Organic light-emitting compound and organic electroluminescent device using same

Abstract

The present invention relates to: a novel compound having excellent carrier transport capability, light-emitting performance and thermal stability; and an organic electroluminescent device comprising same in one or more organic layers thereof, thereby having enhanced luminous efficiency, driving voltage and lifetime.

Description

Organic light-emitting compounds and organic electroluminescent devices using the same

[0001] The present invention relates to a novel organic light-emitting compound and an organic electroluminescent device using the same, and more specifically, to a compound having excellent electron transport capability and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the same in one or more organic layers.

[0002]

[0003] In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall to the ground state. At this time, the materials used as the organic layer can be classified according to their function into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc.

[0004] Luminous materials can be classified according to their emission color into blue, green, and red luminous materials, and yellow and orange luminous materials for realizing better natural colors. In addition, host / dopant systems can be used as luminous materials to increase color purity and luminescence efficiency through energy transfer.

[0005] Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, since the development of phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescence, research is being conducted extensively not only on phosphorescent dopants but also on phosphorescent host materials.

[0006] To date, NPB, BCP, and Alq3 are widely known as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives are reported as materials for emissive layers. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, which have advantages in terms of efficiency improvement among emissive layer materials, are used as blue, green, and red phosphorescent dopant materials, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

[0007] However, while conventional organic layer materials offer advantages in terms of luminescence properties, their low glass transition temperatures result in very poor thermal stability, which is unsatisfactory in terms of the lifespan of organic electroluminescent devices. Therefore, the development of high-performance organic layer materials is required.

[0008]

[0009] The present invention has a technical objective of providing a novel compound that has excellent heat resistance, carrier transport capacity, luminescence capacity, etc., and can be used as an organic layer material for an organic electroluminescent device, specifically as a light-emitting layer material, a lifespan improvement layer material, a light-emitting auxiliary layer material, or an electron transport layer material.

[0010] In addition, the present invention has another technical objective of providing an organic electroluminescent device comprising the novel compound described above, having a low driving voltage, high luminous efficiency, and improved lifespan.

[0011] Other objects and advantages of the present invention may be more clearly explained by the following detailed description of the invention and claims.

[0012]

[0013] To achieve the above-mentioned technical problem, the present invention provides a compound represented by the following chemical formula 1.

[0014] [Chemical Formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] X are identical or different from each other, each independently being N or CR5, provided that at least two of the plurality of X are N,

[0018] Ar1 is C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei,

[0019] Y is O or S,

[0020] R1 to R5 are identical or different from one another, and each independently consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, or R1 to R4 may each combine with any adjacent group to form a condensation ring;

[0021] l is an integer from 0 to 4, and

[0022] m is an integer from 1 to 4, and

[0023] n is an integer from 1 to 7, and

[0024] a is an integer from 0 to 7, and

[0025] b and c are integers from 0 to 4, respectively, and

[0026] d is an integer from 0 to 5, and

[0027] 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, arylamine group, arylheteroarylamine group, heteroarylamine group, and condensation ring of the above Ar1 and R1 to R5 are each independently deuterium (D), halogen, cyano group, nitro group, C1 to C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, and in the case where there are multiple substituents, they may be identical or different from each other.

[0028] In addition, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the chemical formula 1.

[0029] Here, the organic layer comprising the compound represented by Chemical Formula 1 may be selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, a lifetime improvement layer, an electron transport layer, and an electron transport auxiliary layer. In this case, the compound represented by Chemical Formula 1 may be included as at least one material among the phosphorescent host material of the light-emitting layer, the electron transport layer, and the electron transport auxiliary layer.

[0030]

[0031] For example, in one embodiment of the present invention, the compound represented by Chemical Formula 1 can be used as an organic layer material for an organic electroluminescent device because it has excellent electron transport ability, luminescence ability, heat resistance, etc.

[0032] In particular, when a compound represented by Chemical Formula 1 of the present invention is used as an electron transport layer or an electron transport auxiliary layer material, it can exhibit high thermal stability, low driving voltage, fast mobility, high current efficiency, and long lifespan characteristics compared to conventional electron transport materials.

[0033] Accordingly, an organic electroluminescent device containing the compound of Chemical Formula 1 can have excellent luminescence performance, low driving voltage, long lifespan, and high efficiency, and thus can be effectively applied to full-color display panels, etc.

[0034] The effects according to the present invention are not limited to those exemplified above, and a wider variety of effects are included in this specification.

[0035]

[0036] The present invention will be described in detail below.

[0037] <New Organic Compounds>

[0038] The present invention provides a novel compound that exhibits excellent electron transport capacity, luminescence capacity, and thermal stability, thereby enabling the device to display low voltage, high luminescence efficiency, and long lifespan characteristics.

[0039] Specifically, the novel organic compound according to the present invention has a structure in which a cyclic compound having non-covalent electron pairs centered around a nitrogen-containing heteroaromatic ring (e.g., azine, X-containing ring) and a plurality of aryl groups are bonded to form a basic framework, and a naphthalene group is essentially included as one of the plurality of aryl groups.

[0040] The compound represented by the above chemical formula 1 can have higher efficiency and lifespan compared to existing known material structures by controlling electron transport ability through a dibenzo moiety (e.g., a Y-containing ring) which is a ring compound having non-covalent electron pairs, and a plurality of aryl groups including naphthalene groups and aryl groups (e.g., an aromatic ring containing R2 to R4).

[0041] In addition, the compound of Chemical Formula 1 above is structurally designed to increase electron density in the EWG, which possesses electron transport capabilities, by substituting a nitrogen-containing heteroaromatic ring (e.g., triazine, pyrimidine, etc.) with a number of aryl groups having non-covalent electron pairs on the EWG. This results in improved electron transport capabilities compared to previously known material structures, leading to increased efficiency. Furthermore, due to the rigid chemical structure formed by the cyclic compound attached to the EWG, it exhibits excellent performance in terms of high glass transition temperature (Tg) and thermal stability. Moreover, by introducing an argine group, which is a functional group with strong electron-withdrawing ability (EWG), to enhance electron mobility, it becomes possible to obtain physicochemical properties that are more suitable for electron injection and electron transport.

[0042] In addition, by realizing various moietyes through a combination of nitrogen-containing heteroaromatic rings (e.g., X-containing rings) with EWG characteristics and multiple aryl groups, the injection rate can be appropriately controlled, and high chemical stability, a high glass transition temperature (Tg), and excellent thermal stability can be exhibited simultaneously.

[0043] In particular, in the present invention, a more planar molecular structure can be designed by mandatorily introducing a naphthalene group into a structure having multiple aryl groups, which facilitates the control of the mobility of the structure containing the naphthalene group. Furthermore, a trapping effect can be exhibited by controlling the bonding position of the naphthalene; for example, introducing a naphthalene group can have the effect of reducing mobility.

