with one or more deuterium atoms.

[0065] Preferably, at least one of Ar1 and Ar2 may be an unsubstituted or a phenyl substituted with one or more deuterium atoms.

[0067] R1 to R8 are each independently hydrogen; deuterium; or substituted or unsubstituted C 6-20It is an aryl, and at least one of R1 to R8 may be deuterium.

[0068] More preferably, R1 to R8 are each independently hydrogen, deuterium, or phenyl substituted with five deuterium atoms, and at least one of R1 to R8 may be deuterium.

[0069] More preferably, R1 to R8 are each independently deuterium or phenyl substituted with five deuterium atoms, and at least one of R1 to R8 may be deuterium.

[0071] Preferably, at least four of R1 to R8 may be deuterium. More preferably, at least six of R1 to R8 may be deuterium. Most preferably, at least seven of R1 to R8 may be deuterium.

[0073] Preferably, Ra to Rd are each independently hydrogen; deuterium; or C that is unsubstituted or substituted with deuterium. 6-20 It could be Aril.

[0074] More preferably, Ra to Rd may each independently be hydrogen, deuterium, phenyl, biphenyll, terphenyll, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl, and the phenyl, biphenyll, terphenyll, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl may each independently be unsubstituted or substituted with one or more deuterium.

[0075] More preferably, Ra to Rd may each independently be hydrogen, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl, and the phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl may each independently be unsubstituted or substituted with one or more deuterium atoms.

[0076] More preferably, any one of Ra to Rd is phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl, and said phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl and triphenylenyl may each be independently unsubstituted or substituted with one or more deuterium, and the remainder may be hydrogen.

[0077] Most preferably, any one of Ra to Rd is selected from the group consisting of the following, and the remainder may be hydrogen:

[0078]

[0080] Representative examples of compounds represented by the above chemical formula 1 are as follows:

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0111] The compound represented by the above chemical formula 1 can be prepared by a manufacturing method such as the following reaction formula 1, for example, and the remaining compounds can be prepared in a similar manner.

[0112] [Reaction Equation 1]

[0113]

[0114] In the above reaction formula 1, R1 to R8, Ra to Rd, Ar1 and Ar2 are as defined in the above formula 1, X is a halogen, and preferably X is chloro or bromo.

[0116] The above reaction scheme 1 is an amine substitution reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be modified as known in the art. The above manufacturing method can be further specified in the manufacturing examples to be described later.

[0118] In addition, the present invention provides an organic light-emitting device comprising a compound represented by Chemical Formula 1. For example, the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound represented by Chemical Formula 1.

[0120] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as 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 comprising a hole injection layer, a hole transport layer, an electron blocking layer, an 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.

[0122] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer may include a compound represented by Chemical Formula 1.

[0124] Additionally, the organic layer may include a hole transport layer, a hole injection layer, or a layer that performs hole transport and hole injection simultaneously, and the hole transport layer, the hole injection layer, or the layer that performs hole transport and hole injection simultaneously may include a compound represented by Chemical Formula 1.

[0126] Additionally, 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 a compound represented by Chemical Formula 1.

[0128] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device of a normal type structure 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 of an inverted type structure 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 illustrated in FIGS. 1 and 2.

[0130] FIG. 1 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4). FIG. 2 illustrates an example of an organic light-emitting device comprising 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).

[0131] In such a structure, the compound represented by the above chemical formula 1 may be included in the light-emitting layer.

[0133] The organic light-emitting device according to the present invention may be manufactured using materials and methods known in the art, except that one or more of the organic layers comprise a compound represented by Chemical Formula 1. Additionally, when the organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0135] For example, an 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. At this time, a physical vapor deposition (PVD) method, such as sputtering or electron beam evaporation, can be used to form an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and then forming an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer thereon, and finally depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0137] In addition, the compound represented by Chemical Formula 1 above can be formed as an organic layer by vacuum deposition as well as solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0139] In addition to this method, an organic light-emitting diode can be manufactured by sequentially depositing an organic layer and an anode material from a cathode material onto a substrate (WO 2003 / 012890). However, the manufacturing method is not limited to this.

[0141] For example, the first electrode is a positive electrode and the second electrode is a negative electrode, or the first electrode is a negative electrode and the second electrode is a positive electrode.

