Compound and organic electroluminescent device containing the same

Abstract

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

Description

[Technical Field]

[0001] The present invention relates to a novel compound and an organic electroluminescent device using the same, and more particularly to a compound having excellent electron injection and transport properties, and an organic electroluminescent device having improved properties such as luminous efficiency, driving voltage, and lifespan by incorporating the compound in one or more organic material layers. [Background technology]

[0002] In an organic electroluminescent device (hereinafter referred to as "organic EL device"), when a current or voltage is applied between the two electrodes, holes are injected from the positive electrode and electrons are injected from the negative electrode 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. 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] The materials for the emissive layer of organic EL devices can be classified into blue, green, and red emitting materials based on the emitted light color. Furthermore, yellow and orange emitting materials are also used to achieve more natural colors. Host / dopant systems are sometimes used as emitting materials to improve color purity and luminous efficiency through energy transfer. The dopant materials are broadly divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. These phosphorescent materials can theoretically improve luminous efficiency by up to four times compared to fluorescent materials, so interest is focused not only on phosphorescent dopants but also on phosphorescent host materials.

[0004] Currently, NPB, BCP, and Alq3, which are represented by the following formula, are widely known as materials used in hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and 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 useful as phosphorescent materials, offering significant advantages in terms of improved efficiency. These metal complex compounds are used as blue, green, and red dopants. Currently, CBP is demonstrating excellent properties as a phosphorescent host material.

[0005] However, while conventional organic layer materials have advantages in terms of light-emitting properties, they have low glass transition temperatures and poor thermal stability, resulting in unsatisfactory life spans in organic EL devices. Therefore, there is a need to develop 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 organic compound that has improved electron injection and transport capabilities and excellent thermal stability, and can therefore be used as an organic layer material in 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, thereby achieving 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 the following [Chemical Formula 1].

[0009] [ka] (In the formula, X1 is C, Si, Ge or Sn; A1 to A5 are each N or C(E1), However, at least one of A1 to A5 is C(E1), and one of C(E1) that is not N is bonded to L4; The plurality of E1's are the same or different from each other, a, b, c, d, e, and f are each an integer of 0 to 3, g is an integer from 0 to 4, L1 to L6 are the same or different and each independently represent a direct bond or C1 to C6. 20 Alkylene group, C6-C 30 an arylene group having 5 to 30 ring atoms, a heteroarylene group having 5 to 30 ring atoms, and an ether group (—O—), E1 and R1 to R5 are the same or different and each independently represent hydrogen, 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, 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 groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide groups, C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 arylsulfonyl groups, and C6-C 60 or fused with adjacent groups to form a fused ring; EWG is an electron withdrawing group, The alkylene group, arylene group, and heteroarylene group of L1 to L6, and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, alkylcarbonyl group, arylcarbonyl group, sulfonyl group, alkylsulfonyl group, arylsulfonyl group, and arylamine group of E1 and R1 to R5 each independently represent deuterium (D), halogen, cyano group, nitro group, amino group, C1 to C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 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 groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide group, oxo group (=O), C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 arylsulfonyl group, thioketone group (=S), and C6-C 60 and wherein when there are a plurality of the above substituents, they may be 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, wherein at least one of the one or more organic layers contains the compound described above.

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

[0012] The compound according to the present invention can be used as a material for an organic layer of an organic EL device because it has excellent electron transport and injection capabilities, heat resistance, electrochemical stability, etc. In particular, when the compound according to the present invention is used as a material for an electron transport layer or an electron transport auxiliary layer, 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 electroluminescent device according to a first embodiment of the present invention. [Figure 2] FIG. 3 is a cross-sectional view schematically illustrating an organic electroluminescent device according to a second embodiment of the present invention. [Figure 3] FIG. 4 is a cross-sectional view schematically illustrating an organic electroluminescent device according to a third embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0014] <New compounds> The compound according to the present invention has a structure including a first ring moiety bonded to a functional group containing a Group 14 element of the periodic table; a second ring moiety bonded to the first ring moiety directly or via a linker group (L4); and an electron-withdrawing group (EWG) bonded to the second ring moiety directly or via a linker group (L5), and is represented by the above [Chemical Formula 1]. The compound of the present invention represented by [Chemical Formula 1] has excellent electron injection and transport properties, electrochemical stability, heat resistance, etc., and can therefore be used as an electron transport layer material or an electron transport auxiliary layer material that improves the efficiency, long life, and driving voltage characteristics of organic EL devices.

[0015] In the compound according to the present invention, the first ring moiety is a benzene ring moiety or a 6-membered heterocyclic moiety, and a functional group containing a Group 14 element of the periodic table (hereinafter referred to as a "Group 14 element-containing functional group") is bonded to the first ring moiety. Examples of Group 14 elements include, but are not limited to, carbon (C), silicon (Si), germanium (Ge), and tin (Sn). By containing a Group 14 element-containing functional group, the compound of the present invention can break conjugation and have a bulky shape. As a result, the compound of the present invention has a high triplet energy and a large band gap, which allows adjustment of the balance between holes and electrons. The high T1 energy allows excitons to be collected on the host side while preventing excitons from moving back, thereby improving device efficiency and lifetime.

[0016] In the compound according to the present invention, the electron-withdrawing group (EWG) exhibiting high electron absorption properties is bonded to a second ring moiety (e.g., a benzene ring moiety) directly or via a linker group (L5). The EWG may be a heterocyclic moiety containing one or more heteroatoms (e.g., nitrogen, oxygen, or sulfur atoms), such as pyrazinyl, pyrimidinyl, pyridazinyl, phenoxathienyl, indolizinyl, indolyl, purinyl, benzothiazole, 2-furanyl, or N-imidazolyl, or may be an arylphosphine oxide group, a cyano group, a halogen group, or —CF3. Such an EWG can improve 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 an electron transport layer or an electron transport auxiliary layer of an organic EL device, electrons are smoothly transferred from the negative electrode (or electron injection layer) to the light-emitting layer, resulting in a lower driving voltage of the device and achieving high efficiency and long life characteristics.

[0017] As described above, the compound represented by [Chemical Formula 1] 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 a material for an electron transport auxiliary layer. An organic EL device containing the 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 can be maximized.

[0018] In the compound represented by [Chemical Formula 1] according to the present invention, the first moiety ( [ka] ), the second moiety ( [ka] ), and the third moiety ( [ka] ) can be bonded to various positions on the phenyl ring. However, if the first to third moieties are bonded to the first, second, and third positions on the phenyl ring, respectively, the compound is difficult to synthesize, and the moieties have an excessively bent structure around the phenyl ring, which may result in poor performance. Therefore, in the compound of the present invention, the first to third moieties can be bonded to any one of the following positions on the phenyl ring: the first, second, and fourth positions on the phenyl ring; the first, third, and fifth positions on the phenyl ring; the first, third, and sixth positions on the phenyl ring; or the first, fourth, and fifth positions on the phenyl ring.

[0019] Depending on the binding positions of the first to third moieties, the compound represented by [Chemical Formula 1] above can be embodied as any one of the compounds represented by [Chemical Formula 2] to [Chemical Formula 8] below, but is not limited thereto.

[0020] [ka]

[0021] [ka]

[0022] [ka]

[0023] [ka]

[0024] [ka]

[0025] [ka]

[0026] [ka]

[0027] In the above formula, X1, A1 to A5, a, b, c, d, e, f, g, L1 to L6, R1 to R5, and EWG are as defined in Chemical Formula 1 above.

[0028] In the compound represented by the above [Chemical Formula 1], X1 can be C, Si, Ge, or Sn, specifically Si, Ge, or Sn. For example, X1 can be Si.

[0029] In the compound represented by the above [Chemical Formula 1], A1 to A5 are each N or C(E1), provided that at least one of A1 to A5 is C(E1), and in this case, one of the C(E1) that is not N is linked to L4, and the multiple E1s may be the same or different from each other.

