Organic compound and organic electroluminescence device using the same

Abstract

The present invention relates to a novel compound having excellent carrier transport ability, light emitting ability, and thermal stability, and to an organic electroluminescence device having improved properties such as light emitting efficiency, driving voltage, and lifespan by incorporating the compound in one or more organic layers.

Description

[Technical field]

[0001] The present invention relates to a novel organic light-emitting compound and an organic electroluminescence device using the same, and more particularly to a compound having excellent electron transport ability, light-emitting ability, and thermal stability, and an organic electroluminescence device having improved properties such as light-emitting efficiency, driving voltage, and lifespan by incorporating the compound in one or more organic layers. [Background technology]

[0002] Since the discovery of luminescence in organic thin films by Bernanose in the 1950s, research on organic electroluminescent elements led to the blue light emission using single crystals of anthracene in 1965, and in 1987 Tang et al. proposed an organic electroluminescent element with a laminated structure that separates the functional layers into a hole layer and a light-emitting layer. Since then, in order to obtain highly efficient, long-life organic electroluminescent elements, development has progressed to introduce characteristic organic layers within the element, and specialized materials to be used for this are being developed.

[0003] When a voltage is applied between the two electrodes of an organic electroluminescence element, holes are injected from the anode and electrons are injected from the cathode into the organic layer. The injected holes and electrons combine to form excitons, which emit light when they return to the ground state. The materials used in the organic layer are classified according to their functions into light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, electron-injecting materials, etc.

[0004] The materials forming the light-emitting layer of an organic electroluminescence device are classified into blue, green, and red light-emitting materials according to the color of the light emitted. In addition, yellow and orange light-emitting materials may be used as light-emitting materials to realize better natural colors. In addition, host-dopant-based light-emitting materials are used as light-emitting materials to improve color purity and improve luminous efficiency by energy transfer. Dopant materials are classified into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. Theoretically, such phosphorescent materials can improve luminous efficiency by four times compared to fluorescence, and interest is being drawn not only to the development of phosphorescent dopants but also to phosphorescent host materials. To date, NPB, BCP, Alq3, etc. are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives have been reported as fluorescent dopant-host materials for luminescent materials. In particular, among light-emitting materials, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, (acac)Ir(btp)2, etc., are phosphorescent materials that have great merits in terms of improving efficiency, and are used as blue, green, and red dopant materials. Currently, CBP shows excellent properties as a phosphorescent host material.

[0005] However, although conventional organic layer materials are advantageous in terms of light-emitting properties, they have low glass transition temperatures and poor thermal stability, which means that the life of organic electroluminescence elements is not satisfactory. Therefore, there is a demand for the development of organic layer materials with excellent performance. Summary of the Invention [Problem to be solved by the invention]

[0006] An object of the present invention is to provide a novel organic compound which is applicable to organic electroluminescence devices and has excellent hole / electron injection and transport properties and light-emitting properties.

[0007] Another object of the present invention is to provide an organic electroluminescence device that contains the above-mentioned novel organic compound and thereby exhibits a low driving voltage, high luminous efficiency and a long life.

[0008] Other objects and advantages of the present invention will be more clearly set forth in the following detailed description and claims. [Means for solving the problem]

[0009] In order to achieve the above object, the present invention provides a compound represented by the following Chemical Formula 1:

[0010] [ka] (In the above chemical formula 1, A plurality of X may be the same or different, and each independently represents CR2 or N, provided that at least two of the plurality of X are N; R2 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C1-C 40 Alkyl groups, C2-C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C3-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphanyl groups, C6-C 60 Monoarylphosphinyl groups, C6-C 60 Diarylphosphinyl groups, C6-C 60 Arylamine groups, C5-C 60and heteroarylamine groups having 5 to 60 ring atoms, L is a single bond or C6-C 18 and heteroarylene groups having 5 to 18 ring atoms, R1 is C6~C 60 and heteroaryl groups having 5 to 60 ring atoms, m is an integer of 1 or more, and n is an integer of 0 to 3, Ar2 is C1 to C 40 Alkyl groups, C2-C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C3-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphanyl groups, C6-C 60 Monoarylphosphinyl groups, C6-C 60 Diarylphosphinyl groups, C6-C 60 Arylamine groups, C5-C 60 and heteroarylamine groups having 5 to 60 ring atoms, Ar1 is a moiety represented by the following chemical formula 2: [ka] In the above Chemical Formula 2, * is a binding site to Chemical Formula 1 above, Y is O, S, or NR 11 and Circle A and circle B may be the same or different, and each independently represents a C5-C 18 is a monocyclic or polycyclic hydrocarbon ring group of the formula R 11 and R 12 may be the same or different, and each independently represents C1 to C 12 Alkyl groups of C6 to C 12 or a heteroaryl group having 5 to 12 ring atoms, which may be bonded to an adjacent group to form a condensed ring, a is 0 to 2; The arylene group and heteroarylene group of L, the aryl group and heteroaryl group of R1, and the R2 and R 11 ~R 12 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, arylphosphanyl group, monoarylphosphinyl group, diarylphosphinyl group, arylamine group, arylheteroarylamine group, and heteroarylamine group of Ar2 each independently represent deuterium (D), halogen, cyano group, nitro group, C1 to C6 40 Alkyl groups, C2-C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide group, C6-C60 Arylamine groups, C5-C 60 and a heteroarylamine group having 5 to 60 ring atoms, and in this case, when there are a plurality of the above-mentioned substituents, these may be the same or different from each other, However, the total number of carbon atoms contained in Ar1, whether substituted or unsubstituted, is 16 to 24.

[0011] The present invention also 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 Chemical Formula 1.

[0012] The organic layer containing the compound represented by Chemical Formula 1 may be selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, a life-improving layer, an electron transport layer, and an electron transport auxiliary layer. In this case, the compound represented by Chemical Formula 1 may be included as at least one of the phosphorescent host material of the light-emitting layer, the electron transport layer, and the electron transport auxiliary layer. Effect of the Invention

[0013] According to one embodiment of the present invention, the compound represented by Chemical Formula 1 has excellent electron transporting ability, light emitting ability, heat resistance, etc., and can be used as an organic layer material of an organic electroluminescence device.

[0014] 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 provide higher thermal stability, lower driving voltage, higher mobility, higher current efficiency, and longer life properties than conventional host materials or electron transport materials.

[0015] As a result, the organic electroluminescence device including the compound represented by Chemical Formula 1 has excellent light emitting performance, low driving voltage, long life, high efficiency, and other advantages, and can be effectively used in full-color display panels, etc.

