Organic light-emitting compound and organic electroluminescent device using same

Abstract

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

Description

Organic luminescent compound and organic electroluminescent device using the same

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

[0002]

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

[0004] Luminescent materials can be categorized into blue, green, and red luminescent materials based on their luminescent color, as well as yellow and orange luminescent materials for better natural color reproduction. Furthermore, host / dopant systems can be used as luminescent materials to enhance color purity and luminescence efficiency through energy transfer.

[0005] Dopant materials can be divided into fluorescent dopants, which utilize organic materials, and phosphorescent dopants, which utilize metal complexes containing heavy atoms such as Ir and Pt. The development of phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescent materials, and therefore, extensive research is being conducted not only on phosphorescent dopants but also on phosphorescent host materials.

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

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

[0008]

[0009] The present invention can be applied to organic electroluminescent devices, and the technical task of the present invention is to provide a novel compound having excellent heat resistance, carrier transport ability, luminescence ability, etc., and thus can be used as an organic layer material of an organic electroluminescent device, specifically, an electron transport layer, an electron transport auxiliary layer, or a luminescent layer.

[0010] In addition, another technical task of the present invention is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan, including the novel compound.

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

[0012]

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

[0014] [Chemical Formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] Z1 to Z3 are the same or different from each other, and are each independently CR6 or N, provided that at least one of Z1 to Z3 is N,

[0018] Ar1 is C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group, C6~C 60 Arylamine group, C5~C 60 Selected from the group consisting of an arylheteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms,

[0019] X is a single bond, O or S,

[0020] R4 and R5 are the same or different and are each independently C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group, C6~C 60 Arylamine group, C5~C 60 Selected from the group consisting of an arylheteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms;

[0021] m and n are integers from 0 to 8, respectively.

[0022] L is a single bond or C6~C 18 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms,

[0023] k is an integer from 0 to 3,

[0024] R1 to R3, R6 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group, C6~C 60Arylamine group, C5~C 60 is selected from the group consisting of an arylheteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, or may be combined with any adjacent group to form a condensed ring;

[0025] The arylene group, heteroarylene group of the above L; the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above R1~R6 and Ar1 are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group, C6~C 60 Arylamine group, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0026] In addition, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the chemical formula 1.

[0027] Here, the organic layer including the compound represented by the chemical formula 1 may be selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, a life-span improvement layer, an electron transport layer, and an electron transport auxiliary layer. In this case, the compound represented by the chemical formula 1 may be included as at least one material among the phosphorescent host material of the light-emitting layer, the electron transport layer, and the electron transport auxiliary layer.

[0028]

[0029] As one embodiment of the present invention, the compound represented by the above chemical formula 1 can be used as an organic layer material of an organic electroluminescent device because it has excellent electron transport ability, luminescence ability, heat resistance, etc.

[0030] In particular, when the compound represented by the 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 life characteristics compared to conventional electron transport materials.

[0031] Accordingly, the organic electroluminescent device including the compound of the above chemical formula 1 can be significantly improved in aspects such as excellent luminescence performance, low driving voltage, long life, and high efficiency, and thus can be effectively applied to full-color display panels, etc.

[0032] The effects according to the present invention are not limited to those exemplified above, and more diverse effects are included in this specification.

[0033]

[0034] Hereinafter, the present invention will be described in detail.

[0035] <New organic compounds>

[0036] The present invention provides a novel compound that has excellent electron transport ability, luminescence ability, and thermal stability, and thus can exhibit low voltage, high luminescence efficiency, and long life characteristics of a device.

[0037] According to the present invention, the compound represented by chemical formula 1 has a basic skeletal structure in which a nitrogen-containing heteroaromatic ring (e.g., azine, Z1 to Z3-containing ring) having an electron withdrawing group (EWG) is centered, and a silane group (e.g., R1 to R3-containing substituent) and a spiro acridine xanthine moiety (e.g., X-containing ring) are directly connected or connected via a separate linker (e.g., L).

[0038] Specifically, the compound of the above chemical formula 1 includes a nitrogen-containing heteroaromatic ring (e.g., an azine moiety) having EWG characteristics in its molecular skeletal structure, and two donating units are arranged on both sides thereof, thereby serving to increase the stability of the EWG group located at the center, thereby improving the stability of the molecule due to the improvement in electron donating ability.

[0039] In addition, by controlling the bonding position of the silane bonded to the EWG moiety (e.g., the azine moiety), steric hindrance of the molecular structure can be generated, which induces delocalization of the LUMO orbital, thereby controlling the LUMO value suitable for the electron transport layer or electron transport auxiliary layer. In addition, the triplet energy increase can be induced through maximized steric hindrance, and the efficiency and lifetime characteristics of the device can be improved through exciton blocking by gathering excitons toward the host side of the emitting layer.

[0040] In addition, when manufacturing a device using the compound of the above chemical formula 1, the spiro acridine xanthine moiety and the silane moiety of each compound generate a charge trap through which electrons can flow as an EDG, thereby helping electron mobility. Accordingly, when the compound of the above chemical formula 1 is applied as a material for an electron transport layer or an electron transport auxiliary layer, it can well accept electrons from the cathode, so that electrons can be smoothly transferred to the light-emitting layer, thereby lowering the operating voltage of the device and inducing high efficiency and long lifespan. As a result, such an organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.

