Organic compound and organic electroluminescent device using same

Abstract

The present invention relates to a novel compound and an organic electroluminescent device using same, and, more specifically, to: an organic compound having excellent characteristics such as electron injection and transport ability, light emission ability, electrochemical stability and thermal stability; and an organic electroluminescent device in which characteristics such as luminous efficiency, driving voltage and lifetime are improved by comprising same in one or more organic material layers.

Description

Organic compounds and organic electroluminescent devices using 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, 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, excitons are formed, and light is emitted when these excitons fall to the ground state. At this time, the materials used as the organic layer can be classified according to their function into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc.

[0003] Luminous materials can be classified according to their emission color into blue, green, and red luminous materials, and yellow and orange luminous materials for realizing better natural colors. In addition, host / dopant systems can be used as luminous materials to increase color purity and luminescence efficiency through energy transfer.

[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 can be used as an organic layer material for an organic electroluminescent device, specifically as an electron transport layer material, because it has excellent electron injection and transport capabilities, electrochemical stability, and thermal stability.

[0008] To achieve the above-mentioned objectives, the present invention provides an organic compound represented by the following chemical formula 1:

[0009]

[0010] (In the above chemical formula 1,

[0011] R1 to R4 are identical or different from one another, and each independently hydrogen, 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 40cycloalkyl 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, phosphine group, C1~C 40 alkylphosphine 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, or combined with adjacent groups to form a condensed ring,

[0012] x is an integer greater than or equal to 1, and

[0013] L1 is a polyglot aromatic ring of 6 to 60 won, and

[0014] n is an integer from 0 to 4, and

[0015] L2 is a single bond, or C1~C 40 alkylene group of, C6~C 60 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclei,

[0016] a is an integer greater than or equal to 1, and

[0017] A is a cyano group (-CN) or -P(=O)(Ar1)(Ar2), and

[0018] Ar1 and Ar2 are identical or different from each other, and each independently contains hydrogen, 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,

[0019] 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, phosphine group, alkylphosphine group, arylphosphine group, alkylphosphine oxide group, arylphosphine oxide group, arylamine group, and condensation ring of R1 to R4, the aromatic ring group of L1, the alkylene group, arylene group, and heteroarylene group of L2, and the alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, and heteroaryl group of Ar1 and Ar2 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 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 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).

[0020] 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.

[0021] For example, the organic layer containing the above organic compound may be an electron transport layer, an electron transport auxiliary layer, or both.

[0022] The compound of the present invention can be used as an organic layer material for an organic electroluminescent device because it exhibits excellent electron transport and injection capabilities, heat resistance, luminescence, and electrochemical stability. In particular, when the 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, 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.

[0023] The effects according to the present invention are not limited to those exemplified above, and a wider variety of effects are included in this specification.

[0024] FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.

[0025] FIG. 2 is a cross-sectional view schematically showing an organic electroluminescent device according to a second embodiment of the present invention.

[0026] FIG. 3 is a schematic cross-sectional view of an organic electroluminescent device according to a third embodiment of the present invention.

[0027] <Explanation of Symbols>

[0028] 100: Anode, 200: Cathode,

[0029] 300: Organic layer, 310: Hole injection layer,

[0030] 320: Hole transport layer, 330: Emitting layer,

[0031] 340: Electron transport layer, 350: Electron injection layer,

[0032] 360: Electron transport auxiliary layer

[0033] The present invention will be described below.

[0034] <New Organic Compounds>

[0035] The organic compound according to the present invention has a structure comprising: a benzene ring moiety; a first triazine moiety directly bonded to the benzene ring moiety; a second triazine moiety directly bonded to the 3rd position of the benzene ring moiety, which is a meta-position relative to the first triazine moiety; and a cyano group or phosphine oxide group bonded to the 4th position of the benzene ring moiety, which is an ortho-position relative to the second triazine moiety, through a linker group, and is represented by Chemical Formula 1. Such a compound has excellent heat resistance, carrier transport capacity (particularly electron injection and transport capacity), luminescence capacity, electrochemical stability, etc., and can realize characteristics of an organic electroluminescent device, such as high efficiency, long lifespan, and low driving voltage characteristics of the device.

[0036] In the compound represented by Chemical Formula 1 above, the first and second triazine moiety are both six-membered heteroaromatic rings containing three nitrogen atoms and are electron-attracting groups (EWGs) with high electron absorption. By including these first and second triazine moiety, the compound of the present invention has a dual EWG structure. Therefore, the electron transfer characteristics of the organic layer (particularly the electron transport layer) can be maximized in the compound of the present invention, thereby improving the stability and efficiency of the organic electroluminescent device.

[0037] Specifically, the compound of the present invention has a dual EWG structure of first and second triazine moieties, which amplifies the electron-attracting effect, making it easy to control the LUMO energy level to a low level. As such, when the LUMO energy level is low, it can help the electron transport layer (ETL) to operate more effectively for electron injection and transfer, and consequently, the energy barrier between the electron transport layer and the electron injection layer (EIL) or the emitting layer (EML) can be better aligned.

[0038] In addition, the compound of the present invention can further improve electron mobility within the device compared to cases containing other heterocycles by including a dual EWG structure of first and second triazine moieties. This is because the compound of the present invention includes two triazines having strong EWG characteristics, thereby strengthening the electron transport pathway so that free electrons can move rapidly through the LUMO, and can increase the efficiency of the device while reducing the imbalance between electrons and holes.

[0039] In addition, in the compound of the present invention, the first and second triazine moieties possess material-inherent symmetry and a large number of CN bonds with high binding energy, can have strong intermolecular π-π interactions, and are advantageous in terms of electrical stability due to high oxidation stability through low HOMO energy levels. Accordingly, the triazine-based dual EWG structure can reduce degradation and electrical breakdown during device operation, which is advantageous for increasing lifespan. Therefore, the compound of the present invention exhibits superior electrical stability compared to cases containing other heterocycles, thereby enabling the realization of long-life characteristics of the device.

[0040] Furthermore, in the compound of the present invention, the first and second triazine moietys are directly bonded to the benzene ring moiety at a meta-position relative to each other. That is, the second triazine moiety is bonded to position 1 of the benzene ring moiety, which is at a meta-position relative to the first triazine moiety. Thus, the compound of the present invention comprises an M-type dual triazine structure. Here, the M-type dual triazine structure is at a meta-position, and since the electron transfer pathway is not dispersed compared to the ortho-position or para-position, and electrons can be transferred relatively uniformly through the central phenyl ring, the electron transfer pathway may be more efficient. Additionally, the M-type dual triazine structure minimizes interactions between triazines, thereby maintaining the electron-attracting effect of each triazine independently. On the other hand, if the dual triazine structure is ortho-positioned, spatial collisions between triazines may occur, which may reduce electron attraction and structural stability. On the other hand, if the dual triazine structure is in the para-position, the molecule is more likely to have a planar shape, which may lead to excessive pi-pi stacking. Therefore, since the dual triazine structure of the compound of the present invention is in the meta-position, the electron transfer ability can be further enhanced compared to the ortho-position or para-position.