[0016] The effects of the present invention are not limited to the above-mentioned contents, and more various effects are included in the present specification. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0017] The present invention will be described in detail below.

[0018] <New organic compounds> The present invention relates to a novel aryl compound having excellent thermal stability, carrier transport ability, light emitting ability, etc., and by containing the compound, it is intended to simultaneously realize low voltage, high efficiency, and long life characteristics of an element.

[0019] Specifically, the novel organic compound represented by Chemical Formula 1 of the present invention contains a number of aryl groups and a ring compound having an unshared electron pair, for example, a dibenzo / carbazole moiety, to which an electron-withdrawing group (EWG) having excellent electron transport ability is bonded to form a basic skeleton.

[0020] The compound represented by Chemical Formula 1 having such a structure is a ring compound having a shared electron pair on one side and a number of aryl groups on the other side of an azine group (e.g., triazine, pyrimidine, etc.), which is a type of electron-withdrawing group, structurally increasing the electron density in the electron-withdrawing group with electron transporting ability, and thus improving the electron transporting ability and increasing efficiency compared to existing known material structures. In addition, since it has a rigid chemical structure due to the dibenzo- or carbazole-based ring compound bonded to the electron-withdrawing group, it has excellent high glass transition temperature (Tg) and thermal stability. In addition, the chemical design in which the conjugation length is relatively increased due to the dibenzo- or carbazole-based ring compound bonded to the electron-withdrawing group can increase the stability of the molecule, thereby obtaining a device with a longer life than conventional technology. In addition, by introducing an azine group, which is a functional group having a strong electron-withdrawing force (EWG) to improve the electron transfer speed, it has physicochemical properties that are more suitable for electron injection and electron transport.

[0021] In addition, the compound represented by Chemical Formula 1 of the present invention has high triplet energy, so that 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, and improving the durability and stability of the device, resulting in an efficient increase in device life. Most of the developed materials exhibit physical characteristics that allow low-voltage operation, thereby improving life.

[0022] As described above, when the compound represented by Chemical Formula 1 of the present invention is used as an organic layer material of an organic electroluminescence device, preferably as an 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, an emitting auxiliary layer material, or a life improvement layer material, the performance and life characteristics of the organic electroluminescence device can be significantly improved. Such an organic electroluminescence device can maximize the performance of a full-color organic EL panel.

[0023] The compound represented by Chemical Formula 1 according to the present invention has a basic skeleton formed by bonding a dibenzo / carbazole ring compound (e.g., Ar1) and a number of aryl groups (e.g., R1-containing ring) to an electron-withdrawing group (EWG) having excellent electron transport ability, e.g., a nitrogen-containing heterocycle (e.g., X-containing ring) at the center.

[0024] The nitrogen-containing heterocycle (e.g., 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 (e.g., X-containing ring), the multiple Xs may be the same or different from each other and are each independently N or CR2, provided that at least two of the multiple Xs are N. In one specific example, the multiple Xs contain 2 to 3 Ns, preferably 3 Ns. By containing a heterocycle containing 2 to 3 nitrogens in this way, the ring exhibits better electron absorption properties and is advantageous for electron injection and transport.

[0025] In a specific example, the nitrogen-containing heterocycle (X-containing ring) may be any one selected from the following structural formulas, but is not limited thereto. [ka] In the above formula, * indicates the binding site to Chemical Formula 1 above.

[0026] Here, there may be a plurality of CR2s located on the nitrogen-containing heterocycle (e.g., X-containing ring), and in this case, R2s may be the same or different from each other and each independently represents hydrogen, deuterium (D), halogen, cyano group, nitro group, C1 to C 40 Alkyl groups, C2-C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60Aryloxy groups, C3-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphanyl groups, C6-C 60 Monoarylphosphinyl groups, C6-C 60 Diarylphosphinyl groups, C5-C 60 Arylamine groups, C5-C 60 and heteroarylamine groups having 5 to 60 ring atoms. Specifically, R2 can be selected from the group consisting of hydrogen, deuterium (D), a cyano group, C1 to C 40 Alkyl groups of C6 to C 60 and heteroaryl groups having 5 to 60 ring atoms.

[0027] In the nitrogen-containing heterocycle (X-containing ring) according to the present invention, Ar1 and Ar2 may be substituted with various substituents. In this case, Ar1 and Ar2 may be different from each other, and any one of Ar1 and Ar2 may have a dibenzo-based / carbazole-based ring.

[0028] In one embodiment, Ar1 has a moiety represented by the following formula 2: [ka] In the above formula, * is a binding site to Chemical Formula 1; Y is O, S, or NR 11 and Circle A and circle B may be the same or different, and each independently represents a C5-C 18The ring A and ring B may be a monocyclic or polycyclic hydrocarbon ring group. Each of these rings A and B may be a condensed or fused monocyclic or polycyclic hydrocarbon ring or a nitrogen-containing ring well known in the art, and may be, for example, a monocyclic or polycyclic alicyclic ring, a monocyclic or polycyclic heteroalicyclic ring, or a monocyclic or polycyclic heteroaromatic ring. Preferably, the ring A and ring B may be a monocyclic or polycyclic aromatic ring having 6 to 12 carbon atoms, or a monocyclic or polycyclic heteroaromatic ring having 5 to 12 nuclear atoms and containing at least one heteroatom. Here, the heteroatom may be N, O, or S. R 11 and R 12 may be the same or different, and each independently represents C1 to C 12 Alkyl groups of C6 to C 12 or a heteroaryl group having 5 to 12 ring atoms, or these may be bonded to an adjacent group to form a condensed ring. a is 0 to 2. When a is 0, R 12 means hydrogen, and when a is 1-2, R 12 R may have the substituents as described above. 12 When there are a plurality of, they may be the same or different. However, Ar1 represented by the above chemical formula 2 may be substituted with a substituent described below or may not be substituted, and the total number of carbon atoms contained in Ar1, whether substituted or unsubstituted in this manner, is 16 to 24.

[0029] In one embodiment of the present invention, Ar1 can be embodied as any one selected from the following structural formulas, but is not limited thereto. [ka] In the above formula, * is a binding site to Chemical Formula 1 above, Circles D may be the same or different and each independently represents a monocyclic or polycyclic hydrocarbon ring group with or without a heteroatom; Y and R 12are as defined in Chemical Formula 1.

[0030] A specific example of the above Ar1 is the following structural formula: [ka] [ka] [ka] In the above formula, * is a bonding site with Chemical Formula 1, R 11 and R 12 are as defined in Chemical Formula 2. Although not shown in the above structural formula, at least one substituent well known in the art (for example, the same as the definition of R2) may be substituted.

