Organic compound and organic electroluminescence device using the same

Abstract

The present invention relates to a novel compound having excellent carrier transport ability, light emission ability, and thermal stability, and an organic electroluminescence device in which characteristics such as luminous efficiency, driving voltage, and lifespan are improved by including this compound in one or more organic layers.

Description

Technical Field

[0001] The present invention relates to a novel organic compound and an organic electroluminescence device using the same, and more particularly, to a compound having excellent electron transporting ability and an organic electroluminescence device having improved characteristics such as luminous efficiency, driving voltage, and lifetime by including the compound in one or more organic layers.

Background Art

[0002] Since the discovery of organic thin film luminescence by Bernanose in the 1950s, research on organic electroluminescent devices has led to blue electroluminescence using anthracene single crystals in 1965. In 1987, Tang presented an organic electroluminescent device having a laminated structure composed of a hole layer and a light-emitting layer. Thereafter, in order to obtain an organic electroluminescent device having high efficiency and long life, it has been developed to contain respective characteristic organic layers in the device, leading to the development of special substances for realizing this.

[0003] In an organic electroluminescent device, when a voltage is applied between both electrodes, holes are injected from the positive electrode and electrons are injected into the organic layer from the negative electrode. The injected holes and electrons meet to form excitons, and light is emitted when these excitons return to the ground state. At this time, the substance used as the organic layer is classified into a light-emitting substance, a hole injecting substance, a hole transporting substance, an electron transporting substance, an electron injecting substance, etc. according to its function.

[0004] The light-emitting layer materials of organic electroluminescent devices can be classified into blue, green, and red light-emitting materials according to the emission color. Furthermore, yellow and orange light-emitting materials are also used as light-emitting materials for realizing better natural colors. In addition, a host / dopant system is used as the light-emitting material for improving color purity and the luminous efficiency by energy transfer. The above dopant substances are roughly classified into a fluorescent dopant using an organic substance and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since such phosphorescent materials can theoretically improve the luminous efficiency by four times compared with fluorescence, not only phosphorescent dopants but also the interest in phosphorescent host materials has been concentrated. Currently, substances such as NPB, BCP, and Alq3 are widely known as substances used in the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as the light-emitting substance. In particular, among the light-emitting materials, metal complex compounds containing Ir such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2 are used as blue, green, and red dopant materials as phosphorescent materials having great merits in terms of efficiency improvement. Currently, CBP exhibits excellent characteristics as a phosphorescent host material.

[0005] However, although conventional light-emitting substances are advantageous in terms of light-emitting characteristics, they have a low glass transition temperature and poor thermal stability, so the lifespan in organic electroluminescent devices has been at an unsatisfactory level. Therefore, the development of light-emitting substances having excellent performance is required.

Summary of the Invention

Problems to be Solved by the Invention

[0006] An object of the present invention is to provide a novel organic compound applicable to an organic electroluminescent device and excellent in hole / electron injection and transport ability, light-emitting ability, and the like.

[0007] Another object of the present invention is to provide an organic electroluminescence device that contains the above novel organic compound, exhibits a low driving voltage and high luminous efficiency, and has improved lifetime characteristics.

[0008] Other objects and advantages of the present invention will become more apparent from the following detailed description and the appended claims.

Means for Solving the Problems

[0009] To achieve the above object, the present invention provides a compound represented by the following [Chemical Formula 1].

Chem.

[0010] The present invention also provides an organic electroluminescence device including a positive electrode, a negative electrode, and one or more organic material layers interposed between the positive electrode and the negative electrode, wherein at least one of the one or more organic material layers contains the compound represented by the above [Chemical Formula 1].

[0011] Here, the organic material layer containing the compound represented by the above [Chemical Formula 1] is selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, a lifetime improvement layer, an electron transport layer, and an electron transport auxiliary layer. At this time, the compound represented by the above [Chemical Formula 1] is included as at least one material of a phosphorescent host material of the light-emitting layer, an electron transport layer, and an electron transport auxiliary layer.

Effect of the Invention

[0012] According to one embodiment of the present invention, the compound represented by the above [Chemical Formula 1] is excellent in electron transport ability, light-emitting ability, heat resistance, etc., and thus can be used as an organic material layer material of an organic electroluminescence device.

[0013] In particular, when the compound represented by [Chemical Formula 1] of the present invention is used as a phosphorescent host, an electron transport layer, or an electron transport auxiliary layer material, it can exhibit high thermal stability, low driving voltage, high mobility, high current efficiency, and long-life characteristics as compared with conventional host materials or electron transport materials.

[0014] Therefore, an organic electroluminescence device containing the compound represented by the above [Chemical Formula 1] has greatly improved excellent light-emitting performance, low driving voltage, long life, and high efficiency, and can thus be effectively applied to a full-color display panel or the like.

[0015] The effects of the present invention are not limited to the contents described above, and more various effects are included in this specification.

Embodiments for Carrying Out the Invention

[0016] Hereinafter, the present invention will be described in detail.

[0017] <Novel Organic Compound> The present invention provides a novel aryl compound excellent in thermal stability, carrier transport ability, light-emitting ability, and the like.

[0018] Specifically, the novel organic compound according to the present invention contains a large number of aryl groups and a ring compound having a non-bonding electron pair, for example, a dibenzo-based / carbazole-based moiety, where an electron-withdrawing group (EWG) excellent in electron transport ability is bonded to form a basic skeleton.

[0019] The compound represented by the above [Chemical Formula 1] having such a structure structurally increases the electron density in an EWG having an electron transport ability by substituting a ring compound having a lone pair centered on an azine group (for example, triazine, pyrimidine, etc.), which is a kind of EWG, with a large number of aryl groups. As a result, compared with the existing material structure, the electron transport ability is further improved and the effect of higher efficiency is obtained. In addition, a ring compound bonded to the EWG, for example, a dibenzo-based or carbazole-based ring compound, has a rigid chemical structure, and thus has a high glass transition temperature (Tg) and excellent thermal stability.

[0020] Further, the compound represented by the above [Chemical Formula 1] forms a polycyclic structure by condensing an aryl group with a ring compound bonded to the EWG, thereby enhancing the electrical stability of the molecule, and thus enabling the device to have a longer lifespan than in the prior art. Usually, when a ring compound having a direct electron-donating property is bonded to the EWG, the HOMO orbital and the LUMO orbital are mainly formed in the ring compound, and the device may be intensively damaged electrically, resulting in a possible decrease in the device lifespan. To solve this problem, in the present invention, by having a ring compound having an electron-donating property, for example, a heterocyclic structure (for example, a Y-containing ring) in which an aryl group is condensed with a dibenzo-based moiety, the stability of the molecule can be significantly improved. In addition, to improve the electron transfer rate, by introducing triazine or pyrimidine, which is a functional group with high electron-withdrawing property, it is possible to impart physicochemical properties more suitable for electron injection and electron transport.

[0021] Furthermore, since the compound represented by [Chemical Formula 1] of the present invention has a higher triplet energy than the light-emitting layer, excitons generated in the light-emitting layer can be prevented from diffusing (moving) to the adjacent electron transport layer or hole transport layer. Therefore, the number of excitons contributing to light emission in the light-emitting layer increases, improving the light-emitting efficiency of the device, enhancing the durability and stability of the device, and efficiently obtaining a long lifespan of the device. Since most of the developed materials can be driven at a low voltage, they exhibit physical properties that improve the lifespan.

