Organic compound and organic EL device containing the same

Abstract

The present invention relates to a novel organic compound and an organic EL device using the same, and more particularly to an organic compound having excellent electron injection and transport properties and thermal stability, and an organic EL device having improved properties such as luminous efficiency, driving voltage, and lifespan by incorporating the same in one or more organic material layers.

Description

[Technical Field]

[0001] The present invention relates to a novel organic compound and an organic EL device containing the same, more particularly to an organic compound having excellent electron injection and transport properties and thermal stability, and an organic EL device containing the same in one or more organic material layers, thereby improving properties such as luminous efficiency, driving voltage, and lifespan. [Background technology]

[0002] In an organic EL element (hereinafter referred to as "organic EL element"), when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons return to the ground state. The materials used in the organic layer are classified according to their function into light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, electron-injecting materials, etc.

[0003] Materials for forming the light-emitting layer of organic EL devices are classified into blue, green, and red emitting materials depending on the emitted color. Yellow and orange emitting materials are also sometimes used to realize more natural colors. Host / dopant systems can also be used as emitting materials to improve color purity and luminous efficiency through energy transfer. Dopant materials are broadly divided into fluorescent dopants, which use organic materials, and phosphorescent dopants, which use metal complex compounds containing heavy atoms such as Ir and Pt. The development of such phosphorescent materials theoretically improves luminous efficiency by up to four times compared to fluorescence, and interest is focused not only on phosphorescent dopants but also on phosphorescent host materials.

[0004] To date, NPB, BCP, and Alq3, represented by the chemical formula below, are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, while anthracene derivatives have been reported as fluorescent dopant / host materials for light-emitting materials. Among light-emitting materials, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, are particularly well-known as phosphorescent materials that offer significant advantages in terms of improving efficiency, and are used as blue, green, and red dopant materials. Currently, CBP is demonstrating excellent properties as a phosphorescent host material.

[0005] However, while conventional organic layer materials are advantageous in terms of light-emitting properties, they have low glass transition temperatures and poor thermal stability, which means that they are not satisfactory in terms of lifespan in organic EL devices. Therefore, there is a demand for the development of organic layer materials with superior performance. Summary of the Invention [Problem to be solved by the invention]

[0006] An object of the present invention is to provide a novel compound which has improved electron injection and transport capabilities and excellent thermal stability, and which can be used as an organic layer material of an organic EL device, specifically, as an electron transport layer material or an electron transport auxiliary layer material.

[0007] Another object of the present invention is to provide an organic EL device that contains the above-mentioned novel compound and thereby has a low driving voltage, high luminous efficiency, and improved life characteristics. [Means for solving the problem]

[0008] In order to achieve the above object, the present invention provides a compound represented by at least one of the following [Chemical Formula 1] to [Chemical Formula 5].

[0009] [ka] [ka] [ka] [ka] [ka] (In the above formula, a1 and a2 are each an integer of 0 to 4, b1 and b2 are each an integer of 0 to 3, c1, c2, c3, and c4 are each an integer from 0 to 2, However, a1+a2+b1+b2≧1, a1+a2+b1+b2+c1≧1, a1+a2+b1+b2+c1+c2≧1, a1+a2+b1+b2+c1+c2+c3≧1, a1+a2+b1+b2+c1+c2+c3+c4≧1, The plurality of R's may be the same or different and each independently represent a deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1 to C6 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2~ C40 Alkynyl groups, C2-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 10 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron group, phosphine oxide group, C1-C 40 Alkyl phosphine groups, C6-C 60 Arylphosphine groups, C1-C 40 Alkyl phosphine oxide group, C6-C 60 arylphosphine oxide groups, and C6-C 60 or fused with adjacent groups to form a fused ring; However, at least one of the plurality of R is an A moiety represented by the following [Chemical Formula A1] or [Chemical Formula A2]: [ka] [ka] In the above formula, L1 and L2 each independently represent a single bond or a C6 to C 60 is an arylene group of the formula X1 to X5 are the same or different from one another and each independently represent N or C(R3), provided that at least one of X1 to X5 is N, and in this case, when there are multiple C(R3), the multiple R3s are the same or different from one another; R1 to R3 are the same or different and each independently represent a hydrogen atom, a deuterium atom (D), a halogen atom, a cyano group, a nitro group, an amino group, a C1 to C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron group, phosphine oxide group, C1-C 40 Alkyl phosphine groups, C6-C 60 Arylphosphine groups, C1-C 40 Alkyl phosphine oxide group, C6-C 60 arylphosphine oxide groups, and C6-C 60 or fused with adjacent groups to form a fused ring; 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, alkylphosphine group, arylphosphine group, alkylphosphine oxide group, arylphosphine oxide group, arylamine group and fused ring of R and R1 to R3, and the arylene group of L1 and L2 each independently represent deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C1 to C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron group, phosphine oxide group, C1-C 40 Alkyl phosphine groups, C6-C 60 Arylphosphine groups, C1-C 40 Alkyl phosphine oxide group, C6-C 60 arylphosphine oxide groups, and C6-C 60 and when there are a plurality of the above substituents, they are the same or different.

[0010] The present invention also provides an organic EL device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, at least one of which contains the organic compound described above.

[0011] The organic layer containing the organic compound can be an electron transport layer and / or an electron transport auxiliary layer. [Effects of the Invention]

[0012] The compound of the present invention can be used as an organic layer material for an organic EL device because it has excellent electron transport and injection capabilities, heat resistance, electrochemical stability, etc. 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 EL device having superior light-emitting performance, low driving voltage, high efficiency, high-speed mobility, and long life properties compared to conventional materials can be manufactured, and a full-color display panel with improved performance and life can also be manufactured. [Brief explanation of the drawings]

[0013] [Figure 1] 1 is a cross-sectional view schematically illustrating an organic EL element according to a first embodiment of the present invention. [Figure 2] FIG. 3 is a cross-sectional view schematically showing an organic EL element according to a second embodiment of the present invention. [Figure 3] FIG. 10 is a cross-sectional view schematically showing an organic EL element according to a third embodiment of the present invention. [Explanation of symbols]

[0014] 100: anode, 200: cathode, 300: organic layer, 310: hole injection layer, 320: hole transport layer, 330: light emitting layer, 340: electron transport layer, 350: electron injection layer, 360: electron transport auxiliary layer. DETAILED DESCRIPTION OF THE INVENTION

[0015] The present invention will be described below.

[0016] <New organic compounds> The compound according to the present invention comprises a basic skeleton formed by repeatedly bonding ortho-phenylene groups, and further comprises a structure in which a nitrogen-containing heterocyclic moiety (e.g., a pyridine group, a pyrimidine group, a triazine group, etc.), an arylphosphine oxide moiety, or an alkylphosphine oxide moiety is introduced (bonded) to the basic skeleton directly or via a linker group, and is represented by at least one of the above [Chemical Formula 1] to [Chemical Formula 5]. The compound according to the present invention has excellent electron injection and transport capabilities, electrochemical stability, thermal stability, etc., and therefore provides a novel compound that can realize the properties of an organic EL device, such as high efficiency, long life, and low driving voltage of the device.

[0017] Specifically, in the compound according to the present invention, the ortho-phenylene group of the basic skeleton has a pi-conjugated system, while the electron density due to doping is unevenly distributed, resulting in excellent electron conductivity. Because such a basic skeleton is formed by repeatedly bonding ortho-phenylene groups in a helical configuration, the compound according to the present invention has a bulky structure. Furthermore, since the compound according to the present invention contains a basic skeleton with repeatedly bonded ortho-phenylene groups, it has a higher triplet energy (T1) than compounds having a basic skeleton with repeatedly bonded meta-phenylene or para-phenylene groups. Therefore, when the compound according to the present invention is used as an electron transport auxiliary layer material, the efficiency of an organic electroluminescent device can be improved due to the triplet-triplet fusion (TTF) effect. Furthermore, the compound according to the present invention can prevent excitons and holes generated in the emitting layer from diffusing to the electron transport layer adjacent to the emitting layer. Therefore, the number of excitons contributing to light emission in the emitting layer increases, improving the luminous efficiency of the device, enhancing the durability and stability of the device, and efficiently extending the device life.

[0018] Furthermore, in the compound according to the present invention, the nitrogen-containing heterocyclic moiety introduced into the basic skeleton is an electron withdrawing group (EWG) with high electron absorption. Such a nitrogen-containing heterocyclic moiety can improve the electron mobility and the electron transport and injection properties of the compound. Therefore, when the compound according to the present invention is used as a material for the electron transport layer or electron transport auxiliary layer of an organic EL device, electrons are smoothly transported from the cathode (or electron injection layer) to the light-emitting layer, resulting in a low driving voltage of the device and high efficiency and long life.

[0019] Furthermore, when the compound according to the present invention contains an arylphosphine oxide-based moiety or an alkylphosphine oxide-based moiety, it can maximize electron transport properties by forming a coordination bond with a metal complex such as Liq (8-quinolinolato lithium). Therefore, when the compound according to the present invention is used as a material for the electron transport layer or electron transport auxiliary layer of an organic electroluminescent device, electrons are smoothly transported from the cathode (or electron injection layer) to the light-emitting layer, resulting in a low driving voltage of the device and high efficiency and long life.