[0031] Ar2 introduced into the nitrogen-containing heterocycle (X-containing ring) is a C1-C 40 Alkyl groups, C2-C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C3-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphanyl groups, C6-C 60 Monoarylphosphinyl groups, C6-C 60 Diarylphosphinyl groups, C6-C 60 Arylamine groups, C5-C 60and heteroarylamine groups having 5 to 60 ring atoms. Specifically, Ar2 is selected from the group consisting of C6 to C 60 and heteroaryl groups having 5 to 60 ring atoms, more specifically, each independently selected from the group consisting of C6 to C 18 and heteroaryl groups having 5 to 18 ring atoms.

[0032] A specific example of Ar2 is the following structural formula: [ka] In the above formula, * indicates the binding site to Chemical Formula 1 above.

[0033] The nitrogen-containing heterocycle (e.g., X-containing ring) according to the present invention is linked to a number of aryl groups (R1) via a direct bond (n=0) or a separate linker (e.g., L). In this way, when a linker (L) is present between a number of aryl group sites and the nitrogen-containing aromatic ring, the HOMO region is expanded to provide a gain in the distribution of HOMO-LUMO, and the charge transfer efficiency can be improved by the appropriate overlap of HOMO-LUMO.

[0034] The linker (e.g., L) is not particularly limited and may be a common divalent group linker well known in the art. Specifically, L is a single bond or a C6-C 18 and heteroarylene groups having 5 to 18 ring atoms. More specifically, each independently may be selected from the group consisting of C6 to C 12 and heteroarylene groups having 5 to 12 ring atoms.

[0035] n is an integer of 0 to 3. When n is 0, L is a single bond, and when n is 1 or 2, there can be a plurality of Ls, which may be the same or different.

[0036] Specific examples of the arylene group linker include phenylene group, biphenylene group, naphthylene group, anthracenylene group, indenylene group, pyranthrene group, carbazolylene group, thiophenylene group, indolylene group, purinylene group, quinolinylene group, pyrrolylene group, imidazolylene group, oxazolylene group, thiazolylene group, pyridinylene group, pyrimidinylene group, etc. More specifically, phenylene group or biphenylene group is preferable. Specific examples of the heteroarylene group linker include dibenzofuran-based moiety, dibenzothiophene-based moiety, and / or dibenzoselenophenone-based moiety, etc.

[0037] The compounds of formula 1 according to the present invention may contain multiple aryl / heteroaryl groups (eg, R1-containing rings) on one side of the nitrogen-containing heterocycle (eg, X-containing ring).

[0038] Specifically, R1 is C6 to C 60 and heteroaryl groups having 5 to 60 nuclear atoms. The number (m) of aryl groups / heteroaryl groups to be introduced is an integer of 1 or more, and preferably 1 to 5. In this case, when m is 2 to 5, multiple R1s may be the same or different from each other.

[0039] In one embodiment, R1 is C6-C 12 wherein m is an integer of 1 to 5, and R1, which may or may not be substituted with a substituent described below, contains at least 18 carbon atoms.

[0040] In the above Chemical Formula 1, the arylene group and heteroarylene group of L, the aryl group and heteroaryl group of R1, and the R2 and R 11 ~R 12and 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, arylphosphanyl group, monoarylphosphinyl group, diarylphosphinyl group, arylamine group, arylheteroarylamine group, and heteroarylamine group of Ar2 each independently represent deuterium (D), halogen, cyano group, nitro group, C1 to C6 40 Alkyl groups, C2-C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide group, C6-C 60 Arylamine groups, C5-C 60 and heteroarylamine groups having 5 to 60 ring atoms, and in this case, when there are a plurality of the above-mentioned substituents, they may be the same or different.

[0041] In one embodiment of the present invention, the compound represented by the above Formula 1 may be embodied as any one of the following Formulas 3 to 9 depending on the type of a linker (L) and a ring compound having an unshared electron pair, specifically, a dibenzo-based / carbazole-based moiety (e.g., Ar1), but is not limited thereto. [ka] [ka] [ka] [ka] [ka] [ka] [ka] In the above formula, X, Y, Ar2, R1, n, and m are each as defined in claim 1; Circle D is a monocyclic or polycyclic hydrocarbon ring group with or without heteroatoms.

[0042] In another embodiment of the present invention, the compound represented by the above formula 1 may be embodied as any one of the following formulas 10 to 21 depending on the number of aryl groups (R1) introduced into the molecule and their binding positions, but is not limited thereto. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] In the above formula, X, Ar1, Ar2, L, R1, and n are each as defined in claim 1.

[0043] The compound represented by the above-mentioned Chemical Formula 1 of the present invention can be embodied as the following compounds, for example, compounds represented by 1 to 93, but is not limited thereto. [ka] [ka] [ka] [ka] [ka] [ka]

[0044] In the present invention, "alkyl" refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

[0045] In the present invention, "alkenyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon double bonds. Examples of this include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, etc.

[0046] In the present invention, "alkynyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon triple bonds. Examples of this include, but are not limited to, ethynyl, 2-propynyl, etc.

[0047] 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. The two or more rings may be in a pendant or condensed form. Examples of such groups include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0048] In the present invention, "heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. In addition, two or more rings may be in a pendant or condensed form, and further in a condensed form with an aryl group. Examples of this include 6-membered monocyclic rings such as pyridinyl, 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, but are not limited thereto.

[0049] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples of this include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, etc.

[0050] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' means an alkyl group having 1 to 40 carbon atoms, which may be linear, branched, or cyclic. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0051] In the present invention, the term "arylamine" refers to an amine substituted with an aryl having 6 to 40 carbon atoms.

[0052] 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, adamantine, and the like.

[0053] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 ring atoms, in which one or more carbons, preferably 1 to 3 carbons, in the ring are substituted with a heteroatom such as N, O, S, or Se. Examples include, but are not limited to, morpholine, piperazine, etc.

[0054] In the present invention, the term "alkylsilyl" refers to a silyl substituted with an alkyl having 1 to 40 carbon atoms, and the term "arylsilyl" refers to a silyl substituted with an aryl having 5 to 40 carbon atoms.

[0055] In the present invention, the term "fused ring" refers to a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

[0056] <Electron transport layer material> The present invention provides an electron transport layer comprising a compound represented by Chemical Formula 1 above.

[0057] The electron transport layer (ETL) serves to transport electrons injected from the cathode to an adjacent layer, specifically, the light-emitting layer.

[0058] The compound represented by the above formula 1 may be used alone or in combination with other electron transport layer materials known in the art as an electron transport layer (ETL) material, but is preferably used alone.