[0143] As for the anode material, a material with a large work function is generally preferred so that hole injection into the organic layer can be facilitated. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metal and oxide such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0145] The above-mentioned cathode material is preferably a material with a small work function to facilitate electron injection into an organic layer. Specific examples of the above-mentioned cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0147] The hole injection layer above is a layer that injects holes from an electrode, and as the hole injection material, a compound having the ability to transport holes, having an excellent hole injection effect on the anode, the emissive layer, or the emissive material, preventing the movement of excitons generated in the emissive layer to the electron injection layer or the electron injection material, and also having excellent thin film formation ability is preferred. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile-hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and conductive polymers of polyaniline and polythiophene series, but are not limited to these.

[0149] The hole transport layer described above is a layer that receives holes from the hole injection layer and transports the holes to the emissive layer. As a hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the emissive layer is suitable, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions, but are not limited to these.

[0151] The above electron blocking layer is a layer placed between the hole transport layer and the light-emitting layer to prevent electrons injected from the cathode from moving to the hole transport layer without recombining in the light-emitting layer, and is also referred to as an electron suppression layer or an electron blocking layer. For the electron blocking layer, a material with lower electron affinity than that of the electron transport layer is preferred.

[0153] The above-mentioned luminescent material is a material capable of emitting light in the visible light region by receiving and combining holes and electrons from a hole transport layer and an electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole, and benzimidazole series; polymers of the poly(p-phenylenevinylene) (PPV) series; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0155] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material may include condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0157] Dopant materials include aromatic amine derivatives, styramine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, chrysene, and periplantene having arylamino groups; styramine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, wherein one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamino groups are substituted or unsubstituted. Specifically, styramine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. In addition, metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0159] The hole blocking layer mentioned above is a layer placed between the electron transport layer and the light-emitting layer to prevent holes injected from the anode from recombining in the light-emitting layer and moving to the electron transport layer; it is also referred to as a hole suppression layer or a hole blocking layer. A material with high ionization energy is preferred for the hole blocking layer.

[0161] The electron transport layer described above is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. As an electron transport material, it is a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, and a material with high electron mobility is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes, but are not limited to these. The electron transport layer can be used with any desired cathode material as in the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum layer or a silver layer. Specifically, these are cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum layer or a silver layer.

[0163] The electron injection layer is a layer that injects electrons from an electrode and has the ability to transport electrons, has an excellent electron injection effect from the cathode, an excellent electron injection effect on the emitting layer or emitting material, prevents the movement of excitons generated in the emitting layer to the hole injection layer, and also has excellent thin film formation ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, etc., their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives are included, but are not limited thereto.

[0165] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, Examples include bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, but are not limited to these.

[0167] Meanwhile, in the present invention, the "electron injection and transport layer" is a layer that performs both the role of the electron injection layer and the electron transport layer, and the material performing the role of each layer may be used alone, mixed, or stacked, but is not limited thereto.

[0169] The organic light-emitting device according to the present invention may be a bottom-emission device, a top-emission device, or a double-sided light-emitting device, and in particular may be a bottom-emission device for which relatively high light-emitting efficiency is required.

[0171] In addition, the compound represented by the above chemical formula 1 may be included in organic solar cells or organic transistors in addition to organic light-emitting devices.

[0173] The present invention is described in more detail below to aid in understanding. However, the following examples are merely illustrative of the invention, and the scope of the invention is not limited by the following examples.

[0175] [Preparation Example]

[0176] Preparation Example A: Preparation of Compound A1

[0177]

[0178] 1) Preparation of Compound A1-1

[0179] Under a 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 400 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (95.1 g, 688.2 mmol) was dissolved in 95 ml of water and added, and after sufficient stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (3.4 g, 4.6 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature, separated into organic and water layers, and the organic layer was distilled. This was then dissolved in 830 ml of toluene, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified using toluene and ethyl acetate through a silica column to produce a gray solid compound A1-1 (58.9 g, 71%, MS: [M+H]+ = 362.8).

[0181] 2) Preparation of Compound A1

[0182] Under a nitrogen atmosphere, A1-1 (50 g, 138.2 mmol) and bis(pinacollato)diborone (38.7 g, 165.8 mmol) were added to 750 ml of Diox and stirred and refluxed. Subsequently, potassium acetate (39.9 g, 414.6 mmol) was added and stirred thoroughly, after which palladium dibenzylideneacetone palladium (2.4 g, 4.1 mmol) and tricyclohexylphosphine (2.3 g, 8.3 mmol) were added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was dissolved in 626 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified using chloroform and ethyl acetate through a silica column to produce a yellow solid compound A1 (53.3 g, 85%, MS: [M+H]+ = 454.3).

