Homogeneous organic composite for organic electroluminescent device and organic electroluminescent device comprising same

Abstract

The present invention relates to a homogeneous organic composite for an organic electroluminescent device and an organic electroluminescent device comprising the same, and more particularly, to a homogeneous organic composite having a homogeneous composition at a molecular level without thermal damage, and an organic electroluminescent device comprising the same, and to an organic electroluminescent device comprising the same. The organic electroluminescent element has low voltage, high efficiency, and improved long-life characteristics by including the homogeneous organic composite in the one or more organic material layers.

Description

Technical Field

[0001] The present invention relates to a homogeneous organic complex for an organic electroluminescent device and an organic electroluminescent device containing the same, and more particularly, to a homogeneous organic complex and an organic electroluminescent device, wherein the homogeneous organic complex has a homogeneous composition at a molecular level without thermal damage, and the organic electroluminescent device has low voltage, high efficiency and improved long life characteristics by containing the homogeneous organic complex in one or more organic layers. Background Art

[0002] For an organic electroluminescent device (hereinafter, 'organic EL device'), when a voltage is applied between two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground state, light is emitted. In this case, the organic substance used as the organic layer can be divided into a light-emitting substance, a hole injection substance, a hole transport substance, an electron transport substance, an electron injection substance, etc. according to its function.

[0003] In order to improve the performance of such organic electroluminescent devices, especially the lifespan, efficiency and driving voltage, an organic layer is formed by dispersing a plurality of organic compounds, for example, one or more host materials dispersed with dopants. The organic layer is formed by evaporating the plurality of organic compounds separately, in which case it is not only difficult to correctly control each organic compound at a desired deposition rate, but also wasteful in terms of material utilization. Moreover, static charge may be generated when the organic compound is solidified in powder form, so there is a problem of being difficult to handle during the deposition process.

[0004] On the other hand, a pre-mixing method of mixing a plurality of organic materials and using them as an organic layer or a pre-melting method of subjecting the organic materials to an additional heat treatment has been used in the past. However, not only is it impossible to obtain a desired level of homogeneous composition by the pre-mixing method, but also the organic materials are thermally damaged by the heat treatment during the pre-melting process, which inevitably leads to a reduction in the performance of the final device. Summary of the invention

[0005] Technical issues

[0006] The present invention is proposed to solve the above-mentioned problems. Its technical problem is to provide a new type of organic layer mixed material, which can ensure a more uniform mixed composition than the existing pre-mixing method, and can fundamentally prevent the thermal damage caused by the existing pre-melting method.

[0007] Furthermore, another technical problem of the present invention is to provide an organic electroluminescent device which simultaneously exhibits high efficiency, low voltage and long life by including the novel organic layer mixed material.

[0008] Other objects and advantages of the present invention will be more clearly described through the following detailed description of the invention and the scope of the claims.

[0009] Technical Solution

[0010] In order to solve the above technical problems, the present invention provides a homogeneous organic complex for an organic electroluminescent device, wherein the homogeneous organic complex is composed of at least two organic compounds, wherein the homogeneous organic complex comprises a first organic compound and a second organic compound, and the maximum emission wavelength of the homogeneous organic complex is different from the maximum emission wavelength of the first organic compound, the second organic compound, and a simple organic mixture of the first organic compound and the second organic compound.

[0011] In one embodiment of the present invention, the maximum emission wavelength of the homogeneous organic composite may be shifted to a longer wavelength region than the maximum emission wavelength of the first organic compound, the second organic compound, and a simple organic mixture of the first organic compound and the second organic compound.

[0012] In one embodiment of the present invention, the homogeneous organic composite may be solid at room temperature.

[0013] In one embodiment of the present invention, the homogeneous organic composite can be formed by completely dissolving the first organic compound and the second organic compound in at least one organic solvent to form a homogeneous phase and then solidifying the dissolved organic compound.

[0014] In one embodiment of the present invention, the homogeneous organic composite can be formed by press-molding the solidified homogeneous organic composite under non-heat treatment conditions.

[0015] In one embodiment of the present invention, the solidified homogeneous organic composite may be in the form of powder or rod, and the press-formed homogeneous organic composite may be in the form of pellets selected from the group consisting of polyhedron, cylinder and sphere.

[0016] In one embodiment of the present invention, the first organic compound and the second organic compound may be -6 The deposition temperature difference is 0°C to 30°C at a pressure of torr.

[0017] In one embodiment of the present invention, the mixing ratio of the first organic compound to the second organic compound may be 1:99 to 99:1 by weight.

[0018] In one embodiment of the present invention, the homogeneous organic composite may not contain inorganic substances and dopants.

[0019] In one embodiment of the present invention, the first organic compound and the second organic compound may be the same as or different from each other, and may be independently selected from the group consisting of a host material, an electron injection material, an electron transport material, an electron blocking material, a hole injection material, a hole transport material, a hole blocking material and an exciton blocking material.

[0020] In one embodiment of the present invention, the first organic compound and the second organic compound may be host materials.

[0021] In one embodiment of the present invention, the first organic compound may be a compound having higher hole injection / transport properties than the second organic compound, and the second organic compound may be a compound having higher electron injection / transport properties than the first organic compound.

[0022] Furthermore, the present invention provides an organic electroluminescent device, comprising: an anode; a cathode disposed opposite to the anode; and at least one organic layer disposed between the anode and the cathode, wherein the at least one organic layer comprises the homogeneous organic composite.

[0023] In one embodiment of the present invention, the at least one organic layer may be formed by depositing a homogeneous organic composite that is solid at room temperature.

[0024] Moreover, the present invention provides a method for preparing a homogeneous organic composite, which comprises: a first step of completely dissolving two or more vaporizable or sublimable organic compounds in at least one organic solvent to form a homogeneous phase and then solidifying the homogeneous phase; and a second step of pressurizing the solidified homogeneous organic composite under non-heat treatment conditions.

[0025] Effects of the Invention

[0026] According to an embodiment of the present invention, at least two organic compounds that can be vaporized and / or sublimated are used to form homogeneous organic complexes in a specified organic solvent, thereby ensuring a more uniform mixed composition than the existing pre-mixed preparation method.

[0027] Furthermore, in the present invention, a solid homogeneous organic composite having a desired size and shape can be easily formed without additional heat treatment, thereby fundamentally solving the thermal damage of the material caused by the existing pre-melting method.

[0028] In addition, in the present invention, an organic electroluminescent device having high efficiency and long life can be provided through the simplicity of a preparation process and simplification of a process, and thus a display panel having improved performance and life can be provided.

[0029] The effects of the present invention are not limited to the contents of the above-mentioned examples, and more various effects are included in this specification. DETAILED DESCRIPTION

[0030] Hereinafter, the present invention will be described in detail. The embodiments of the present invention are provided to fully describe the invention to those skilled in the art, and the following embodiments may be modified in various other forms, and the scope of the present invention is not limited to the following embodiments. In this case, the same reference numerals represent the same structural elements throughout this specification.

[0031] Unless otherwise defined, all terms (including technical and scientific terms) used in this specification may be used with the meanings commonly understood by those skilled in the art to which the present invention belongs. Also, unless explicitly defined otherwise, terms defined in commonly used dictionaries are not idealized or over-interpreted.

[0032] Furthermore, throughout the specification, unless otherwise specifically stated to the contrary, when a part "includes" a certain structural element, it means that other structural elements may also be included, rather than excluding other structural elements. Furthermore, throughout the specification, "above" or "upper" not only means including the case where it is located above or below the object part, but also includes the case where there are other parts in the middle, and does not mean that it must be located above the direction of gravity. Moreover, in the specification of the present invention, terms such as "first" and "second" are used to distinguish structural elements from each other without indicating any order or importance.