[0041] In addition, the compound represented by Chemical Formula 1 above may have various substituents introduced into the M-type dual triazine structure. Depending on the type of such substituent, 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.

[0042] In addition, the compound of Chemical Formula 1 contains one or more cyano groups or phosphine oxide groups. In this case, the cyano groups and phosphine oxide groups can delocalize the electron distribution. These cyano groups (or phosphine oxide groups) are bonded to a benzene ring moiety through a linker group (e.g., phenylene group, biphenylene group, naphthalene group, etc.). In this case, the cyano group (or phosphine oxide group) is bonded to the 4th position of the benzene ring moiety, which is the ortho-position based on only one of the first and second triazine moietyes (e.g., the second triazine moiety). If the first triazine moiety is bonded to the 1st position of the benzene ring moiety, the second triazine moiety is bonded to the 3rd position of the benzene ring moiety, and the cyano group (or phosphine oxide group) is bonded to the 4th position of the benzene ring moiety through a linker group. In this way, steric hindrance can occur in the structure as the cyano group (or phosphine oxide) is ortho-positionally bonded to the second triazine moiety. As a result, the compound of the present invention induces delocalization of LUMO orbitals, thereby having a LUMO value suitable for an electron transport layer or an electron transport auxiliary layer. Furthermore, the compound of the present invention can induce an increase in triplet energy through maximized steric hindrance. Therefore, when the compound of the present invention is applied to an organic layer of an organic electroluminescent device (particularly an electron transport layer or an electron transport auxiliary layer), excitons are attracted toward the host side of the emitting layer, and consequently, the movement (diffusion) of excitons is blocked, thereby improving the efficiency and lifespan of the device.

[0043] As described above, the compound represented by Formula 1 of the present invention exhibits excellent electron transport capability, thermal stability, electrochemical stability, etc. Accordingly, the compound of the present invention can be used as an organic layer material for an organic electroluminescent device, preferably as a light-emitting layer material (a blue, green and / or red phosphorescent host material), an electron transport layer / injection layer material, a hole transport layer / injection layer material, a light-emitting auxiliary layer material, a lifespan improvement layer material, an electron transport auxiliary layer material, more preferably as an electron transport layer material and an electron transport auxiliary layer material. An organic electroluminescent device comprising such a compound of the present invention can have significantly improved performance and lifespan characteristics, and a full-color organic light-emitting panel to which such an organic electroluminescent device is applied can also have its performance maximized.

[0044] In the compound represented by Formula 1 according to the present invention, the first triazine moiety (R1-R2 containing-triazine moiety) and the second triazine moiety (R3-R4 containing-triazine moiety) are benzene ring moietys which are trivalent linker groups ( They are bonded to each other through ). At this time, the first and second triazine moiety are bonded to the benzene ring moiety at a meta-position relative to each other. Thus, the present invention includes an M-type dual heteroaryl structure. That is, the first and second triazine moiety are bonded to the 1st and 3rd positions of the benzene ring, respectively.

[0045] In these first and second triazine moieties, R1 to R4 are identical or different from one another 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 60aryl 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, phosphine group, C1~C 40 alkylphosphine 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, or combined with adjacent groups (e.g., R1-R2, R3-R4, etc.) to form a condensation ring, specifically each independently hydrogen, deuterium (D), C1~C 20 alkyl group of, C3~C 20 cycloalkyl group, heterocycloalkyl group having 3 to 20 nuclei, C6~C 30The aryl group of the group consisting of and heteroaryl groups having 5 to 30 nuclei may be selected from the group consisting of the aryl group and a heteroaryl group having 5 to 30 nuclei, or may form a condensed ring by combining with an adjacent group (e.g., R1-R2, R3-R4, etc.), and more specifically, each independently of deuterium (D), cyano group (-CN), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenylenyl group, phenanthryl group, fluorenyl group, anthracenyl group, anthryl group, pyrenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, phenoxathienyl group, It can be selected from the group consisting of an indolizinyl group, an indolyl group, a purinyl group, a quinolyl group, a benzothiazole group, a dibenzofuran group, a dibenzothiophen group, a phenanthrolinyl group, and a carbazoleyl group. Here, the condensation ring is C3~C 60 Condensed aliphatic ring (specifically, C3~C 30 (condensation of aliphatic ring), C6~C 60 Condensed aromatic ring (specifically, C6~C 30 condensed aromatic ring), 5- to 60-membered condensed heteroaromatic ring (specifically, 5- to 30-membered condensed heteroaromatic ring), C3~C 60 It may be one or more selected from the group consisting of spiro rings and combinations thereof.

[0046] 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, phosphine group, alkylphosphine group, arylphosphine group, alkylphosphine oxide group, arylphosphine oxide group, arylamine group, and condensation ring of R1 to R4 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 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 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, heteroaryl group with 5–30 nuclei, C6–C 30 The arylphosphine oxide group and C6~C 30It 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.

[0047] In the compound represented by Chemical Formula 1 of the present invention, x is an integer of 1 or more, specifically an integer of 1 to 3.

[0048] Also, L1 is a polyvalent linker group and, depending on the aforementioned x, may be a 6 to 60-membered aromatic ring with 2 or more valence, and specifically, may be a 6 to 60-membered aromatic ring with 2, 3, or 4 valence. Specifically, L1 may be a polyvalent aromatic ring having 6 to 60 carbon atoms, more specifically, a 2 to 4-membered aromatic ring having 6 to 60 carbon atoms.

[0049] According to one example, L1 can be a 2- to 3-valent aromatic ring group having 6 to 30 carbon atoms.

[0050] According to another example, L1 may be selected from the group consisting of a 2-3 valent benzene ring, a 2-3 valent naphthalene ring, a 2-3 valent anthracene ring, a 2-3 valent phenanthrene group, and a 2-3 valent pyrene group.

[0051] At this time, the polyvalent aromatic ring of L1 (specifically, benzene ring, naphthalene ring, anthracene ring, phenanthrene group, pyrene group) is 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 60aryloxy 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 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, heteroaryl group with 5–30 nuclei, 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.

[0052] According to these x and L1, the organic compound represented by Formula 1 of the present invention may be an organic compound represented by any one of Formulas 2 to 5 below, but is not limited thereto.