[0059] Electron transport layer materials that can be mixed with the compound of Formula 1 include electron transport materials known in the art. Examples of usable electron transport materials include, but are not limited to, 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)-aluminium), BAlq, SAlq, Almq3, gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), and the like. These may be used alone or in combination of two or more.

[0060] In the present invention, when the compound of the above Chemical Formula 1 is used in combination with an electron transport layer material, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0061] <Electron transport auxiliary layer material> The present invention also provides an electron transporting auxiliary layer comprising the compound represented by Chemical Formula 1 above.

[0062] The 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 to the electron transport layer.

[0063] The compound represented by the above Chemical Formula 1 may be used alone as the electron transport auxiliary layer material or may be used in combination with an electron transport layer material well known in the art, but is preferably used alone.

[0064] The electron transporting auxiliary layer material that can be mixed with the compound of Formula 1 includes electron transporting materials known in the art, such as oxadiazole derivatives, triazole derivatives, pentane derivatives (e.g., BCP), and nitrogen-containing heterocyclic derivatives.

[0065] In the present invention, when the compound of the above Chemical Formula 1 and the electron transport auxiliary layer material are used in combination, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0066] <Organic electroluminescence element> In another aspect, the present invention relates to an organic electroluminescence (organic EL device) containing the compound represented by Chemical Formula 1 according to the present invention as described above.

[0067] Specifically, the present invention relates to an organic electroluminescence device including an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, at least one of the one or more organic layers including the compound represented by Chemical Formula 1. In this case, the compound may be used alone or in combination of two or more kinds.

[0068] The one or more organic layers are any one or more of a hole injection layer, a hole transport layer, an emitting layer, an emitting auxiliary layer, a life improving layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of these organic layers contains a compound represented by Chemical Formula 1. Specifically, the organic layer containing the compound of Chemical Formula 1 is preferably a emitting layer (more specifically, a phosphorescent host material), an electron transport layer, or an electron transport auxiliary layer.

[0069] The light-emitting layer of the organic electroluminescence device according to the present invention contains a host material and a dopant material, and in this case, the host material may contain the compound of the above Chemical Formula 1. In addition to the compound of the above Chemical Formula 1, the light-emitting layer of the present invention may also contain a compound well known in the art as a host.

[0070] When the compound represented by the above Chemical Formula 1 is contained as an emission layer material of an organic electroluminescence device, preferably as a blue, green or red phosphorescent host material, the binding strength between holes and electrons in the emission layer is increased, so that the efficiency (light emitting efficiency and power efficiency), life, brightness, driving voltage, etc. of the organic electroluminescence device can be improved. Specifically, the compound represented by the above Chemical Formula 1 is preferably contained in the organic electroluminescence 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 an exciplex N-type host material for green phosphorescence in the emission layer having high efficiency.

[0071] The structure of the organic electroluminescence device of the present invention is not particularly limited, and may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are laminated in this order. In this case, one or more of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer, and the electron injection layer may contain a compound represented by Chemical Formula 1, and preferably, the light emitting layer, and more preferably, the phosphorescent host may contain a compound represented by Chemical Formula 1. In addition, an electron injection layer may be further laminated on the electron transport layer.

[0072] The organic electroluminescence element of the present invention may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0073] The organic electroluminescence device of the present invention can be manufactured by forming the organic layers and electrodes using materials and methods well known in the art, except that at least one of the above-mentioned organic layers contains the compound represented by Chemical Formula 1 above.

[0074] The organic layer can be formed by a vacuum deposition method or a solution coating method, such as, but not limited to, spin coating, deep coating, doctor blading, inkjet printing, or thermal transfer.

[0075] The substrate that can be used in the manufacture of the organic electroluminescence device of the present invention is not particularly limited, and examples thereof include, but are not limited to, silicon wafers, quartz, glass plates, metal plates, plastic films, and sheets.

[0076] The anode material may be any anode material known in the art, without limitation, including, but 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 polythiopene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiopene] (PEDT), polypyrrole, and polyaniline, and carbon black.

[0077] The cathode material may be any cathode material known in the art, without limitation, including, but 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.

[0078] The hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer are not particularly limited, and materials well known in the art can be used. EXAMPLES

[0079] The present invention will be described in detail below with reference to examples. However, the examples described below are merely illustrative of the present invention, and the present invention is not limited to these examples.

[0080] [Preparation Example 1] <Step 1> Synthesis of 3'-chloro-5'-phenyl-1,1':2',1''-terphenyl [ka] 100g (290.9mmol) of 2'-bromo-6'-chloro-1,1':4',1''-terphenyl, 37.3g (305.5mmol) of phenylboronic acid, 10.1g (8.7mmol) of Pd(PPh3)4, and 120.6g (872.98mmol) of K2CO3 were added to 970ml of THF and 240ml of H2O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added, water was removed, and the mixture was filtered. After filtration, the organic layer solvent was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 75.6g (76.3% yield) of 3'-chloro-5'-phenyl-1,1':2',1''-terphenyl. Mass: [(M+H) + ]:341

[0081] <Step 2> Synthesis of Core1 [ka] 75.6g (221.7mmol) of 3'-chloro-5'-phenyl-1,1':2',1''-terphenyl, 73.2g (288.3mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 36.1g (6.7mmol) of Pd2(dba), 65.3g (665.4mmol) of KOAc, and 6.3g (13.3mmol) of Xphos were added to 750ml of 1,4-dioxane and heated under reflux for 12 hours. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added, water was removed, and then filtration was performed. After filtration, the solvent in the organic layer was concentrated under reduced pressure, and the mixture was purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 72.7 g of Core 1 (yield 75.8%). Mass: [(M+H) + ]:433

[0082] [Preparation Example 2] Step 1: Synthesis of 5'-chloro-1,1':3',1'':3'',1'''-quaterphenyl [ka] 70 g (261.6 mmol) of 3-bromo-5-chloro-1,1'-biphenyl, 54.4 g (274.7 mmol) of [1,1'-biphenyl]-3-ylboronic acid, 49.1 g (7.8 mmol) of Pd(PPh3), and 108.5 g (784.9 mmol) of K2CO3 were placed in 870 ml of THF and 220 ml of H2O, and 74.1 g (yield 83.1%) of 5'-chloro-1,1':3',1'':3'',1'''-quaterphenyl was obtained in the same manner as in <Step 1> of [Preparation Example 1]. Mass: [(M+H) + ]:341