[0033] <Homogeneous organic complex>

[0034] In one example of the present invention, the homogeneous organic composite comprises at least two organic compounds forming an organic layer included in an organic electroluminescent device, and the homogeneous organic composite consists of at least two organic compounds that can be vaporized or sublimated.

[0035] Specifically, in the present invention, the solubility parameter characteristics between at least two organic compounds and a specified organic solvent are utilized to form a homogeneous organic complex having a homogeneous mixed composition at the molecular level without the need for pre-treatment such as additional heat treatment or mechanical mixing. Such a homogeneous organic complex not only has a more uniform mixed composition than the existing pre-mixed preparation method, but also does not fundamentally cause thermal damage to the organic material when the existing pre-melting method is used.

[0036] In particular, in the past, a complex was formed by reacting one or more organic compounds with additional reactants such as ionic bond compounds (e.g., Brüningster acid, halogen binding substances), proton-donating compounds and / or electron-donating compounds, etc., which are used to form chemical bonds (e.g., covalent bonds, ionic bonds, coordination bonds) with the above-mentioned compounds. In this case, in addition to the organic compounds in the organic electroluminescent device, other substances (e.g., inorganic or organic / inorganic) must also be included, so that the performance and stability of the organic electroluminescent device, etc., will be affected. Moreover, additional reactants and preparation processes for this purpose are required for forming chemical bonds, which leads to complication of the preparation method, rising process costs, and decreased productivity, etc. In contrast, in the present invention, without forming a chemical bond with the third compound, the solubility characteristics between at least two organic compounds and an organic solvent are used to form a micro-homogeneous composition at the molecular level, and then a homogeneous organic complex is formed by removing the organic solvent, so not only the final product does not contain substances that may have an adverse effect on the performance of the device, but also the process is simple, the cost is reduced, and mass production, etc. can be ensured at the same time.

[0037] Furthermore, a solid homogeneous organic complex having a desired size and shape can be freely formulated, and thus an organic electroluminescent device having high efficiency and long life can be provided through the simplicity of the preparation process and the simplification of the process.

[0038] The homogeneous organic complex of the present invention is an organic complex formed by at least two organic compounds having physical interactions, and thus has optical properties completely different from those of each single organic compound or a heterogeneous mixture thereof.

[0039] In one specific example, the homogeneous organic complexes are at least two organic compounds that can be vaporized or sublimated, including a first organic compound and a second organic compound, and the maximum emission wavelength of the homogeneous organic complex has physical properties different from the maximum emission wavelength of the first organic compound, the second organic compound, and a simple organic mixture of the first organic compound and the second organic compound. The simple organic mixture refers to a simple mixture in which each compound is mixed and does not form a complex.

[0040] Specifically, the homogeneous organic composite of the present invention forms a composite having more stable electrical energy than the first organic compound, the second organic compound, and a simple mixture thereof, so that the maximum emission wavelength caused by photons also moves to a relatively stable long wavelength region. Therefore, the maximum emission wavelength (λmax) of the above-mentioned homogeneous organic composite can be moved to a wavelength region longer than each maximum emission wavelength of the first organic compound, the second organic compound, and a heterogeneous organic mixture of the above-mentioned first organic compound and the above-mentioned second organic compound simply mixed. In this case, the long wavelength shift level of the maximum emission wavelength exhibited by the homogeneous organic composite is not particularly limited.

[0041] In another specific example, the homogeneous organic composite may be solid at room temperature, for example, a solid obtained by forming a homogeneous composition by utilizing the solubility physical properties of at least two organic compounds and an organic solvent and then removing the solvent.

[0042] In one example, the homogeneous organic composite can be obtained by completely dissolving the first organic compound and the second organic compound in at least one organic solvent to form a homogeneous phase and then solidifying. As described above, the shape of the solidified homogeneous organic composite is not particularly limited, for example, it can be a powder or a rod. According to demand, the homogeneous organic composite can also be obtained by physically crushing it with a mixer or the like to obtain a solid such as a block.

[0043] On the other hand, the homogeneous organic composite of the present invention is solidified after the molecules are mixed in a suitable solvent, so that the minimum non-uniform composition caused by the mixing of molecular groups between solids such as the existing pre-melting method can be fundamentally prevented. In addition, since the mixing is carried out using a solvent, the mixing can be carried out at a lower temperature than the pre-melting method without causing thermal damage.

[0044] In order to prepare such a homogeneous organic complex, it is appropriate to use at least one organic solvent having a similar solubility index (solubility) as at least two organic compounds as the mixed object substances. There is no particular limitation on the at least one organic solvent, as long as it is a substance that can form a homogeneous phase by dissolving the first organic compound and the second organic compound. For example, conventional organic solvents known in the art or mixed solvents of two or more mixtures can be used alone. Non-limiting examples of usable organic solvents include organic solvents such as tetrahydrofuran, methylenechloride, ethyl acetate, acetone, dimethyl ether, benzene, toluene, 1,2-dichlorobenzene, monochlorobenzene, methanol, ethanol, isopropyl alcohol, but are not limited thereto. There is no particular limitation on the mixing ratio between the two solvents, for example, it can be included in a molar ratio of 1:99 to 99:1. This molar ratio can also be expressed as a weight ratio. Furthermore, two or more co-solvents may be used to select a suitable solvent.

[0045] In another example, the homogeneous organic composite can be obtained by press-molding the solidified homogeneous organic composite under non-heat treatment conditions.

[0046] In this case, the press molding method is not particularly limited, and conventional molding methods known in the art can be used without restriction. For example, the press molding method can be used at 20000 kgf / cm 2 Up to 40000kgf / cm 2 The shape of the homogeneous organic composite formed by pressure molding as described above is not particularly limited, and for example, it can be a pellet selected from the group consisting of a polyhedron, a cylinder, and a sphere. In addition, it can be freely deformed into a solid having a shape and / or size required by the user.

[0047] The at least two organic compounds constituting the homogeneous organic composite of the present invention are not particularly limited, and organic compounds that can be used as organic layer materials of organic electroluminescent devices by vaporization and / or sublimation in the art can be used without limitation.

[0048] The homogeneous organic composite is formed into at least one homogeneous thin film of an organic layer included in an organic electroluminescent device by a conventional deposition method known in the art. Therefore, preferably, the first organic compound and the second organic compound constituting the homogeneous organic composite have deposition temperatures as similar as possible to each other. For example, the first organic compound and the second organic compound can be deposited at 10 -6 The deposition temperature difference is 0°C to 30°C at a pressure of torr.

[0049] Furthermore, the first organic compound and the second organic compound may be the same as or different from each other, and may be independently selected from the group consisting of a host material, an electron injection material, an electron transport material, an electron blocking material, a hole injection material, a hole transport material, a hole blocking material, and an exciton blocking material. Specifically, the first organic compound and the second organic compound may be host materials, more specifically, including at least two organic hosts, but excluding inorganic substances and dopants.

[0050] In the present invention, the mobility of electrons and holes can be improved by mixing a compound having strong electron properties and a compound having strong hole properties as at least two organic compounds constituting a homogeneous organic composite. For example, the first organic compound can be a compound having relatively strong hole properties, and the second organic compound can be a compound having relatively strong electron properties. As described above, the homogeneous organic composite composed of the first organic compound having relatively strong hole properties and the second organic compound having relatively strong electron properties has bipolar properties, and therefore, compared with the case of using the first organic compound or the second organic compound alone, the luminous efficiency can be significantly improved by increasing the mobility of electrons and holes.