[0053]

[0054]

[0055]

[0056]

[0057] In the above chemical formulas 2 to 5,

[0058] R1 to R4, n, L2, a, and A are as defined in the above Chemical Formula 1, and

[0059] b1 is an integer from 0 to 4, specifically an integer from 0 to 2, and

[0060] b2 is an integer from 0 to 6, specifically an integer from 0 to 3, and

[0061] b3 is an integer from 0 to 3, specifically an integer of 0 or 1, and

[0062] b4 is an integer from 0 to 5, specifically an integer from 0 to 3, and

[0063] Multiple Rs are identical or different from each other, and

[0064] 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, 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 arylamines, specifically hydrogen, deuterium (D), C1~C 20 alkyl group of, C3~C 20 cycloalkyl group, heterocycloalkyl group having 3 to 20 nuclei, C6~C 30It may be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclei, more specifically a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenylenyl group, phenanthryl group, fluorenyl group, anthracenyl group, anthryl group, pyrenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, phenoxathienyl group, indolizinyl group, indolyl group, purinyl group, quinolyl group, It can be selected from the group consisting of benzothiazole group, dibenzofuran group, dibenzothiophen group, phenanthrolinyl group and carbazoleyl group, and

[0065] In the compound represented by Chemical Formula 1 of the present invention, n may be plural depending on the aforementioned x. If n is plural, the plural n may be identical or different from each other.

[0066] Also, n is an integer from 0 to 4, and specifically, n can be an integer from 0 to 2.

[0067] Here, when n is 0, it means that L2 is a single link (direct link). On the other hand, when n is an integer from 1 to 4, L2 is a divalent linker, and L2 is C1~C 40 alkylene group of, C6~C 60 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclei, specifically C1~C 20 alkylene group of, C6~C 30It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 30 nuclei, and more specifically C1~C 12 alkylene group of, C6~C 18 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclei. Here, a plurality of L2s may be identical or different from each other.

[0068] At this time, the alkylene group, arylene group, and heteroarylene group of L2 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 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 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, heteroaryl group with 5–30 nuclei, C6–C 30 The arylphosphine oxide group and C6~C 30It 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.

[0069] According to one example, the L2 may be a single bond or may be selected from the group consisting of, but not limited to, a methylene group, an ethylene group, a propylene group, a butylene group, a pentalene group, a heptylene group, an octylene group, a phenylene group, a biphenylene group, a terphenylene group, a divalent naphthalene group, a divalent phenanthrene group, a divalent triphenylene group, a divalent fluorene group, a dibenzofuran group, a dibenzothiophene group, and combinations thereof. Here, the methylene group, ethylene group, propylene group, butylene group, pentalene group, heptylene group, octylene group, phenylene group, biphenylene group, terphenylene group, divalent naphthalene group, divalent phenanthrene group, divalent triphenylene group, divalent fluorene group, divalent dibenzofuran group, and dibenzothiophene group are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), C1~C 12 alkyl group of, C6~C 10 The aryl group of, and C2~C 10 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl groups, and if there are multiple substituents, they may be identical or different from each other. Here, multiple L2s may be identical or different from each other.

[0070] According to another example, L2 may be a single linkage, or the following linker L1-1 or L1-2. In this case, multiple L2s may be identical or different from each other.

[0071]

[0072] In the above linkers L1-1 and L1-2,

[0073] * represents the part that forms a bond with Chemical Formula 1, and

[0074] c1 is an integer from 0 to 4, and specifically, may be an integer from 0 to 2, and

[0075] c2 is an integer from 0 to 6, specifically an integer from 0 to 3, and

[0076] Multiple Rs are identical or different from each other, and

[0077] 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, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 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 arylamines, specifically hydrogen, deuterium (D), C1~C 20 alkyl group of, C3~C 20 cycloalkyl group, heterocycloalkyl group having 3 to 20 nuclei, C6~C 30It may be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclei, more specifically a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenylenyl group, phenanthryl group, fluorenyl group, anthracenyl group, anthryl group, pyrenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, phenoxathienyl group, indolizinyl group, indolyl group, purinyl group, quinolyl group, It can be selected from the group consisting of benzothiazole groups, dibenzofuran groups, dibenzothiophen groups, phenanthrolinyl groups, and carbazole groups.

[0078] In the compound represented by Formula 1 of the present invention, a is an integer of 1 or more, specifically an integer from 1 to 7. Such a may be plural according to the aforementioned x. If a is plural, the plural a may be identical or different from each other.

[0079] Depending on these x and a, the substituent A may be one or multiple, and the multiple A may be identical or different from each other.

[0080] A is a cyano group (-CN) or -P (=O) (Ar1) (Ar2). Such substituent A can enhance electron transfer ability. Additionally, substituent A is bonded to the benzene ring through separate linker groups. In this case, substituent A is bonded to the 4th position of the benzene ring, which is the ortho-position relative to the second triazine moiety.

[0081] The above Ar1 and Ar2 are identical or different from each other, and each independently contains hydrogen, C1~C40 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, specifically, each independently hydrogen, C1~C 20 alkyl group of, C3~C 20 cycloalkyl group, heterocycloalkyl group having 3 to 20 nuclei, C6~C 30 Selected from the group consisting of an aryl group and a heteroaryl having 5 to 30 nuclei, more specifically hydrogen, C1~C 12 alkyl group of, C3~C 12 cycloalkyl group, heterocycloalkyl group having 3 to 12 nuclei, C6~C 18 It can be selected from the group consisting of an aryl group and a heteroaryl having 5 to 18 nuclei.

[0082] At this time, the alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, and heteroaryl group of Ar1 and Ar2 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 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 60The arylphosphine oxide group and C6~C 60 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, heteroaryl group with 5–30 nuclei, 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.

[0083] According to one example, the above Ar1 and Ar2 are identical or different from each other and each independently hydrogen, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenylenyl group, phenanthryl group, fluorenyl group, anthracenyl group, anthryl group, pyrenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, phenoxathienyl group, indolizinyl group, indolyl group, purinyl group, quinolyl group, benzothiazole group, It can be selected from the group consisting of dibenzofuran groups, dibenzothiophen groups, phenanthrolinyl groups, and carbazole groups.

[0084] At this time, the methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenylenyl group, phenanthryl group, fluorenyl group, anthracenyl group, anthryl group, pyrenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, phenoxathienyl group, indolizinyl group, indolyl group, purinyl group, quinolyl group, benzothiazole group, dibenzofuran group, dibenzothiophene group of the above Ar1 and Ar2, The phenanthrolinyl group and the carbazoleyl group are each independently deuterium (D), a halogen (e.g., -F, -Cl, -Br, -I, etc.), a cyano group (-CN), a nitro group (-NO2), an amino group (-NH2), a hydroxyl group (-OH), and C1~C 12 alkyl group of, C6~C 18 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 18 nuclei.