[0022] As described above, when the compound represented by [Chemical Formula 1] of the present invention is used as a material for the organic layer of an organic electroluminescence device, preferably as a light-emitting layer material (blue, green, and / or red phosphorescent host material), an electron transport layer / injection layer material, a hole transport layer / injection layer material, a light-emitting auxiliary layer material, or a lifetime improvement layer material, the performance and lifetime characteristics of the organic electroluminescence device can be significantly improved. Such an organic electroluminescence device can, as a result, maximize the performance of a full-color organic light-emitting panel.

[0023] The compound represented by [Chemical Formula 1] of the present invention has a basic skeleton formed by the bonding of a ring compound condensed with an electron-withdrawing group (EWG) having excellent electron transport ability and a large number of aryl groups.

[0024] The compound represented by [Chemical Formula 1] of the present invention has a basic skeleton formed by the bonding of a ring compound (for example, a Y-containing ring) and a large number of aryl groups (for example, an R1-containing ring) centered on an electron-withdrawing group (EWG) having excellent electron transport ability, such as a nitrogen-containing heterocyclic ring (for example, an X-containing ring).

[0025] The above nitrogen-containing heterocyclic ring (for example, an X-containing ring) is a monocyclic nitrogen-containing heteroaryl group containing at least two nitrogen atoms. In one embodiment of the nitrogen-containing heteroaromatic ring (for example, an X-containing ring), a plurality of Xs are the same as or different from each other, and each is independently N or CR5, provided that at least two of the plurality of Xs are N. In a specific example, the plurality of Xs contain 2 to 3 Ns, preferably 3 Ns. By including a heterocyclic ring containing 2 to 3 nitrogens in this way, better electron absorption characteristics are shown, which is advantageous for electron injection and transport.

[0026] Here, R5 is hydrogen, deuterium, an alkyl group having C1 to C 40 an alkenyl group having C2 to C 40 an alkynyl group having C2 to C 40 a cycloalkyl group having C3 to C 40 a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group having C6 to C 60 a heteroaryl group having 5 to 60 nuclear atoms, C1 to C40 an alkyloxy group, C6-C 60 an aryloxy group, C3-C 40 an alkylsilyl group, C6-C 60 an arylsilyl group, C1-C 40 an alkylboron group, C6-C 60 an arylboron group, C6-C 60 an arylphosphanyl group, C6-C 60 a monoarylphosphinyl group, C6-C 60 a diarylphosphinyl group, C6-C 60 an arylamine group, C5-C 60 an arylheteroarylamine group, and a heteroarylamine group having 5 to 60 ring atoms, and is selected from the group consisting of them. Specifically, R5 is hydrogen, deuterium, C1-C 40 an alkyl group, C6-C 60 an aryl group, and a heteroaryl group having 5 to 60 ring atoms, and is preferably selected from the group consisting of them.

[0027] In one specific example, the compound represented by the above [Chemical Formula 1] containing the nitrogen-containing heterocycle (X-containing ring) can be embodied in the following [Chemical Formula 2] to [Chemical Formula 5].

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0028] In the nitrogen-containing heterocycle (X-containing ring) according to the present invention, the Y-containing ring which is a ring compound and Ar1 may be substituted as various substituents. As such Ar1, C1-C 40 an alkyl group, C2-C40 an alkenyl group, C2-C 40 an alkynyl group, C3-C 40 a cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, C6-C 60 an aryl group, a heteroaryl group having 5 to 60 ring atoms, C1-C 40 an alkyloxy group, C6-C 60 an aryloxy group, C3-C 40 an alkylsilyl group, C6-C 60 an arylsilyl group, C1-C 40 an alkylboron group, C6-C 60 an arylboron group, C6-C 60 an arylphosphanyl group, C6-C 60 a monoarylphosphinyl group, C6-C 60 a diarylphosphinyl group, C6-C 60 an arylamine group, C5-C 60 an arylheteroarylamine group, and a heteroarylamine group having 5 to 60 ring atoms, and is selected from the group consisting of. Specifically, Ar1 is selected from the group consisting of an aryl group having 6 to C 60 an aryl group, and a heteroaryl group having 5 to 60 ring atoms, and more specifically, it is preferably an aryl group having 6 to C 18 an aryl group, and a heteroaryl group having 5 to 18 ring atoms.

[0029] Specific examples of Ar1 described above include the following structural formulas.

Chemical formula

[0030] Also, the ring compound introduced into the above nitrogen-containing heterocycle (X-containing ring) is represented by the Y-containing ring in the above [Chemical formula 1], and specifically, it is a condensed polycyclic heterocyclic structure in which a normal aryl group is condensed to a dibenzo-based / carbazole-based moiety.

[0031] In one specific example, in the Y-containing ring, Y is O, S, or NR4.

[0032] Here, R4 is hydrogen, deuterium, a C1-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40 alkynyl group, a C3-C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, a C6-C 60 aryl group, a heteroaryl group having 5 to 60 ring atoms, a C1-C 40 alkyloxy group, a C6-C 60 aryloxy group, a C3-C 40 alkylsilyl group, a C6-C 60 arylsilyl group, a C1-C 40 alkylboron group, a C6-C 60 arylboron group, a C6-C 60 arylphosphanyl group, a C6-C 60 monoarylphosphinyl group, a C6-C 60 diarylphosphinyl group, a C6-C 60 arylamine group, a C5-C 60 arylheteroarylamine group, and a heteroarylamine group having 5 to 60 ring atoms. Specifically, R4 is preferably selected from the group consisting of a C6-C 30 aryl group and a heteroaryl group having 5 to 30 ring atoms.

[0033] Also, circle A and circle B are the same as or different from each other, and each independently is a monocyclic or polycyclic hydrocarbon ring group having 5 to C 18 which may or may not contain a hetero atom. However, at least one of the above circle A and circle B is a C 10 to C 18It has a polycyclic hydrocarbon ring group. Such circle A and circle B may each independently be a condensed or fused polycyclic hydrocarbon ring or nitrogen-containing ring known in the art. By way of example, a polycyclic alicyclic ring, a polycyclic heteroalicyclic ring, a polycyclic aromatic ring, or a polycyclic heteroaromatic ring may be mentioned. Preferably, it is a polycyclic aromatic ring having 10 to 18 carbon atoms or a polycyclic heteroaromatic ring having 10 to 12 nuclear atoms containing a heteroatom. Here, the heteroatom is N, O, or S.

