Organic compound and organic electroluminescent element using the same

Abstract

The present application relates to a novel compound having excellent carrier transportability, light emitting ability and thermal stability, and an organic electroluminescent element having improved characteristics such as luminous efficiency, driving voltage, lifespan, etc. by including the compound in one or more organic layers.

Description

Technical Field

[0001] This invention relates to a novel organic light-emitting compound and an organic electroluminescent element utilizing the same, and more specifically, to a compound with excellent electron transport capability, light emission capability and thermal stability, and an organic electroluminescent element whose luminous efficiency, driving voltage, lifetime and other characteristics are improved by including the compound in one or more organic layers. Background Technology

[0002] When a voltage is applied between the two electrodes of an organic electroluminescent device, 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, they form excitons. When these excitons transition to the ground state, they emit light. The materials used as the organic layer can be classified according to their function as light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials.

[0003] Luminescent materials can be categorized by their emission color into blue, green, and red luminescent materials, as well as yellow and orange luminescent materials used to achieve more natural colors. Furthermore, to improve luminescent efficiency through increased color purity and energy transfer, a host / dopant system can be used as the luminescent material.

[0004] Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal coordination compounds containing heavy atoms such as Ir and Pt. Since the development of phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescence, research is being vigorously pursued not only on phosphorescent dopants but also on phosphorescent host materials.

[0005] To date, NPB, BCP, and Alq3 are widely known materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives have been reported as luminescent layer materials. In particular, Ir-containing metal coordination compounds such as Firmic, Ir(ppy)3, and (acac)Ir(btp)2, which have advantages in improving efficiency, have been used as phosphorescent dopants for blue, green, and red light, while 4,4-dicarbazolybiphenyl (CBP) has been used as a phosphorescent host material.

[0006] However, while conventional organic layer materials offer advantages in terms of luminescence properties, their low glass transition temperature and poor thermal stability have resulted in unsatisfactory lifetime performance in organic electroluminescent devices. Therefore, there is a need to develop high-performance organic layer materials. Summary of the Invention

[0007] Technical issues

[0008] The technical challenge of this invention is to provide an organic layer material with excellent heat resistance, charge carrier transport capability, and light emission capability, which can be used as an organic electroluminescent element, specifically a novel compound that can be used as an electron transport layer, an electron transport auxiliary layer, or a light emission layer.

[0009] Furthermore, another technical challenge of the present invention is to provide an organic electroluminescent element that, by including the above-mentioned novel compound, has a low driving voltage, high luminous efficiency, and improved lifetime.

[0010] Other objects and advantages of the present invention can be more clearly set forth in the following detailed description of the invention and the claims.

[0011] Technical solution

[0012] To achieve the above objectives, 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 may be the same as or different from each other, and each is independently CR2 or N, wherein at least one of X1 to X3 is N.

[0017] R1 and R2 may be the same as or different from each other, and are independently chosen from hydrogen, deuterium (D), halogen, cyano, nitro, C1~C. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 ring atoms, C6~C 60 aryl, heteroaryl with 5 to 60 ring atoms, C1~C 40 alkoxy groups, C6~C 60 aryloxy group, C3~C 40 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide, C6~C 60 arylamine group, C5~C 60The R1 is a group consisting of aryl heteroarylamines and heteroarylamines with 5 to 60 ring atoms, or the R1 can be combined with any adjacent group to form a condensed ring that does not contain heteroatoms.

[0018] Ar1 to Ar5 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium (D), and C1 to C2. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 ring atoms, C6~C 60 aryl, heteroaryl with 5 to 60 ring atoms, C1~C 40 alkoxy groups, C6~C 60 aryloxy group, C3~C 40 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide, C6~C 60 arylamine group, C5~C 60 It is a group composed of aryl heteroarylamines and heteroarylamines with 5 to 60 ring atoms.

[0019] L is a single key or can be selected freely from C6 to C. 18 The group consists of arylene groups and heteroarylene groups with 5 to 18 ring atoms.

[0020] o and p are each an independent integer from 0 to 3.

[0021] The arylene and heteroarylene groups of L, and the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboronyl, arylboronyl, arylphosphinyl, arylphosphine oxide, and arylamine groups of R1~R2 and Ar1~Ar5 can each be independently selected from hydrogen, deuterium (D), halogen, cyano, nitro, C1~C1. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 ring atoms, C6~C 60 aryl, heteroaryl with 5 to 60 ring atoms, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 alkylsilyl, C6~C 60arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide, C6~C 60 arylamine group, C5~C 60 The substituted group is composed of one or more substituents from the group consisting of aryl heteroarylamines and heteroarylamines with 5 to 60 ring atoms, wherein when there are multiple substituents, they may be the same as or different from each other.

[0022] Furthermore, the present invention provides an organic electroluminescent element comprising an anode, a cathode, and one or more organic layers between the anode and the cathode, wherein at least one of the more than one organic layer comprises a compound represented by the above-described chemical formula 1.

[0023] Here, the organic layer comprising the compound represented by Chemical Formula 1 can be selected from the group consisting of a free-emission layer, an emission-assisted 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, a material comprising at least one of the following: the phosphorescent host material of the emission layer, the electron transport layer, and the electron transport auxiliary layer, comprising the compound represented by Chemical Formula 1.

[0024] The effects of the invention

[0025] According to an embodiment of the present invention, the compound represented by the above chemical formula 1 can be used as an organic layer material for organic electroluminescent elements due to its excellent electron transport capability, luminescence capability, and heat resistance.

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

[0027] Therefore, organic electroluminescent elements containing compounds represented by the above chemical formula 1 can be significantly improved in terms of excellent luminescence performance, low driving voltage, long lifespan and high efficiency, and can thus be effectively applied to full-color display panels, etc.

[0028] The effects of the present invention are not limited to those illustrated above, and this specification includes a wider variety of effects. Detailed Implementation

[0029] The present invention will now be described in detail.

[0030] <Novel Organic Compounds>

[0031] This invention provides a novel compound, such as a silane compound, that exhibits excellent electron transport capability and thermal stability, thereby simultaneously providing the characteristics of low driving voltage, high luminous efficiency, and long lifetime of the device.

[0032] Specifically, the novel organic compounds of the present invention contain silyl groups (e.g., tetraphenylsilane), carbazoyl groups and azazinyl groups (e.g., nitrogen-containing heteroaromatic rings) as essential components within the molecule, and have a basic skeleton with a phenyl group located on one side as the center, in which the azazinyl group and carbazoyl group (e.g., N) are directly linked or linked by a separate linking group (e.g., L).

[0033] Compounds having the structure of Formula 1 described above form a near-radial structure by simultaneously bonding an azazinyl group and a carbazole group (specifically, the N position of the carbazole group) to a benzene ring located on one side of the silane (e.g., tetraphenylsilane). Such compounds of the present invention not only possess high triplet (T1) energy levels derived from structural asymmetry and steric hindrance, but also further enhance the strong electron-withdrawing group (EWG) characteristics of the azazinyl group, thereby exhibiting physicochemical properties more suitable for electron injection and electron transport. This results in a synergistic effect that enhances the high efficiency of the device.

[0034] Furthermore, the aforementioned compounds, due to their structural characteristics of combining a dibenzo[a] group and a silane group with electron-donating (EDG) properties, and a nitrogen-containing aromatic ring (e.g., pyrazine, pyrimidine, triazine) of the azazine group, which is an electron-withdrawing (EWG) group, can induce polarization within the material, thereby generating a wide band gap. They also exhibit a wide distribution of HOMO and LUMO orbitals throughout the molecule. Therefore, when the compounds of Formula 1 are used as materials for electron transport layers or electron transport auxiliary layers, they can effectively receive electrons from the cathode, thus smoothly transferring electrons to the light-emitting layer, ultimately reducing the driving voltage of the device and inducing high efficiency and long lifetime characteristics. In particular, since the compounds of the present invention have an asymmetric structure, they do not have a crystallization temperature (Tc) in terms of thermal properties, thus offering advantages in terms of processability.