[0051] Furthermore, in a device in which a material having electron-or hole-biased properties is introduced into a light-emitting layer, when carrier recombination occurs at the interface between the light-emitting layer and the electron or hole transport layer, more excitons are formed, resulting in reduced efficiency and life characteristics of the light-emitting layer. In contrast, in the present invention, a device capable of achieving carrier balance in the light-emitting layer is prepared by introducing a homogeneous organic complex of a first organic compound and a second organic compound as a material of an organic layer in a device such as a light-emitting layer material, thereby achieving an improved effect of luminous efficiency and life characteristics.

[0052] In the present invention, the first organic compound that can be used is not particularly limited as long as it is a compound having a stronger hole transport property than the second organic compound, that is, a hole transporting organic compound.

[0053] The hole transporting organic compound may be a hole transporting host. For example, the hole transporting host may be a carbazole compound.

[0054] Specifically, examples of the hole transporting organic compound include a compound represented by the following Chemical Formula 1. However, it is not limited thereto.

[0055] Chemical formula 1:

[0056]

[0057] In the above chemical formula 1,

[0058] D is deuterium,

[0059] a, d and f are integers from 0 to 3,

[0060] b, c and e are integers from 0 to 4, respectively.

[0061] Ar1 and Ar2 are the same as or different from each other and are independently selected from hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, phosphine oxide, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide and C6~C 60 or they can combine with adjacent groups to form a condensed ring,

[0062] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, alkylphosphine oxide, arylphosphine oxide, arylamine and condensed ring of Ar1 and Ar2 are each independently selected from deuterium, halogen, cyano, nitro, C2 to C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C1 to C 40 Alkyl, C6~C 60aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide and C6~C 60 The aromatic amine group may be substituted or unsubstituted with one or more substituents. When there are a plurality of such substituents, they may be the same as or different from each other.

[0063] In the compound represented by the above chemical formula 1, a, d and f are integers of 0 to 3, respectively, and b, c and e are integers of 0 to 4, respectively. Wherein, when a, b, c, d, e and f are 0, respectively, it means that hydrogen is not replaced by D as deuterium. On the other hand, when a, d and f are integers of 1 to 3, respectively, and when b, c and e are integers of 1 to 4, respectively, it means that more than one hydrogen is replaced by deuterium (D). In this case, it can be 13≤a+b+c+d+e+f≤21. As an example, the number of deuterium (D) contained in the compound represented by the above chemical formula 1 can be at least 13, specifically, it can be at least 21. This compound represented by chemical formula 1 improves the stability of the chemical structure by deuterium (D) substitution, so that the characteristics of the organic electroluminescent device, such as the low voltage, high efficiency and long life characteristics of the device, can be achieved at the same time.

[0064] This deuterium can also be replaced by other substituents (R). In this case, when there are multiple other substituents (R), they can be the same or different from each other. The above other substituents (R) can be selected from halogen groups, cyano groups, nitro groups, amino groups, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, phosphine oxide, C1~C 40Alkylphosphine oxide group, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide and C6~C 60 In the group composed of aromatic amine groups.

[0065] In the compound represented by the above Chemical Formula 1, Ar1 and Ar2 are the same as or different from each other and are each independently selected from hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, C1 to C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, phosphine oxide, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide and C6~C 60 In particular, Ar1 and Ar2 may be the same or different from each other and may be independently selected from C6 to C 60 The present invention is a group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

[0066] As an example, Ar1 and Ar2 may be the same as or different from each other, and may each independently be a substituent selected from the group consisting of substituents S1 to S4 described below.

[0067]

[0068] In the above substituents S1 to S4, * is a site for connection with the above Chemical Formula 1.

[0069] According to such Ar1 and Ar2, the compound represented by the above Chemical Formula 1 may be a compound represented by the following Chemical Formula 2, but is not limited thereto.

[0070] Chemical formula 2:

[0071]

[0072] In the above chemical formula 2,

[0073] a, b, c, d, e and f are respectively as defined in the above chemical formula 1,

[0074] m1 and m2 are 0 or 1 respectively.

[0075] Furthermore, the compound represented by the above Chemical Formula 1 may have various structures depending on the connection sites between the carbazole moieties. As an example, the compound represented by the above Chemical Formula 1 may be a compound represented by the following Chemical Formula 3.

[0076] Chemical formula 3:

[0077]

[0078] In the above chemical formula 3,

[0079] a, b, c, d, e and f are respectively as defined in the above chemical formula 1,

[0080] m1 and m2 are 0 or 1 respectively.

[0081] The compound represented by Chemical Formula 1 of the present invention described above may be further embodied as the compounds exemplified below, such as Compound A-1 to Compound D-4, but is not limited thereto.

[0082]

[0083]

[0084] In the present invention, the second organic compound that can be used is not particularly limited as long as it is a compound having a relatively stronger electron transport property than the first organic compound, that is, an electron transport organic compound.

[0085] The electron transporting organic compound may be an electron transporting host. For example, the electron transporting host may be a compound including at least one electron withdrawing group (EWG) represented by the following chemical formula.

[0086]

[0087] In the above chemical formula,

[0088] X1 to X8 and Y1 to Y5 are the same or different from each other and are each independently N or C(R), but the above monocyclic or polycyclic moiety contains at least one N,

[0089] When there are multiple C(R)s, the multiple Rs are the same or different from each other and are independently selected from hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 Alkyl, C2~C 40Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide and C6~C 60 or they can combine with adjacent groups to form a condensed ring,

[0090] The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamine, alkylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide and arylamine groups of R can be independently selected from hydrogen, deuterium (D), halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide and C6~C 60 The substituents may be substituted with one or more substituents selected from the group consisting of an aromatic amine group and, in this case, when a plurality of the substituents are present, they may be the same as or different from each other.

[0091] In a specific example, the second organic compound may be an azine compound containing at least one nitrogen-containing moiety represented by the following chemical formula: For example, it may be an electron transporting host containing at least one moiety selected from triazine, pyrimidine, quinoline, quinazoline and / or pyridine.

[0092]

[0093] Specifically, the electron transporting organic compound includes a compound represented by the following Chemical Formula 4, but is not limited thereto.

[0094] Chemical formula 4:

[0095]

[0096] In the above chemical formula 4,

[0097] D is deuterium,

[0098] H is an integer from 0 to 3,

[0099] g and i are integers from 0 to 4 respectively,

[0100] j and k are integers from 0 to 5 respectively,

[0101] n1 is an integer from 1 to 5,

[0102] n2 is an integer of 0 or 1,

[0103] X1 is selected from the group consisting of O, S, Se, N(Ar3), C(Ar4)(Ar5) and Si(Ar6)(Ar7),

[0104] Y1 and Y2 are the same as or different from each other and are each independently N or C(Ar8), in which case at least one of Y1 and Y2 is N,

[0105] Ar3 to Ar8 and R1 to R5 are the same as or different from each other and are each independently selected from hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, phosphine oxide, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide and C6~C 60or they can combine with adjacent groups to form a condensed ring,

[0106] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, alkylphosphine oxide, arylphosphine oxide, arylamine and condensed ring of Ar3 to Ar8 and R1 to R5 are each independently selected from deuterium, halogen, cyano, nitro, C2 to C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C1 to C 40 Alkyl, C6~C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide and C6~C 60 The aromatic amine group may be substituted or unsubstituted with one or more substituents. When there are a plurality of such substituents, they may be the same as or different from each other.

[0107] In the compound represented by the above Chemical Formula 4, Y1 and Y2 are the same as or different from each other and are each independently N or C(Ar8), but at least one of Y1 and Y2 is N.

[0108] According to such Y1 and Y2, in the compound represented by the above chemical formula 4, The moiety may be a moiety selected from the group consisting of the following moieties Mo-1 to Mo-3.