[0044] Furthermore, the maximization of steric hindrance can be induced by controlling the bonding positions of naphthalene groups and additional arylene groups (e.g., phenyl groups), as well as by adding arylene groups. Increasing steric hindrance in this way raises the triplet energy (T1) and suppresses intermolecular interactions, thereby preventing excitons generated in the emissive layer from diffusing (moving) to adjacent electron transport or hole transport layers. Consequently, the number of excitons contributing to luminescence within the emissive layer increases, which can improve the luminous efficiency of the device and enhance the durability and stability of the device, thereby efficiently extending the device's lifespan. Most of the developed materials are capable of low-voltage operation, exhibiting physical characteristics that result in improved lifespan. Additionally, the introduction of additional arylene groups (e.g., phenyl groups) on both sides of the naphthalene moiety adds electron-donating units, which serve to enhance the stability of the bonded EWG. Accordingly, electron donating is enhanced, which can further increase the stability of the molecule.

[0045] In addition, a wide bandgap and a low LUMO value suitable for use as an electron transport layer or electron transport auxiliary layer material for organic light-emitting diodes (OLEDs) are required. The compound of Chemical Formula 1 above can control the LUMO value suitable for the electron transport layer or electron transport auxiliary layer by inducing delocalization of LUMO orbitals due to the structural characteristics described above, can induce a rise in triplet energy through steric hindrance, can gather excitons toward the host, and can increase device efficiency and lifespan through exciton blocks.

[0046] As described above, when a compound represented by Formula 1 of the present invention is applied as an organic layer material of an organic electroluminescent device, preferably as an electron transport layer / electron transport auxiliary layer / injection layer material, an emissive layer material (a blue, green and / or red phosphorescent host material), a hole transport layer / injection layer material, an emissive auxiliary layer material, and a lifespan improvement layer material, the performance and lifespan characteristics of the organic electroluminescent device can be significantly improved. Consequently, such an organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.

[0047] According to the present invention, the compound represented by Formula 1 has a basic skeletal structure that essentially includes a nitrogen-containing heteroaromatic ring (e.g., azine, X-containing ring) having an electron-withdrawing group (EWG) characteristic with excellent electron transport capacity, a cyclic compound having a non-covalent electron pair (e.g., dibenzo moiety, Y-containing ring), and a plurality of aryl groups (e.g., a naphthalene group and a ring containing R2 to R4).

[0048] The above nitrogen-containing heterocyclic ring (e.g., X-containing ring) is a monocyclic nitrogen-containing heteroaryl group containing at least two nitrogen atoms. In one example of a nitrogen-containing heteroaromatic ring, X may be identical or different from each other, and each may independently be CR5 or N, provided that at least two of the plurality of Xs contain N. By including a heterocyclic ring containing two or three nitrogen atoms in this way, superior electron absorption characteristics are exhibited, which is advantageous for electron injection and transport.

[0049] Here, R5 are identical or different from each other and are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei. In this case, if there are multiple R5s, the multiple R5s may be identical or different from each other. Specifically, R5 is hydrogen, deuterium (D), C1~C 40 alkyl group of, C6~C 60 It is preferable to select from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0050] For example, a nitrogen-containing heteroaromatic ring (e.g., a ring containing X) may be further specified as any one selected from the following structural formulas. However, it is not limited thereto.

[0051]

[0052] In the above formula,

[0053] * indicates the part connected to the above chemical formula 1, and

[0054] Ar1, R2, b and l are each as defined in Paragraph 1.

[0055] Ar1 can be substituted as various substituents in the above nitrogen-containing heteroaromatic ring (e.g., X-containing ring). Ar1 is C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It can be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei. Specifically, Ar1 is C1~C 40 alkyl group of, C3~C 40 cycloalkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, wherein the alkyl group, cycloalkyl group, aryl group, and heteroaryl group of Ar1 are each independently deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 It can be substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0056] For example, Ar1 may be embodied in any one of the following structural formulas. However, it is not limited thereto.

[0057]

[0058]

[0059] In the above formula,

[0060] * indicates the part connected to the above chemical formula 1, and

[0061] R 11 It consists of hydrogen, deuterium (D), and C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei. In addition, at least one substituent known in the art (e.g., identical to the R5 definition) that is not indicated in the aforementioned structural formula may be substituted.

[0062] In the compound represented by Formula 1 according to the present invention, one side of the nitrogen-containing heteroaromatic ring (e.g., azine, X-containing ring) comprises a dibenzo moiety as a compound having a non-covalent electron pair. Such a dibenzo moiety (e.g., Y-containing ring) is excellent in terms of high glass transition temperature (Tg) and thermal stability. One example of the dibenzo moiety (e.g., Y-containing ring) is that Y is O or S, specifically O (dibenzofuran) or S (dibenzothiophene).

[0063] In the above dibenzo moiety, R1 can be substituted with various substituents. R1 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C60 The arylamine group of, C5~C 60 It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, or may form a condensed ring by combining with any adjacent group (e.g., R1s together).

[0064] Here, the number of substituents of R1, e.g., a, is not particularly limited and may be an integer from 0 to 7, for example. Here, if a is 0, R1 is hydrogen, and if a is 1 to 7, it may have the aforementioned substituents excluding hydrogen. Also, if a is 2 to 7, multiple R1s may be identical or different from each other.

[0065] Specifically, R1 are identical or different from one another, and each independently hydrogen, deuterium (D), halogen, cyano group, hydrogen, deuterium, C1~C 30 alkyl group of, C3~C 30 cycloalkyl group of, C6~C 30 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclei, or combined with any adjacent group to form a condensation ring, wherein the alkyl group, cycloalkyl group, aryl group, and heteroaryl group are each independently deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 It can be substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0066] For example, R1 may be further specified as hydrogen, deuterium, halogen, cyano group, or any one selected from the following structural formulas. However, it is not limited thereto.

[0067]

[0068]

[0069] In the above formula,

[0070] * indicates a portion connected to the above chemical formula 1. In addition, at least one substituent known in the art (e.g., identical to the R5 definition) that is not indicated in the aforementioned structural formula may be substituted.

[0071] In the compound represented by Formula 1 according to the present invention, the other side of the nitrogen-containing heteroaromatic ring (e.g., a ring containing azine or X) essentially includes a plurality of aryl groups, such as a naphthalene group and an aryl group (e.g., an aromatic ring containing R3 to R4). Additionally, an aryl group (e.g., an aromatic ring containing R2) may be further included between the nitrogen-containing heteroaromatic ring (e.g., a ring containing azine or X) and the dibenzo moiety (e.g., a ring containing Y).

[0072] The number of such aryl groups (e.g., aromatic rings), for example, l is an integer from 0 to 4, m is an integer from 1 to 4, and n is an integer from 1 to 7. For example, if l is 0, it is a direct bond, and if l is 1 to 4, it can have that number of aromatic rings. The same applies to m and n.

[0073] In addition, R2 to R4 introduced into the aromatic ring are identical or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, or may form a condensed ring by combining with any adjacent group (e.g., R3 to R4).

[0074] Here, the number of substituents of R2 to R4, e.g., b and c, are integers from 0 to 4, and d is an integer from 0 to 5. Here, if b is 0, R2 is hydrogen, and if b is 1 to 4, it may have the aforementioned substituents excluding hydrogen. Also, if b is 2 to 4, multiple R2s may be identical or different from each other. Also, the same may apply to R3 to R4.