[0041] As described above, when the compound represented by the chemical formula 1 of the present invention is applied as an organic layer material of an organic electroluminescent device, preferably as an emitting layer material (a blue, green, and / or red phosphorescent host material), an electron transport layer / injection layer material, an emitting auxiliary layer material, or a life-span improving layer material, the performance and life-span characteristics of the organic electroluminescent device can be improved. In particular, when the compound of the present invention is used as an electron transport layer or an electron transport auxiliary layer material, a significantly superior performance improvement effect in terms of the efficiency, driving voltage, and life-span characteristics of the device can be expected. As a result, such an organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.

[0042] According to the present invention, the compound represented by chemical formula 1 has a basic skeletal structure in which a nitrogen-containing heteroaromatic ring (e.g., azine, Z1 to Z3-containing ring) having excellent electron transporting ability and EWG characteristics is centered, and two donating units, for example, a silane group (e.g., an R1 to R3-containing substituent) and a spiro acridine xanthine moiety (e.g., an X-containing ring) are directly connected to each other on both sides of the ring or connected via a separate linker (e.g., L).

[0043] The above nitrogen-containing heterocyclic ring (e.g., Z1 to Z3-containing ring) is a monocyclic nitrogen-containing heteroaryl group containing at least one nitrogen atom. In one embodiment of the nitrogen-containing heteroaromatic ring, Z1 to Z3 are the same or different, and are each independently C(R6) or N, provided that at least one of Z1 to Z3 contains N. Preferably, it contains 2 to 3 Ns. By including a heterocyclic ring containing 2 to 3 nitrogens in this way, it exhibits better electron absorption properties, which is advantageous for electron injection and transport.

[0044] Here, R6 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group, C6~C 60 Arylamine group, C5~C 60 It is selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms. In this case, when there are multiple R6s, the multiple R6s may be the same or different from each other. Specifically, R6 is hydrogen, deuterium (D), C1~C 40 Alkyl group of C6~C 60It is preferably selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

[0045] For example, the nitrogen-containing heterocycle (e.g., Z1 to Z3-containing ring) can be further specified as one selected from the structural formula below, but is not limited thereto.

[0046]

[0047] In the above formula,

[0048] * indicates a part connected to the above chemical formula 1,

[0049] R6 and Ar1 are each as defined in chemical formula 1.

[0050] In the above nitrogen-containing heterocycle (e.g., Z1~Z3-containing ring), Ar1 can be substituted with various substituents. Ar1 has a non-hydrogen-based substituent, for example, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group, C6~C 60 Arylamine group, C5~C 60 It can be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms. Specifically, Ar1 is C6~C 60An aryl group of , or a heteroaryl group having 5 to 60 nuclear atoms, more specifically C6~C 40 It is preferable that it is an aryl group.

[0051] For example, Ar1 may be embodied by any one of the following structural formulas, but is not limited thereto.

[0052]

[0053] In the above formula,

[0054] * indicates a part connected to the above chemical formula 1,

[0055] R 11 Silver hydrogen, deuterium (D), C1~C 40 Alkyl group of C6~C 60 , and a heteroaryl group having 5 to 60 nuclear atoms. In addition, although not shown in the structural formula described above, at least one substituent known in the art (e.g., the same as the definition of R6) may be substituted.

[0056] In the compound represented by Chemical Formula 1 according to the present invention, a spiro acridine xanthine moiety (e.g., an X-containing ring) is included as one of two donating units connected to both sides of a nitrogen-containing heteroaromatic ring (e.g., an azine, Z1-Z3-containing ring). In one embodiment of such a spiro acridine xanthine moiety (e.g., an X-containing ring), X is a single bond, O, or S.

[0057] For example, the spiro-acridine xanthine moiety (e.g., X-containing ring) may be embodied by any one of the following structural formulae, but is not limited thereto.

[0058]

[0059] In the above formula,

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

[0061] The above spiro acridine xanthine moiety (e.g., X-containing ring) may be introduced with R4 and R5. These R4 and R5 are the same or different from each other, and are each independently hydrogen, deuterium (D), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group, C6~C 60 Arylamine group, C5~C 60 It can be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms. When R4 and / or R5 are each plural, the plural R4 and / or R5 may be the same or different from each other. Specifically, R4 and / or R5 are the same or different from each other, and each independently represent hydrogen, deuterium (D), C1~C 40 Alkyl group of C6~C 60 It is preferably selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

[0062] m and n are each an integer from 0 to 8, specifically an integer from 0 to 4. Here, when m is 0, R4 is hydrogen, and when m is 1 to 8, R4 may have the aforementioned substituents except hydrogen. The same may be applied to n and R5. In this case, when R4 and / or R5 have the aforementioned substituents except hydrogen, each may have 1 or fewer substituents in consideration of the total molecular weight of the compound.

[0063] As a more specific example, the spiro acridine xanthine moiety (e.g., X-containing ring) can be embodied by any one selected from the following structural formulas.

[0064]

[0065]

[0066] In the above formula,

[0067] * indicates a part connected to the above chemical formula 1,

[0068] R4 to R5, m and n are each as defined in Article 1.

[0069] In the compound represented by chemical formula 1 according to the present invention, a silane moiety (e.g., R1 to R3 moiety) is included as the other of two donating units connected to both sides of a nitrogen-containing heteroaromatic ring (e.g., azine, Z1 to Z3-containing ring).

[0070] In these silane moieties, R1 to R3 are each substituted as a substituent. The R1 to R3 are the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group, C6~C 60 Arylamine group, C5~C 60 is selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, or may be combined with any adjacent group to form a condensed ring. Specifically, R1 to R3 are the same or different from each other, and are each independently C1 to C 40 Alkyl group of C6~C 60 If it is an aryl group of R1 to R3, or at least two of the above R1 to R3 are aryl groups, it is preferable to form a condensed ring by combining with another adjacent aryl group, and more specifically, C6 to C 40 is an aryl group.