[0035] Furthermore, since the compound of Formula 1 must contain a silane (Si) moiety, it exhibits a high triplet (T1) energy value due to electron conjugation and steric hindrance. This not only defends against holes but also provides the capacity for quenching excessive exciton generation, thus preventing excitons generated in the luminescent layer from diffusing into the adjacent electron or hole transport layers. Additionally, the increased number of excitons contributing to luminescence within the luminescent layer improves the device's luminous efficiency, durability, and stability, effectively extending its lifetime. Simultaneously, the introduction of the silane moiety increases the molecular weight and ensures a high glass transition temperature (Tg), significantly improving heat resistance.

[0036] Furthermore, the compound represented by Formula 1 not only exhibits excellent electron transport capabilities but also demonstrates low driving voltage, high efficiency, and long lifetime. These superior electron transport properties enable high efficiency and fast mobility in organic electroluminescent devices, and the HOMO and LUMO energy levels can be easily tuned depending on the orientation or position of the substituents. Therefore, organic electroluminescent devices using these compounds can exhibit high electron transport capabilities.

[0037] According to the present invention, the compound represented by Formula 1 contains silyl, carbazole and azazinyl (e.g., nitrogen-containing heteroaromatic ring) as essential components in the molecule, and has a basic skeletal structure in which the N of the azazinyl and carbazole groups are directly connected or connected by separate linking groups (e.g., L) on a phenyl group located on one side of the silyl group.

[0038] The carbazole (e.g., an R1-containing ring) group directly attached to the central benzene ring of the compound represented by the above chemical formula 1 can be used without limitation from the conventional carbazole moiety known in the art.

[0039] At least one R1 can be substituted on one or both sides of the benzene ring of such a carbazole group. R1 is selected from hydrogen, deuterium (D), halogen, cyano, nitro, C1~C1. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 ring atoms, C6~C 60 aryl, heteroaryl with 5 to 60 ring atoms, C1~C 40 alkoxy groups, C6~C 60 aryloxy group, C3~C 40 alkylsilyl, C6~C 60arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide, C6~C 60 arylamine group, C5~C 60 The R1 group consists of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 ring atoms, or can be combined with any adjacent group to form a condensation ring without heteroatoms. Here, the condensation ring without heteroatoms is a monocyclic or polycyclic hydrocarbon ring group, including conventionally known condensed aliphatic rings, condensed aromatic rings, or combinations thereof. In this case, the heteroatom refers to an atom selected from the group consisting of N, O, and [missing information]. When there are multiple R1 groups, the multiple R1 groups can be the same or different from each other.

[0040] At this point, the molecule contains silyl groups, carbazole groups, and azazin groups (e.g., nitrogen-containing heteroaromatic rings). When the carbazole group combines with adjacent groups to form a condensed ring containing heteroatoms, the HOMO energy level decreases due to the expansion of the HOMO orbital, and the LUMO energy level also decreases accordingly. This makes it difficult to have a suitable LUMO energy level as an electron transport layer and / or electron transport auxiliary layer material. Furthermore, the triplet (T1) energy level becomes lower, so when an excess of triplet (T1) excitons is generated in the luminescent layer, there will be no longer any capacity for quenching.

[0041] In contrast, in this invention, since the molecule contains silyl, carbazole, and azazine groups (e.g., nitrogen-containing heteroaromatic rings), while the condensed ring derived from the carbazole group does not contain heteroatoms, the aforementioned problems are not fundamentally caused, and the material can exhibit properties suitable for use as an electron transport layer and / or an electron transport auxiliary layer material.

[0042] Specifically, R1 is selected from hydrogen, deuterium (D), and C1~C2. 40 Alkyl groups, C6~C 60 It consists of an aryl group and a heteroaryl group having 5 to 60 ring atoms, or it can combine with any adjacent group to form a condensed ring that does not contain heteroatoms. More specifically, it can be free of hydrogen, C6~C6 ... 40 It is a group composed of aryl groups and heteroaryl groups with 5 to 40 ring atoms.

[0043] In this case, the number of substitutions of R1 (e.g., p) can be an integer from 0 to 3. As an example, when p is 0, R1 can be hydrogen. Furthermore, when each p is greater than 0 and less than 3, the multiple R1s can be the same or different from each other, and each can independently be the other substituents in the definition of the aforementioned linking group except for the single bond.

[0044] In one specific example, the aforementioned carbazoyl group (e.g., a ring containing R1) can be embodied in any of the structural formulas selected below. However, it is not limited thereto.

[0045]

[0046] In the above formula,

[0047] * refers to the part connected to chemical formula 1 above.

[0048] Ring A is a monocyclic or polycyclic hydrocarbon cyclic group that does not contain heteroatoms, and multiple rings A may be the same as or different from each other.

[0049] R1 and p are each as defined in chemical formula 1.

[0050] In a preferred embodiment, the carbazoyl group (e.g., an R1-containing ring) may be further specified as any of the following structural formulas.

[0051]

[0052] In the above formula,

[0053] * refers to the part connected to chemical formula 1 above.

[0054] R1 and p are each as defined in Formula 1. Furthermore, although not shown in the aforementioned structural formula, they may be replaced by at least one substituent known in the art (e.g., the same as the definition of R1).

[0055] The other of the three substituents attached to the central benzene ring is a nitrogen-containing heterocycle (e.g., a ring containing X1 to X3), which is a monocyclic nitrogen-containing heteroaryl group containing at least one nitrogen atom. As an example of a nitrogen-containing heteroaromatic ring, X1 to X3 may be the same as or different from each other, each independently being C(R2) or N, wherein at least one of X1 to X3 contains N. Preferably, it contains 2 to 3 N atoms. Thus, by including a heterocycle containing 2 to 3 nitrogen atoms, superior electron absorption characteristics are exhibited, thereby facilitating electron injection and transport.

[0056] Here, R2 is selected from hydrogen, deuterium (D), halogen, cyano, nitro, C1~C. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 ring atoms, C6~C 60 aryl, heteroaryl with 5 to 60 ring atoms, C1~C 40 alkoxy groups, C6~C 60 aryloxy group, C3~C 40 alkylsilyl, C6~C60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide, C6~C 60 arylamine group, C5~C 60 It consists of aryl heteroarylamine groups and heteroarylamine groups with 5 to 60 ring atoms. In this case, multiple R2 groups can be the same or different from each other. Specifically, R2 is preferably free from hydrogen, deuterium, C1~C2. 40 Alkyl groups, C6~C 60 It is a group consisting of aryl groups and heteroaryl groups with 5 to 60 ring atoms.

[0057] In one specific example, the nitrogen-containing heterocycle (e.g., a ring containing X1 to X3) may be more specifically selected from any of the following structural formulas. However, it is not limited thereto.

[0058]

[0059] In the above formula,

[0060] * refers to the part connected to chemical formula 1 above.

[0061] R2, Ar4 and Ar5 are each defined as in chemical formula 1.

