Organic compound and organic electroluminescent element using same

Abstract

The present invention relates to: a novel compound having excellent carrier transport ability, light emission ability, and thermal stability; and an organic electroluminescent element having improved characteristics such as light emission efficiency, driving voltage, and lifespan by containing the compound in one or more organic material layers.

Description

Technical Field

[0001] The present invention relates to novel organic light-emitting compounds and organic electroluminescent devices using the same, and more particularly, to compounds having excellent electron transport ability and organic electroluminescent devices in which the characteristics such as luminous efficiency, driving voltage, and lifetime are improved by including the compounds in one or more organic layers. Background Art

[0002] In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when these excitons transition to the ground state, light is emitted. At this time, the materials used as the organic layer can be classified into a light-emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their functions.

[0003] The light-emitting materials can be classified into blue, green, red light-emitting materials and yellow and orange light-emitting materials for presenting more natural colors according to the emission color. In addition, in order to improve the luminous efficiency through an increase in color purity and energy transfer, a host / dopant system can be used as the light-emitting material.

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

[0005] So far, NPB, BCP, Alq3, etc. are widely known as hole injection layer, hole transport layer, hole blocking layer, and electron transport layer materials, and anthracene derivatives have been reported as light-emitting layer materials. In particular, metal coordination compounds containing Ir such as Firpic, Ir(ppy)3, (acac)Ir(btp)2, etc., which have advantages in terms of efficiency improvement in the light-emitting layer materials, have been used as phosphorescent dopant materials for blue, green, and red, and 4,4-dicarbazolybiphenyl (CBP) has been used as a phosphorescent host material.

[0006] However, although the conventional organic layer materials have advantages in terms of luminous characteristics, they have a low glass transition temperature and very poor thermal stability, and thus cannot reach a satisfactory level in terms of the lifetime of the organic electroluminescent device. Therefore, it is necessary to develop organic layer materials with excellent performance. Summary of the Invention

[0007] Technical problem

[0008] The technical problem of the present invention is to provide an organic layer material that has excellent heat resistance, carrier transport ability, light-emitting ability, etc. and can be used as an organic electroluminescent element, and specifically, a novel compound that can be used as an electron transport layer, an electron transport auxiliary layer, a light-emitting layer, etc.

[0009] In addition, another technical problem of the present invention is to provide an organic electroluminescent element that contains the above novel compound and has a low driving voltage, a high luminous efficiency, and an improved lifespan.

[0010] Other objects and advantages of the present invention will be more clearly described through the following detailed description of the invention and the scope of the claims.

[0011] Method for solving the problem

[0012] In order to achieve the above object, the present invention provides a compound represented by the following Chemical Formula 1.

[0013] [Chemical Formula 1]

[0014]

[0015] In the above Chemical Formula 1,

[0016] X1 to X3 are the same as or different from each other and are each independently C(R5) or N, provided that at least two of X1 to X3 are N,

[0017] Y1 and Y2 are the same as or different from each other and are each independently selected from the group consisting of O, S, and NR 11 provided that the case where Y1 and Y2 are both O is excluded,

[0018] Ar1 and Ar2 are the same as or different from each other and are each independently selected from the group consisting of C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C3-C 40 cycloalkyl, heterocycloalkyl having 3 to 40 nuclei, C6-C 60 aryl, heteroaryl having 5 to 60 nuclei, C1-C 40 alkoxy, C6-C 60 aryloxy, C3-C 40 alkylsilyl, C6-C 60 arylsilyl, C1-C 40 alkylboron, C6-C 60 arylboron, C6-C 60 arylphosphino, C6-C 60arylphosphine oxide group and C6-C 60 a group consisting of arylamino groups, or they may combine with any adjacent groups to form a condensed ring,

[0019] R1 to R5 and R 11 are the same as or different from each other, and each independently is selected from the group consisting of hydrogen, deuterium (D), halogen, cyano, nitro, C1-C 40 alkyl groups, C2-C 40 alkenyl groups, C2-C 40 alkynyl groups, C3-C 40 cycloalkyl groups, heterocycloalkyl groups having 3 to 40 ring atoms, C6-C 60 aryl groups, heteroaryl groups having 5 to 60 ring atoms, C1-C 40 alkoxy groups, C6-C 60 aryloxy groups, C3-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 a group consisting of arylamino groups, or they may combine with any adjacent groups to form a condensed ring,

[0020] o, p, and q can each independently be an integer from 0 to 4, and r is an integer from 0 to 3,

[0021] The above-mentioned Ar1 to Ar2, R1 to R5, and R 11 alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, aryloxy groups, alkoxy groups, cycloalkyl groups, heterocycloalkyl groups, alkylsilyl groups, arylsilyl groups, alkylboron groups, arylboron groups, arylphosphine groups, arylphosphine oxide groups, and arylamino groups can each independently be selected from the group consisting of deuterium (D), halogen, cyano, nitro, C1-C 40 alkyl groups, C2-C 40 alkenyl groups, C2-C 40 alkynyl groups, C3-C 40 cycloalkyl groups, heterocycloalkyl groups having 3 to 40 ring atoms, C6-C 60 aryl groups, heteroaryl groups having 5 to 60 ring atoms, C1-C 40 alkoxy 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-C60 is substituted with one or more substituents selected from the group consisting of an arylphosphino group, a C6-C 60 aryloxyphosphino group, and a C6-C 60 arylamino group, and when there are a plurality of the above substituents, they may be the same as or different from each other.

[0022] Further, the present invention provides an organic electroluminescent element including an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, and at least one of the one or more organic layers contains the compound represented by Chemical Formula 1 above.

[0023] Among them, the organic layer containing the compound represented by Chemical Formula 1 above 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. At this time, the compound represented by Chemical Formula 1 may be included as a material for at least one of a phosphorescent host material of the light-emitting layer, an electron transport layer, and an electron transport auxiliary layer.

[0024] Advantages of the Invention

[0025] According to an embodiment of the present invention, the compound represented by Chemical Formula 1 above has excellent electron transport ability, light-emitting ability, heat resistance, etc., and thus can be used as a material for the organic layer of an organic electroluminescent element.

[0026] In particular, when the compound represented by Chemical Formula 1 of the present invention is used as a material for an electron transport layer or an electron transport auxiliary layer, it can exhibit high thermal stability, low driving voltage, high mobility, high current efficiency, and long lifetime characteristics as compared with conventional host materials or electron transport materials.

[0027] Therefore, the organic electroluminescent element containing the compound represented by Chemical Formula 1 above can be greatly improved in terms of excellent light-emitting performance, low driving voltage, long lifetime, and high efficiency, and thus can be effectively used for full-color display panels and the like.

[0028] The effects of the present invention are not limited to the above-exemplified contents, and more diverse effects are included in this specification. Detailed Description of the Invention

[0029] Hereinafter, the present invention will be described in detail.

[0030] <Novel Organic Compound>

[0031] The present invention provides a novel compound having excellent thermal stability, carrier transport ability, light-emitting ability, etc., for example, a polycyclic spiro compound.

[0032] The compound represented by the above Chemical Formula 1 has a core having a polycyclic spiro bond structure containing at least two heteroatoms (e.g., S-S / O-S / S-NR’ / NR’-NR” / O-NR’), and the above core structure is directly bonded to an electron withdrawing group (EWG) having excellent electron transporting ability, thereby forming a basic skeleton.

[0033] Specifically, the compound of Chemical Formula 1 has an electron donating effect due to the lone pair electrons of the heteroatoms (O or S) contained in the polycyclic spiro-based core structure. Therefore, when such a compound is applied to an organic light emitting device, the light emitting efficiency of the device can be improved, and the durability and stability of the device can be enhanced to effectively extend the life of the device.

[0034] In addition, by introducing triazine or pyrimidine, which is an azine-based functional group having a strong electron withdrawing ability (electron withdrawing group, EWG), to increase the electron migration speed, physicochemical properties more suitable for electron injection and electron transport can be obtained. When the compound of Chemical Formula 1 is applied as a material for an electron transport layer or an electron transport assisting layer, electrons can be well received from the cathode and smoothly transferred to the light emitting layer, so that the driving voltage of the device can be reduced, leading to high efficiency and long life.