[0071] For example, the silane moiety containing R1 to R3 may be embodied by any one of the following structural formulas, but is not limited thereto.

[0072]

[0073] In the above chemical formula,

[0074] * indicates a part connected to chemical formula 1,

[0075] p is an integer from 1 to 3.

[0076] Ring A may be a hydrocarbon ring containing one or more conventional hydrocarbon atoms or heteroatoms known in the art, and may be in the form of condensation, fusion, bridged or spirocyclic bonding with another adjacent ring (e.g., core structure). For example, Ring A may be selected from the group consisting of 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. Specifically, Ring A is C6~C 18 It is preferable that it is an aromatic ring or a heteroaromatic ring having 5 to 18 nuclear atoms.

[0077] In the compound represented by chemical formula 1 according to the present invention, the nitrogen-containing heteroaromatic ring (e.g., azine, Z1 to Z3-containing ring) and the silane moiety (e.g., R1 to R3 moiety) may be directly bonded or bonded via a separate linker (L). When a separate linker (L) exists between the nitrogen-containing heteroaromatic ring and the silane moiety in this way, the HOMO region can be expanded, thereby providing a benefit to the HOMO-LUMO distribution, and charge transfer efficiency can be increased through appropriate HOMO-LUMO overlap. In addition, by controlling the bonding position between the silane moiety and the linker, steric hindrance of the molecular structure can be generated, thereby inducing delocalization of the LUMO orbital, thereby controlling the LUMO value suitable for the electron transport layer or the electron transport auxiliary layer.

[0078] Such linker (L) may be a common divalent group linker known in the art. Specifically, L may be a single bond or a C6~C 18 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms.

[0079] k is an integer from 0 to 3. Here, when k is 0, L is a single bond (direct bond), and when k is 1 to 3, it may have at least one selected from the group consisting of the above-mentioned arylene group and heteroarylene group. In this case, when there are multiple Ls, the multiple Ls may be the same or different from each other.

[0080] Specific examples of the above arylene linker include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyranthrenylene group, a carbazolylene group, a thiophenylene group, an indoylene group, a purinylene group, a quinolinylene group, a pyrrolylene group, an imidazolylene group, an oxazolilene group, a thiazolilene group, a pyridinylene group, a pyrimidinylene group, etc. More specifically, a phenylene group or a biphenylene group is preferable. In addition, specific examples of heteroarylene linkers include a pyrrole moiety, a furan moiety, a thiophene moiety, a pyridine moiety, a pyrimidine moiety, a pyrazine moiety, a triazine moiety, a dibenzofuran moiety, a dibenzothiophene moiety, and / or a dibenzoselenophenone moiety.

[0081] For example, L may be a single bond or may be embodied as one selected from the following structural formulas, but is not limited thereto.

[0082]

[0083] In the above formula,

[0084] * indicates a portion connected to the above chemical formula 1. In addition, although not indicated in the above structural formula, at least one substituent known in the art (e.g., the same as the R6 definition portion) may be substituted.

[0085] In the above-mentioned chemical formula 1, the arylene group, heteroarylene group of L; the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of R1 to R6 and Ar1 are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group, C6~C 60 Arylamine group, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0086] In one embodiment of the present invention, the compound represented by the above chemical formula 1 may be further specified as one of the following chemical formulas 2 to 8 depending on the type of nitrogen-containing heteroaromatic ring (e.g., Z1 to Z3-containing ring). However, the present invention is not limited thereto.

[0087] [Chemical Formula 2]

[0088]

[0089] [Chemical Formula 3]

[0090]

[0091] [Chemical Formula 4]

[0092]

[0093] [Chemical Formula 5]

[0094]

[0095] [Chemical Formula 6]

[0096]

[0097] [Chemical Formula 7]

[0098]

[0099] [Chemical Formula 8]

[0100]

[0101] In the above chemical formulas 2 to 8,

[0102] X, Ar1, L, R1~R5, k, m and n are each as defined in chemical formula 1.

[0103] In another embodiment of the present invention, the compound represented by the above chemical formula 1 may be further specified as one of the following chemical formulas 9 to 11 depending on the type of spiro acridine xanthine moiety (e.g., X-containing ring). However, the present invention is not limited thereto.

[0104] [Chemical Formula 9]

[0105]

[0106] [Chemical Formula 10]

[0107]

[0108] [Chemical Formula 11]

[0109]

[0110] In the above chemical formulas 9 to 11,

[0111] Z1~Z3, Ar1, L, R1~R5, k, m and n are each as defined in chemical formula 1.

[0112] In another embodiment of the present invention, the compound represented by the above chemical formula 1 can be further specified as one of the following chemical formulas 12 to 17, depending on the introduction form of the R4 to R5 substituents introduced into the spiro acridine xanthine moiety (e.g., X-containing ring). However, the present invention is not limited thereto.

[0113] [Chemical Formula 12]

[0114]

[0115] [Chemical Formula 13]

[0116]

[0117] [Chemical Formula 14]

[0118]

[0119] [Chemical Formula 15]

[0120]

[0121] [Chemical Formula 16]

[0122]

[0123] [Chemical Formula 17]

[0124]

[0125] In the above chemical formulas 12 to 17,

[0126] Z1~Z3, X, Ar1, L, R1~R5, k, m and n are each as defined in chemical formula 1.

[0127] In another embodiment of the present invention, the compound represented by the above chemical formula 1 can be further specified as one of the following chemical formulas 18 to 23, depending on the bonding position of the R4 to R5 substituents introduced to the spiro acridine xanthine moiety (e.g., X-containing ring). However, the present invention is not limited thereto.