[0083] <Step 2> Synthesis of Core2 [ka] 74.1g (221.7mmol) of 5'-chloro-1,1':3',1'':3'',1'''-quaterphenyl, 71.8g (282.6mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 36.0g (6.5mmol) of Pd2(dba), 64.0g (652.2mmol) of KOAc, and 6.2g (13.0mmol) of Xphos were added to 750ml of 1,4-dioxane, and 77.2g (77.1% yield) of Core2 was obtained in the same manner as in the synthesis of Core1 in [Preparation Example 1]. Mass: [(M+H) + ]:433

[0084] [Preparation Example 3] <Step 1> Synthesis of 5'-chloro-3'-phenyl-1,1':2',1''-terphenyl [ka] 70 g (261.6 mmol) of 2'-bromo-5'-chloro-1,1':3',1''-terphenyl, 54.4 g (274.7 mmol) of phenylboronic acid, 49.1 g (7.8 mmol) of Pd(PPh3), and 108.5 g (784.9 mmol) of K2CO3 were placed in 870 ml of THF and 220 ml of H2O, and 47.5 g (yield 68.4%) of 5'-chloro-3'-phenyl-1,1':2',1''-terphenyl was obtained in the same manner as in <Step 1> of [Preparation Example 1]. Mass: [(M+H) + ]:341

[0085] <Step 2> Synthesis of Core3 [ka] 47.5g (139.3mmol) of 5'-chloro-3'-phenyl-1,1':2',1''-terphenyl, 45.9g (181.1mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 33.8g (4.2mmol) of Pd2(dba), 41.0g (417.9mmol) of KOAc, and 4.0g (8.3mmol) of Xphos were added to 470ml of 1,4-dioxane, and 45.25g (75.1% yield) of Core3 was obtained in the same manner as in the synthesis of Core1 in [Preparation Example 1]. Mass: [(M+H) + ]:433

[0086] [Preparation Example 4] Step 1: Synthesis of 5''-chloro-1,1':3',1'':3'',1''':4'''',1''''-quinquiphenyl [ka] 50 g (145.5 mmol) of 3-bromo-5-chloro-1,1':4',1''-terphenyl, 30.2 g (152.8 mmol) of [1,1'-biphenyl]-3-ylboronic acid, 45.0 g (4.4 mmol) of Pd(PPh3), and 60.3 g (436.5 mmol) of K2CO3 were placed in 490 ml of THF and 125 ml of H2O, and 53.9 g (yield 88.9%) of 5''-chloro-1,1':3',1'':3'',1''':4''',1''''-quinquiphenyl was obtained in the same manner as in <Step 1> of [Preparation Example 1]. Mass: [(M+H) + ]:417

[0087] <Step 2> Synthesis of Core4 [ka] 53.9g (129.3mmol) of 5''-chloro-1,1':3',1'':3'',1''':4''',1''''-quinquiphenyl, 45.9g (181.1mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 33.6g (3.9mmol) of Pd2(dba), 38.1g (388.0mmol) of KOAc, and 3.7g (7.8mmol) of Xphos were placed in 430ml of 1,4-dioxane, and 41.96g (yield 63.8%) of Core 4 was obtained in the same manner as in the synthesis of Core 1 in [Preparation Example 1]. Mass: [(M+H) + ]:508

[0088] [Preparation Example 5] <Step 1> Synthesis of 2-(5'-chloro-[1,1':3',1''-terphenyl]-4-yl)naphthalene [ka] 50g (186.9mmol) of 3-bromo-5-chloro-1,1'-biphenyl, 48.9g (196.2mmol) of (4-naphthalene-2-yl)phenyl)boronic acid, 46.5g (5.6mmol) of Pd(PPh3), and 77.5g (560.6mmol) of K2CO3 were placed in 625ml of THF and 155ml of H2O, and 55.9g (yield 76.6%) of 2-(5'-chloro-[1,1':3',1''-terphenyl]-4-yl)naphthalene was obtained in the same manner as in <Step 1> of [Preparation Example 1]. Mass: [(M+H) + ]:391

[0089] <Step 2> Synthesis of Core5 [ka] 55.9g (143.1mmol) of 2-(5'-chloro-[1,1':3',1''-terphenyl]-4-yl)naphthalene, 47.2g (186.1mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 33.9g (4.3mmol) of Pd2(dba), 42.1g (429.4mmol) of KOAc, and 4.1g (8.6mmol) of Xphos were added to 480ml of 1,4-dioxane, and 40.26g (yield 58.3%) of Core5 was obtained in the same manner as in the synthesis of Core1 in [Preparation Example 1]. Mass: [(M+H) + ]:483

[0090] [Preparation Example 6] <Step 1> Synthesis of 3-(5-chloro-[1,1'-biphenyl]-3-yl)dibenzo[b,d]furan [ka] 50 g (186.9 mmol) of 3-bromo-5-chloro-1,1'-biphenyl, 41.6 g (196.2 mmol) of dibenzo[b,d]furan-3-ylboronic acid, 46.5 g (5.6 mmol) of Pd(PPh3), and 77.5 g (560.6 mmol) of K2CO3 were placed in 625 ml of THF and 155 ml of H2O, and 56.4 g (yield 85.1%) of 3-(5-chloro-[1,1'-biphenyl]-3-yl)dibenzo[b,d]furan was obtained in the same manner as in <Step 1> of [Preparation Example 1]. Mass: [(M+H) + ]:355

[0091] <Step 2> Synthesis of Core6 [ka] 56.4g (159.0mmol) of 3-(5-chloro-[1,1''-biphenyl]-3-yl)dibenzo[b,d]furan, 52.5g (206.7mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 34.4g (4.7mmol) of Pd2(dba), 46.8g (477.1mmol) of KOAc, and 4.5g (9.5mmol) of Xphos were added to 530ml of 1,4-dioxane, and 56.7g (79.9% yield) of Core6 was obtained in the same manner as in the synthesis of Core1 in [Preparation Example 1]. Mass: [(M+H) + ]:447

[0092] [Synthesis Example 1] Synthesis of Compound 1 [ka] 15.0g (leq, 29.4mmol) of 2-(4-chlorophenyl)-4-phenyl-6-(1-phenyldibenzo[b,d]furan-3-yl)-1,3,5-triazine, 13.4g (1.05eq, 30.9mmol) of Core1 from [Preparation Example 1], 0.2g (0.03eq, 0.9mmol) of Pd(OAc)2, 28.7g (3.0eq, 88.2mmol) of Cs2CO3, and 0.8g (0.06eq, 1.8mmol) of Xphos were added to 100ml of toluene, 25ml of EtOH, and 25ml of H2O, and the mixture was heated and refluxed for 12 hours to react. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added, and filtration was performed. After removing the solvent from the filtered organic layer, the residue was subjected to column chromatography using dichloromethane and hexane, and then recrystallized from toluene and acetone to obtain 15.8 g of compound 1 (yield 68.8%). Mass: [(M+H) + ]:780

