Organic compound and organic electroluminescent device comprising same

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device comprising same and, more specifically, to: an organic compound that is excellent in terms of properties such as electron injection and transport ability, luminescence, electrochemical stability, and thermal stability; and an organic electroluminescent device which includes one or more organic layers each containing the organic compound and is thus improved in terms of properties such as luminous efficiency, driving voltage, and lifespan.

Description

Organic compounds and organic electroluminescent devices containing the same

[0001] The present invention relates to a novel organic compound and an organic electroluminescent device containing the same, and more specifically, to an organic compound having excellent characteristics such as electron injection and transport capacity, luminescence capacity, electrical stability, and thermal stability, and an organic electroluminescent device having improved characteristics such as luminescence efficiency, driving voltage, and lifespan by including the same in one or more organic layers.

[0002] In an organic electroluminescent device (hereinafter referred to as an 'organic EL device'), when a voltage is applied between 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 to the ground state. At this time, the material used as the organic layer can be classified according to its function into a light-emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc.

[0003] The light-emitting layer materials of organic EL devices can be classified into blue, green, and red light-emitting materials depending on the light emission color. In addition, yellow and orange light-emitting layer materials are used to realize better natural colors. Furthermore, to increase color purity and light-emitting efficiency through energy transfer, a host / dopant system can be used as the light-emitting material.

[0004] Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, since the development of phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescence, research is being conducted extensively not only on phosphorescent dopants but also on phosphorescent host materials.

[0005] To date, NPB, BCP, and Alq3 are widely known as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives are reported as materials for emissive layers. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, which have advantages in terms of efficiency improvement among emissive layer materials, are used as blue, green, and red phosphorescent dopant materials, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

[0006] However, while conventional organic layer materials offer advantages in terms of luminescence properties, their low glass transition temperatures result in very poor thermal stability, which is unsatisfactory in terms of the lifespan of organic electroluminescent devices. Therefore, the development of high-performance organic layer materials is required.

[0007] The present invention aims to provide a novel organic compound that has a low refractive index, improved electron injection and transport capabilities, and excellent thermal stability, and can be used as an organic layer material for organic electroluminescent devices, specifically as an electron transport layer material or an electron transport auxiliary layer material.

[0008] In addition, the present invention aims to provide an organic electroluminescent device comprising the aforementioned novel organic compound, which has a low driving voltage, high luminous efficiency, and improved lifespan characteristics.

[0009] To achieve the above objective, the present invention provides an organic compound represented by the following chemical formula 1:

[0010]

[0011] (In the above chemical formula 1,

[0012] n1, n2, n3, n4, n5, and n6 are each 0 or 1, provided that n1+n2+n3≥1, and

[0013] A1 is a polyvalent 6- to 10-membered aromatic ring, and

[0014] A2, A3, A5, and A7 are identical or different from each other, and each is independently a phenylene group or a naphthalene group, and

[0015] A4, A6, and A8 are identical or different from each other, and each is independently a phenyl group or a naphthyl group, and

[0016] The phenylene and naphthalene groups of A2, A3, A5, and A7, and the phenyl and naphthyl groups of A4, A6, and A8 are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of cyano groups and -P(=O)(R1)(R2), wherein if there are multiple substituents, they are identical or different from each other.

[0017] R1 and R2 are identical or different from each other, and each independently C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei,

[0018] m is an integer from 0 to 3, and

[0019] L1 is a single bond, or C6~C 60 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclei,

[0020] Ar1 to Ar3 are identical or different from one another, and each independently contains hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxyl group, C1~C 40 alkyl group of, C2~C 40 alkenyl group of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups,

[0021] The arylene group and heteroarylene group of L1 above, and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of Ar1 to Ar3 above are each independently deuterium (D), halogen, cyano group, nitro group, amino group, hydroxyl group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C1~C 40 alkylphosphine oxide group of, C6~C 60 The arylphosphine oxide group and C6~C 60It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, wherein if there are multiple substituents, they are identical or different from each other).

[0022] In addition, the present invention provides an organic electroluminescent device comprising an anode; a cathode; and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises the aforementioned organic compound.

[0023] For example, the organic layer containing the above organic compound may be an electron transport layer, an electron transport auxiliary layer, or both.

[0024] The compound according to the present invention has excellent thermal stability and thus possesses the characteristic of a long lifespan. At the same time, since it has excellent electron transport capacity and luminescence capacity, it can be used as an organic layer material for an organic electroluminescent device. In particular, when the organic compound of the present invention is used as at least one of an electron transport layer material and an electron transport auxiliary layer material, an organic electroluminescent device having superior luminescence performance, low driving voltage, high efficiency, fast mobility, low refractive index, and long lifespan characteristics compared to conventional materials can be manufactured, and furthermore, a full-color display panel with improved performance and lifespan can also be manufactured.

[0025] FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.

[0026] FIG. 2 is a cross-sectional view schematically showing an organic electroluminescent device according to a second embodiment of the present invention.

[0027] FIG. 3 is a schematic cross-sectional view of an organic electroluminescent device according to a third embodiment of the present invention.

[0028] <Explanation of Symbols>

[0029] 100: Anode, 200: Cathode,

[0030] 300: Organic layer, 310: Hole injection layer,

[0031] 320: Hole transport layer, 330: Emitting layer,

[0032] 340: Electron transport layer, 350: Electron injection layer,

[0033] 360: Electron transport auxiliary layer

[0034] The present invention will be described below.

[0035] <New Organic Compounds>

[0036] The organic compound according to the present invention is a structure in which a first triazine moiety and a second triazine moiety are bonded to a phenylene group, which is a linker group, at a meta-position to form an M-type dual triazine structure, wherein an aromatic ring moiety of 18 to 80 members is introduced directly or through a linker group (L1) into either the first triazine moiety or the second triazine moiety, and is represented by Chemical Formula 1. Such a compound has a low refractive index and excellent heat resistance, electron injection and transport capacity, luminescence capacity, and electrochemical stability, and can realize characteristics of an organic electroluminescent device, such as high efficiency, long lifespan, and low driving voltage characteristics of the device.

[0037] Specifically, in the compound represented by Chemical Formula 1 above, the first and second triazine moiety are each 6-member heteroaromatic rings containing three nitrogen (N) members and are electron-withdrawing groups (EWGs) with high electron absorption. By directly introducing these first and second triazine moietyes into the benzene ring at meta-positions relative to each other, the compound of the present invention has an M-type dual triazine structure. That is, the first and second triazine moietyes are introduced into the 1st and 3rd positions of the benzene ring, respectively.