[0109]

[0110] In the above-mentioned parts Mo-1 to Mo-3,

[0111] * is the site connected to the above chemical formula 4,

[0112] Y1 and Y2 are each independently C(Ar8),

[0113] Ar8 is as defined in the above Chemical Formula 4.

[0114] In the compound represented by the above Chemical Formula 4, n1 is an integer of 1 to 5, and n2 is 0 or 1. As an example, n1 may be 1 or 2, and n2 may be 0 or 1. However, in the above Chemical Formula 4, when n2 is 0, j is 1.

[0115] In the compound represented by the above Chemical Formula 4, X1 is selected from the group consisting of O, S, Se, N(Ar3), C(Ar4)(Ar5) and Si(Ar6)(Ar7). According to such X1, the dibenzo part may be a monovalent dibenzofuranyl group, a monovalent dibenzothiophene group, a monovalent fluorenyl group, etc.

[0116] Ar3 to Ar8 are the same as or different from each other and are each independently selected from hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, phosphine oxide, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide and C6~C 60 or they can form a condensed ring with adjacent groups (e.g., Ar3-R1, Ar3-R2, Ar4-Ar5, Ar6-Ar7, Ar4-R1, Ar4-R2, Ar6-R1, Ar6-R2, etc.). Specifically, Ar3 to Ar8 are the same or different from each other and are independently selected from C1 to C 40 Alkyl, C6~C 60 The condensed ring may be selected from the group consisting of C3 to C 60 A fused aliphatic ring (specifically, C3 to C 30 Condensed aliphatic ring), C6~C 60A fused aromatic ring (specifically, C6 to C 30 fused aromatic ring), 5-membered to 60-membered fused heteroaromatic ring (specifically, 5-membered to 30-membered fused heteroaromatic ring), C3-C 60 One or more of the group consisting of a spiro ring and combinations thereof.

[0117] As an example, in the above chemical formula 4, The portion may be a portion selected from the group consisting of portion Dz-1 to portion Dz-32 described below, but is not limited thereto.

[0118]

[0119]

[0120] In the above-mentioned section Dz-1 and section Dz-32,

[0121] * is the site connected to the above chemical formula 4,

[0122] R1 can be C6~C 60 The aryl group may specifically be a phenyl group.

[0123] In the compound represented by the above chemical formula 4, h is an integer of 0 to 3, g and i are integers of 0 to 4, and j and k are integers of 0 to 5. When g, h, i, j and k are 0, it means that hydrogen is not replaced by R1 to R5 as a substituent. On the other hand, when h is an integer of 1 to 3, when g and i are integers of 1 to 4, and when j and k are integers of 1 to 5, one or more R1 to R5 are the same or different from each other, and are independently selected from deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, phosphine oxide, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine, C6~C 60Aryl phosphine oxide and C6~C 60 In particular, one or more R1 to R5 may be the same or different from each other and may be independently selected from hydrogen, a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 Alkyl, C6~C 60 The present invention is a group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

[0124] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, alkylphosphine oxide, arylphosphine oxide, arylamine and condensed ring of Ar3 to Ar8 and R1 to R5 can be independently selected from deuterium, halogen, cyano, nitro, C2 to C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C1 to C 40 Alkyl, C6~C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide and C6~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents in the group consisting of. In this case, when there are a plurality of the above substituents, they may be the same as or different from each other.

[0125] The compound represented by the above Chemical Formula 4 may be a compound represented by the following Chemical Formula 5, but is not limited thereto.

[0126] Chemical formula 5:

[0127]

[0128] In the above chemical formula 5,

[0129] i, j, k, R1, R3 to R5, n1, n2, X1, Y1 and Y2 are respectively defined as in the above Chemical Formula 4.

[0130] Specifically, the compound represented by the above Chemical Formula 4 may be a compound represented by the following Chemical Formula 6 or Chemical Formula 7, but is not limited thereto.

[0131] Chemical formula 6:

[0132]

[0133] Chemical formula 7:

[0134]

[0135] In the above Chemical Formula 6 and Chemical Formula 7,

[0136] i, k, R1, R3, R5, n1, n2, Y1 and Y2 are respectively as defined in the above chemical formula 4,

[0137] X1 and X2 may be O or S, respectively, and specifically, may be O.

[0138] More specifically, the compound represented by the above Chemical Formula 4 may be a compound represented by the following Chemical Formula 8 or Chemical Formula 9, but is not limited thereto.

[0139] Chemical formula 8:

[0140]

[0141] Chemical formula 9:

[0142]

[0143] In the above Chemical Formula 8 and Chemical Formula 9,

[0144] n1, n2, Y1 and Y2 are respectively defined as in the above chemical formula 4. Specifically, n1 can be 1 or 2, n2 can be 0 or 1, and Y1 and Y2 can both be N.

[0145] x and y are 0 or 1 respectively,

[0146] X1 and X2 may be O or S, respectively, and specifically, may be O.

[0147] The compound represented by Chemical Formula 2 of the present invention described above may be further embodied as the compounds exemplified below, such as Compound E-1 to Compound E-10, but is not limited thereto.

[0148]

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

[0150] 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 having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

[0151] In the present invention, "alkynyl" refers to 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, and examples thereof include ethynyl, 2-propynyl, etc., but are not limited thereto.

[0152] 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 of such cycloalkyl include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, etc., but are not limited thereto.

[0153] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 core atoms, wherein one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted by heteroatoms such as N, O, S or Se. Examples of such heterocycloalkyl include morpholine, piperazine, etc., but are not limited thereto.

[0154] In the present invention, "aryl" refers to a monovalent substituent of an aromatic hydrocarbon having 6 to 60 carbon atoms and derived from a single ring or a combination of two or more rings. In addition, it may include a form in which two or more rings are simply attached (pendant) or fused to each other. Examples of such aryl groups include phenyl, naphthyl, phenanthrenyl, anthracenyl, etc., but are not limited thereto.

[0155] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted by heteroatoms such as N, O, S or Se. In addition, it may include a form in which two or more rings are simply attached (pendant) or fused to each other, and further, it may include a form fused with an aromatic group. Examples of such heteroaryl groups include 6-membered monocyclic rings, such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; polycyclic rings, such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, etc.; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.

[0156] In the present invention, "alkoxy" is a monovalent substituent represented by R'O-, wherein R' refers to an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched or cyclic structure. Examples of such alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, pentoxy, and the like.

[0157] In the present invention, "aryloxy" is a monovalent substituent represented by RO-, and the above R is an aryl group having 5 to 40 carbon atoms. Examples of such aryloxy include phenoxy, naphthoxy, diphenoxy, etc., but are not limited thereto.

[0158] In the present invention, "alkylsilyl" refers to a silyl group substituted by an alkyl group having 1 to 40 carbon atoms, including monoalkylsilyl, dialkylsilyl and trialkylsilyl. In addition, "arylsilyl" refers to a silyl group substituted by an aryl group having 5 to 60 carbon atoms, including not only monoarylsilyl but also polyarylsilyl groups such as diarylsilyl and triarylsilyl.

[0159] In the present invention, the "alkylboryl group" refers to a boron group substituted by an alkyl group having 1 to 40 carbon atoms, and the "arylboryl group" refers to a boron group substituted by an aryl group having 6 to 60 carbon atoms.

[0160] In the present invention, "alkylphosphino" refers to a phosphino substituted by an alkyl group having 1 to 40 carbon atoms, including a monoalkylphosphino and a dialkylphosphino. In addition, in the present invention, "arylphosphino" refers to a phosphino substituted by a monoaryl or diaryl group having 6 to 60 carbon atoms, including a monoarylphosphino and a diarylphosphino.