[0184] Preparation Example B: Preparation of Compound B1

[0185]

[0186] Compound B1 (35.3 g, 73%, MS: [M+H]+ = 530.4) was prepared using the same method as the preparation of Compound A1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine in Preparation Example A was changed to 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0188] Preparation Example C: Preparation of Compound C1

[0189]

[0190] 1) Preparation of Compound C1-1

[0191] Under a nitrogen atmosphere, (4-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 400 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (95.1 g, 688.2 mmol) was dissolved in 95 ml of water and added, and after sufficient stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (3.4 g, 4.6 mmol) was added. After reacting for 6 hours, the mixture was cooled to room temperature, separated into organic and water layers, and the organic layer was distilled. This was then dissolved in 830 ml of toluene, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified using toluene and ethyl acetate through a silica column to produce a gray solid compound C1-1 (66.4 g, 80%, MS: [M+H]+ = 362.8).

[0193] 2) Preparation of Compound C1

[0194] Under a nitrogen atmosphere, C1-1 (40 g, 110.6 mmol) and bis(pinacollato)diborone (30.9 g, 132.7 mmol) were added to 600 ml of Diox and stirred and refluxed. Subsequently, potassium acetate (31.9 g, 331.7 mmol) was added and stirred thoroughly, after which palladium dibenzylideneacetone palladium (1.9 g, 3.3 mmol) and tricyclohexylphosphine (1.9 g, 6.6 mmol) were added. After reacting for 6 hours, the mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was dissolved in 501 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified using chloroform and ethyl acetate through a silica column to produce a gray solid compound C1 (31.6 g, 63%, MS: [M+H]+ = 454.3).

[0196] Preparation Example D: Preparation of Compound D1

[0197]

[0198] Compound D1 (30.5 g, 70%, MS: [M+H]+ = 461.2) was prepared using the same method as the method for preparing compound A1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine in Preparation Example A was changed to 2-chloro-4,6-bis(phenyl-2,3,4,5-d4)-1,3,5-triazine.

[0200] Preparation Example E: Preparation of Compound E1

[0201]

[0202] Compound E1 (35.8 g, 77%, MS: [M+H]+ = 529) was prepared using the same method as the preparation of Compound A1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine in Preparation Example A was changed to 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0204] Preparation Example 1: Preparation of Compound 1

[0205]

[0206] Step 1) Preparation of Compound Sub 1

[0207] Under a nitrogen atmosphere, compound A1 (36 g, 79.4 mmol) and 3-bromo-1,1'-biphenyl (18.5 g, 79.4 mmol) were added to 720 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (32.9 g, 238.2 mmol) dissolved in 33 ml of water was added and stirred thoroughly, after which bis(tritertiary-butylphosphine)palladium (0.8 g, 1.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 1904 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The concentrated compound was purified using chloroform and ethyl acetate through a silica column to prepare a gray solid compound Sub1 (28.9 g, 76%, MS: [M+H]+ = 480.6).

[0209] Step 2) Preparation of Compound 1

[0210] Compound Sub1 (40 g, 83.4 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (14.5 g, 83.4 mmol) were added to 320 ml of dimethylacetamide under a nitrogen atmosphere and stirred and refluxed. Subsequently, tripotassium phosphate (53.1 g, 250.2 mmol) was added and stirred thoroughly. After reacting for 1 hour, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. This was dissolved in 1583 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered, with the filtrate subjected to vacuum distillation. The concentrated compound was purified using chloroform and ethyl acetate via a silica column to produce yellow solid compound 1 (30.1 g, 57%, MS: [M+H]+ = 633.8).

[0212] Preparation Example 2: Preparation of Compound 2

[0213]

[0214] Step 1) Preparation of Compound Sub 2

[0215] Under a nitrogen atmosphere, compound A1 (36 g, 79.4 mmol) and 4-iodo-1,1'-biphenyl (22.2 g, 79.4 mmol) were added to 720 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (32.9 g, 238.2 mmol) dissolved in 33 ml of water was added and stirred thoroughly, after which bis(tritertiary-butylphosphine)palladium (0.8 g, 1.6 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 1904 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. A red solid compound Sub2 (34.7 g, 91%, MS: [M+H]+ = 480.6) was prepared by recrystallizing the concentrated compound with chloroform and ethyl acetate.