[0035] In particular, when an EWG (e.g., an azine group) is substituted on a ring such as N in the polycyclic spiro-based core structure, the EWG effect can be further enhanced due to the action of the N atom having a lower electronegativity than O, so that the driving voltage of the device can be reduced, leading to high efficiency. In addition, when an EWG is substituted on a ring different from N and S in the polycyclic spiro-based core structure, NR 11 has a bulky structure compared to an O atom and has a larger orbital region compared to an S or O atom, so that it is a structure in which the packing density can be relatively reduced when manufacturing a device. Due to the above effects, the mobility is reduced, and thus a stable long-life device can be formed.

[0036] In addition, the compound represented by Chemical Formula 1 of the present invention has steric hindrance due to the spiro structure, so that crystallization during film formation is prevented, and high thermal stability is maintained, thereby having an effect of being stable at a high evaporation temperature. Moreover, the electrochemical stability of the spiro-based core structure is very excellent, having a high glass transition temperature (Tg) and excellent carrier transport ability. Therefore, improvement in the efficiency of an organic light emitting device, low driving voltage, and improvement in life characteristics can be achieved.

[0037] As described above, when the compound represented by Chemical Formula 1 of the present invention is used as a material for the organic layer of an organic electroluminescent element, preferably as a material for a light-emitting layer (phosphorescent host material for blue, green, and / or red), an electron transport layer / injection layer material, a hole transport layer / injection layer material, a light-emission assisting layer material, or a lifetime improvement layer material, the performance and lifetime characteristics of the organic electroluminescent element can be significantly improved. In particular, when the compound of the present invention is used as a material for an electron transport layer or an electron transport assisting layer, significant excellent performance improvement effects can be expected in terms of the efficiency, driving voltage, and lifetime characteristics of the element. Such an organic electroluminescent element can ultimately maximize the performance of a full-color organic light-emitting panel.

[0038] The compound represented by Chemical Formula 1 of the present invention has a polycyclic spirobixanthene group containing at least two heteroatoms (S-S / O-S / S-NR’ / NR’-NR” / O-NR’) as a core structure, and the core structure is directly bonded to a nitrogen-containing heteroaromatic ring having an electron-withdrawing group (EWG) property with excellent electron transport ability (e.g., azine, a ring containing X1 to X3), thereby forming a basic skeleton structure.

[0039] The above polycyclic nut core structure contains at least two heteroatoms (e.g., a ring containing Y1 to Y2). According to one embodiment of such a polycyclic nut core structure, Y1 and Y2 are the same or different from each other, and each independently selected from the group consisting of O, S, and NR 11 composed of the group, excluding the case where Y1 and Y2 are both O at the same time. Specifically, it is preferred that Y1 and Y2 are different from each other.

[0040] Among them, R 11 is selected from the group consisting of hydrogen, deuterium (D), halogen, cyano, nitro, C1 to C 40 alkyl, C2 to C 40 alkenyl, C2 to C 40 alkynyl, C3 to C 40 cycloalkyl, a heteroalkyl having 3 to 40 ring atoms, C6 to C 60 aryl, a heteroaryl having 5 to 60 ring atoms, C1 to C 40 alkoxy, C6 to C 60 aryloxy, C3 to C 40 alkylsilyl, C6 to C 60 arylsilyl, C1 to C 40 alkylboron, C6 to C 60 arylboron, C6 to C 60 arylphosphino, C6 to C 60 arylphosphine oxide group and C6 to C60 a group consisting of arylamines, or they may combine with any adjacent groups to form a condensed ring. At this time, when R 11 is plural, the plural R 11 may be the same as or different from each other. Specifically, R 11 is preferably selected from the group consisting of hydrogen, deuterium (D), C1-C 40 alkyl, C6-C 60 aryl, and heteroaryl having 5 to 60 ring atoms.

[0041] According to a specific example, the structure of the polycyclic nut core (for example, a ring containing Y1 to Y2) can be further specified as any one selected from the following structural formulas. However, it is not limited thereto.

[0042]

[0043] In the above formula,

[0044] * refers to the position connected to the above Chemical Formula 1,

[0045] R 11 is selected from the group consisting of hydrogen, deuterium (D), C1-C 40 alkyl, C6-C 60 aryl, and heteroaryl having 5 to 60 ring atoms,

[0046] R1 to R4, o, p, q, and r are each the same as defined in Chemical Formula 1.

[0047] On the above polycyclic nut core (for example, a ring containing Y1 to Y2), R1 to R4 can be respectively substituted as various substituents. R1 to R4 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium (D), halogen, cyano, nitro, C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C3-C 40 cycloalkyl, heteroalkyl having 3 to 40 ring atoms, C6-C 60 aryl, heteroaryl having 5 to 60 ring atoms, C1-C 40 alkoxy, C6-C 60 aryloxy, C3-C 40 alkylsilyl, C6-C 60 arylsilyl, C1-C 40 alkylboron, C6-C 60 arylboron, C6-C 60 arylphosphino, C6-C 60 arylphosphinyl oxide, and C6-C 60A group consisting of arylamines, or they may combine with any adjacent group to form a condensed ring. At this time, when there are multiple R 11 to R4, the multiple R1 to R4 may each be the same as or different from each other. Specifically, R1 to R4 are the same as or different from each other, and are preferably each independently selected from the group consisting of hydrogen, deuterium (D), cyano, C1-C 40 alkyl, C6-C 60 aryl, and heteroaryl having 5 to 60 ring atoms, or a condensed ring formed by their combination with an adjacent group.

[0048] Among them, o, p, and q may each independently be an integer from 0 to 4, and r may be an integer from 0 to 3. Among them, when o is 0, R1 is hydrogen, and when o is 1 to 3, R1 may have the above substituents other than hydrogen. The same applies to p, q, and r.

[0049] In the chemical formula 1 of the present invention, one phenyl ring on one side of the polycyclic nut core (for example, the ring containing Y1 to Y2) structure is directly connected to a nitrogen-containing heteroaromatic ring having excellent electron transport ability and EWG characteristics (for example, azine, the ring containing X1 to X3).

[0050] The above nitrogen-containing heterocycle (for example, the ring containing X1 to X3) is a monocyclic or polycyclic nitrogen-containing heteroaryl containing at least two nitrogen atoms. According to one embodiment of the nitrogen-containing heteroaromatic ring, X1 to X3 are the same as or different from each other, and are each independently C(R5) or N, but at least two of X1 to X3 contain N. Specifically, it contains 2 to 3 Ns. Thus, by including a heterocycle containing 2 to 3 nitrogens, more excellent electron-withdrawing characteristics are exhibited, which is beneficial to electron injection and transport.

[0051] Among them, R5 is selected from the group consisting of hydrogen, deuterium (D), C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C3-C 40 cycloalkyl, heterocycloalkyl having 3 to 40 ring atoms, C6-C 60 aryl, heteroaryl having 5 to 60 ring atoms, C1-C 40 alkoxy, C6-C 60 aryloxy, C3-C 40 alkylsilyl, C6-C 60 arylsilyl, C1-C 40 alkylboron, C6-C 60 arylboron, C6-C 60 arylphosphanyl, C6-C 60 monoarylphosphinyl, C6-C60 a group consisting of a diarylphosphino group, a C6-C 60 arylamino group, a C5-C 60 arylheteroarylamino group and a heteroarylamino group having 5 to 60 ring atoms, or they may combine with any adjacent groups to form a condensed ring. At this time, when there are multiple R5s, the multiple R5s may be the same as or different from each other. Specifically, R5 is preferably selected from the group consisting of hydrogen, deuterium (D), a C1-C 40 alkyl group, a C6-C 60 aryl group and a heteroaryl group having 5 to 60 ring atoms.

[0052] According to a specific example, the nitrogen-containing heterocycle (for example, the ring containing X1 to X3) can be further specifically exemplified by any one of the following structural formulas. However, it is not limited thereto.