[0075] Specifically, R2 to R4 are identical or different from one another, and each independently contains hydrogen, deuterium (D), halogen, cyano group, hydrogen, deuterium C1~C 30 alkyl group of, C3~C 30 cycloalkyl group of, C6~C 30 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclei, or combined with any adjacent group to form a condensation ring, wherein the alkyl group, cycloalkyl group, aryl group, and heteroaryl group are each independently deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei. More specifically, R2 to R4 may be applied in the same way as the specific moiety of R1 described above.

[0076] Meanwhile, the naphthalene group introduced as a plurality of aryl groups in the present invention has a structure in which it is bonded to a specific position described below when bonded to an R3-containing ring and an R4-containing ring, respectively. By controlling the bonding positions between the naphthalene group and the aryl group (e.g., phenyl group), the steric hindrance of the compound can be maximized.

[0077] For example, when the naphthalene group is combined with an R3-containing ring and an R4-containing ring, it is combined with any one of the structural formulas represented by A1 to A10 below.

[0078]

[0079] In the above formula,

[0080] * indicates a site that combines with the R3-containing ring and the R4-containing ring of the above chemical formula 1.

[0081] In the aforementioned Chemical Formula 1, 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, arylamine group, arylheteroarylamine group, heteroarylamine group, and condensation ring of Ar1 and R1 to R5 are each independently deuterium (D), halogen, cyano group, nitro group, C1 to C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, and in the case where there are multiple substituents, they may be identical or different from each other.

[0082] For example, in one embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 2 to 5 below, depending on the type of nitrogen-containing heteroaromatic ring (e.g., X-containing ring). However, it is not limited thereto.

[0083] [Chemical Formula 2]

[0084]

[0085] [Chemical Formula 3]

[0086]

[0087] [Chemical Formula 4]

[0088]

[0089] [Chemical Formula 5]

[0090]

[0091] In the above formula,

[0092] Y, Ar1, R1~R4, a~d, and l~n are each defined in Chemical Formula 1.

[0093] In another embodiment of the present invention, the compound represented by Formula 1 may be further specified by Formula 6 or Formula 7 below, depending on the type of dibenzo moiety (e.g., Y-containing ring). However, it is not limited thereto.

[0094] [Chemical Formula 6]

[0095]

[0096] [Chemical Formula 7]

[0097]

[0098] In the above formula,

[0099] X, Ar1, R1~R4, a~d, and l~n are each defined in Chemical Formula 1.

[0100] In another embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 8 to 11 below, depending on the bonding position of a dibenzo moiety (e.g., a Y-containing ring) connected to a nitrogen-containing heteroaromatic ring (e.g., an X-containing ring). However, it is not limited thereto.

[0101] [Chemical Formula 8]

[0102]

[0103] [Chemical Formula 9]

[0104]

[0105] [Chemical Formula 10]

[0106]

[0107] [Chemical Formula 11]

[0108]

[0109] In the above formula,

[0110] X, Y, Ar1, R1~R4, a~d, and l~n are each defined in Chemical Formula 1.

[0111] In another embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 12 to 23 below, depending on the number and bonding position of R1 groups bonded to a dibenzo moiety (e.g., a Y-containing ring). However, it is not limited thereto.

[0112] [Chemical Formula 12]

[0113]

[0114] [Chemical Formula 13]

[0115]

[0116] [Chemical Formula 14]

[0117]

[0118] [Chemical Formula 15]

[0119]

[0120] [Chemical Formula 16]

[0121]

[0122] [Chemical Formula 17]

[0123]

[0124] [Chemical Formula 18]

[0125]

[0126] [Chemical Formula 19]

[0127]

[0128] [Chemical Formula 20]

[0129]

[0130] [Chemical Formula 21]

[0131]

[0132] [Chemical Formula 22]

[0133]

[0134] [Chemical Formula 23]

[0135]

[0136] In the above formula,

[0137] X, Y, Ar1, R1~R4, b~d, and l~n are each as defined in Chemical Formula 1, and

[0138] If there are multiple R1s, the multiple R1s may be identical or different from each other.

[0139] In another embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 24 to 26 below, depending on the bonding position with a nitrogen-containing heteroaromatic ring (e.g., an X-containing ring), a phenyl ring, and an R3-containing ring. However, it is not limited thereto.

[0140] [Chemical Formula 24]

[0141]

[0142] [Chemical Formula 25]

[0143]

[0144] [Chemical Formula 26]

[0145]

[0146] In the above formula,

[0147] X, Y, Ar1, R1~R4, a~d, and l~n are each defined in Chemical Formula 1.

[0148] In another embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 27 to 36 below, depending on the bonding positions with the R3-containing ring, the naphthalene group, and the R4-containing ring. However, it is not limited thereto.

[0149] [Chemical Formula 27]

[0150]

[0151] [Chemical Formula 28]

[0152]

[0153] [Chemical Formula 29]

[0154]

[0155] [Chemical Formula 30]

[0156]

[0157] [Chemical Formula 31]

[0158]

[0159] [Chemical Formula 32]

[0160]

[0161] [Chemical Formula 33]

[0162]

[0163] [Chemical Formula 34]

[0164]

[0165] [Chemical Formula 35]

[0166]

[0167] [Chemical Formula 36]

[0168]

[0169] In the above formula,

[0170] X, Y, Ar1, R1~R4, a~d, and l~n are each defined in Chemical Formula 1.

[0171] In the case of the above chemical formula 36, ​​where the bonding position of the naphthalene group is connected to A-10, R1 may have a non-hydrogen substituent (e.g., a is 1 or more), Ar1 may have a heteroaryl group, R4 may have a non-hydrogen substituent (e.g., d is 1 or more), or at least two of the above configurations may be combined.

[0172] Meanwhile, compared to a structure in which specific bonds (e.g., ortho bonds) within the molecular structure of a compound are repeated continuously, if other bonding positions (e.g., meta / para bonds) are additionally included, a more planar structure can be realized structurally, and stacking is well achieved, allowing mobility properties to be easily controlled. Accordingly, in the case of Chemical Formula 36, ​​in addition to the A10 structure in which the R3 and R4-containing ring and the naphthalene group are connected by an ortho bond, it is preferable to include at least one additional bond with an aryl(lene) group having meta and / or para bonds (e.g., a phenylene linker or a phenyl group). Furthermore, in the case of Chemical Formula 36, ​​a structure in which two or more ortho bonds including the aforementioned A10 structure are repeated continuously is not included.

[0173] In another embodiment of the present invention, the compound represented by Formula 1 may be further specified as any one of Formulas 37 to 43 below, depending on the number and bonding position of R4s bonded to the R4-containing ring. However, it is not limited thereto.

[0174] [Chemical Formula 37]

[0175]

[0176] [Chemical Formula 38]

[0177]

[0178] [Chemical Formula 39]

[0179]

[0180] [Chemical Formula 40]

[0181]

[0182] [Chemical Formula 41]

[0183]

[0184] [Chemical Formula 42]

[0185]

[0186] [Chemical Formula 43]

[0187]

[0188] In the above formula,

[0189] X, Y, Ar1, R1~R4, a~c, and l~n are each as defined in Chemical Formula 1, and

[0190] If there are multiple R4s, the multiple R4s may be identical or different from each other.