[0085] According to the aforementioned x, L1 and A, the organic compound represented by Chemical Formula 1 may be an organic compound represented by any one of the following Chemical Formulas 6 to 13, but is not limited thereto.

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094] In the above chemical formulas 6 to 13,

[0095] R1 to R4, n, L2, a, Ar1 and Ar2 are each as defined in Chemical Formula 1 above, and

[0096] b1, b2, b3, b4, and R are each as defined in the above chemical formulas 2 to 5.

[0097] According to the aforementioned x, L1, L2 and A, the organic compound represented by Chemical Formula 1 may be an organic compound represented by any one of the following Chemical Formulas 14 to 37, but is not limited thereto.

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122] In the above chemical formulas 14 to 37,

[0123] R1 to R4, Ar1 and Ar2 are each as defined in Chemical Formula 1 above, and

[0124] a1 is an integer from 1 to 5, and specifically can be an integer from 1 to 3, and

[0125] a2 is an integer from 1 to 7, specifically an integer from 1 to 3, and

[0126] b1 is an integer from 0 to 4, and specifically can be an integer from 0 to 2, and

[0127] b2 is an integer from 0 to 6, specifically an integer from 0 to 3, and

[0128] b3 is an integer from 0 to 3, specifically 0 or 1, and

[0129] b4 is an integer from 0 to 5, specifically an integer from 0 to 3, and

[0130] c1 is an integer from 0 to 4, and specifically, may be an integer from 0 to 2, and

[0131] c2 is an integer from 0 to 6, specifically an integer from 0 to 3, and

[0132] n1 is an integer from 1 to 4, and specifically can be an integer from 1 to 2, and

[0133] n2 is an integer from 1 to 3, specifically an integer from 1 to 2, and

[0134] n3 and n4 are integers from 0 to 3, respectively, and

[0135] Multiple Rs are identical or different from each other, and

[0136] 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, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 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 arylamines, specifically hydrogen, deuterium (D), C1~C 20 alkyl group of, C3~C 20 cycloalkyl group, heterocycloalkyl group having 3 to 20 nuclei, C6~C 30It may be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclei, more specifically a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenylenyl group, phenanthryl group, fluorenyl group, anthracenyl group, anthryl group, pyrenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, phenoxathienyl group, indolizinyl group, indolyl group, purinyl group, quinolyl group, It can be selected from the group consisting of benzothiazole groups, dibenzofuran groups, dibenzothiophen groups, phenanthrolinyl groups, and carbazole groups.

[0137] The compound represented by Formula 1 according to the present invention described above may be embodied in the following compounds 001 to 172, but is not limited thereto.

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149] In the present invention, "number of nuclei" refers to the number of ring atoms constituting a ring structure, and said nuclei may be carbon or 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.

[0150] 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.

[0151] 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 having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

[0152] 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.

[0153] 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.

[0154] 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.

[0155] 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.

[0156] 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, i.e., the number of ring atoms.

[0157] 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.

[0158] 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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] 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.

[0163] 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.

[0164] 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.

[0165] 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.

[0166] 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 spiro 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.

[0167]

[0168] Organic Electroluminescent Device

[0169] Meanwhile, the present invention provides an organic electroluminescent device (hereinafter referred to as an 'organic EL device') comprising a compound represented by the aforementioned chemical formula 1.

[0170] 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 a 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.

[0171] 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) comprises a compound represented by the above-mentioned chemical formula 1. Specifically, the organic layer comprising the compound of the above-mentioned chemical formula 1 may be at least one of the electron transport layer (340) and the electron transport assist layer (360).

[0172] 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 a 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 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.

[0173] The compound of Formula 1 as described above may be used alone or in combination with electron transport layer materials known in the art.

[0174] In the present invention, electron transport layer materials that can be mixed with the compound of Formula 1 include 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, and aluminum complexes (e.g., Alq3 , Examples include tris(8-quinolinolato)-aluminium), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These can be used individually or in combination of two or more types.

[0175] 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.

[0176] According to another example, the above-described organic layer comprises 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 a 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.

[0177] 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.

[0178] 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.

[0179] 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.

[0180] 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).

[0181] 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 a compound represented by the chemical formula 1.

[0182] 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.

[0183] 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.

[0184] In addition, examples of anode materials 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; 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.

[0185] 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.

[0186] 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.

[0187]

[0188] The present invention will be explained 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.

[0189] [Preparation Example 1] Synthesis of 4'-chloro-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (A01)

[0190]

[0191] 2-(2-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.0g, 47.3mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (10.8g, 47.3mmol), Pd(PPh3)4(1.6g, 1.4 mmol), and K2CO3 19.6g (141.9mmol) was added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4'-chloro-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (15.2g, 34.1mmol, yield 72%).

[0192] Mass : [(M+H) + ] :446

[0193]

[0194] [Preparation Example 2] Synthesis of 4'-chloro-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-carbonitrile (O2)

[0195]

[0196] 2-(2-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.0g, 47.3mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (10.8g, 47.3mmol), Pd(PPh3)4(1.6g, 1.4 mmol), and K2CO3 19.6g (141.9mmol) was added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(4-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (15.8g, 35.5mmol, yield 75%).

[0197] Mass : [(M+H) + ] :446

[0198]

[0199] [Preparation Example 3] Synthesis of 4''-chloro-2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-4-carbonitrile (A03)

[0200]

[0201] 2-(2-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.0g, 47.3mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbonitrile (14.4g, 47.3 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol), and K2CO3 19.6g (141.9mmol) was added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4''-chloro-2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-4-carbonitrile (19.7g, 37.9mmol, yield 80%).

[0202] Mass : [(M+H) + ] :522

[0203]

[0204] [Preparation Example 4] Synthesis of 4''-chloro-2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (A04)

[0205]

[0206] 2-(2-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.0g, 47.3mmol), 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbonitrile (14.4g, 47.3 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol), and K2CO3 19.6g (141.9mmol) was added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4''-chloro-2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (19.7g, 37.9mmol, yield 80%).

[0207] Mass : [(M+H) + ] :522

[0208]

[0209] [Preparation Example 5] Synthesis of 4-(4'-chloro-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-1-naphthonitrile (A05)

[0210]

[0211] 2-(2-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.0g, 47.3mmol), 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-naphthonitrile (16.8g, 47.3mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol), and K2CO3 19.6g (141.9mmol) was added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4-(4'-chloro-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-1-naphthonitrile (20.5g, 36.0mmol, yield 76%).