[0020] As described above, the compound represented by at least one of [Chemical Formula 1] to [Chemical Formula 5] according to the present invention has excellent electron injection and transport properties, thermal stability, electrochemical stability, etc. Therefore, the compound of the present invention can be used as an organic layer of an organic EL device, preferably as an electron transport layer / injection layer material or an electron transport auxiliary layer material, and more preferably as an electron transport layer material or an electron transport auxiliary layer material. An organic EL device containing such a compound of the present invention has significantly improved performance and life characteristics, and the performance of a full-color organic light-emitting panel using such an organic EL device is maximized.

[0021] In the compound according to the present invention, a1 and a2 each represent an integer of 0 to 4, b1 and b2 each represent an integer of 0 to 3, and c1, c2, c3, and c4 each represent an integer of 0 to 2. However, at least one of the Rs is an A moiety represented by the above [Chemical Formula A1] or [Chemical Formula A2]. Therefore, a1+a2+b1+b2≧1, a1+a2+b1+b2+c1≧1, a1+a2+b1+b2+c1+c2≧1, a1+a2+b1+b2+c1+c2+c3≧1, and a1+a2+b1+b2+c1+c2+c3+c4≧1.

[0022] Here, when a1, a2, b1, b2, c1, c2, c3, and c4 are each 0, this means that hydrogen is not substituted with a substituent R. When a1 and a2 are each an integer of 1 to 4, b1 and b2 are each an integer of 1 to 3, and c1, c2, c3, and c4 are each an integer of 1 to 2, one or more Rs may be the same or different and each independently represent deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1 to C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron group, phosphine oxide group, C1-C 40 Alkyl phosphine groups, C6-C 60 Arylphosphine groups, C1-C 40 Alkyl phosphine oxide group, C6-C 60 and C6-C 60 or may be fused with an adjacent group to form a fused ring, wherein the fused ring is selected from the group consisting of C3 to C60 Condensed aliphatic rings (specifically, C3 to C 30 fused aliphatic rings), C6-C 60 fused aromatic rings (specifically, C6 to C 30 and at least one selected from the group consisting of a fused aromatic ring having 5 to 60 members (specifically, a fused heteroaromatic ring having 5 to 30 members), a C3 to C60 spiro ring, and combinations thereof.

[0023] According to one example, the Rs are the same or different and each independently represent a deuterium (D), a cyano group, a C1-C 40 Alkyl groups of C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 alkylphosphine oxide groups, and C6-C 60 or can be fused with adjacent groups to form a fused ring, provided that at least one of the multiple R's is the A moiety represented by [Chemical Formula A1] or [Chemical Formula A2] above.

[0024] 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, alkylphosphine group, arylphosphine group, alkylphosphine oxide group, arylphosphine oxide group, arylamine group, and fused ring in the above R each independently represent deuterium, halogen, cyano group, nitro group, C2 to C6 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 ring atoms, C1 to C 40 Alkyl groups of C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron group, phosphine oxide group, C1-C 40 Alkyl phosphine groups, C6-C 60 Arylphosphine groups, C1-C 40 Alkyl phosphine oxide group, C6-C 60 arylphosphine oxide groups, and C6-C 60 In this case, when there are a plurality of the above-mentioned substituents, they are the same or different.

[0025] However, at least one of the multiple R's is an A moiety and is represented by the above chemical formula A1 or A2.

[0026] According to one example, the A moiety represented by the above formula A1 can be selected from the group consisting of the following moieties S1-1 to S1-10, but is not limited thereto.

[0027] However, at least one of the multiple R's is an A moiety and is represented by the above [Chemical Formula A1] or [Chemical Formula A2].

[0028] In one example, the A moiety represented by the above formula A1 is selected from the group consisting of the following moieties S1-1 to S1-10, but is not limited thereto.

[0029] [ka] In the above Moiety S1-1, X1, X3, and X5 are the same or different and each independently represent N or C(R3), and at least one of X1, X3, and X5 is N; Among the above moieties S1-2, S1-4, S1-6 to S1-9, X1 and X5 are the same or different and each independently represent N or C(R3), and at least one of X1 and X5 is N; Among the above moieties S1-3 and S1-5, X2 and X5 are the same or different and each independently represent N or C(R3), and at least one of X2 and X5 is N; Among the above moieties S1-1 to S1-9, Z1 is O or S; Cy1 is C6 to C 30 Specifically, C6 to C 18 is a fused aromatic ring of Among the above moieties S1-10, X5 and X6 are the same or different and each independently represent N or C(R3), and at least one of X5 and X6 is N; L1 and R3 are as defined above in [Chemical Formula A1], multiple R4's are the same or different, R4 is hydrogen, deuterium (D), halogen, cyano, nitro, amino, C1-C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 arylboron group, phosphine oxide group, C1 to C40 alkylphosphine oxide group, C6 to C 60 Arylphosphine groups, C6-C 60 arylphosphine oxide groups, and C6-C60 or may be fused with adjacent groups to form a fused ring.

[0030] In the A moieties represented by the above [Chemical Formula A1] and [Chemical Formula A2], L1 and L2 are each independently a single bond or a C6-C60 arylene group, specifically, each independently a single bond or selected from the group consisting of a phenylene group, a biphenylene group, and a naphthalene group.

[0031] In this case, the arylene groups of L1 and L2 may be selected from the group consisting of deuterium, halogen, cyano, nitro, C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 ring atoms, C1 to C 40 Alkyl groups of C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron group, phosphine oxide group, C1-C 40 Alkyl phosphine groups, C6-C 60 Arylphosphine groups, C1-C 40 Alkyl phosphine oxide group, C6-C 60 arylphosphine oxide groups, and C6-C 60 In this case, when there are a plurality of the above-mentioned substituents, they are the same or different.

[0032] According to one example, in the above [Chemical Formula A1] and [Chemical Formula A2], L1 and L2 are each independently a single bond or selected from the group consisting of the following linker groups L-1 to L-19, but are not limited thereto.

[0033] [ka] [ka] Among the linker groups L-1 to L-19, i is an integer from 0 to 4, j is an integer from 0 to 6, multiple R4's are the same or different, R4 is deuterium (D), halogen, cyano, nitro, amino, C1-C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron group, phosphine oxide group, C1-C 40 Alkyl phosphine groups, C6-C 60 Arylphosphine groups, C1-C 40 Alkyl phosphine oxide group, C6-C 60 arylphosphine oxide groups, and C6-C 60 or may be fused with adjacent groups to form a fused ring.

[0034] In the above [Chemical Formula A1] and [Chemical Formula A2], X1 to X5 are the same or different and each independently represent N or C(R3), provided that at least one of X1 to X5 is N, and in this case, when there are multiple C(R3), the multiple R3s are the same or different; R1 to R3 are the same or different and each independently represent a hydrogen atom, a deuterium atom (D), a halogen atom, a cyano group, a nitro group, an amino group, a C1 to C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron group, phosphine oxide group, C1-C 40 Alkyl phosphine groups, C6-C 60 Arylphosphine groups, C1-C 40 Alkyl phosphine oxide group, C6-C 60 arylphosphine oxide groups, and C6-C 60 or fused with adjacent groups to form a fused ring; 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, alkylphosphine group, arylphosphine group, alkylphosphine oxide group, arylphosphine oxide group, arylamine group, and fused ring of R1 to R3 each independently represent deuterium, a halogen group, a cyano group, a nitro group, a C2 to C6 alkyl group, a C1 to C6 aryl group, a C2 to C6 aryl ... 40 Alkenyl groups, C2-C 40Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 ring atoms, C1 to C 40 Alkyl groups of C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron group, phosphine oxide group, C1-C 40 Alkyl phosphine groups, C6-C 60 Arylphosphine groups, C1-C 40 Alkyl phosphine oxide group, C6-C 60 arylphosphine oxide groups, and C6-C 60 and when there are a plurality of the above substituents, they are the same or different.

[0035] According to one example, multiple R3s are the same or different from each other, and R3s are selected from the group consisting of the following substituents S1 to S23, but are not limited thereto.

[0036] [ka] [ka]

[0037] Depending on the position where the A moiety is introduced, the compound according to the present invention is represented by any one of the following [Chemical formula 1a] to [Chemical formula 5k], but is not limited thereto.

[0038] [ka] [ka]

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[0039] Specifically, the organic compound represented by any one of the above [Chemical Formula 1] to [Chemical Formula 5] is represented by any one of the following [Chemical Formula 6] to [Chemical Formula 58], but is not limited thereto.

[0040] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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[0041] Depending on the R and A moieties described above, the organic compound represented by any one of the above [Chemical Formula 1] to [Chemical Formula 5] may be represented by any one of the following [Chemical Formula 59] to [Chemical Formula 126], but is not limited thereto.

[0042] [ka] [ka]

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[0043] The organic compounds according to the present invention as described above can be more specifically embodied in the following exemplary compounds, for example, compounds A1 to A120, B1 to B120, C1 to C120, D1 to D104, E1 to E100, F1 to F74, G1 to G88, H1 to H90, I1 to I58, J1 to J120, K1 to K80, L1 to L39, M4 to M45, N1 to N50, and O1 to O64, but are not limited thereto.