[0217] Step 2) Preparation of Compound 2

[0218] Compound Sub2 (40 g, 83.4 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (14.5 g, 83.4 mmol) were added to 320 ml of dimethylacetamide under a nitrogen atmosphere and stirred and refluxed. Subsequently, tripotassium phosphate (53.1 g, 250.2 mmol) was added and stirred thoroughly. After reacting for 1 hour, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. This was dissolved in 1583 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered, with the filtrate subjected to vacuum distillation. The concentrated compound was purified using chloroform and ethyl acetate via a silica column to produce yellow solid compound 2 (41.7 g, 79%, MS: [M+H]+ = 633.8).

[0220] Preparation Example 3: Preparation of Compound 3

[0221]

[0222] Step 1) Preparation of Compound Sub 3

[0223] Under a nitrogen atmosphere, compound A1 (36 g, 79.4 mmol) and 5'-bromo-1,1':3',1''-terphenyl (24.6 g, 79.4 mmol) were added to 720 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (32.9 g, 238.2 mmol) dissolved in 33 ml of water was added and stirred thoroughly, after which bis(tritertiary-butylphosphine)palladium (0.8 g, 1.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 2206 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. A gray solid compound Sub3 (27.4 g, 62%, MS: [M+H]+ = 556.7) was prepared by recrystallizing the concentrated compound with chloroform and ethyl acetate.

[0225] Step 2) Preparation of Compound 3

[0226] Compound Sub3 (40 g, 72 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (12.5 g, 72 mmol) were added to 320 ml of dimethylacetamide under a nitrogen atmosphere and stirred and refluxed. Subsequently, tripotassium phosphate (45.8 g, 216 mmol) was added and stirred thoroughly. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. This was dissolved in 1531 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered, with the filtrate subjected to vacuum distillation. The concentrated compound was purified using chloroform and ethyl acetate via a silica column to produce yellow solid compound 3 (40.8 g, 80%, MS: [M+H]+ = 709.9).

[0228] Preparation Example 4: Preparation of Compound 4

[0229]

[0230] Step 1) Preparation of Compound Sub 4

[0231] Under a nitrogen atmosphere, compound A1 (30 g, 66.2 mmol) and bromobenzene (10.4 g, 66.2 mmol) were added to 300 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (27.4 g, 198.5 mmol) dissolved in 27 ml of water was added and stirred thoroughly, after which bis(tritertiary-butylphosphine)palladium (0.7 g, 1.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 1335 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. A gray solid compound Sub4 (19.5 g, 73%, MS: [M+H]+ = 404.5) was prepared by recrystallizing the concentrated compound with chloroform and ethyl acetate.

[0233] Step 2) Preparation of Compound 4

[0234] Under a nitrogen atmosphere, compound Sub4 (30 g, 74.4 mmol) and 3-(phenyl-2,4,6-d3)-9H-carbazole-1,2,4,5,6,8-d6 (18.8 g, 74.4 mmol) were added to 240 ml of dimethylacetamide and stirred and refluxed. Subsequently, tripotassium phosphate (47.4 g, 223.1 mmol) was added and stirred thoroughly. After reacting for 1 hour, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. This was dissolved in 1418 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered. The filtrate was then distilled under reduced pressure. The concentrated compound was purified using chloroform and ethyl acetate through a silica column to produce a yellow solid compound 4 (32.1 g, 68%, MS: [M+H]+ = 636.8).

[0236] Preparation Example 5: Preparation of Compound 5

[0237]

[0238] Step 1) Preparation of Compound Sub 5

[0239] Compound B1 (30 g, 56.7 mmol) and Bromobenzene (8.9 g, 56.7 mmol) were added to 450 ml of tetrahydrofuran under a nitrogen atmosphere and stirred and refluxed. Subsequently, potassium carbonate (23.5 g, 170 mmol) was dissolved in 23 ml of water and added, and after sufficient stirring, [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.8 g, 1.1 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, separated into organic and water layers, and the organic layer was distilled. This was then dissolved in 272 ml of toluene, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified using toluene and ethyl acetate through a silica column to prepare a gray solid compound Sub 5 (16.6 g, 61%, MS: [M+H]+ = 480.6).