[0034] R2 and R3 are the same as or different from each other and are each independently deuterium, a C1~C 40 alkyl group, a C2~C 40 alkenyl group, a C2~C 40 alkynyl group, a C3~C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6~C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1~C 40 alkyloxy group, a C6~C 60 aryloxy group, a C3~C 40 alkylsilyl group, a C6~C 60 arylsilyl group, a C1~C 40 alkylboron group, a C6~C 60 arylboron group, a C6~C 60 arylphosphanyl group, a C6~C 60 monoarylphosphinyl group, a C6~C 60 diarylphosphinyl group, a C6~C 60 arylamine group, a C5~C 60 arylheteroarylamine group, and a heteroarylamine group having 5 to 60 nuclear atoms, or they may combine with adjacent groups to form a normal monocyclic or polycyclic condensed ring. Specifically, R2 and R3 are each independently preferably selected from the group consisting of a C6~C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

[0035] a is an integer from 0 to 2, and b is an integer from 0 to 4. Here, when a is 0, hydrogen exists without a substituent being substituted on circle A, and when a is 1 or 2, circle A may have the above-mentioned substituents except hydrogen. Similarly, when b is 0, hydrogen exists on circle B, and when b is 1 or 2, circle B may have the above-mentioned substituents.

[0036] However, the above Y-containing ring may be substituted or unsubstituted with the substituents described later, and the total number of carbon atoms contained in the Y-containing ring that is substituted and / or unsubstituted in this way is at least 16 or more. Specifically, it is 16 to 24.

[0037] In one specific example of the present invention, the Y-containing ring can be embodied as any one selected from the following structural formulas, but is not limited thereto.

Chemical formula

[0038] Specific examples of the above Y-containing ring include the following structural formulas.

Chemical formula

Chemical formula

Chemical formula

[0039] The compounds according to the present invention are such that a phenyl group substituted with a number of aryl groups (R1) and a nitrogen-containing heterocycle (e.g., an X-containing ring) are directly bonded (n = 0), or are linked via another linker (e.g., L). When such a linker (L) is present, it expands the HOMO region, a gain occurs in the HOMO-LUMO distribution, and the charge transfer efficiency increases due to an appropriate overlap of HOMO-LUMO.

[0040] The linker (e.g., L) is not particularly limited and may be an ordinary divalent linker well-known in the art. Specifically, L is selected from the group consisting of an arylene group having 6 to C 18 and a heteroarylene group having 5 to 18 ring atoms. More specifically, each is independently preferably selected from the group consisting of an arylene group having 6 to C 12 and a heteroarylene group having 5 to 12 ring atoms.

[0041] Specific examples of the above arylene group linker and heteroarylene group 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 indolylene group, a purinylene group, a quinolinylene group, a pyrrolylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a pyridinylene group, a pyrimidinylene group, a dibenzofuran-based moiety, a dibenzothiophene-based moiety, and / or a dibenzoselenophenone-based moiety. More specifically, as the above linker, a phenylene group and a biphenylene group are preferable.

[0042] The compound of [Chemical Formula 1] according to the present invention contains a number of aryl groups / heteroaryl groups (e.g., an R1-containing ring) on one side of a nitrogen-containing heterocycle (e.g., an X-containing ring).

[0043] Specifically, R1 is an aryl group having 6 to C 60 and a heteroaryl group having 5 to 60 ring atoms, and C6 to C 60It may be selected from the group consisting of arylsilyl groups. The number (m) of the introduced aryl group / heteroaryl group / arylsilyl group is an integer of 1 or more, and is preferably 1 to 5.

[0044] In one specific example, R1 is an aryl group having 6 to C 30 an aryl group, a heteroaryl group having 5 to 30 nuclear atoms, and an arylsilyl group having 6 to C 60 selected from the group consisting of, m is an integer of 2 to 5, and is substituted or unsubstituted with a substituent (R1) m contains at least 18 or more carbon atoms in total. More specifically, R1 is an aryl group having 6 to C 18 an aryl group, or an arylsilyl group having 6 to C 24 is an arylsilyl group, m is an integer of 3 to 5, and the total number of carbon atoms contained in R1, which is substituted or unsubstituted with a substituent described later, is 18 to 36.

[0045] In the above [Chemical Formula 1], the arylene group and heteroarylene group of the above L, the aryl group, heteroaryl group and arylsilyl group of the above R1, and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group of the above R2 to R5 and Ar1 are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1 to C 40 an alkyl group, C2 to C 40 an alkenyl group, C2 to C 40 an alkynyl group, C3 to C 40 a cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6 to C 60 an aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C1 to C 40 an alkyloxy group, C6 to C 60 an aryloxy group, C1 to C 40 an alkylsilyl group, C6 to C 60 an arylsilyl group, C1 to C 40an alkyl boron group, C6-C 60 an aryl boron group, C6-C 60 an aryl phosphine group, C6-C 60 an aryl phosphine oxide group, C6-C 60 an aryl amine group, C5-C 60 an aryl heteroaryl amine group, and may be substituted with one or more substituents selected from the group consisting of heteroaryl amine groups having 5 to 60 nuclear atoms, and when there are a plurality of these substituents, they may be the same as or different from each other.

[0046] In one embodiment of the present invention, the compound represented by the above [Chemical Formula 1] can be embodied as any one of the following [Chemical Formula 6] to [Chemical Formula 13] depending on the type of the linker (L) and the ring compound having a non-bonding electron pair (Y-containing ring), specifically, a dibenzo-based / carbazole-based moiety, but is not limited thereto.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0047] The compounds represented by the above [Chemical Formula 9] to [Chemical Formula 11] have a structure in which a polycyclic condensed ring (for example, D) is arranged adjacent to an azine group, and the compounds represented by the above [Chemical Formula 6] to [Chemical Formula 8] have a polycyclic condensed ring (for example, D) arranged relatively far from the azine group. When the condensed ring is not adjacent to the azine group in this way, the LUMO region is mainly distributed in the azine group and is not uniformly distributed to the condensed ring, so the electron transport ability becomes faster. In addition, since the conjugation length is longer than that of the non-condensed compound, the molecular stability can be enhanced and the device lifetime can be improved.

[0048] In another embodiment of the present invention, the compound represented by the above [Chemical Formula 1] can be embodied as any one of the following [Chemical Formula 14] to [Chemical Formula 25] depending on the number of a large number of aryl groups (R1) introduced into the molecule and their bonding positions, but is not limited thereto.

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chem.

Chem.

[0049] The compound represented by the [Chemical Formula 1] of the present invention as described above can be embodied in the following compounds, for example, compounds represented by Formulas 1 to 108, but is not limited to these examples.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

[0050] In the present invention, "alkyl" means a monovalent substituent derived from a linear 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.

[0051] In the present invention, "alkenyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

[0052] In the present invention, "alkynyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

[0053] In the present invention, "aryl" means 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. Note that two or more rings may be in a pendant or fused form. Examples thereof include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

[0054] In the present invention, "heteroaryl" means a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Note that two or more rings may be in a pendant or fused form, and thus may be in a form of fusion with an aryl group. Examples thereof include, but are not limited to, 6-membered monocyclic rings such as pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.

[0055] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples thereof include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

[0056] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' means an alkyl having 1 to 40 carbon atoms. Such alkyloxy may have a linear, branched, or cyclic structure. Examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentyloxy, and the like.

[0057] In the present invention, "arylamine" means an amine substituted with an aryl having 6 to 40 carbon atoms.

[0058] In the present invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples thereof include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, and the like.

[0059] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Examples thereof include, but are not limited to, morpholine, piperazine, and the like.