[0044] [ka] [ka] [ka] [ka] [ka]

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[0045] In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0046] In the present invention, "alkenyl" means a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon double bonds. Examples of alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

[0047] In the present invention, "alkynyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon triple bonds. Examples of this include, but are not limited to, ethynyl and 2-propynyl.

[0048] In the present invention, the term "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of this include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0049] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 ring atoms, in which one or more carbon atoms, preferably 1 to 3 carbon atoms in the ring, are substituted with a heteroatom such as N, O, S, or Se. Examples include, but are not limited to, morpholine, piperazine, etc.

[0050] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms, which is a single ring or a combination of two or more rings. The two or more rings may be in a pendant or condensed form. Examples of such an aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, etc.

[0051] In the present invention, the term "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 ring atoms. In this case, one or more carbon atoms in the ring, preferably 1 to 3 carbon atoms, are substituted with heteroatoms such as N, O, S, or Se. Two or more rings may be pendant or fused, and may even be fused with an aryl group. Examples of such heteroaryl groups include, but are not limited to, six-membered monocyclic rings such as pyridinyl, 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.

[0052] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' is an alkyl having 1 to 40 carbon atoms. Such alkyloxy may have a linear, branched, or cyclic structure. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0053] 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 this include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, etc.

[0054] In the present invention, "alkylsilyl" means a silyl substituted with an alkyl having 1 to 40 carbon atoms, and includes not only mono- but also di- and tri-alkylsilyl. Furthermore, "arylsilyl" means a silyl substituted with an aryl having 5 to 60 carbon atoms, and includes not only mono- but also polyarylsilyl such as di- and tri-arylsilyl.

[0055] In the present invention, the term "alkylboron group" refers to a boron group substituted with an alkyl having 1 to 40 carbon atoms, and the term "arylboron group" refers to a boron group substituted with an aryl having 6 to 60 carbon atoms.

[0056] In the present invention, the term "alkylphosphinyl group" refers to a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes not only mono- but also di- and tri-alkylphosphinyl groups. In addition, in the present invention, the term "arylphosphinyl group" refers to a phosphine group substituted with a monoaryl or diaryl having 6 to 60 carbon atoms, and includes not only mono- but also di- and tri-arylphosphinyl groups.

[0057] In the present invention, the term "alkylphosphine oxide group" refers to a phosphine oxide group substituted with an alkyl having 1 to 40 carbon atoms, and includes not only mono- but also di-alkylphosphine oxide groups. In addition, in the present invention, the term "arylphosphine oxide group" refers to a phosphine oxide group substituted with a monoaryl or diaryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphine oxide groups.

[0058] In the present invention, the term "arylamine" means an amine substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylamine.

[0059] In the present invention, the term "heteroarylamine" refers to an amine substituted with a heteroaryl having 5 to 60 ring atoms, and includes not only mono- but also di-heteroarylamines.

[0060] In the present invention, the (aryl)(heteroaryl)amine means an amine substituted with an aryl having 6 to 60 carbon atoms and a heteroaryl having 5 to 60 ring atoms.

[0061] In the present invention, the term "fused ring" means a fused aliphatic ring having 3 to 40 carbon atoms, a fused aromatic ring having 6 to 60 carbon atoms, a fused heteroaliphatic ring having 3 to 60 ring atoms, a constricting heteroaromatic ring having 5 to 60 ring atoms, or a combination thereof.

[0062] <Organic EL element> The present invention provides an organic electroluminescence device (hereinafter abbreviated as "organic EL device") containing a compound represented by any one of the above [Chemical Formula 1] to [Chemical Formula 5].

[0063] 1 to 3, the organic EL device according to the present invention comprises an anode 100, a cathode 200, and one or more organic layers 300 interposed between the anode and the cathode, and at least one of the one or more organic layers comprises a compound represented by any one of the above [Chemical Formula 1] to [Chemical Formula 5]. In this case, the above compounds may be used alone or in combination of two or more.

[0064] The one or more organic material layers 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 material layers 300 includes a compound represented by any one of [Chemical Formula 1] to [Chemical Formula 5]. Specifically, the organic material layer including any one of the compounds represented by [Chemical Formula 1] to [Chemical Formula 5] may be at least one of the electron transport layer 340 and the electron transport assist layer 360.

[0065] According to one example, the one or more organic layers include a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, and an electron injection layer, and may optionally further include an electron transport auxiliary layer. The electron transport layer includes a compound represented by any one of [Chemical Formula 1] to [Chemical Formula 5] above. In this case, the compound represented by any one of [Chemical Formula 1] to [Chemical Formula 5] is included in the organic EL device as an electron transport layer material. In such an organic EL device, electrons can be easily injected from the cathode or the electron injection layer to the electron transport layer and can rapidly move from the electron transport layer to the emitting layer due to the compound represented by any one of [Chemical Formula 1] to [Chemical Formula 5] above, thereby enhancing the binding strength between holes and electrons in the emitting layer. Therefore, the organic EL device of the present invention has excellent luminous efficiency, power efficiency, brightness, etc. Furthermore, the compound represented by any one of [Chemical Formula 1] to [Chemical Formula 5] above has excellent thermal stability and electrochemical stability, thereby improving the performance of the organic EL device.

[0066] Any one of the compounds represented by formulas 1 to 5 may be used alone or in combination with electron transport layer materials known in the art.

[0067] In the present invention, electron transport layer materials that can be mixed with any one of the compounds represented by Chemical Formulas 1 to 5 include electron transport materials well known in the art. Usable electron transport materials include, for example, oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadizole-based compounds, perylene-based compounds, aluminum complexes (e.g., Alq3, tris(8-quinolinolato)-aluminum), and gallium complexes (e.g., Gaq'2OPiv)Gaq'2OAc, 2(Gaq'2)). These may be used alone or in combination of two or more.

[0068] In the present invention, when any one of the compounds represented by the above [Chemical Formula 1] to [Chemical Formula 5] is used in combination with an electron transport layer material, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0069] According to another example, the one or more organic layers include a hole injection layer, a hole transport layer, an emitting layer, an electron transport assist layer, an electron transport layer, and an electron injection layer. The electron transport assist layer includes a compound represented by any one of [Chemical Formula 1] to [Chemical Formula 5]. The compound represented by any one of [Chemical Formula 1] to [Chemical Formula 5] is an electron transport assist layer material included in an organic EL device. The compound represented by any one of [Chemical Formula 1] to [Chemical Formula 5] has a high triplet energy. Therefore, when the compound represented by any one of [Chemical Formula 1] to [Chemical Formula 5] is included as an electron transport assist layer material, the efficiency of the organic EL device is improved due to the TTF effect. Furthermore, the compound represented by any one of [Chemical Formula 1] to [Chemical Formula 5] can prevent excitons and holes generated in the emitting layer from diffusing to the electron transport layer adjacent to the emitting layer. This increases the number of excitons contributing to light emission in the emitting layer, improving the luminous efficiency of the device. The durability and stability of the device are also improved, effectively extending the device's lifespan.

[0070] Any one of the compounds of [Chemical Formula 1] to [Chemical Formula 5] can be used alone or in combination with a material for the electron transport layer auxiliary layer known in the art.

[0071] In the present invention, the electron transport auxiliary layer material that can be mixed with any of the compounds of [Chemical Formula 1] to [Chemical Formula 5] above includes electron transport substances well known in the art, such as, but not limited to, oxadiazole derivatives, triazole derivatives, penatroline derivatives (e.g., BCP), and nitrogen-containing heterocyclic derivatives.

[0072] The structure of the organic EL device of the present invention as described above is not particularly limited, but for example, it can be formed by laminating an anode 100, one or more organic layers 300, and a cathode 200 in this order on a substrate (see FIGS. 1 to 3). Furthermore, although not shown, the device may have a structure in which an insulating layer or adhesive layer is inserted at the interface between the electrode and the organic layer.

[0073] According to one example, the organic EL device has a structure in which an anode 100, a hole injection layer 310, a hole transport layer 320, an 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 is provided between the electron transport layer 340 and the cathode 200. In addition, an electron transport auxiliary layer 360 may be provided between the emitting layer 330 and the electron transport layer 340 (see Fig. 3).

[0074] The organic EL device of the present invention can be manufactured by forming the organic layers and electrodes using materials and methods well known in the art, except that at least one of the organic layers 300 (e.g., the light-emitting layer 330, the electron transport layer 340, or the electron transport auxiliary layer 360) contains a compound represented by any one of the above [Chemical Formula 1] to [Chemical Formula 5].

[0075] The organic layer can be formed by vacuum deposition or solution coating, including, but not limited to, spin coating, deep coating, doctor blade coating, inkjet printing, and thermal transfer.

[0076] The substrate that can be used in the present invention is not particularly limited, and examples thereof include, but are not limited to, silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, and the like.

[0077] Examples of anode materials include, but are not limited to, 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 SnO:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-polyethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline; and carbon black.

[0078] Examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO / Al.

[0079] The hole injection layer, hole transport layer, light emitting layer, and electron injection layer are not particularly limited, and materials well known in the art can be used. [Example]

[0080] The present invention will be described in detail below with reference to examples. However, the examples described below are merely illustrative of the present invention, and the present invention is not limited to these examples.