[0093] [Synthesis Example 2] Synthesis of Compound 3 [ka] Compound 3 (12.7 g, yield 55.2%) was obtained by the same process and equivalent ratio as in [Synthesis Example 1], except that 15.0 g (29.5 mmol) of 4-(3-chlorophenyl)-2-phenyl-6-(1-phenyldibenzo[b,d]furan-4-yl)pyrimidine was used instead of 2-(4-chlorophenyl)-4-phenyl-6-(phenyldibenzo[b,d]furan-3-yl)-1,3,5-triazine. Mass: [(M+H) + ]:779

[0094] [Synthesis Example 3] Synthesis of Compound 11 [ka] Compound 11 (19.0 g, 81.4% yield) was obtained by the same process and equivalent ratio as in [Synthesis Example 1], except that 15.0 g (30.9 mmol) of 2-(4-chlorophenyl)-4-(naphtho[2,1-b]benzofuran-9-yl)-6-phenyl-1,3,5-triazine was used instead of 2-(4-chlorophenyl)-4-phenyl-6-(phenyldibenzo[b,d]furan-3-yl)-1,3,5-triazine. Mass: [(M+H) + ]:754

[0095] [Synthesis Example 4] Synthesis of Compound 16 [ka] 10.0g (leq, 16.6mmol) of 4'-(4-(benzo[b]naphtho[2,1-d]thiophen-9-yl)-6-(3-chlorophenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-carbonitrile, 4.78g (1.05eq, 17.4mmol) of [1,1':3',1''-terphenyl]-5'-ylboronic acid, 0.1g (0.03eq, 0.5mmol) of Pd(OAc)2, 16.26g (3.0eq, 49.9mmol) of Cs2CO3, 0.5g (0.06eq, 1.0mmol) of Xphos were added to 130ml of toluene, 30ml of EtOH, and 30ml of H2O, and the mixture was heated under reflux for 8 hours to react. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and the mixture was recrystallized with toluene and acetone to obtain 5.7 g of compound 16 (yield 42.8%). Mass: [(M+H) + ]:795

[0096] [Synthesis Example 5] Synthesis of Compound 17 [ka] 15.0g (leq, 23.6mmol) of 2-(4-(4-chlorophenyl)-6-phenyl-1,3,5-triazin-2-yl)-4-(naphthalen-2-yl)-9-phenyl-9H-carbazole, 10.7g (1.05eq, 24.8mmol) of Core2 from [Preparation Example 2], 0.16g (0.03eq, 0.7mmol) of Pd(OAc)2, 3.1g (3.0eq, 70.8mmol) of Cs2CO3, and 0.67g (0.06eq, 1.4mmol) of Xphos were added to 100ml of toluene, 25ml of EtOH, and 25ml of H2O, and the mixture was heated and refluxed for 8 hours to react. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the residue was subjected to column chromatography using dichloromethane and hexane, and then recrystallized from toluene and acetone to obtain 10.9 g of compound 17 (yield 51.2%). Mass: [(M+H) +]:906

[0097] [Synthesis Example 6] Synthesis of Compound 28 [ka] 15.0g (leq, 26.08mmol) of 4-(benzo[b]naphtho[1,2-d]thiophen-6-yl)-6-(5-chloro-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine, 11.8g (1.05eq, 27.39mmol) of Core3 from [Preparation Example 3], 0.18g (0.03eq, 0.8mmol) of Pd(OAc)2, 25.5g (3.0eq, 78.2mmol) of Cs2CO3, and 0.74g (0.06eq, 1.6mmol) of Xphos were added to 100ml of toluene, 30ml of EtOH, and 30ml of H2O, and the mixture was heated and refluxed for 8 hours to react. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the residue was subjected to column chromatography using dichloromethane and hexane, and then recrystallized from toluene and acetone to obtain 15.7 g of compound 28 (yield 71.1%). Mass: [(M+H) + ]:845

[0098] [Synthesis Example 7] Synthesis of Compound 37 [ka] Compound 37 (17.8 g, 76.5% yield) was obtained by the same process and equivalent ratio as in [Synthesis Example 1], except that 15.0 g (30.9 mmol) of 2-(4-chlorophenyl)-4-(naphtho[2,1-b]benzofuran-9-yl)-6-phenyl-1,3,5-triazine was used instead of 2-(4-chlorophenyl)-4-phenyl-6-(1-phenyldibenzo[b,d]furan-3-yl)-1,3,5-triazine. Mass: [(M+H) + ]:754

[0099] [Synthesis Example 8] Synthesis of Compound 49 [ka] 2-([1,1'-biphenyl]-4-yl)-4-(6-chloro-[1,1'-biphenyl]-3-yl)-6-(naphtho[2,1-b]benzofuran-5-yl)pyrimidine 13.0g (leq, 20.5mmol), [1,1':3',1''-terphenyl]-5'-ylboronic acid 5.9g (1.05eq, 21.5mmol), Pd(OAc) 20.14g (0.03eq, 0.6mmol), Cs2CO3 20.0g (3.0eq, 61.4mmol), Xphos 0.6g (0.06eq, 1.2mmol) were added to toluene 130ml, EtOH 30ml, and H2O 30ml, and the mixture was heated under reflux for 10 hours to cause a reaction. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and the mixture was recrystallized with toluene and acetone to obtain 8.3 g of compound 49 (yield 48.9%). Mass: [(M+H) + ]:830

[0100] [Synthesis Example 9] Synthesis of Compound 50 [ka] Compound 50 (11.1 g, 53.4% ​​yield) was obtained by the same process and equivalent ratio as in [Synthesis Example 1], except that 14.0 g (25.1 mmol) of 3-(4-(3-chlorophenyl)-6-phenylpyrimidin-2-yl)-5-phenyl-5H-benzo[b]carbazole was used instead of 2-(4-chlorophenyl)-4-phenyl-6-(1-phenyldibenzo[b,d]furan-3-yl)-1,3,5-triazine. Mass: [(M+H) + ]:829

[0101] [Synthesis Example 10] Synthesis of Compound 58 [ka] Instead of 2-([1,1'-biphenyl]-4-yl)-4-(6-chloro-[1,1'-biphenyl]-3-yl)-6-(naphtho[2,1-b]benzofuran-5-yl)pyrimidine, 14.0 g (25.1 mmol) of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-(2-phenyldibenzo[b,d]thiophen-4-yl)-1,3,5-triazine was used, and 12.4 g (yield 62.5%) of compound 58 was obtained by the same process and equivalent ratio as in [Synthesis Example 8]. Mass: [(M+H) + ]:797