[0030] One or more E1 are the same or different and each independently represent hydrogen, 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-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 groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide groups, C1-C 40 Alkylcarbonyl groups, C6-C 60Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 arylsulfonyl groups, and C6-C 60 or fused with an adjacent group to form a fused ring, and specifically, each independently represents a hydrogen atom, a deuterium atom (D), a halogen group, a cyano group, a nitro group, an amino group, a C1 to C 20 Alkyl groups of C2 to C 20 Alkenyl groups, C2-C 20 Alkynyl groups, C3-C 20 Cycloalkyl groups, heterocycloalkyl groups with 3 to 20 atoms, C6 to C 30 aryl groups, heteroaryl groups having 5 to 30 ring atoms, and C6 to C 30 The arylamine groups may be selected from the group consisting of:

[0031] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, alkylcarbonyl group, arylcarbonyl group, alkylsulfonyl group, arylsulfonyl group, and arylamine group of E1 each independently represent a deuterium (D), a halogen, a cyano group, a nitro group, a C1 to C6 alkyl group, a C1 to C6 aryl ... 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 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 groups, C6-C 60Arylphosphine groups, C6-C 60 Arylphosphine oxide group, oxo group (=O), C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 arylsulfonyl group, thioketone group (=S), and C6-C 60 The arylamine group may be unsubstituted or substituted with one or more substituents selected from the group consisting of the following: In this case, when there are a plurality of the above substituents, they may be the same or different.

[0032] In the compound represented by the above [Chemical Formula 1], a, b, c, d, e, and f are each an integer of 0 to 3, and specifically, can be 0 or 1.

[0033] Here, when a is 0, it means that L1 is a direct bond (single bond), when b is 0, it means that L2 is a direct bond (single bond), when c is 0, it means that L3 is a direct bond (single bond), when d is 0, it means that L4 is a direct bond (single bond), when e is 0, it means that L5 is a direct bond (single bond), and when f is 0, it means that L6 is a direct bond (single bond). Note that when a, b, c, d, e, and f are each an integer of 1 to 3, L1 to L6 are each a divalent linker group, and C1 to C 20 Alkylene group, C6-C 30 arylene groups having 5 to 30 ring atoms, heteroarylene groups having 5 to 30 ring atoms, and ether groups (—O—), and specifically, 12 Alkylene group, C6-C 18 a heteroarylene group having 5 to 18 ring atoms, and an ether group (-O-). Here, a plurality of L1 to a plurality of L6 may be the same or different.

[0034] The alkylene group, arylene group, and heteroarylene group of L1 to L6 each independently represent a deuterium (D), a halogen, a cyano group, a nitro 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 having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 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 groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide group, oxo group (=O), C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 arylsulfonyl group, thioketone group (=S), and C6-C 60 The arylamine group may be unsubstituted or substituted with one or more substituents selected from the group consisting of the following: In this case, when there are a plurality of the above substituents, they may be the same or different.

[0035] For example, L1 to L6 are the same or different and each independently represent a direct bond or a C6 to C 30 The arylene groups L1 to L6 are each independently selected from the group consisting of deuterium (D), halogen, cyano, nitro, C1 to C6, 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 60aryl 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 groups, C6-C 60 Arylphosphine groups, C6-C 60 arylphosphine oxide groups, and C6-C 60 In this case, when there are a plurality of the above-mentioned substituents, they may be the same or different.

[0036] According to another example, L1 to L6 are the same or different from one another and may each independently be a direct bond or may be selected from the group consisting of a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyrantrenylene group, a carbazolylene group, a thiophenylene group, an indolylene group, a prinylene group, a quinolinylene group, a pyrrolylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, and a pyrimidinylene group. In this case, the phenylene group, biphenylene group, naphthylene group, anthracenylene group, indenylene group, pyrantrenylene group, carbazolylene group, thiophenylene group, indolylene group, prinylene group, quinolinylene group, pyrrolylene group, imidazolylene group, oxazolylene group, thiazolylene group, triazolylene group, pyridinylene group, and pyrimidinylene group each independently contain deuterium (D), halogen, cyano group, C1 to C6 10 and heteroaryl groups having 5 to 10 ring atoms, or may be unsubstituted or substituted with one or more substituents selected from the group consisting of alkyl groups having 5 to 10 ring atoms.

[0037] Depending on L1 to L6, the compound represented by [Chemical Formula 1] above can be a compound represented by any one of [Chemical Formula 5] to [Chemical Formula 7] below, but is not limited thereto.

[0038] [ka]

[0039] [ka]

[0040] [ka]

[0041] [ka]

[0042] [ka]

[0043] [ka]

[0044] [ka]

[0045] In the above formula, X1, A1 to A5, a, b, c, f, g, L1 to L3, L6, R1 to R5, and EWG are each as defined in [Chemical Formula 1] above, n1 and n2 are each an integer of 0 to 3, o and p are each an integer of 0 to 4, A plurality of R6s and a plurality of R7s may be the same or different, and each independently represent a hydrogen atom, a deuterium atom (D), a halogen atom, a cyano group, a nitro group, a C1 to C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 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 groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide groups, C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 arylsulfonyl groups, and C6-C 60 The arylamine groups may be selected from the group consisting of:

[0046] In the compound represented by the above [Chemical Formula 1], EWG is an electron withdrawing group with a large electron absorbing property, and may be a heteroaromatic ring containing at least one nitrogen atom, oxygen atom, or sulfur atom (e.g., pyrazinyl, pyrimidinyl, pyridazinyl, phenoxathienyl, indolizinyl, indolyl, purinyl, benzothiazole, 2-furanyl, N-imidazolyl, etc.); an arylphosphine oxide group; a cyano group (—CN); a halogen group (e.g., —F, —Cl, —Br, —I, etc.); or a trifluoromethyl group (—CF3), or may be a cyano group, a halogen group (e.g., —F, —Cl, —Br, —I, etc.), a trifluoromethyl group (—CF3), an oxo group (═O), a C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C60 an aryl group substituted with one or more substituents selected from the group consisting of an arylsulfonyl group, an aryl group substituted with one or more substituents selected from the group consisting of a thioketone group (=S); a cyano group, a halogen group (e.g., -F, -Cl, -Br, -I, etc.), a trifluoromethyl group (-CF3), an oxo group (=O), a C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 and a thioketone group (═S).

[0047] For example, in the compound represented by the above [Chemical Formula 1], the EWG may be a cyano group (-CN); a halogen group; trifluoromethyl (-CF3); a cyano group, a halogen group, -CF3, an oxo group (=O), a C1 to C2 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 C6-C substituted with one or more substituents selected from the group consisting of arylsulfonyl groups, and thioketone groups (=S) 60 aryl groups; cyano groups, halogen groups, -CF3, oxo (=O), C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 C6-C substituted with one or more substituents selected from the group consisting of arylsulfonyl groups, and thioketone groups (=S) 60 Arylsilyl group; C6-C 60 Aryl phosphine oxide group; C6-C 60 Arylcarbonyl group; C6-C 60and (5- to 21-membered) heteroaryl groups containing one or more of N, O, and S, wherein the arylphosphine oxide group, arylcarbonyl group, arylsulfonyl group, and heteroaryl group of the EWG may each independently be selected from the group consisting of a cyano group, a halogen group, —CF3, an oxo group (═O), a C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 The ring may be unsubstituted or substituted with one or more substituents selected from the group consisting of an arylsulfonyl group, an arylsulfonyl group, and a thioketone group (=S). In this case, when there are a plurality of the above substituents, the plurality of substituents may be the same or different from each other.

[0048] According to another example, in the compound represented by the above [Chemical Formula 1], the EWG may be selected from a cyano group (—CN), a halogen group, trifluoromethyl (—CF3), and substituents represented by the following formulae S1 to S15.