[0128] [Chemical Formula 18]

[0129]

[0130] [Chemical Formula 19]

[0131]

[0132] [Chemical Formula 20]

[0133]

[0134] [Chemical Formula 21]

[0135]

[0136] [Chemical Formula 22]

[0137]

[0138] [Chemical Formula 23]

[0139]

[0140] In the above chemical formulas 18 to 23,

[0141] Z1~Z3, X, Ar1, L, R1~R5, k, m and n are each as defined in chemical formula 1.

[0142] In another embodiment of the present invention, the compound represented by the above chemical formula 1 can be further specified as one of the following chemical formulas 24 to 26 depending on the bonding position between the silane group (e.g., R1 to R3-containing moiety) and the nitrogen-containing heteroaromatic ring (e.g., Z1 to Z3-containing ring). However, the present invention is not limited thereto.

[0143] [Chemical Formula 24]

[0144]

[0145] [Chemical Formula 25]

[0146]

[0147] [Chemical Formula 26]

[0148]

[0149] In the above chemical formulas 24 to 26,

[0150] Z1~Z3, X, Ar1, L, R1~R5, k, m and n are each as defined in chemical formula 1.

[0151] In another embodiment of the present invention, the compound represented by the above chemical formula 1 may be further specified as the following chemical formula 27 or chemical formula 28 depending on the type of linker (e.g., L). However, the present invention is not limited thereto.

[0152] [Chemical Formula 27]

[0153]

[0154] [Chemical Formula 28]

[0155]

[0156] In the above chemical formulas 27 to 28,

[0157] Ring B is a condensed polycyclic aromatic ring having 8 to 18 carbon atoms,

[0158] Z1~Z3, X, Ar1, R1~R5, k, m and n are each as defined in chemical formula 1.

[0159] In another embodiment of the present invention, the compound represented by the above chemical formula 1 may be further specified as one of the following chemical formulas 29 to 40, depending on the type of linker and the bonding position therebetween. However, the present invention is not limited thereto.

[0160] [Chemical Formula 29]

[0161]

[0162] [Chemical Formula 30]

[0163]

[0164] [Chemical Formula 31]

[0165]

[0166] [Chemical Formula 32]

[0167]

[0168] [Chemical Formula 33]

[0169]

[0170] [Chemical Formula 34]

[0171]

[0172] [Chemical Formula 35]

[0173]

[0174] [Chemical Formula 36]

[0175]

[0176] [Chemical Formula 37]

[0177]

[0178] [Chemical Formula 38]

[0179]

[0180] [Chemical Formula 39]

[0181]

[0182] [Chemical Formula 40]

[0183]

[0184] In the above chemical formulas 29 to 40,

[0185] Z1~Z3, X, Ar1, R1~R5, m and n are each as defined in chemical formula 1.

[0186] The compound represented by chemical formula 1 according to the present invention described above can be further specified as a compound represented by any one of compounds 1 to 160 exemplified below. However, the compound represented by chemical formula 1 of the present invention is not limited to those exemplified below.

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195] In the present invention, the "number of nuclear atoms" refers to the number of ring atoms constituting a ring structure, and the nuclear atoms may be carbon or a heteroatom selected from the group consisting of N, O, S, and Se. For example, the number of nuclear atoms of pyridine refers to 6, including 5 C and 1 N constituting the pyridine ring.

[0196] In the present invention, "alkyl" means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0197] In the present invention, "alkenyl" means a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

[0198] In the present invention, "alkynyl" means a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0199] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms, which is a single ring or a combination of two or more rings. Furthermore, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0200] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, at least one carbon atom in the ring, preferably 1 to 3 carbon atom, is substituted with a heteroatom such as N, O, S, or Se. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included, and a form condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl.

[0201] In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

[0202] In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0203] In the present invention, “arylamine” means an amine substituted with an aryl having 6 to 40 carbon atoms.

[0204] 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, and adamantine.

[0205] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon atom in the ring, preferably 1 to 3 carbon atom(s), is substituted with a heteroatom such as N, O, S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

[0206] In the present invention, “alkylsilyl” means silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” means silyl substituted with aryl having 5 to 40 carbon atoms.

[0207] In the present invention, “fused ring” means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

[0208] Electron transport layer material

[0209] The present invention provides an electron transport layer comprising a compound represented by the above chemical formula 1.

[0210] The above electron transport layer (ETL) plays a role in moving electrons injected from the cathode to an adjacent layer, specifically, the light-emitting layer.

[0211] The compound represented by the above chemical formula 1 may be used alone as an electron transport layer (ETL) material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.

[0212] The electron transport layer material that can be mixed with the compound of the above chemical formula 1 includes an electron transport material commonly known in the art. Non-limiting examples of electron transport materials that can be used 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. These may be used alone or in combination of two or more.

[0213] In the present invention, when the compound of the above chemical formula 1 and the electron transport layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately controlled within a range known in the art.

[0214] <Electron transport auxiliary layer material>

[0215] In addition, the present invention provides an electron transport auxiliary layer comprising a compound represented by the above chemical formula 1.

[0216] The electron transport auxiliary layer is positioned between the light-emitting layer and the electron transport layer, and serves to prevent excitons or holes generated in the light-emitting layer from diffusing into the electron transport layer.

[0217] The compound represented by the above chemical formula 1 may be used alone as an electron transport auxiliary layer material, or may be mixed with an electron transport auxiliary layer material known in the art. It is preferably used alone.