[0212] Mass : [(M+H) + ] :572

[0213]

[0214] [Preparation Example 6] Synthesis of 4'-(4-chloro-2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (A06)

[0215]

[0216] 2-(2-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.0g, 47.3mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (18.0g, 47.3mmol), Pd(PPh3)4 (1.6g, 1.4mmol), and K2CO3 (19.6g, 141.9mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, water was removed from the extracted organic layer with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 4'-(4-chloro-2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (21.8 g, 36.4 mmol, yield 77%).

[0217] Mass : [(M+H) + ] :598

[0218]

[0219] [Preparation Example 7] Synthesis of 4'-(4-chloro-2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1'-binaphthalene]-4-carbonitrile (A07)

[0220]

[0221] 2-(2-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.0g, 47.3mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-binaphthalene]-4-carbonitrile (19.2g, 47.3mmol), Pd(PPh3)4 (1.6g, 1.4mmol), and K2CO3 (19.6g, 141.9mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water and heated and stirred under reflux for 2 hours. After the reaction was finished, the organic layer was extracted with Methylene Chloride, water was removed from the extracted organic layer with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 4'-(4-chloro-2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1'-binaphthalene]-4-carbonitrile (22.0 g, 35.5 mmol, yield 75%).

[0222] Mass : [(M+H) + ] :622

[0223]

[0224] [Preparation Example 8] Synthesis of (4'-chloro-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)(methyl)phosphinite (A08)

[0225]

[0226] 2-(2-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.0g, 47.3mmol), dimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide (13.3g, 47.3mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol) and K2CO3 (19.6g, 141.9mmol) was added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain (4'-chloro-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)(methyl)phosphinite (16.4g, 34.1mmol, yield 72%).

[0227] Mass : [(M+H) + ] :482

[0228]

[0229] [Preparation Example 9] Synthesis of 4'-chloro-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3,4-dicarbonitrile (A09)

[0230]

[0231] 2-(2-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.0g, 47.3mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phthalonitrile (12.0g, 47.3mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol) and K2CO3 19.6g (141.9mmol) was added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4'-chloro-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3,4-dicarbonitrile (16.2g, 34.5mmol, yield 73%).

[0232] Mass : [(M+H) + ] :471

[0233]

[0234]

[0235] [Preparation Example 10] Synthesis of 4'-(4-chloro-2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4,4''-dicarbonitrile (A10)

[0236]

[0237] 2-(2-bromo-5-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.0g, 47.3mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4,4''-dicarbonitrile (19.2 g, 47.3 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol) and K2CO3 (19.6g, 141.9mmol) was added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4'-(4-chloro-2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4,4''-dicarbonitrile (20.9g, 34.5mmol, yield 71%).

[0238] Mass : [(M+H) + ] :623

[0239]

[0240] [Preparation Example 11] Synthesis of 2,4-diphenyl-6-(2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)-1,3,5-triazine (B01)

[0241]

[0242] Compound A01 (15.0g, 33.7mmol) synthesized in Preparation Example 1, bis(pinacolato)diboron (11.1g, 43.8mmol), Pd(dppf)Cl2 (0.7g, 1.0mmol), X-Phos (1.0g, 2.0mmol), and KOAc (6.6g, 67.4mmol) were added to 200ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed and filtered, the organic layer was concentrated to remove the solvent and purified by column chromatography to obtain 2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbonitrile (13.7 g, 25.6 mmol, yield 76%).

[0243] Mass : [(M+H) + ] :537

[0244]

[0245] [Preparation Example 12] Synthesis of 2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-carbonitrile (B02)

[0246]

[0247] Compound A02 (15.0g, 33.7mmol), bis(pinacolato)diboron (11.1g, 43.8mmol), Pd(dppf)Cl2 (0.7g, 1.0mmol), X-Phos (1.0g, 2.0mmol), and KOAc (6.6g, 67.4mmol) synthesized in Preparation Example 2 were added to 200ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed and filtered, the organic layer was concentrated to remove the solvent and purified by column chromatography to obtain 2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-carbonitrile (13.9 g, 26.0 mmol, yield 77%).

[0248] Mass : [(M+H) + ] :537

[0249]

[0250] [Preparation Example 13] Synthesis of 2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-4''-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':4',1''-terphenyl]-4-carbonitrile (B03)

[0251]

[0252] Compound A03 (20.0g, 38.4mmol), bis(pinacolato)diboron (12.7g, 49.9mmol), Pd(dppf)Cl2 (0.8g, 1.2mmol), X-Phos (1.1g, 2.3mmol), and KOAc (7.5g, 76.8mmol) synthesized in Preparation Example 3 were added to 200ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, the organic layer was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-4''-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':4',1''-terphenyl]-4-carbonitrile (18.3g, 29.9mmol, yield 78%).

[0253] Mass : [(M+H) + ] :614

[0254]

[0255] [Preparation Example 14] Synthesis of 2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-4''-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (B04)

[0256]

[0257] Compound A04 (20.0g, 38.4mmol) synthesized in Preparation Example 4, bis(pinacolato)diboron (12.7g, 49.9mmol), Pd(dppf)Cl2 (0.8g, 1.2mmol), X-Phos (1.1g, 2.3mmol), and KOAc (7.5g, 76.8mmol) were added to 200ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-4''-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (18.1g, 29.6mmol, yield 77%).

[0258] Mass : [(M+H) + ] :614

[0259]

[0260] [Preparation Example 15] Synthesis of 4-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)-1-naphthonitrile (B05)

[0261]

[0262] Compound A05 (20.0g, 35.0mmol) synthesized in Preparation Example 5, bis(pinacolato)diboron (11.6g, 45.5mmol), Pd(dppf)Cl2 (0.8g, 1.1mmol), X-Phos (1.0g, 2.1mmol), and KOAc (6.9g, 70.0mmol) were added to 200ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, the organic layer was filtered, the solvent was removed by concentrating it, and the mixture was purified by column chromatography to obtain 4-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)-1-naphthonitrile (18.1 g, 27.3 mmol, yield 78%).

[0263] Mass : [(M+H) + ] :664

[0264]

[0265] [Preparation Example 16] Synthesis of 4-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)-1-naphthonitrile (B06)

[0266]

[0267] Compound A06 (20.0g, 33.5mmol) synthesized in Preparation Example 6, bis(pinacolato)diboron (11.1g, 43.5mmol), Pd(dppf)Cl2 (0.7g, 1.0mmol), X-Phos (1.0g, 2.0mmol), and KOAc (6.6g, 67.0mmol) were added to 200ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, the mixture was filtered, the organic layer was concentrated to remove the solvent, and purified by column chromatography to obtain 4'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (17.4 g, 24.5 mmol, yield 76%).