[0049] [ka]

[0050] [ka]

[0051] In the above formulas S1 to S15, h is an integer from 0 to 5; h1 and h2 are each an integer of 0 to 5, h3 to h5 are integers from 0 to 5, h6 is an integer from 0 to 7, h7 is an integer from 0 to 7, h8 is an integer from 0 to 7, Ar1 and Ar4 each independently represent a cyano group (-CN), a halogen group, a trifluoromethyl group (-CF3), a C1 to C2 40Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 selected from the group consisting of arylsulfonyl groups; Ar2 and Ar3 are the same or different and each independently represent a C6 to C 60 is an aryl group of the formula: Y1 is O, S, C(Q1)(Q2), Si(Q3)(Q4), [ka] , and sulfonic acid groups ( [ka] ) selected from the group consisting of; A plurality of R8's are the same or different from each other, a plurality of R9's are the same or different from each other, and a plurality of R 10 are the same or different from each other, R8~R 10 are the same or different and are each independently selected from the group consisting of a cyano group (-CN), a halogen group, and a trifluoromethyl group (-CF3); Z1 to Z5 are the same or different from one another and each independently represent N or C(Ar5), provided that one or two of Z1 to Z5 are N, and in this case, the multiple Ar5s are the same or different from one another; Z6~Z 10 are the same or different and each independently represent N, N(Ar6), C, C(Ar7), C(Ar8)(Ar9), O or S, provided that Z6 to Z 10 At least one of the Ar6 is N, N(Ar6), O, or S, and the Ar6s are the same or different from one another, and the Ar7s are the same or different from one another; Z 11 ~Z 14 are the same or different, and each independently represents N, C(Ar 10 ), O or S, provided that Z 11 ~Z 14At least one of Ar is N, O or S, and 10 are the same or different from each other; Z 15 ~Z 18 are the same or different and each independently represent N or C(Ar 12 ), where Z 15 ~Z 18 At least one of Ar is N, and 12 are the same or different from each other; Y2 and Y3 are the same or different and each independently represents O, S, N(Ar 13 ) or C(Ar 14 )(Ar 15 ) and Y4 is O or S; Z 19 ~Z 21 are the same or different and each independently represent N, O, S, or C(Ar 16 ), where Z 19 ~Z 21 At least one of Ar is N, O, or S, and 16 are the same or different from each other; Q1~Q5, Ar5~Ar 10 , Ar 12 ~Ar 16 and R are the same or different and each independently represent hydrogen, 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, 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-C60 Arylboron groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide groups, C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 Arylsulfonyl groups, C6-C 60 arylamine groups having 5 to 60 ring atoms, and heteroarylamine groups having (C6 to C 60 or adjacent groups bond to each other to form a fused ring; The aryl groups of Ar2 and Ar3, and Q1 to Q5, Ar5 to Ar 10 , Ar 12 ~Ar 16 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, arylphosphanyl group, arylphosphinyl group, alkylcarbonyl group, arylcarbonyl group, sulfonyl group, alkylsulfonyl group, arylsulfonyl group, arylamine group, heteroarylamine group, and (aryl)(heteroaryl)amine group each independently represent a deuterium (D), a halogen group, a cyano group, a nitro group, a C1 to C6 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-C60 Arylboron groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide group, oxo group (=O), C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 Arylsulfonyl group, thioketone group (=S), C6-C 60 arylamine groups having 5 to 60 ring atoms, and heteroarylamine groups having (C6 to C 60 and (aryl) (heteroaryl) amine groups having 5 to 60 ring atoms, and when there are a plurality of the above substituents, the plurality of substituents may be the same or different.

[0052] As another example, in the compound represented by the above [Chemical Formula 1], the EWG may be, but is not limited to, a cyano group (-CN), a halogen group, a trifluoromethyl group (-CF3), or a substitution product represented by the above formulae A-1 to A-87.

[0053] [ka]

[0054] [ka]

[0055] [ka]

[0056] [ka]

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060] In the above formula, j is an integer from 0 to 4, k is an integer from 0 to 3, l is an integer from 0 to 6, m is an integer from 0 to 5, Y1 is O, S, C(Q1)(Q2), Si(Q3)(Q4), [ka] , and sulfonic acid groups ( [ka] ) selected from the group consisting of; Y5 is O or S; Ring CyA is C6-C 18 is a fused aromatic ring or a fused heteroaromatic ring having 5 to 21 ring atoms, A plurality of Ar5's are the same or different from each other, A plurality of Ar7's are the same or different from one another, Multiple Ar 11 are the same or different from each other, Multiple Ar 12 are the same or different from each other, Q1 to Q5 and Ar5 to Ar 12 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 40Cycloalkyl 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 groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide groups, C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 Arylsulfonyl groups, C6-C 60 arylamine groups having 5 to 60 ring atoms, and heteroarylamine groups having (C6 to C 60 or adjacent groups bond to each other to form a fused ring; The above Q1 to Q5 and Ar5 to Ar 12 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, arylphosphanyl group, arylphosphinyl group, alkylcarbonyl group, arylcarbonyl group, sulfonyl group, alkylsulfonyl group, arylsulfonyl group, arylamine group, heteroarylamine group, and (aryl)(heteroaryl)amine group each independently represent a deuterium (D), a halogen, a cyano group, a nitro group, a C1 to C6 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 60aryl 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 groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide group, oxo group (=O), C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 Arylsulfonyl group, thioketone group (=S), C6-C 60 arylamine groups having 5 to 60 ring atoms, and heteroarylamine groups having (C6 to C 60 and the like. The aryl (heteroaryl) amine group having 5 to 60 ring atoms is unsubstituted or substituted with one or more substituents selected from the group consisting of:

[0061] In the compound represented by the above [Chemical Formula 1], g is an integer of 0 to 4. Here, when g is 0, it means that hydrogen is not substituted with a substituent R4. When g is an integer of 1 to 4, one or more R4s may be the same or different and each independently represent hydrogen, 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, 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 40Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide groups, C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 arylsulfonyl groups, and C6-C 60 or may be fused with an adjacent group to form a fused ring, wherein the heterocycloalkyl group and the heteroaryl group each may contain one or more heteroatoms selected from the group consisting of N, S, O, and Se, and the fused ring is selected from the group consisting of C3 to C6 60 Condensed aliphatic rings (specifically, C3 to C 30 fused aliphatic rings), C6-C 60 fused aromatic rings (specifically, C6 to C 30 The aromatic ring may be one or more selected from the group consisting of fused aromatic rings having 5 to 60 members, and fused heteroaromatic rings having 5 to 60 members (specifically, fused heteroaromatic rings having 5 to 30 members).

[0062] Specifically, one or more R4 are the same or different and each independently represent a deuterium (D), a C1 to C 20 Alkyl groups of C6 to C 30 or is selected from the group consisting of an aryl group having 5 to 30 ring atoms, and a heteroaryl group having 5 to 30 ring atoms, or is bonded to an adjacent group (e.g., R4-R3, R4-L3, R4-L1, R4-L4, R4-R1) to form a C3 to C 30 More specifically, each independently may form a fused aromatic ring of C6 to C 30 or is selected from the group consisting of an aryl group having 5 to 30 ring atoms, and a heteroaryl group having 5 to 30 ring atoms, or is bonded to an adjacent group (e.g., R4-R3, R4-L3, R4-L1, R4-L4, R4-R1) to form a C3 to C 12 may form a fused aromatic ring of the formula:

[0063] In the compound represented by the above [Chemical Formula 1], R1 to R3 and R5 are the same or different and each independently represent hydrogen, 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, 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 groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide groups, C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 arylsulfonyl groups, and C6-C 60 or may be fused with adjacent groups to form a fused ring.

[0064] Specifically, R1 to R3 and R5 are the same or different and each independently represent a deuterium (D), a C1 to C2 20 Alkyl groups of C6 to C 30 or is bonded to an adjacent group (e.g., R1-L1, R1-R4, R2-L2, R2-R4, R3-L3, R3-R4, R5-L6) to form a C3-C 30 More specifically, each independently may form a condensed aromatic ring of C to C 30or is bonded to an adjacent group (e.g., R1-L1, R1-R4, R2-L2, R2-R4, R3-L3, R3-R4, R5-L6) to form a C3-C 12 may form a fused aromatic ring of the formula:

[0065] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, alkylcarbonyl group, arylcarbonyl group, sulfonyl group, alkylsulfonyl group, arylsulfonyl group, and arylamine group of R1 to R5 each independently represent deuterium (D), halogen, cyano group, nitro group, C1 to C6 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 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 groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide group, oxo group (=O), C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 arylsulfonyl group, thioketone group (=S), and C6-C 60and wherein when there are a plurality of the above substituents, they may be the same or different.) For example, R5 may be selected from the group consisting of hydrogen, deuterium (D), a halogen group, a cyano group, and substituents represented by the following formulae B1 to B25.