[0060] In the present invention, "alkylsilyl" means silyl substituted with an alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with an aryl having 5 to 40 carbon atoms.

[0061] In the present invention, the "condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

[0062] <Electron transport layer material> The present invention provides an electron transport layer containing the compound represented by the above [Chemical Formula 1].

[0063] The above electron transport layer (ETL) serves to move electrons injected from the negative electrode to an adjacent layer, specifically, the light-emitting layer.

[0064] 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, but it is preferably used alone.

[0065] As the electron transport layer material that can be mixed with the compound represented by the above [Chemical Formula 1], electron transport substances known in the art can be used. Examples of usable electron transport substances include oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylene-based compounds, aluminum complexes (e.g., Alq3 (tris(8-quinolinolato)-aluminum)), BAlq3, SAlq3, Almq3, gallium complexes (e.g., Gaq’2OPiv, Gaq’2OAc, 2(Gaq’2)), etc., but are not limited thereto. These may be used alone or in combination of two or more.

[0066] In the present invention, when the compound represented by the above [Chemical Formula 1] and an electron transport layer material are mixed, their mixing ratio is not particularly limited and can be appropriately adjusted within the range known in the art.

[0067] <Electron transport auxiliary layer material> Further, the present invention provides an electron transport auxiliary layer containing the compound represented by the above [Chemical Formula 1].

[0068] The above-mentioned electron transport 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.

[0069] The compound represented by the above [Chemical Formula 1] may be used alone as a material for the electron transport auxiliary layer, or may be mixed with an electron transport layer material known in the art, but it is preferably used alone.

[0070] As the electron transport auxiliary layer material that can be mixed with the compound represented by the above [Chemical Formula 1], an electron transport substance known in the art can be used. Examples of the above electron transport auxiliary layer include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), nitrogen-containing heterocyclic derivatives, and the like.

[0071] In the present invention, when the compound represented by the above [Chemical Formula 1] and the electron transport auxiliary layer material are mixed, their mixing ratio is not particularly limited and can be appropriately adjusted within the range known in the art.

[0072] <Organic electroluminescence device> Furthermore, the present invention relates to an organic electroluminescence device (hereinafter abbreviated as "organic EL device") containing the compound represented by the above [Chemical Formula 1].

[0073] Specifically, the present invention is an organic EL device including a positive electrode (anode), a negative electrode (cathode), and one or more organic layers interposed between the positive electrode and the negative electrode, wherein at least one of the one or more organic layers contains the compound represented by the above [Chemical Formula 1]. At this time, the above compound may be used alone or in a mixture of two or more.

[0074] The above-mentioned organic layer(s) of one or more layers is / are any one or more of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a lifetime improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of these organic layers contains the compound represented by the above [Chemical Formula 1]. Specifically, the organic layer containing the compound represented by the above [Chemical Formula 1] is preferably a light-emitting layer (more specifically, a phosphorescent host material), an electron transport layer, or an electron transport auxiliary layer.

[0075] The light-emitting layer of the organic EL element according to the present invention contains a host material and a dopant material. At this time, the host material may contain the compound represented by the above [Chemical Formula 1]. In addition, in the present invention, the light-emitting layer may contain, as a host, a compound known in the art in addition to the compound represented by the above [Chemical Formula 1].

[0076] When the compound represented by the above [Chemical Formula 1] is contained as a light-emitting layer material of an organic EL element, preferably as a phosphorescent host material for blue, green, or red, the binding force between holes and electrons in the light-emitting layer becomes strong, so that the efficiency (luminous efficiency and power efficiency), lifetime, luminance, driving voltage, etc. of the organic EL element can be improved. Specifically, the compound represented by the above [Chemical Formula 1] is preferably contained in the organic EL element as a green and / or red phosphorescent host, a fluorescent host, or a 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 of a high-efficiency light-emitting layer.

[0077] The structure of the organic EL element according to the present invention is not particularly limited, and may be a structure in which a substrate, a positive electrode, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and a negative electrode are sequentially laminated. At this time, one or more of the above hole injection layer, hole transport layer, light-emitting auxiliary layer, light-emitting layer, electron transport layer, and electron injection layer may contain the compound represented by the above [Chemical Formula 1], but preferably the light-emitting layer, more preferably the phosphorescent host contains the compound represented by the above [Chemical Formula 1]. Note that an electron injection layer may be further laminated on the above electron transport layer.

[0078] The structure of the organic EL element according to the present invention can also be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0079] The organic EL element according to the present invention can be manufactured by forming the organic layer and the electrode by materials and methods known in the art, except that one or more of the above-described organic layers contain the compound represented by the above [Chemical Formula 1].

[0080] The above organic layer can be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, a spin coating method, a dip coating method, a doctor blade method, an inkjet printing method, or a thermal transfer method.

[0081] The substrate used in the manufacture of the organic EL element according to the present invention is not particularly limited, and examples thereof include a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet.

[0082] Also, as the positive electrode material, a positive electrode substance known in the art can be used without limitation. For example, 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, etc., but are not limited thereto.

[0083] In addition, as the negative electrode material, known negative electrode substances in the art can be used without limitation. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer structured substances such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0084] Furthermore, the materials for the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and can be formed by using known substances in the art without limitation.

Examples

[0085] Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by these examples.

[0086] [Preparation Example 1] <Step 1>Synthesis of 3'-chloro-5'-phenyl-1,1':2',1''-terphenyl

Chemical formula

[0087] <Step 2: Synthesis of Core1

Chemical formula

[0088] [Preparation Example 2] <Step 1: Synthesis of 5'-chloro-5''-phenyl-1,1':3',1'':3'',1'''-quarterphenyl

Chemical formula

[0089] <Step 2:> Synthesis of Core2

Chem.

[0090] [Preparation Example 3] <Step 1> Synthesis of 4'-chloro-6'-phenyl-1,1':2',1'':3'',1'''-quaterphenyl

Chem.

[0091] <Step 2:> Synthesis of Core3

Chem.

[0092] [Preparation Example 4] <Step 1>Synthesis of Core4

Chemical formula

[0093] [Preparation Example 5] <Step 1>Synthesis of Core5

Chemical formula

[0094] [Preparation Example 6] <Step 1>Synthesis of 9-(3-chloro-5-(naphthalen-2-yl)phenyl)phenanthrene

Chemical formula

[0095] <Step 2:>Synthesis of Core6

Chemical formula

[0096] [Preparation Example 7] <Step 1>Synthesis of 5’-chloro-1,1’:3’,1”:3”,1’”-quaterphenyl

Chemical formula

[0097] <Step 2>Synthesis of Core7

Chemical formula

[0098] [Preparation Example 8] <Step 1>Synthesis of 5'-chloro-1,1':3',1":4",1'”-quaterphenyl

Chemical formula

[0099] <Step 2>Synthesis of Core8

Chemical formula

[0100] [Preparation Example 9] <Step 1> Synthesis of 2-(5'-chloro-[1,1':3',1”-terphenyl]-4-yl)naphthalene