[0161] In the present invention, "arylamine" refers to an amine substituted with an aryl group having 6 to 60 carbon atoms, including monoarylamine and diarylamine.

[0162] In the present invention, "heteroarylamine" refers to an amine substituted with a heteroaryl group having 5 to 60 nuclear atoms, including monoheteroarylamine and diheteroarylamine.

[0163] In the present invention, (aryl)(heteroaryl)amine refers to an amine substituted with an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms.

[0164] In the present invention, "fused ring" refers to a fused aliphatic ring having 3 to 40 carbon atoms, a fused aromatic ring having 6 to 60 carbon atoms, a fused heteroaliphatic ring having 3 to 60 nuclear atoms, a fused heteroaromatic ring having 5 to 60 nuclear atoms, a spiro ring having 3 to 60 carbon atoms, or a combination thereof.

[0165] The homogeneous organic composite of the present invention can be obtained by using the first organic compound and the second organic compound in a weight ratio of, for example, about 1:99 to 99:1. For example, the first organic compound and the second organic compound can be included in a weight ratio of 20:80 to 80:20. By including in the above range, the bipolar characteristics can be more effectively achieved, so the efficiency and life characteristics of the device can be improved at the same time.

[0166] The homogeneous organic composite can be used as at least one organic material contained in an organic electroluminescent device, for example, as a luminescent material, a light absorbing material, a charge transport material, a charge injection material, a charge blocking material or a combination thereof. Specifically, the homogeneous organic composite can be used as a luminescent material, more specifically, as a host.

[0167] On the other hand, the homogeneous organic composite of the present invention can be prepared by utilizing the solubility physical property of at least two organic compounds with an organic solvent.

[0168] In one embodiment of preparing the above-mentioned homogeneous organic composite, it can be constructed to include: a first step of completely dissolving two or more vaporizable or sublimable organic compounds in at least one organic solvent to form a homogeneous phase and then solidifying; and a second step of pressurizing the solidified homogeneous organic composite under non-heat treatment conditions.

[0169] In this case, the molding conditions of the second step are not particularly limited, and for example, the molding conditions may be 20000 kgf / cm 2 Up to 40000kgf / cm 2 Injection molding under pressure.

[0170] Also, the solidified homogeneous organic composite prepared in the first step may be in the form of powder or rod, and the homogeneous organic composite molded in the second step may be in the form of particles selected from the group consisting of polyhedrons, cylinders, and spheres. However, it is not particularly limited thereto.

[0171] In addition, the components constituting the homogeneous organic composite of the present invention are the same as those described above, and thus their individual descriptions will be omitted.

[0172] The particulate homogeneous organic composite prepared as described above can be deposited by conventional vacuum deposition methods such as evaporation and sputtering, and can be used as any layer of at least one organic layer included in an organic electroluminescent device.

[0173] <Organic electroluminescent device>

[0174] On the other hand, another example of the present invention relates to an organic electroluminescent device (organic EL device) comprising the above-mentioned homogeneous organic composite of the present invention as an organic layer material of at least one layer.

[0175] Specifically, the present invention is an organic electroluminescent device, which includes: an anode; a cathode; and one or more organic layers between the anode and the cathode, at least one of the one or more organic layers includes a homogeneous film formed by a homogeneous organic composite.

[0176] The above-mentioned one or more organic layers can be any one of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a life improvement layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer. Specifically, the organic layer containing the above-mentioned homogeneous organic composite can be a light-emitting layer.

[0177] In this case, the first organic compound may be a hole transporting host, and the second organic compound may be an electron transporting host. The mixing ratio of the first organic compound and the second organic compound is not particularly limited, for example, it may be a weight ratio of 1:99 to 99:1, specifically 20:80 to 80:20.

[0178] In addition to the first organic compound and the second organic compound, the light-emitting layer may further include a host and / or a dopant generally known in the art. In this case, the total content of the first organic compound and the second organic compound may be 0 weight percent to 100 weight percent relative to the total amount of all hosts.

[0179] Also, the total amount of all hosts may be about 70 weight percent to 99.9 weight percent relative to the total amount of the light emitting layer, and the content of the dopant may be about 0.1 weight percent to 30 weight percent relative to the total amount of the light emitting layer.

[0180] The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, an electron transport layer and a cathode are sequentially stacked. In this case, one or more of the hole injection layer, the hole transport layer, the luminescence auxiliary layer, the luminescent layer, the electron transport layer and the electron injection layer may contain the homogeneous organic composite, and preferably, the luminescent layer may contain a homogeneous organic mixture. On the other hand, an electron injection layer may also be stacked on the electron transport layer.

[0181] The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0182] In addition to at least one of the organic layers comprising the homogeneous organic composite, the organic electroluminescent device of the present invention can be prepared by forming the organic layers and electrodes using materials and methods known in the art.

[0183] The organic layer may be formed by a dry film forming method such as vacuum evaporation, sputtering, plasma plating, or ion plating, but is not limited thereto.

[0184] The substrate used in preparing the organic electroluminescent device of the present invention is not particularly limited. For example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

[0185] Furthermore, the anode material may be any anode material known in the art without limitation. For example, it may include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; combinations of metals and oxides such as ZnO:Al or SnO2:Sb; polythiophene, poly(3-methylthiophene), such as poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline, etc., conductive polymers; and carbon black, etc., but not limited thereto.

[0186] Furthermore, the cathode material may be any cathode material known in the art without limitation, for example, may include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof, and multilayer structure materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0187] Furthermore, the hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer are not particularly limited, and conventional materials known in the art can be used without limitation.

[0188] Hereinafter, the present invention will be described in detail by way of examples as follows. However, the following examples are only for illustrating the present invention, and the present invention is not limited to the following examples.

[0189] Preparation Example 1-1: Synthesis of Cz-D1

[0190]

[0191] Under a nitrogen flow, 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (134.3 g, 530.6 mmol), iodobenzene (130.0 g, 636.7 mmol), Cu (16.8 g, 265.3 mmol), K2CO3 (146.7 g, 1,061.3 mmol) and toluene (1000 ml) were mixed and stirred at 110°C for 12 hours.

[0192] After the reaction was completed, it was extracted with ethyl acetate, and then MgSO4 was used to remove moisture, and purified by column chromatography (Hexane:EA=5:1 (v / v)) to obtain Cz-D1 (125.7 g, yield: 72%).

[0193] Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0194] Preparation Example 1-2: Synthesis of Cz-D2

[0195]

[0196] The same process as in Preparation Example 1-1 was carried out except that 4-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 1-1 to obtain Cz-D2 (135.5 g, yield 63%) as the target compound.

[0197] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0198] Preparation Example 1-3: Synthesis of Cz-D3

[0199]

[0200] The same process as in Preparation Example 1-1 was carried out except that 3-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 1-1 to obtain Cz-D3 (148.4 g, yield 69%) as the target compound.

[0201] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0202] Preparation Example 1-4: Synthesis of Cz-D4

[0203]

[0204] The same process as Preparation Example 1-1 was carried out except that 2-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 1-1 to obtain Cz-D4 (96.8 g, yield 45%) as the target compound.

[0205] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0206] Preparation Example 2-1: Synthesis of Cz-D5

[0207]

[0208] The same process as in Preparation Example 1-1 was carried out except that 4-bromo-9H-carbazole-1,2,3,5,6,7,8-d7 (4-bromo-9H-carbazole-1,2,3,5,6,7,8-d7) (134.3 g, 530.6 mmol) was used instead of 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7) used in Preparation Example 1-1 to obtain Cz-D5 (117.1 g, yield 67%) as the target compound.