[0268] Mass : [(M+H) + ] :714

[0269]

[0270] [Preparation Example 17] Synthesis of 4-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)-1-naphthonitrile (B07)

[0271]

[0272] Compound A07 (20.0g, 32.2mmol) synthesized in Preparation Example 7, bis(pinacolato)diboron (10.6g, 41.9mmol), Pd(dppf)Cl2 (0.7g, 1.0mmol), X-Phos (0.9g, 1.9mmol), and KOAc (6.3g, 64.4mmol) were added to 200ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, the organic layer was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 4-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)-1-naphthonitrile (17.4 g, 24.5 mmol, yield 76%).

[0273] Mass : [(M+H) + ] :714

[0274]

[0275] [Preparation Example 18] Synthesis of (2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)(methyl)phosphinite (B08)

[0276]

[0277] Compound A08 (20.0g, 41.6mmol) synthesized in Preparation Example 8, bis(pinacolato)diboron (13.7g, 54.1mmol), Pd(dppf)Cl2 (0.9g, 1.2mmol), X-Phos (1.2g, 2.5mmol), and KOAc (8.2g, 83.2mmol) were added to 200ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, the organic layer was filtered, the solvent was removed by concentrating it, and the mixture was purified by column chromatography to obtain (2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)(methyl)phosphinite (18.1g, 31.6mmol, yield 76%).

[0278] Mass : [(M+H) + ] :573

[0279]

[0280] [Preparation Example 19] Synthesis of 2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3,4-dicarbonitrile (B09)

[0281]

[0282] Compound A09 (20.0g, 42.6mmol) synthesized in Preparation Example 9, bis(pinacolato)diboron (14.0g, 55.3mmol), Pd(dppf)Cl2 (0.9g, 1.3mmol), X-Phos (1.2g, 2.6mmol), and KOAc (8.4g, 85.1mmol) were added to 200ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, the organic layer was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3,4-dicarbonitrile (17.9 g, 31.9 mmol, yield 75%).

[0283] Mass : [(M+H) + ] :562

[0284]

[0285] [Preparation Example 20] Synthesis of 4'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4,4''-dicarbonitrile (B10)

[0286]

[0287] Compound A10 (20.0g, 32.1mmol) synthesized in Preparation Example 10, bis(pinacolato)diboron (10.6g, 41.8mmol), Pd(dppf)Cl2 (0.7g, 1.0mmol), X-Phos (0.9g, 1.9mmol), and KOAc (6.3g, 64.3mmol) were added to 200ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, the organic layer was filtered, the solvent was removed by concentrating it, and the mixture was purified by column chromatography to obtain 4'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4,4''-dicarbonitrile (17.0 g, 23.8 mmol, yield 74%).

[0288] Mass : [(M+H) + ] :715

[0289]

[0290] [Synthesization Example 1] Synthesis of 2',4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (Compound 001)

[0291]

[0292] Compound B01 (10.0 g, 18.6 mmol) synthesized in Preparation Example 11, 2-chloro-4,6-diphenyl-1,3,5-triazine (5.0 g, 18.6 mmol), Pd(PPh3)4 (0.6 g, 0.6 mmol), and K2CO3 (7.7g, 55.9mmol) was added to 100ml of toluene, 15.0ml of ethanol, and 15.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2',4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (9.5g, 14.7mmol, yield 79%).

[0293] Mass : [(M+H) + ] :643

[0294]

[0295] [Synthesization Example 2] Synthesis of 2',4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-carbonitrile (Compound 002)

[0296]

[0297] Compound B02 (10.0 g, 18.6 mmol) synthesized in Preparation Example 12, 2-chloro-4,6-diphenyl-1,3,5-triazine (5.0 g, 18.6 mmol), Pd(PPh3)4 (0.6 g, 0.6 mmol), and K2CO3 (7.7g, 55.9mmol) was added to 100ml of toluene, 15.0ml of ethanol, and 15.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2',4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-carbonitrile (9.3g, 14.5mmol, yield 78%).

[0298] Mass : [(M+H) + ] :643

[0299]

[0300] [Synthesization Example 3] Synthesis of 2'',4''-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-4-carbonitrile (Compound 003)

[0301]

[0302] Compound B03 (10.0 g, 16.3 mmol) synthesized in Preparation Example 13, 2-chloro-4,6-diphenyl-1,3,5-triazine (4.4 g, 16.3 mmol), Pd(PPh3)4 (0.6 g, 0.5 mmol), and K2CO3 (6.8g, 49.0mmol) was added to 100ml of toluene, 15.0ml of ethanol, and 15.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2'',4''-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-4-carbonitrile (9.4g, 13.1mmol, yield 80%).

[0303] Mass : [(M+H) + ] :719

[0304]

[0305] [Synthesization Example 4] Synthesis of 2'',4''-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 009)

[0306]

[0307] Compound B04 (10.0 g, 16.3 mmol) synthesized in Preparation Example 14, 2-chloro-4,6-diphenyl-1,3,5-triazine (4.4 g, 16.3 mmol), Pd(PPh3)4 (0.6 g, 0.5 mmol), and K2CO3 (6.8g, 49.0mmol) was added to 100ml of toluene, 15.0ml of ethanol, and 15.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2'',4''-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (9.5g, 13.2mmol, yield 81%).

[0308] Mass : [(M+H) + ] :719

[0309]

[0310] [Synthesization Example 5] Synthesis of 4-(2',4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-1-naphthonitrile (Compound 011)

[0311]

[0312] Compound B05 (10.0 g, 15.1 mmol) synthesized in Preparation Example 15, 2-chloro-4,6-diphenyl-1,3,5-triazine (4.0 g, 15.1 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), and K2CO3 6.3g (45.3mmol) was added to 100ml of toluene, 15.0ml of ethanol, and 15.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4-(2',4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-1-naphthonitrile (9.0g, 11.8mmol, yield 78%).

[0313] Mass : [(M+H) + ] :769

[0314]

[0315] [Synthesization Example 6] Synthesis of 4-(2',4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-1-naphthonitrile (Compound 031)

[0316]

[0317] Compound B06 (10.0 g, 15.1 mmol) synthesized in Preparation Example 16, 2-chloro-4,6-diphenyl-1,3,5-triazine (4.0 g, 15.1 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), and K2CO3 6.3g (45.3mmol) was added to 100ml of toluene, 15.0ml of ethanol, and 15.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4-(2',4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-1-naphthonitrile (8.9g, 11.6mmol, yield 77%).