Chemical formula

[0101] <Step 2> Synthesis of Core9

Chemical formula

[0102] [Synthesis Example 1] Synthesis of Compound 1

Chemical Structure

[0103] [Synthesis Example 2] Synthesis of Compound 3

Chemical Structure

[0104] [Synthesis Example 3] Synthesis of Compound 6

Chemical Structure

[0105] [Synthesis Example 4] Synthesis of Compound 10

Chemical Structure

[0106] [Synthesis Example 5] Synthesis of Compound 11

Chemical formula

[0107] [Synthesis Example 6] Synthesis of Compound 23

Chemical formula

[0108] [Synthesis Example 7] Synthesis of Compound 27

Chemical Structure

[0109] [Synthesis Example 8] Synthesis of Compound 28 [Chemical Formula] 20.0 g (1 eq, 34.8 mmol) of 4-(benzo[b]naphtho[1,2-d]thiophen-6-yl)-6-(5-chloro-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine, 15.8 g (1.05 eq, 36.5 mmol) of Core4 in [Preparation Example 4], 0.2 g (0.03 eq, 1.0 mmol) of Pd(OAc)2, 34.0 g (3.0 eq, 104.3 mmol) of Cs2CO3, and 1.0 g (0.06 eq, 2.1 mmol) of Xphos were placed in 300 ml of toluene, 75 ml of EtOH, and 75 ml of water, and the mixture was heated under reflux for 6 hours to carry out the reaction. After completion of the reaction, the mixture was extracted with dichloromethane, and MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, purification was performed by column chromatography using dichloromethane and hexane, and then recrystallization was carried out with toluene acetone to obtain 17.9 g (yield 61.1%) of Compound 28. Mass: [(M+H) + : 845

[0110] [Synthesis Example 9] Synthesis of Compound 37 [Chemical Formula] 2-(3-Chlorophenyl)-4-(naphtho[2,1-b]benzofuran-10-yl)-6-phenyl-1,3,5-triazine 10.0 g (1 eq, 20.7 mmol), (4’,5’-diphenyl-[1,1’:2’,1”-terphenyl]-3’-yl)boronic acid 9.2 g (1.05 eq, 21.7 mmol), Pd(OAc)2 0.1 g (0.03 eq, 0.62 mmol), Cs2CO3 20.2 g (3.0 eq, 61.9 mmol), and Xphos 0.6 g (0.06 eq, 1.2 mmol) were placed in 200 ml of toluene, 50 ml of EtOH, and 50 ml of water, and the reaction was carried out by heating under reflux for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, and MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, purification was carried out by column chromatography using dichloromethane and hexane, and then recrystallization was performed with toluene to obtain 6.7 g (yield 38.9%) of Compound 37. Mass:[(M+H) + :831

[0111] [Synthesis Example 10] Synthesis of Compound 38

Chemical Structure

[0112] [Synthesis Example 11] Synthesis of Compound 39 [Chemical Formula] Compound 39 was obtained in 13.1 g (yield 88.3%) by the same procedure at the same equivalent ratio as in [Synthesis Example 1], except that 10.0 g (17.8 mmol) of 2-(4-chlorophenyl)-4-(4-phenylnaphtho[2,3-b]benzofuran-1-yl)-6-(pyridin-2-yl)-1,3,5-triazine was used instead of 2-(4-chlorophenyl)-4-(naphtho[1,2-b]benzofuran-8-yl)-6-phenyl-1,3,5-triazine. Mass: [(M+H) + : 832

[0113] [Synthesis Example 12] Synthesis of Compound 41 [Chemical Formula] 15.0 g (1 eq, 31.1 mmol) of 4-(4-chlorophenyl)-6-(naphtho[2,1-b]benzofuran-9-yl)-2-phenylpyrimidine, 14.1 g (1.05 eq, 32.6 mmol) of Core8 in [Preparation Example 8], 0.2 g (0.03 eq, 0.9 mmol) of Pd(OAc)2, 30.4 g (3.0 eq, 93.2 mmol) of Cs2CO3, and 0.9 g (0.06 eq, 1.9 mmol) of Xphos were placed in 300 ml of toluene, 75 ml of EtOH, and 75 ml of water, and the reaction was carried out by heating under reflux for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, and MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, purification was performed by column chromatography using dichloromethane and hexane, and then recrystallization was performed with dichlorobenzene to obtain 19.7 g (yield 84.2%) of Compound 41. Mass: [(M+H) + : 754

[0114] [Synthesis Example 13] Synthesis of Compound 45 [Chemical Formula] 4-(3-Chlorophenyl)-6-(dinaphtho[2,1-b:1’,2’-d]thiophen-6-yl)-2-phenylpyrimidine 20.0 g (1 eq, 36.4 mmol), Core6 of [Preparation Example 6] 19.4 g (1.05 eq, 38.3 mmol), Pd(OAc)2 0.3 g (0.03 eq, 1.1 mmol), Cs2CO3 35.6 g (3.0 eq, 109.3 mmol), and Xphos 1.0 g (0.06 eq, 2.2 mmol) were placed in 300 ml of toluene, 75 ml of EtOH, and 75 ml of water, and refluxed with heating for 6 hours to carry out the reaction. After completion of the reaction, extraction was performed with dichloromethane, and MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, purification was carried out by column chromatography using dichloromethane and hexane, and then recrystallization was carried out with toluene / acetone to obtain 19.4 g (yield 59.7%) of Compound 45. Mass:[(M+H) + :893

[0115] [Synthesis Example 14] Synthesis of Compound 48

Chemical Structure

[0116] [Synthesis Example 15] Synthesis of Compound 50 [Chemical formula] Instead of 2-(4-chlorophenyl)-4-(naphtho[1,2-b]benzofuran-8-yl)-6-phenyl-1,3,5-triazine, 15.0 g (26.9 mmol) of 3-(4-(3-chlorophenyl)-6-phenylpyrimidin-2-yl)-5-phenyl-5H-benzo[b]carbazole was used, and Compound 50 was obtained in 17.1 g (yield 76.7%) by the same procedure with the same equivalent ratio as in [Synthesis Example 1]. Mass: [(M+H) + : 829

[0117] [Synthesis Example 16] Synthesis of Compound 51 [Chemical formula] Instead of 2-(4-chlorophenyl)-4-(naphtho[1,2-b]benzofuran-8-yl)-6-phenyl-1,3,5-triazine, 15.0 g (28.1 mmol) of 2-(4-chlorophenyl)-4-(phenanthro[9,10-b]benzofuran-12-yl)-6-phenylpyrimidine was used, and Compound 51 was obtained in 20.9 g (yield 92.3%) by the same procedure with the same equivalent ratio as in [Synthesis Example 1]. Mass: [(M+H) + : 804

[0118] [Synthesis Example 17] Synthesis of Compound 54 [Chemical formula] 5-(4-(4-Chlorophenyl)-6-phenyl-1,3,5-triazin-2-yl)-7-phenyl-7H-dibenzo[c,g]carbazole, 16.0 g (1 eq, 26.3 mmol), Core 7 from [Preparation Example 7], 11.9 g (1.05 eq, 27.6 mmol), Pd(OAc)2, 0.2 g (0.03 eq, 0.8 mmol), Cs2CO3, 25.7 g (3.0 eq, 78.8 mmol), and Xphos, 0.7 g (0.06 eq, 1.6 mmol) were placed in 200 ml of toluene, 50 ml of EtOH, and 50 ml of water, and the mixture was heated under reflux for 8 hours to carry out the reaction. After completion of the reaction, the mixture was extracted with dichloromethane, and MgSO4 was added and filtered. After removing the solvent from the filtered organic layer, purification was carried out by column chromatography using dichloromethane and hexane, and then recrystallization was carried out with toluene-acetone to obtain 15.3 g (yield 66.3%) of Compound 54. Mass:[(M+H) + :879