[0209] Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0210] Preparation Example 2-2: Synthesis of Cz-D6

[0211]

[0212] The same process as in Preparation Example 2-1 was carried out except that 4-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 2-1 to obtain Cz-D6 (139.8 g, yield 65%) as the target compound.

[0213] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0214] Preparation Example 2-3: Synthesis of Cz-D7

[0215]

[0216] The same process as in Preparation Example 2-1 was carried out except that 3-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 2-1 to obtain Cz-D7 (152.7 g, yield 71%) as the target compound.

[0217] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0218] Preparation Example 2-4: Synthesis of Cz-D8

[0219]

[0220] The same process as in Preparation Example 2-1 was carried out except that 2-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 2-1 to obtain Cz-D8 (75.2 g, yield 35%) as the target compound.

[0221] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0222] Preparation Example 3-1: Synthesis of Cz-D9

[0223]

[0224] The same process as in Preparation Example 1-1 was carried out except that 2-bromo-9H-carbazole-1,3,4,5,6,7,8-d7 (2-bromo-9H-carbazole-1,3,4,5,6,7,8-d7) (134.3 g, 530.6 mmol) was used instead of 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7) used in Preparation Example 1-1 to obtain Cz-D9 (134.5 g, yield 77%) as the target compound.

[0225] Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0226] Preparation Example 3-2: Synthesis of Cz-D10

[0227]

[0228] The same process as in Preparation Example 3-1 was carried out except that 4-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 3-1 to obtain Cz-D10 (159.1 g, yield 74%) as the target compound.

[0229] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0230] Preparation Example 3-3: Synthesis of Cz-D11

[0231]

[0232] The same process as in Preparation Example 3-1 was carried out except that 3-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 3-1 to obtain Cz-D11 (163.4 g, yield 76%) as the target compound.

[0233] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0234] Preparation Example 3-4: Synthesis of Cz-D12

[0235]

[0236] The same process as in Preparation Example 3-1 was carried out except that 2-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 3-1 to obtain Cz-D12 (92.4 g, yield 43%) as the target compound.

[0237] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0238] Preparation Example 4-1: Synthesis of Cz-D13

[0239]

[0240] The same process as in Preparation Example 1-1 was carried out except that 1-bromo-9H-carbazole-2,3,4,5,6,7,8-d7 (1-bromo-9H-carbazole-2,3,4,5,6,7,8-d7) (134.3 g, 530.6 mmol) was used instead of 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7) used in Preparation Example 1-1 to obtain Cz-D13 (94.3 g, yield 54%) as the target compound.

[0241] Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0242] Preparation Example 4-2: Synthesis of Cz-D14

[0243]

[0244] The same process as in Preparation Example 4-1 was carried out except that 4-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 4-1 to obtain Cz-D14 (122.6 g, yield 57%) as the target compound.

[0245] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0246] Preparation Example 4-3: Synthesis of Cz-D15

[0247]

[0248] The same process as in Preparation Example 4-1 was carried out except that 3-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 4-1 to obtain Cz-D15 (111.8 g, yield 52%) as the target compound.

[0249] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0250] Preparation Example 4-4: Synthesis of Cz-D16

[0251]

[0252] The same process as in Preparation Example 4-1 was carried out except that 2-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 4-1 to obtain Cz-D16 (68.8 g, yield 32%) as the target compound.

[0253] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0254] Preparation Example 5-1: Synthesis of BCz-D1

[0255] Step 1: 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4, 5,6,7,8-d7

[0256] (9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H- Synthesis of carbazole-1,2,4,5,6,7,8-d7)

[0257]

[0258] Under nitrogen flow, Cz-D1 (100.0 g, 303.7 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (84.8 g, 334.1 mmol), Pd(dppf)Cl2 (26.6 g, 30.3 mmol), KOAc (85.8 g, 911.1 mmol) and 1,4-dioxane (1000 ml) were mixed and stirred at 130°C for 12 hours.

[0259] After the reaction was completed, it was extracted with ethyl acetate, and then MgSO4 was used to remove moisture, and purified by column chromatography (Hexane:EA=8:1 (v / v)) to obtain 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 (9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7) (96.0 g, yield was 84%).

[0260] Mass (theoretical value: 376.3, measured value: 376 g / mol)

[0261] Step 2: Synthesis of BCz-D1

[0262]

[0263] Under nitrogen flow, 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7

[0264] (9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7)(96.0g, 255.1mmol), 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7(3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7)(77.5g, 306.1mmol), Pd(PPh3)4(14.7g, 12.7mmol), K2CO3(88.1g, 637.8mmol), 1,4-dioxane / H2O(1000ml / 250ml) were mixed and stirred at 120°C for 4 hours.

[0265] After the reaction was completed, it was extracted with dichloromethane, and MgSO4 was added for filtration. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane:EA=7:1 (v / v)) to obtain BCz-D1 (71.1 g, yield 66%).

[0266] Mass (theoretical value: 422.59, measured value: 422 g / mol)

[0267] Preparation Example 5-2: Synthesis of BCz-D2

[0268]

[0269] The same process as in Preparation Example 5-1 was carried out except that Cz-D2 (100 g, 246.7 mmol) obtained in Preparation Example 1-2 was used instead of Cz-D1 used in Preparation Example 5-1 to obtain BCz-D2 (66.4 g, final yield 54.0%) as the target compound.

[0270] Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0271] Preparation Example 5-3: Synthesis of BCz-D3

[0272]

[0273] The same process as in Preparation Example 5-1 was carried out except that Cz-D3 (100 g, 246.7 mmol) obtained in Preparation Example 1-3 was used instead of Cz-D1 used in Preparation Example 5-1 to obtain BCz-D3 (59.7 g, final yield 48.5%) as the target compound.

[0274] Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0275] Preparation Example 5-4: Synthesis of BCz-D4

[0276]

[0277] The same process as in Preparation Example 5-1 was carried out except that Cz-D4 (100 g, 246.7 mmol) obtained in Preparation Example 1-4 was used instead of Cz-D1 used in Preparation Example 5-1 to obtain BCz-D4 (59.4 g, final yield 48.3%) as the target compound.

[0278] Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0279] Synthesis Example 1: Synthesis of A-1

[0280]

[0281] Under nitrogen flow, BCz-D1 (10.0 g, 23.6 mmol) obtained in Preparation Example 5-1, Cz-D1 (9.3 g, 28.3 mmol) obtained in Preparation Example 1-1, Pd(OAc)2 (1.36 g, 1.18 mmol), P(t-Bu)3 (0.57 ml, 2.36 mmol), NaO(t-Bu) (4.55 g, 47.3 mmol) and toluene (100 ml) were mixed and stirred at 110°C for 5 hours. After the reaction was completed, toluene was concentrated, and the solid salt was filtered, and then purified by recrystallization to obtain A-1 (13.0 g, yield 82%) as the target compound.

[0282] Mass (theoretical value: 670.93, measured value: 670 g / mol)

[0283] Synthesis Example 2: Synthesis of A-2

[0284]

[0285] The same process as in Synthesis Example 1 was carried out, except that Cz-D2 (10.0 g, 23.6 mmol) obtained in Preparation Example 1-2 was used instead of Cz-D1 used in Synthesis Example 1, to obtain A-2 (13.8 g, yield 78%) as the target compound.

[0286] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0287] Synthesis Example 3: Synthesis of A-3

[0288]

[0289] The same process as in Synthesis Example 1 was carried out except that Cz-D3 (10.0 g, 23.6 mmol) obtained in Preparation Example 1-3 was used instead of Cz-D1 used in Synthesis Example 1 to obtain A-3 (13.2 g, yield 75%) as the target compound.