[0081] [Synthesis Example 1] Synthesis of Compound A1 [ka] Under a nitrogen stream, 2-chloro-1,1':2',1'':2'',1'''-quaterphenyl (15.00 g, 44.01 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (19.16 g, 44.01 mmol), Pd(OAc) (0.30 g, 1.32 mmol), CsCO (28.68 g, 88.02 mmol), X-Phos (2.10 g, 4.40 mmol), 200 mL of 1,4-dioxane, and 50 mL of HO were mixed and stirred at 110 °C for 4 hours. After the reaction was completed, the mixture was extracted with dichloromethane, filtered with MgSO. After removing the solvent from the filtered organic layer, the target organic compound (22 g, yield: 85%) was obtained using column chromatography. GC-Mass (theoretical value: 613.76 g / mol, measured value: 613 g / mol)

[0082] [Synthesis Example 2] Synthesis of Compound A6 [ka] The target organic compound (26 g, yield: 87%) was obtained in the same manner as in Synthesis Example 1, except that 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 689.86 g / mol, measured value: 689 g / mol)

[0083] [Synthesis Example 3] Synthesis of Compound A7 [ka] The target organic compound (27 g, yield: 90%) was obtained in the same manner as in Synthesis Example 1, except that 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 688.87 g / mol, measured value: 688 g / mol)

[0084] [Synthesis Example 4] Synthesis of Compound A12 [ka] The target organic compound (25 g, yield: 85%) was obtained in the same manner as in Synthesis Example 1, except that 4-([1,1'-biphenyl]-3-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 688.87 g / mol, measured value: 688 g / mol)

[0085] [Synthesis Example 5] Synthesis of Compound A93 [ka] The target organic compound (27 g, yield: 90%) was obtained in the same manner as in Synthesis Example 1, except that 2-(dibenzo[b,d]furan-4-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 702.86 g / mol, measured value: 702 g / mol)

[0086] [Synthesis Example 6] Synthesis of Compound B12 [ka] Under a nitrogen stream, 2-chloro-1,1':2',1'':2'',1':2''',1''''-quinquiphenyl (15.00 g, 35.98 mmol), 4-([1,1'-biphenyl]-3-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (18.36 g, 35.98 mmol), Pd(OAc) (0.24 g, 1.08 mmol), CsCO (23.44 g, 71.95 mmol), X-Phos (1.72 g, 3.60 mmol), 200 mL of 1,4-dioxane, and 50 mL of HO were mixed and stirred at 110 °C for 4 hours. After the reaction was completed, the mixture was extracted with dichloromethane, filtered with MgSO. After removing the solvent from the filtered organic layer, the target organic compound (27 g, yield: 80%) was obtained using column chromatography. GC-Mass (theoretical value: 764.97 g / mol, measured value: 764 g / mol)

[0087] [Synthesis Example 7] Synthesis of Compound B11 [ka] The target organic compound (23 g, yield: 85%) was obtained in the same manner as in Synthesis Example 6, except that 2-([1,1'-biphenyl]-3-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 4-([1,1'-biphenyl]-3-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine used in Synthesis Example 6. GC-Mass (theoretical value: 765.96 g / mol, measured value: 765 g / mol)

[0088] [Synthesis Example 8] Synthesis of Compound C1 [ka] Under a nitrogen stream, 2-chloro-1,1':2',1'':2'',1''':2''',1'''':2'''',1''''''-sexiphenyl (15.00 g, 30.42 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (13.24 g, 30.42 mmol), Pd(OAc) (0.20 g, 0.91 mmol), CsCO (19.82 g, 60.85 mmol), X-Phos (1.45 g, 3.04 mmol), 200 mL of 1,4-dioxane, and 50 mL of HO were mixed and stirred at 110 °C for 4 hours. After the reaction was completed, the mixture was extracted with dichloromethane, filtered with MgSO. After removing the solvent from the filtered organic layer, the target organic compound (17 g, yield: 75%) was obtained using column chromatography. GC-Mass (theoretical value: 765.96 g / mol, measured value: 765 g / mol)

[0089] [Synthesis Example 9] Synthesis of Compound C11 [ka] The target organic compound (18 g, yield: 73%) was obtained in the same manner as in Synthesis Example 8, except that 2-([1,1′-biphenyl]-3-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 8. GC-Mass (theoretical value: 842.06 g / mol, measured value: 842 g / mol)

[0090] [Synthesis Example 10] Synthesis of Compound C17 [ka] The target organic compound (19 g, yield: 75%) was obtained in the same manner as in Synthesis Example 8, except that 4-([1,1′-biphenyl]-2-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 8. GC-Mass (theoretical value: 841.07 g / mol, measured value: 841 g / mol)

[0091] [Synthesis Example 11] Synthesis of Compound D41 [ka] Dibenzo[b,d]furan-1-ylboronic acid (10.00 g, 47.17 mmol), 2-(2"-chloro[1,1':2',1"-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (23.40 g, 47.17 mmol), Pd(OAc) (0.32 g, 1.42 mmol), CsCO (30.74 g, 94.34 mmol), X-Phos (2.25 g, 4.72 mmol), 200 mL of 1,4-dioxane, and 50 mL of HO were mixed under a nitrogen stream and stirred at 110 °C for 4 hours. After the reaction was completed, the mixture was extracted with dichloromethane, filtered with MgSO. After removing the solvent from the filtered organic layer, the target organic compound (23 g, yield: 80%) was obtained using column chromatography. GC-Mass (theoretical value: 627.75 g / mol, measured value: 627 g / mol)

[0092] [Synthesis Example 12] Synthesis of Compound D89 [ka] The target organic compound (26 g, yield: 80%) was obtained in the same manner as in Synthesis Example 11, except that 4-([1,1'-biphenyl]-4-yl)-6-(2''-chloro-[1,1':2',1''-terphenyl]-3-yl)-2-phenylpyrimidine was used instead of 2-(2''-chloro[1,1':2',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 11. GC-Mass (theoretical value: 702.86 g / mol, measured value: 702 g / mol)

[0093] [Synthesis Example 13] Synthesis of Compound D43 [ka] Under a nitrogen stream, (9,9-dimethyl-9H-fluoren-4-yl)boronic acid (10.00 g, 42.00 mmol), 2-(2"-chloro[1,1':2',1"-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (20.83 g, 42.00 mmol), Pd(OAc) (0.28 g, 1.26 mmol), CsCO (27.37 g, 84.00 mmol), X-Phos (2.00 g, 4.20 mmol), 200 mL of 1,4-dioxane, and 50 mL of HO were mixed and stirred at 110 °C for 4 hours. After the reaction was completed, the mixture was extracted with dichloromethane, filtered with MgSO. After removing the solvent from the filtered organic layer, the target organic compound (25 g, yield: 92%) was obtained using column chromatography. GC-Mass (theoretical value: 653.83 g / mol, measured value: 653 g / mol)

[0094] [Synthesis Example 14] Synthesis of Compound D91 [ka] The target organic compound (26 g, yield: 80%) was obtained in the same manner as in Synthesis Example 13, except that 4-([1,1'-biphenyl]-4-yl)-6-(2''-chloro-[1,1':2',1''-terphenyl]-3-yl)-2-phenylpyrimidine was used instead of 2-(2''-chloro[1,1':2',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 13. GC-Mass (theoretical value: 728.94 g / mol, measured value: 728 g / mol)

[0095] [Synthesis Example 15] Synthesis of Compound E33 [ka] Under a nitrogen stream, 2-chloro-4'-phenyl-1,1':2',1'':2'',1'''-quaterphenyl (15.00 g, 35.98 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (15.66 g, 35.98 mmol), Pd(OAc) (0.24 g, 1.08 mmol), CsCO (23.44 g, 71.95 mmol), X-Phos (1.72 g, 3.60 mmol), 200 mL of 1,4-dioxane, and 50 mL of HO were mixed and stirred at 110 °C for 4 hours. After the reaction was completed, the mixture was extracted with dichloromethane, filtered with MgSO. After removing the solvent from the filtered organic layer, the target organic compound (21 g, yield: 85%) was obtained using column chromatography. GC-Mass (theoretical value: 689.88 g / mol, measured value: 689 g / mol)

[0096] [Synthesis Example 16] Synthesis of Compound G33 [ka] The target organic compound (22 g, yield: 80%) was obtained in the same manner as in Synthesis Example 13, except that 4-([1,1′-biphenyl]-4-yl)-2-phenyl-(6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 2-4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl-1,3,5-triazine used in Synthesis Example 13. GC-Mass (theoretical value: 764.97 g / mol, measured value: 764 g / mol)

[0097] [Synthesis Example 17] Synthesis of Compound E90 [ka] Under a nitrogen stream, (3-cyanophenyl)boronic acid (5.00 g, 34.03 mmol), 2-(2'''-chloro-[1,1':2',1'':2'',1'''-quaterphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (19.47 g, 34.03 mmol), Pd(OAc) (0.23 g, 1.02 mmol), CsCO (22.17 g, 68.05 mmol), X-Phos (1.62 g, 3.40 mmol), 200 mL of 1,4-dioxane, and 50 mL of HO were mixed and stirred at 110 °C for 4 hours. After the reaction was completed, the mixture was extracted with dichloromethane, filtered with MgSO. After removing the solvent from the filtered organic layer, the target organic compound (17 g, yield: 80%) was obtained using column chromatography. GC-Mass (theoretical value: 638.77 g / mol, measured value: 638 g / mol)