[0119] [Synthesis Example 18] Synthesis of Compound 57

Chemical Structure

[0120] [Synthesis Example 19] Synthesis of Compound 59 [Chemical Formula] 2-([1,1'-Biphenyl]-3-yl)-4-(4-chlorophenyl)-6-(naphtho[2,3-b]benzofuran-1-yl)-1,3,5-triazine 10.0 g (1 eq, 17.9 mmol), [1,1':3',1''-terphenyl]-5'-ylboronic acid 5.1 g (1.05 eq, 18.7 mmol), Pd(OAc)2 0.1 g (0.03 eq, 0.5 mmol), Cs2CO3 17.5 g (3.0 eq, 53.6 mmol), and Xphos 0.5 g (0.06 eq, 1.1 mmol) were placed in 300 ml of toluene, 75 ml of EtOH, and 75 ml of water, and the reaction was carried out by heating under reflux for 8 hours. After completion of the reaction, extraction was performed with dichloromethane, and MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, purification was performed by column chromatography using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 8.8 g (yield 65.7%) of Compound 59. Mass:[(M+H) + : 755

[0121] [Synthesis Example 20] Synthesis of Compound 67 [Chemical Formula] 4-Chloro-6-(naphtho[2,1-b]benzofuran-10-yl)-2-phenylpyrimidine 20.0 g (1 eq, 49.2 mmol), Core8 of [Preparation Example 8] 22.3 g (1.05 eq, 51.6 mmol), Pd(Pph3)4 2.1 g (0.05 eq, 2.5 mmol), and K2CO3 20.4 g (3.0 eq, 147.5 mmol) were placed in 300 ml of toluene, 75 ml of EtOH, and 75 ml of water, and the reaction was carried out by heating under reflux for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, and MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, purification was performed by column chromatography using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 28.2 g (yield 84.8%) of Compound 67. Mass:[(M+H) + :677

[0122] [Synthesis Example 21] Synthesis of Compound 72

Chemical formula

[0123] [Synthesis Example 22] Synthesis of Compound 76

Chemical formula

[0124] [Synthesis Example 23] Synthesis of Compound 80 [Chemical formula] 10.0 g (1 eq, 20.7 mmol) of 2-(4-chlorophenyl)-4-(naphtho[2,1-b]benzofuran-10-yl)-6-phenylpyrimidine, 11.1 g (1.05 eq, 21.7 mmol) of 2-([1,1’:3’,1”:3”,1’”,4’”,1””-kinkphenyl]-5”-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.1 g (0.03 eq, 0.62 mmol) of Pd(OAc)₂, 20.2 g (3.0 eq, 62.1 mmol) of Cs₂CO₃, and 0.6 g (0.06 eq, 1.2 mmol) of Xphos were placed in 200 ml of toluene, 50 ml of EtOH, and 50 ml of water, and the reaction was carried out by heating under reflux for 7 hours. After completion of the reaction, extraction was performed with dichloromethane, and MgSO₄ was added and filtered. After removing the solvent of the filtered organic layer, purification was carried out by column chromatography using dichloromethane and hexane, and then recrystallization was performed with monochlorobenzene to obtain 12.7 g (yield 74.4%) of Compound 80. Mass: [(M + H) + : 830

[0125] [Synthesis Example 24] Synthesis of Compound 81 [Chemical formula] Compound 81 was obtained in 19.2 g (yield 82.2%) by the same procedure with the same equivalent ratio as in [Synthesis Example 6], except that 15.0 g (31.0 mmol) of 2-(4-chlorophenyl)-4-(naphtho[1,2-b]benzofuran-8-yl)-6-phenyl-1,3,5-triazine was used instead of 4-(benzo[b]naphtho[1,2-d]thiophen-6-yl)-6-(5-chloro-[1,1’-biphenyl]-3-yl)-2-phenylpyrimidine. Mass: [(M + H) + : 755

[0126] [Synthesis Example 25] Synthesis of Compound 82 [Chemical formula] 2-(3-Chlorophenyl)-4-phenyl-6-(11-phenylbenzo[b]naphtho[1,2-d]thiophen-8-yl)-1,3,5-triazine, 17.0 g (1 eq, 29.5 mmol), Core9 from [Preparation Example 9], 14.9 g (1.05 eq, 31.0 mmol), Pd(OAc)2, 0.9 g (0.03 eq, 0.89 mmol), Cs2CO3, 28.8 g (3.0 eq, 74.1 mmol), and Xphos, 0.8 g (0.06 eq, 1.8 mmol) were placed in 200 ml of toluene, 50 ml of EtOH, and 50 ml of water, and the mixture was heated under reflux for 7 hours to effect the reaction. After completion of the reaction, the mixture was extracted with dichloromethane, and MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, purification was performed by column chromatography using dichloromethane and hexane, and then recrystallization was carried out with toluene / acetone to obtain 16.3 g (yield 61.8%) of Compound 82. Mass: [(M+H) + : 896

[0127] [Synthesis Example 26] Synthesis of Compound 83

Chemical Structure

[0128] [Synthesis Example 27] Synthesis of Compound 84 [Chemical Formula] 12.0 g (1 eq, 24.8 mmol) of 2-(4-chlorophenyl)-4-(naphtho[2,3-b]benzofuran-3-yl)-6-phenyl-1,3,5-triazine, 11.3 g (1.05 eq, 26.0 mmol) of Core8 of [Preparation Example 8], 0.2 g (0.03 eq, 0.74 mmol) of Pd(OAc)2, 24.2 g (3.0 eq, 74.4 mmol) of Cs2CO3, and 0.7 g (0.06 eq, 1.5 mmol) of Xphos were placed in 400 ml of toluene, 100 ml of EtOH, and 100 ml of water, and the reaction was carried out by heating under reflux for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, and MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, purification was carried out by column chromatography using dichloromethane and hexane, and then recrystallization was carried out with dichlorobenzene to obtain 17.1 g (yield 91.2%) of Compound 84. Mass:[(M+H) + :755

[0129] [Synthesis Example 28] Synthesis of Compound 89 [Chemical Formula] 2-(5’-Chloro-[1,1’:3’,1”-terphenyl]-4-yl)-4(naphtho[1,2-b]benzofuran-8-yl)-6-phenylpyrimidine 10.0 g (1 eq, 15.7 mmol), [1,1’:3’,1”-terphenyl]-4’-ylboronic acid 4.5 g (1.05 eq, 16.5 mmol), Pd(OAc)2 0.1 g (0.03 eq, 0.47 mmol), Cs2CO3 15.4 g (3.0 eq, 47.2 mmol), and Xphos 0.4 g (0.06 eq, 0.9 mmol) were placed in 200 ml of toluene, 50 ml of EtOH, and 50 ml of water, and the reaction was carried out by heating under reflux for 6 hours. After completion of the reaction, extraction was performed with dichloromethane, and MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, purification was carried out by column chromatography using dichloromethane and hexane, and then recrystallization was performed with dichlorobenzene to obtain 5.9 g (yield 44.9%) of compound 89. Mass:[(M+H) + :830