[0218] The electron transport auxiliary layer material that can be mixed with the compound of the above chemical formula 1 includes an electron transport material commonly known in the art. For example, the electron transport material mixed with the electron transport auxiliary layer material may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative (e.g., BCP), a nitrogen-containing heterocyclic derivative, and the like.

[0219] In the present invention, when the compound of the above chemical formula 1 and the electron transport auxiliary layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately controlled within a range known in the art.

[0220] Organic electroluminescent devices

[0221] Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising a compound represented by the chemical formula 1 according to the present invention.

[0222] Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the chemical formula 1. At this time, the compound may be used alone or in a mixture of two or more.

[0223] The organic layer of one or more layers may be at least one of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a life-span improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of the organic layers includes a compound represented by the chemical formula 1. Specifically, the organic layer including the compound of the chemical formula 1 may be a light-emitting layer, a light-emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and / or a life-span improvement layer, and more specifically, it is preferably an electron transport layer or an electron transport auxiliary layer.

[0224] The light-emitting layer of the organic electroluminescent device according to the present invention includes a host material and a dopant material, and may include the compound of the above chemical formula 1 as the host material. In addition, the light-emitting layer of the present invention may include a known compound in the art other than the compound of the above chemical formula 1 as the host.

[0225] When the compound represented by the above chemical formula 1 is included as a light-emitting layer material of an organic electroluminescent device, preferably as a blue, green, or red phosphorescent host material, the bonding force between holes and electrons in the light-emitting layer increases, thereby improving the efficiency (luminescent efficiency and power efficiency), lifespan, brightness, and driving voltage of the organic electroluminescent device. Specifically, the compound represented by the above chemical formula 1 is preferably included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, the compound represented by the chemical formula 1 of the present invention is preferably a green phosphorescent exciplex N-type host material of a light-emitting layer having high efficiency.

[0226] The structure of the organic electroluminescent device of the present invention is not particularly limited, but may have 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 laminated. At this time, at least one of the hole injection layer, the hole transport layer, the light-emitting auxiliary layer, the light-emitting layer, the electron transport layer, and the electron injection layer may include a compound represented by the chemical formula 1, and preferably, the light-emitting layer, and more preferably, the phosphorescent host, may include a compound represented by the chemical formula 1. Meanwhile, an electron injection layer may be additionally laminated on the electron transport layer.

[0227] The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0228] The organic electroluminescent device of the present invention can be manufactured by forming an organic layer and an electrode using materials and methods known in the art, except that at least one of the organic layers described above includes a compound represented by the chemical formula 1.

[0229] The above organic layer can be formed by vacuum deposition or solution coating. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

[0230] The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, and for example, a silicon wafer, quartz, glass plate, metal plate, plastic film and sheet, etc. can be used.

[0231] In addition, the cathode material may be any cathode material known in the art without limitation. Examples thereof include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black.

[0232] In addition, the cathode material may be any cathode material known in the art without limitation. Examples thereof include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayered materials such as LiF / Al or LiO2 / Al.

[0233] In addition, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and conventional materials known in the art can be used without limitation.

[0234] Hereinafter, the present invention will be described in detail through examples. However, the following examples are only illustrative of the present invention, and the present invention is not limited to the following examples.

[0235] [Examples 1-7]

[0236] [Preparation Example 1] Synthesis of SA-1

[0237]

[0238] 2,4-dichloro-6-phenyl-1,3,5-triazine (30.0 g, 132.7 mmol), 10H-spiro[acridine-9,9'-fluorene] (35.2 g, 106.2 mmol), Pd(OAc)2 (1.5 g, 6.6 mmol), (t-Bu)3P (in 50% toluene) (5.4 g, 26.6 mmol) were added to 300 ml of toluene and heated under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain SA-1 (28.4 g, yield 41%).

[0239] 1H-NMR: δ 8.36(d, 2H), 7.90(d, 2H), 7.55(d, 2H), 7.50(m, 3H), 7.35~7.15(m, 10H), 6.95(t, 2H)

[0240] Mass: [(M+H)+] : 522

[0241] [Preparation Example 2] Synthesis of SA-2

[0242]

[0243] Compound SA-2 (29.1 g, yield 42%) was obtained in the same manner as in Preparation Example 1, except that 2-chloro-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine was used instead of compound 2,4-dichloro-6-phenyl-1,3,5-triazine.

[0244] 1H-NMR: δ 8.36(d, 2H), 8.16(d, 1H), 7.97(s, 1H), 7.90(d, 2H), 7.50-7.15(m, 17H), 6.95(t, 2H)

[0245] Mass: [(M+H)+] : 598

[0246] [Preparation Example 3] Synthesis of SA-3

[0247]

[0248] Compound SA-3 (28.8 g, yield 41%) was obtained in the same manner as in Preparation Example 1, except that 2-([1,1'-biphenyl]-3-yl)-4,6-dichloro-1,3,5-triazine was used instead of compound 10H-spiro[acridine-9,9'-fluorene].

[0249] 1H-NMR: δ 8.38 (d, 1H), 7.90 (d, 2H), 7.75-7.73 (m, 3H), 7.49-7.17 (m, 16H), 6.95 (t, 2H)

[0250] Mass: [(M+H)+] : 598

[0251] [Preparation Example 4] Synthesis of SA-4

[0252]

[0253] Compound SA-4 (27.6 g, yield 39%) was obtained in the same manner as in Preparation Example 1, except that 10H-spiro[acridine-9,9'-xanthene] was used instead of compound 10H-spiro[acridine-9,9'-fluorene].