[0066] [ka]

[0067] [ka]

[0068] In the above formula, a1 is an integer from 0 to 5, a2 is an integer of 0 to 4, a3 is an integer from 0 to 3, a4 is an integer from 0 to 7, a5 is an integer from 0 to 9, W1 and W2 are the same or different and each independently represents S, O, Si(R 13 )(R 14 ), and C(R 15 )(R 16 ) selected from the group consisting of W3 is S, O, Si(R 17 )(R 18 ), C(R 19 )(R 20 ), and N(R 21 ) selected from the group consisting of W4 is Si, Ge, or C; W5 is S or O; Ring Cy1 is C6 to C 18 is a fused aromatic ring or a fused heteroaromatic ring having 5 to 21 ring atoms, Multiple R 11 are the same or different from each other, R 11 ~R 21are 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 groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide groups, C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 arylsulfonyl groups, and C6-C 60 or fused with adjacent groups to form a fused ring; Above R 12 ~R 21 The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, alkylcarbonyl group, arylcarbonyl group, sulfonyl group, alkylsulfonyl group, arylsulfonyl group, and arylamine group each independently represent a deuterium (D), a halogen, a cyano group, a nitro group, an amino group, a C1 to C6 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 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 groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide group, oxo group (=O), C1-C 40 Alkylcarbonyl groups, C6-C 60 Arylcarbonyl group, sulfonyl group, C1-C 40 Alkylsulfonyl groups, C6-C 60 arylsulfonyl group, thioketone group (=S), and C6-C 60 and wherein when there are a plurality of the above substituents, they may be the same or different.) The compound represented by [Chemical Formula 1] according to the present invention can be embodied as any one of the following compounds 1 to 150. However, the compound represented by [Chemical Formula 1] according to the present invention is not limited to the following examples.

[0069] [ka]

[0070] [ka]

[0071] [ka]

[0072] [ka]

[0073] [ka]

[0074] 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.

[0075] 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.

[0076] 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.

[0077] 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.

[0078] 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.

[0079] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms and consisting of 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. 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 in a pendant or fused form, 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.

[0080] 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, and 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.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] 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-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-arylphosphinyl groups.

[0085] 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.

[0086] 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. 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.

[0087] In the present invention, the term "fused ring" refers to a form consisting of 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 fused heteroaromatic ring having 5 to 60 ring atoms, or a combination thereof.

[0088] In the present invention, the "number of core atoms" refers to the number of atoms in the ring constituting the ring structure, and the core atom may be carbon or a heteroatom selected from the group consisting of N, O, S, and Se. For example, the number of core atoms in pyridine is 6, including five C atoms and one N atom constituting the pyridine ring.

[0089] <Organic electroluminescent device> Furthermore, the present invention relates to an organic electroluminescent device (hereinafter abbreviated as "organic EL device") containing the compound represented by the above-mentioned [Chemical Formula 1].

[0090] 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 the compound represented by Chemical Formula 1. In this case, the compounds can be used alone or in combination of two or more.

[0091] The one or more organic material layers 300 may include one or more of a hole injection layer 310, a hole transport layer 320, an emission layer 330, an electron transport layer 340, and an electron injection layer 350, and may optionally further include an electron transport auxiliary layer 360. In this case, at least one organic material layer 300 includes a compound represented by Chemical Formula 1. Specifically, the organic material layer including the compound of Chemical Formula 1 may be the hole transport layer 340 or the electron transport auxiliary layer 360.

[0092] 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 comprises a compound represented by [Chemical Formula 1]. In this case, the compound represented by [Chemical Formula 1] is included in the organic EL device as an electron transport layer material. In such an organic EL device, electrons are easily injected from the cathode or the electron injection layer to the electron transport layer due to the compound represented by [Chemical Formula 1] and can rapidly move from the electron transport layer to the emitting layer, 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 [Chemical Formula 1] has excellent thermal stability and electrochemical stability, enabling improved performance of the organic EL device.

[0093] Such compounds of formula (1) can be used alone or in combination with electron transport layer materials known in the art.

[0094] In the present invention, electron transport layer materials that can be used in combination with the compound of Chemical Formula 1 include electron transport materials well known in the art. Examples of usable electron transport materials include, but are not limited to, oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-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 can be used alone or in combination of two or more.

[0095] In the present invention, when the compound of [Chemical Formula 1] and the electron transport layer material are used in combination, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0096] 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, and the electron transport assist layer includes a compound represented by Chemical Formula 1. In this case, the compound represented by Chemical Formula 1 is included in the organic EL device as an electron transport assist layer material. The compound represented by Chemical Formula 1 has high triplet energy. Therefore, when the compound represented by Chemical Formula 1 is included as an electron transport assist layer material, the efficiency of the organic EL device can be increased due to the triplet-triplet fusion (TTF) effect. Furthermore, the compound represented by Chemical Formula 1 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, and improving the durability and stability of the device, thereby efficiently extending the device's lifespan.

[0097] Such compounds of formula (1) can be used alone or in combination with electron transport layer auxiliary layer materials well known in the art.

[0098] In the present invention, examples of electron transport auxiliary layer materials that can be mixed with the compound of [Chemical Formula 1] include electron transport substances well known in the art, such as oxadiazole derivatives, triazole derivatives, penatroline derivatives (e.g., BCP), and nitrogen-containing heterocyclic derivatives, but are not limited to these.

[0099] The structure of the organic EL device of the present invention described above is not particularly limited, but may be, for example, a structure in which an anode 100, one or more organic layers 300, and a cathode 200 are laminated in this order on a substrate (see FIGS. 1 to 3). Furthermore, although not shown, an insulating layer or adhesive layer may be inserted at the interface between the electrode and the organic layer.

[0100] According to one example, the organic EL device may have 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 may be located between the electron transport layer 340 and the cathode 200. Also, an electron transport auxiliary layer 360 may be located between the emitting layer 330 and the electron transport layer 340 (see Fig. 3).

[0101] 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 electron transport layer 340 or the electron transport auxiliary layer 360) contains the compound represented by Chemical Formula 1 above.

[0102] The organic layer can be formed by vacuum deposition or solution coating, including, but not limited to, spin coating, deep coating, doctor blading, inkjet printing, or thermal transfer.

[0103] 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.

[0104] 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-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline; and carbon black.

[0105] 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, or lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO / Al.

[0106] The hole injection layer, hole transport layer, light emitting layer and electron injection layer are not particularly limited, and conventional materials well known in the art can be used. [Example]

[0107] 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.

[0108] [Preparation Example 1] Synthesis of Compound J-1 [ka]

[0109] Triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(3-bromo-5-chlorophenyl)-4,6-diphenylpyrimidine (4.21 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and the target compound J-1 (3.38 g, 50% yield) was obtained using column chromatography.

[0110] [Preparation Example 2] Synthesis of Compound J-2 [ka]

[0111] Triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 1-bromo-2-chloro-4-(phenylsulfonyl)benzene (3.31 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain an organic layer. After removing the solvent from the filtered organic layer, the target compound J-2 (2.87 g, 49% yield) was obtained using column chromatography.

[0112] [Preparation Example 3] Synthesis of Compound J-3 [ka]

[0113] Triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(3-bromo-4-chlorophenyl)-9-methyl-1,10-phenanthroline (3.83 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and the target compound J-3 (3.06 g, 48% yield) was obtained using column chromatography.