[0241] Step 2) Preparation of Compound 5

[0242] Compound Sub5 (30 g, 62.6 mmol) and 9H-carbazole-d8 (11 g, 62.6 mmol) were added to 240 ml of dimethylacetamide under a nitrogen atmosphere and stirred and refluxed. Subsequently, tripotassium phosphate (39.8 g, 187.7 mmol) was added and stirred thoroughly. After reacting for 1 hour, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. This was dissolved in 1191 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered, with the filtrate subjected to vacuum distillation. The concentrated compound was purified using chloroform and ethyl acetate via a silica column to produce yellow solid compound 5 (20.7 g, 52%, MS: [M+H]+ = 635.8).

[0244] Preparation Example 6: Preparation of Compound 6

[0245]

[0246] Step 1) Preparation of Compound Sub 6

[0247] Under a nitrogen atmosphere, compound C1 (35 g, 77.2 mmol) and 4-iodo-1,1'-biphenyl (21.6 g, 77.2 mmol) were added to 350 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (32 g, 231.6 mmol) dissolved in 32 ml of water was added and stirred thoroughly, after which bis(tritertiary-butylphosphine)palladium (0.8 g, 1.5 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 1851 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The concentrated compound was purified using chloroform and ethyl acetate through a silica column to produce a gray solid compound Sub6 (29.3g, 79%, MS: [M+H]+ = 480.6).

[0249] Step 2) Preparation of Compound 6

[0250] Compound Sub6 (25 g, 52.1 mmol) and 9H-carbazole-d8 (9.1 g, 52.1 mmol) were added to 200 ml of dimethylacetamide under a nitrogen atmosphere and stirred and refluxed. Subsequently, tripotassium phosphate (33.2 g, 156.4 mmol) was added and stirred thoroughly. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. This was dissolved in 993 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered, with the filtrate subjected to vacuum distillation. The concentrated compound was purified using chloroform and ethyl acetate via a silica column to produce yellow solid compound 6 (17.5 g, 53%, MS: [M+H]+ = 635.8).

[0252] Preparation Example 7: Preparation of Compound 7

[0253]

[0254] Compound 7 (29.5 g, 66%, MS: [M+H]+ = 715.9) was prepared using the same method as the preparation of Compound 6, except that 9H-carbazole-d8 in Preparation Example 6 was changed to 3-(phenyl-d5)-9H-carbazole-1,2,4,5,6,7,8-d7.

[0256] Preparation Example 8: Preparation of Compound 8

[0257]

[0258] Step 1) Preparation of Compound F1

[0259] Compound F1 (39.4 g, 75%, MS: [M+H]+ = 544.4) was prepared using the same method as the preparation of Compound A1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine in Preparation Example 1 was changed to 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine.

[0261] Step 2) Preparation of Compound Sub 7

[0262] Under a nitrogen atmosphere, compound F1 (35 g, 64.4 mmol) and 3-bromo-1,1'-biphenyl (15 g, 64.4 mmol) were added to 350 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (26.7 g, 193.2 mmol) dissolved in 27 ml of water was added and stirred thoroughly, after which bis(tritertiary-butylphosphine)palladium (0.7 g, 1.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 1834 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The concentrated compound was purified using chloroform and ethyl acetate through a silica column to produce a gray solid compound sub7 (22.4 g, 61%, MS: [M+H]+ = 570.6).

[0264] Step 3) Preparation of Compound 8

[0265] Compound Sub7 (30 g, 52.7 mmol) and 9H-carbazole-d8 (9.2 g, 52.7 mmol) were added to 240 ml of dimethylacetamide under a nitrogen atmosphere and stirred and refluxed. Subsequently, tripotassium phosphate (33.5 g, 158 mmol) was added and stirred thoroughly. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. This was dissolved in 1142 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered, with the filtrate subjected to vacuum distillation. The concentrated compound was purified using chloroform and ethyl acetate via a silica column to produce yellow solid compound 8 (25.5 g, 67%, MS: [M+H]+ = 723.9).