[0038] In addition, an aromatic ring moiety of 18 to 80 members, specifically an aromatic moiety of 18 to 60 members, and more specifically an aromatic moiety of 18 to 40 members, is introduced on one side of either the first or second triazine moiety. The 18 to 80-membered aromatic ring moiety is formed by simply bonding 3 to 4 benzene rings, or by simply bonding 3 to 4 naphthalene rings, or by simply bonding 2 to 3 benzene rings and naphthalene rings, such as a terphenyl group, a quadrphenyl group, a biphenyl-naphthyl group, a naphthyl-biphenyl group, a phenyl-naphthyl-phenyl group, a terphenyl-naphthyl group, a biphenyl-naphthyl-phenyl group, a phenyl-naphthyl-biphenyl group, or a naphthyl-terphenyl group. Accordingly, the compound of the present invention has an 18- to 80-membered aromatic ring moiety introduced on one side of an M-type dual triazine structure, so that compared to a compound without the introduction of the aromatic ring moiety, the refractive index is lowered and the electron mobility is improved, thereby providing superior electron injection and transport properties. Accordingly, when the compound according to the present invention is applied as a material for the electron transport layer or electron transport auxiliary layer of an organic electroluminescent device, electrons can be smoothly transferred from the cathode (or electron injection layer) to the light-emitting layer, and as a result, the driving voltage of the device is lowered, and high efficiency and long lifespan characteristics can be realized.

[0039] In addition, the compound represented by Chemical Formula 1 above may have various substituents (Ar1 to Ar3) introduced into the M-type dual triazine structure. Depending on the type of these substituents (Ar1 to Ar3), the HOMO and LUMO energy levels of the compound can be controlled, allowing for a wide band gap and high carrier transport. Furthermore, the molecular weight of the compound of the present invention is significantly increased by introducing various substituents (e.g., aryl groups, heteroaryl groups, etc.), which raises the glass transition temperature and improves thermal stability and electrochemical stability.

[0040] As described above, the compound represented by Formula 1 of the present invention not only has a low refractive index but also excellent electron injection and transport capabilities, thermal stability, and electrochemical stability, so it can be used as an organic layer material for an organic electroluminescent device, specifically as a light-emitting layer material, an electron transport layer / injection layer material, an electron transport auxiliary layer material, more specifically as an electron transport layer material or an electron transport auxiliary layer material. In addition, the performance and lifespan characteristics of an organic electroluminescent device containing the compound of Formula 1 can be significantly improved, and the performance of a full-color organic light-emitting panel to which such an organic electroluminescent device is applied can also be maximized.

[0041] In the compound represented by the above chemical formula 1, the A1 to A8-containing aromatic ring moiety ( ) is an 18-80-membered aromatic ring moiety formed by simply bonding 3-4 benzene rings, or by simply bonding 3-4 naphthalene rings, or by simply bonding 2-3 benzene rings and naphthalene rings, and has various forms depending on n1 to n6.

[0042] In these A1 to A8-containing aromatic ring moiety, n1, n2, n3, n4, n5, and n6 are each 0 or 1, provided that n1+n2+n3≥1. For example, when n1 is 1 and n2 and n3 are both 0, A1 is a divalent 6- to 10-membered aromatic ring group, specifically a phenylene group (a divalent benzene ring group) or a divalent naphthalene group. For another example, when n1 and n3 are both 0 and n2 is 1, A1 is a trivalent 6- to 10-membered aromatic ring group, specifically a trivalent benzene ring group or a trivalent naphthalene group. As another example, if n1 to n3 are all 1, or if n1 is 0 and n2 and n3 are 1, A1 is a tetravalent 6- to 10-membered aromatic ring, specifically a tetravalent benzene ring or a tetravalent naphthalene group.

[0043] According to these n1, n2, and n3, the organic compound represented by Formula 1 of the present invention may be an organic compound represented by any one of Formulas 2 to 4 below. However, it is not limited thereto.

[0044]

[0045]

[0046]

[0047] In the above chemical formulas 2 to 4,

[0048] n4, n5, n6, m, L1 and Ar1 to Ar3 are each as defined in Chemical Formula 1 above, and

[0049] Rings Cy1 to Cy8 are each present or non-present, and when rings Cy1 to Cy8 are present, rings Cy1 to Cy8 are each six-membered condensed aromatic rings, and

[0050] Multiple S1s are identical or different from each other, and

[0051] S1 is selected from the group consisting of hydrogen, cyano groups and -P(=O)(R1)(R2), and

[0052] R1 and R2 are each as defined in Chemical Formula 1 above.

[0053] Also, in the above A1 to A8-containing aromatic ring moiety, A2, A3, A5 and A7 are identical or different from each other and are each independently a phenylene group or a naphthalene group, and A4, A6 and A8 are identical or different from each other and are each independently a phenyl group or a naphthyl group.

[0054] At this time, the phenylene and naphthalene groups of A2, A3, A5, and A7, and the phenyl and naphthyl groups of A4, A6, and A8 are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of cyano groups and -P(=O)(R1)(R2), and if there are multiple substituents, they are identical or different from each other. According to one example, at least one of the phenylene and naphthalene groups of A2, A3, A5, and A7 and the phenyl and naphthyl groups of A4, A6, and A8 is substituted with one or more substituents selected from the group consisting of cyano groups and -P(=O)(R1)(R2).

[0055] The above R1 and R2 are identical or different from each other, and each independently C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei. Specifically, R1 and R2 are identical or different from each other, and each independently C1~C 12 alkyl group of, C3~C 12 cycloalkyl groups and C6~C 10 It can be selected from the group consisting of aryl groups. More specifically, R1 and R2 may be identical or different from each other and each may independently be a C1 to C6 alkyl group.

[0056] For example, the above The moiety may be a terphenyl group, a quarterphenyl group, a phenyl-terphenyl group, a biphenyl-naphthyl group, a naphthyl-biphenyl group, a phenyl-naphthyl-phenyl group, a terphenyl-naphthyl group, a biphenyl-naphthyl-phenyl group, a phenyl-naphthyl-biphenyl group, or a naphthyl-terphenyl group. In this case, the terphenyl group, quarterphenyl group, phenyl-terphenyl group, biphenyl-naphthyl group, naphthyl-biphenyl group, phenyl-naphthyl-phenyl group, terphenyl-naphthyl group, biphenyl-naphthyl-phenyl group, phenyl-naphthyl-biphenyl group, and naphthyl-terphenyl group are each independently a cyano group (-CN), C1~C40 dialkylphosphine oxide group of, C1~C 60 The diarylphosphine oxide group of (C1~C 40 alkyl of )(C1~C 60 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of aryl)phosphine oxide groups. Here, AB, such as a phenyl-terphenyl group, a biphenyl-naphthyl group, etc., means a substituent B substituted with substituent A, for example, a phenyl-terphenyl group means a terphenyl group substituted with a phenyl group.