[0114] [Preparation Example 4] Synthesis of Compound J-4 [ka]

[0115] Triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 2-(2-bromo-5-chlorophenyl)-5-(4-(tert-butyl)phenyl)-1,3,4-oxadiazole (3.91 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and the target compound J-4 (3.04 g, 47% yield) was obtained using column chromatography.

[0116] [Preparation Example 5] Synthesis of Compound J-5 [ka]

[0117] Triphenyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 3'-bromo-5'-chloro[1,1'-biphenyl]-3,5-dicarbonitrile (3.17 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and the target compound J-5 (2.63 g, 46% yield) was obtained using column chromatography.

[0118] [Preparation Example 6] Synthesis of Compound J-6 [ka]

[0119] 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(triphenylsilyl)pyridine (4.63 g, 10 mmol), (3'-bromo-5'-chloro[1,1'-biphenyl]-2-yl)(phenyl)methanone (3.71 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain the organic layer. After removing the solvent from the filtered organic layer, the target compound J-6 (2.82 g, 45% yield) was obtained using column chromatography.

[0120] [Preparation Example 7] Synthesis of Compound J-7 [ka]

[0121] Methyldiphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.00 g, 10 mmol), 4-([1,1'-biphenyl]-4-yl)-6-(3-bromo-5-chlorophenyl)-2-phenylpyrimidine (4.97 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain the organic layer. The solvent in the filtered organic layer was removed, and the target compound J-7 (3.04 g, 44% yield) was obtained using column chromatography.

[0122] [Preparation Example 8] Synthesis of Compound J-8 [ka]

[0123] Dimethyl(phenyl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (3.38 g, 10 mmol), 4-(3-bromo-5-chlorophenyl)-9H-fluorene-9-thione (3.85 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and the target compound J-8 (2.22 g, 43% yield) was obtained using column chromatography.

[0124] [Preparation Example 9] Synthesis of Compound J-9 [ka]

[0125] Trimethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (2.76 g, 10 mmol), 8-(3-bromo-5-chloro-[1,1':3',1''-terphenyl]-5'-yl)-1,3,3a1,4,6,7,9-heptaazaphenalene (5.14 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain an organic layer. After removing the solvent from the filtered organic layer, the target compound J-9 (2.45 g, 42% yield) was obtained using column chromatography.

[0126] [Preparation Example 10] Synthesis of Compound J-10 [ka]

[0127] (4-(tert-butyl)phenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (5.18 g, 10 mmol), 5-(3-bromo-4-chlorophenyl)-6-phenylpyrazine-2,3-dicarbonitrile (3.95 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and the target compound J-10 (2.90 g, 41% yield) was obtained using column chromatography.

[0128] [Preparation Example 11] Synthesis of Compound J-11 [ka]

[0129] 5-([1,1'-biphenyl]-2-yldiphenylsilyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (5.39 g, 10 mmol), 2-(3-bromo-5-chlorophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine (4.51 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain an organic layer. After removing the solvent from the filtered organic layer, the target compound J-11 (3.21 g, 41% yield) was obtained using column chromatography.

[0130] [Preparation Example 12] Synthesis of Compound J-12 [ka]

[0131] Tri([1,1'-biphenyl]-3-yl)(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (6.90 g, 10 mmol), (3-bromo-5-chlorophenyl)diphenylphosphine oxide (3.91 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain the organic layer. After removing the solvent from the filtered organic layer, the target compound J-12 (3.67 g, 42% yield) was obtained using column chromatography.

[0132] [Preparation Example 13] Synthesis of Compound J-13 [ka]

[0133] 4-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)benzonitrile (4.87 g, 10 mmol), (3'-bromo-5'-chloro-[1,1'-biphenyl]-3-yl)diphenylphosphine oxide (4.67 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain an organic layer. After removing the solvent from the filtered organic layer, the target compound J-13 (3.21 g, 43% yield) was obtained using column chromatography.

[0134] [Preparation Example 14] Synthesis of Compound J-14 [ka]

[0135] Ethyldiphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.14 g, 10 mmol), 5-(4-bromo-3-chlorophenyl)-2,3-diphenylpyrazine (4.21 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain an organic layer. After removing the solvent from the filtered organic layer, the target compound J-14 (2.76 g, 44% yield) was obtained using column chromatography.

[0136] [Preparation Example 15] Synthesis of Compound J-15 [ka]

[0137] 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3'(triphenylsilyl)-[1,1'-biphenyl]-3-carbonitrile (5.63 g, 10 mmol), 3-bromo-5-chloro-4'-(trifluoromethyl)-1,1'-biphenyl (3.35 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain the organic layer. After removing the solvent from the filtered organic layer, the target compound J-15 (3.11 g, 45% yield) was obtained using column chromatography.

[0138] [Preparation Example 16] Synthesis of Compound J-16 [ka]

[0139] 2-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)-5-phenylpyridine (5.39 g, 10 mmol), 6-(2-bromo-5-chlorophenyl)-3-methyl-1H-isochromen-1-one (3.49 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and the target compound J-16 (3.13 g, 46% yield) was obtained using column chromatography.

[0140] [Preparation Example 17] Synthesis of Compound J-17 [ka]

[0141] 3-(3-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)pyridine (5.39 g, 10 mmol), 2-(3-bromo-5-chlorophenyl)-[1,2,4]triazolo[1,5-a]pyridine (3.08 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and the target compound J-17 (3.01 g, 47% yield) was obtained using column chromatography.

[0142] [Preparation Example 18] Synthesis of Compound J-18 [ka]

[0143] (3-Chlorophenyl)diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.96 g, 10 mmol), 2-(4-bromo-3-chlorophenyl)-4-phenylquinazoline (3.95 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and the target compound J-18 (3.29 g, 48% yield) was obtained using column chromatography.

[0144] [Preparation Example 19] Synthesis of Compound J-19 [ka]

[0145] Di([1,1'-biphenyl]-4-yl)(phenyl)(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-yl)silane (6.90 g, 10 mmol), 6-(3-bromo-5-chlorophenyl)-2-(4-(tert-butyl)phenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (5.18 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, MgSO4 was added, and the organic layer was filtered. After removing the solvent from the filtered organic layer, the target compound J-19 (4.91 g, 49% yield) was obtained using column chromatography.

[0146] [Preparation Example 20] Synthesis of Compound J-20 [ka]

[0147] Triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)germane (5.07 g, 10 mmol), 4-(3-bromo-5-chlorophenyl)-2,6-diphenylpyrimidine (4.21 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO4, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and the target compound J-20 (3.60 g, 50% yield) was obtained using column chromatography.

[0148] [Synthesis Example 1] Synthesis of Compound 1 [ka]

[0149] Compound J-1 (6.77 g, 10 mmol) synthesized in Preparative Example 1, triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 1 (4.00 g, 41% yield) was obtained using column chromatography. Mass: [(M+H) + ]:977

[0150] [Synthesis Example 2] Synthesis of Compound 2 [ka]

[0151] Compound J-2 (5.87 g, 10 mmol) synthesized in Preparative Example 2, triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 2 (3.72 g, 42% yield) was obtained using column chromatography. Mass: [(M+H) + ]:887

[0152] [Synthesis Example 3] Synthesis of Compound 3 [ka]

[0153] Compound J-3 (6.39 g, 10 mmol) synthesized in Preparative Example 3, 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9'-spirobi[fluorene]-2,7-dicarbonitrile (4.92 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 3 (4.15 g, 43% yield) was obtained using column chromatography. Mass: [(M+H) + ]:967

[0154] [Synthesis Example 4] Synthesis of Compound 4 [ka]

[0155] Compound J-4 (6.47 g, 10 mmol) synthesized in Preparative Example 4, 5,5-dimethyl-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5H-dibenzo[b,d]silole (4.12 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 4 (3.94 g, 44% yield) was obtained using column chromatography. Mass: [(M+H) + ]:897

[0156] [Synthesis Example 5] Synthesis of Compound 5 [ka]