[0267] Preparation Example 9: Preparation of Compound 9

[0268]

[0269] Compound 9 (34.1 g, 69%, MS: [M+H]+ = 806) was prepared using the same method as the preparation of compound 8, except that 9H-carbazole-d8 in Preparation Example 8 was changed to 3-(phenyl-d5)-9H-carbazole-1,2,4,5,6,7,8-d7.

[0271] Preparation Example 10: Preparation of Compound 10

[0272]

[0273] Step 1) Preparation of Compound G1

[0274] Compound G1 (26.6 g, 52%, MS: [M+H]+ = 560.5) was prepared using the same method as the preparation of Compound A1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine in Preparation Example 1 was changed to 2-chloro-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine.

[0276] Step 2) Preparation of Compound Sub 8

[0277] Compound Sub 8 (26.4 g, 72%, MS: [M+H]+ = 586.7) was prepared using the same method as the preparation of Compound Sub 7, except that Compound F1 was changed to Compound G1 in Preparation Example 8.

[0279] Step 3) Preparation of Compound 10

[0280] Compound Sub 8 (25 g, 42.7 mmol) and 9H-carbazole-d8 (7.5 g, 42.7 mmol) were added to 200 ml of dimethylacetamide under a nitrogen atmosphere and stirred and refluxed. Subsequently, tripotassium phosphate (27.2 g, 128.1 mmol) was added and stirred thoroughly. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. This was dissolved in 949 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered, with the filtrate subjected to vacuum distillation. The concentrated compound was purified using chloroform and ethyl acetate via a silica column to produce a yellow solid compound 10 (25.3 g, 80%, MS: [M+H]+ = 742).

[0282] Preparation Example 11: Preparation of Compound 11

[0283]

[0284] Compound 11 (21.5 g, 70%, MS: [M+H]+ = 634) was prepared using the same method as the preparation of Compound 2, except that 9H-carbazole-d6 was changed to 9H-carbazole-d8 in Preparation Example 2.

[0286] Preparation Example 12: Preparation of Compound 12

[0287]

[0288] Step 1) Preparation of Compound Sub9

[0289] Under a nitrogen atmosphere, compound D1 (35 g, 75.9 mmol) and 4-iodo-1,1'-biphenyl (21.2 g, 75.9 mmol) were added to 350 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (31.5 g, 227.6 mmol) dissolved in 31 ml of water was added and stirred thoroughly, after which bis(tritertiary-butylphosphine)palladium (0.8 g, 1.5 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 1850 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to produce a gray solid compound Sub9 (27g, 73%, MS: [M+H]+= 488).

[0291] Step 2) Preparation of Compound 12

[0292] Compound Sub9 (25 g, 51.3 mmol) and 9H-carbazole-1,2,3,4,5,6,8-d7 (8.9 g, 51.3 mmol) were added to 200 ml of dimethylacetamide under a nitrogen atmosphere and stirred and refluxed. Subsequently, tripotassium phosphate (32.6 g, 153.8 mmol) was added and stirred thoroughly. After reacting for 1 hour, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. This was dissolved in 987 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered. The filtrate was then subjected to vacuum distillation. The concentrated compound was purified using chloroform and ethyl acetate via a silica column to produce the yellow solid compound Compound 12 (17.4 g, 53%, MS: [M+H]+= 642).

[0294] Preparation Example 13: Preparation of Compound 13

[0295]

[0296] Step 1) Preparation of Compound Sub10

[0297] Under a nitrogen atmosphere, compound D1 (35 g, 75.9 mmol) and 3-bromo-1,1'-biphenyl (17.7 g, 75.9 mmol) were added to 350 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (31.5 g, 227.6 mmol) dissolved in 31 ml of water was added and stirred thoroughly, after which bis(tritertiary-butylphosphine)palladium (0.8 g, 1.5 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 1850 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The concentrated compound was purified using chloroform and ethyl acetate through a silica column to produce a gray solid compound Sub10 (29.2 g, 79%, MS: [M+H]+= 488.6).

[0299] Step 2) Preparation of Compound 13

[0300] Under a nitrogen atmosphere, compound Sub10 (25 g, 51.3 mmol) and 4-(phenyl-d5)-9H-carbazole-1,5,6,8-d4 (12.9 g, 51.3 mmol) were added to 200 ml of dimethylacetamide and stirred and refluxed. Subsequently, tripotassium phosphate (32.6 g, 153.8 mmol) was added and stirred thoroughly. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. This was dissolved in 1093 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered. The filtrate was then distilled under reduced pressure. The concentrated compound was purified using chloroform and ethyl acetate through a silica column to prepare a yellow solid compound 13 (23.7 g, 65%, MS: [M+H]+ = 720).