[0098] [Synthesis Example 18] Synthesis of Compound E89 [ka] The target organic compound (16 g, yield: 750%) was obtained in the same manner as in Synthesis Example 17, except that (4-cyanophenyl)boronic acid was used instead of (3-cyanophenyl)boronic acid used in Synthesis Example 17. GC-Mass (theoretical value: 638.77 g / mol, measured value: 638 g / mol)

[0099] [Synthesis Example 19] Synthesis of Compound L2 [ka] The target compound (20 g, yield: 85%) was obtained in the same manner as in Synthesis Example 6, except that (3-(dimethylphosphoryl)phenyl)boronic acid was used instead of 4-([1,1'-biphenyl]-3-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine. GC-Mass (theoretical value: 534.64 g / mol, measured value: 534 g / mol)

[0100] [Synthesis Example 20] Synthesis of Compound L3 [ka] The target compound (18 g, yield: 70%) was obtained in the same manner as in Synthesis Example 8, except that (3-(dimethylphosphoryl)phenyl)boronic acid was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine. GC-Mass (theoretical value: 610.74 g / mol, measured value: 610 g / mol)

[0101] [Synthesis Example 21] Synthesis of Compound L21 [ka] Under a nitrogen stream, 2,2′′-dichloro-1,1′:2′,1′′-terphenyl (5 g, 16.71 mmol), (3-(dimethylphosphoryl)phenyl)boronic acid (9.92 g, 50.14 mmol), Pd(OAc) (0.15 g, 0.67 mmol), CsCO (21.78 g, 66.85 mmol), X-Phos (4.78 g, 10.03 mmol), 1,4-dioxane (200 mL), and HO (50 mL) were mixed and stirred at 110°C for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, filtered with MgSO, and the organic layer was removed of the solvent. The target compound (6.25 g, 70% yield) was obtained using column chromatography. GC-Mass (theoretical value: 534.58 g / mol, measured value: 534 g / mol)

[0102] [Synthesis Example 22] Synthesis of Compound A2 [ka] The target organic compound (26 g, yield: 75%) was obtained in the same manner as in Synthesis Example 1, except that 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 612.78 g / mol, measured value: 612 g / mol)

[0103] [Synthesis Example 23] Synthesis of Compound A21 [ka] The target organic compound (27 g, yield: 70%) was obtained in the same manner as in Synthesis Example 1, except that 2-(naphthalen-1-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 663.82 g / mol, measured value: 663 g / mol)

[0104] [Synthesis Example 24] Synthesis of Compound A16 [ka] The target organic compound (29 g, yield: 72%) was obtained in the same manner as in Synthesis Example 1, except that 2-([1,1′-biphenyl]-2-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 689.86 g / mol, measured value: 689 g / mol)

[0105] [Synthesis Example 25] Synthesis of Compound A26 [ka] The target organic compound (29 g, yield: 75%) was obtained in the same manner as in Synthesis Example 1, except that 2-(naphthalen-2-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 663.82 g / mol, measured value: 663 g / mol)

[0106] [Synthesis Example 26] Synthesis of Compound A54 [ka] The target organic compound (29 g, yield: 71%) was obtained in the same manner as in Synthesis Example 1, except that 2-(dibenzo[b,d]furan-3-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 703.84 g / mol, measured value: 703 g / mol)

[0107] [Synthesis Example 27] Synthesis of Compound A17 [ka] The target organic compound (31 g, yield: 78%) was obtained in the same manner as in Synthesis Example 1, except that 4-([1,1'-biphenyl]-2-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 688.87 g / mol, measured value: 688 g / mol)

[0108] [Synthesis Example 28] Synthesis of Compound A22 [ka] The target organic compound (28 g, yield: 72%) was obtained in the same manner as in Synthesis Example 1, except that 4-(naphthalen-1-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 662.84 g / mol, measured value: 662 g / mol)

[0109] [Synthesis Example 29] Synthesis of Compound A27 [ka] The target organic compound (28 g, yield: 72%) was obtained in the same manner as in Synthesis Example 1, except that 4-(naphthalen-2-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 662.84 g / mol, measured value: 662 g / mol)

[0110] [Synthesis Example 30] Synthesis of Compound A74 [ka] The target organic compound (28 g, yield: 70%) was obtained in the same manner as in Synthesis Example 1, except that 4-(dibenzo[b,d]furan-3-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 702.86 g / mol, measured value: 702 g / mol)

[0111] [Synthesis Example 31] Synthesis of Compound A9 [ka] The target organic compound (29 g, yield: 72%) was obtained in the same manner as in Synthesis Example 1, except that 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 687.89 g / mol, measured value: 687 g / mol)

[0112] [Synthesis Example 32] Synthesis of Compound B1 [ka] The target organic compound (23 g, yield: 72%) was obtained in the same manner as in Synthesis Example 6, except that 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 4-([1,1'-biphenyl]-3-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine used in Synthesis Example 6. GC-Mass (theoretical value: 689.86 g / mol, measured value: 689 g / mol)

[0113] [Synthesis Example 33] Synthesis of Compound B6 [ka] The target organic compound (25 g, yield: 70%) was obtained in the same manner as in Synthesis Example 6, except that 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 4-([1,1'-biphenyl]-3-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine used in Synthesis Example 6. GC-Mass (theoretical value: 765.96 g / mol, measured value: 765 g / mol)

[0114] [Synthesis Example 34] Synthesis of Compound B26 [ka] The target organic compound (26 g, yield: 75%) was obtained in the same manner as in Synthesis Example 6, except that 2-(naphthalen-2-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 4-([1,1'-biphenyl]-3-yl))-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine used in Synthesis Example 6. GC-Mass (theoretical value: 739.92 g / mol, measured value: 739 g / mol)

[0115] [Synthesis Example 35] Synthesis of Compound B54 [ka] The target organic compound (26 g, yield: 70%) was obtained in the same manner as in Synthesis Example 6, except that 2-(dibenzo[b,d]furan-3-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 4-([1,1'-biphenyl]-3-yl))-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine used in Synthesis Example 6. GC-Mass (theoretical value: 779.94g / mol, measured value: 779g / mol)

[0116] [Synthesis Example 36] Synthesis of Compound B2 [ka] The target organic compound (26 g, yield: 80%) was obtained in the same manner as in Synthesis Example 6, except that 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 4-([1,1'-biphenyl]-3-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine used in Synthesis Example 6. GC-Mass (theoretical value: 688.87 g / mol, measured value: 688 g / mol)

[0117] [Synthesis Example 37] Synthesis of Compound B7 [ka] The target organic compound (28 g, yield: 77%) was obtained in the same manner as in Synthesis Example 6, except that 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 4-([1,1'-biphenyl]-3-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine used in Synthesis Example 6. GC-Mass (theoretical value: 764.97 g / mol, measured value: 764 g / mol)

[0118] [Synthesis Example 38] Synthesis of Compound B17 [ka] The target organic compound (27 g, yield: 75%) was obtained in the same manner as in Synthesis Example 6, except that 4-([1,1'-biphenyl]-2-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 4-([1,1'-biphenyl]-3-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine used in Synthesis Example 6. GC-Mass (theoretical value: 764.97 g / mol, measured value: 764 g / mol)

[0119] [Synthesis Example 39] Synthesis of Compound B27 [ka] The target organic compound (26 g, yield: 75%) was obtained in the same manner as in Synthesis Example 6, except that 4-(naphthalen-2-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 4-([1,1'-biphenyl]-3-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine used in Synthesis Example 6. GC-Mass (theoretical value: 738.93 g / mol, measured value: 738 g / mol)

[0120] [Synthesis Example 40] Synthesis of Compound B20 [ka] The target organic compound (23 g, yield: 65%) was obtained in the same manner as in Synthesis Example 6, except that 2-([1,1'-biphenyl]-2-yl)-6-phenyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 4-([1,1'-biphenyl]-3-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine used in Synthesis Example 6. C-Mass (theoretical value: 763.98 g / mol, measured value: 763 g / mol)

[0121] [Synthesis Example 41] Synthesis of Compound D1 [ka] Under a nitrogen atmosphere, 2-chloro-1,1':2',1':2'',1':2''',1'''':2'''',1''''':2'''',1''''''-septiphenyl (20.00 g, 35.14 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl-1,3,5-triazine (15.30 g, 35.14 mmol), Pd(OAc)2 (0.24 A mixture of 22.90 g (70.28 mmol), X-Phos (1.68 g, 3.51 mmol), 200 ml of 1,4-dioxane, and 50 ml of H2O was stirred at 110 °C for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and then filtered after adding MgSO4. The solvent in the filtered organic layer was removed, and the target organic compound (22 g, yield: 75%) was obtained using column chromatography. GC-Mass (theoretical value: 764.97 g / mol, measured value: 764 g / mol)