[0157] Compound J-5 (5.73 g, 10 mmol) synthesized in Preparative Example 5, 10,10-dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-dibenzo[b,e]oxacillin (3.52 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 5 (3.43 g, 45% yield) was obtained using column chromatography. Mass: [(M+H) + ]:763

[0158] [Synthesis Example 6] Synthesis of Compound 6 [ka]

[0159] Compound J-6 (6.28 g, 10 mmol) synthesized in Preparative Example 6, 2-(dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.94 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 6 (3.49 g, 46% yield) was obtained using column chromatography. Mass: [(M+H) + ]:759

[0160] [Synthesis Example 7] Synthesis of Compound 7 [ka]

[0161] Compound J-7 (6.91 g, 10 mmol) synthesized in Preparative Example 7, 2-(9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.20 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 7 (3.99 g, 47% yield) was obtained using column chromatography. Mass: [(M+H) + ]:849

[0162] [Synthesis Example 8] Synthesis of Compound 8 [ka]

[0163] Compound J-8 (5.17 g, 10 mmol) synthesized in Preparative Example 8, 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (3.69 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 8 (3.47 g, 48% yield) was obtained using column chromatography. Mass: [(M+H) + ]:724

[0164] [Synthesis Example 9] Synthesis of Compound 9 [ka]

[0165] Compound J-9 (5.84 g, 10 mmol) synthesized in Preparative Example 9, 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acenaphtho[1,2-b]pyridine (3.29 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 9 (3.67 g, 49% yield) was obtained using column chromatography. Mass: [(M+H) + ]:750

[0166] [Synthesis Example 10] Synthesis of Compound 10 [ka]

[0167] Compound J-10 (7.07 g, 10 mmol) synthesized in Preparative Example 10, 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]thiophen-4-yl)-1,3,2-dioxaborolane (3.86 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 10 (4.27 g, 50% yield) was obtained using column chromatography. Mass: [(M+H) + ]:855

[0168] [Synthesis Example 11] Synthesis of Compound 11 [ka]

[0169] Compound J-11 (7.84 g, 10 mmol) synthesized in Preparative Example 11, 5-phenyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5H-dibenzo[b,d]silole (4.60 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and then compound 11 (4.43 g, 41% yield) was obtained using column chromatography. Mass: [(M+H) + ]:1082

[0170] [Synthesis Example 12] Synthesis of Compound 12 [ka]

[0171] Compound J-12 (8.75 g, 10 mmol) synthesized in Preparative Example 12, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[4,5]imidazo[1,2-a]pyridine (2.94 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 12 (4.23 g, 42% yield) was obtained using column chromatography. Mass: [(M+H) + ]:1007

[0172] [Synthesis Example 13] Synthesis of Compound 13 [ka]

[0173] Compound J-13 (7.48 g, 10 mmol) synthesized in Preparative Example 13, 2-(dibenzo[b,d]furan-4-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (3.71 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 13 (4.11 g, 43% yield) was obtained using column chromatography. Mass: [(M+H) + ]:957

[0174] [Synthesis Example 14] Synthesis of Compound 14 [ka]

[0175] Compound J-14 (6.29 g, 10 mmol) synthesized in Preparative Example 14, 3-(3-diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)pyridine (5.39 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 14 (4.42 g, 44% yield) was obtained using column chromatography. Mass: [(M+H) + ]:1006

[0176] [Synthesis Example 15] Synthesis of Compound 15 [ka]

[0177] Compound J-15 (6.92 g, 10 mmol) synthesized in Preparative Example 15, 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,2':6',3''-terpyridine (3.59 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and then compound 15 (4.00 g, 45% yield) was obtained using column chromatography. Mass: [(M+H) + ]:889

[0178] [Synthesis Example 16] Synthesis of Compound 16 [ka]

[0179] Compound J-16 (6.82 g, 10 mmol) synthesized in Preparative Example 16, N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (3.71 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 16 (4.09 g, 46% yield) was obtained using column chromatography. Mass: [(M+H) + ]:891

[0180] [Synthesis Example 17] Synthesis of Compound 17 [ka]

[0181] Compound J-17 (6.41 g, 10 mmol), synthesized in Preparative Example 17, 4,4,5,5-tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane (2.96 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 17 (3.64 g, 47% yield) was obtained using column chromatography. Mass: [(M+H) + ]:775

[0182] [Synthesis Example 18] Synthesis of Compound 18 [ka]

[0183] Compound J-18 (6.85 g, 10 mmol) synthesized in Preparative Example 18, 4,4,5,5-tetramethyl-2-(3-(1,2,2-triphenylvinyl)phenyl)-1,3,2-dioxaborolane (9.16 g, 20 mmol), Pd(OAc) (0.44 g, 2 mmol), X-Phos (1.90 g, 4 mmol), and CsCO (13.02 g, 40 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 18 (6.13 g, 48% yield) was obtained using column chromatography. Mass: [(M+H) + ]:1277

[0184] [Synthesis Example 19] Synthesis of Compound 19 [ka]

[0185] Compound J-19 (10.02 g, 10 mmol) synthesized in Preparative Example 19, 1-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazole (3.96 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and then compound 19 (6.05 g, 49% yield) was obtained using column chromatography. Mass: [(M+H)+ ]:1236

[0186] [Synthesis Example 20] Synthesis of Compound 20 [ka]

[0187] Compound J-20 (7.21 g, 10 mmol) synthesized in Preparative Example 20, 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-2-yl)-1,3,2-dioxaborolane (4.58 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. The solvent in the filtered organic layer was removed, and compound 20 (5.08 g, 50% yield) was obtained using column chromatography. Mass: [(M+H) + ]:1017

[0188] [Synthesis Example 21] Synthesis of Compound 21 [ka]

[0189] Triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 4-(4′-chloro[1,1′:2′,1′-terphenyl]-4-yl)-2,6-diphenylpyrimidine (4.95 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100°C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain the organic layer. The solvent in the filtered organic layer was removed, and then the mixture was subjected to column chromatography to obtain compound 21 (3.25 g, 41% yield). Mass: [(M+H) + ]:795

[0190] [Synthesis Example 22] Synthesis of Compound 22 [ka]

[0191] 4,4,5,5-Tetramethyl-2-(3-tritylphenyl)-1,3,2-dioxaborolane (4.46 g, 10 mmol), 2-(5-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (5.09 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, MgSO was added, and the organic layer was filtered. After removing the solvent from the filtered organic layer, compound 22 (3.33 g, 42% yield) was obtained using column chromatography. Mass: [(M+H) + ]:792

[0192] [Synthesis Example 23] Synthesis of Compound 23 [ka]

[0193] Triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)stannane (5.53 g, 10 mmol), 4-([1,1'-biphenyl]-4-yl)-2-(3"-chloro-[1,1':3',1"-terphenyl]-3-yl)-6-phenylpyridine (5.70 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO, and filtered to obtain an organic layer. After removing the solvent from the filtered organic layer, compound 23 (4.13 g, 43% yield) was obtained using column chromatography. Mass: [(M+H) + ]:960

[0194] [Synthesis Example 24] Synthesis of Compound 24 [ka]

[0195] Triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 4-([1,1'-biphenyl]-4-yl)-6-(5-chloro-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine (4.95 g, 10 mmol), Pd(OAc) (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and CsCO (6.51 g, 20 mmol) were added to 100 mL of 1,4-dioxane / 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, MgSO was added, and the organic layer was filtered. After removing the solvent from the filtered organic layer, compound 24 (3.49 g, 44% yield) was obtained using column chromatography. Mass: [(M+H) + ]:795

[0196] [Examples 1 to 24] Fabrication of blue organic electroluminescent devices The compounds synthesized in the above Synthesis Examples 1 to 24 were each purified by sublimation to high purity by a conventional method, and then blue organic electroluminescent devices were fabricated according to the following process.

[0197] 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, it was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaning machine (Power sonic 405, manufactured by Fashin Tech Co., Ltd.) where it was cleaned using UV for 5 minutes before being transferred to a vacuum deposition machine.