[0053]

[0054] In the above formula,

[0055] * indicates the position connected to the above Chemical Formula 1,

[0056] W is O or S,

[0057] Ar1 and Ar2 are each the same as defined in Chemical Formula 1.

[0058] On the above nitrogen-containing heterocycle (for example, the ring containing X1 to X3), Ar1 and Ar2 can be respectively substituted as various substituents. Ar1 and Ar2 may be the same as or different from each other, and are each independently selected from the group consisting of a C1-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40 alkynyl group, a C3-C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, a C6-C 60 aryl group, a heteroaryl group having 5 to 60 ring atoms, a C1-C 40 alkoxy group, a C6-C 60 aryloxy group, a C3-C 40 alkylsilyl group, a C6-C 60 arylsilyl group, a C1-C 40 alkylboron group, a C6-C 60 arylboron group, a C6-C 60 arylphosphino group, a C6-C 60 aryloxyphosphino group and a C6-C 60 arylamino group, or they may combine with any adjacent groups to form a condensed ring. Specifically, Ar1 and Ar2 can each independently be a C6-C 60An aryl group or a heteroaryl group having 5 to 60 nuclear atoms.

[0059] According to a specific example, Ar1 and Ar2 may be the same as or different from each other, and each may independently be further specifically represented by any one of the following structural formulas. However, it is not limited thereto.

[0060]

[0061]

[0062] In the above formula,

[0063] * refers to the position connected to the above Chemical Formula 1. In addition, although not shown in the above structural formula, it may be substituted with at least one substituent known in the art (for example, the same as the definition part of R5).

[0064] In the above Chemical Formula 1, the above Ar1 to Ar2, R1 to R5, and R 11 alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, alkylsilyl, arylsilyl, alkylboron, arylboron, arylphosphine, arylphosphine oxide, and arylamine groups may each independently be selected from the group consisting of deuterium (D), halogen, cyano, nitro, C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C3-C 40 cycloalkyl, heterocycloalkyl having 3 to 40 nuclear atoms, C6-C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1-C 40 alkoxy, C6-C 60 aryloxy, C1-C 40 alkylsilyl, C6-C 60 arylsilyl, C1-C 40 alkylboron, C6-C 60 arylboron, C6-C 60 arylphosphine, C6-C 60 arylphosphine oxide, and C6-C 60 arylamine groups are substituted with one or more substituents selected from the group consisting thereof, and when there are a plurality of the above substituents, they may be the same as or different from each other.

[0065] According to an embodiment of the present invention, the compound represented by the above Chemical Formula 1 may be further specifically represented by any one of the following Chemical Formulas 2 to 9 according to the type of heteroatom introduced into the polycyclic nut nuclear structure. However, it is not limited thereto.

[0066] [Chemical Formula 2]

[0067]

[0068] [Chemical Formula 3]

[0069]

[0070] [Chemical Formula 4]

[0071]

[0072] [Chemical Formula 5]

[0073]

[0074] [Chemical Formula 6]

[0075]

[0076] [Chemical Formula 7]

[0077]

[0078] [Chemical Formula 8]

[0079]

[0080] [Chemical Formula 9]

[0081]

[0082] In the above formulas,

[0083] X1 to X3, Ar1 to Ar2, R1 to R4, R 11 , o, p, q and r are each the same as defined in Chemical Formula 1.

[0084] According to another embodiment of the present invention, the compound represented by the above Chemical Formula 1 can be further specified as any one of the following Chemical Formulas 10 to 20 according to the type of the nitrogen-containing heterocycle (for example, the ring containing X1 to X¬3¬). However, it is not limited thereto.

[0085] [Chemical Formula 10]

[0086]

[0087] [Chemical Formula 11]

[0088]

[0089] [Chemical Formula 12]

[0090]

[0091] [Chemical Formula 13]

[0092]

[0093] [Chemical Formula 14]

[0094]

[0095] [Chemical Formula 15]

[0096]

[0097] [Chemical Formula 16]

[0098]

[0099] [Chemical Formula 17]

[0100]

[0101] [Chemical Formula 18]

[0102]

[0103] [Chemical Formula 19]

[0104]

[0105] [Chemical Formula 20]

[0106]

[0107] In the above formulas,

[0108] W is O or S,

[0109] Y1 to Y2, Ar1 to Ar2, R1 to R4, o, p, q, and r are each the same as defined in Chemical Formula 1.

[0110] According to another embodiment of the present invention, the compound represented by the above Chemical Formula 1 can be further specified as any one of the following Chemical Formulas 21 to 28 according to the bonding position of the condensed ring formed in the polycyclic nut nucleus. However, it is not limited thereto.

[0111] [Chemical Formula 21]

[0112]

[0113] [Chemical Formula 22]

[0114]

[0115] [Chemical Formula 23]

[0116]

[0117] [Chemical Formula 24]

[0118]

[0119] [Chemical Formula 25]

[0120]

[0121] [Chemical Formula 26]

[0122]

[0123] [Chemical Formula 27]

[0124]

[0125] [Chemical Formula 28]

[0126]

[0127] In the above formulas,

[0128] Ring A can be a common hydrocarbon-based ring known in the art or a hydrocarbon-based ring containing one or more heteroatoms, and can be in a form where they are combined with other adjacent rings (for example, the parent nucleus structure) by condensation, fusion, bridging, or spirocyclic bonding. For example, Ring A can be selected from the group consisting of monocyclic or polycyclic alicyclic rings, monocyclic or polycyclic heteroalicyclic rings, monocyclic or polycyclic aromatic rings, or monocyclic or polycyclic heteroaromatic rings. Specifically, Ring A is preferably an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 5 to 18 nuclear atoms.

[0129] X1 to X3, Y1 to Y2, Ar1 to Ar2, R1 to R4, o, p, q, and r are each the same as defined in Chemical Formula 1.

[0130] According to another embodiment of the present invention, the compound represented by the above Chemical Formula 1 can be further specified as any one of the following Chemical Formulas 29 to 31 according to the bonding position of the nitrogen-containing heterocycle. However, it is not limited thereto.

[0131] [Chemical Formula 29]

[0132]

[0133] [Chemical Formula 30]

[0134]

[0135] [Chemical Formula 31]

[0136]

[0137] In the above formulae,

[0138] X1 to X3, Y1 to Y2, Ar1 to Ar2, R1 to R4, o, p, q and r are each the same as defined in claim 1.

[0139] The compound represented by Chemical Formula 1 of the present invention described above can be further specified as any one of Compounds 1 to 120 exemplified below. However, the compound represented by Chemical Formula 1 of the present invention is not limited by the compounds exemplified below.

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148] In the present invention, the "number of ring nuclei" means the number of ring atoms constituting the ring structure, and the above-mentioned ring atoms may refer to carbon or heteroatoms selected from the group consisting of N, O, S and Se. For example, the number of ring nuclei of pyridine is 6, including 5 C and 1 N constituting the pyridine ring.

[0149] In the present invention, "alkyl" means a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, etc., but are not limited thereto.

[0150] In the present invention, "alkenyl" means a monovalent substituent derived from a straight-chain or branched-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.

[0151] In the present invention, "alkynyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms with one or more carbon-carbon triple bonds. Examples thereof include ethynyl, 2-propynyl, etc., but are not limited thereto.

[0152] In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms composed of a single ring or a combination of two or more rings. In addition, it may also include a form in which two or more rings are simply attached (pendant) or condensed with each other. Examples of such aryl include phenyl, naphthyl, phenanthryl, anthryl, etc., but are not limited thereto.

[0153] In the present invention, "heteroaryl" means a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, one or more carbons in the ring, preferably 1 to 3 carbons, are replaced by heteroatoms such as N, O, S, or Se. In addition, it may also include a form in which two or more rings are simply attached (pendant) or condensed with each other, and further may include a form condensed with an aryl. Examples of such heteroaryl include six-membered monocycles such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; polycycles such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl; and 2-furyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl, 2-pyrimidinyl, etc., but are not limited thereto.

[0154] In the present invention, "aryloxy" is a monovalent substituent represented by RO-, and the above R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenoxy, naphthyloxy, diphenoxy, etc., but are not limited thereto.