[0122] [Synthesis Example 42] Synthesis of Compound D2 [ka] The target organic compound (22 g, yield: 75%) was obtained in the same manner as in Synthesis Example 6, except that 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl-1,3,5-triazine used in Synthesis Example 41. C-Mass (theoretical value: 841.07 g / mol, measured value: 841 g / mol)

[0123] [Synthesis Example 43] Synthesis of Compound D9 [ka] The target organic compound (36 g, yield: 80%) was obtained in the same manner as in Synthesis Example 1, except that 2-([1,1':2',1''-terphenyl]-2-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 765.96 g / mol, measured value: 765 g / mol)

[0124] [Synthesis Example 44] Synthesis of Compound D10 [ka] The target organic compound (35 g, yield: 72%) was obtained in the same manner as in Synthesis Example 1, except that 2-([1,1':2',1'':2'',1''''-quaterphenyl]-2-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 842.06 g / mol, measured value: 842 g / mol)

[0125] [Synthesis Example 45] Synthesis of Compound D15 [ka] The target organic compound (34 g, yield: 77%) was obtained in the same manner as in Synthesis Example 1, except that 2,4-di([1,1'-biphenyl]-2-yl)-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 765.96 g / mol, measured value: 765 g / mol)

[0126] [Synthesis Example 46] Synthesis of Compound D49 [ka] Under a nitrogen stream, 2-(2'''-chloro-[1,1':2',1'':2'',1'''-quaterphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (20.00 g, 34.96 mmol), dibenzo[b,d]furan-1-ylboronic acid (7.41 g, 34.96 mmol), Pd(OAc) (0.24 g, 1.05 mmol), CsCO (22.78 g, 69.92 mmol), X-Phos (1.67 g, 3.50 mmol), 200 mL of 1,4-dioxane, and 50 mL of HO were mixed and stirred at 110 °C for 4 hours. After the reaction was completed, the mixture was extracted with dichloromethane, filtered with MgSO. After removing the solvent from the filtered organic layer, the target organic compound (16 g, yield: 65%) was obtained using column chromatography. GC-Mass (theoretical value: 703.84 g / mol, measured value: 703 g / mol)

[0127] [Synthesis Example 47] Synthesis of Compound D50 [ka] The target organic compound (18 g, yield: 68%) was obtained in the same manner as in Synthesis Example 46, except that dibenzo[b,d]thiophen-1-ylboronic acid was used instead of dibenzo[b,d]furan-1-ylboronic acid used in Synthesis Example 46. GC-Mass (theoretical value: 719.91 g / mol, measured value: 719 g / mol)

[0128] [Synthesis Example 48] Synthesis of Compound F3 [ka] Under a nitrogen stream, 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (20.00 g, 45.94 mmol), 2-(2'-chloro[1,1'-biphenyl]-2-yl)-3-phenylnaphthalene (17.96 g, 45.94 mmol), Pd(OAc) (0.31 g, 1.38 mmol), CsCO (29.94 g, 91.88 mmol), X-Phos (2.19 g, 4.59 mmol), 200 mL of 1,4-dioxane, and 50 mL of HO were mixed and stirred at 110 °C for 4 hours. After the reaction was completed, the mixture was extracted with dichloromethane, filtered with MgSO. After removing the solvent from the filtered organic layer, the target organic compound (23 g, yield: 75%) was obtained using column chromatography. GC-Mass (theoretical value: 663.82 g / mol, measured value: 663 g / mol)

[0129] [Synthesis Example 49] Synthesis of Compound F5 [ka] The target organic compound (23 g, yield: 77%) was obtained in the same manner as in Synthesis Example 48, except that 2-([1,1'-biphenyl]-2-yl)-3-(2-chlorophenyl)naphthalene was used instead of 2-(2'-chloro[1,1'-biphenyl]-2-yl)-3-phenylnaphthalene used in Synthesis Example 48. GC-Mass (theoretical value: 719.91 g / mol, measured value: 719 g / mol)

[0130] [Synthesis Example 50] Synthesis of Compound F6 [ka] The target organic compound (23 g, yield: 75%) was obtained in the same manner as in Synthesis Example 48, except that 2-([1,1':2',1''-terphenyl]2-yl)-3-chloronaphthalene was used instead of 2-(2'-chloro[1,1'-biphenyl]-2-yl)-3-phenylnaphthalene used in Synthesis Example 48. GC-Mass (theoretical value: 719.91 g / mol, measured value: 719 g / mol)

[0131] [Synthesis Example 51] Synthesis of Compound F7 [ka] The target organic compound (28 g, yield: 72%) was obtained in the same manner as in Synthesis Example 1, except that 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 663.82 g / mol, measured value: 663 g / mol)

[0132] [Synthesis Example 52] Synthesis of Compound H52 [ka] Under a nitrogen stream, 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (20.00 g, 39.18 mmol), 4''-chloro-1,1':2',1'':2'',1':2''',1''''-quinquphenyl (16.34 g, 39.18 mmol), Pd(OAc) (0.26 g, 1.18 mmol), CsCO (25.53 g, 78.36 mmol), X-Phos (1.87 g, 3.92 mmol), 200 mL of 1,4-dioxane, and 50 mL of H2O were mixed and stirred at 110 °C for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, filtered with MgSO4, and then the mixture was cooled to 110 °C for 4 hours. After removing the solvent from the filtered organic layer, the target organic compound (22 g, yield: 72%) was obtained using column chromatography. GC-Mass (theoretical value: 764.97 g / mol, measured value: 764 g / mol)

[0133] [Synthesis Example 53] Synthesis of Compound H64 [ka] The target organic compound (21 g, yield: 70%) was obtained in the same manner as in Synthesis Example 52, except that 4''''-chloro-1,1':2',1'':2'',1''':2'''',1''''-quinquephenyl was used instead of 4''-chloro-1,1':2',1'':2'',1''':2'''',1''''-quinquephenyl used in Synthesis Example 52. GC-Mass (theoretical value: 719.91 g / mol, measured value: 719 g / mol)

[0134] [Synthesis Example 54] Synthesis of Compound I1- [ka] The target organic compound (26 g, yield: 76%) was obtained in the same manner as in Synthesis Example 1, except that 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinazoline was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 586.74g / mol, measured value: 586g / mol)

[0135] [Synthesis Example 55] Synthesis of Compound I37 [ka] The target organic compound (29 g, yield: 80%) was obtained in the same manner as in Synthesis Example 1, except that 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3,13-benzofuro[3,2-d][1,3]chlorazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 626.76 g / mol, measured value: 626 g / mol)

[0136] [Synthesis Example 56] Synthesis of Compound J1 [ka] The target organic compound (27 g, yield: 77%) was obtained in the same manner as in Synthesis Example 1, except that 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 613.76 g / mol, measured value: 613 g / mol)

[0137] [Synthesis Example 57] Synthesis of Compound J7 [ka] The target organic compound (30 g, yield: 75%) was obtained in the same manner as in Synthesis Example 1, except that 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 688.87 g / mol, measured value: 688 g / mol)

[0138] [Synthesis Example 58] Synthesis of Compound J25 [ka] The target organic compound (30 g, yield: 75%) was obtained in the same manner as in Synthesis Example 1, except that 2-(naphthalen-2-yl)-4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 663.82 g / mol, measured value: 663 g / mol)

[0139] [Synthesis Example 59] Synthesis of Compound J21 [ka] The target organic compound (27 g, yield: 70%) was obtained in the same manner as in Synthesis Example 1, except that 2-(naphthalen-1-yl)-4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 663.82 g / mol, measured value: 663 g / mol)

[0140] [Synthesis Example 60] Synthesis of Compound J41 [ka] The target organic compound (23 g, yield: 71%) was obtained in the same manner as in Synthesis Example 6, except that 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 4-([1,1'-biphenyl]-3-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine used in Synthesis Example 6. GC-Mass (theoretical value: 689.86 g / mol, measured value: 689 g / mol)

[0141] [Synthesis Example 61] Synthesis of Compound M16 [ka] The target organic compound (28 g, yield: 71%) was obtained in the same manner as in Synthesis Example 1, except that 2,4-diphenyl-6-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-yl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 689.86 g / mol, measured value: 689 g / mol)

[0142] [Synthesis Example 62] Synthesis of Compound M22 [ka] The target organic compound (36 g, yield: 81%) was obtained in the same manner as in Synthesis Example 1, except that 4-([1,1′-biphenyl]-4-yl)-2-phenyl-6-(4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-3-yl)pyrimidine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 764.97 g / mol, measured value: 764 g / mol)

[0143] [Synthesis Example 63] Synthesis of Compound M31 [ka] The target organic compound (31 g, yield: 78%) was obtained in the same manner as in Synthesis Example 1, except that 2,4-diphenyl-6-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine used in Synthesis Example 1. GC-Mass (theoretical value: 689.86 g / mol, measured value: 689 g / mol)