[0198] An organic electroluminescent device was fabricated by stacking the following layers on the ITO transparent electrode prepared as described above in the following 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:

[0199] [ka]

[0200] Comparative Examples 1 to 3: Production of Blue Organic Electroluminescent Devices A blue organic electroluminescent device was fabricated in the same manner as in Example 1, except that the following compounds HB1, HB2, and HB3 were used as the electron transport assisting layer material instead of Compound 1. The structures of HB1, HB2, and HB3 used here are as follows:

[0201] [ka]

[0202] [Evaluation example 1] For the organic electroluminescent devices manufactured in Examples 1 to 24 and Comparative Examples 1 to 3, 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.

[0203] [Table 1]

[0204] As shown in Table 1 above, it was confirmed that the organic electroluminescent devices manufactured in Examples 1 to 24 were superior in driving voltage, emission peak, and current efficiency to the organic electroluminescent devices manufactured in Comparative Examples 1 to 3, respectively.

[0205] [Examples 25 to 48] Fabrication of blue organic electroluminescent devices The compounds synthesized in the above Synthesis Examples 1 to 24 were each purified by sublimation to high purity by a conventional method, and then blue organic electroluminescent devices were fabricated according to the following process.

[0206] 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, it was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaning machine (Power sonic 405, manufactured by Fashin Tech Co., Ltd.) where it was cleaned using UV for 5 minutes before being transferred to a vacuum deposition machine.

[0207] An organic electroluminescent device was fabricated by stacking 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, ET, and Liq used are as follows:

[0208] [ka]

[0209] [Comparative Examples 4 to 6] Production of Blue Organic Electroluminescent Devices A blue organic electroluminescent device was fabricated in the same manner as in Example 25, except that the following compounds ET1, ET2, and ET3 were used as the electron transport layer material instead of Compound 1. The structures of ET1, ET2, and ET3 used here are as follows:

[0210] [ka]

[0211] [Evaluation example 2] For the organic electroluminescent devices manufactured in Examples 25 to 48 and Comparative Examples 4 to 6, 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.

[0212] [Table 2]

[0213] As shown in Table 2 above, it was confirmed that the organic electroluminescent devices manufactured in Examples 25 to 48 were superior in driving voltage, emission peak, and current efficiency to the organic electroluminescent devices manufactured in Comparative Examples 4 to 6, respectively. [Explanation of symbols]

[0214] 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.

Claims

1. A compound represented by the following [Chemical Formula 1]: 【Chemistry 1】 (In the formula, X １ is C, Si, Ge or Sn, A １ ~A ５ are N or C(E １ ) and However, A １ ~A ５ At least one of C(E １ ), and then, C(E １ ) is L ４ is combined with Multiple E's １ are the same or different from each other, a, b, c, d, e, and f are each an integer of 0 to 3; g is an integer from 0 to 4; L １ ~L ６ are the same or different from each other and each independently represent a direct bond or C １ ~C ２０ an alkylene group of C ６ ~C ３０ an arylene group having 5 to 30 ring atoms, a heteroarylene group having 5 to 30 ring atoms, and an ether group (—O—), E １ , and R １ ~R ５ 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 of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of C １ ~C ４０ an alkylcarbonyl group of C ６ ~C ６０ an arylcarbonyl group, a sulfonyl group, １ ~C ４０ an alkylsulfonyl group of C ６ ~C ６０ and an arylsulfonyl group of C ６ ~C ６０ or fused with adjacent groups to form a fused ring, EWG is an electron withdrawing group, The above L １ ~L ６ alkylene groups, arylene groups and heteroarylene groups represented by the formula E １ , and R １ ~R ５ The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, alkylcarbonyl group, arylcarbonyl group, sulfonyl group, alkylsulfonyl group, arylsulfonyl group, and arylamine group each independently represent a deuterium (D), a halogen, a cyano group, a nitro 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, 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 of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group, an oxo group (=O), C １ ~C ４０ an alkylcarbonyl group of C ６ ~C ６０ an arylcarbonyl group, a sulfonyl group, １ ~C ４０ an alkylsulfonyl group of C ６ ~C ６０ an arylsulfonyl group, a thioketone group (=S), and C ６ ~C ６０ and wherein when there are a plurality of the above substituents, they may be the same or different).

2. The compound represented by the formula (1) is represented by any one of the formulas (2) to (8) below. 【Chemistry 2】 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 (In the formula, X １ , A １ ~A ５ , a, b, c, d, e, f, g, L １ ~L ６ , R １ ~R ５ , and EWG are each as defined in claim 1.

3. L １ ~L ６ are the same or different from each other and each independently represent a direct bond or C ６ ~C ３０ is an arylene group of the formula The above L １ ~L ６ The arylene groups each independently represent deuterium (D), halogen, cyano, nitro, 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, 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 of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group, an oxo group (=O), C １ ~C ４０ an alkylcarbonyl group of C ６ ~C ６０ an arylcarbonyl group, a sulfonyl group, １ ~C ４０ an alkylsulfonyl group of C ６ ~C ６０ an arylsulfonyl group, a thioketone group (=S), and C ６ ~C ６０ 2. The compound according to claim 1, wherein the compound is unsubstituted or substituted with one or more substituents selected from the group consisting of arylamine groups of the formula:

4. The compound represented by the formula 1 is represented by any one of the formulas 9 to 15 below. 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 (In the formula, X １ , A １ ~A ５ , a, b, c, f, g, L １ ~L ３ , L ６ , R １ ~R ５ and EWG are each as defined in claim 1; n1 and n2 are each an integer of 0 to 3, o and p are each an integer of 0 to 4; Multiple R ６ and multiple R ７ are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro 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, 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 of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of C １ ~C ４０ an alkylcarbonyl group of C ６ ~C ６０ an arylcarbonyl group, a sulfonyl group, １ ~C ４０ an alkylsulfonyl group of C ６ ~C ６０ and an arylsulfonyl group of C ６ ~C ６０ The arylamine groups may be selected from the group consisting of:

5. The EWG is a cyano group (—CN); a halogen group; a trifluoromethyl group (—CF ３ ), a cyano group (—CN), a halogen group, a trifluoromethyl group (—CF ３ ), oxo group (=O), C １ ~C ４０ an alkylcarbonyl group of C ６ ~C ６０ an arylcarbonyl group, a sulfonyl group, １ ~C ４０ an alkylsulfonyl group of C ６ ~C ６０ and a C substituted with one or more substituents selected from the group consisting of an arylsulfonyl group of the formula: ６ ~C ６０ aryl groups such as cyano groups (-CN), halogen groups, trifluoromethyl groups (-CF ３ ), oxo group (=O), C １ ~C ４０ an alkylcarbonyl group of C ６ ~C ６０ an arylcarbonyl group, a sulfonyl group, １ ~C ４０ an alkylsulfonyl group of C ６ ~C ６０ C substituted with one or more substituents selected from the group consisting of an arylsulfonyl group of the formula: ６ ~C ６０ an arylsilyl group represented by C ６ ~C ６０ an arylphosphine oxide group of ６ ~C ６０ an arylcarbonyl group represented by C ６ ~C ６０ and (5-21 membered) heteroaryl groups containing one or more of N, O, and S, The arylphosphine oxide group, arylcarbonyl group, arylsulfonyl group, and heteroaryl group of the EWG each independently represent a cyano group (—CN), a halogen group, a trifluoromethyl group (—CF ３ ), oxo group (=O), C １ ~C ４０ an alkylcarbonyl group of C ６ ~C ６０ an arylcarbonyl group, a sulfonyl group, １ ~C ４０ an alkylsulfonyl group of C ６ ~C ６０ and thioketone (=S), and when there are a plurality of the substituents, the plurality of substituents are the same or different from each other.