[0057] As another example, the above The moiety may be selected from the group consisting of the following moiety Mo-1 to Mo-53, but is not limited thereto.

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067] In the above moiety Mo-1 to Mo-53,

[0068] * is the site that combines with the above chemical formula 1, and

[0069] Multiple S1s are identical or different from each other, and

[0070] S1 is selected from the group consisting of hydrogen, cyano groups and -P(=O)(R1)(R2), and

[0071] R1 and R2 are each as defined in Chemical Formula 1 above.

[0072] According to the aforementioned n1 to n6 and A1 to A8, the organic compound represented by Formula 1 according to the present invention may be an organic compound represented by any one of the following Formulas 5 to 18. However, it is not limited thereto.

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087] In the above chemical formulas 5 to 18,

[0088] m, L1, and Ar1 to Ar3 are each as defined in Chemical Formula 1 above, and

[0089] Multiple S1s are identical or different from each other, and

[0090] S1 is selected from the group consisting of hydrogen, cyano groups and -P(=O)(R1)(R2), and

[0091] R1 and R2 are each as defined in Chemical Formula 1 above.

[0092] In the compound represented by the above chemical formula 1, m is an integer from 0 to 3, and specifically can be 0 or 1.

[0093] Here, when m is 0, it means that L1 is a single link (direct link), whereas when m is an integer from 1 to 3, L1 is a divalent linker, C6~C 60 It is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclei. Specifically, L1 is a single bond, or C6~C 18 It may be an arylene group. Here, multiple L1s may be identical or different from each other.

[0094] At this time, the arylene group and the heteroarylene group of L1 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C1~C 40 alkylphosphine oxide group of, C6~C 60 The arylphosphine oxide group and C6~C 60It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, specifically deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 alkyl group of, C6~C 30 aryl group, heteroaryl group with 5 to 30 nuclei, C1~C 20 alkylphosphine oxide group of, C6~C 30 The arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be identical or different from each other.

[0095] According to one example, the L1 may be a single bond or be selected from the group consisting of a phenylene group, a biphenylene group, a terphenylene group, a naphthalene group, a phenanthrene group, a triphenylene group, a fluorene group, and combinations thereof. Here, the phenylene group, biphenylene group, terphenylene group, naphthalene group, phenanthrene group, triphenylene group, and fluorene group are each deuterium (D), a halogen (e.g., -F, -Cl, -Br, -I, etc.), a cyano group (-CN), and C1~C 12 alkyl group of, C6~C 10 aryl group, heteroaryl group with 5–10 nuclei, C1–C 12 alkylphosphine oxide groups and C6~C 10 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylphosphine oxide groups. Here, multiple L1s may be identical or different from each other.

[0096] According to another example, L1 may be a single linkage or selected from the group consisting of the following linkers L1-1 and L1-2, but is not limited thereto. In this case, multiple L1s may be identical or different from each other.

[0097]

[0098] In the above linkers L1-1 and L1-2,

[0099] * is the site that combines with the above chemical formula 1, and

[0100] a is an integer from 0 to 4, and

[0101] b is an integer from 0 to 6, and

[0102] Multiple Rs are identical or different from each other, and

[0103] R is hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 alkyl group of, C2~C 40 alkenyl group of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C1~C 40 alkylphosphine oxide group of, C6~C 60 The arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamines, specifically hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 alkyl group of, C6~C 30 aryl group, heteroaryl group with 5 to 30 nuclei, C1~C 20 alkylphosphine oxide group of, C6~C30 The arylphosphine oxide group and C6~C 30 It may be selected from the group consisting of arylamines, more specifically hydrogen, deuterium (D), halogens (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzofuran group, dibenzothiophene group, fluorene group, C1-C6 alkylphosphine oxide groups and C6-C 10 It can be selected from the group consisting of alkylphosphine oxide groups.

[0104] In the compound represented by Chemical Formula 1 above, Ar1 to Ar3 are identical or different from each other and each independently hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60Selected from the group consisting of arylamines, specifically each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 alkyl group of, C2~C 20 alkenyl group, C2~C 20 alkynyl group, C3~C 20 cycloalkyl group, heterocycloalkyl group having 3 to 20 nuclei, C6~C 30 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclei.

[0105] At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group of the above Ar1 to Ar3 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C1~C 40 alkylphosphine oxide group of, C6~C 60 The arylphosphine oxide group and C6~C60 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, specifically, each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 alkyl group of, C6~C 30 aryl group of, C2~C 30 heteroaryl group of, C1~C 20 alkylphosphine oxide group of, C6~C 30 The arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, or the substituents may condense with each other to form a condensed ring. If there are multiple substituents, they may be identical or different from each other.

[0106] According to one example, Ar1 to Ar3 are identical or different from each other, and each independently C1 to C 12 alkyl group of, C3~C 18 cycloalkyl group of, C6~C 30 It may be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclei. In this case, the alkyl group, cycloalkyl group, aryl group, and heteroaryl group of Ar1 to Ar3 may each independently be a deuterium, a cyano group, or a C1 to C2 group. 12 alkyl group of, C3~C 18 cycloalkyl group of, C6~C 30 aryl group, heteroaryl group with 5 to 30 nuclei, C1~C 12 alkylphosphine oxide groups and C6~C 30 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylphosphine oxide groups, and in the case where there are multiple substituents, they may be identical or different from each other.

[0107] According to another example, Ar1 is a phenyl group or a biphenyl group, and Ar2 and Ar3 are identical or different from each other and can each be independently selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophen group, a fluorene group, a quinoline group, an isoquinoline group, a 9,9-dimethylfluorene group, and a 9,9-diphenylfluorene group. At this time, the phenyl and biphenyl groups of Ar1 and the phenyl, biphenyl, terphenyl, naphthyl, dibenzofuran, dibenzothiophen, fluorene, quinoline, isoquinoline, 9,9-dimethylfluorene, and 9,9-diphenylfluorene groups of Ar2 and Ar3 are each independently deuterium, cyano group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, cyclohexyl group, phenyl group, naphthyl group, C1-C6 alkylphosphine oxide group and C6-C 10 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylphosphine oxide groups, and in the case where there are multiple substituents, they may be identical or different from each other.