[0102] [Synthesis Example 11] Synthesis of Compound 72 [ka] Instead of 2-([1,1'-biphenyl]-4-yl)-4-(6-chloro-[1,1'-biphenyl]-3-yl)-6-(naphtho[2,1-b]benzofuran-5-yl)pyrimidine, 14.0 g (25.1 mmol) of 2-(4-chlorophenyl)-4-(7,8-diphenyldibenzo[b,d]furan-2-yl)-6-phenylpyrimidine was used, and 14.4 g (72.1% yield) of compound 72 was obtained by the same process and equivalent ratio as in [Synthesis Example 8]. Mass: [(M+H) + ]:799

[0103] [Synthesis Example 12] Synthesis of Compound 80 [ka] 12.0g (leq, 21.5mmol) of 2-(4-chlorophenyl)-4-(7-(naphthalene-2-yl)dibenzo[b,d]furan-2-yl)-6-phenylpyrimidine, 9.7g (1.05eq, 22.5mmol) of Core4 from [Preparation Example 4], 0.14g (0.03eq, 0.6mmol) of Pd(OAc)2, 1.0g (3.0eq, 64.4mmol) of Cs2CO3, and 0.61g (0.06eq, 1.3mmol) of Xphos were added to 140ml of toluene, 35ml of EtOH, and 35ml of H2O, and the mixture was heated and refluxed for 8 hours to react. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the residue was subjected to column chromatography using dichloromethane and hexane, and then recrystallized from toluene and acetone to obtain 10.1 g of compound 80 (yield 51.8%). Mass: [(M+H) + ]:906

[0104] [Synthesis Example 13] Synthesis of Compound 81 [ka] Instead of 4-(benzo[b]-naphtho[1,2-d]thiophen-6-yl)-6-(5-chloro-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine, 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, and 19.2 g (yield 82.2%) of compound 81 was obtained by the same process and equivalent ratio as in [Synthesis Example 6]. Mass: [(M+H) + ]:755

[0105] [Synthesis Example 14] Synthesis of Compound 82 [ka] 2-(3-chlorophenyl)-4-phenyl-6-(1-phenyldibenzo[b,d]thiophen-4-yl)-1,3,5-triazine 13.0g (leq, 24.7mmol), Core5 12.5g (1.05eq, 25.9mmol) of [Preparation Example 5], Pd(OAc)20.17g (0.03eq, 0.67mmol), Cs2CO324.1g (3.0eq, 74.1mmol), Xphos0.7g (0.06eq, 1.5mmol) were added to toluene 150ml, EtOH40ml, and H2O40ml, and the mixture was heated and refluxed for 8 hours to react. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added, and filtration was performed. After removing the solvent from the filtered organic layer, the residue was subjected to column chromatography using dichloromethane and hexane, and then recrystallized from toluene and acetone to obtain 13.2 g of compound 82 (yield 63.3%). Mass: [(M+H) + ]:847

[0106] [Synthesis Example 15] Synthesis of Compound 83 [ka] 15.0g (leq, 31.1mmol) of 4-(4-chlorophenyl)-6-(naphtho[2,1-b]benzofuran-9-yl)-2-phenylpyrimidine, 14.6g (1.05eq, 25.9mmol) of Core6 from [Preparation Example 6], 0.21g (0.03eq, 0.93mmol) of Pd(OAc)2, 0.4g (3.0eq, 93.2mmol) of Cs2CO3, and 0.9g (0.06eq, 1.9mmol) of Xphos were added to 150ml of toluene, 40ml of EtOH, and 40ml of H2O, and the mixture was heated and refluxed for 10 hours to react. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the residue was subjected to column chromatography using dichloromethane and hexane, and then recrystallized from toluene and acetone to obtain 19.5 g of compound 83 (yield 81.9%). Mass: [(M+H) + ]:768

[0107] [Examples 1 to 10] Preparation of blue organic electroluminescence element Compounds 1 to 93 were purified to high purity by sublimation in a conventional manner, and then blue organic electroluminescence devices were fabricated as follows. First, a glass substrate coated with a thin film of ITO (Indium Tin Oxide) with a thickness of 1500 Å was ultrasonically cleaned with distilled water. After cleaning with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, and the substrate was then dried and transferred to a UV ozone cleaner (Power sonic 405, manufactured by Fashintech Co., Ltd.) where it was cleaned with UV for 5 minutes and then transferred to a vacuum deposition machine. On the transparent electrode of ITO prepared as described above, 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 1 to 87: LiQ=1:1 (300 Å) / LiF (10 Å) / Al (1000 Å) were laminated in this order to prepare an organic electroluminescence element.

[0108] The structures of HT-1, HAT-CN, HT-2, BH, BD, ET-1, ET-2, and LiQ used at this time are as follows: [ka] [ka] [ka]

[0109] [Comparative Example 1] Preparation of a blue organic electroluminescence element A blue organic electroluminescence device was produced in the same manner as in Example 1, except that ET-1 was deposited to a thickness of 300 Å instead of Compounds 1 to 87 used as the electron transport layer material.

[0110] [Evaluation example 1] For the blue organic electroluminescence devices produced in Examples 1 to 10 and Comparative Example 1, a current density of 10 mA / cm 2 The driving voltage, current efficiency, and emission peak were measured at 1000 V, and the results are shown in Table 1 below.

[0111] [Table 1]

[0112] As shown in Table 1 above, the blue organic electroluminescence elements of Examples 1 to 10 in which the compounds according to the present invention were used as electron transport layer materials exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescence element of Comparative Example 1 in which conventional ET-1 was used in the electron transport layer.

[0113] [Examples 11 to 33] Preparation of blue organic electroluminescence elements Compounds 1 to 93 were purified to high purity by sublimation in a conventional manner, and then blue organic electroluminescence devices were fabricated as follows. A glass substrate coated with a thin film of ITO (Indium Tin Oxide) with a thickness of 1500 Å was ultrasonically cleaned with distilled water. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV ozone cleaner (Power sonic 405, manufactured by Fashintech Co., Ltd.) and cleaned with UV for 5 minutes before being transferred to a vacuum deposition machine. On the ITO transparent electrode prepared as described above, HT-1+2% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / BH+2% BD (200 Å) / compounds 1-93 (50 Å) / ET-1:LiQ=1:1 (300 Å) / LiF (10 Å) / Al (1000 Å) were laminated in this order to prepare an organic electroluminescence element. The structures of HT-1, HAT-CN, HT-2, BH, BD, ET-1, ET-2, and LiQ used here are as described above in [Examples 1 to 10].