[0191] The compound represented by Formula 1 according to the present invention described above may be further embodied as a compound represented by any one of the compounds 1 to 228 exemplified below. However, the compound represented by Formula 1 of the present invention is not limited to those exemplified below.

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202] In the present invention, "number of nuclei" refers to the number of ring atoms constituting a ring structure, and said nuclei may be carbon or heteroatoms selected from the group consisting of N, O, S, and Se. For example, the number of nuclei of pyridine refers to 6, including 5 C and 1 N constituting the pyridine ring.

[0203] In the present invention, "alkyl" refers to a monovalent substituent derived from a straight-chain or side-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0204] In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

[0205] In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0206] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms, consisting of a single ring or a combination of two or more rings. Additionally, forms in which two or more rings are simply attached (penant) or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthalene, phenanthrile, and anthryl.

[0207] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclei. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Additionally, forms in which two or more rings are simply pendent or condensed with each other may be included, and furthermore, forms condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl.

[0208] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenyloxy, naphthaleneoxy, diphenyloxy, etc., but are not limited thereto.

[0209] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' represents an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, etc.

[0210] In the present invention, "arylamine" means an amine substituted with an aryl group having 6 to 40 carbon atoms.

[0211] In the present invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0212] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclei, wherein one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Examples of such heterocycloalkyls include, but are not limited to, morpholine and piperazine.

[0213] In the present invention, "alkylsilyl" means a silyl substituted with an alkyl group having 1 to 40 carbon atoms, and "arylsilyl" means a silyl substituted with an aryl group having 5 to 40 carbon atoms.

[0214] In the present invention, "condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

[0215]

[0216] Electron Transport Layer Material

[0217] The present invention provides an electron transport layer comprising a compound represented by the above chemical formula 1.

[0218] The electron transport layer (ETL) described above serves to move electrons injected from the cathode to an adjacent layer, specifically the light-emitting layer.

[0219] The compound represented by the above chemical formula 1 may be used alone as an electron transport layer (ETL) material, or may be used in combination with electron transport layer materials known in the art. Preferably, it is used alone.

[0220] The electron transport layer material that can be mixed with the compound of Formula 1 above includes electron transport materials commonly known in the art. Non-limiting examples of usable electron transport materials include oxazole compounds, isooxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes (e.g., Alq3 (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These may be used individually or in combination of two or more types.

[0221] In the present invention, when the compound of Formula 1 and the electron transport layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0222]

[0223] Electron Transport Auxiliary Layer Material

[0224] In addition, the present invention provides an electron transport assisting layer comprising a compound represented by the above chemical formula 1.

[0225] The above electron transport auxiliary layer is positioned between the light-emitting layer and the electron transport layer and serves to prevent excitons or holes generated in the light-emitting layer from diffusing into the electron transport layer.

[0226] The compound represented by the above chemical formula 1 may be used alone as an electron transport auxiliary layer material, or may be used in combination with electron transport auxiliary layer materials known in the art. Preferably, it is used alone.

[0227] The electron transport auxiliary layer material that can be mixed with the compound of Chemical Formula 1 above includes electron transport materials commonly known in the art. For example, the electron transport auxiliary layer may include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), nitrogen-containing heterocyclic derivatives, etc.

[0228] In the present invention, when the compound of Formula 1 and the electron transport assisting layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0229]

[0230] Organic Electroluminescent Device

[0231] Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising a compound represented by Formula 1 according to the present invention described above.

[0232] Specifically, the present invention relates to an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by Chemical Formula 1. In this case, the compound may be used alone or in a mixture of two or more types.

[0233] The above one or more organic layers may be one or more of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a lifespan improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of the organic layers comprises a compound represented by Chemical Formula 1. Specifically, the organic layer comprising the compound of Chemical Formula 1 may be a light-emitting layer, a light-emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and / or a lifespan improvement layer, and more specifically, it is preferably an electron transport layer or an electron transport auxiliary layer.

[0234] The light-emitting layer of the organic electroluminescent device according to the present invention comprises a host material and a dopant material, wherein the host material may include a compound of Formula 1. In addition, the light-emitting layer of the present invention may include a compound known in the art other than the compound of Formula 1 as a host.

[0235] When the compound represented by Chemical Formula 1 above is included as a material for the light-emitting layer of an organic electroluminescent device, preferably as a blue, green, or red phosphorescent host material, the binding force between holes and electrons in the light-emitting layer is increased, thereby improving the efficiency (luminous efficiency and power efficiency), lifespan, brightness, and driving voltage of the organic electroluminescent device. Specifically, it is preferable that the compound represented by Chemical Formula 1 above be included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, it is preferable that the compound represented by Chemical Formula 1 of the present invention be a green phosphorescent exciplex N-type host material for the light-emitting layer having high efficiency.

[0236] The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, one or more of the hole injection layer, the hole transport layer, the light-emitting auxiliary layer, the light-emitting layer, the electron transport layer, and the electron injection layer may include a compound represented by Chemical Formula 1, and preferably, the light-emitting layer, more preferably, the phosphorescent host may include a compound represented by Chemical Formula 1. Meanwhile, an electron injection layer may be additionally stacked on the electron transport layer.

[0237] The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0238] The organic electroluminescent device of the present invention can be manufactured by forming an organic layer and an electrode using materials and methods known in the art, except that one or more of the aforementioned organic layers comprise a compound represented by Chemical Formula 1.

[0239] The above organic layer can be formed by vacuum deposition or solution coating. Examples of the above solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

[0240] The substrate used in the manufacture of the organic electroluminescent device of the present invention is not particularly limited, and examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

[0241] In addition, the anode material may be any anode material known in the art without limitation. Examples include metals or alloys thereof such as vanadium, chromium, copper, zinc, and gold; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited thereto.

[0242] In addition, the cathode material may be any cathode material known in the art without limitation. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer structural materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0243] In addition, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not specifically limited, and ordinary materials known in the industry may be used without restriction.

[0244]

[0245] The present invention will be described in detail below through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.

[0246]

[0247] [Preparation Examples 1 ~ 10]

[0248] [Preparation Example 1] Synthesis of Compound Core 1

[0249]

[0250] 2-chloro-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (100.0 g, 331.0 mmol), dibenzo[b,d]furan-2-ylboronic acid (73.7 g, 347.5 mmol), Pd(PPh3)4 (19.1 g, 16.5 mmol), and K2CO3 (91.5 g, 661.9 mmol) were added to a mixed solvent of 800 ml of THF and 200 ml of H2O and reacted for 3 hours under heating and reflux stirring. After the reaction was complete, the compounds were inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound Core 1 (116.7 g, yield 81.3%).

[0251] Mass: [(M+H)+] : 433

[0252]

[0253] [Preparation Example 2] Synthesis of Compound Core 2

[0254]

[0255] Compound Core 2 (114.7 g, yield 79.8%) was obtained by the same method as Preparation Example 1 above, except that 4-chloro-6-(3-chlorophenyl)-2-phenylpyrimidine was used instead of compound 2-chloro-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine.