[0108] According to another example, Ar1 is a phenyl group or a biphenyl group, and Ar2 and Ar3 are identical or different from each other and can each be independently selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophen group, a fluorene group, a quinoline group, an isoquinoline group, a 9,9-dimethylfluorene group, and a 9,9-diphenylfluorene group, provided that at least two of Ar1 to Ar3 may be phenyl groups. At this time, the phenyl and biphenyl groups of Ar1 and the phenyl, biphenyl, terphenyl, naphthyl, dibenzofuran, dibenzothiophen, fluorene, quinoline, isoquinoline, 9,9-dimethylfluorene, and 9,9-diphenylfluorene groups of Ar2 and Ar3 are each independently deuterium, cyano group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, cyclohexyl group, phenyl group, naphthyl group, C1-C6 alkylphosphine oxide group and C6-C 10It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylphosphine oxide groups, and in the case where there are multiple substituents, they may be identical or different from each other.

[0109] The compound represented by Formula 1 according to the present invention may be an organic compound represented by any one of Formulas 19 to 46 below, but is not limited thereto.

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138] In the above chemical formulas 19 to 46,

[0139] m, L1, Ar2, and Ar3 are each as defined in the above Chemical Formula 1, and

[0140] Specifically, m can be 0 or 1, and

[0141] L1 can be a single bond or a phenylene group, and

[0142] One of Ar2 and Ar3 is a phenyl group, and the remainder can be selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophen group, a fluorene group, a quinoline group, an isoquinoline group, a 9,9-dimethylfluorene group, and a 9,9-diphenylfluorene group.

[0143] At this time, the phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzofuran group, dibenzothiophen group, fluorene group, quinoline group, isoquinoline, 9,9-dimethylfluorene group, and 9,9-diphenylfluorene group of the above Ar2 and Ar3 are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, cyano group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, cyclohexyl group, phenyl group, and naphthyl group, and if there are multiple substituents, they may be identical or different from each other.

[0144] Multiple S1s are identical or different from each other, and

[0145] S1 and S2 are identical or different from each other and are selected from the group consisting of hydrogen, cyano groups and -P(=O)(R1)(R2), and

[0146] R1 and R2 are each as defined in Chemical Formula 1 above.

[0147] The organic compound represented by the aforementioned chemical formula 1 may be further specified by the following compounds 1 to 228, but is not limited thereto.

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161] In the present invention, "number of nuclei" refers to the number of ring atoms constituting a ring structure, and said nuclei may be carbon and / or one or more heteroatoms selected from the group consisting of N, O, S and Se. For example, the number of nuclei of pyridine refers to 6, including 5 C and 1 N constituting the pyridine ring.

[0162] In the present invention, "alkyl" refers to a monovalent substituent derived from a straight-chain or side-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0163] In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

[0164] In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0165] In the present invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0166] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclei, wherein one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Examples of such heterocycloalkyls include, but are not limited to, morpholine and piperazine. Here, the number of nuclei refers to the number of atoms forming the ring, i.e., the number of ring atoms.

[0167] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, consisting of a single ring or a combination of two or more rings. Additionally, forms in which two or more rings are simply pendent or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0168] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclei. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Additionally, forms in which two or more rings are simply pendent or condensed with each other may be included, and furthermore, forms condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl. Here, the number of nuclei refers to the number of atoms forming the ring, that is, the number of atoms in the ring.

[0169] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' represents an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0170] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

[0171] In the present invention, "alkylsilyl" means a silyl substituted with an alkyl group having 1 to 40 carbon atoms, and includes not only mono- but also di- and tri-alkylsilyls.

[0172] Also, "arylsilyl" means a silyl substituted with an aryl having 5 to 60 carbon atoms, and includes polyarylsilyls such as mono-, as well as di- and tri-arylsilyls.

[0173] In the present invention, "alkylboron group" means a boron group substituted with an alkyl group having 1 to 40 carbon atoms, and "arylboron group" means a boron group substituted with an aryl group having 6 to 60 carbon atoms.

[0174] In the present invention, "alkylphosphinyl group" means a phosphine group substituted with an alkyl group having 1 to 40 carbon atoms, and includes not only mono- but also di-alkylphosphinyl groups.

[0175] In addition, in the present invention, "arylphosphinyl group" refers to a phosphine group substituted with an aryl group having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphinyl groups.

[0176] In the present invention, "arylphosphine oxide group" refers to a phosphine oxide group substituted with an aryl group having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphine oxide groups.

[0177] In the present invention, "arylamine" refers to an amine substituted with an aryl group having 6 to 60 carbon atoms, and includes not only mono- but also di-arylamines.

[0178] In the present invention, "condensed ring" refers to a condensed aliphatic ring having 3 to 40 carbon atoms, a condensed aromatic ring having 6 to 60 carbon atoms, a condensed heteroaliphatic ring having 3 to 60 nuclei, a condensed heteroaromatic ring having 5 to 60 nuclei, C3~C 60 It refers to a spyro ring or a combination thereof. Here, the number of nuclei refers to the number of atoms forming the ring, i.e., the number of ring atoms.

[0179]

[0180] Organic Electroluminescent Device

[0181] Meanwhile, the present invention provides an organic electroluminescent device (hereinafter referred to as an 'organic EL device') comprising an organic compound represented by the aforementioned chemical formula 1.

[0182] Specifically, the organic electroluminescent device according to the present invention comprises, as illustrated in FIGS. 1 to 3, an anode (100), a cathode (200), and one or more organic layers (300) interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises an organic compound represented by the chemical formula 1. At this time, the compound may be used alone or two or more may be used in combination.

[0183] The above-mentioned organic layer (300) may include one or more of a hole injection layer (310), a hole transport layer (320), a light-emitting layer (330), an electron transport assist layer (360), an electron transport layer (340), and an electron injection layer (350), and at least one of the organic layer (300) may include an organic compound represented by the above-mentioned chemical formula 1. Specifically, the organic layer containing the compound of the above-mentioned chemical formula 1 may be at least one of the light-emitting layer (330), the electron transport layer (340), and the electron transport assist layer (360), and specifically, may be at least one of the electron transport layer (340) and the electron transport assist layer (360).

[0184] According to one example, the above-described organic layer comprises a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, and an electron injection layer, and may optionally further comprise an electron transport assisting layer. The electron transport layer comprises an organic compound represented by Chemical Formula 1. In this case, the organic compound represented by Chemical Formula 1 is included in the organic electroluminescent device as an electron transport layer material. In such an organic electroluminescent device, electrons are easily injected from the cathode or electron injection layer to the electron transport layer due to the compound of Chemical Formula 1, and can also move rapidly from the electron transport layer to the emitting layer, resulting in a high coupling force between holes and electrons in the emitting layer. Therefore, the organic electroluminescent device of the present invention has excellent luminous efficiency, power efficiency, brightness, etc. Furthermore, the compound of Chemical Formula 1 has excellent thermal stability and electrochemical stability, which can improve the performance of the organic electroluminescent device.

