Novel Compound and Organic Light-Emitting Device Containing the Same

Abstract

The present invention relates to a novel compound represented by the following Chemical Formula 1 and an organic light-emitting device including the compound. JPEG2024523326000036.jpg43170

Description

Technical Field

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

[0002] Cross-reference to related applications This application claims the benefit of priority based on Korean Patent Application No. 10-2022-0057910 filed on May 11, 2022, and Korean Patent Application No. 10-2023-0057176 filed on May 2, 2023, and all the contents disclosed in the documents of the Korean patent applications are incorporated herein by reference.

Background Art

[0003] Generally, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light-emitting devices that utilize the organic light-emitting phenomenon have a wide viewing angle, excellent contrast, and fast response time, are excellent in luminance, driving voltage, and response speed characteristics, and many studies are being conducted.

[0004] An organic light-emitting device generally has a structure including an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer often has a multilayer structure composed of different substances to enhance the efficiency and stability of the organic light-emitting device. For example, it may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between the two electrodes in such a structure of the organic light-emitting device, holes are injected from the anode and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, an exciton is formed, and when this exciton falls back to the ground state again, light is emitted.

[0005] There is a continuous demand for the development of new materials for the organic substances used in such organic light-emitting devices.

Prior Art Documents

Patent Documents

[0006]

Patent Document 1

SUMMARY OF THE INVENTION

PROBLEMS TO BE SOLVED BY THE INVENTION

[0007] The present invention relates to a novel organic light-emitting material and an organic light-emitting device including the same.

MEANS FOR SOLVING THE PROBLEMS

[0008] The present invention provides a compound represented by Chemical Formula 1 below:

CHEMICAL FORMULA

[0009] The present invention also provides an organic light-emitting device including a first electrode; a second electrode provided to face 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 contain the compound represented by Chemical Formula 1.

EFFECTS OF THE INVENTION

[0010] 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 the efficiency, lower the driving voltage, and / or improve the lifetime characteristics in the organic light-emitting device. In particular, the compound represented by Chemical Formula 1 described above can be used as a hole injection, hole transport, light-emitting, electron transport, and / or electron injection material.

Brief Description of the Drawings

[0011]

Fig. 1

Fig. 2

Embodiments for Carrying Out the Invention

[0012] Hereinafter, it will be described in more detail for the understanding of the present invention.

[0013] The present invention provides the compound represented by Chemical Formula 1.

[0014] In this specification,

Chemical Formula

[0015] As used herein, the term "substituted or unsubstituted" means being substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfinyl group; an arylsulfinyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylamine group; an arylphosphine group; or a heteroaryl group containing one or more of N, O, and S atoms, or being substituted or unsubstituted with a group formed by linking two or more of the exemplified substituents. For example, the "substituent formed by linking two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent formed by linking two phenyl groups.

[0016] In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, it may be a substituent having the following structure, but is not limited thereto.

Chemical formula

[0017] In the present specification, the ester group may be substituted with an oxygen of the ester group 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, it may be a substituent having the following structural formula, but is not limited thereto.

Chemical formula

[0018] In this specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, it may be a substituent having the following structure, but is not limited thereto.

Chemical formula

[0019] In this specification, examples of the silyl group specifically include, but are not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc.

[0020] In this specification, examples of the boron group specifically include, but are not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, etc.

[0021] In this specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

[0022] In this 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 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 another embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of the alkyl group include, but are not limited to, 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, 5-methylhexyl, etc.

[0023] In this 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. Specific examples include, but are not limited to, 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.

[0024] In this specification, the cycloalkyl group is not particularly limited, but preferably has 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, 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 included, but not limited thereto.

[0025] 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 aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. As the monocyclic aryl group, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. As the polycyclic aryl group, it may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc., but is not limited thereto.

[0026] In this specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

Chemical formula

[0027] As used herein, a heteroaryl group is a heteroaryl group containing one or more of O, N, Si, and S as heteroatoms, 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 group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidine group, triazine group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinoprazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group, etc., but is not limited thereto.

[0028] In this specification, the aryl groups in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group are as exemplified for the aryl group described above. In this specification, the alkyl groups in the aralkyl group, alkylaryl group, and alkylamine group are as exemplified for the alkyl group described above. In this specification, the heteroaryl in the heteroarylamine is applicable to the description of the heteroaryl group described above. In this specification, the alkenyl group in the aralkenyl group is as exemplified for the alkenyl group described above. In this specification, the arylene is applicable to the description of the aryl group described above, except that it is a divalent group. In this specification, the heteroarylene is applicable to the description of the heteroaryl group described above, except that it is a divalent group. In this specification, the hydrocarbon ring is applicable to the description of the aryl group or cycloalkyl group described above, except that it is not a monovalent group and is formed by bonding two substituents. In this specification, the heteroaryl is applicable to the description of the heteroaryl group described above, except that it is not a monovalent group and is formed by bonding two substituents.