[0318] Mass : [(M+H) + ] :769

[0319]

[0320] [Synthesization Example 7] Synthesis of 4'-(2,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1'-binaphthalene]-4-carbonitrile (Compound 047)

[0321]

[0322] Compound B07 (10.0 g, 14.0 mmol) synthesized in Preparation Example 17, 2-chloro-4,6-diphenyl-1,3,5-triazine (3.8 g, 18.6 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol), and K2CO3 5.8g (42.1mmol) was added to 100ml of toluene, 15.0ml of ethanol, and 15.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4'-(2,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1'-binaphthalene]-4-carbonitrile (9.0g, 10.9mmol, yield 78%).

[0323] Mass : [(M+H) + ] :819

[0324]

[0325] [Synthesization Example 8] Synthesis of 4'-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (Compound 049)

[0326]

[0327] Compound B01 (10.0 g, 18.6 mmol) synthesized in Preparation Example 11, 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.4 g, 18.6 mmol), Pd(PPh3)4 (0.6 g, 0.6 mmol), and K2CO3 (7.7g, 55.9mmol) was added to 100ml of toluene, 15.0ml of ethanol, and 15.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4'-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (10.0g, 14.0mmol, yield 75%).

[0328] Mass : [(M+H) + ] :719

[0329]

[0330] [Synthesization Example 9] Synthesis of 4'-(4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (Compound 146)

[0331]

[0332] Compound B01 (10.0 g, 18.6 mmol) synthesized in Preparation Example 11, 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (6.7 g, 18.6 mmol), Pd(PPh3)4 (0.6 g, 0.6 mmol), and K2CO3 7.7g (55.9mmol) was added to 100ml of toluene, 15.0ml of ethanol, and 15.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4'-(4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (10.1g, 13.8mmol, yield 74%).

[0333] Mass : [(M+H) + ] :733

[0334]

[0335] [Synthesizing Example 10] Synthesis of (2',4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)(methyl)phosphinite (Compound 148)

[0336]

[0337] Compound B08 (10.0 g, 17.5 mmol) synthesized in Preparation Example 18, 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (6.3 g, 17.5 mmol), Pd(PPh3)4 (0.6 g, 0.5 mmol), and K2CO3 (7.2g, 52.4mmol) was added to 100ml of toluene, 15.0ml of ethanol, and 15.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain (2',4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)(methyl)phosphinite (8.8g, 12.9mmol, yield 74%).

[0338] Mass : [(M+H) + ] :679

[0339]

[0340] [Synthesization Example 11] Synthesis of 2',4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3,4-dicarbonitrile (Compound 149)

[0341]

[0342] Compound B09 (10.0 g, 17.8 mmol) synthesized in Preparation Example 19, 2-chloro-4,6-diphenyl-1,3,5-triazine (4.8 g, 17.8 mmol), Pd(PPh3)4 (0.6 g, 0.5 mmol), and K2CO3 (7.4g, 53.4mmol) was added to 100ml of toluene, 15.0ml of ethanol, and 15.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2',4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3,4-dicarbonitrile (8.7g, 13.0mmol, yield 73%).

[0343] Mass : [(M+H) + ] :668

[0344]

[0345] [Synthesization Example 12] Synthesis of 4'-(2,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4,4''-dicarbonitrile (Compound 169)

[0346]

[0347] Compound B10 (10.0 g, 14.0 mmol) synthesized in Preparation Example 20, 2-chloro-4,6-diphenyl-1,3,5-triazine (3.8 g, 14.0 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol), and K2CO3 5.8g (42.0mmol) was added to 100ml of toluene, 15.0ml of ethanol, and 15.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the organic layer was extracted with methylene chloride, water was removed from the extracted organic layer with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4'-(2,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4,4''-dicarbonitrile (8.5g, 10.4mmol, yield 74%).

[0348] Mass : [(M+H) + ] :820

[0349]

[0350] [Example 1] Fabrication of a blue organic light-emitting diode

[0351] Compound 001 synthesized in Synthesis Example 1 was purified by high-purity sublimation using a commonly known method, and a blue organic electroluminescent device was fabricated as follows.

[0352] 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.

[0353] On the ITO transparent electrode prepared as described above, compound A and compound B were co-deposited in a weight ratio of 98:2 to form a hole injection layer with a thickness of 100 Å, and then compound A was deposited on top of the hole injection layer to form a hole transport layer with a thickness of 1400 Å. Subsequently, compound C was deposited to a thickness of 50 Å on top of the hole transport layer to form a hole transport auxiliary layer, and compound D and compound E were co-deposited in a weight ratio of 98:2 to form a emitting layer with a thickness of 200 Å. Subsequently, compound F was deposited on top of the emitting layer to form an electron transport auxiliary layer with a thickness of 50 Å, and then compound 001 and compound H were co-deposited in a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å. Subsequently, an organic light-emitting diode was fabricated by depositing LiF on the electron transport layer to form an electron injection layer with a thickness of 10 Å, and then depositing Al on the electron injection layer to form a cathode with a thickness of 1000 Å. The structures of compounds A to H used at this time are as follows.

[0354]

[0355]

[0356]

[0357] [Examples 2 to 12] Fabrication of Blue Organic Electroluminescent Devices

[0358] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound 001, which was used as the electron transport layer material in Example 1.

[0359]

[0360] [Comparative Examples 1 to 4] Fabrication of blue organic electroluminescent devices

[0361] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that the following compounds I to M were each used instead of compound 001 as the electron transport layer material in Example 1. At this time, the structures of the compounds I to M are each as follows.

[0362]

[0363]

[0364] [Evaluation Example 1]

[0365] For the blue organic electroluminescent devices fabricated in Examples 1 to 12 and Comparative Examples 1 to 5, respectively, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA / cm² were measured, and the results are shown in Table 1 below.

[0366] Sample Electron Transport Layer Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 1 Compound 0013.24538.9 Example 2 Compound 0023.34528.8 Example 3 Compound 0033.54538.7 Example 4 Compound 0093.44528.7 Example 5 Compound 0113.64528.8 Example 6 Compound 0313.44548.7 Example 7 Compound 0473.64538.7 Example 8 Compound 0493.74528.6 Example 9 Compound 1463.64548.8 Example 10 Compound 1483.74538.8 Example 11 Compound 1493.64548.7 Example 12 Compound 1693.64558.6 Comparative Example 1 Compound I 4.34557.5 Comparative Example 2 Compound J 4.44547.4 Comparative Example 3 Compound K 4.14557.6 Comparative Example 4 Compound L 4.14547.5 Comparative Example 5 Compound M 4.04557.7

[0367] As shown in Table 1 above, it was found that the blue organic electroluminescent devices of Examples 1 to 12, which used the compounds of the present invention in the electron transport layer, were superior in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent devices of Comparative Examples 1 to 5, which used compounds I to M in the electron transport layer.