[0185] The compound of Formula 1 as described above may be used alone or in combination with electron transport layer materials known in the art.

[0186] In the present invention, the electron transport layer material that can be mixed with the compound of Formula 1 includes electron transport materials commonly known in the art. Non-limiting examples of usable electron transport materials include oxazole compounds, isooxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, lithium complexes (e.g., Liq, etc.), and aluminum complexes (e.g., Alq). 3, Examples include tris(8-quinolinolato)-aluminium, etc.), and gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)). These can be used individually or in combination of two or more.

[0187] In the present invention, when the compound of Formula 1 and the electron transport layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art. For example, the mixing ratio of the organic compound of Formula 1 and the known electron transport material may be a weight ratio of 50:50 to 99:1, specifically a weight ratio of 50:50 to 80:20.

[0188] According to another example, the above-described organic layer comprises one or more layers including a hole injection layer, a hole transport layer, an emissive layer, an electron transport assist layer, an electron transport layer, and an electron injection layer, wherein the electron transport assist layer comprises an organic compound represented by Chemical Formula 1. In this case, the compound represented by Chemical Formula 1 is included in the organic electroluminescent device as an electron transport assist layer material. In this case, the compound of Chemical Formula 1 has a high triplet energy. For this reason, when the compound of Chemical Formula 1 is included as an electron transport assist layer material, the efficiency of the organic electroluminescent device can be increased due to the triplet-triplet fusion (TTF) effect. In addition, the compound of Chemical Formula 1 can prevent excitons or holes generated in the emissive layer from diffusing into the electron transport layer adjacent to the emissive layer. Therefore, the number of excitons contributing to light emission within the emissive layer increases, thereby improving the luminous efficiency of the device, and the durability and stability of the device are enhanced, thereby efficiently increasing the lifespan of the device.

[0189] The compound of Formula 1 as described above may be used alone or in combination with electron transport layer auxiliary layer materials known in the art.

[0190] In the present invention, electron transport auxiliary layer materials that can be mixed with the compound of Formula 1 include electron transport materials commonly known in the field, such as oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), and nitrogen-containing heterocyclic derivatives, but are not limited thereto.

[0191] The structure of the organic electroluminescent device of the present invention described above is not particularly limited, but, for example, an anode (100), one or more organic layers (300) and a cathode (200) may be sequentially stacked on a substrate (see FIGS. 1 to 3). In addition, although not shown, the structure may have an insulating layer or an adhesive layer inserted at the interface between the electrode and the organic layer.

[0192] According to one example, the organic electroluminescent device may have a structure in which an anode (100), a hole injection layer (310), a hole transport layer (320), a light-emitting layer (330), an electron transport layer (340), and a cathode (200) are sequentially stacked on a substrate, as shown in FIG. 1. Optionally, as shown in FIG. 2, an electron injection layer (350) may be located between the electron transport layer (340) and the cathode (200). Additionally, an electron transport auxiliary layer (360) may be located between the light-emitting layer (330) and the electron transport layer (340) (see FIG. 3).

[0193] The organic electroluminescent device of the present invention can be manufactured by forming an organic layer and an electrode using materials and methods known in the art, except that at least one of the organic layers (300) [e.g., a light-emitting layer (330), an electron transport layer (340), or an electron transport auxiliary layer (360)] comprises an organic compound represented by the chemical formula 1.

[0194] The above organic layer can be formed by vacuum deposition or solution coating. Examples of the above solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

[0195] The substrates usable in the present invention are not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films, and sheets.

[0196] In addition, examples of anode materials include metals such as vanadium, chromium, copper, zinc, 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; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited thereto.

[0197] Also, examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, or lead, or alloys thereof; and multilayer materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0198] In addition, the hole injection layer, hole transport layer, light-emitting layer, and electron injection layer are not particularly limited, and ordinary materials known in the industry may be used.

[0199]

[0200] The present invention will be described in detail below through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.

[0201] [Preparation Example 1] Synthesis of Compound H-1

[0202]

[0203] 2,4-dichloro-6-phenyl-1,3,5-triazine (2.26 g, 10 mmol), (3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (3.53 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100 °C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound H-1 (3.2 g, yield 64%) was obtained using column chromatography.

[0204] Mass : [(M+H) + ] : 498

[0205]

[0206] [Preparation Example 2] Synthesis of Compound H-2

[0207]

[0208] 2,4-dichloro-6-phenyl-1,3,5-triazine (2.26 g, 10 mmol), (3-(4-(4'-cyano-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (4.54 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100 °C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound H-2 (4.5 g, yield 75%) was obtained using column chromatography.

[0209]

[0210] [Preparation Example 3] Synthesis of Compound H-3

[0211]

[0212] 2,4-dichloro-6-phenyl-1,3,5-triazine (2.26 g, 10 mmol), (3-(4-(3'-cyano-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (4.54 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100 °C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound H-3 (4.1 g, yield 68%) was obtained using column chromatography.

[0213]

[0214] [Preparation Example 4] Synthesis of Compound H-4

[0215]

[0216] 2,4-dichloro-6-phenyl-1,3,5-triazine (2.26 g, 10 mmol), (3-(4-(2'-cyano-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (4.54 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100 °C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound H-4 (3.7 g, yield 61%) was obtained using column chromatography.

[0217]

[0218] [Preparation Example 5] Synthesis of Compound H-5

[0219]

[0220] 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10 mmol), (3-(4-chloro-6-(4'-cyano-[1,1'-biphenyl]-2-yl)-1,3,5-triazin-2-yl)phenyl)boronic acid (4.12 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100 °C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound H-5 (5.3 g, yield 88%) was obtained by column chromatography.

[0221]

[0222] [Preparation Example 6] Synthesis of Compound H-6

[0223]

[0224] 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10 mmol), (3-(4-chloro-6-(3'-cyano-[1,1'-biphenyl]-2-yl)-1,3,5-triazin-2-yl)phenyl)boronic acid (4.12 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100 °C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound H-6 (5.1 g, yield 85%) was obtained by column chromatography.

[0225]

[0226] [Preparation Example 7] Synthesis of Compound H-7

[0227]

[0228] 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10 mmol), (3-(4-chloro-6-(2'-cyano-[1,1'-biphenyl]-2-yl)-1,3,5-triazin-2-yl)phenyl)boronic acid (4.12 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100 °C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound H-7 (4.8 g, yield 80%) was obtained using column chromatography.