[0155] In the present invention, "alkoxy" is a monovalent substituent represented by R'O-, and the above R' means an alkyl having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of alkoxy include methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, pentyloxy, etc., but are not limited thereto.

[0156] In the present invention, "arylamino" means an amino group substituted with an aryl having 6 to 40 carbon atoms.

[0157] In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, etc.

[0158] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, in which one or more carbons, preferably 1 to 3 carbons, in the ring are replaced by heteroatoms such as N, O, S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholinyl, piperazinyl, etc.

[0159] In the present invention, "alkylsilyl" means a silyl group substituted by an alkyl group having 1 to 40 carbon atoms, and "arylsilyl" means a silyl group substituted by an aryl group having 5 to 40 carbon atoms.

[0160] In the present invention, "fused ring" means a form obtained by fusing an aliphatic ring, an aromatic ring, a heteroaliphatic ring, a heteroaromatic ring, or a combination thereof.

[0161] <Electron transport layer material>

[0162] The present invention provides an electron transport layer comprising the compound represented by the above chemical formula 1.

[0163] The above electron transport layer (ETL) functions to migrate electrons injected from the cathode to an adjacent layer, specifically to the light-emitting layer.

[0164] The compound represented by the above chemical formula 1 can be used alone as an electron transport layer (ETL) material, and can also be mixed with electron transport layer materials well-known in the art. It is preferably used alone.

[0165] The electron transport layer materials that can be mixed with the compound of the above chemical formula 1 include electron transport substances commonly known in the art. Non-limiting examples of electron transport substances that can be used include 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-hydroxyquinolinato)-aluminium), BAlq, SAlq, Almq3), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. They can be used alone or in combination of two or more.

[0166] In the present invention, when the compound of Chemical Formula 1 and the electron transport layer material are mixed, their mixing ratio is not particularly limited and can be appropriately adjusted within the range well known in the art.

[0167] <Electron transport auxiliary layer material>

[0168] In addition, the present invention provides an electron transport auxiliary layer containing the compound represented by Chemical Formula 1 above.

[0169] The above electron transport auxiliary layer is disposed between the light-emitting layer and the electron transport layer, and functions to prevent excitons or holes generated in the above light-emitting layer from diffusing into the electron transport layer.

[0170] The compound represented by Chemical Formula 1 above can be used alone as an electron transport auxiliary layer material. In addition, it can also be mixed with electron transport auxiliary layer materials well known in the art. It is preferably used alone.

[0171] The electron transport auxiliary layer materials that can be mixed with the compound of Chemical Formula 1 above include electron transport substances commonly known in the art. For example, the above electron transport auxiliary layer can include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), nitrogen-containing heterocyclic derivatives, etc.

[0172] In the present invention, when the compound of Chemical Formula 1 and the electron transport auxiliary layer material are mixed, their mixing ratio is not particularly limited and can be appropriately adjusted within the range well known in the art.

[0173] <Organic electroluminescent element>

[0174] On the other hand, another aspect of the present invention relates to an organic electroluminescent element (organic EL element) containing the compound represented by Chemical Formula 1 of the present invention above.

[0175] Specifically, the organic electroluminescent element of the present invention includes an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, and at least one of the one or more organic layers contains the compound represented by Chemical Formula 1 above. At this time, the above compound can be used alone or two or more kinds can be mixed and used.

[0176] The above one or more organic layers can be any one or more of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a lifetime improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one organic layer contains the compound represented by Chemical Formula 1 above. Specifically, the organic layer containing the compound of Chemical Formula 1 above can be a light-emitting layer, a light-emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and / or a lifetime improvement layer. More specifically, it is preferably an electron transport layer or an electron transport auxiliary layer.

[0177] The light-emitting layer of the organic electroluminescent element of the present invention contains a host material and a dopant material. At this time, as the host material, the compound represented by Chemical Formula 1 above may be included. In addition, the light-emitting layer of the present invention may contain a compound known in the art other than the compound represented by Chemical Formula 1 above as the host.

[0178] When the compound represented by Chemical Formula 1 above is included as a material for the light-emitting layer of an organic electroluminescent element, preferably as a blue, green, or red phosphorescent host material, the binding force between holes and electrons in the light-emitting layer becomes higher, so that the efficiency (light-emitting efficiency and power efficiency), lifespan, brightness, and driving voltage of the organic electroluminescent element can be improved. Specifically, the compound represented by Chemical Formula 1 above is preferably included in the organic electroluminescent element as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, the compound represented by Chemical Formula 1 of the present invention is preferably a green phosphorescent exciplex N-type host material having a highly efficient light-emitting layer.

[0179] The structure of the organic electroluminescent element of the present invention is not particularly limited and 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. At this time, one or more of the above hole injection layer, hole transport layer, light-emitting auxiliary layer, light-emitting layer, electron transport layer, and electron injection layer may contain the compound represented by Chemical Formula 1 above. Preferably, the light-emitting layer, and more preferably, the phosphorescent host may contain the compound represented by Chemical Formula 1 above. In addition, an electron injection layer may be further stacked on the above electron transport layer.

[0180] The structure of the organic electroluminescent element 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.

[0181] In addition to one or more of the above organic layers containing the compound represented by Chemical Formula 1 above, the organic electroluminescent element of the present invention may form and manufacture the organic layer and the electrode using materials and methods known in the art.

[0182] The above organic layer may be formed by a vacuum evaporation method or a solution coating method. Examples of the above solution coating method include spin coating, dip coating, blade coating, inkjet printing, or thermal transfer printing, etc., but are not limited thereto.

[0183] The substrate used in manufacturing the organic electroluminescent element of the present invention is not particularly limited. For example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet, etc. may be used.

[0184] In addition, the anode material can be any anode material well-known in the art without limitation. For example, metals such as vanadium, chromium, copper, zinc, and gold, or their alloys can be cited; 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-(ethylenedioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, etc., but not limited thereto.

[0185] In addition, the cathode material can be any cathode material well-known in the art without limitation. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or their alloys can be cited; and multilayer structure materials such as LiF / Al or LiO / Al, etc., but not limited thereto.

[0186] In addition, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and any common materials well-known in the art can be used without limitation.

[0187] Hereinafter, the present invention will be described in detail by way of examples, as follows. However, the following examples are only illustrative of the present invention, and the present invention is not limited by the following examples.

[0188] [Preparation Examples 1-9: Synthesis of Core]

[0189] The polycyclic spiro-based parent nucleus structure of the present invention can be manufactured according to the following Reaction Formula 1. However, it is not limited thereto, and it can be manufactured according to common reaction methods well-known in the art.

[0190] [Reaction Formula]

[0191]

[0192] In the above reaction formula, Hal 1 of compound (A) can be a common halogen element well-known in the art, specifically, it can be Br or I. In addition, Hal 2 of compound (B) can be a common halogen element, specifically, it can be Cl, Br, or I.

[0193] In the above parent nucleus structure, Y1 to Y2, R1 to R4, o, p, q, and r are the same as those defined in Chemical Formula 1.

[0194] [Preparation Example 1]

[0195] [Step 1] Synthesis of 2-Chlorospiro[thioxanthene-9,9'-xanthene]

[0196]

[0197] Under a nitrogen atmosphere, 1-bromo-2-phenoxybenzene (50 g, 200.7 mmol), which is the compound (A) of Reaction Scheme 1, was dissolved in 670 ml of THF, and 1.6 M n-BuLi solution (134 ml, 220.8 mmol) was added dropwise with stirring at -78 °C, followed by stirring for 1 hour. 2-Chloro-9H-thioxanthen-9-one (54.4 g, 220.8 mmol), which is the compound (B) of Reaction Scheme 1, was dissolved in 220 ml of THF and then added dropwise. After stirring for 30 minutes, the temperature was raised to room temperature, and then stirred for 2 hours. After confirming the disappearance of the raw materials, the solvent was concentrated under reduced pressure, 115 ml of AcOH and 115 ml of HCl were added, and the mixture was heated and stirred at 70 °C for 1 hour. After cooling to room temperature, the reaction solution was extracted with dichloromethane, dried over MgSO4 to remove water, and then filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified with methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 2-chlorospiro[thioxanthene-9,9'-xanthene] (45.0 g, yield 56.2%).