[0062] Various substituents, Ar4 and Ar5, can be substituted onto the aforementioned nitrogen-containing heterocycles (e.g., rings containing X1 to X3). Ar4 and Ar5 can be the same or different from each other, and are independently selected from hydrogen, deuterium (D), C1 to C2. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 ring atoms, C6~C 60 aryl, heteroaryl with 5 to 60 ring atoms, C1~C 40 alkoxy groups, C6~C 60 aryloxy group, C3~C 40 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide, C6~C 60 arylamine group, C5~C 60It is a group composed of aryl heteroarylamines and heteroarylamines with 5 to 60 ring atoms. Specifically, Ar4 and Ar5 can be the same as or different from each other, and are each independently selected from C6 to C5. 60 The group consisting of aryl groups and heteroaryl groups having 5 to 60 ring atoms, more specifically preferably free C6~C6. 40 It is a group composed of aryl groups and heteroaryl groups with 5 to 40 ring atoms.

[0063] In a specific example, Ar4 and Ar5 may be the same as or different from each other, and each may be independently specified as any of the following structural formulas. However, it is not limited to this.

[0064]

[0065]

[0066] In the above formula,

[0067] * refers to the part connected to chemical formula 1 above.

[0068] R4 is selected from hydrogen, deuterium (D), and C1~C. 40 Alkyl groups, C6~C 60 It consists of aryl groups and heteroaryl groups having 5 to 60 ring atoms. Furthermore, although not shown in the foregoing structural formula, it may be replaced by at least one substituent known in the art (e.g., the same as the R1 definition).

[0069] Another of the three substituents attached to the central benzene ring is a silane moiety (e.g., -SiAr1Ar2Ar3). Such a silane moiety can be substituted with substituents Ar1 to Ar3, which may be identical or different from each other, and are independently selected from hydrogen, deuterium (D), and C1-C2. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 ring atoms, C6~C 60 aryl, heteroaryl with 5 to 60 ring atoms, C1~C 40 alkoxy groups, C6~C 60 aryloxy group, C3~C 40 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60The group is composed of aryl amino groups. Specifically, Ar1 to Ar3 may be the same as or different from each other, and each can be independently selected from C6 to C3. 60 The group consisting of aryl groups and heteroaryl groups with 5 to 60 ring atoms, more specifically C6~C6. 40 Aryl groups.

[0070] In one specific example, Ar1 to Ar3 can each be the same as the aforementioned specific examples of Ar4 to Ar5. As a preferred specific example, the group consisting of free phenyl, biphenyl and terphenyl can be selected.

[0071] In the compounds represented by Formula 1 of the present invention, the central benzene ring and the azazinyl group (e.g., a ring containing X1 to X3) can be directly linked or bonded through a separate linking group (e.g., L). When such a separate linking group (L) is present, the HOMO region is expanded, which is beneficial to the HOMO-LUMO distribution, and the charge transfer efficiency can be improved through appropriate overlap of HOMO-LUMO.

[0072] Such a linker (L) can be a commonly known divalent linker in the art. Specifically, L is a single bond or can be chosen from C6 to C6. 18 It consists of a group of arylene groups and heteroarylene groups with 5 to 18 ring atoms. More specifically, it can be a single bond or selected from C6 to C6. 12 It is a group composed of arylene groups and heteroarylene groups with 5 to 12 ring atoms.

[0073] Here, the number o of the linking groups L is an integer from 0 to 3. When o is 0, L is a single bond (direct bonding); when o is 1 to 3, it can have one or more substituents selected from the group consisting of arylene and heteroarylene groups, excluding single bonds, as defined in the aforementioned linking group definition. In this case, when there are multiple Ls, even if they are represented identically in chemical formula, they can be the same or different from each other.

[0074] Specific examples of the aforementioned arylene linking groups and heteroarylene linking groups include phenylene, biphenylene, naphthylene, anthracene, indenylene, pyranthraylene, carbazolyl, thiophene, indoleylene, purine, quinolinyl, pyrrolyl, imidazolyl, oxazolyl, thiazolyl, pyridinyl, pyrimidinyl, dibenzofuran moiety, dibenzothiophene moiety, and / or dibenzoselenophene moiety. More specifically, phenylene, biphenylene, or terphenylene are preferred.

[0075] In a specific example, L1 to L2 may be the same or different from each other, and each can independently be a linking base selected from the following structural formulas.

[0076]

[0077] In the above formula,

[0078] * refers to the site connected to the above chemical formula 1. Furthermore, although not shown in the aforementioned structural formula, it may be replaced by at least one substituent known in the art (e.g., the same as the definition of R1).

[0079] In the aforementioned chemical formula 1, the arylene or heteroarylene of L, and the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboronyl, arylboronyl, arylphosphinyl, arylphosphine oxide, and arylamine groups of R1~R2 and Ar1~Ar5 can each be independently selected from hydrogen, deuterium (D), halogen, cyano, nitro, C1~C1~C2, C1~C1~C2~Ar5. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 ring atoms, C6~C 60 aryl, heteroaryl with 5 to 60 ring atoms, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide, C6~C 60 arylamine group, C5~C 60 The substituted group is composed of one or more substituents from the group consisting of aryl heteroarylamines and heteroarylamines with 5 to 60 ring atoms, wherein when there are multiple substituents, they may be the same as or different from each other.

[0080] According to one embodiment of the present invention, the compound represented by the above-described chemical formula 1 may be further specified as any one of the following chemical formulas 2 to 6, depending on the type of nitrogen-containing heteroaromatic ring (e.g., rings containing X1 to X3). However, it is not limited thereto.

[0081] [Chemical Formula 2]

[0082]

[0083] [Chemical Formula 3]

[0084]

[0085] [Chemical Formula 4]

[0086]

[0087] [Chemical Formula 5]

[0088]

[0089] [Chemical Formula 6]

[0090]

[0091] Among the above chemical formulas 2 to 6,

[0092] Ar1~Ar5, L, R1, o and p are each defined as in chemical formula 1.

[0093] According to another embodiment of the invention, the compound represented by the above-described chemical formula 1 may be further specified as any one of the following chemical formulas 7 to 9, depending on the type of Ar4 to Ar5 substituents introduced onto the nitrogen-containing heteroaromatic ring (e.g., a ring containing X1 to X3). However, it is not limited thereto.

[0094] [Chemical Formula 7]

[0095]

[0096] [Chemical Formula 8]

[0097]

[0098] [Chemical Formula 9]

[0099]

[0100] Of the above chemical formulas 7 to 9,

[0101] Z1 is O or S.

[0102] Z2 is N,

[0103] R 11 Choose freely from hydrogen, deuterium (D), and C1~C 40 Alkyl groups, C6~C 60 It is a group consisting of aryl groups and heteroaryl groups with 5 to 60 ring atoms, or it can combine with any adjacent group to form a condensation ring.

[0104] m is an integer from 0 to 3.

[0105] a is an integer from 1 to 3.

[0106] X1~X3, Ar1~Ar3, L, R1, o, and p are each defined as in chemical formula 1.

[0107] According to another embodiment of the invention, the compound represented by the above-described chemical formula 1 may be further specified as any one of chemical formulas 10 to 13, depending on the binding position of the R1 substituent introduced onto the carbazole group. However, it is not limited thereto.

[0108] [Chemical Formula 10]

[0109]

[0110] [Chemical Formula 11]

[0111]

[0112] [Chemical Formula 12]

[0113]

[0114] [Chemical Formula 13]

[0115]

[0116] In the above chemical formulas 10 to 13,

[0117] X1~X3, Ar1~Ar5, L, R1, o and p are each defined as in chemical formula 1.

[0118] According to another embodiment of the present invention, the compound represented by the above-described chemical formula 1 may be further specified as any one of the following chemical formulas 14 to 23, depending on the bonding position of the condensation ring formed on the carbazole group. However, it is not limited thereto.