[0256] Mass: [(M+H)+] : 432

[0257]

[0258] [Preparation Example 3] Synthesis of Core 3

[0259]

[0260] Compound Core 3 (109.0 g, yield 76.1%) was obtained in the same manner as Preparation Example 1 above, except that 2-chloro-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine was used instead of compound 2-chloro-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine.

[0261] Mass: [(M+H)+] : 433

[0262]

[0263] [Preparation Example 4] Synthesis of Core 4

[0264]

[0265] Compound Core 4 (119.0 g, yield 70.5%) was obtained by the same method as Preparation Example 1 above, except that (3-(dibenzo[b,d]furan-2-yl)phenyl)boronic acid was used instead of compound dibenzo[b,d]furan-2-ylboronic acid.

[0266] Mass: [(M+H)+] : 509

[0267]

[0268] [Preparation Example 5] Synthesis of Core 5

[0269]

[0270] Compound Core 5 (106.6 g, yield 74.2%) was obtained by the same method as Preparation Example 1 above, except that dibenzo[b,d]furan-4-ylboronic acid was used instead of compound dibenzo[b,d]furan-2-ylboronic acid.

[0271] Mass: [(M+H)+] : 433

[0272]

[0273] [Preparation Example 6] Synthesis of Core 6

[0274]

[0275] Compound Core 6 (133.3g, yield 78.9%) was obtained by performing the same procedure as in Preparation Example 1, except that 4-chloro-6-(4-chlorophenyl)-2-phenylpyrimidine (100g, 332mmol) and (6-phenyldibenzo[b,d]furan-2-yl)boronic acid (100.4g, 348.6mmol) were used instead of the substances used in Preparation Example 1.

[0276] Mass: [(M+H)+] : 508

[0277]

[0278] [Preparation Example 7] Synthesis of Core 7

[0279]

[0280] Compound Core 7 (104.3g, yield 61.7%) was obtained by performing the same procedure as in Preparation Example 1, except that 4-chloro-6-(2-chlorophenyl)-2-phenylpyrimidine (100g, 332mmol) and (6-phenyldibenzo[b,d]furan-2-yl)boronic acid (100.4g, 348.6mmol) were used instead of the substances used in Preparation Example 1.

[0281] Mass: [(M+H)+] : 508

[0282]

[0283] [Preparation Example 8] Synthesis of Core 8

[0284]

[0285] Compound Core 8 (114.0 g, yield 67.5%) was obtained by the same method as in Preparation Example 1 above, except that (9-phenyldibenzo[b,d]-furan-2-yl)boronic acid was used instead of compound dibenzo[b,d]furan-2-ylboronic acid.

[0286] Mass: [(M+H)+] : 509

[0287]

[0288] [Preparation Example 9] Synthesis of Core 9

[0289]

[0290] Compound Core 9 (123.8 g, yield 63.8%) was obtained by the same method as in Preparation Example 1 above, except that (5-(dibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid was used instead of compound dibenzo[b,d]furan-2-ylboronic acid.

[0291] Mass: [(M+H)+] : 585

[0292]

[0293] [Preparation Example 10] Synthesis of Core 10

[0294]

[0295] Compound Core 10 (122.5 g, yield 60.6%) was obtained by the same method as in Preparation Example 1 above, except that (4'-cyano-5-(dibenzo [b,d]furan-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid was used instead of compound dibenzo[b,d]furan-2-ylboronic acid.

[0296] Mass: [(M+H)+] : 610

[0297]

[0298] [Synthesized Examples 1 ~ 25]

[0299] [Synthesization Example 1] Synthesis of Compound 1

[0300]

[0301] Core 1 (10.0 g, 23.0 mmol), 4,4,5,5-tetramethyl-2-(2-(2-phenylnaphthalen-1-yl)phenyl)-1,3,2-dioxaborolane (10.3 g, 25.4 mmol), Pd(OAc)2 (0.2 g, 0.7 mmol), X-phos (0.7 g, 1.4 mmol), and Cs2CO3 (15.0 g, 46.1 mmol) were added to a mixed solvent of 80 ml of dioxane and 20 ml of H2O and reacted for 3 hours under heating and reflux stirring. After the reaction was complete, the compounds were inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain Compound 1 (9.9 g, yield 63.5%).

[0302] Mass: [(M+H)+] : 677

[0303]

[0304] [Synthesization Example 2] Synthesis of Compound 4

[0305]

[0306] Core 1 (10.0 g, 23.0 mmol), 4,4,5,5-tetramethyl-2-(2-(4-phenylnaphthalen-2-yl)phenyl)-1,3,2-dioxaborolane (10.3 g, 25.4 mmol), Pd(OAc)2 (0.2 g, 0.7 mmol), X-phos (0.7 g, 1.4 mmol), and Cs2CO3 (15.0 g, 46.1 mmol) were added to a mixed solvent of 80 ml of dioxane and 20 ml of H2O and reacted for 3 hours under heating and reflux stirring. After the reaction was complete, the compounds were inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain Compound 4 (8.7 g, yield 56.1%).

[0307] Mass: [(M+H)+] : 677

[0308]

[0309] [Synthesization Example 3] Synthesis of Compound 31

[0310]

[0311] Core 2 (10.0 g, 23.1 mmol), 4,4,5,5-tetramethyl-2-(2-(2-phenylnaphthalen-1-yl)phenyl)-1,3,2-dioxaborolane (10.3 g, 25.4 mmol), Pd(OAc)2 (0.2 g, 0.7 mmol), X-phos (0.7 g, 1.4 mmol), and Cs2CO3 (15.1 g, 46.2 mmol) were added to a mixed solvent of 80 ml of dioxane and 20 ml of H2O and reacted for 3 hours under heating and reflux stirring. After the reaction was complete, the compounds were inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain Compound 31 (8.7 g, yield 55.9%).

[0312] Mass: [(M+H)+] : 676

[0313]

[0314] [Synthesization Example 4] Synthesis of Compound 38

[0315]

[0316] Core 2 (10.0 g, 23.1 mmol), 4,4,5,5-tetramethyl-2-(2-(7-phenylnaphthalen-1-yl)phenyl)-1,3,2-dioxaborolane (10.3 g, 25.4 mmol), Pd(OAc)2 (0.2 g, 0.7 mmol), X-phos (0.7 g, 1.4 mmol), and Cs2CO3 (15.1 g, 46.2 mmol) were added to a mixed solvent of 80 ml of dioxane and 20 ml of H2O and reacted for 3 hours under heating and reflux stirring. After the reaction was complete, the compounds were inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain Compound 38 (7.5 g, yield 47.8%).

[0317] Mass: [(M+H)+] : 676

[0318]

[0319] [Synthesization Example 5] Synthesis of Compound 68

[0320]

[0321] Core 3 (10.0 g, 23.0 mmol), 4,4,5,5-tetramethyl-2-(2-(7-phenylnaphthalen-1-yl)phenyl)-1,3,2-dioxaborolane (10.3 g, 25.4 mmol), Pd(OAc)2 (0.2 g, 0.7 mmol), X-phos (0.7 g, 1.4 mmol), and Cs2CO3 (15.0 g, 46.1 mmol) were added to a mixed solvent of 80 ml of dioxane and 20 ml of H2O and reacted for 3 hours under heating and reflux stirring. After the reaction was complete, the mixture was inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 68 (11.3 g, yield 72.2%).