[0198] Mass: [(M+H) + : 399

[0199] <Step 2> Synthesis of the parent nucleus 1

[0200]

[0201] 2-Chlorospiro[thioxanthene-9,9'-xanthene] (45.0 g, 112.8 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (37.2 g, 146.6 mmol), Pd(dppf)Cl2 (2.5 g, 6.7 mmol), KOAc (65.3 g, 665.4 mmol), and Xphos (6.3 g, 13.3 mmol) were added to 750 ml of 1,4-dioxane and heated under reflux for 12 hours. After the reaction was completed, the mixture was extracted with dichloromethane, dried over MgSO4 to remove water, and then filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified with methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain the parent nucleus 1 (45.2 g, yield 81.7%).

[0202] Mass: [(M+H) + : 491

[0203] [Preparation Example 2]

[0204] [Step 1] Synthesis of 4'-Chlorospiro[thioxanthene-9,9'-xanthene]

[0205]

[0206] In Step 1 of Preparation Example 1, (2-bromophenyl)(phenyl)sulfane (50 g, 188.6 mmol), 4-chloro-9H-xanthen-9-one (47.8 g, 207.4 mmol), 1.6 M solution of n-BuLi (129 ml, 207.4 mmol), 830 ml of THF, 108 ml of AcOH, and 108 ml of HCl were used, and 4'-chlorospiro[thioxanthene-9,9'-xanthene] (42.0 g, yield 55.84%) was obtained using the same method as in Step 1 of Preparation Example 1.

[0207] Mass: [(M+H) + : 399

[0208] [Step 2] Synthesis of Core 2

[0209]

[0210] As the reactant in Step 2 of Preparation Example 1, 4'-chlorospiro[thioxanthene-9,9'-xanthene] (42.0 g, 105.3 mmol) was used instead of 2-chlorospiro[thioxanthene-9,9'-xanthene], and the same process as in <Step 2> of Preparation Example 1 was carried out to obtain the parent nucleus 2 (39.5 g, yield 76.5%).

[0211] Mass: [(M+H) + : 491

[0212] [Preparation Example 3]

[0213] [Step 1] Synthesis of 3-Chloro-10-phenyl-10H-spiro[acridine-9,9'-xanthene]

[0214]

[0215] In Step 1 of Preparation Example 1, 1-bromo-2-phenoxybenzene (50 g, 200.7 mmol), 3-chloro-10-phenylacridin-9(10H)-one (67.5 g, 220.8 mmol), 1.6 M solution of n-BuLi (138 ml, 220.8 mmol), 1000 ml of THF, 115 ml of AcOH, and 115 ml of HCl were used, and 3-chloro-10-phenyl-10H-spiro[acridine-9,9'-xanthene] (48.1 g, yield 52.3%) was obtained using the same method as in Step 1 of Preparation Example 1.

[0216] Mass: [(M+H) + : 458

[0217] [Step 2] Synthesis of Core 3

[0218]

[0219] As the reactant of Step 2 of Preparation Example 1, 3-chloro-10-phenyl-10H-spiro[acridine-9,9'-xanthene] (48.1 g, 105.0 mmol) was used instead of 2-chlorospiro[thioxanthene-9,9'-xanthene]. The same process as in <Step 2> of Preparation Example 1 was carried out to obtain the mother core 3 (35.5 g, yield 61.5%).

[0220] Mass: [(M+H) + ]:550

[0221] [Preparation Example 4]

[0222] [Step 1] Synthesis of 2'-Chloro-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene]

[0223]

[0224] In Step 1 of Preparation Example 1, 2-bromo-N,N-diphenylaniline (50 g, 154.2 mmol) and 2-chloro-9H-thioxanthen-9-one (41.8 g, 169.6 mmol), n-BuLi 1.6 M solution (106 ml, 169.6 mmol), 700 ml of THF, 89 ml of AcOH, and 89 ml of HCl were used, and the same method as in Step 1 of Preparation Example 1 was used to obtain 2'-chloro-10-phenyl-10H-spiro[acridine-9,9'-thioxanthen] (37.8 g, yield 51.7%).

[0225] Mass: [(M+H) + ]:474

[0226] [Step 2] Synthesis of Core 4

[0227]

[0228] As the reactant of step 2 of preparation example 1, 2'-chloro-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene] (37.8 g, 79.8 mmol) was used instead of 2-chlorospiro[thioxanthene-9,9'-xanthene]. The same process as <step 2> of preparation example 1 was carried out to obtain the mother core 4 (35.5 g, yield 78.7%).

[0229] Mass: [(M+H) + ]:566

[0230] [Preparation Example 5]

[0231] [Step 1] Synthesis of 2-Chloro-10-phenyl-10H-spiro[acridine-9,9'-xanthene]

[0232]

[0233] In Step 1 of Preparation Example 1, 1-bromo-2-phenoxybenzene (50 g, 200.7 mmol), 2-chloro-10-phenylacridin-9(10H)-one (67.5 g, 220.8 mmol), 1.6 M solution of n-BuLi (138 ml, 220.8 mmol), 900 ml of THF, 114 ml of AcOH, and 114 ml of HCl were used, and 2-chloro-10-phenyl-10H-spiro[acridine-9,9'-xanthene] (60.0 g, yield 65.3%) was obtained using the same method as in Step 1 of Preparation Example 1.

[0234] Mass: [(M+H) + : 458

[0235] [Step 2] Synthesis of Core 5

[0236]

[0237] As the reactant for Step 2 of Preparation Example 1, 2-chloro-10-phenyl-10H-spiro[acridine-9,9'-xanthene] (60.0 g, 131.0 mmol) was used instead of 2-chlorospiro[xanthene-9,9'-xanthene], and the same procedure as in <Step 2> of Preparation Example 1 was carried out to obtain the parent nucleus 5 (48.8 g, yield 67.8%).

[0238] Mass: [(M+H) + : 550

[0239] [Preparation Example 6]

[0240] [Step 1] Synthesis of 4'-Chlorospiro[benzo[b]xanthene-12,9'-thioxanthene]

[0241]

[0242] In Step 1 of Preparation Example 1, 2-bromo-3-phenoxynaphthalene (30 g, 100.3 mmol), 4-chloro-9H-xanthen-9-one (27.2 g, 110.3 mmol), 1.6 M solution of n-BuLi (68.9 ml, 110.3 mmol), 450 ml of THF, 58 ml of AcOH, and 58 ml of HCl were used, and 4'-chlorospiro[benzo[b]xanthene-12,9'-xanthene] (24.6 g, yield 54.64%) was obtained using the same method as in Step 1 of Preparation Example 1.

[0243] Mass: [(M+H) + : 449

[0244] [Step 2] Synthesis of Core 6

[0245]

[0246] As the reactant for Step 2 of Preparation Example 1, 4'-chlorospiro[benzo[b]xanthene-12,9'-thioxanthene] (24.6 g, 54.8 mmol) was used instead of 2-chlorospiro[thioxanthene-9,9'-xanthene]. Except for this, the same process as <Step 2> of Preparation Example 1 was carried out to obtain the mother nucleus 6 (20.0 g, yield 67.5%).

[0247] Mass: [(M+H) + : 540

[0248] [Preparation Example 7]

[0249] [Step 1] Synthesis of 2-Bromospiro[thioxanthene-9,9'-xanthene]-7-carbonitrile

[0250]

[0251] In Step 1 of Preparation Example 1, 1-bromo-2-phenoxybenzene (30 g, 120.4 mmol), 7-bromo-9-oxo-9H-thioxanthene-2-carbonitrile (41.8 g, 132.5 mmol), 1.6 M solution of n-BuLi (83 ml, 132.5 mmol), 550 ml of THF, 69 ml of AcOH, and 69 ml of HCl were used, and the same method as in Step 1 of Preparation Example 1 was used to obtain 2-bromospiro[thioxanthene-9,9'-xanthene]-7-carbonitrile (26.2 g, yield 46.4%).