[0229]

[0230] [Synthesization Example 1] Synthesis of Compound 3

[0231]

[0232] Compound H-1 (4.98 g, 10 mmol) obtained in Preparation Example 1, [1,1':2',1''-terphenyl]-4-ylboronic acid (2.74 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100 °C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, target compound 3 (5.2 g, yield 75%) was obtained using column chromatography.

[0233] Mass : [(M+H) + ] : 692

[0234]

[0235] [Synthesization Example 2] Synthesis of Compound 6

[0236]

[0237] Compound H-1 (4.98 g, 10 mmol) obtained in Preparation Example 1, [1,1':2',1''-terphenyl]-3-ylboronic acid (2.74 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 6 (5.5 g, yield 79%) was obtained using column chromatography.

[0238] Mass : [(M+H) +] : 692

[0239]

[0240] [Synthesization Example 3] Synthesis of Compound 9

[0241]

[0242] Compound H-1 (4.98 g, 10 mmol) obtained in Preparation Example 1, [1,1':2',1''-terphenyl]-2-ylboronic acid (2.74 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 9 (6.2 g, yield 89%) was obtained using column chromatography.

[0243] Mass : [(M+H) + ] : 692

[0244]

[0245] [Synthesization Example 4] Synthesis of Compound 14

[0246]

[0247] Compound H-1 (4.98 g, 10 mmol) obtained in Preparation Example 1, [1,1':3',1''-terphenyl]-5'-ylboronic acid, Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 14 (5.5 g, yield 79%) was obtained using column chromatography.

[0248] Mass : [(M+H) + ] : 692

[0249]

[0250] [Synthesization Example 5] Synthesis of Compound 21

[0251]

[0252] Compound H-1 (4.98 g, 10 mmol) obtained in Preparation Example 1, [1,1':3',1'':3'',1'''-quaterphenyl]-4-ylboronic acid (3.50 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 21 (6.7 g, yield 88%) was obtained using column chromatography.

[0253] Mass : [(M+H) + ] : 768

[0254]

[0255] [Synthesization Example 6] Synthesis of Compound 27

[0256]

[0257] Compound H-1 (4.98 g, 10 mmol) obtained in Preparation Example 1, [1,1':2',1'':3'',1'''-quaterphenyl]-3'''-ylboronic acid (3.50 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 27 (6.5 g, yield 85%) was obtained using column chromatography.

[0258] Mass : [(M+H) + ] : 768

[0259]

[0260] [Synthesization Example 7] Synthesis of Compound 36

[0261]

[0262] Compound H-1 (4.94 g, 10 mmol) obtained in Preparation Example 1, [1,1':2',1'':3'',1'''-quaterphenyl]-3'''-ylboronic acid (3.50 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 36 (7.3 g, yield 96%) was obtained using column chromatography.

[0263] Mass : [(M+H) + ] : 768

[0264]

[0265] [Synthesization Example 8] Synthesis of Compound 39

[0266]

[0267] Compound H-1 (4.94 g, 10 mmol) obtained in Preparation Example 1, (4''-cyano-[1,1':2',1''-terphenyl]-4-yl)boronic acid (2.99 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 39 (6.5 g, yield 91%) was obtained using column chromatography.

[0268] Mass : [(M+H) + ] : 717

[0269]

[0270] [Synthesization Example 9] Synthesis of Compound 49

[0271]

[0272] Compound H-1 (4.94 g, 10 mmol) obtained in Preparation Example 1, (4-(dimethylphosphoryl)-[1,1':3',1'':4'',1'''-quaterphenyl]-4'''-yl)boronic acid (4.35 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 49 (7.4 g, yield 88%) was obtained using column chromatography.

[0273] Mass : [(M+H) + ] : 844

[0274]

[0275] [Synthesization Example 10] Synthesis of Compound 113

[0276]

[0277] Compound H-1 (4.94 g, 10 mmol) obtained in Preparation Example 1, [1,1':2',1'':2'',1'''-quaterphenyl]-3-ylboronic acid (3.50 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 113 (7.3 g, yield 96%) was obtained using column chromatography.

[0278] Mass : [(M+H) + ] : 768

[0279]

[0280] [Synthesization Example 11] Synthesis of Compound 114

[0281]

[0282] Compound H-1 (4.94 g, 10 mmol) obtained in Preparation Example 1, (6'-phenyl-[1,1':2',1''-terphenyl]-4'-yl)boronic acid (3.50 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 114 (7.1 g, yield 93%) was obtained using column chromatography.

[0283] Mass : [(M+H) + ] : 768

[0284]

[0285] [Synthesization Example 12] Synthesis of Compound 115

[0286]

[0287] Compound H-1 (4.98 g, 10 mmol) obtained in Preparation Example 1, (4'-phenyl-[1,1':2',1''-terphenyl]-3'-yl)boronic acid (3.50 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100 °C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 115 (6.8 g, yield 89%) was obtained using column chromatography.

[0288] Mass : [(M+H) + ] : 768

[0289]

[0290] [Synthesization Example 13] Synthesis of Compound 124

[0291]

[0292] Compound H-1 (4.94 g, 10 mmol) obtained in Preparation Example 1, (5'-phenyl-[1,1':2',1''-terphenyl]-3-yl)boronic acid (3.50 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 124 (6.8 g, yield 89%) was obtained using column chromatography.

[0293] Mass : [(M+H) + ] : 768

[0294]

[0295] [Synthesizing Example 14] Synthesis of Compound 146

[0296]

[0297] Compound H-2 (6.00 g, 10 mmol) obtained in Preparation Example 2, [1,1':3',1''-terphenyl]-5'-ylboronic acid (2.74 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 146 (5.9 g, yield 74%) was obtained using column chromatography.

[0298] Mass : [(M+H) +] : 793

[0299]

[0300] [Synthesization Example 15] Synthesis of Compound 156

[0301]

[0302] Compound H-3 (6.00 g, 10 mmol) obtained in Preparation Example 3, [1,1':3',1''-terphenyl]-2-ylboronic acid (2.74 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 156 (6.2 g, yield 78%) was obtained using column chromatography.

[0303] Mass : [(M+H) + ] : 793

[0304]

[0305] [Synthesization Example 16] Synthesis of Compound 176

[0306]

[0307] Compound H-4 (6.00 g, 10 mmol) obtained in Preparation Example 4, [1,1':3',1''-terphenyl]-4'-ylboronic acid (2.74 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 176 (5.9 g, yield 74%) was obtained using column chromatography.