[0322] Mass: [(M+H)+] : 676

[0323]

[0324] [Synthesization Example 6] Synthesis of Compound 70

[0325]

[0326] Core 3 (10.0 g, 23.0 mmol), 4,4,5,5-tetramethyl-2-(2-(7-phenylnaphthalen-2-yl)phenyl)-1,3,2-dioxaborolane (10.3 g, 25.4 mmol), Pd(OAc)2 (0.2 g, 0.7 mmol), X-phos (0.7 g, 1.4 mmol), and Cs2CO3 (15.0 g, 46.1 mmol) were added to a mixed solvent of 80 ml of dioxane and 20 ml of H2O and reacted for 3 hours under heating and reflux stirring. After the reaction was complete, the compounds were inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain Compound 70 (11.8 g, yield 75.4%).

[0327] Mass: [(M+H)+] : 677

[0328]

[0329] [Synthesization Example 7] Synthesis of Compound 97

[0330]

[0331] Compounds Core4 (10.0 g, 19.6 mmol) and 4,4,5,5-tetramethyl-2-(2-(8-phenylnaphthalen-1-yl)phenyl)-1,3,2-dioxaborolane (8.8 g, 21.6 mmol) of [Preparation Example 4] were each

[0332] Compound 97 (9.0g, yield 61.3%) was obtained by the same method as Synthesis Example 1 above, except for the use of the above compound.

[0333] Mass: [(M+H)+] : 753

[0334]

[0335] [Synthesization Example 8] Synthesis of Compound 98

[0336]

[0337] Compound Core 4 (10.0 g, 19.6 mmol) and 4,4,5,5-tetramethyl-2-(3-(5-phenylnaphthalen-1-yl)phenyl)-1,3,2-dioxaborolane (8.8 g, 21.6 mmol) of [Preparation Example 4] were each

[0338] Compound 98 (8.6g, yield 57.9%) was obtained by the same method as Synthesis Example 1 above, except for what was used.

[0339] Mass: [(M+H)+] : 753

[0340]

[0341] [Synthesization Example 9] Synthesis of Compound 113

[0342]

[0343] Compound 113 (10.0 g, yield 64.4%) was obtained by the same method as Synthesis Example 1, except that Compound Core 5 (10.0 g, 23.0 mmol) and 4,4,5,5-tetramethyl-2-(2-(8-phenylnaphthalen-2-yl)phenyl)-1,3,2-dioxaborolane (10.3 g, 25.4 mmol) of [Preparation Example 5] were used, respectively.

[0344] Mass: [(M+H)+] : 677

[0345]

[0346] [Synthesization Example 10] Synthesis of Compound 114

[0347]

[0348] Compound 114 (8.7g, yield 55.5%) was obtained by the same method as Synthesis Example 1, except that Compound Core 5 (10.0g, 23.0mmol) and 4,4,5,5-tetramethyl-2-(2-(1-phenylnaphthalen-2-yl)phenyl)-1,3,2-dioxaborolane (10.3g, 25.4mmol) of [Preparation Example 5] were used, respectively.

[0349] Mass: [(M+H)+] : 677

[0350]

[0351] [Synthesization Example 11] Synthesis of Compound 151

[0352]

[0353] Compound 151 (7.8g, yield 52.7%) was obtained by the same method as Synthesis Example 1, except that Compound Core 6 (10.0g, 19.6mmol) and 4,4,5,5-tetramethyl-2-(2-(8-phenylnaphthalen-1-yl)phenyl)-1,3,2-dioxaborolane (8.8g, 21.6mmol) of [Preparation Example 6] were used, respectively.

[0354] Mass: [(M+H)+] : 752

[0355]

[0356] [Synthesization Example 12] Synthesis of Compound 153

[0357]

[0358] Compound 153 (7.1g, yield 48.3%) was obtained by the same method as Synthesis Example 1, except that Compound Core 7 (10.0g, 19.6mmol) and 4,4,5,5-tetramethyl-2-(2-(1-phenylnaphthalen-2-yl)phenyl)-1,3,2-dioxaborolane (8.8g, 21.6mmol) of [Preparation Example 7] were used, respectively.

[0359] Mass: [(M+H)+] : 752

[0360]

[0361] [Synthesization Example 13] Synthesis of Compound 166

[0362]

[0363] Compound 166 (7.8g, yield 52.9%) was obtained by the same method as Synthesis Example 1, except that Compound Core 8 (10.0g, 19.6mmol) and 4,4,5,5-tetramethyl-2-(2-(7-phenylnaphthalen-1-yl)phenyl)-1,3,2-dioxaborolane (8.8g, 21.6mmol) of [Preparation Example 8] were used, respectively.

[0364] Mass: [(M+H)+] : 753

[0365]

[0366] [Synthesization Example 14] Synthesis of Compound 169

[0367]

[0368] Compound 169 (7.0g, yield 47.6%) was obtained by the same method as Synthesis Example 1, except that Compound Core 8 (10.0g, 19.6mmol) and 4,4,5,5-tetramethyl-2-(2-(6-phenylnaphthalen-1-yl)phenyl)-1,3,2-dioxaborolane (8.8g, 21.6mmol) of [Preparation Example 8] were used, respectively.

[0369] Mass: [(M+H)+] : 753

[0370]

[0371] [Synthesization Example 15] Synthesis of Compound 170

[0372]

[0373] Compound 170 (6.8g, yield 48.2%) was obtained by the same method as Synthesis Example 1, except that Compound Core 9 (10.0g, 17.1mmol) and 4,4,5,5-tetramethyl-2-(2-(8-phenylnaphthalen-1-yl)phenyl)-1,3,2-dioxaborolane (7.6g, 18.8mmol) of [Preparation Example 9] were used, respectively.

[0374] Mass: [(M+H)+] : 829

[0375]

[0376] [Synthesization Example 16] Synthesis of Compound 171

[0377]

[0378] Compound 171 (6.1g, yield 43.4%) was obtained by the same method as Synthesis Example 1, except that Compound Core 9 (10.0g, 17.1mmol) and 4,4,5,5-tetramethyl-2-(2-(5-phenylnaphthalen-1-yl)phenyl)-1,3,2-dioxaborolane (7.6g, 18.8mmol) of [Preparation Example 9] were used, respectively.

[0379] Mass: [(M+H)+] : 829

[0380]

[0381] [Synthesization Example 17] Synthesis of Compound 176

[0382]

[0383] Compound 176 (5.6g, yield 39.8%) was obtained by the same method as Synthesis Example 1, except that Compound Core 10 (10.0g, 16.4mmol) and 4,4,5,5-tetramethyl-2-(2-(8-phenylnaphthalen-1-yl)phenyl)-1,3,2-dioxaborolane (7.3g, 18.0mmol) of [Preparation Example 10] were used, respectively.