[0290] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0291] Synthesis Example 4: Synthesis of A-4

[0292]

[0293] The same process as in Synthesis Example 1 was carried out except that Cz-D4 (10.0 g, 23.6 mmol) obtained in Preparation Example 1-4 was used instead of Cz-D1 used in Synthesis Example 1 to obtain A-4 (12.2 g, yield 69%) as the target compound.

[0294] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0295] Synthesis Example 5: Synthesis of A-5

[0296]

[0297] The same process as in Synthesis Example 1 was carried out except that Cz-D5 (9.3 g, 23.6 mmol) obtained in Preparation Example 2-1 was used instead of Cz-D1 used in Synthesis Example 1 to obtain A-5 (8.73 g, yield 55%) as the target compound.

[0298] Mass (theoretical value: 670.93, measured value: 670 g / mol)

[0299] Synthesis Example 6: Synthesis of A-6

[0300]

[0301] The same process as in Synthesis Example 1 was carried out, except that Cz-D6 (10.0 g, 23.6 mmol) obtained in Preparation Example 2-2 was used instead of Cz-D1 used in Synthesis Example 1, to obtain A-6 (7.42 g, yield 42%) as the target compound.

[0302] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0303] Synthesis Example 7: Synthesis of A-7

[0304]

[0305] The same process as in Synthesis Example 1 was carried out except that Cz-D7 (10.0 g, 23.6 mmol) obtained in Preparation Example 2-3 was used instead of Cz-D1 used in Synthesis Example 1 to obtain A-7 (8.83 g, yield 50%) as the target compound.

[0306] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0307] Synthesis Example 8: Synthesis of A-8

[0308]

[0309] The same process as in Synthesis Example 1 was carried out except that Cz-D8 (10.0 g, 23.6 mmol) obtained in Preparation Example 2-4 was used instead of Cz-D1 used in Synthesis Example 1 to obtain A-8 (9.89 g, yield 56%) as the target compound.

[0310] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0311] Synthesis Example 9: Synthesis of A-9

[0312]

[0313] The same process as in Synthesis Example 1 was carried out except that Cz-D9 (9.3 g, 23.6 mmol) obtained in Preparation Example 3-1 was used instead of Cz-D1 used in Synthesis Example 1 to obtain A-9 (8.41 g, yield 53%) as the target compound.

[0314] Mass (theoretical value: 670.93, measured value: 670 g / mol)

[0315] Synthesis Example 10: Synthesis of A-10

[0316]

[0317] The same process as in Synthesis Example 1 was carried out except that Cz-D10 (10.0 g, 23.6 mmol) obtained in Preparation Example 3-2 was used instead of Cz-D1 used in Synthesis Example 1 to obtain A-10 (8.66 g, yield 49%) as the target compound.

[0318] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0319] Synthesis Example 11: Synthesis of A-11

[0320]

[0321] The same process as in Synthesis Example 1 was carried out except that Cz-D11 (10.0 g, 23.6 mmol) obtained in Preparation Example 3-3 was used instead of Cz-D1 used in Synthesis Example 1 to obtain A-11 (9.01 g, yield 51%) as the target compound.

[0322] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0323] Synthesis Example 12: Synthesis of A-12

[0324]

[0325] The same process as in Synthesis Example 1 was carried out except that Cz-D12 (10.0 g, 23.6 mmol) obtained in Preparation Example 3-4 was used instead of Cz-D1 used in Synthesis Example 1 to obtain A-12 (9.19 g, yield 52%) as the target compound.

[0326] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0327] Synthesis Example 13: Synthesis of A-13

[0328]

[0329] The same process as in Synthesis Example 1 was carried out except that Cz-D13 (9.3 g, 23.6 mmol) obtained in Preparation Example 4-1 was used instead of Cz-D1 used in Synthesis Example 1 to obtain A-13 (9.52 g, yield 60%) as the target compound.

[0330] Mass (theoretical value: 670.93, measured value: 670 g / mol)

[0331] Synthesis Example 14: Synthesis of A-14

[0332]

[0333] The same process as in Synthesis Example 1 was carried out except that Cz-D14 (10.0 g, 23.6 mmol) obtained in Preparation Example 4-2 was used instead of Cz-D1 used in Synthesis Example 1 to obtain A-14 (10.78 g, yield 61%) as the target compound.

[0334] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0335] Synthesis Example 15: Synthesis of A-15

[0336]

[0337] The same process as in Synthesis Example 1 was carried out except that Cz-D15 (10.0 g, 23.6 mmol) obtained in Preparation Example 4-3 was used instead of Cz-D1 used in Synthesis Example 1 to obtain A-15 (11.13 g, yield 63%) as the target compound.

[0338] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0339] Synthesis Example 16: Synthesis of A-16

[0340]

[0341] The same process as in Synthesis Example 1 was carried out except that Cz-D16 (10.0 g, 23.6 mmol) obtained in Preparation Example 4-4 was used instead of Cz-D1 used in Synthesis Example 1 to obtain A-16 (9.02 g, yield 51%) as the target compound.

[0342] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0343] Synthesis Example 17: Synthesis of B-1

[0344]

[0345] Under nitrogen flow, BCz-D2 (10.0 g, 20.1 mmol) obtained in Preparation Example 5-2, Cz-D1 (7.9 g, 24.1 mmol) obtained in Preparation Example 1-1, Pd(OAc)2 (1.15 g, 1.0 mmol), P(t-Bu)3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol) and toluene (100 ml) were mixed and stirred at 110°C for 5 hours. After the reaction was completed, toluene was concentrated, and the solid salt was filtered, and then purified by recrystallization to obtain B-1 (10.2 g, yield 62%) as the target compound.

[0346] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0347] Synthesis Example 18: Synthesis of B-2

[0348]

[0349] The same process as in Synthesis Example 17 was carried out except that Cz-D5 (7.9 g, 24.1 mmol) obtained in Preparation Example 2-1 was used instead of Cz-D1 used in Synthesis Example 17 to obtain B-2 (8.5 g, yield 48%) as the target compound.

[0350] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0351] Synthesis Example 19: Synthesis of B-3

[0352]

[0353] The same process as in Synthesis Example 17 was carried out except that Cz-D9 (7.9 g, 24.1 mmol) obtained in Preparation Example 3-1 was used instead of Cz-D1 used in Synthesis Example 17 to obtain B-3 (11.1 g, yield 63%) as the target compound.

[0354] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0355] Synthesis Example 20: Synthesis of B-4

[0356]

[0357] The same process as in Synthesis Example 17 was carried out except that Cz-D13 (7.9 g, 24.1 mmol) obtained in Preparation Example 4-1 was used instead of Cz-D1 used in Synthesis Example 17 to obtain B-4 (7.42 g, yield 42%) as the target compound.

[0358] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0359] Synthesis Example 21: Synthesis of C-1

[0360]

[0361] Under nitrogen flow, BCz-D3 (10.0 g, 20.1 mmol) obtained in Preparation Example 5-3, Cz-D1 (7.9 g, 24.1 mmol) obtained in Preparation Example 1-1, Pd(OAc)2 (1.15 g, 1.0 mmol), P(t-Bu)3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol) and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, toluene was concentrated, and the solid salt was filtered, and then purified by recrystallization to obtain C-1 (9.4 g, yield 63%) as the target compound.

[0362] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0363] Synthesis Example 22: Synthesis of C-2

[0364]

[0365] The same process as in Synthesis Example 21 was carried out except that Cz-D5 (7.9 g, 24.1 mmol) obtained in Preparation Example 2-1 was used instead of Cz-D1 used in Synthesis Example 21 to obtain C-2 (7.78 g, yield 44%) as the target compound.