[0308] Mass : [(M+H) + ] : 793

[0309]

[0310] [Synthesization Example 17] Synthesis of Compound 189

[0311]

[0312] Compound H-5 (6.00 g, 10 mmol) obtained in Preparation Example 5, [1,1':2',1''-terphenyl]-2-ylboronic acid (2.74 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 189 (4.9 g, yield 62%) was obtained using column chromatography.

[0313] Mass : [(M+H) + ] : 793

[0314]

[0315] [Synthesizing Example 18] Synthesis of Compound 207

[0316]

[0317] Compound H-6 (6.00 g, 10 mmol) obtained in Preparation Example 6, [1,1':4',1''-terphenyl]-2'-ylboronic acid (2.74 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 207 (5.3 g, yield 67%) was obtained using column chromatography.

[0318] Mass : [(M+H) + ] : 793

[0319]

[0320] [Synthesization Example 19] Synthesis of Compound 226

[0321]

[0322] Compound H-7 (6.00 g, 10 mmol) obtained in Preparation Example 7, [1,1':3',1''-terphenyl]-5'-ylboronic acid (2.74 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 40 ml of toluene, 10 ml of EtOH, and 10 ml of H2O, and stirred at 100°C for 8 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound 226 (6.8 g, yield 86%) was obtained using column chromatography.

[0323] Mass : [(M+H) + ] : 793

[0324]

[0325] [Example 1] Fabrication of a Blue Organic Electroluminescent Device

[0326] Compound 3 synthesized in Synthesis Example 1 was purified by high-purity sublimation using a commonly known method, and then a blue organic electroluminescent device was fabricated according to the following process.

[0327] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0328] An organic electroluminescent device was fabricated by stacking 98 wt% HI + 2 wt% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / 98 wt% BH + 2 wt% BD (20 nm) / compound 3 (5 nm) / ET + Liq (1:1 weight ratio) (30 nm) / LiF (1 nm) / Al (100 nm) in that order on the ITO transparent electrode prepared as above. The structures of HI, HAT-CN6, EB, BH, BD, ET, and Liq used at this time are as follows.

[0329]

[0330]

[0331] [Examples 2 to 19] Preparation of Blue Organic Electroluminescent Devices

[0332] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that the compounds listed in Table 1 were used instead of Compound 3, which was used as the electron transport auxiliary layer material in Example 1.

[0333]

[0334] [Comparative Examples 1 to 3] Preparation of Blue Organic Electroluminescent Devices

[0335] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that the following compounds HB1, HB2, and HB3 were used respectively instead of Compound 3, which was used as the electron transport auxiliary layer material in Example 1. The structures of HB1, HB2, and HB3 used at this time are as follows.

[0336]

[0337]

[0338] [Evaluation Example 1]

[0339] For the organic electroluminescent devices prepared in Examples 1 to 19 and Comparative Examples 1 to 3, respectively, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm² were measured, and the results are shown in Table 1 below.

[0340] Sample Electron Transport Auxiliary Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 1 34.94546.4 Example 2 64.14526.3 Example 3 94.24527.7 Example 4 144.14547.7 Example 5 214.94547.1 Example 6 274.14526.4 Example 7 364.24546.3 Example 8 394.24526.3 Example 9 494.14547.7 Example 10 1134.14547.7 Example 11 144.94527.1 Example 12 1154.14526.4 Example 13 1244.24546.3 Example 141464.24526.3 Example 151564.14547.7 Example 161764.14547.7 Example 171894.94527.1 Example 182074.24527.7 Example 192264.14547.7 Comparative Example 1 HB15.44545.5 Comparative Example 2 HB25.64545.2 Comparative Example 3 HB35.24535.1

[0341] From Table 1 above, it was confirmed that the organic electroluminescent devices prepared in Examples 1 to 19 each had superior driving voltage, emission peak, and current efficiency compared to the organic electroluminescent devices prepared in Comparative Examples 1 to 3.

[0342]

[0343] [Example 20] Fabrication of a Blue Organic Electroluminescent Device

[0344] Compound 3 synthesized in Synthesis Example 1 was purified by high-purity sublimation using a commonly known method, and then a blue organic electroluminescent device was fabricated according to the following process.

[0345] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0346] An organic electroluminescent device was fabricated by stacking 98 wt% HI + 2 wt% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / 98 wt% BH + 2 wt% BD (20 nm) / HB (5 nm) / compound 3 + Liq (1:1 weight ratio) (30 nm) / LiF (1 nm) / Al (100 nm) in that order on the ITO transparent electrode prepared as above. At this time, the structures of HI, HAT-CN6, EB, BH, BD, HB, and Liq used are as follows.

[0347]

[0348]

[0349] [Examples 21 to 38] Preparation of Blue Organic Electroluminescent Devices

[0350] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 20, except that the compounds listed in Table 2 below were used instead of Compound 3, which was used as the electron transport layer material in Example 20.

[0351]

[0352] [Comparative Examples 4 to 6] Preparation of Blue Organic Electroluminescent Devices

[0353] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 20, except that the following compounds ET1, ET2, and ET3 were used respectively instead of compound 3 used as the electron transport layer material in Example 20. The structures of the compounds ET1, ET2, and ET3 used at this time are as follows.

[0354]

[0355]

[0356] [Evaluation Example 2]

[0357] For the organic electroluminescent devices prepared in Examples 20 to 38 and Comparative Examples 4 to 6, respectively, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm² were measured, and the results are shown in Table 2 below.

[0358] Sample Electron Transport Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 203 4.14547.2 Example 216 4.34596.6 Example 229 4.34576.7 Example 231 44.14527.0 Example 242 14.14527.0 Example 252 74.34596.6 Example 263 64.24576.7 Example 273 94.14527.0 Example 284 94.04517.0 Example 291 134.34527.0 Example 301 144.34527.0 Example 31 154.14596.6 Example 321244.14576.7 Example 331464.14527.0 Example 341564.14527.0 Example 351764.34596.6 Example 361894.24576.7 Example 372074.14527.0 Example 382264.04517.0 Comparative Example 4ET15.24506.2 Comparative Example 5ET25.14526.4 Comparative Example 6ET34.94536.1

[0359] From Table 2 above, it was confirmed that the organic electroluminescent devices prepared in Examples 20 to 38 had superior driving voltage, emission peak, and current efficiency compared to the organic electroluminescent devices prepared in Comparative Examples 4 to 6.