[0144] [Synthesis Example 64] Synthesis of Compound O2 [ka] Under a nitrogen stream, [1,1':2',1'':2'',1'''-quaterphenyl]-2-ylboronic acid (20.00 g, 57.11 mmol), 2-(2-chloronaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine (22.49 g, 57.11 mmol), Pd(OAc) (0.38 g, 1.71 mmol), CsCO (37.21 g, 114.21 mmol), X-Phos (2.72 g, 5.71 mmol), 200 mL of 1,4-dioxane, and 50 mL of HO were mixed and stirred at 110 °C for 4 hours. After the reaction was completed, the mixture was extracted with dichloromethane, filtered with MgSO. After removing the solvent from the filtered organic layer, the target organic compound (24 g, yield: 65%) was obtained using column chromatography. GC-Mass (theoretical value: 663.82 g / mol, measured value: 663 g / mol)

[0145] [Synthesis Example 65] Synthesis of Compound O4 [ka] The target organic compound (25 g, yield: 67%) was obtained in the same manner as in Synthesis Example 64, except that 2-(4-chloronaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(2-chloronaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 64. GC-Mass (theoretical value: 663.82 g / mol, measured value: 663 g / mol)

[0146] [Synthesis Example 66] Synthesis of Compound O35 [ka] The target organic compound (30 g, yield: 72%) was obtained in the same manner as in Synthesis Example 64, except that 4-([1,1'-biphenyl]-4-yl)-6-(3-chloronaphthalen-1-yl)-2-phenylpyrimidine was used instead of 2-(2-chloronaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 64. GC-Mass (theoretical value: 738.93 g / mol, measured value: 738 g / mol)

[0147] [Synthesis Example 67] Synthesis of Compound N3 [ka] The target organic compound (28 g, yield: 75%) was obtained in the same manner as in Synthesis Example 64, except that 2-(2-chlorophenyl)-9-phenyl-1,10-phenanthroline was used instead of 2-(2-chloronaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 64. GC-Mass (theoretical value: 636.80 g / mol, measured value: 636 g / mol)

[0148] [Synthesis Example 68] Synthesis of Compound N5 [ka] The target organic compound (31 g, yield: 77%) was obtained in the same manner as in Synthesis Example 64, except that 2-chloro-4,7,9-triphenyl-1,10-phenanthroline was used instead of 2-(2-chloronaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 64. GC-Mass (theoretical value: 712.90 g / mol, measured value: 712 g / mol)

[0149] [Examples 1 to 55] Fabrication of blue organic EL devices The compounds synthesized in the above synthesis examples were purified by sublimation to high purity in a conventional manner, and then blue organic EL devices were fabricated according to the following process.

[0150] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) thin film was ultrasonically cleaned in distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaning machine (Powersonic 405, manufactured by Fashin Tech Co., Ltd.) where it was cleaned using UV for 5 minutes before being transferred to a vacuum deposition machine.

[0151] An organic EL device was fabricated by laminating the following layers on the ITO transparent electrode prepared as described above in the order HI+2%HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / BH+2%BD (20 nm) / electron transport auxiliary layer material (5 nm) listed in Table 1 / ET+Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm). The structures of HI, HAT-CN6, EB, BH, BD, ET, and Liq used here are as follows:

[0152] [ka]

[0153] [Comparative Examples 1 to 4] Fabrication of blue organic EL elements Blue organic EL devices were fabricated in the same manner as in Example 1, except that HB1, HB2, HB3, and HB4 were used instead of compound A1, which was used as the electron transporting auxiliary layer material in Example 1. The structures of HB1, HB2, HB3, and HB4 used in these experiments are as follows:

[0154] [ka]

[0155] [Evaluation example 1] For the organic EL devices produced in Examples 1 to 55 and Comparative Examples 1 to 4, a current density of 10 mA / cm 2 The driving voltage, emission wavelength, and current efficiency were measured, and the results are shown in Table 1 below.

[0156] [Table 1] JPEG2025535906000283.jpg175170

[0157] From Table 1 above, it was confirmed that the organic light-emitting devices manufactured in Examples 1 to 55 were superior to the organic light-emitting devices manufactured in Comparative Examples 1 to 4 in terms of driving voltage, emission peak, and current efficiency.

[0158] [Examples 56 to 101] Fabrication of blue organic EL devices The compounds synthesized in the above synthesis examples were purified by sublimation to high purity in a conventional manner, and then blue organic EL devices were fabricated according to the following process.

[0159] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) thin film was ultrasonically cleaned in distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaning machine (Powersonic 405, manufactured by Fashin Tech Co., Ltd.) where it was cleaned using UV for 5 minutes before being transferred to a vacuum deposition machine.

[0160] An organic EL device was fabricated by laminating the following layers on the ITO transparent electrode prepared as described above in the order HI + 2% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / BH + 2% BD (20 nm) / electron transport layer material shown in Table 2 + Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm). The structures of HI, HAT-CN6, EB, BH, BD, and Liq used here are as follows:

[0161] [ka]

[0162] [Comparative Examples 5 to 10] Fabrication of blue organic EL elements Blue organic EL devices were fabricated in the same manner as in Example 19, except that ET, HB2, HB3, HB4, ET-1, and ET-2 were used instead of compound A1 used as the electron transport layer material in Example 19. The structures of ET, HB2, HB3, and HB4 used here are respectively shown below.

[0163] [ka]

[0164] [Evaluation example 2] For the organic EL devices produced in Examples 56 to 101 and Comparative Examples 5 to 10, a current density of 10 mA / cm 2 The driving voltage, emission wavelength, and current efficiency were measured, and the results are shown in Table 2 below.

[0165] [Table 2] JPEG2025535906000287.jpg127170

[0166] From Table 2 above, it was confirmed that the organic light-emitting devices manufactured in Examples 56 to 101 were superior to the organic light-emitting devices manufactured in Comparative Examples 5 to 10 in terms of driving voltage, emission peak, and current efficiency.

Claims

1. An organic compound represented by any one of the following [Chemical Formula 1] to [Chemical Formula 5]. 【Chemistry 1】 【Chemistry 2】 【Transformation 3】 【Chemistry 4】 【Transformation 5】 (In the above formula, a1 and a2 each represent an integer of 0 to 4, b1 and b2 each represent an integer of 0 to 3, c1, c2, c3, and c4 are each an integer of 0 to 2, However, a1+a2+b1+b2≧1, a1+a2+b1+b2+c1≧1, a1+a2+b1+b2+c1+c2≧1, a1+a2+b1+b2+c1+c2+c3≧1, a1+a2+b1+b2+c1+c2+c3+c4≧1, A plurality of R's may be the same or different and each independently represent a deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, or a C １ ~C ４０ alkyl group of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ alkylboron groups of C ６ ~C ６０ an arylboron group, a phosphine oxide group, １ ~C ４０ an alkylphosphine group of C ６ ~C ６０ an arylphosphine group of C １ ~C ４０ alkylphosphine oxide group of C ６ ~C ６０ and an arylphosphine oxide group of C ６ ~C ６０ or fused with adjacent groups to form a fused ring; However, at least one of the multiple R's is an A moiety represented by the following [Chemical Formula 1A] or [Chemical Formula A2]: 【Transformation 6】 【Transformation 7】 In the above formula, L １ and L ２ are each independently a single bond or C ６ ~C ６０ is an arylene group of the formula X １ ~X ５ are the same or different from each other and each independently represent N or C(R ３ ) where X １ ~X ５ At least one of C(R ３ When there are a plurality of R ３ are the same or different from each other, R １ ~R ３ are the same or different and each independently represent hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, C １ ~C ４０ alkyl group of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ alkylboron groups of C ６ ~C ６０ an arylboron group, a phosphine oxide group, １ ~C ４０ an alkylphosphine group of C ６ ~C ６０ an arylphosphine group of C １ ~C ４０ alkylphosphine oxide group of C ６ ~C ６０ and an arylphosphine oxide group of C ６ ~C ６０ or fused with adjacent groups to form a fused ring; The above R and R １ ~R ３ alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, alkylsilyl groups, arylsilyl groups, alkylboron groups, arylboron groups, alkylphosphine groups, arylphosphine groups, alkylphosphine oxide groups, arylphosphine oxide groups, arylamine groups and fused rings, as well as the above-mentioned L １ and L ２ The arylene groups each independently represent a deuterium atom, a halogen atom, a cyano group, a nitro group, or C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, C １ ~C ４０ alkyl group of C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ alkylboron groups of C ６ ~C ６０ an arylboron group, a phosphine oxide group, １ ~C ４０ an alkylphosphine group of C ６ ~C ６０ an arylphosphine group of C １ ~C ４０ alkylphosphine oxide group of C ６ ~C ６０ and an arylphosphine oxide group of C ６ ~C ６０ and when there are a plurality of the above substituents, they are the same or different.)

2. The organic compound according to claim 1, wherein the organic compound represented by any one of the above [Chemical Formula 1] to [Chemical Formula 5] is represented by any one of the following [Chemical Formula 1a] to [Chemical Formula 5k]. 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 (In the above formula, A is an A moiety, and the A moiety is as defined in claim 1, and the multiple A's are the same or different from each other; a1, a2, b1, b2, c1, c2, c3, c4, and R are as defined in claim 1; d1 and d2 are each an integer of 0 to 3, e1 is an integer from 0 to 2, f1 is 0 or 1.