[0119] [Chemical Formula 14]

[0120]

[0121] [Chemical Formula 15]

[0122]

[0123] [Chemical Formula 16]

[0124]

[0125] [Chemical Formula 17]

[0126]

[0127] [Chemical Formula 18]

[0128]

[0129] [Chemical Formula 19]

[0130]

[0131] [Chemical Formula 20]

[0132]

[0133] [Chemical Formula 21]

[0134]

[0135] [Chemical Formula 22]

[0136]

[0137] [Chemical Formula 23]

[0138]

[0139] Among the above chemical formulas 14 to 23,

[0140] Ring A can be a monocyclic or polycyclic hydrocarbon cyclic group with 5 to 24 carbon atoms that does not contain heteroatoms, specifically a hydrocarbon cyclic group with 6 to 18 carbon atoms. Multiple rings A may be the same or different from each other.

[0141] X1~X3, Ar1~Ar5, L, R1, o and p are each defined as in chemical formula 1.

[0142] According to another embodiment of the invention, the compound represented by the above-described chemical formula 1 may be more specifically specified as any one of chemical formulas 24 to 29, depending on the bonding position of the carbazoyl or azazinyl group attached to the central benzene ring located on the other side of the silane (e.g., -Si-Ar1Ar2Ar3-). However, it is not limited thereto.

[0143] [Chemical Formula 24]

[0144]

[0145] [Chemical Formula 25]

[0146]

[0147] [Chemical Formula 26]

[0148]

[0149] [Chemical Formula 27]

[0150]

[0151] [Chemical Formula 28]

[0152]

[0153] [Chemical Formula 29]

[0154]

[0155] In the above chemical formulas 24 to 29,

[0156] X1~X3, Ar1~Ar5, L, R1, o and p are each defined as in chemical formula 1.

[0157] According to another embodiment of the present invention, the compound represented by the above-described chemical formula 1 may be further specified as any one of the following chemical formulas 30 to 39, depending on the bonding positions of the carbazoyl group and the azazinyl group simultaneously attached to the central benzene ring. However, it is not limited thereto.

[0158] [Chemical Formula 30]

[0159]

[0160] [Chemical Formula 31]

[0161]

[0162] [Chemical Formula 32]

[0163]

[0164] [Chemical Formula 33]

[0165]

[0166] [Chemical Formula 34]

[0167]

[0168] [Chemical Formula 35]

[0169]

[0170] [Chemical Formula 36]

[0171]

[0172] [Chemical Formula 37]

[0173]

[0174] [Chemical Formula 38]

[0175]

[0176] [Chemical Formula 39]

[0177]

[0178] Among the above chemical formulas 30 to 39,

[0179] X1~X3, Ar1~Ar5, L, R1, o and p are each defined as in chemical formula 1.

[0180] The compounds represented by Chemical Formula 1 of the present invention described above can be more specifically represented by any one of the compounds 1 to 137 exemplified below. However, the compounds represented by Chemical Formula 1 of the present invention are not limited to those exemplified below.

[0181]

[0182]

[0183]

[0184]

[0185] In this invention, "ring atom number" refers to the number of ring atoms that constitute the ring structure. These ring atoms can be carbon atoms or heteroatoms selected from the group consisting of N, O, S, and Se. As an example, the ring atom number of pyridine means that it includes 5 C atoms and 1 N atom constituting the pyridine ring, totaling 6.

[0186] In this invention, "alkyl" refers to a monovalent substituent derived from a straight-chain or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of substituents include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, etc., but are not limited thereto.

[0187] In this invention, "alkenyl" refers to a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon double bonds. Examples of alkenyl include vinyl, allyl, isopropenyl, and 2-butenyl, but it is not limited thereto.

[0188] In this invention, "alkynyl" refers to a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon triple bonds. Examples of alkynyl and 2-propynyl are provided, but the invention is not limited to these.

[0189] In this invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon with 6 to 40 carbon atoms, consisting of a single ring or a combination of two or more rings. Furthermore, it may also include forms where two or more rings are simply attached to or condensed together. Examples of such aryl groups include phenyl, naphthyl, phenanthryl, anthracene, etc., but are not limited thereto.

[0190] In this invention, "heteroaryl" refers to a monovalent substituent derived from a mono- or poly-heterocyclic aromatic hydrocarbon with 5 to 40 ring atoms. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are replaced by heteroatoms such as N, O, S, and Se. Furthermore, it may also include forms where two or more rings are simply attached to or condensed together, and further, forms condensed with an aryl group. Examples of such heteroaryl groups include six-membered monocyclic groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic groups such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isooxazolyl, 2-pyridinyl, and 2-pyrimidinyl, but are not limited thereto.

[0191] In this invention, "aryloxy group" is a monovalent substituent represented by RO-, where R refers to an aryl group with 5 to 40 carbon atoms. Examples of such aryloxy groups include phenoxy, naphthoxy, and diphenoxy groups, but are not limited thereto.

[0192] In this invention, "alkoxy" is a monovalent substituent represented by R'O-, where R' refers to an alkyl group having 1 to 40 carbon atoms, which may include linear, branched, or cyclic structures. Examples of alkoxy groups include methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, pentoxy, etc., but are not limited thereto.

[0193] In this invention, "arylamine" refers to an amine group that is replaced by an aryl group having 6 to 40 carbon atoms.

[0194] In this 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 cycloalkyl groups include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine, but are not limited thereto.

[0195] In this invention, "heterocyclic alkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon with 3 to 40 ring atoms, wherein one or more carbons in the ring, preferably 1 to 3 carbons, are substituted by heteroatoms such as N, O, S, or Se. Examples of such heterocyclic alkyl groups include morpholinoyl and piperazine, but are not limited thereto.

[0196] In this invention, "alkylsilyl" means silyl substituted with an alkyl group having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with an aryl group having 5 to 40 carbon atoms.

[0197] In this invention, "condensed ring" refers to a morphology consisting of condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or combinations thereof.

[0198] <Electron Transport Layer Materials>

[0199] The present invention provides an electron transport layer comprising the compound represented by the above chemical formula 1.

[0200] The electron transport layer (ETL) serves to move electrons injected from the cathode to adjacent layers, specifically to the light-emitting layer.

[0201] The compound represented by the above chemical formula 1 can be used alone as an electron transport layer (ETL) material, or it can be used in combination with electron transport layer materials known in the art. It is preferred to use it alone.

[0202] Electron transport layer materials that can be mixed with compounds of Formula 1 include electron transport substances generally known in the art. Non-limiting examples of usable electron transport substances include oxazole compounds, isoxazole 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. They can be used alone or in combination of two or more.

[0203] In this invention, when the compound of the above chemical formula 1 is mixed with the electron transport layer material, there is no particular limitation on their mixing ratio, which can be appropriately adjusted within the range known in the art.

[0204] <Electron Transport Auxiliary Layer Materials>

[0205] Furthermore, the present invention provides an electron transport auxiliary layer comprising the compound represented by the above chemical formula 1.

[0206] The electron transport auxiliary layer is disposed 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.

[0207] The compound represented by the above chemical formula 1 can be used alone as an electron transport auxiliary layer material, or it can be used in combination with electron transport auxiliary layer materials known in the art. It is preferred to use it alone.

[0208] Electron transport auxiliary layer materials that can be used in conjunction with compounds of Formula 1 include electron transport substances generally known in the art. As an example, the electron transport auxiliary layer may comprise oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), nitrogen-containing heterocyclic derivatives, etc.