[0252] Mass: [(M+H) + : 469

[0253] <Step 2> Synthesis of mother nucleus 7

[0254]

[0255] 2-Bromospiro[thioxanthene-9,9'-xanthene]-7-carbonitrile (26.2 g, 55.9 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (18.5 g, 72.7 mmol), Pd(dppf)Cl2 (1.2 g, 1.7 mmol), and KOAc (16.5 g, 168 mmol) were added to 200 ml of 1,4-dioxane and heated under reflux for 12 hours. After the reaction was completed, extraction was carried out with dichloromethane. After adding MgSO4 to remove water, filtration was performed. After filtration, the solvent of the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain the mother nucleus 7 (20.5 g, yield 71.1%).

[0256] Mass: [(M+H) + : 515

[0257] [Preparation Example 8]

[0258] [Step 1] Synthesis of 4'-Chloro-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene]

[0259]

[0260] In Step 1 of Preparation Example 1, 2-bromo-N,N-diphenylaniline (30 g, 92.5 mmol), 4-chloro-9H-thioxanthen-9-one (25.1 g, 101.8 mmol), 1.6 M solution of n-BuLi (63 ml, 101.8 mmol), 410 ml of THF, 53 ml of AcOH, and 53 ml of HCl were used, and the same method as in Step 1 of Preparation Example 1 was used to obtain 4'-chloro-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene] (25.5 g, yield 58.1%).

[0261] Mass: [(M+H) + : 474

[0262] <Step 2>Synthesis of mother nucleus 8

[0263]

[0264] As the reactant in Step 2 of Preparation Example 1, 4'-chloro-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene] (25.5 g, 53.8 mmol) was used instead of 2-chlorospiro[thioxanthene-9,9'-xanthene]. Except for this, the same process as <Step 2> of Preparation Example 1 was carried out to obtain the mother nucleus 8 (19.9 g, yield 65.4%).

[0265] Mass: [(M+H)+ :565

[0266] [Preparation Example 9]

[0267] [Step 1] Synthesis of 4-Bromo-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene]

[0268]

[0269] In Step 1 of Preparation Example 1, (2-bromophenyl)(phenyl)sulfane (50 g, 188.6 mmol), 4-bromo-10-phenylacridin-9(10H)-one (72.6 g, 207.4 mmol), 1.6 M solution of n-BuLi (129 ml, 207.4 mmol), 830 ml of THF, 108 ml of AcOH, and 108 ml of HCl were used, and the same method as in Step 1 of Preparation Example 1 was used to obtain 4-bromo-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene] (44.5 g, yield 59.2%).

[0270] Mass: [(M+H) + :399

[0271] <Step 2> Synthesis of Parent Nucleus 9

[0272]

[0273] As the reactant in Step 2 of Preparation Example 7, 4-bromo-10-phenyl-10H-spiro[acridine-9,9'-thioxanthene] (44.5 g, 111.5 mmol) was used instead of 2-bromospiro[thioxanthene-9,9'-xanthene]-7-carbonitrile, and the same process as <Step 2> of Preparation Example 7 was carried out to obtain parent nucleus 9 (38.0 g, yield 60.2%).

[0274] Mass: [(M+H) + :566

[0275] [Synthesis Examples 1-19]

[0276] [Synthesis Example 1] Synthesis of Inv6

[0277]

[0278] 2-Chloro-4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-phenyl-1,3,5-triazine (15.0 g, 30.1 mmol), the parent nucleus 6 of [Preparation Example 6] (17.9 g, 33.1 mmol), Pd(Pph3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.5 g, 90.2 mmol) were added to 120 ml of toluene, 30 ml of EtOH, and 30 ml of H2O, and the mixture was heated under reflux for 4 hours. After the reaction was completed, extraction was carried out with dichloromethane, and MgSO4 was added followed by filtration. After removing the solvent of the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was carried out using toluene and acetone to obtain Inv 6 (28.2 g, yield 84.8%).

[0279] Mass: [(M + H) + : 878

[0280] [Synthesis Example 2] Synthesis of Inv7

[0281]

[0282] 3'-(4-Chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (15.0 g, 40.7 mmol), 4,4,5,5-tetramethyl-2-(3'-phenylspiro[xanthene-9,9'-xanthene]-4-yl)-1,3,2-dioxaborolane (25.3 g, 44.7 mmol), Pd(Pph3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.9 g, 122.0 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of H2O, and the mixture was heated under reflux for 4 hours. After the reaction was completed, extraction was carried out with dichloromethane, and MgSO4 was added followed by filtration. After removing the solvent of the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was carried out using toluene and acetone to obtain Inv7 (19.87 g, yield 62.9%).

[0283] Mass: [(M + H) + : 773

[0284] [Synthesis Example 3] Synthesis of Inv8

[0285]

[0286] 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-carbonitrile (15.0 g, 40.7 mmol), 4,4,5,5-tetramethyl-2-(spiro[benzo[c]xanthene-7,9'-thioxanthen]-9-yl)-1,3,2-dioxaborolane (24.2 g, 44.7 mmol), Pd(Pph3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.9 g, 122.0 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of H2O, and the mixture was heated under reflux for 4 hours. After the reaction was completed, extraction was carried out with dichloromethane, and MgSO4 was added followed by filtration. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was carried out using toluene and acetone to obtain Inv8 (21.0 g, yield 69.1%).

[0287] Mass: [(M+H) + : 747

[0288] [Synthesis Example 4] Synthesis of Inv13

[0289]

[0290] 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (15.0 g, 40.7 mmol), 10-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-thioxanthene] (25.3 g, 44.7 mmol), Pd(Pph3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.9 g, 122.0 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of H2O, and the mixture was heated under reflux for 4 hours. After the reaction was completed, extraction was carried out with dichloromethane, and MgSO4 was added followed by filtration. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was carried out using toluene and acetone to obtain Inv 13 (18.1 g, yield 57.7%).

[0291] Mass: [(M+H) + : 772

[0292] [Synthesis Example 5] Synthesis of Inv29

[0293]

[0294] 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (15.0 g, 40.8 mmol), the parent nucleus 3 of [Preparation Example 3] (17.9 g, 33.1 mmol), Pd(Pph3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.9 g, 122.3 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of H2O, and the mixture was heated under reflux for 4 hours. After the reaction was completed, extraction was carried out with dichloromethane, and MgSO4 was added followed by filtration. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was carried out using toluene and acetone to obtain Inv 29 (24.6 g, yield 79.9%).

[0295] Mass: [(M+H) + : 755

[0296] [Synthesis Example 6] Synthesis of Inv40

[0297]

[0298] 3'-(6-chloro-2-phenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-carbonitrile (15.0 g, 35.7 mmol), the parent nucleus 1 of [Preparation Example 1] (19.3 g, 39.3 mmol), Pd(Pph3)4 (1.2 g, 1.07 mmol), and K2CO3 (14.8 g, 107.2 mmol) were added to 120 ml of toluene, 30 ml of EtOH, and 30 ml of H2O, and the mixture was heated under reflux for 4 hours. After the reaction was completed, extraction was carried out with dichloromethane, and MgSO4 was added followed by filtration. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was carried out using toluene and acetone to obtain Inv 40 (19.5 g, yield 72.9%).

[0299] Mass: [(M+H) + : 748

[0300] [Synthesis Example 7] Synthesis of Inv41

[0301]

[0302] Using 2-chloro-4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-phenyl-1,3,5-triazine (15.0 g, 30.06 mmol) to replace 3'-(6-chloro-2-phenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-carbonitrile, and except for this, the same procedure as in [Synthesis Example 3] was carried out to obtain Inv 41 (15.8 g, yield 63.5%).