[0029] Preferably, Ar1 and Ar2 are each independently a substituted or unsubstituted C 6-20 aryl; or a C containing any one or more selected from the group consisting of substituted or unsubstituted N, O, and S 2-20 heteroaryl.

[0030] More preferably, Ar1 and Ar2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthrenyl, phenylphenanthrenyl, binaphthyl, chrysenyl, or benzo[c]phenanthrenyl, and the Ar1 and Ar2 are each independently unsubstituted or may be substituted with one or more deuteriums.

[0031] Preferably, Ar1 may be unsubstituted phenyl or phenyl substituted with deuterium; or unsubstituted naphthyl or naphthyl substituted with deuterium. More preferably, Ar1 may be phenyl or naphthyl.

[0032] Preferably, at least one of Ar1 and Ar2 is substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, chrysenyl, or benzo[c]phenanthrenyl, and the substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, chrysenyl, or benzo[c]phenanthrenyl may be unsubstituted or substituted with one or more deuteriums.

[0033] More preferably, at least one of Ar1 and Ar2 is naphthyl, phenylnaphthyl, binaphthyl, phenanthrenyl, phenylphenanthrenyl, chrysenyl, or benzo[c]phenanthrenyl, and the naphthyl, phenylnaphthyl, binaphthyl, phenanthrenyl, phenylphenanthrenyl, chrysenyl, or benzo[c]phenanthrenyl may be unsubstituted or substituted with one or more deuteriums.

[0034] Preferably, at least one of Ar1 and Ar2 may be substituted with deuterium.

[0035] Preferably, at least one of R1 to R7 may be deuterium.

[0036] Preferably, at least one of Ar1 and Ar2 is substituted with deuterium, or at least one of R1 to R7 may be deuterium. More preferably, at least one of Ar1 and Ar2 is substituted with deuterium, and at least one of R1 to R7 may be deuterium. More preferably, at least one of Ar1 and Ar2 is phenyl substituted with deuterium or naphthyl substituted with deuterium; or at least five of R1 to R7 may be deuterium. Most preferably, at least one of Ar1 and Ar2 is phenyl substituted with five deuteriums or naphthyl substituted with seven deuteriums; or R1 and R3 to R5 may be deuterium.

[0037] Preferably, the compound represented by Chemical Formula 1 may have at least five deuteriums substituted therein.

[0038] Typical examples of the compound represented by Chemical Formula 1 are as follows:

Chemical Formula

[0039] In the above compound, a + b + c is an integer from 1 to 19,

Chemical Formula

[0040] In the above compound, a + b + c is an integer from 1 to 21,

Chemical Formula

[0041] In the above group, a + b + c + d is an integer from 1 to 23,

Chemical Formula

[0042] In the above group, a + b + c + d is an integer from 1 to 25, [Chemical formula]

[0043] In the said group, a + b + c is an integer from 1 to 23, [Chemical formula]

[0044] In the said group, a + b + c is an integer from 1 to 25, [Chemical formula]

[0045] In the said group, a + b + c + d + e is an integer from 1 to 27.

[0046] In the said compound, D is deuterium, and a to e are the numbers of deuterium substituted on each substituent.

[0047] The compound represented by Chemical formula 1 can be produced, for example, by a production method such as the following Reaction formula 1, and the other remaining compounds can also be produced similarly. [Chemical formula]

[0048] In Reaction formula 1, R1 to R7, Ar1 and Ar2 are as defined in Chemical formula 1, X is a halogen, and preferably, X is chloro or bromo.

[0049] Reaction formula 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base. The reactor for the Suzuki coupling reaction can be changed as is well known in the art. The said production method can be further specified in the production examples described later.

[0050] The present invention also provides an organic light-emitting device including the compound represented by Chemical Formula 1. As an example, the present invention provides an organic light-emitting device including a first electrode; a second electrode provided to face 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 include the compound represented by Chemical Formula 1.

[0051] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic layers.

[0052] Also, the organic layer may include a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1.