Claims

1. Organic compound represented by the following chemical formula 1: [Chemical Formula 1] (In the above chemical formula 1, n1, n2, n3, n4, n5, and n6 are each 0 or 1, provided that n1+n2+n3≥1, and A1 is a polyvalent 6- to 10-membered aromatic ring, and A2, A3, A5, and A7 are identical or different from each other, and each is independently a phenylene group or a naphthalene group, and A4, A6, and A8 are identical or different from each other, and each is independently a phenyl group or a naphthyl group, and The phenylene and naphthalene groups of A2, A3, A5, and A7, and the phenyl and naphthyl groups of A4, A6, and A8 are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of cyano groups and -P(=O)(R1)(R2), wherein if there are multiple substituents, they are identical or different from each other. R1 and R2 are identical or different from each other, and each independently C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, m is an integer from 0 to 3, and L1 is a single bond, or C6~C 60 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclei, Ar1 to Ar3 are identical or different from one another, and each independently contains hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxyl group, C1~C 40 alkyl group of, C2~C 40 alkenyl group of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, The arylene group and heteroarylene group of L1 above, and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of Ar1 to Ar3 above are each independently deuterium (D), halogen, cyano group, nitro group, amino group, hydroxyl group, C1~C 40 alkyl group of, C2~C 40 alkenyl group of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C1~C 40 alkylphosphine oxide group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, wherein if there are multiple substituents, they are identical or different from each other).

2. In Paragraph 1, An organic compound represented by the above chemical formula 1 is represented by any one of the following chemical formulas 2 to 4: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] (In the above chemical formulas 2 to 4, n4, n5, n6, m, L1, and Ar1 to Ar3 are each as defined in Paragraph 1, and Rings Cy1 to Cy8 are each present or non-present, and when rings Cy1 to Cy8 are present, rings Cy1 to Cy8 are each six-membered condensed aromatic rings, and Multiple S1s are identical or different from each other, and S1 is selected from the group consisting of hydrogen, cyano groups and -P(=O)(R1)(R2), and R1 and R2 are each as defined in Paragraph 1).

3. In Paragraph 1, of the above chemical formula 1 Organic compound, wherein the moiety is selected from the group consisting of the following moiety Mo-1 to Mo-53: (In the above moiety Mo-1 to Mo-53, * is the site that combines with the above chemical formula 1, and Multiple S1s are identical or different from each other, and S1 is selected from the group consisting of hydrogen, cyano groups and -P(=O)(R1)(R2), and R1 and R2 are each as defined in Paragraph 1).

4. In Paragraph 1, An organic compound represented by the above chemical formula 1 is represented by any one of the following chemical formulas 5 to 18: [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] (In the above chemical formulas 5 to 18, m, L1, and Ar1 to Ar3 are each as defined in Paragraph 1, and Multiple S1s are identical or different from each other, and S1 is selected from the group consisting of hydrogen, cyano groups and -P(=O)(R1)(R2), and R1 and R2 are each as defined in Paragraph 1).

5. In Paragraph 1, Multiple L1s are identical or different from each other, and An organic compound in which L1 is a single bond or is selected from the group consisting of the following linker groups L1-1 and L1-2: (In the above linkers L1-1 and L1-2, * is the site that combines with the above chemical formula 1, and a is an integer from 0 to 4, and b is an integer from 0 to 6, and Multiple Rs are identical or different from each other, and R is hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxyl group, C1~C 40 alkyl group of, C2~C 40 alkenyl group of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C1~C 40 alkylphosphine oxide group of, C6~C 60 The arylphosphine oxide group and C6~C 60 (Selected from the group consisting of arylamine groups).

6. In Paragraph 1, Ar1 to Ar3 are identical or different from each other, and each independently C1 to C 12 alkyl group of, C3~C 18 cycloalkyl group of, C6~C 30 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclei, The alkyl groups, cycloalkyl groups, aryl groups, and heteroaryl groups of the above Ar1 to Ar3 are each independently deuterium, cyano groups, C1~C 12 alkyl group of, C3~C 18 cycloalkyl group of, C6~C 30 aryl group, heteroaryl group with 5 to 30 nuclei, C1~C 12 alkylphosphine oxide groups and C6~C 30 An organic compound that is substituted or unsubstituted with one or more substituents selected from the group consisting of arylphosphine oxide groups, wherein, if there are multiple substituents, they are identical or different from each other.

7. In Paragraph 1, Ar1 is a phenyl group or a biphenyl group, and Ar2 and Ar3 are identical or different from each other and are each independently selected from the group consisting of phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzofuran group, dibenzothiophen group, fluorene group, quinoline group, isoquinoline, 9,9-dimethylfluorene group, and 9,9-diphenylfluorene group, and The phenyl and biphenyl groups of Ar1 and the phenyl, biphenyl, terphenyl, naphthyl, dibenzofuran, dibenzothiophen, fluorene, quinoline, isoquinoline, 9,9-dimethylfluorene, and 9,9-diphenylfluorene groups of Ar2 and Ar3 are each independently deuterium, cyano group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, cyclohexyl group, phenyl group, naphthyl group, C1-C6 alkylphosphine oxide group and C6-C 10 An organic compound that is substituted or unsubstituted with one or more substituents selected from the group consisting of arylphosphine oxide groups, wherein, if there are multiple substituents, they are identical or different from each other.

8. In Paragraph 7, An organic compound in which at least two of Ar1 to Ar3 are unsubstituted phenyl groups.

9. In Paragraph 1, An organic compound represented by the above chemical formula 1, wherein the compound is represented by any one of the following chemical formulas 19 to 46: [Chemical Formula 19] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 26] [Chemical Formula 27] [Chemical Formula 28] [Chemical Formula 29] [Chemical Formula 30] [Chemical Formula 31] [Chemical Formula 32] [Chemical Formula 33] [Chemical Formula 34] [Chemical Formula 35] [Chemical Formula 36] [Chemical Formula 37] [Chemical Formula 38] [Chemical Formula 39] [Chemical Formula 40] [Chemical Formula 41] [Chemical Formula 42] [Chemical Formula 43] [Chemical Formula 44] [Chemical Formula 45] [Chemical Formula 46] (In the above chemical formulas 19 to 46, m, L1, Ar2 and Ar3 are each as defined in Paragraph 1, and Multiple S1s are identical or different from each other, and S1 and S2 are identical or different from each other and are each independently selected from the group consisting of hydrogen, cyano group and -P(=O)(R1)(R2), and R1 and R2 are each as defined in Paragraph 1).

10. In Paragraph 1, An organic compound represented by the above chemical formula 1, selected from the group consisting of the following compounds 1 to 228: .

11. Anode; cathode; comprising one or more organic layers interposed between the anode and the cathode, and An organic electroluminescent device comprising at least one of the above one or more organic layers, wherein the organic compound described in any one of claims 1 to 10.

12. In Paragraph 11, An organic electroluminescent device in which the organic layer containing the above organic compound is an electron transport layer or an electron transport auxiliary layer.

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