[0303] Mass: [(M+H) + :827

[0304] [Synthesis Example 8] Synthesis of Inv44

[0305]

[0306] 2-(4-Chlorophenyl)-4,6-diphenyl-1,3,5-triazine (8.0 g, 23.3 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[xanthene-9,9'-thioxanthene]-4-yl)-1,3,5-triazine (18.5 g, 25.6 mmol), Pd(OAc)2 (0.2 g, 0.7 mmol), XPhos (1.1 g, 2.33 mmol), and Cs2CO3 (22.7 g, 69.8 mmol) were added to 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and the mixture was heated under reflux for 4 hours. After the reaction was completed, extraction was performed with dichloromethane, and MgSO4 was added followed by filtration. After removing the solvent from the filtered organic layer, column chromatography was carried out using dichloromethane and hexane, and then recrystallization was performed using toluene and acetone to obtain Inv 44 (16.5 g, yield 78.5%).

[0307] Mass: [(M+H) + :903

[0308] [Synthesis Example 9] Synthesis of Inv46

[0309]

[0310] 2-Chloro-4-phenyl-6-(3-(pyridin-3-yl)phenyl)-1,3,5-triazine (15.0 g, 43.5 mmol), the parent nucleus 8 of [Preparation Example 8] (27.1 g, 47.8 mmol), Pd(Pph3)4 (1.5 g, 1.3 mmol), and K2CO3 (18.0 g, 130.5 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of H2O, and the mixture was heated under reflux for 4 hours. After the reaction was completed, extraction was performed with dichloromethane, and MgSO4 was added followed by filtration. After removing the solvent from the filtered organic layer, column chromatography was carried out using dichloromethane and hexane, and then recrystallization was performed using toluene and acetone to obtain Inv 46 (28.0 g, yield 86.1%).

[0311] Mass: [(M+H) + :748

[0312] [Synthesis Example 10] Synthesis of Inv54

[0313]

[0314] 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (15.0 g, 40.7 mmol), the parent nucleus 2 of [Preparation Example 2] (21.9 g, 44.7 mmol), Pd(Pph3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.9 g, 122.0 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of H2O, and the mixture was heated under reflux for 4 hours. After the reaction was completed, extraction was carried out with dichloromethane, and after adding MgSO4, filtration was performed. After removing the solvent of the filtered organic layer, column chromatography was carried out using dichloromethane and hexane, and then recrystallization was carried out using toluene and acetone to obtain Inv 54 (22.5 g, yield 79.4%).

[0315] Mass: [(M+H) + : 697

[0316] [Synthesis Example 11] Synthesis of Inv56

[0317]

[0318] 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-carbonitrile (15.0 g, 40.7 mmol), the parent nucleus 7 of [Preparation Example 7] (23.1 g, 44.7 mmol), Pd(Pph3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.9 g, 122.0 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of H2O, and the mixture was heated under reflux for 4 hours. After the reaction was completed, extraction was carried out with dichloromethane, and after adding MgSO4, filtration was performed. After removing the solvent of the filtered organic layer, column chromatography was carried out using dichloromethane and hexane, and then recrystallization was carried out using toluene and acetone to obtain Inv 56 (23.2 g, yield 79.0%).

[0319] Mass: [(M+H) + : 722

[0320] [Synthesis Example 12] Synthesis of Inv63

[0321]

[0322] 2-Chloro-4-(9,9-diphenyl-9H-fluoren-2-yl)-6-phenyl-1,3,5-triazine (14.3 g, 28.2 mmol), the parent nucleus 5 of [Preparation Example 5] (17.0 g, 31.0 mmol), Pd(Pph3)4 (1.0 g, 0.85 mmol), and K2CO3 (11.7 g, 84.6 mmol) were added to 120 ml of toluene, 30 ml of EtOH, and 30 ml of H2O, and the mixture was heated under reflux for 4 hours. After the reaction was completed, extraction was performed with dichloromethane, and MgSO4 was added followed by filtration. After removing the solvent of the filtered organic layer, column chromatography was carried out using dichloromethane and hexane, and then recrystallization was performed using toluene and acetone to obtain Inv 63 (21.0 g, yield 81.0%).

[0323] Mass: [(M+H) + : 920

[0324] [Synthesis Example 13] Synthesis of Inv78

[0325]

[0326] 2-([1,1'-Biphenyl]-4-yl)-4-([1,1':2',1”-terphenyl]-3-yl)-6-chloro-1,3,5-triazine (10.0 g, 20.2 mmol), the parent nucleus 4 of [Preparation Example 4] (12.5 g, 22.2 mmol), Pd(Pph3)4 (0.7 g, 0.6 mmol), and K2CO3 (8.4 g, 60.5 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H2O, and the mixture was heated under reflux for 4 hours. After the reaction was completed, extraction was performed with dichloromethane, and MgSO4 was added followed by filtration. After removing the solvent of the filtered organic layer, column chromatography was carried out using dichloromethane and hexane, and then recrystallization was performed using toluene and acetone to obtain Inv 78 (14.2 g, yield 78.3%).

[0327] Mass: [(M+H) + : 899

[0328] [Synthesis Example 14] Synthesis of Inv86

[0329]

[0330] Use 2-([1,1'-biphenyl]-3-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (10.0 g, 23.8 mmol) to replace 2-([1,1'-biphenyl]-4-yl)-4-([1,1':2',1”-terphenyl]-3-yl)-6-chloro-1,3,5-triazine. Except for this, perform the same process as in [Synthesis Example 9] to obtain Inv 86 (13.5 g, yield 68.9%).

[0331] Mass: [(M+H) + :823

[0332] [Synthesis Example 15] Synthesis of Inv97

[0333]

[0334] Use 2'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile (10.0 g, 22.33 mmol) to replace 2-([1,1'-biphenyl]-4-yl)-4-([1,1':2',1”-terphenyl]-3-yl)-6-chloro-1,3,5-triazine. Except for this, perform the same process as in [Synthesis Example 9] to obtain Inv 97 (16.4 g, yield 86.4%).

[0335] Mass: [(M+H) + :853

[0336] [Synthesis Example 16] Synthesis of Inv100

[0337]

[0338] Add 3-(4-chloro-6-(4-cyanophenyl)-1,3,5-triazin-2-yl)benzonitrile (15.0 g, 47.2 mmol), the parent nucleus 9 of [Preparation Example 9] (29.4 g, 51.9 mmol), Pd(Pph3)4 (1.6 g, 1.4 mmol), and K2CO3 (19.6 g, 141.6 mmol) to 160 ml of toluene, 40 ml of EtOH, and 40 ml of H2O, and heat under reflux for 4 hours. After the reaction is completed, extract with dichloromethane, add MgSO4, and then filter. After removing the solvent of the filtered organic layer, perform column chromatography using dichloromethane and hexane, and then recrystallize using toluene and acetone to obtain Inv 100 (28.8 g, yield 84.6%).

[0339] Mass: [(M+H) + :721

[0340] [Synthesis Example 17] Synthesis of Inv111

[0341]

[0342] Using 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-(4-(naphthalen-1-yl)phenyl)-1,3,5-triazine (15.0 g, 31.9 mmol) to replace 2-(6-chloro-2-phenylpyrimidin-4-yl)-9,9-diphenyl-9H-fluorene-3-carbonitrile, except for this, the same procedure as in [Synthesis Example 8] was carried out to obtain Inv 111 (19.8 g, yield 72.4%).

[0343] Mass: [(M+H) + :858

[0344] [Synthesis Example 18] Synthesis of Inv113

[0345]

[0346] Using 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-carbonitrile (15.0 g, 40.7 mmol) to replace 3-(4-chloro-6-(4-cyanophenyl)-1,3,5-triazin-2-yl)benzonitrile, except for this, the same procedure as in [Synthesis Example 16] was carried out to obtain Inv 113 (22.5 g, yield 71.7%).

[0347] Mass: [(M+H) + :772

[0348] [Synthesis Example 19] Synthesis of Inv115

[0349]

[0350] 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (15.0 g, 40.7 mmol), 10-phenyl-3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-xanthene] (24.6 g, 44.7 mmol), Pd(Pph3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.9 g, 122.0 mmol) were added to 160 ml of toluene, 40 ml of EtOH, and 40 ml of H2O, and the mixture was heated under reflux for 4 hours. After the reaction was completed, extraction was carried out with dichloromethane, and after adding MgSO4, filtration was carried out. After removing the solvent of the filtered organic layer, column chromatography was carried out using dichloromethane and hexane, and then recrystallization was carried out using toluene and acetone to obtain Inv 115 (24.0 g, yield 78.0%).