[0114] [Comparative Examples 2 to 5] Preparation of blue organic electroluminescence elements A blue organic electroluminescence element was prepared in the same manner as in Example 11, except that compounds 1 to 93 used as the electron transport auxiliary layer materials in Example 11 were not used, and electron transport auxiliary layer materials ET-2 to ET-6 were deposited to a thickness of 50 Å. The structures of ET-2 to ET-6 used at this time are as follows: [ka]

[0115] [Evaluation example 2] For the blue organic electroluminescence devices produced in Examples 11 to 33 and Comparative Example 2, a current density of 10 mA / cm 2 The driving voltage, current efficiency, and emission peak were measured at 1000 V, and the results are shown in Table 2 below.

[0116] [Table 2]

[0117] As shown in Table 2 above, the blue organic electroluminescence elements of Examples 11 to 33, which contain the compounds according to the present invention as electron transport auxiliary layer materials, exhibited superior performance in terms of current efficiency and driving voltage compared to the organic electroluminescence elements of Comparative Examples 2 to 6, which contain compounds having a different number of carbon atoms contained in the dibenzo-based moiety from that of the present invention.

Claims

1. A compound represented by the following chemical formula 1: 【Chemistry 1】 (In chemical formula 1, A plurality of X may be the same or different, and each independently represents CR ２ or N, with the proviso that at least two of the plurality of X's are N; R ２ is hydrogen, deuterium (D), halogen, cyano group, nitro group, C １ ~C ４０ Alkyl groups of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; a heterocycloalkyl group having 3 to 40 ring atoms; ６ ~C ６０ an aryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C ３ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ６０ an arylboron group of C ６ ~C ６０ an arylphosphanyl group of C ６ ~C ６０ a monoarylphosphinyl group of C ６ ~C ６０ a diarylphosphinyl group of C ６ ~C ６０ an arylamine group of C ５ ~C ６０ and heteroarylamine groups having 5 to 60 ring atoms; L is a single bond or C ６ ~C １８ and heteroarylene groups having 5 to 18 ring atoms, R １ is C ６ ~C ６０ and heteroaryl groups having 5 to 60 ring atoms, m is an integer of 1 or more, and n is an integer of 0 to 3, Ar ２ is C １ ~C ４０ Alkyl groups of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; a heterocycloalkyl group having 3 to 40 ring atoms; ６ ~C ６０ an aryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C ３ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ６０ an arylboron group of C ６ ~C ６０ an arylphosphanyl group of C ６ ~C ６０ a monoarylphosphinyl group of C ６ ~C ６０ a diarylphosphinyl group of C ６ ~C ６０ an arylamine group of C ５ ~C ６０ and heteroarylamine groups having 5 to 60 ring atoms; Ar １ is a moiety represented by the following chemical formula 2: 【Chemistry 2】 (In chemical formula 2, * is a binding site to Chemical Formula 1, Y is O, S, or NR １１ and Circle A and circle B may be the same or different, and each independently represents a C ５ ~C １８ is a monocyclic or polycyclic hydrocarbon ring group of the formula R １１ and R １２ may be the same or different, and each independently represents １ ~C １２ Alkyl groups of C ６ ~C １２ or a heteroaryl group having 5 to 12 ring atoms, which may be bonded to an adjacent group to form a condensed ring, a is 0 to 2; The arylene group and heteroarylene group of L, the R １ The aryl and heteroaryl groups of the above R ２ , R １１ ~R １２ , and Ar ２ 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, arylphosphanyl group, monoarylphosphinyl group, diarylphosphinyl group, arylamine group, arylheteroarylamine group, and heteroarylamine group each independently represent a deuterium (D), a halogen, a cyano group, a nitro group, a C １ ~C ４０ Alkyl groups of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; a heterocycloalkyl group having 3 to 40 ring atoms; ６ ~C ６０ an aryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ６０ an arylboron group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of C ６ ~C ６０ an arylamine group of C ５ ~C ６０ and heteroarylamine groups having 5 to 60 ring atoms. In this case, when there are a plurality of the above-mentioned substituents, they may be the same or different from each other. However, Ar １ The total number of carbon atoms contained in the alkyl group is 16 to 24.

2. The above Ar １ is selected from the group of substituents represented by the following chemical formula: 【Chemistry 3】 In the above chemical formula, * is a binding site to Chemical Formula 1 above, Circles D may be the same or different and each independently represents a monocyclic or polycyclic hydrocarbon ring group which may or may not contain a heteroatom; Y and R １２ are each as defined in claim 1.

3. The above Ar １ is selected from the group of substituents represented by the following chemical formula: 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 In the above chemical formula, R １１ and R １２ are each as defined in claim 1.

4. R １ is C ６ ~C １２ is an aryl group of the formula m is an integer from 1 to 5, R substituted or unsubstituted with a substituent １ The compound according to claim 1 , wherein the total number of carbon atoms contained in is at least 18.

5. The compound according to claim 1, wherein the X-containing ring is selected from the group consisting of substituents represented by the following chemical formulas: 【Chemistry 7】 In the above chemical formula, * is a binding site to Chemical Formula 1 above, R ２ , Ar １ , and Ar ２ are each as defined in claim 1.

6. Ar ２ is C ６ ~C ６０ and heteroaryl groups having 5 to 60 ring atoms.

7. The above Ar ２ The compound according to claim 1, wherein is selected from the group of substituents represented by the following chemical formula: 【Chemistry 8】

8. The compound represented by the above formula 1 is represented by any one of the following formulas 3 to 9. The compound according to claim 1: 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 In the above chemical formula, X, Y, Ar ２ , R １ , n, and m are each as defined in claim 1; Circle D is a monocyclic or polycyclic hydrocarbon ring group with or without heteroatoms.

9. The compound represented by the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 10 to 21. The compound according to claim 1: 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemical 27】 In the above chemical formula, X, Ar １ , Ar ２ , L, R １ , and n are each as defined in claim 1.

10. The compound according to claim 1, wherein the compound represented by the above formula 1 is represented by any one of the following formulas 1 to 93: 【Chemistry 28】 【Chemical 29】 【Chemistry 30】 【Chemistry 31】 【Chemistry 32】 【Chemical 33】

11. The compound according to claim 1 , wherein the compound represented by 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 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 the compound according to any one of claims 1 to 11.

13. The organic electroluminescence device according to claim 12, wherein the organic layer containing the 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 life improvement layer, an electron transport layer, and an electron transport auxiliary layer.

14. The organic electroluminescence device according to claim 13 , wherein the compound is contained as at least one material selected from the group consisting of a phosphorescent host material in an emitting layer, an electron transport layer, and an electron transport auxiliary layer.

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