[0254] 1H-NMR: δ 8.36 (d, 2H), 7.50 (t, 3H), 7.31 (t, 2H), 7.19-7.13 (m, 10H), 7.01-6.95 (m, 4H)

[0255] Mass: [(M+H)+] : 537

[0256] [Preparation Example 5] Synthesis of SA-5

[0257]

[0258] Compound SA-5 (27.9 g, yield 40%) was obtained in the same manner as in Preparation Example 1, except that 10H-spiro[acridine-9,9'-thioxanthene] was used instead of compound 10H-spiro[acridine-9,9'-fluorene].

[0259] 1H-NMR: δ 8.36(d, 2H), 7.69(d, 2H), 7.50(t, 3H), 7.33(t, 2H), 7.19-7.16(m, 6H), 7.14-6.95(m, 6H)

[0260] Mass: [(M+H)+] : 554

[0261] [Preparation Example 6] Synthesis of SA-6

[0262]

[0263] Compound SA-6 (28.8 g, yield 42%) was obtained in the same manner as in Preparation Example 1, except that 4,6-dichloro-2-phenylpyrimidine was used instead of 2,4-dichloro-6-phenyl-1,3,5-triazine.

[0264] 1H-NMR: δ 8.40(d, 2H), 7.90(d, 2H), 7.50(t, 3H), 7.38-7.19(m, 10H), 6.95(t, 2H), 6.36(s, 1H)

[0265] Mass: [(M+H)+] : 521

[0266] [Preparation Example 7] Synthesis of SA-7

[0267]

[0268] Compound SA-7 (29.6 g, yield 42%) was obtained in the same manner as in Preparation Example 1, except that 4,6-dichloro-2-(naphthalen-1-yl)pyrimidine was used instead of compound 2,4-dichloro-6-phenyl-1,3,5-triazine.

[0269] 1H-NMR: δ 8.97(d, 1H), 8.25(d, 1H), 8.15-8.10(m, 2H), 8.00(t, 1H), 7.90(d, 2H), 7.59-7.52(m, 4H), 7.38-7.15(m, 10H), 6.95(t, 2H), 6.36(s, 1H)

[0270] Mass: [(M+H)+] : 571

[0271] [Synthesis Examples 1-15]

[0272] [Synthesis Example 1] Synthesis of Compound 1

[0273]

[0274] SA-1 (5.0 g, 9.6 mmol), (3-(triphenylsilyl)phenyl)boronic acid (3.6 g, 9.6 mmol), Pd(PPh3)4 (0.3 g, 0.3 mmol), and K2CO3 (2.7 g, 19.2 mmol) were added to a mixed solvent of 80 ml of dioxane and 20 ml of H2O and reacted while heating and stirring under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 1 (4.3 g, yield 55%).

[0275] Mass: [(M+H)+] : 822

[0276] [Synthesis Example 2] Synthesis of Compound 2

[0277]

[0278] Compound 2 (4.1 g, yield 54%) was obtained in the same manner as in Synthetic Example 1, except that (4-(triphenylsilyl)phenyl)boronic acid was used instead of (3-(triphenylsilyl)phenyl)boronic acid.

[0279] Mass: [(M+H)+] : 822

[0280] [Synthesis Example 3] Synthesis of Compound 5

[0281]

[0282] SA-2 (5.0 g, 8.4 mmol), (3-(triphenylsilyl)phenyl)boronic acid (3.2 g, 8.4 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.2 g, 0.5 mmol), and Cs2CO3 (5.5 g, 16.8 mmol) were added to 80 ml of dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 5 (4.4 g, yield 58%).

[0283] Mass: [(M+H)+] : 898

[0284] [Synthesis Example 4] Synthesis of Compound 6

[0285]

[0286] Compound 6 (4.3 g, yield 56%) was obtained in the same manner as in Synthesis Example 3, except that (4-(triphenylsilyl)phenyl)boronic acid was used instead of (3-(triphenylsilyl)phenyl)boronic acid.

[0287] Mass: [(M+H)+] : 898

[0288]

[0289] [Synthesis Example 5] Synthesis of Compound 10

[0290]

[0291] Compound 10 (4.3 g, yield 54%) was obtained in the same manner as in Synthetic Example 1, except that SA-3 was used instead of compound SA-1.

[0292] Mass: [(M+H)+] : 898

[0293] [Synthesis Example 6] Synthesis of Compound 20

[0294]

[0295] Compound 20 (4.3 g, yield 53%) was obtained in the same manner as in Synthesis Example 1, except that (3-([1,1'-biphenyl]-3-yldiphenylsilyl)phenyl)boronic acid was used instead of (3-(triphenylsilyl)phenyl)boronic acid.

[0296] Mass: [(M+H)+] : 898

[0297] [Synthesis Example 7] Synthesis of Compound 41

[0298]

[0299] Compound 41 (4.6 g, yield 55%) was obtained in the same manner as in Synthetic Example 1, except that SA-4 was used instead of compound SA-1.

[0300] Mass: [(M+H)+] : 838

[0301] [Synthesis Example 8] Synthesis of Compound 42

[0302]

[0303] Compound 42 (4.3 g, yield 53%) was obtained in the same manner as in Synthetic Example 7, except that (4-(triphenylsilyl)phenyl)boronic acid was used instead of (3-(triphenylsilyl)phenyl)boronic acid.

[0304] Mass: [(M+H)+] : 838

[0305] [Synthesis Example 9] Synthesis of Compound 61

[0306]

[0307] Compound 61 (3.8 g, yield 49%) was obtained in the same manner as in Synthetic Example 1, except that SA-5 was used instead of compound SA-1.