[0130] [Synthesis Example 29] Synthesis of Compound 94 [Chemical Formula] 4-(3-Chlorophenyl)-6-(naphtho[2,1-b]benzofuran-10-yl)-2-phenylpyrimidine 10.0 g (1 eq, 20.7 mmol), 4,4,5,5-tetramethyl-2-(5’-phenyl-[1,1’:2’,1”-terphenyl]-4’-yl-2,3,4,5,6-d5)-1,3,2-dioxaborolane 9.5 g (1.05 eq, 21.7 mmol), Pd(OAc)2 0.1 g (0.03 eq, 0.62 mmol), Cs2CO3 20.2 g (3.0 eq, 62.1 mmol), and Xphos 0.6 g (0.06 eq, 1.2 mmol) were placed in 200 ml of toluene, 50 ml of EtOH, and 50 ml of water, and the reaction was carried out by heating under reflux for 6 hours. After completion of the reaction, extraction was performed with dichloromethane, and MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, purification was carried out by column chromatography using dichloromethane and hexane, and then recrystallization was performed with monochlorobenzene to obtain 14.0 g (yield 89.3%) of compound 94. Mass:[(M+H) + :759

[0131] [Synthesis Example 30] Synthesis of Compound 95

Chemical formula

[0132] [Examples 1 to 10] Fabrication of Blue Organic EL Devices The compound synthesized in the above synthesis example was subjected to high-purity sublimation purification by a conventional method, and then a blue organic EL device was fabricated according to the following procedure.

[0133] First, a glass substrate with a 1200 Å-thick thin film coating of ITO (Indium Tin Oxide) was washed with ultrasonic distilled water. After completion of the washing with distilled water, ultrasonic washing was carried out with solvents such as isopropyl alcohol, acetone, and methanol, and after drying, it was transferred to a UV ozone washer (Power sonic 405, manufactured by Facsintec Co., Ltd.), and then the above substrate was washed with UV for 5 minutes, and the substrate was transferred to a vacuum evaporator.

[0134] On the thus-prepared ITO transparent electrode, an organic EL device was fabricated by laminating in the order of HT-1 + 2% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / BH + 2% BD (200 Å) / ET-2 (50 Å) / each of the compounds of Compound 1, 3, 11, 27, 41, 57, 59, 81, 83, 84:LiQ = 1:1 (300 Å) / LiF (10 Å) / Al (1000 Å).

[0135] 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. [Chemical formula]

[0136] [Comparative Example 1] Fabrication of blue organic EL device A blue organic EL device was fabricated in the same manner as in Example 1 above, except that 30 nm of Alq3 was deposited instead of Compound 1 as the electron transport layer material.

[0137] [Evaluation Example 1] For each of the blue organic EL devices fabricated in Examples 1 to 10 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.

[0138] [Table 1]

[0139] As shown in Table 1 above, the blue organic EL devices obtained in Examples 1 to 10 using the compound according to the present invention as the electron transport layer material showed excellent performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic EL device obtained in Comparative Example 1 using conventional ET-1.

[0140] [Examples 11 to 28] Fabrication of blue organic EL device After subjecting the compound synthesized in the above synthesis example to high-purity sublimation purification by a conventional method, a blue organic EL device was fabricated according to the following procedure.

[0141] First, a glass substrate with a thin film coating of ITO (Indium Tin Oxide) having a thickness of 1500 Å was cleaned with distilled water ultrasonic. After the cleaning with distilled water was completed, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV ozone cleaner (Power sonic 405, manufactured by Facsinttech Co., Ltd.). After that, the above substrate was cleaned with UV for 5 minutes and then transferred to a vacuum evaporator.

[0142] On the thus-prepared ITO transparent electrode, HT-1 + 2% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / BH + 2% BD (200 Å) / Compound 6, 10, 23, 27, 37 - 39, 48, 51, 54, 57, 67, 72, 80 - 81, 89, 94 - 95 (50 Å) / ET-1:LiQ = 1:1 (300 Å) / LiF (10 Å) / Al (1000 Å) were laminated in this order to fabricate the organic EL devices of Examples 11 - 28.

[0143] [Comparative Examples 2 - 4] Fabrication of Blue Organic EL Devices Blue organic EL devices of Comparative Examples 2 - 4 were fabricated in the same manner as in Example 11 above, except that Compounds ET-2 - ET-4 were used instead of Compound 6 as the electron transport auxiliary layer material.

[0144] The structures of ET-2, ET-3, and ET-4 used at this time are as follows.

Chemical Formula

[0145] [Evaluation Example 2] For the organic EL devices fabricated in Examples 11 - 28 and Comparative Examples 2 - 5 respectively, the driving voltage, emission peak, and current efficiency at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.

[0146]

Table 2

[0147] As shown in Table 2 above, the blue organic EL elements obtained in Examples 11 to 28 containing the compound according to the present invention as an electron transport auxiliary layer material were found to exhibit excellent performance in terms of current efficiency and driving voltage compared to the organic EL elements obtained in Comparative Examples 2 to 4.