[0384] Mass: [(M+H)+] : 854

[0385]

[0386] [Synthesizing Example 18] Synthesis of Compound 179

[0387]

[0388] Compound 179 (11.3g, yield 65.2%) was obtained by the same method as in Synthesis Example 1, except that Compound Core 2 (10.0g, 23.1mmol) and 4,4,5,5-tetramethyl-2-(5-(3-phenylnaphthalen-1-yl)-[1,1'-biphenyl]-3-yl)-1,3,2-dioxaborolane (12.3g, 25.4mmol) of [Preparation Example 2] were used, respectively.

[0389] Mass: [(M+H)+] : 752

[0390]

[0391] [Synthesization Example 19] Synthesis of Compound 183

[0392]

[0393] Compound 183 (10.6g, yield 63.4%) was obtained by the same method as in Synthesis Example 1, except that Compound Core 2 (10.0g, 23.1mmol) and 4,4,5,5-tetramethyl-2-(3'-phenyl-[1,1'-binaphthalen]-3-yl)-1,3,2-dioxaborolane (11.6g, 25.4mmol) of [Preparation Example 2] were used, respectively.

[0394] Mass: [(M+H)+] : 726

[0395]

[0396] [Synthesization Example 20] Synthesis of Compound 184

[0397]

[0398] Compound 184 (9.6g, yield 53.3%) was obtained by the same method as in Synthesis Example 1, except that Compound Core 2 (10.0g, 23.1mmol) and 3'-(3-phenylnaphthalen-1-yl)-5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbonitrile (12.9g, 25.4mmol) of [Preparation Example 2] were used, respectively.

[0399] Mass: [(M+H)+] : 777

[0400]

[0401] [Synthesization Example 21] Synthesis of Compound 185

[0402]

[0403] Compound 185 (10.6g, yield 50.6%) was obtained by the same method as in Synthesis Example 1, except that Compound Core 2 (10.0g, 23.1mmol) of [Preparation Example 2] and 2,4-diphenyl-6-(3-(3-phenylnaphthalen-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phe-nyl)-1,3,5-triazine (16.2g, 25.4mmol) were used, respectively.

[0404] Mass: [(M+H)+] : 907

[0405]

[0406] [Synthesization Example 22] Synthesis of Compound 186

[0407]

[0408] Compound 186 (10.4g, yield 59.6%) was obtained by the same method as in Synthesis Example 1, except that Compound Core 2 (10.0g, 23.1mmol) of [Preparation Example 2] and 2-(3-(3-([1,1'-biphenyl]-2-yl)naphthalen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (12.3g, 25.4mmol) were used, respectively.

[0409] Mass: [(M+H)+] : 752

[0410]

[0411] [Synthesization Example 23] Synthesis of Compound 187

[0412]

[0413] Compound 187 (10.7g, yield 61.7%) was obtained by the same method as Synthesis Example 1, except that Compound Core 1 (10.0g, 23.0mmol) of [Preparation Example 1] and 2-(2-(2-([1,1'-biphenyl]-4-yl)naphthalen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (12.2g, 25.4mmol) were used respectively.

[0414] Mass: [(M+H)+] : 753

[0415]

[0416] [Synthesization Example 24] Synthesis of Compound 188

[0417]

[0418] Compound 188 (9.4g, yield 52.5%) was obtained by the same method as in Synthesis Example 1, except that Compound Core 1 (10.0g, 23.0mmol) and 3'-(1-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)naphthalen-2-yl)-[1,1'-biphenyl]-4-carbonitrile (12.9g, 25.4mmol) of [Preparation Example 1] were used, respectively.

[0419] Mass: [(M+H)+] : 778

[0420]

[0421] [Synthesization Example 25] Synthesis of Compound 189

[0422]

[0423] Compound 189 (8.7g, yield 48.8%) was obtained by the same method as in Synthesis Example 1, except that Compound Core 3 (10.0g, 23.0mmol) of [Preparation Example 3] and 3'-(2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)naphthalen-1-yl)-[1,1'-biphe-nyl]-4-carbonitrile (12.9g, 25.4mmol) were used, respectively.

[0424] Mass: [(M+H)+] : 778

[0425]

[0426] [Example 1] Fabrication of a blue organic electroluminescent device (electron transport layer)

[0427] After purifying the compound synthesized in the above synthesis example to high purity through sublimation using a commonly known method, a blue organic electroluminescent device was fabricated according to the following process.

[0428] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0429] An organic electroluminescent device was fabricated by stacking HI + 2% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / BH + 2% BD (20 nm) / compound 176 (electron transport layer material) + Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm) in that order on the ITO transparent electrode prepared as above.

[0430]

[0431] [Examples 2-5] Fabrication of a blue organic electroluminescent device (electron transport layer)

[0432] A blue organic electroluminescent device was fabricated by performing the same procedure as Example 1 above, except that the electron transport layer material of Table 1 below was used instead of Compound 176 as the electron transport layer material.

[0433]

[0434] [Comparative Examples 1 to 5] Preparation of Blue Organic Electroluminescent Devices

[0435] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that Alq3, DC-1 to 4 were used instead of Compound 176 as the electron transport layer material.

[0436] The structures of compounds HI, HAT-CN6, EB, BH, BD, Liq, Alq3, DC-1 to DC-4 used in the above examples and comparative examples are as follows.

[0437]

[0438]

[0439]

[0440] [Evaluation Example 1]

[0441] For the organic electroluminescent devices prepared in Examples 1 to 5 and Comparative Examples 1 to 5, respectively, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm² were measured, and the results are shown in Table 1 below.

[0442] Sample Electron Transport Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 1 Compound 1763.54568.0 Example 2 Compound 1843.44548.2 Example 3 Compound 1853.24558.1 Example 4 Compound 1883.64567.9 Example 5 Compound 1893.34558.3 Comparative Example 1 Alq3 4.64565.5 Comparative Example 2 DC-1 4.34586.7 Comparative Example 3 DC-2 4.14556.8 Comparative Example 4 DC-3 4.24576.9 Comparative Example 5 DC-4 4.24576.6

[0443] As shown in Table 1 above, it was confirmed that the blue organic electroluminescent device of Examples 1 to 5, which uses a compound according to the present invention as an electron transport layer material, is superior in terms of driving voltage, emission peak, and current efficiency compared to Comparative Example 1, which uses conventional Alq3 as an electron transport layer material; and Comparative Examples 2 to 5, which use a compound not containing the composition of the present invention as an electron transport layer material.

[0444]

[0445] [Examples 6 to 25] Fabrication of blue organic electroluminescent devices (electron transport auxiliary layer)

[0446] After purifying the compound synthesized in the above synthesis example to high purity through sublimation using a commonly known method, a blue organic electroluminescent device was fabricated according to the following process.

[0447] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0448] An organic electroluminescent device was fabricated by stacking HI + 2% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / BH + 2% BD (20 nm) / electron transport auxiliary layer material of Table 2 below (5 nm) / ET + Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm) in that order on the ITO transparent electrode prepared as above.

[0449] The structure of the compound ET used at this time is as follows.

[0450]

[0451]

[0452] [Comparative Example 6]

[0453] A blue organic electroluminescent device of Comparative Example 6 was fabricated by performing the same procedure as in Example 6, except that an electron transport layer of 35 nm was deposited without using an electron transport auxiliary layer material.