[0302] Preparation Example 14: Preparation of Compound 14

[0303]

[0304] Step 1) Preparation of Compound Sub11

[0305] Under a nitrogen atmosphere, compound E1 (35 g, 66.1 mmol) and bromobenzene (10.4 g, 66.1 mmol) were added to 350 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (27.4 g, 198.3 mmol) dissolved in 27 ml of water was added and stirred thoroughly, after which bis(tritertiary-butylphosphine)palladium (0.7 g, 1.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 1585 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The concentrated compound was purified using chloroform and ethyl acetate through a silica column to produce a gray solid compound Sub11 (25.4 g, 80%, MS: [M+H]+ = 480.6).

[0307] Step 2) Preparation of Compound 14

[0308] Under a nitrogen atmosphere, compound Sub11 (25 g, 52.1 mmol) and 4-(phenyl-d5)-9H-carbazole-2,5,6,8-d4 (13.2 g, 52.1 mmol) were added to 200 ml of dimethylacetamide and stirred and refluxed. Subsequently, tripotassium phosphate (33.2 g, 156.4 mmol) was added and stirred thoroughly. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts. The filtered organic layer was then distilled. This was dissolved in 1099 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered. The filtrate was then distilled under reduced pressure. The concentrated compound was purified using chloroform and ethyl acetate through a silica column to prepare a yellow solid compound 14 (23.1 g, 63%, MS: [M+H]+ = 712).

[0310] [Example]

[0311] Example 1: Preparation of an organic light-emitting diode

[0312] A glass substrate coated with a thin film of Indium Tin Oxide (ITO) to a thickness of 1,400 Å was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. products were used as the detergent, and distilled water that had been filtered twice using a Millerpore Co. filter was used. After cleaning the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned using solvents consisting of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes and then transported to a vacuum deposition machine.

[0313] On the ITO transparent electrode prepared in this way, the following compounds HT-A and PD were thermally vacuum deposited to a thickness of 100 Å in a weight ratio of 95:5, and then only the following compound HT-A was deposited to a thickness of 1150 Å to form a hole transport layer. On the hole transport layer, the following compound HT-B was thermally vacuum deposited to a thickness of 450 Å to form an electron blocking layer. On the electron blocking layer, the previously prepared compound 1 and the following compound GD were vacuum deposited to a thickness of 400 Å in a weight ratio of 85:15 to form an emissive layer. On the emissive layer, the following compound ET-A was vacuum deposited to a thickness of 50 Å to form a hole blocking layer. On the hole blocking layer above, the following compounds ET-B and Liq were thermally vacuum deposited to a thickness of 250 Å in a weight ratio of 2:1, and then Lif and magnesium were vacuum deposited to a thickness of 30 Å in a weight ratio of 1:1 to form an electron transport and injection layer. On the electron injection layer above, magnesium and silver were deposited to a thickness of 160 Å in a weight ratio of 1:4 to form a cathode, thereby manufacturing an organic light-emitting diode.

[0314]

[0315] In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of magnesium and silver was maintained at 2 Å / sec, and the vacuum level during deposition was 2×10 -7 ~ 5*10 -6 An organic light-emitting diode was fabricated by maintaining torr.

[0317] Examples 2 to 12 and Comparative Examples 1 to 9

[0318] Organic light-emitting diodes of Examples 2 to 12 and Comparative Examples 1 to 9 were fabricated using the same method as in Example 1, except that the host material was changed as shown in Table 1 below. In Table 1 below, compounds GH-A, GH-B, GH-C, GH-D, GH-E, GH-F, GH-G, GH-H, and GH-I are as follows. D of the following compound GH-C 14 This means that 14 hydrogen atoms in the compound inside the parentheses have been replaced with deuterium.

[0319]

[0321] [Experimental Example]

[0322] Current was applied to the organic light-emitting diodes prepared in the above examples and comparative examples to measure the voltage, efficiency, and lifetime (T95), and the results are shown in Table 1 below. At this time, the voltage and efficiency were 10 mA / Cm 2 It was measured by applying a current density of . In addition, T95 in Table 1 below has a current density of 20 mA / Cm 2 It refers to the time measured until the initial brightness drops to 95%.