[0351] Mass: [(M+H) + ]:756

[0352] [Examples 1-19] Fabrication of Blue Organic Electroluminescent Devices

[0353] Each compound synthesized above was purified to high purity by sublimation according to a commonly known method, and then a blue organic electroluminescent device was produced as follows.

[0354] First, we will A glass substrate coated with a thin film of indium tin oxide (ITO) was ultrasonically cleaned with distilled water. After the distilled water wash, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a UV ozone cleaner (Power sonic 405, Hwashintech). Afterwards, the substrate was cleaned with UV light for 5 minutes and then transferred to a vacuum evaporator.

[0355] On the ITO transparent electrode prepared as above, Each compound: The organic electroluminescent element is produced by sequential stacking.

[0356] The structures of HT-1, HAT-CN, HT-2, BH, BD, ET-1, ET-2, and LiQ used at this time are as follows.

[0357]

[0358]

[0359] [Comparative Examples 1-4] Fabrication of Blue Organic Electroluminescent Devices

[0360] As the electron transport layer material, Blue organic electroluminescent devices of Comparative Examples 1 to 4 were produced in the same manner as in Example 1 except that ET-1, ET-3, ET-4, and ET-5 were vapor-deposited instead of Compound 1.

[0361] The structures of ET-3, ET-4, and ET-5 used at this time are as follows.

[0362]

[0363] [Evaluation Example 1]

[0364] The current density of 10 mA / cm was measured for each of the blue organic electroluminescent devices prepared in Examples 1 to 19 and Comparative Examples 1 to 4. 2The driving voltage, current efficiency, and T at that time 95 and the emission peak. The results are shown in Table 1 below.

[0365] [Table 1]

[0366]

[0367]

[0368] As shown in Table 1 above, it can be seen that the blue organic electroluminescent elements of Examples 1 to 19 using the compound of the present invention as the electron transport layer material show more excellent performance in terms of driving voltage, emission peak, and current efficiency compared with the blue organic electroluminescent elements of Comparative Examples 1 to 4 using ET-1, ET-3, ET-4, and ET-5 as the electron transport layer material in the past.

Claims

1. A compound represented by the following Chemical Formula 1: [Chemical Formula 1] In the Chemical Formula 1, X1 to X3 are the same as or different from each other, and are each independently C(R5) or N, provided that at least two of X1 to X3 are N; Y1 and Y2 are the same as or different from each other and are each independently selected from the group consisting of O, S, and NR 11 with the proviso that the case where Y1 and Y2 are both O is excluded Ar1 and Ar2 are the same as or different from each other, and each independently selected from the group consisting of C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C3-C 40 cycloalkyl, heteroalkyl having 3 to 40 ring atoms, C6-C 60 aryl, heteroaryl having 5 to 60 ring atoms, C1-C 40 alkoxy, C6-C 60 aryloxy, C3-C 40 alkylsilyl, C6-C 60 arylsilyl, C1-C 40 alkylboron, C6-C 60 arylboron, C6-C 60 arylphosphino, C6-C 60 arylphosphine oxide and C6-C 60 arylamino groups, or they may combine with any adjacent groups to form a condensed ring, R1 to R5 and R 11 are the same as or different from each other, and each independently selected from the group consisting of hydrogen, deuterium (D), halogen, cyano, nitro, C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C3-C 40 cycloalkyl, heteroalkyl having 3 to 40 ring atoms, C6-C 60 aryl, heteroaryl having 5 to 60 ring atoms, C1-C 40 alkoxy, C6-C 60 aryloxy, C3-C 40 alkylsilyl, C6-C 60 arylsilyl, C1-C 40 alkylboron, C6-C 60 arylboron, C6-C 60 arylphosphino, C6-C 60 arylphosphine oxide and C6-C 60 arylamino, or they may combine with any adjacent groups to form a condensed ring, o, p, and q are each independently an integer from 0 to 4, and r is an integer from 0 to 3; The Ar1 to Ar2, R1 to R5, and R 11 alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, alkylsilyl, arylsilyl, alkylboron, arylboron, arylphosphino, arylphosphinyl, and arylamino may each independently be selected from the group consisting of deuterium (D), halogen, cyano, nitro, C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C3-C 40 cycloalkyl, heterocycloalkyl having 3 to 40 ring atoms, C6-C 60 aryl, heteroaryl having 5 to 60 ring atoms, C1-C 40 alkoxy, C6-C 60 aryloxy, C1-C 40 alkylsilyl, C6-C 60 arylsilyl, C1-C 40 alkylboron, C6-C 60 arylboron, C6-C 60 arylphosphino, C6-C 60 arylphosphinyl, and C6-C 60 arylamino, and may be substituted with one or more substituents selected from the group consisting thereof. When there are a plurality of the substituents, they may be the same as or different from each other.

2. The compound according to claim 1, wherein the ring containing Y1 and Y2 is any one selected from the following structural formulas: In the formula, * indicates the position connected to the Chemical Formula 1; R 11 selected from the group consisting of hydrogen, deuterium (D), C1-C 40 alkyl groups, C6-C 60 aryl groups, and heteroaryl groups having 5 to 60 ring atoms, R1 to R4, o, p, q, and r are each the same as defined in claim 1.

3. The compound according to claim 1, wherein Y1 and Y2 are different from each other.

4. The compound according to claim 1, wherein the X-containing moiety is any one selected from the following structural formulas: In the formula, * indicates the position connected to the Chemical Formula 1; W is O or S; Ar1 and Ar2 are each the same as defined in claim 1.

5. The compound according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other and are each independently selected from the group consisting of aryl having 6 to C 60 and heteroaryl having 5 to 60 ring nuclei.

6. The compound according to claim 1, wherein Ar1 and Ar2 are each independently any one selected from the following structural formulas: In the formula, * indicates the position connected to the Chemical Formula 1.

7. The compound according to claim 1, wherein R1 to R4 are the same as or different from each other and are each independently selected from the group consisting of hydrogen, deuterium (D), cyano, C1-C 40 alkyl, C6-C 60 aryl, and heteroaryl having 5 to 60 nuclear atoms, or they combine with adjacent groups to form a condensed ring.

8. The compound according to claim 1, wherein the compound represented by the Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 9: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] In the formula, X1 to X3, Ar1 to Ar2, R1 to R4, R 11 , o, p, q, and r are each the same as defined in claim 1.

9. The compound according to claim 1, wherein the compound represented by the Chemical Formula 1 is represented by any one of the following Chemical Formulas 10 to 20: [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 19] [Chemical Formula 20] In the formula, W is O or S; Y1 to Y2, Ar1 to Ar2, R1 to R4, o, p, q, and r are each the same as defined in claim 1.

10. The compound according to claim 1, wherein the compound represented by the Chemical Formula 1 is represented by any one of the following Chemical Formulas 21 to 28: [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 26] [Chemical Formula 27] [Chemical Formula 28] In the formula, Ring A is a monocyclic or polycyclic alicyclic ring, a monocyclic or polycyclic heteroalicyclic ring, a monocyclic or polycyclic aromatic ring, or a monocyclic or polycyclic heteroaromatic ring; X1 to X3, Y1 to Y2, Ar1 to Ar2, R1 to R4, o, p, q, and r are each the same as defined in claim 1.

11. The compound according to claim 1, wherein the compound represented by the Chemical Formula 1 is represented by any one of the following Chemical Formulas 29 to 31: [Chemical Formula 29] [Chemical Formula 30] [Chemical Formula 31] In the formula, X1 to X3, Y1 to Y2, Ar1 to Ar2, R1 to R4, o, p, q, and r are each the same as defined in claim 1.

12. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1 to 120:

13. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is a material for a light-emitting layer, an electron-transporting layer, or an electron-transporting auxiliary layer.

14. 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 contains the compound according to any one of claims 1 to 13.

15. The organic electroluminescent device according to claim 14, wherein the organic layer containing the compound is selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a lifetime improvement layer, an electron-transporting layer, and an electron-transporting auxiliary layer.

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