3. A plurality of R's are the same or different and each independently represent a deuterium (D), a cyano group, or C １ ~C ４０ alkyl group of C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ alkylphosphine oxide groups of the formula C ６ ~C ６０ 2. The organic compound of claim 1, wherein the arylphosphine oxide group is selected from the group consisting of:

4. 2. The organic compound according to claim 1, wherein the moiety A represented by the formula (1) is selected from the group consisting of the moieties S1-1 to S1-10 shown below. 【Chemistry 49】 (In the above Moiety S-1, X １ , X ３ , and X ５ are the same or different from each other and each independently represent N or C(R ３ ) where X １ , X ３ , X ５ is N; Among the moieties S1-2, S1-4, S1-6 to S1-9, X １ and X ５ are the same or different from each other and each independently represent N or C(R ３ ) where X １ and X ５ is N; In the moieties S1-3 and S1-5, X ２ and X ５ are the same or different from each other and each independently represent N or C(R ３ ) where X ２ and X ５ is N; Z １ is O or S, Cy1 is C ６ ~C ３０ is a fused aromatic ring of Among the moieties S1-10, X ５ and X ６ are the same or different from each other and each independently represent N or C(R ３ ) where X ５ and X ６ is N; L １ and R ３ are each as defined in claim 1, Multiple R's ４ are the same or different from each other, R ４ represents hydrogen, deuterium (D), halogen, cyano, nitro, amino, C １ ~C ４０ alkyl group of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ alkyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ alkylboron groups of C ６ ~C ６０ an arylboron group, a phosphine oxide group, １ ~C ４０ an alkylphosphine group of C ６ ~C ６０ an arylphosphine group of C １ ~C ４０ alkylphosphine oxide group of C ６ ~C ６０ and an arylphosphine oxide group of C ６ ~C ６０ or can be fused with adjacent groups to form a fused ring.)

5. L １ and L ２ and each independently represent a single bond or a group selected from the group consisting of the following linker groups L-1 to L-19: [Transformation 50] 【Chemistry 51】 (Among the linker groups L-1 to L-19, i is an integer from 0 to 4, j is an integer from 0 to 6, Multiple R's ４ are the same or different from each other, R ４ represents deuterium (D), halogen, cyano, nitro, amino, C １ ~C ４０ alkyl group of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ alkylboron groups of C ６ ~C ６０ an arylboron group, a phosphine oxide group, １ ~C ４０ alkylphosphine oxide group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ and an arylphosphine oxide group of C ６ ~C ６０ or can be fused with adjacent groups to form a fused ring.)

6. Multiple R's ３ are the same or different from each other, R ３ is selected from the group consisting of the following substituents S1 to S23: 【Chemistry 52】 【Chemistry 53】

7. The organic compound represented by any one of the above [Chemical Formula 1] to [Chemical Formula 5] is represented by any one of the following [Chemical Formula 6] to [Chemical Formula 58]. The organic compound according to claim 1. 【Chemistry 54】 【Transformation 55】 【Transformation 56】 【Chemistry 57】 【Chemistry 58】 【Chemistry 59】 【Transformation 60】 【Chemistry 61】 【Transformation 62】 【Transformation 63】 【Chemistry 64】 【Transformation 65】 【Chemical Formula 66】 【Transformation 67】 【Transformation 68】 【Transformation 69】 【Transformation 70】 【Chemistry 71】 【Chemistry 72】 【Transformation 73】 【Chemistry 74】 【Chemistry 75】 【Transformation 76】 【Chemical 77】 【Transformation 78】 【Transformation 79】 【Chemistry 80】 【Chemistry 81】 【Chemistry 82】 【Chemistry 83】 【Chemical 84】 【Chemical 85】 【Chemical 86】 【Transformation 87】 【Chemical 88】 【Chemistry 89】 [Chemical 90] 【Chemistry 91】 【Chemistry 92】 【Chemistry 93】 【Chemical 94】 【Chemical 95】 【Chemistry 96】 【Chemistry 97】 【Chem.98】 【Chem.99】 【Chemistry 100】 【Chemistry 101】 【Chemical Engineering 102】 【Chemistry 103】 【Chemical 104】 【Chemistry 105】 【Chemistry 106】 (In the above formula, a1, b1, b2, c1, c2, c3, c4, R, R １ , R ２ , L １ , and L ２ are each as defined in claim 1, d1 is an integer from 0 to 3, e1 is an integer from 0 to 2, f1 is 0 or 1, X １ , X ３ , and X ５ are the same or different from each other and each independently represent N or (C(R ３ ) where X １ , X ３ , and X ５ At least one of is N, R ３ is as defined in claim 1.

8. The organic compound represented by any one of the above [Chemical Formula 1] to [Chemical Formula 5] is represented by any one of the following [Chemical Formula 59] to [Chemical Formula 126]. The organic compound according to claim 1. 【Chemistry 107】 【Chemistry 108】 【Chemistry 109】 【Chemical 110】 【Chemistry 111】 【Chemistry 112】 【Chemistry 113】 【Chemical 114】 【Chemical 115】 【Chemistry 116】 【Chemistry 117】 【Chemistry 118】 【Chemical 119】 【Chemical 120】 【Chemistry 121】 【Chemistry 122】 【Chemical 123】 【Chemistry 124】 【Chemistry 125】 【Chemistry 126】 【Chemistry 127】 【Chemistry 128】 【Chemistry 129】 【Chemistry 130】 【Chemistry 131】 【Chemistry 132】 【Chemistry 133】 【Chemistry 134】 【Chemistry 135】 【Transformation 136】 【Chemistry 137】 【Chemistry 138】 【Chemistry 139】 [Chemical 140] 【Chemistry 141】 【Chemistry 142】 【Chemistry 143】 【Chemistry 144】 【Chemistry 145】 【Chemistry 146】 【Chemistry 147】 【Chemistry 148】 【Chemistry 149】 [Chemical 150] 【Chemistry 151】 【Chemistry 152】 【Chemistry 153】 【Chemistry 154】 【Chemistry 155】 【Chemistry 156】 【Chemistry 157】 【Chemistry 158】 【Chemistry 159】 [Chemical 160] 【Chemistry 161】 【Chemistry 162】 【Chemical 163】 【Chemistry 164】 【Chemistry 165】 【Chemistry 166】 【Chemistry 167】 【Chemical 168】 【Chemistry 169】 【Chemistry 170】 【Chemistry 171】 【Chemistry 172】 【Chemistry 173】 【Chemistry 174】 (In the above formula, n1, m1, o1, and p1 are each an integer of 0 to 4, n2, n3, n4, m2, m3, m4, o2, o3, o4, p2, p3, and p4 are each an integer of 0 to 3, n5, n6, n7, n8, m5, m6, m7, m8, o5, o6, o7, o8, p5, p6, p7, and p8 are each an integer of 0 to 2, CN is a cyano group; D is deuterium, Me is a methyl group; q1 and q2 each represent an integer of 0 to 1; Y １ is O, S, or C(R ５ ) (R ６ ) and Cy2 is a fused ring selected from the group consisting of the following rings Cy2-1 to Cy2-7: 【Chemistry 175】 X １ , X ３ , and X ５ are the same or different from each other and each independently represent N or C(R ３ ) where X １ , X ３ , and X ５ At least one of is N, L １ , L ２ , R １ , R ２ , and R ３ are each as defined in claim 1, R ５ and R ６ are the same or different and each independently represent hydrogen, deuterium (D), C １ ~C ４０ alkyl group of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, C ６ ~C ６０ and heteroaryl groups having 5 to 60 ring atoms, or may be fused with adjacent groups to form a fused ring.)

9. The organic compound according to claim 1, wherein the organic compound represented by any one of the above [Chemical Formula 1] to [Chemical Formula 5] is selected from the group consisting of the following organic compounds A1 to A120, B1 to B120, C1 to C120, D1 to D104, E1 to E100, F1 to F74, G1 to G88, H1 to H90, I1 to I58, J1 to J120, K1 to K80, L1 to L39, M1 to M45, N1 to N50, and O1 to O64. 【Chemistry 176】 【Chemistry 177】 【Chemistry 178】 【Chemistry 179】 【Chemistry 180】 【Chemistry 181】 【Chemistry 182】 【Chemistry 183】 【Chemistry 184】 【Chemistry 185】 【Chemical 186】 【Chemistry 187】 【Chemical 188】 【Chemical 189】 【Chemistry 190】 【Chemistry 191】 【Chemistry 192】 【Chemistry 193】 【Chemistry 194】 【Chemistry 195】 【Chemistry 196】 【Chemistry 197】 【Chemistry 198】 【Chemistry 199】 【Chemistry 200】 【Chemical Engineering 201】 【Chemical Engineering 202】 【Chemical 203】 【Chemical 204】 【Chemical 205】 【Chemical 206】 【Chemical 207】 【Chemical 208】 【Chemical Engineering 209】 【Chemical 210】

10. an anode, a cathode, and one or more organic layers interposed between the anode and the cathode; 10. An organic EL device, wherein at least one of the one or more organic layers contains the organic compound according to claim 1.

11. The organic EL device according to claim 10 , wherein the organic layer containing the organic compound is an electron transport layer or an electron transport auxiliary layer.

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