[0368] In addition, the compounds of the present invention (compounds 001 to 169) used in Examples 1 to 12 have a structure in which dual argin groups are bonded to each other at a meta-position on a benzene ring, and cyano groups or phosphine oxide groups are bonded to the benzene ring through a linker group (e.g., arylene group), wherein the cyano groups or phosphine oxide groups are bonded at an ortho-position (i.e., position 4 of the benzene ring) relative to one argin group. It was found that the organic electroluminescent devices of Examples 1 to 12 containing these compounds of the present invention are superior in terms of driving voltage and current efficiency compared to Comparative Examples 1 to 5, which contain compounds in which cyano groups are directly bonded to a benzene ring bonded with dual triazines (compounds I and J), and compounds in which cyano groups are not bonded to position 4 of the benzene ring at an ortho-position relative to one argin group, or in which dual argin groups are not bonded to each other at a meta-position (compounds K, L, M).

[0369]

[0370] [Example 13] Fabrication of a blue organic light-emitting diode

[0371] Compound 031 synthesized in Synthesis Example 6 was purified by high-purity sublimation using a commonly known method, and a blue organic electroluminescent device was fabricated as follows.

[0372] 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.

[0373] On the ITO transparent electrode prepared as described above, a hole injection layer with a thickness of 100 Å was formed by co-depositing compound A and compound B in a weight ratio of 98:2, and then compound A was deposited on top of the hole injection layer to form a hole transport layer with a thickness of 1400 Å. Subsequently, a hole transport auxiliary layer with a thickness of 50 Å was formed by depositing compound C on top of the hole transport layer, and a emitting layer with a thickness of 200 Å was formed by co-depositing compound D and compound E in a weight ratio of 98:2. Subsequently, an electron transport auxiliary layer with a thickness of 50 Å was formed by depositing compound O31 on top of the emitting layer, and then an electron transport layer with a thickness of 300 Å was formed by co-depositing compound G and compound H in a weight ratio of 1:1. Subsequently, an organic light-emitting diode was fabricated by depositing LiF on the electron transport layer to form an electron injection layer with a thickness of 10 Å, and then depositing Al on the electron injection layer to form a cathode with a thickness of 1000 Å.

[0374] The structures of compounds A to E, G, and H used at this time are as follows.

[0375]

[0376]

[0377]

[0378] [Examples 14 to 15] Fabrication of blue organic electroluminescent devices

[0379] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 13, except that the compounds listed in Table 2 below were used instead of Compound 031 used in the electron transport auxiliary layer in Example 13.

[0380]

[0381] [Comparative Example 6] Fabrication of a blue organic electroluminescent device

[0382] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 13, except that the following compound F was used instead of compound 031 in the electron transport auxiliary layer in Example 13. The structure of the compound F used at this time is as follows.

[0383]

[0384]

[0385] [Evaluation Example 2]

[0386] For the blue organic electroluminescent devices fabricated in Examples 13 to 15 and Comparative Example 6, respectively, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA / cm² were measured, and the results are shown in Table 2 below.

[0387] Sample Electron Transport Auxiliary Layer Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 13 Compound 0313.64537.8 Example 14 Compound 0493.74557.7 Example 15 Compound 1483.64547.9 Comparative Example 6 Compound F4.54556.9

[0388] As shown in Table 2 above, it was found that the blue organic electroluminescent devices of Examples 13 to 15, which used the compound of the present invention in the electron transport layer, exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent device of Comparative Example 6, which used compound F in the electron transport auxiliary layer.

Claims

1. Organic compound represented by the following chemical formula 1: [Chemical Formula 1] (In the above chemical formula 1, R1 to R4 are identical or different from one another, and each independently hydrogen, 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 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, phosphine group, C1~C 40 alkylphosphine 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, or combined with adjacent groups to form a condensed ring, x is an integer greater than or equal to 1, and L1 is a polyglot aromatic ring of 6 to 60 won, and n is an integer from 0 to 4, and L2 is a single bond, or C1~C 40 alkylene group of, C6~C 60 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclei, a is an integer greater than or equal to 1, and A is a cyano group (-CN) or -P(=O)(Ar1)(Ar2), and Ar1 and Ar2 are identical or different from each other, and each independently contains hydrogen, 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, 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, phosphine group, alkylphosphine group, arylphosphine group, alkylphosphine oxide group, arylphosphine oxide group, arylamine group, and condensation ring of R1 to R4, the aromatic ring group of L1, the alkylene group, arylene group, and heteroarylene group of L2, and the alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, and heteroaryl group of Ar1 and Ar2 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 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 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 5: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] (In the above chemical formulas 2 to 5, R1 to R4, n, L2, a, and A are as defined in paragraph 1, and b1 is an integer from 0 to 4, and b2 is an integer from 0 to 6, and b3 is an integer from 0 to 3, and b4 is an integer from 0 to 5, 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, 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 the arylamine groups).

3. In Paragraph 1, Multiple L2s are identical or different from each other, and Compounds in which L2 is a single bond or is the following linker group L1-1 or L1-2: (In the above linkers L1-1 and L1-2, c1 is an integer from 0 to 4, and c2 is an integer from 0 to 6, and Multiple Rs are identical or different from each other, and R is hydrogen, deuterium (D), halogen group, 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 having 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 the arylamine groups).

4. 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 6 to 13: [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] (In the above chemical formulas 6 to 13, R1 to R4, n, L2, a, Ar1 and Ar2 are each as defined in Paragraph 1, and b1 is an integer from 0 to 4, and b2 is an integer from 0 to 6, and b3 is an integer from 0 to 3, and b4 is an integer from 0 to 5, 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, 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 the arylamine groups).

5. In Paragraph 1, An organic compound represented by the above chemical formula 1 is an organic compound represented by any one of the following chemical formulas 14 to 37: [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] [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] (In the above chemical formulas 14 to 37, R1 to R4, Ar1 and Ar2 are each as defined in Paragraph 1, and a1 is an integer from 1 to 5, and a2 is an integer from 1 to 7, and b1 is an integer from 0 to 4, and b2 is an integer from 0 to 6, and b3 is an integer from 0 to 3, and b4 is an integer from 0 to 5, and c1 is an integer from 0 to 4, and c2 is an integer from 0 to 6, and n1 is an integer from 1 to 4, and n2 is an integer from 1 to 3, and n3 and n4 are integers from 0 to 3, respectively, 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, 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 the arylamine groups).

6. In Paragraph 1, The organic compound represented by the above chemical formula 1 is an organic compound selected from the group consisting of the following compounds: .

7. An anode; a cathode; and 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, comprising an organic compound described in any one of claims 1 to 6.

8. In Paragraph 7, 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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