[0209] In this invention, when the compound of the above chemical formula 1 is mixed with the electron transport auxiliary layer material, there is no particular limitation on their mixing ratio, which can be appropriately adjusted within the range known in the art.

[0210] Organic electroluminescent elements

[0211] On the other hand, another aspect of the present invention relates to an organic electroluminescent element (organic EL element) comprising the compound represented by the above-described chemical formula 1 of the present invention.

[0212] Specifically, the present invention is an organic electroluminescent element comprising an anode, a cathode, and one or more organic layers between the anode and the cathode, wherein at least one of the organic layers comprises a compound represented by chemical formula 1 above. In this case, the compound may be used alone or in combination of two or more.

[0213] The aforementioned 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, wherein at least one organic layer contains a compound represented by Chemical Formula 1. Specifically, the organic layer containing the compound of Chemical Formula 1 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 preferably an electron transport layer or an electron transport auxiliary layer.

[0214] The light-emitting layer of the organic electroluminescent element of the present invention comprises a host material and a dopant material, wherein the host material may be a compound of the aforementioned chemical formula 1. Furthermore, the light-emitting layer of the present invention may comprise compounds known in the art, other than those of the aforementioned chemical formula 1, as the host material.

[0215] When a compound represented by the above-described chemical formula 1 is used as the light-emitting layer material of an organic electroluminescent element, preferably as a blue, green, or red phosphorescent host material, the efficiency (luminous efficiency and power efficiency), lifetime, brightness, and driving voltage of the organic electroluminescent element can be improved due to the increased binding force between holes and electrons in the light-emitting layer. Specifically, the compound represented by the above-described chemical formula 1 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 with a highly efficient light-emitting layer.

[0216] The structure of the organic electroluminescent element of the present invention is not particularly limited, and can 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, hole transport layer, light-emitting auxiliary layer, light-emitting layer, electron transport layer, and electron injection layer may contain a compound represented by Chemical Formula 1, preferably the light-emitting layer, and more preferably the phosphorescent host may contain a compound represented by Chemical Formula 1. Alternatively, an electron injection layer may be further stacked on top of the electron transport layer.

[0217] The organic electroluminescent element of the present invention can be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0218] In the organic electroluminescent element of the present invention, one or more of the aforementioned organic layers contain the compound represented by the above-mentioned chemical formula 1. In addition, the organic layers and electrodes can be formed and manufactured using materials and methods known in the art.

[0219] The aforementioned organic layer can be formed by vacuum evaporation or solution coating. Examples of solution coating methods include spin coating, dip coating, doctor blade coating, inkjet printing, or thermal transfer, but are not limited to these.

[0220] The substrate used in manufacturing the organic electroluminescent element of the present invention is not particularly limited, and can be silicone wafers, quartz, glass plates, metal plates, plastic films and sheets, etc.

[0221] Furthermore, the anode material can be any anode material known in the art without restriction. Examples include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; 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-(ethylidene-1,2-dioxothiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but not limited thereto.

[0222] Furthermore, cathode materials known in the art can be used without restriction. Examples include metals or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead; and multilayer materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0223] Furthermore, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and commonly known materials in the art can be used without restriction.

[0224] The present invention will be described in detail below through embodiments. However, the following embodiments are merely illustrative of the present invention, and the present invention is not limited to the following embodiments.

[0225] [Preparation Example 1]

[0226] <Step 1> 9-(3-chloro-5-(triphenylsilyl)phenyl)-9H-carbazole (9-(3-chloro-5- Synthesis of (triphenylsilyl)phenyl)-9H-carbazole)

[0227]

[0228] 30 g (66.7 mmol) of (3-bromo-5-chlorophenyl)triphenylsilane, 12.3 g (73.4 mmol) of 9H-carbazole, and 12.8 g (133.4 mmol) of NaOtBu were added to 600 mL of xylene, and the mixture was refluxed and stirred for 8 hours. After the reaction was completed, the mixture was cooled to room temperature and then extracted with dichloromethane and H2O. The organic layer was anhydrouslyzed with MgSO4 and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography to give 26.8 g (75% yield) of 9-(3-chloro-5-(triphenylsilyl)phenyl)-9H-carbazole.

[0229] Mass spectrometry: [(M+H)] + ]:535.15

[0230] <Step 2> Synthesis of Intermediate 1

[0231]

[0232] 26.8 g (50.0 mmol) of 9-(3-chloro-5-(triphenylsilyl)phenyl)-9H-carbazole, 25.4 g (100.0 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)), 1.8 g (2.5 mmol) of PdCl2(dppf), 2.4 g (5.0 mmol) of Xphos, and 14.7 g (150.0 mmol) of KOAc were dissolved in 500 ml of 1,4-dioxane, and the mixture was refluxed and stirred for 8 hours to carry out the reaction. After the reaction was completed, the mixture was cooled to room temperature, and then the solid (KOAc) was filtered off. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain 27.6 g of intermediate 1 (yield 88%).

[0233] Mass spectrometry: [(M+H)] + ]:627.67

[0234] [Preparation Example 2]

[0235] <Step 1> 9-(5-chloro-2-(triphenylsilyl)phenyl)-9H-carbazole (9-(5-chloro-2- Synthesis of (triphenylsilyl)phenyl)-9H-carbazole)

[0236]

[0237] 30 g (66.7 mmol) of (2-bromo-4-chlorophenyl)triphenylsilane, 12.3 g (73.4 mmol) of 9H-carbazole, and 12.8 g (133.4 mmol) of NaOtBu were added to 600 mL of toluene, and the mixture was refluxed and stirred for 8 hours. After the reaction was completed, the mixture was cooled to room temperature and then extracted with dichloromethane and H2O. The organic layer was anhydrouslyzed with MgSO4 and filtered. The filtrate was concentrated under reduced pressure and subjected to column chromatography to obtain 24.7 g of 9-(5-chloro-2-(triphenylsilyl)phenyl)-9H-carbazole (yield 69%).

[0238] Mass spectrometry: [(M+H)] + ]:535.15

[0239] <Step 2> Synthesis of Intermediate 2

[0240]

[0241] 24.7 g (46.1 mmol) of 9-(5-chloro-2-(triphenylsilyl)phenyl)-9H-carbazole, 23.4 g (92.1 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborhecyclopentane), 1.7 g (2.3 mmol) of PdCl2 (dppf), 2.2 g (4.6 mmol) of Xphos, and 13.6 g (138.3 mmol) of KOAc were dissolved in 500 mL of 1,4-dioxane, and the mixture was refluxed and stirred for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, and the solid (KOAc) was filtered off. The filtrate was distilled under reduced pressure and purified by column chromatography to give 24.0 g of intermediate 2 (yield 83%).

[0242] Mass spectrometry: [(M+H)] + ]:627.67

[0243] [Preparation Example 3]

[0244] <Step 1> 9-(2-chloro-4-(triphenylsilyl)phenyl)-9H-carbazole (9-(2-chloro-4-) Synthesis of (triphenylsilyl)phenyl)-9H-carbazole)

[0245]

[0246] 30 g (66.7 mmol) of (4-bromo-3-chlorophenyl)triphenylsilane, 12.3 g (73.4 mmol) of 9H-carbazole, and 12.8 g (133.4 mmol) of NaOtBu were added to 600 mL of xylene, and the mixture was refluxed and stirred for 8 hours. After the reaction was completed, the mixture was cooled to room temperature and then extracted with dichloromethane and H2O. The organic layer was anhydrouslyzed with MgSO4 and filtered. The filtrate was concentrated under reduced pressure and subjected to column chromatography to obtain 29.0 g of 9-(2-chloro-4-(triphenylsilyl)phenyl)-9H-carbazole (yield 81%).