[0053] Also, the organic layer may include a hole transport layer, a hole injection layer, or a layer that simultaneously performs hole transport and hole injection, and the hole transport layer, the hole injection layer, or the layer that simultaneously performs hole transport and hole injection may include the compound represented by Chemical Formula 1.

[0054] Furthermore, 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.

[0055] Also, 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. Note that the organic light-emitting device according to the present invention may be an organic light-emitting device having an inverted structure in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of the organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.

[0056] FIG. 1 is a diagram showing an example of an organic light-emitting device including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. FIG. 2 is a diagram showing an example of an organic light-emitting device including 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, an electron transport and injection layer 8, and a cathode 4. In such a structure, the compound represented by Chemical Formula 1 is included in the light-emitting layer.

[0057] In such a structure, the compound represented by Chemical Formula 1 is included in the light-emitting layer.

[0058] The organic light-emitting device according to the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers contain the compound represented by Chemical Formula 1. Further, when the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

[0059] For example, the organic light-emitting device according to the present invention can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. At this time, a PVD (Physical Vapor Deposition) method such as a sputtering method or an e-beam evaporation method is used to deposit a metal, a metal oxide having conductivity, or an alloy thereof on the 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 thereon, and then a substance that can be used as a cathode is deposited thereon for manufacturing. In addition to such a method, an organic light-emitting device can be made by sequentially depositing an organic layer and an anode material from a cathode material on a substrate.

[0060] In addition, the compound represented by Chemical Formula 1 may be formed in the organic layer not only by vacuum evaporation but also by a solution coating method during the production of the organic light-emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

[0061] In addition to such methods, an organic light-emitting device can be manufactured by sequentially depositing an organic layer and an anode material from a cathode material on a substrate (WO2003 / 012890). However, the manufacturing method is not limited thereto.

[0062] 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.

[0063] As the anode material, a material having a large work function is usually preferable so that hole injection into the organic layer becomes smooth. 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 metals and oxides 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 thereto.

[0064] As the cathode material, a material having a small work function is usually preferable so that electron injection into the organic layer becomes easy. 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; materials having a multilayer structure such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0065] The hole injection layer is a layer that injects holes from the electrode. As the hole injection material, a compound having the ability to transport holes, excellent hole injection effects from the anode and to the light-emitting layer or the light-emitting material, preventing the electrons of the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and excellent in thin film forming 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 the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, and conductive polymers such as polyaniline and polythiophene, but are not limited thereto.

[0066] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light-emitting layer, and having a high mobility with respect to holes is suitable. Specific examples include arylamine-based organic substances, conductive polymers, and block copolymers having both a conjugated part and a non-conjugated part, but are not limited thereto.

[0067] 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 recombining in the light-emitting layer and passing over to the hole transport layer, and is sometimes called an electron suppression layer. For the electron blocking layer, a material having a smaller electron affinity than the electron transport layer is preferred.

[0068] As the luminescent substance, it is a substance that can emit light in the visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a substance with good quantum efficiency for fluorescence and phosphorescence is preferred. Specific examples include 8-hydroxyquinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole, and benzimidazole-based compounds; poly(p-phenylene vinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited thereto.

[0069] The light-emitting layer may contain a host material and a dopant material. Examples of the host material include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of the heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto. Preferably, the compound represented by Chemical Formula 1 above can be used as the host material of the light-emitting layer.

[0070] Preferably, the light-emitting layer may further contain a compound represented by the following Chemical Formula 2: [Chemical Formula] In Chemical Formula 2, A1 to A3 are each independently a substituted or unsubstituted C 6-60 aryl; or a C containing any one or more selected from the group consisting of substituted or unsubstituted N, O, and S 2-60 heteroaryl, L1 to L3 are each independently a single bond; a substituted or unsubstituted C 6-60 arylene; or a C containing any one or more selected from the group consisting of substituted or unsubstituted N, O, and S 2-60It is a heteroarylene.

[0071] Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, examples of the aromatic amine derivative include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periflanthene having an arylamino group. Examples of the styrylamine compound include compounds in which at least one arylvinyl group is substituted for a substituted or unsubstituted arylamine, and the substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but not limited thereto. Examples of the metal complex include iridium complexes, platinum complexes, etc., but not limited thereto.

[0072] The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light-emitting layer. As the electron transport material, a material that can be easily injected with electrons from the cathode and transferred to the light-emitting layer, and has a high mobility with respect to electrons is preferable. Specific examples include Al complex of 8-hydroxyquinoline; complex containing Alq3; organic radical compounds; hydroxyflavone-metal complexes, etc., but not limited thereto. The electron transport layer can be used together with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are normal materials having a low work function followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.