Claims

1. A compound represented by the following [Chemical Formula 1]. 【Chemical 1】 (In the formula, The plurality of Xs are the same as or different from each other, and each independently is CR ５ or N, provided that at least two of the plurality of Xs are N, Ar １ is an alkyl group of C １ to C ４０ , an alkenyl group of C ２ to C ４０ , an alkynyl group of C ２ to C ４０ , a cycloalkyl group of C ３ to C ４０ , a heterocycloalkyl group having 3 to 40 ring atoms, an aryl group of C ６ to C ６０ , a heteroaryl group having 5 to 60 ring atoms, an alkyloxy group of C １ to C ４０ , an aryloxy group of C ６ to C ６０ , an alkylsilyl group of C ３ to C ４０ , an arylsilyl group of C ６ to C ６０ , an alkylboron group of C １ to C ４０ , an arylboron group of C ６ to C ６０ , an arylphosphanyl group of C ６ to C ６０ , a monoarylphosphinyl group of C ６ to C ６０ , a diarylphosphinyl group of C ６ to C ６０ , an arylamine group of C ６ to C ６０ , an arylheteroarylamine group of C ５ to C ６０ , and is selected from the group consisting of a heteroarylamine group having 5 to 60 ring atoms. Y is O, S, or NR ４ and Circle A and circle B are the same as or different from each other, and each independently is a monocyclic or polycyclic hydrocarbon ring containing or not containing a heteroatom, provided that at least one of circle A and circle B is a polycyclic hydrocarbon ring of C ５ ~C １８ to C １０ ~C １８ to C, R ２ to R ３ are the same as or different from each other and are each independently deuterium, a C １ to C ４０ alkyl group, a C ２ to C ４０ alkenyl group, a C ２ to C ４０ alkynyl group, a C ３ to C ４０ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ６ to C ６０ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C １ to C ４０ alkyloxy group, a C ６ to C ６０ aryloxy group, a C ３ to C ４０ alkylsilyl group, a C ６ to C ６０ arylsilyl group, a C １ to C ４０ alkylboron group, a C ６ to C ６０ arylboron group, a C ６ to C ６０ arylphosphanyl group, a C ６ to C ６０ monoarylphosphinyl group, a C ６ to C ６０ diarylphosphinyl group, a C ６ to C ６０ arylamine group, a C ５ to C ６０ aryls heteroaryl amine group, and a heteroaryl amine group having 5 to 60 nuclear atoms, or these may combine with adjacent groups to form a condensed ring. R ４ ~R ５ are the same as or different from each other, and each independently is hydrogen, deuterium, a C １ ~C ４０ alkyl group, a C ２ ~C ４０ alkenyl group, a C ２ ~C ４０ alkynyl group, a C ３ ~C ４０ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ６ ~C ６０ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C １ ~C ４０ alkyloxy group, a C ６ ~C ６０ aryloxy group, a C ３ ~C ４０ alkylsilyl group, a C ６ ~C ６０ arylsilyl group, a C １ ~C ４０ alkylboron group, a C ６ ~C ６０ arylboron group, a C ６ ~C ６０ arylphosphanyl group, a C ６ ~C ６０ monoarylphosphinyl group, a C ６ ~C ６０ diarylphosphinyl group, a C ６ ~C ６０ arylamine group, a C ５ ~C ６０ aryleneheteroarylamine group, and a heteroarylamine group having 5 to 60 nuclear atoms, and is selected from the group consisting of L is C ６ to C １８ selected from the group consisting of arylene groups and heteroarylene groups having 5 to 18 nuclear atoms, R １ is selected from the group consisting of an aryl group of C ６ to C ６０ , a heteroaryl group having 5 to 60 nuclear atoms, and an arylsilyl group of C ６ to C ６０ ; m is an integer of 1 or more, n is an integer of 0 to 3, a is an integer of 0 to 2, b is an integer of 0 to 4, The arylene group and heteroarylene group of the above L, the above R １ 's aryl group, heteroaryl group, arylsilyl group, and the above R ２ to R ５ and Ar １ 's 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 are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C １ to C ４０ 's alkyl group, C ２ to C ４０ 's alkenyl group, C ２ to C ４０ 's alkynyl group, C ３ to C ４０ 's cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ６ to C ６０ 's aryl group, heteroaryl group with 5 to 60 nuclear atoms, C １ to C ４０ 's alkyloxy group, C ６ to C ６０ 's aryloxy group, C １ to C ４０ 's alkylsilyl group, C ６ to C ６０ 's arylsilyl group, C １ to C ４０ 's alkylboron group, C ６ to C ６０ 's arylboron group, C ６ to C ６０ 's arylphosphine group, C ６ to C ６０ 's arylphosphine oxide group, C ６ to C ６０ 's arylamine group, C ５ to C ６０ is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl heteroaryl amine group and a heteroaryl amine group having 5 to 60 nuclear atoms, and when there are a plurality of the above substituents, they may be the same as or different from each other, provided that the total number of carbon atoms contained in the Y-containing ring which is substituted or unsubstituted with a substituent is at least 16 or more.)

2. R １ is selected from the group consisting of an aryl group of C ６ to C ３０ , a heteroaryl group having 5 to 30 nuclear atoms, and an arylsilyl group of C ６ to C ３０ ; m is an integer of 1 to 5, substituted or unsubstituted with a substituent (R １ ), ｍ wherein the total number of carbon atoms contained in ｍ is at least 18, the compound according to claim 1.

3. The compound according to claim 1, wherein the Y-containing ring is selected from the group of substituents represented by the following formula. 【Chemical 2】 (In the formula, * is the bonding site with the above [Chemical Formula 1], circle D is the same as or different from each other, and each independently is a monocyclic or polycyclic hydrocarbon ring which may or may not contain a heteroatom.) Y, R ２ , R ３ , a, and b are as defined in claim 1, respectively.)

4. The compound according to claim 1, wherein the Y-containing ring is selected from the group of substituents represented by the following formula. 【Chemical 3】 【Chemical 4】 【Chemical Formula 5】 (In the formula, * is the bonding site with the above [Chemical Formula 1], R ４ is as defined in claim 1.)

5. 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 Formula 2] to [Chemical Formula 5]. 【Chemical Formula 6】 【Chemical Formula 7】 [Chemical Formula 8] 【Chemical Formula 9】 (In the formula, * is the bonding site with the above [Chemical Formula 1], A, B, Y, L, R １ ~R ３ , Ar １ , a, b, m, and n are as defined in claim 1, respectively.)

6. Ar １ and R ２ to R ３ are the same as or different from each other and are each independently selected from the group consisting of an aryl group of C ６ to C ６０ and a heteroaryl group having 5 to 60 nuclear atoms, R ４ is selected from the group consisting of an aryl group of C ６ to C ３０ and a heteroaryl group having 5 to 30 nuclear atoms, the compound according to claim 1.

7. Ar １ The compound according to claim 1, wherein Ar is selected from the group of substituents represented by the following formulae. 【Chemical 10】

8. 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 Formula 6] to [Chemical Formula 13]. 【Chemical Formula 11】 【Chemical 12】 【Chemical 13】 【Chemical 14】 【Chemical Formula 15】 【Chemical 16】 【Chemical 17】 【Chemical 18】 (In the formula, circle D is a monocyclic or polycyclic hydrocarbon ring which may or may not contain a heteroatom.) X, Y, R １ ~R ３ , Ar １ , a, b, m, and n are as defined in claim 1, respectively.)

9. The compound represented by the above [Chemical Formula 1] is a compound represented by any one of the following [Chemical Formula 14] to [Chemical Formula 25]. 【Chemical Formula 19】 【Chemical 20】 【Chemical 21】 【Chemical 22】 【Chemical 23】 【Chemical 24】 【Chemical Formula 25】 【Chemical 26】 【Chemical 27】 【Chemical Formula 28】 【Chemical 29】 【Chemical Formula 30】 (In the formula, X, Y, A, B, Ar １ , L, R １ ~R ３ , a, b, and n are as defined in claim 1, respectively.)

10. The compound according to claim 1, wherein the compound represented by the above [Chemical Formula 1] is represented by any one of the following Formula 1 to 108. 【Chemical 31】 【Chemical 32】 【Chemical 33】 【Chemical 34】 【Chemical 35】 【Chemical 36】 【Chemical 37】

11. 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.

12. An organic electroluminescence element including a positive electrode, a negative electrode, and one or more organic layers interposed between the positive electrode and the negative electrode, wherein at least one of the one or more organic layers contains the compound according to any one of claims 1 to 11.

13. The organic layer containing the above compound is selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, a lifetime improvement layer, an electron transport layer, and an electron transport auxiliary layer. The organic electroluminescence device according to claim 12.

14. The organic electroluminescence device according to claim 13, wherein the above compound is included as at least one material among a phosphorescent host material of the light-emitting layer, an electron transport layer material, and an electron transport auxiliary layer material.

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