[0308] Mass: [(M+H)+] : 854

[0309] [Synthesis Example 10] Synthesis of Compound 80

[0310]

[0311] Compound 80 (4.3 g, yield 51%) was obtained in the same manner as in Synthetic Example 9, except that (4-([1,1'-biphenyl]-4-yldiphenylsilyl)phenyl)boronic acid was used instead of (3-(triphenylsilyl)phenyl)boronic acid.

[0312] Mass: [(M+H)+] : 930

[0313] [Synthesis Example 11] Synthesis of Compound 81

[0314]

[0315] Compound 81 (4.0 g, yield 53%) was obtained in the same manner as in Synthetic Example 1, except that SA-6 was used instead of compound SA-1.

[0316] Mass: [(M+H)+] : 821

[0317] [Synthesis Example 12] Synthesis of Compound 82

[0318]

[0319] Compound 82 (3.9 g, yield 50%) was obtained in the same manner as in Synthetic Example 11, except that (4-(triphenylsilyl)phenyl)boronic acid was used instead of (3-(triphenylsilyl)phenyl)boronic acid.

[0320] Mass: [(M+H)+] : 821

[0321] [Synthesis Example 13] Synthesis of Compound 92

[0322]

[0323] Compound 92 (3.5 g, yield 46%) was obtained in the same manner as in Synthetic Example 1, except that SA-7 was used instead of compound SA-1.

[0324] Mass: [(M+H)+] : 871

[0325] [Synthesis Example 14] Synthesis of Compound 97

[0326]

[0327] Compound 97 (4.1 g, yield 51%) was obtained in the same manner as in Synthetic Example 13, except that (4-(triphenylsilyl)phenyl)boronic acid was used instead of (3-(triphenylsilyl)phenyl)boronic acid.

[0328] Mass: [(M+H)+] : 871

[0329] [Synthesis Example 15] Synthesis of Compound 102

[0330]

[0331] Compound 102 (4.6 g, yield 56%) was obtained in the same manner as in Synthetic Example 11, except that (3-(naphthalen-1-yldiphenylsilyl)phenyl)boronic acid was used instead of (3-(triphenylsilyl)phenyl)boronic acid.

[0332] Mass: [(M+H)+] : 871

[0333]

[0334] [Examples 1 to 15] Fabrication of blue organic electroluminescent devices

[0335] After the compound synthesized in the above synthesis example was purified by high purity sublimation using a commonly known method, a blue organic electroluminescent device was manufactured according to the process below.

[0336] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, 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, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.

[0337] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking HI + 2% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / BH + 2% BD (20 nm) / each compound in Table 1 (electron transport layer material) + Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm) in that order.

[0338]

[0339] [Comparative Examples 1 to 7] Manufacturing of blue organic electroluminescent devices

[0340] Blue organic electroluminescent devices of Comparative Examples 1 to 7 were manufactured in the same manner as in Example 1, except that Alq3 and AC-1 to AC-6 were used instead of Compound 1 as electron transport layer materials.

[0341] The structures of compounds HI, HAT-CN6, EB, BH, BD, Liq, Alq3, ET, and AC-1 to AC-6 used in the above examples and comparative examples are as follows, respectively.

[0342]

[0343]

[0344]

[0345] [Evaluation Example 1]

[0346] For the organic electroluminescent devices manufactured in Examples 1 to 15 and Comparative Examples 1 to 7, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm2 were measured, and the results are shown in Table 1 below.

[0347] Sample Electron Transport Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 1 Compound 13.34548.1 Example 2 Compound 23.44548.0 Example 3 Compound 53.34558.1 Example 4 Compound 63.54547.9 Example 5 Compound 103.44558.0 Example 6 Compound 203.34547.9 Example 7 Compound 413.34558.0 Example 8 Compound 423.44548.1 Example 9 Compound 613.54548.0 Example 10 Compound 803.34548.0 Example 11 Compound 813.34558.1 Example 12 Compound 823.24547.9 Example 13 Compound 923.34558.1 Example 14 Compound 973.44537.9 Example 15 Compound 1023.24548.1 Comparative Example 1 Alq 34.64575.6 Comparative Example 2 AC-14.14587.0 Comparative Example 3 AC-24.04576.9 Comparative Example 4 AC-34.34566.9 Comparative Example 5 AC-44.34566.8 Comparative Example 6 AC-54.44566.8 Comparative Example 7 AC-64.34566.6

[0348] As shown in Table 1 above, it was found that the blue organic electroluminescent devices of Examples 1 to 15 using the compound according to the present invention as an electron transport layer material exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to Comparative Example 1 using conventional Alq3 as an electron transport layer material; and Comparative Examples 2 to 7 using a compound including an azine group and a xanthine moiety but not a silane group as an electron transport layer material.

[0349]

[0350] [Examples 16 to 30] Fabrication of blue organic electroluminescent devices

[0351] After the compound synthesized in the above synthesis example was purified by high purity sublimation using a commonly known method, a blue organic electroluminescent device was manufactured according to the process below.

[0352] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, 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, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.

[0353] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking HI + 2% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / BH + 2% BD (20 nm) / each compound in Table 1 (electron transport auxiliary layer material) (5 nm) / ET + Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm) in that order.

[0354]

[0355] [Comparative Example 8]

[0356] A blue organic electroluminescent device of Comparative Example 8 was manufactured in the same manner as in Example 16, except that no electron transport auxiliary layer material was used.

[0357]

[0358] [Comparative Examples 9 to 14] Manufacturing of blue organic electroluminescent devices

[0359] Blue organic electroluminescent devices of Comparative Examples 9 to 14 were manufactured in the same manner as in Example 16, except that AC-1 to AC-6 were used instead of Compound 1 as the electron transport auxiliary layer material.