[0073] The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an excellent electron injection effect from the cathode and on the light-emitting layer or light-emitting material, prevents the excitons generated in the light-emitting layer from moving to the hole injection layer, and is preferably a compound with excellent thin film forming ability. Specifically, there are fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but are not limited thereto.

[0074] Examples of the metal complex compound include lithium 8-hydroxyquinolinate, zinc bis(8-hydroxyquinolinate), copper bis(8-hydroxyquinolinate), manganese bis(8-hydroxyquinolinate), aluminum tris(8-hydroxyquinolinate), aluminum tris(2-methyl-8-hydroxyquinolinate), gallium tris(8-hydroxyquinolinate), beryllium bis(10-hydroxybenzo[h]quinolinate), zinc bis(10-hydroxybenzo[h]quinolinate), gallium bis(2-methyl-8-quinolinato)chloride, gallium bis(2-methyl-8-quinolinato)(o-cresolato), aluminum bis(2-methyl-8-quinolinato)(1-naphtholato), gallium bis(2-methyl-8-quinolinato)(2-naphtholato), etc., but are not limited thereto.

[0075] On the other hand, in the present invention, the "electron injection and transport layer" is a layer that performs all the functions of the electron injection layer and the electron transport layer, and the substances that perform the functions of each layer can be used alone, or laminated or mixed, but are not limited thereto.

[0076] The organic light-emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided emission device, and may particularly be a bottom emission device that requires a relatively high luminous efficiency.

[0077] In addition to organic light-emitting devices, the compound represented by Chemical Formula 1 may also be included in organic solar cells or organic transistors.

[0078] Hereinafter, the present invention will be described in more detail for better understanding. However, the following examples are merely illustrative of the present invention, and the content of the present invention is not limited by the following examples.

Examples

[0079] [Production Example] Production Example 1: Synthesis of Compound 1

Chemical Formula

[0080] Under a nitrogen atmosphere, 2-chloro-4-(phenyl-d5)-6-(6-phenylnaphthalen-2-yl)-1,3,5-triazine (15.0 g, 37.6 mmol) and dibenzo[b,d]furan-1-ylboronic acid (8.8 g, 41.4 mmol) were placed in 300 ml of THF, stirred, and refluxed. Thereafter, potassium carbonate (20.8 g, 150.4 mmol) was dissolved in 62 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.2 g, 1.1 mmol) was added. After reacting for 9 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, the organic layer was distilled. This was dissolved in chloroform again, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography and then by sublimation purification to produce 9.0 g of Compound 1. (Yield 45%, MS: [M+H] + =532)

[0081] Production Example 2: Synthesis of Compound 2

Chemical Formula

[0082] In Production Example 1, Compound 2 was produced in the same production method as the production method of Compound 1, except that 2-chloro-4-(phenyl-d5)-6-(6-phenylnaphthalen-2-yl)-1,3,5-triazine was changed to 2-([2,2'-binaphthalene]-6-yl-1',3',4',5',6',7',8'-d7)-4-chloro-6-phenyl-1,3,5-triazine. (MS [M+H] + =584)

[0083] Production Example 3: Synthesis of Compound 3

Chemical Structure

[0084] In Production Example 1, Compound 3 was produced in the same production method as the production method of Compound 1, except that 2-chloro-4-(phenyl-d5)-6-(6-phenylnaphthalen-2-yl)-1,3,5-triazine was changed to 2-chloro-4-(naphthalen-2-yl)-6-(6-phenylnaphthalen-2-yl)-1,3,5-triazine and dibenzofuran-1-ylboronic acid was changed to (dibenzofuran-1-yl-2,4,6,7,8-d5)boronic acid. (MS [M+H] + =582)

[0085] Production Example 4: Synthesis of Compound 4

Chemical Structure

[0086] In Production Example 1, Compound 4 was produced in the same production method as the production method of Compound 1, except that 2-chloro-4-(phenyl-d5)-6-(6-phenylnaphthalen-2-yl)-1,3,5-triazine was changed to 2-([1,2'-binaphthalene]-6'-yl)-4-chloro-6-phenyl-1,3,5-triazine and dibenzofuran-1-ylboronic acid was changed to (dibenzofuran-1-yl-d7)boronic acid. (MS [M+H] + =584)