6. The EWG is a cyano group (—CN), a halogen group, a trifluoromethyl group (—CF ３ ) and the compound according to claim 1, which is selected from the group consisting of substituents represented by the following formulae S1 to S15: 【Chemistry 16】 【Chemistry 17】 (In the above formulas S1 to S15, h is an integer from 0 to 5; h1 and h2 are each an integer of 0 to 5, h3 to h5 are each an integer from 0 to 5, h6 is an integer from 0 to 7, h7 is an integer from 0 to 7, h8 is an integer from 0 to 6, Ar １ and Ar ４ are each independently a cyano group (—CN), a halogen group, a trifluoromethyl group (—CF ３ ), C １ ~C ４０ an alkylcarbonyl group of C ６ ~C ６０ an arylcarbonyl group, a sulfonyl group, １ ~C ４０ an alkylsulfonyl group of C ６ ~C ６０ arylsulfonyl groups selected from the group consisting of: Ar ２ and Ar ３ are the same or different from each other, and each independently represents C ６ ~C ６０ is an aryl group of the formula: Y １ は、O、S、C(Q １ )(Q ２ )、Si(Q ３ )(Q ４ )、 [Chemistry 18] and sulfonic acid groups ( 【Chemistry 19】 ) selected from the group consisting of; Multiple R ８ are the same or different, and multiple R ９ are the same or different, and multiple R １０ are the same or different from each other, R ８ ~R １０ are the same or different and each independently represent a cyano group (—CN), a halogen group, or a trifluoromethyl group (—CF ３ ) selected from the group consisting of; Z １ ~Z ５ are the same or different and each independently represent N or C(Ar ５ ) where Z １ ~Z ５ One or two of Ar are N, and at this time, a plurality of Ar ５ are the same or different from each other; Z ６ ~Z １０ are the same or different, and each independently represents N, N(Ar ６ ), C, C(Ar ７ ), C(Ar ８ ) (Ar ９ ), O or S, provided that Z ６ ~Z １０ At least one of N, N(Ar ６ ), O or S, where a plurality of Ar ６ are the same or different, and a plurality of Ar ７ are the same or different from each other; Z １１ ~Z １４ are the same or different, and each independently represents N, C(Ar １０ ), O or S, provided that Z １１ ~Z １４ At least one of Ar is N, O or S, and １０ are the same or different from each other; Z １５ ~Z １８ are the same or different and each independently represent N or C(Ar １２ ), where Z １５ ~Z １８ At least one of Ar is N, and １２ are the same or different from each other; Y ２ and Y ３ are the same or different, and each independently represents O, S, N (Ar １３ ), or C(Ar １４ ) (Ar １５ ) and Y ４ is O or S, Z １９ ~Z ２１ are the same or different and each independently represent N, O, S, or C(Ar １６ ) where Z １９ ~Z ２１ At least one of Ar is N, O, or S, and １６ are the same or different from each other; Q １ ~Q ５ , Ar ５ ~Ar １０ , Ar １２ ~Ar １６ and R 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 of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of C ６ ~C ６０ an arylamine group having 5 to 60 ring atoms; a heteroarylamine group having 5 to 60 ring atoms; ６ ~C ６０ or adjacent groups are bonded to each other to form a fused ring; The above Ar ２ and Ar ３ and the aryl group Q １ ~Q ５ , Ar ５ ~Ar １０ , Ar １０ , Ar １２ ~Ar １６ 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, arylphosphanyl group, arylphosphinyl group, arylamine group, heteroarylamine group, and (aryl)(heteroaryl)amine group each independently represent a deuterium (D), a halogen group, a cyano group, a nitro 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 of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group, an oxo group (=O), C １ ~C ４０ an alkylcarbonyl group of C ６ ~C ６０ an arylcarbonyl group, a sulfonyl group, １ ~C ４０ an alkylsulfonyl group of C ６ ~C ６０ an arylsulfonyl group, a thioketone group (=S), C ６ ~C ６０ an arylamine group having 5 to 60 ring atoms; a heteroarylamine group having 5 to 60 ring atoms; ６ ~C ６０ and (aryl) (heteroaryl) amine groups having 5 to 60 ring atoms, and when there are a plurality of the above substituents, the plurality of substituents may be the same or different.

7. The EWG is a cyano group (—CN), a halogen group, a trifluoromethyl group (—CF ３ ) and the compound represented by the following formulae A-1 to A-87: 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 (In the above formulas A-1 to A-87, j is an integer from 0 to 4, k is an integer from 0 to 3; l is an integer from 0 to 6; m is an integer from 0 to 5; Y １ は、O、S、C(Q １ )(Q ２ )、Si(Q ３ )(Q ４ )、 【Chemistry 27】 , and sulfone groups ( 【Chemistry 28】 ) selected from the group consisting of; Y ５ is O or S, Ring CyA is C ６ ~C １８ or a fused heteroaromatic ring having 5 to 21 ring atoms, Multiple Ar ５ are the same or different from each other, Multiple Ar ７ are the same or different from each other, Multiple Ar １１ are the same or different from each other, Multiple Ar １２ are the same or different from each other, Q １ ~Q ５ , Ar ５ ~Ar １２ 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 of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of C １ ~C ４０ an alkylcarbonyl group of C ６ ~C ６０ an arylcarbonyl group, a sulfonyl group, １ ~C ４０ an alkylsulfonyl group of C ６ ~C ６０ an arylsulfonyl group of C ６ ~C ６０ an arylamine group having 5 to 60 ring atoms; a heteroarylamine group having 5 to 60 ring atoms; ６ ~C ６０ or adjacent groups are bonded to each other to form a fused ring; The above Q １ ~Q ５ , Ar ５ ~Ar １２ 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, arylphosphanyl group, arylphosphinyl group, arylamine group, heteroarylamine group, and (aryl)(heteroaryl)amine group each independently represent a deuterium (D), a halogen, a cyano group, a nitro 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 of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group, an oxo group (=O), C １ ~C ４０ an alkylcarbonyl group of C ６ ~C ６０ an arylcarbonyl group, a sulfonyl group, １ ~C ４０ an alkylsulfonyl group of C ６ ~C ６０ an arylsulfonyl group, a thioketone group (=S), C ６ ~C ６０ an arylamine group having 5 to 60 ring atoms; a heteroarylamine group having 5 to 60 ring atoms; ６ ~C ６０ (aryl) (heteroaryl) amine groups having 5 to 60 ring atoms, and when there are a plurality of the above substituents, they may be the same or different.)

8. The above R ５ is selected from hydrogen, deuterium (D), a halogen group, a cyano group (—CN), and substituents represented by the following formulae B1 to B25: 【Chemistry 29】 【Transformation 30】 (In the above formulas B1 to B25, a1 is an integer from 0 to 5, a2 is an integer from 0 to 4, a3 is an integer from 0 to 3, a4 is an integer from 0 to 7, a5 is an integer from 0 to 9, W １ and W ２ are the same or different and each independently represent S, O, Si(R １３ ) (R １４ ), and C(R １５ ) (R １６ ) selected from the group consisting of W ３ is S, O, Si(R １７ ) (R １８ ), C(R １９ ) (R ２０ ), and N(R ２１ ) selected from the group consisting of W ４ is Si, Ge or C, W ５ is S or O, Ring Cy1 is C ６ ~C １８ or a fused heteroaromatic ring having 5 to 21 ring atoms, Multiple R １１ are the same or different from each other, R １１ ~R ２１ 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 of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of C １ ~C ４０ an alkylcarbonyl group of C ６ ~C ６０ an arylcarbonyl group, a sulfonyl group, １ ~C ４０ an alkylsulfonyl group of C ６ ~C ６０ and an arylsulfonyl group of C ６ ~C ６０ or fused with adjacent groups to form a fused ring; The above R １２ ~R ２１ The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group each independently include deuterium (D), halogen, cyano group, nitro 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, 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 of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group, an oxo group (=O), C １ ~C ４０ an alkylcarbonyl group of C ６ ~C ６０ an arylcarbonyl group, a sulfonyl group, １ ~C ４０ an alkylsulfonyl group of C ６ ~C ６０ an arylsulfonyl group, a thioketone group (=S), and C ６ ~C ６０ and wherein when there are a plurality of the above substituents, they may be the same or different.)

9. The compound represented by the formula (1) is selected from the group consisting of the following compounds 1 to 150: 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】

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

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

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