[0247] Mass spectrometry: [(M+H)] + ]:535.15

[0248] <Step 2> Synthesis of Intermediate 3

[0249]

[0250] 29.0 g (54.1 mmol) of 9-(2-chloro-4-(triphenylsilyl)phenyl)-9H-carbazole, 27.5 g (108.2 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborhecyclopentane), 2.0 g (2.7 mmol) of PdCl2(dppf), 2.6 g (5.4 mmol) of Xphos, and 15.9 g (162.3 mmol) of KOAc were dissolved in 500 mL of 1,4-dioxane, and the mixture was refluxed and stirred for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, and the solid (KOAc) was filtered off. The filtrate was distilled under reduced pressure and purified by column chromatography to give 30.6 g of intermediate 3 (yield 90%).

[0251] Mass spectrometry: [(M+H)] + ]:627.67

[0252] [Preparation Example 4]

[0253] <Step 1> 9-(3-chloro-5-(triphenylsilyl)phenyl)-3-phenyl-9H-carbazole (9-(3-chloro-5- Synthesis of (triphenylsilyl)phenyl)-3-phenyl-9H-carbazole)

[0254]

[0255] 30 g (66.7 mmol) of (3-bromo-5-chlorophenyl)triphenylsilane, 17.8 g (73.4 mmol) of 3-phenyl-9H-carbazole, and 12.8 g (133.4 mmol) of NaOtBu were added to 600 mL of xylene, and the mixture was refluxed and stirred for 8 hours. After the reaction was completed, the mixture was cooled to room temperature and then extracted with dichloromethane and H2O. The organic layer was anhydrouslyzed with MgSO4 and filtered. The filtrate was concentrated under reduced pressure and column chromatography was used to obtain 31.8 g of 9-(3-chloro-5-(triphenylsilyl)phenyl)-3-phenyl-9H-carbazole (yield 78%).

[0256] Mass spectrometry: [(M+H)] + ]:611.18

[0257] <Step 2> Synthesis of Intermediate 4

[0258]

[0259] 31.8 g (51.9 mmol) of 9-(3-chloro-5-(triphenylsilyl)phenyl)-3-phenyl-9H-carbazole, 26.4 g (103.9 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborhecyclopentane), 1.9 g (2.6 mmol) of PdCl2(dppf), 2.5 g (5.2 mmol) of Xphos, and 15.3 g (155.8 mmol) of KOAc were dissolved in 500 mL of 1,4-dioxane, and the mixture was refluxed and stirred for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, and the solid (KOAc) was filtered off. The filtrate was distilled under reduced pressure and purified by column chromatography to give 32.1 g of intermediate 4 (yield 88%).

[0260] Mass spectrometry: [(M+H)] + ]:703.31

[0261] [Synthesis Example 1] Synthesis of Compound 1

[0262]

[0263] Intermediate 1 (25.8 g, 41.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (10 g, 37.4 mmol), Pd(PPh3)4 (2.2 g, 1.9 mmol), and K2CO3 (10.3 g, 74.7 mmol) were added to 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O, and stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain target compound 1 (20.0 g, yield 73%).

[0264] Mass spectrometry: [(M+H)] + ]:732.27

[0265] [Synthesis Example 2] Synthesis of Compound 2

[0266]

[0267] Intermediate 2 (25.8 g, 41.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (10 g, 37.4 mmol), Pd(PPh3)4 (2.2 g, 1.9 mmol), and K2CO3 (10.3 g, 74.7 mmol) were added to 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O, and stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain target compound 2 (21.9 g, yield 80%).

[0268] Mass spectrometry: [(M+H)] + ]:732.27

[0269] [Synthesis Example 3] Synthesis of Compound 3

[0270]

[0271] Intermediate 3 (25.8 g, 41.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (10 g, 37.4 mmol), Pd(PPh3)4 (2.2 g, 1.9 mmol), and K2CO3 (10.3 g, 74.7 mmol) were added to 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O, and stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain target compound 3 (19.4 g, yield 71%).

[0272] Mass spectrometry: [(M+H)] + ]:732.27

[0273] [Synthetic Example 4] Synthesis of Compound 4

[0274]

[0275] Intermediate 1 (25.9 g, 41.2 mmol), 4-chloro-2,6-diphenylpyrimidine (10 g, 37.5 mmol), Pd(PPh3)4 (2.2 g, 1.9 mmol), and K2CO3 (10.4 g, 75.0 mmol) were added to 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O, and stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain target compound 4 (20.6 g, yield 75%).

[0276] Mass spectrometry: [(M+H)] + ]:731.28

[0277] [Synthesis Example 5] Synthesis of Compound 16

[0278]

[0279] Intermediate 4 (28.9 g, 41.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (10 g, 37.4 mmol), Pd(PPh3)4 (2.2 g, 1.9 mmol), and K2CO3 (10.3 g, 74.7 mmol) were added to 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O, and stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain target compound 16 (22.7 g, yield 75%).

[0280] Mass spectrometry: [(M+H)] + ]:808.30

[0281] [Synthetic Example 6] Synthesis of Compound 25

[0282]

[0283] Intermediate 1 (20.1 g, 32.0 mmol), 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine) (10 g, 29.1 mmol), Pd(PPh3)4 (1.7 g, 1.5 mmol), and K2CO3 (8.0 g, 58.2 mmol) were added to 200 mL of toluene / 50 mL of EtOH / 50 mL of H2O, and stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound 25 (28.4 g, yield 78%).

[0284] Mass spectrometry: [(M+H)] + ]:808.30

[0285] [Synthetic Example 7] Synthesis of Compound 31

[0286]

[0287] Intermediate 1 (19.3 g, 30.7 mmol), 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (10 g, 27.9 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol), and K2CO3 (7.7 g, 55.9 mmol) were added to 200 mL of toluene / 50 mL of EtOH / 50 mL of H2O and stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain target compound 31 (17.3 g, yield 75%).

[0288] Mass spectrometry: [(M+H)] + ]:822.28

[0289] [Synthetic Example 8] Synthesis of Compound 34

[0290]

[0291] Intermediate 1 (19.3 g, 30.7 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (10 g, 27.9 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol), and K2CO3 (7.7 g, 55.9 mmol) were added to 200 mL of toluene / 50 mL of EtOH / 50 mL of H2O and stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain target compound 34 (16.8 g, yield 73%).

[0292] Mass spectrometry: [(M+H)] + ]:822.28

[0293] [Synthetic Example 9] Synthesis of Compound 37

[0294]

[0295] Intermediate 1 (19.3 g, 30.7 mmol), 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (10 g, 27.9 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol), and K2CO3 (7.7 g, 55.9 mmol) were added to 200 mL toluene / 50 mL EtOH / 50 mL H2O and stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain target compound 37 (18.6 g, yield 81%).

[0296] Mass spectrometry: [(M+H)] + ]:822.28

[0297] [Synthetic Example 10] Synthesis of Compound 40

[0298]

[0299] Intermediate 1 (19.3 g, 30.7 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (10 g, 27.9 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol), and K2CO3 (7.7 g, 55.9 mmol) were added to 200 mL of toluene / 50 mL of EtOH / 50 mL of H2O and stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound 40 (16.3 g, yield 71%).

[0300] Mass spectrometry: [(M+H)] + ]:822.28

[0301] [Synthetic Example 11] Synthesis of Compound 64

[0302]

[0303] Intermediate 1 (19.4 g, 30.8 mmol), 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole (10 g, 28.0 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol), and K2CO3 (7.7 g, 56.1 mmol) were added to 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O, and stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound 64 (17.0 g, yield 74%).