[0454]

[0455] [Comparative Examples 7 to 10] Preparation of blue organic electroluminescent devices

[0456] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 6, except that DC-1 to 4 were used instead of Compound 1 as the electron transport auxiliary layer material.

[0457]

[0458] [Evaluation Example 1]

[0459] For the organic electroluminescent devices prepared in Examples 6 to 25 and Comparative Examples 6 to 10, respectively, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm² were measured, and the results are shown in Table 2 below.

[0460] Sample Electron Transport Auxiliary Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 6 Compound 13.14548.1 Example 7 Compound 43.24558.2 Example 8 Compound 313.34558.1 Example 9 Compound 383.14548.1 Example 10 Compound 683.24558.1 Example 11 Compound 703.34548.2 Example 12 Compound 973.14558.1 Example 13 Compound 983.24548.2 Example 14 Compound 1133.24548.2 Example 15 Compound 1143.34558.1 Example 16 Compound 1513.34558.1 Example 17 Compound 1533.24548.1 Example 18 Compound 1663.34558.0 Example 19 Compound 1693.44548.1 Example 20 Compound 1703.24558.3 ​​Example 21 Compound 1713.34548.2 Example 22 Compound 1793.14558.1 Example 23 Compound 1833.14558.3 ​​Example 24 Compound 1863.14548.1 Example 25 Compound 1873.34548.2 Comparative Example 6-4.64566.3 Comparative Example 7DC-14.04566.9 Comparative Example 8DC-24.04567.1 Comparative Example 9DC-34.04566.9 Comparative Example 10DC-44.04567.0

[0461] As shown in Table 2 above, it was confirmed that the blue organic electroluminescent device of Examples 6 to 25, which uses a compound according to the present invention as an electron transport auxiliary layer material, is superior in terms of driving voltage, emission peak, and current efficiency compared to Comparative Example 6, which does not include an electron transport auxiliary layer; and Comparative Examples 7 to 10, which use a compound not containing the composition of the present invention as an electron transport auxiliary layer material.

Claims

1. Compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X are identical or different from each other, each independently being N or CR5, provided that at least two of the plurality of X are N, Ar1 is C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, Y is O or S, R1 to R5 are identical or different from one another, and each independently consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, or R1 to R4 may each combine with any adjacent group to form a condensation ring; l is an integer from 0 to 4, and m is an integer from 1 to 4, and n is an integer from 1 to 7, and a is an integer from 0 to 7, and b and c are integers from 0 to 4, respectively, and d is an integer from 0 to 5, 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, arylamine group, arylheteroarylamine group, heteroarylamine group, and condensation ring of the above Ar1 and R1 to R5 are each independently deuterium (D), halogen, cyano group, nitro group, C1 to C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, and in the case where there are multiple substituents, they may be identical or different from each other.

2. In Paragraph 1, The above X-containing ring is a compound selected from the group of substituents represented by the following chemical formula: In the above formula, * indicates the part connected to the above chemical formula 1, and Ar1, R2 and b are each as defined in Paragraph 1.

3. In Paragraph 1, Ar1 is C1~C 40 alkyl group of, C3~C 40 cycloalkyl group of, C6~C 60 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, The above alkyl group, cycloalkyl group, aryl group, and heteroaryl group are each independently deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 A compound that is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

4. In Paragraph 1, Ar1 is a compound selected from the following structural formulas: In the above formula, * indicates the part connected to the above chemical formula 1, and R 11 It consists of hydrogen, deuterium (D), and C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

5. In Paragraph 1, A compound in which, when the above naphthalene group is bonded to the above R3-containing ring and the above R4-containing ring, it is bonded to any one of the structural formulas represented by A1 to A10 below: In the above formula, * indicates a site that combines with the R3-containing ring and the R4-containing ring of the above chemical formula 1.

6. In Paragraph 1, R1 to R4 are identical or different from one another, and each independently hydrogen, deuterium (D), halogen, cyano group, hydrogen, deuterium, C1~C 30 alkyl group of, C3~C 30 cycloalkyl group of, C6~C 30 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclei, or combined with any adjacent group to form a condensation ring, The above alkyl group, cycloalkyl group, aryl group, and heteroaryl group are each independently deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 A compound that is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

7. In Paragraph 1, Compounds in which R1 to R4 are identical or different from each other, and each independently selected from hydrogen, deuterium, halogen, cyano group, or the following structural formulas: In the above formula, * indicates the part connected to the above chemical formula 1.

8. In Paragraph 1, The compound represented by Chemical Formula 1 above is a compound represented by Chemical Formulas 2 to 5 below: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] In the above formula, Y, Ar1, R1~R4, a~d, and l~n are each as defined in Paragraph 1.

9. In Paragraph 1, The compound represented by the above Chemical Formula 1 is a compound represented by the following Chemical Formula 6 or Chemical Formula 7: [Chemical Formula 6] [Chemical Formula 7] In the above formula, X, Ar1, R1~R4, a~d, and l~n are each as defined in Paragraph 1.

10. In Paragraph 1, The compound represented by Chemical Formula 1 above is a compound represented by Chemical Formulas 8 to 11 below: [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] In the above formula, X, Y, Ar1, R1~R4, a~d, and l~n are each as defined in Paragraph 1.

11. In Paragraph 1, The compound represented by the above Chemical Formula 1 is a compound represented by the following Chemical Formulas 12 to 23: [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 19] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] In the food, X, Y, Ar1, R1~R4, b~d, and l~n are each as defined in Paragraph 1, and If there are multiple R1s, the multiple R1s may be identical or different from each other.

12. In Paragraph 1, The compound represented by Chemical Formula 1 above is a compound represented by Chemical Formulas 24 to 26 below: [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 26] In the above formula, X, Y, Ar1, R1~R4, a~d, and l~n are each as defined in Paragraph 1.

13. In Paragraph 1, The compound represented by Chemical Formula 1 above is a compound represented by Chemical Formulas 27 to 36 below: [Chemical Formula 27] [Chemical Formula 28] [Chemical Formula 29] [Chemical Formula 30] [Chemical Formula 31] [Chemical Formula 32] [Chemical Formula 33] [Chemical Formula 34] [Chemical Formula 35] [Chemical Formula 36] In the above formula, X, Y, Ar1, R1~R4, a~d, and l~n are each as defined in Paragraph 1.

14. In Paragraph 1, The compound represented by the above Chemical Formula 1 is a compound represented by the following Chemical Formulas 37 to 43: [Chemical Formula 37] [Chemical Formula 38] [Chemical Formula 39] [Chemical Formula 40] [Chemical Formula 41] [Chemical Formula 42] [Chemical Formula 43] In the above formula, X, Y, Ar1, R1~R4, a~c, and l~n are each as defined in Paragraph 1, and If there are multiple R4s, the multiple R4s may be identical or different from each other.

15. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 1 to 228.

16. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound that is a material for a light-emitting layer, an electron transport layer, or an electron transport auxiliary layer.

17. An organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound described in any one of claims 1 to 16.

18. In Paragraph 17, An organic electroluminescent device in which the organic layer containing the above compound is selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a lifespan improvement layer, an electron transport layer, and an electron transport auxiliary layer.

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