[0360] The structures of the compounds HI, HAT-CN6, EB, BH, BD, Liq, Alq3, ET, and AC-1 to AC-6 used at this time are as specified in Examples 1 to 15 described above.

[0361]

[0362] [Evaluation Example 2]

[0363] For the organic electroluminescent devices manufactured in Examples 16 to 30 and Comparative Examples 9 to 14, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm2 were measured, and the results are shown in Table 2 below.

[0364] Sample Electron Transport Auxiliary Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 16 Compound 13.24558.2 Example 17 Compound 23.14558.3 ​​Example 18 Compound 53.24548.2 Example 19 Compound 63.14558.3 ​​Example 20 Compound 103.34558.3 ​​Example 21 Compound 203.24548.2 Example 22 Compound 413.24558.3 ​​Example 23 Compound 423.34558.1 Example 24 Compound 613.34548.2 Example 25 Compound 803.24558.3 ​​Example 26 Compound 813.24558.2 Example 27 Compound 823.24548.2 Example 28 Compound 923.14548.4 Example 29 Compound 973.24548.3 Example 30 Compound 1023.14548.1 Comparative Example 8-4.64566.3 Comparative Example 9 AC-13.94577.1 Comparative Example 10 AC-24.04566.8 Comparative Example 11 AC-34.14566.9 Comparative Example 12 AC-44.24566.6 Comparative Example 13 AC-54.34566.5 Comparative Example 14 AC-64.44566.5

[0365]

[0366] As shown in Table 2 above, it was found that the blue organic electroluminescent devices of Examples 16 to 30 using the compound according to the present invention as an electron transport auxiliary layer material exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent devices of Comparative Example 8, which did not include an electron transport auxiliary layer; and Comparative Examples 9 to 14, which used a compound including an azine group and a xanthine moiety but not a silane group as an electron transport auxiliary layer material.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, Z1 to Z3 are the same or different from each other, and are each independently CR6 or N, provided that at least one of Z1 to Z3 is N, Ar1 is C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group, C6~C 60 Arylamine group, C5~C 60 Selected from the group consisting of an arylheteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, X is a single bond, O or S, R4 and R5 are the same or different and are each independently C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group, C6~C 60 Arylamine group, C5~C 60 Selected from the group consisting of an arylheteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms; m and n are integers from 0 to 8, respectively. L is a single bond or C6~C 18 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms, k is an integer from 0 to 3, R1 to R3, R6 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group, C6~C 60 Arylamine group, C5~C 60 is selected from the group consisting of an arylheteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, or may be combined with any adjacent group to form a condensed ring; The arylene group, heteroarylene group of the above L; the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above R1~R6 and Ar1 are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group, C6~C 60 Arylamine group, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, and in this case, when there are multiple substituents, they may be the same or different from each other.

2. In paragraph 1, The above Z1 to Z3 containing ring is a compound selected from the group of substituents represented by the following chemical formula: In the above formula, * indicates a part connected to the above chemical formula 1, R6 and Ar1 are each as defined in paragraph 1.

3. In paragraph 1, Ar1 is C6~C 60 A compound selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

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

5. In paragraph 1, The above X-containing ring is a compound selected from the following structural formulas: In the above formula, * indicates a part connected to the above chemical formula 1, R4 to R5, m and n are each as defined in Article 1.

6. In paragraph 1, R1 to R3 are the same or different and are each independently C1 to C 40 Alkyl group or C6~C 60 A compound wherein the aryl group is a group of R1 to R3, or, when at least two of the above R1 to R3 are aryl groups, combines with another adjacent aryl group to form a condensed ring.

7. In paragraph 1, The above R1 to R3-containing silane moiety is a compound selected from the following structural formulas: In the above chemical formula, * indicates a part connected to chemical formula 1, Ring A is a monocyclic or polycyclic hydrocarbon ring group, p is an integer from 1 to 3.

8. In paragraph 1, L is a single bond or a compound selected from the following structural formulas: In the above formula, * indicates a part connected to the above chemical formula 1.

9. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 2 to 8: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] In the above chemical formulas 2 to 8, X, Ar1, L, R1~R5, k, m and n are each as defined in Article 1.

10. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 9 to 11: [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] In the above chemical formulas 9 to 11, Z1~Z3, Ar1, L, R1~R5, k, m and n are each as defined in Article 1.

11. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 12 to 17: [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] In the above chemical formulas 12 to 17, Z1~Z3, X, Ar1, L, R1~R5, k, m and n are each as defined in Article 1.

12. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 18 to 23: [Chemical Formula 18] [Chemical Formula 19] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] In the above chemical formulas 18 to 23, Z1~Z3, X, Ar1, L, R1~R5, k, m and n are each as defined in Article 1.

13. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 24 to 26: [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 26] In the above chemical formulas 24 to 26, Z1~Z3, X, Ar1, L, R1~R5, k, m and n are each as defined in Article 1.

14. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by the following chemical formula 27 or chemical formula 28: [Chemical Formula 27] [Chemical Formula 28] In the above chemical formulas 27 to 28, Ring B is a condensed polycyclic aromatic ring having 8 to 18 carbon atoms, Z1~Z3, X, Ar1, R1~R5, k, m and n are each as defined in Article 1.

15. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 29 to 40: [Chemical Formula 29] [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] [Chemical Formula 40] In the above chemical formulas 29 to 40, Z1~Z3, X, Ar1, R1~R5, m and n are each as defined in Article 1.

16. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 1 to 160.

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

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

19. In paragraph 18, An organic electroluminescent device, wherein the organic layer including the compound is selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a life-span improvement layer, an electron transport layer, and an electron transport auxiliary layer.

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