[0304] Mass spectrometry: [(M+H)] + ]:821.30

[0305] [Synthetic Example 12] Synthesis of Compound 104

[0306]

[0307] Intermediate 1 (15.9 g, 25.4 mmol), 9-(4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazin-2-yl)-9H-carbazole (10 g, 23.1 mmol), Pd(PPh3)4 (1.3 g, 1.2 mmol), and K2CO3 (6.4 g, 46.2 mmol) were added to 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O, and stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound 104 (16.2 g, yield 78%).

[0308] Mass spectrometry: [(M+H)] + ]:897.33

[0309] [Synthetic Example 13] Synthesis of Compound 110

[0310]

[0311] Intermediate 1 (18.5 g, 29.4 mmol), 2-chloro-4-(dibenzo[b,d]thiophen-2-yl)-6-phenyl-1,3,5-triazine (10 g, 26.7 mmol), Pd(PPh3)4 (1.5 g, 1.3 mmol), and K2CO3 (7.4 g, 53.5 mmol) were added to 200 mL of toluene / 50 mL of EtOH / 50 mL of H2O and stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound 110 (16.8 g, yield 75%).

[0312] Mass spectrometry: [(M+H)] + ]:838.26

[0313] [Synthetic Example 14] Synthesis of Compound 114

[0314]

[0315] Intermediate 1 (15.9 g, 25.4 mmol), 2-chloro-4-phenyl-6-(8-phenyldibenzo[b,d]furan-2-yl)-1,3,5-triazine (10 g, 23.0 mmol), Pd(PPh3)4 (1.4 g, 1.2 mmol), and K2CO3 (6.4 g, 46.1 mmol) were added to 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O, and stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound 114 (16.4 g, yield 79%).

[0316] Mass spectrometry: [(M+H)] + ]:898.31

[0317] [Synthetic Example 15] Synthesis of Compound 116

[0318]

[0319] Intermediate 1 (15.9 g, 25.4 mmol), 2-chloro-4-phenyl-6-(4-phenyldibenzo[b,d]furan-2-yl)-1,3,5-triazine (10 g, 23.0 mmol), Pd(PPh3)4 (1.4 g, 1.2 mmol), and K2CO3 (6.4 g, 46.1 mmol) were added to 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O, and stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound 116 (14.7 g, yield 71%).

[0320] Mass spectrometry: [(M+H)] + ]:898.31

[0321] [Examples 1-15] Fabrication of Blue Organic Electroluminescent Element

[0322] After refining compounds 1 to 116 synthesized in the above synthesis examples to high purity using commonly known methods, blue organic electroluminescent elements were prepared as follows.

[0323] A glass substrate coated with an indium tin oxide (ITO) film at a thickness of 1500 Å was ultrasonically washed with distilled water. After washing with distilled water, it was ultrasonically washed with solvents such as isopropanol, acetone, and methanol, and then dried. It was then transferred to a UV ozone cleaner (Power sonic 405, Hwashintech), where it was cleaned with UV light for 5 minutes. Finally, the substrate was transferred to a vacuum evaporation machine.

[0324] Organic electroluminescent elements were fabricated by stacking the following compounds on the prepared ITO transparent electrode in the order of HT-1 + 2% HAT-CN (100Å) / HT-1 (1400Å) / HT-2 (50Å) / BH + 2% BD (200Å) / ET-2 (50Å) / each of the compounds 1-116 in Table 1 below:LiQ = 1:1 (300Å) / LiF (10Å) / Al (1000Å).

[0325] The structures of the compounds HT-1, HAT-CN, HT-2, BH, BD, ET-1, ET-2 and LiQ used at this time are as follows.

[0326]

[0327]

[0328]

[0329] [Comparative Example 1] Fabrication of a blue organic electroluminescent element

[0330] As the electron transport layer material, ET-1, instead of compound 1, was deposited at 300 Å. Otherwise, the same procedure as described in Example 1 above was followed to fabricate the blue organic electroluminescent element of Comparative Example 1.

[0331] [Evaluation Example 1]

[0332] The current density of each blue organic electroluminescent element prepared in Examples 1 to 15 and Comparative Example 1 was measured at 10 mA / cm². 2 The driving voltage, current efficiency, and emission peak under these conditions are shown in Table 1 below.

[0333] [Table 1]

[0334]

[0335] As shown in Table 1 above, it can be seen that the blue organic electroluminescent elements of Examples 1 to 15, which use the compounds of the present invention as electron transport layer materials, exhibit superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent element of Comparative Example 1, which uses the conventional ET-1 as electron transport layer material.

[0336] [Examples 16-30] Fabrication of Blue Organic Electroluminescent Element

[0337] After refining the above-synthesized compounds 1 to 116 to a high purity using commonly known methods, blue organic electroluminescent elements were prepared as follows.

[0338] A glass substrate coated with an indium tin oxide (ITO) film at a thickness of 1500 Å was ultrasonically washed with distilled water. After washing with distilled water, it was ultrasonically washed with solvents such as isopropanol, acetone, and methanol, and then dried. It was then transferred to a UV ozone cleaner (Power sonic 405, Hwashintech), where it was cleaned with UV light for 5 minutes. Finally, the substrate was transferred to a vacuum evaporation machine.

[0339] Organic electroluminescent elements were fabricated by stacking the following compounds on the prepared ITO transparent electrode in the order of HT-1 + 2% HAT-CN (100Å) / HT-1 (1400Å) / HT-2 (50Å) / BH + 2% BD (200Å) / compounds 1~116 (50Å) from Table 1 below / ET-1:LiQ =1:1 (300Å) / LiF (10Å) / Al (1000Å).

[0340] The structures of HT-1, HAT-CN, HT-2, BH, BD, ET-1, ET-2 and LiQ used at this time are as described in Examples 1 to 15.

[0341] [Comparative Example 2] Fabrication of Blue Organic Electroluminescent Element

[0342] The blue organic electroluminescent element of Comparative Example 2 was fabricated by evaporating an electron transport layer at 350 Å without using an electron transport auxiliary layer material, except that the same procedure was followed as in Example 16 above.

[0343] [Comparative Examples 3-11] Fabrication of Blue Organic Electroluminescent Element

[0344] As an electron transport auxiliary layer material, ET-2 to ET-10 were deposited at 50 Å instead of Compound 1. Otherwise, the same procedures as in Example 16 above were followed to fabricate the blue organic electroluminescent elements of Comparative Examples 3 to 11.

[0345] The structures of ET-2 to ET-10 used at this time are as follows.

[0346]

[0347] [Evaluation Example 2]

[0348] The current density of the organic electroluminescent elements manufactured in Examples 16 to 30 and Comparative Examples 2 to 11 was measured to be 10 mA / cm². 2 The driving voltage, emission wavelength, current efficiency, and emission wavelength are shown in Table 2 below.

[0349] [Table 2]

[0350]

[0351] As shown in Table 2 above, it can be seen that the blue organic electroluminescent elements of Examples 16 to 30, which contain the compound of Chemical Formula 1 of the present invention as the electron transport auxiliary layer material, exhibit superior performance in terms of current efficiency and driving voltage compared with the organic electroluminescent elements of Comparative Example 2, which does not contain the electron transport auxiliary layer, and Comparative Examples 3 to 11, which do not contain the compound of Chemical Formula 1 of the present invention as the electron transport auxiliary layer material.