[0087] Production Example 5: Synthesis of Compound 5

Chemical Formula

[0088] In Production Example 1, Compound 5 was produced by the same production method as that of Compound 1, except that 2-chloro-4-(phenyl-d5)-6-(6-phenylnaphthalen-2-yl)-1,3,5-triazine was changed to 2-chloro-4-(naphthalen-2-yl-d7)-6-(phenanthren-3-yl)-1,3,5-triazine, and dibenzofuran-1-ylboronic acid was changed to (dibenzofuran-1-yl-2,4,6,7,8-d5)boronic acid. (MS [M+H] + =563)

[0089] Production Example 6: Synthesis of Compound 6

Chemical Formula

[0090] Under a nitrogen atmosphere, 2-chloro-4-phenyl-6-(7-phenylphenanthren-2-yl)-1,3,5-triazine (15 g, 33.8 mmol) and dibenzofuran-1-ylboronic acid (7.9 g, 37.2 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (18.7 g, 135.2 mmol) was dissolved in 56 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.1 g, 1 mmol) was added. After reacting for 8 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, washed twice with water, 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 by silica gel column chromatography to produce 11.7 g of Compound 6-a. (Yield 60%, MS: [M+H] + =577)

[0091]

Chem.

[0092] Compound 6-a (10.0 g, 17.4 mmol), PtO2 (1.2 g, 5.2 mmol), and 87 mL of D2O were placed in a shaker tube. The tube was then sealed and heated at 250 °C and 600 psi for 12 hours. After the reaction was completed, chloroform was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography. Then, 5.1 g of Compound 6 was produced by sublimation purification. (Yield 49%, MS: [M+H] + = 602)

[0093] [Example] [Comparative Example 1] A glass substrate with a thin film coating of ITO (Indium Tin Oxide) with a thickness of 1400 Å was placed in distilled water dissolved with a detergent and ultrasonically cleaned. At this time, the product Decon® CON705 of Fischer Co. was used as the detergent, and distilled water that had been secondarily filtered through a 0.22 μm sterilizing filter of Millipore Co. was used as the distilled water. After cleaning the ITO for 30 minutes, ultrasonic cleaning was repeatedly performed twice with distilled water for 10 minutes each. After the distilled water cleaning was completed, ultrasonic cleaning was performed for 10 minutes each with solvents of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. Also, after cleaning the substrate with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.

[0094] On the thus-prepared ITO transparent electrode, the following compound HI-A and compound LG-101 were sequentially thermally vacuum-deposited to a thickness of 800 Å and 50 Å, respectively, to form a hole injection layer. On top of that, the following compound HT-A was vacuum-deposited to a thickness of 800 Å as a hole transport layer, and then the following compound EB-A was thermally vacuum-deposited to a thickness of 600 Å as an electron blocking layer. Compound RH-A was applied as the host of the light-emitting layer, and compound RD-A was applied as the dopant. The host and the dopant were vacuum-deposited to a thickness of 400 Å at a weight ratio of 98:2. Next, the following compound ET-A and compound Liq were thermally vacuum-deposited to a thickness of 360 Å at a weight ratio of 1:1 as an electron transport and injection layer, and then compound Liq was vacuum-deposited to a thickness of 5 Å.

[0095]

Chemical formula

[0096] On top of the electron injection layer, magnesium and silver were sequentially deposited to a thickness of 220 Å at a weight ratio of 10:1, and aluminum was deposited to a thickness of 1000 Å to form a cathode, thereby manufacturing an organic light-emitting device.

[0097] <Examples 1 to 9 and Comparative Examples 2 to 8> In Comparative Example 1, except for changing as shown in Table 1 instead of Compound 1, the organic light-emitting devices of Examples 1 to 9 and Comparative Examples 2 to 8 were manufactured using the same method as in Example 1-1. At this time, when a mixture of two compounds was used as the host, the parentheses indicate the weight ratio between the host compounds. The structures of Compound pRH-1, Compound pRH-2, and Compounds A to F in Table 1 are as follows.

[0098]

Chemical formula

[0099] <Experimental Example> An electric current was applied to the organic light-emitting devices manufactured in Examples 1 to 9 and Comparative Examples 1 to 8, and the voltage, efficiency, and lifespan were measured. The results are shown in Table 1 below. At this time, the voltage and efficiency were measured by applying a current density of 10 mA / cm 2 and the lifespan (LT97) means the time until the initial luminance decreases to 97% at a current density of 20 mA / cm 2 .