[0324] emissive layer (host) Voltage (V) Efficiency (cd / A) Life (T95, hr) Example 1 Compound 1 4.75 39.7 92 Example 2 Compound 2 4.91 35.1 89 Example 3 Compound 3 4.12 33.0 83 Example 4 Compound 4 4.44 32.9 88 Example 5 Compound 5 4.62 36.5 72 Example 6 Compound 6 4.88 36.1 66 Example 7 Compound 7 4.83 37.1 74 Example 8 Compound 8 4.47 33.3 83 Example 9 Compound 9 5.00 38.4 79 Example 10 Compound 10 4.95 38.1 77 Example 11 Compound 11 4.91 37.3 98 Example 12 Compound 12 4.91 39.6 108 Example 13 Compound 13 4.10 56.2 138 Example 14 Compound 14 4.02 59.6 156 Comparative Example 1 GH-A 5.95 22.1 16 Comparative Example 2 GH-B 6.02 11.2 10 Comparative Example 3 GH-C 5.44 28.2 13 Comparative Example 4 GH-D 5.21 23.1 49 Comparative Example 5 GH-E 5.72 20.0 52 Comparative Example 6 GH-F 5.90 24.1 46 Comparative Example 7 GH-G 5.72 26.0 41 Comparative Example 8 GH-H 5.52 19.6 48 Comparative Example 9 GH-I 5.32 20.8 39

[0326] The compound represented by Chemical Formula 1 has a polycyclic nitrogen-containing heterocyclic substituent acting as an electron donor and a monocyclic nitrogen-containing heterocyclic substituent acting as an electron acceptor bonded to each other at ortho positions, allowing for easy intra-charge transfer.

[0327] In addition, compounds in which a benzene ring acting as an electron donor and a polycyclic nitrogen-containing heterocyclic ring are bonded to each other at the para position exhibit high molecular stability and are advantageous for both hole and electron transport.

[0328] Therefore, as shown in Table 1 above, when the compound of Chemical Formula 1 is used as a host for an organic light-emitting diode, it can be confirmed that low voltage, high efficiency, and long lifespan characteristics are exhibited. Explanation of the symbols

[0330] 1: Substrate 2: Anode 3: Emitting layer 4: Cathode 5: Hole Injection Layer 6: Hole Transport Layer 7: Electron blocking layer 8: Hole blocking layer 9: Electron transport layer 10: Electron injection layer

Claims

Claim 1 Compound represented by the following chemical formula 1: [Chemical Formula 1] In the above Chemical Formula 1, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 aryl; or C comprising any one or more selected from the group consisting of substituted or unsubstituted O and S. 2-60 It is a heteroaryl, and R1 to R8 are each independently hydrogen; deuterium; or substituted or unsubstituted C 6-60 aryl, wherein at least one of R1 to R8 is deuterium, and any one of Ra to Rd is phenyl, biphenyllyl, terphenyllyl, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl, and the phenyl, biphenyllyl, terphenyllyl, naphthyl, anthracenyl, phenanthrenyl, and triphenylenyl are each independently unsubstituted or substituted with one or more deuterium, and the remainder is hydrogen. Claim 2 A compound according to claim 1, wherein Ar1 and Ar2 are each independently phenyl, biphenyllyl, dibenzofuranyl, or dibenzothiophenyl, and said Ar1 and Ar2 are each independently unsubstituted or substituted with one or more deuterium atoms. Claim 3 In claim 1, a compound of phenyl phosphorus in which at least one of Ar1 and Ar2 is unsubstituted or substituted with one or more deuterium atoms. Claim 4 A compound according to claim 1, wherein R1 to R8 are each independently hydrogen, deuterium, or a phenyl substituted with five deuterium atoms, and at least one of R1 to R8 is a deuterium. Claim 5 A compound according to claim 1, wherein at least 4 of R1 to R8 are deuterium. Claim 6 delete Claim 7 delete Claim 8 delete Claim 9 In claim 1, the compound represented by the above chemical formula 1 is any one selected from the group consisting of the following: . Claim 10 An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound according to any one of claims 1 to 5 and 9. Claim 11 An organic light-emitting device, wherein the organic layer is a light-emitting layer in claim 10.

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