[0352] Specifically, Comparative Examples 8 to 11, which incorporate the structure of the present invention but use compounds with different structures as electron transport auxiliary layer materials, exhibited low characteristics in terms of device efficiency and driving voltage. In particular, for Compound ET-10, used as an electron transport auxiliary layer material in Comparative Example 11, which had overall low device properties, it was confirmed that it failed to possess suitable properties (e.g., LUMO level, T1 level) as an electron transport layer and / or electron transport auxiliary layer material due to the inclusion of a condensation ring derived from a carbazole group containing heteroatoms.

Claims

1. A compound represented by the following chemical formula 1: Chemical Formula 1 In the above chemical formula 1, X1 to X3 may be the same as or different from each other, and each is independently CR2 or N, wherein at least one of X1 to X3 is N. R1 and R2 may be the same as or different from each other, and are independently chosen from hydrogen, deuterium (D), halogen, cyano, nitro, C1~C. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 ring atoms, C6~C 60 aryl, heteroaryl with 5 to 60 ring atoms, C1~C 40 alkoxy groups, C6~C 60 aryloxy group, C3~C 40 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide, C6~C 60 arylamine group, C5~C 60 The R1 is a group consisting of aryl heteroarylamines and heteroarylamines with 5 to 60 ring atoms, or the R1 can be combined with any adjacent group to form a condensed ring that does not contain heteroatoms. Ar1 to Ar5 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium (D), and C1 to C2. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 ring atoms, C6~C 60 aryl, heteroaryl with 5 to 60 ring atoms, C1~C 40 alkoxy groups, C6~C 60 aryloxy group, C3~C 40 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide, C6~C 60 arylamine group, C5~C 60 It is a group composed of aryl heteroarylamines and heteroarylamines with 5 to 60 ring atoms. L is a single key or can be selected freely from C6 to C. 18 The group consists of arylene groups and heteroarylene groups with 5 to 18 ring atoms. o and p are each an independent integer from 0 to 3. The arylene and heteroarylene groups of L, and the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboronyl, arylboronyl, arylphosphinyl, arylphosphine oxide, and arylamine groups of R1~R2 and Ar1~Ar5 can each be independently selected from hydrogen, deuterium (D), halogen, cyano, nitro, C1~C1. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 ring atoms, C6~C 60 aryl, heteroaryl with 5 to 60 ring atoms, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide, C6~C 60 arylamine group, C5~C 60 The substituted group is composed of one or more substituents from the group consisting of aryl heteroarylamines and heteroarylamines with 5 to 60 ring atoms, wherein when there are multiple substituents, they may be the same as or different from each other.

2. The compound according to claim 1, wherein, The rings containing X1 to X3 are selected from the substituent group represented by the following chemical formulas: In the above formula, * refers to the part connected to chemical formula 1 above. R2, Ar4 and Ar5 are each as defined in claim 1.

3. The compound according to claim 1, wherein, The ring containing R1 is selected from the substituent group represented by the following chemical formulas: In the above formula, * refers to the part connected to chemical formula 1 above. Ring A is a monocyclic or polycyclic hydrocarbon cyclic group that does not contain heteroatoms, and multiple rings A may be the same as or different from each other. R1 and p are each as defined in claim 1.

4. The compound according to claim 1, wherein, The ring containing R1 is selected from the substituent group represented by the following chemical formulas: In the above formula, * refers to the part connected to chemical formula 1 above. R1 and p are each as defined in claim 1.

5. The compound according to claim 1, wherein, Ar1 to Ar5 may be the same or different from each other, and each can be independently selected from C6 to C6. 60 It is a group consisting of aryl groups and heteroaryl groups with 5 to 60 ring atoms.

6. The compound according to claim 1, wherein, Ar1 to Ar5 may be the same as or different from each other, and each is independently selected from any of the following structural formulas: In the above formula, * refers to the part connected to chemical formula 1 above. R4 is selected from hydrogen, deuterium (D), and C1~C. 40 Alkyl groups, C6~C 60 It is a group consisting of aryl groups and heteroaryl groups with 5 to 60 ring atoms.

7. The compound according to claim 1, wherein, L is a single bond or is selected from any of the following structural formulas: In the above formula, * refers to the part that is connected to the above chemical formula 1.

8. The compound according to claim 1, wherein, R1 is selected from hydrogen, deuterium (D), and C1~C. 40 Alkyl groups, C6~C 60 It is a group consisting of aryl groups and heteroaryl groups with 5 to 60 ring atoms, or it can combine with any adjacent group to form a condensed ring.

9. The compound according to claim 1, wherein, The compound represented by chemical formula 1 above can be represented by any one of the following chemical formulas 2 to 6: Chemical formula 2 Chemical formula 3 Chemical Formula 4 Chemical formula 5 Chemical Formula 6 Among the above chemical formulas 2 to 6, Ar1~Ar5, L, R1, o and p are each as defined in claim 1.

10. The compound according to claim 1, wherein, The compound represented by the above chemical formula 1 can be represented by any one of the following chemical formulas 7 to 9: Chemical Formula 7 Chemical Formula 8 Chemical formula 9 Of the above chemical formulas 7 to 9, Z1 is O or S. Z2 is N, R 11 Choose freely from hydrogen, deuterium (D), and C1~C 40 Alkyl groups, C6~C 60 It is a group consisting of aryl groups and heteroaryl groups with 5 to 60 ring atoms, or it can combine with any adjacent group to form a condensation ring. m is an integer from 0 to 3. a is an integer from 1 to 3. X1~X3, Ar1~Ar3, L, R1, o and p are each as defined in claim 1.

11. The compound according to claim 1, wherein, The compound represented by the above chemical formula 1 is represented by any one of the following chemical formulas 10 to 13: Chemical Formula 10 Chemical Formula 11 Chemical formula 12 Chemical formula 13 In the above chemical formulas 10 to 13, X1~X3, Ar1~Ar5, L, R1, o and p are each as defined in claim 1.

12. The compound according to claim 1, wherein, The compound represented by the above chemical formula 1 is represented by any one of the following chemical formulas 14 to 23: 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 Among the above chemical formulas 14 to 23, Ring A is a monocyclic or polycyclic hydrocarbon cyclic group that does not contain heteroatoms, and multiple rings A may be the same as or different from each other. X1~X3, Ar1~Ar5, L, R1, o and p are each as defined in claim 1.

13. The compound according to claim 1, wherein, The compound represented by the above chemical formula 1 is represented by any one of the following chemical formulas 24 to 29: Chemical formula 24 Chemical formula 25 Chemical formula 26 Chemical formula 27 Chemical formula 28 Chemical formula 29 In the above chemical formulas 24 to 29, X1~X3, Ar1~Ar5, L, R1, o and p are each as defined in claim 1.

14. The compound according to claim 1, wherein, The compound represented by the above chemical formula 1 is represented by any one of the following chemical formulas 30 to 39: Chemical Formula 30 Chemical Formula 31 Chemical formula 32 Chemical formula 33 Chemical formula 34 Chemical formula 35 Chemical formula 36 Chemical formula 37 Chemical formula 38 Chemical formula 39 Among the above chemical formulas 30 to 39, X1~X3, Ar1~Ar5, L, R1, o and p are each as defined in claim 1.

15. The compound according to claim 1, wherein, The compound represented by the above chemical formula 1 can be represented by any one of the following chemical formulas 1 to 137: 。 16. The compound according to claim 1, wherein, The compound represented by the above chemical formula 1 is a material for a light-emitting layer, an electron transport layer, or an electron transport auxiliary layer.

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

18. The organic electroluminescent element according to claim 17, 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 transport layer, and an electron transport auxiliary layer.

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