[0100]

Table 1

[0101] According to what is disclosed in Table 1, it can be seen that a structure in which a triazine is directly bonded to the 1-position of dibenzofuran substituted only with hydrogen or deuterium has high electron injection and mobility characteristics and exhibits low-voltage characteristics. In particular, when co-applied with a p-type host having excellent hole transport characteristics such as Compound pRH-1 or pRH-2, it was easy to adjust the charge balance in the light-emitting layer. In addition, an aryl group in which at least one benzene ring containing Ar1 or Ar2 is condensed reduces the triplet energy of the substance, and in particular, energy transfer to a red light-emitting dopant becomes easy, showing high-efficiency characteristics. Not only that, when substituted with deuterium as in Chemical Formula 1, not only does the vibrational energy of the substance decrease and the stability of the substance increase, but also the stability of the exciplex formed with the p-type host increases, enabling long-lifespan characteristics to be exhibited.

[0102] From the above results, it was confirmed that when a compound having the structure of Chemical Formula 1 is applied to the light-emitting layer of an organic electroluminescent device, a device having characteristics of low voltage, high efficiency, and long lifespan can be obtained.

Explanation of Symbols

[0103] 1: Substrate 2: Anode 3: Light-emitting layer 4: Cathode 5: Hole injection layer 6: Hole transport layer 7: Electron blocking layer 8: Electron transport and injection layer

Claims

1. A compound represented by the following Chemical Formula 1: 【Chemical Formula 1】 In Chemical Formula 1, Ar １ and Ar ２ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthrenyl, phenylphenanthrenyl, binaphthylyl, chrysenyl, or benzo[c]phenanthrenyl, Ar 1 and Ar 2 are each independently unsubstituted or substituted with one or more deuteriums, At least one of the Ar １ and Ar ２ is naphthyl, phenylnaphthyl, binaphthylyl, phenanthrenyl, phenylphenanthrenyl, chrysenyl, or benzo[c]phenanthrenyl, The naphthyl, phenylnaphthyl, binaphthylyl, phenanthrenyl, phenylphenanthrenyl, chrysenyl, or benzo[c]phenanthrenyl is unsubstituted or substituted with one or more deuteriums, R １ to R ７ are each independently hydrogen or deuterium, At least one of the Ar １ and Ar ２ is substituted with deuterium or at least one of R １ to R ７ is deuterium.

2. At least one of Ar １ and Ar ２ is substituted with deuterium or at least one of R １ to R ７ is deuterium, The compound according to Claim 1.

3. At least one of Ar １ and Ar ２ is phenyl substituted with deuterium or naphthyl substituted with deuterium; or R １~R ７ at least five of which are deuterium, the compound according to claim 1.

4. Ar １ and Ar ２ at least one of which is phenyl substituted with five deuteriums or naphthyl substituted with seven deuteriums; or R １ and R ３ ~R ５ are deuterium, the compound according to claim 1.

5. The compound represented by Chemical Formula 1 has at least five deuteriums substituted. the compound according to claim 1.

6. The compound represented by Chemical Formula 1 is any one selected from the group consisting of: the compound according to claim 1: 【Chemical Formula 2】 In the said compound, a + b + c is an integer from 1 to 19, 【Chemical Formula 3】 In the said compound, a + b + c is an integer from 1 to 21, 【Chemical Formula 4】 In the said group, a + b + c + d is an integer from 1 to 23, 【Chemical Formula 5】 In the said group, a + b + c + d is an integer from 1 to 25, 【Chemical Formula 6】 In the said group, a + b + c is an integer from 1 to 23, 【Chemical Formula 7】 In the said group, a + b + c is an integer from 1 to 25, 【Chemical Formula 8】 In the said group, a + b + c + d + e is an integer from 1 to 27.

7. A first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device including one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound according to any one of claims 1 to 6. An organic light-emitting device (however, excluding an organic light-emitting device containing a compound selected from the following group: 【Chemical Formula 9】 【Chemical Formula 10】 【Chemical Formula 11】 【Chemical Formula 12】 ).

8. The organic layer is a light-emitting layer. The organic light-emitting device according to claim 7.

9. The light-emitting layer further contains a compound represented by the following Chemical Formula 2. The organic light-emitting device according to claim 8: 【Chemical Formula 13】 In the Chemical Formula 2, A １ ~A ３ are each independently a substituted or unsubstituted C ６－６０ aryl; or a C ２－６０ heteroaryl containing any one or more selected from the group consisting of substituted or unsubstituted N, O, and S, L １ ~L ３ are each independently a single bond; a substituted or unsubstituted C ６－６０ arylene; or a C ２－６０ heteroarylene containing any one or more selected from the group consisting of substituted or unsubstituted N, O, and S.

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