[0366] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0367] Synthesis Example 23: Synthesis of C-3

[0368]

[0369] The same process as in Synthesis Example 21 was carried out, except that Cz-D9 (7.9 g, 24.1 mmol) obtained in Preparation Example 3-1 was used instead of Cz-D1 used in Synthesis Example 21, to obtain C-3 (11.67 g, yield 66%) as the target compound.

[0370] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0371] Synthesis Example 24: Synthesis of C-4

[0372]

[0373] The same process as in Synthesis Example 21 was carried out except that Cz-D13 (7.9 g, 24.1 mmol) obtained in Preparation Example 4-1 was used instead of Cz-D1 used in Synthesis Example 21 to obtain C-4 (6.89 g, yield 39%) as the target compound.

[0374] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0375] Synthesis Example 25: Synthesis of D-1

[0376]

[0377] Under nitrogen flow, BCz-D4 (10.0 g, 20.1 mmol) obtained in Preparation Example 5-4, Cz-D1 (7.9 g, 24.1 mmol) obtained in Preparation Example 1-1, Pd(OAc)2 (1.15 g, 1.0 mmol), P(t-Bu)3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol) and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, toluene was concentrated, and the solid salt was filtered, and then purified by recrystallization to obtain D-1 (8.1 g, yield 54%) as the target compound.

[0378] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0379] Synthesis Example 26: Synthesis of D-2

[0380]

[0381] The same process as in Synthesis Example 25 was carried out except that Cz-D5 (7.9 g, 24.1 mmol) obtained in Preparation Example 2-1 was used instead of Cz-D1 used in Synthesis Example 25 to obtain D-2 (7.24 g, yield 41%) as the target compound.

[0382] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0383] Synthesis Example 27: Synthesis of D-3

[0384]

[0385] The same process as in Synthesis Example 25 was carried out except that Cz-D9 (7.9 g, 24.1 mmol) obtained in Preparation Example 3-1 was used instead of Cz-D1 used in Synthesis Example 25 to obtain D-3 (8.41 g, yield 51%) as the target compound.

[0386] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0387] Synthesis Example 28: Synthesis of D-4

[0388]

[0389] The same process as in Synthesis Example 25 was carried out except that Cz-D13 (7.9 g, 24.1 mmol) obtained in Preparation Example 4-1 was used instead of Cz-D1 used in Synthesis Example 25 to obtain D-4 (5.47 g, yield 31%) as the target compound.

[0390] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0391] Preparation Example 6: Synthesis of DBF-1

[0392] Step 1: 4-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan Synthesis of phenyldibenzo[b,d]furan

[0393]

[0394] Under a nitrogen flow, 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]furan-4-yl)-1,3,2-dioxaborolane) (100.0 g, 270.0 mmol), 1-bromo-3-chlorobenzene (62.0 g, 324.1 mmol), Pd(PPh3)4 (15.6 g, 13.5 mmol), K2CO3 (93.3 g, 675.2 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0395] After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO4. Then, the solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: DCM = 9: 1 (v / v)) to obtain 4-(3-chlorophenyl)-6-phenyldibenzo[b, d]furan (48.9 g, 51% yield).

[0396] Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0397] Step 2: Synthesis of DBF-1

[0398]

[0399] Under nitrogen flow, 4-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan (48.9 g, 137.7 mmol) obtained in the above step 1, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (38.5 g, 151.5 mmol), Pd(dppf)Cl2 (12.1 g, 13.8 mmol), KOAc (38.9 g, 413.2 mmol) and 1,4-dioxane (1000 ml) were mixed and stirred at 130°C for 12 hours.

[0400] After the reaction was completed, it was extracted with ethyl acetate, and then MgSO4 was used to remove moisture, and purified by column chromatography (Hexane: DCM = 4: 1 (v / v)) to obtain DBF-1 (26.4 g, yield 43%).

[0401] Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0402] Preparation Example 7: Synthesis of DBF-2

[0403] Step 1: 4-(4-chlorophenyl)-6-phenyldibenzo[b,d]furan Synthesis of phenyldibenzo[b,d]furan

[0404]

[0405] Under a nitrogen flow, 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]furan-4-yl)-1,3,2-dioxaborolane) (100.0 g, 270.0 mmol), 1-bromo-4-chlorobenzene (62.0 g, 324.1 mmol), Pd(PPh3)4 (15.6 g, 13.5 mmol), K2CO3 (93.3 g, 675.2 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0406] After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO4. Then, the solvent was removed from the resulting organic layer and then purified by column chromatography (Hexane: DCM = 9: 1 (v / v)) to obtain 4-(4-chlorophenyl)-6-phenyldibenzo[b, d]furan (60.4 g, 63% yield).

[0407] Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0408] Step 2: Synthesis of DBF-2

[0409]

[0410] Under nitrogen flow, 4-(4-chlorophenyl)-6-phenyldibenzo[b,d]furan (60.4 g, 170.2 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (47.5 g, 187.2 mmol), Pd(dppf)Cl2 (14.9 g, 17.0 mmol), KOAc (48.1 g, 510.4 mmol) and 1,4-dioxane (1000 ml) obtained in the above step 1 were mixed and stirred at 130°C for 12 hours.

[0411] After the reaction was completed, it was extracted with ethyl acetate, and then MgSO4 was used to remove moisture, and purified by column chromatography (Hexane: DCM = 4: 1 (v / v)) to obtain DBF-2 (36.5 g, yield 48%).

[0412] Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0413] Preparation Example 8: Synthesis of DBF-3

[0414] Step 1: 3-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan Synthesis of phenyldibenzo[b,d]furan

[0415]

[0416] Under a nitrogen flow, 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane (100.0 g, 270.0 mmol), 1-bromo-3-chlorobenzene (62.0 g, 324.1 mmol), Pd(PPh3)4 (15.6 g, 13.5 mmol), K2CO3 (93.3 g, 675.2 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0417] After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO4. Then, the solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: DCM = 9: 1 (v / v)) to obtain 3-(3-chlorophenyl)-6-phenyldibenzo[b, d]furan (68.0 g, 71% yield).

[0418] Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0419] Step 2: Synthesis of DBF-3

[0420]

[0421] Under nitrogen flow, 3-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan (68.0 g, 191.8 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (53.6 g, 210.9 mmol), Pd(dppf)Cl2 (16.8 g, 19.2 mmol), KOAc (54.2 g, 575.3 mmol) and 1,4-dioxane (1000 ml) obtained in the above step 1 were mixed and stirred at 130°C for 12 hours.

[0422] After the reaction was completed, it was extracted with ethyl acetate, and then MgSO4 was used to remove moisture, and purified by column chromatography (Hexane: DCM = 4: 1 (v / v)) to obtain DBF-3 (54.8 g, yield 64%).

[0423] Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0424] Preparation Example 9: Synthesis of DBF-4

[0425] Step 1: 1-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan Synthesis of phenyldibenzo[b,d]furan

[0426]

[0427] Under a nitrogen flow, 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]furan-1-yl)-1,3,2-dioxaborolane (100.0 g, 270.0 mmol), 1-bromo-3-chlorobenzene (62.0 g, 324.1 mmol), Pd(PPh3)4 (15.6 g, 13.5 mmol), K2CO3 (93.3 g, 675.2 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0428] After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO4. Then, the solvent was removed from the resulting organic layer and then purified by column chromatography (Hexane: DCM = 9: 1 (v / v)) to obtain 1-(3-chlorophenyl)-6-phenyldibenzo[b, d]furan (62.3 g, 65% yield).

[0429] Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0430] Step 2: Synthesis of DBF-4

[0431]

[0432] Under nitrogen flow, 1-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan (62.3 g, 175.6 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (49.0 g, 193.1 mmol), Pd(dppf)Cl2 (15.4 g, 17.6 mmol), KOAc (49.6 g, 526.7 mmol) and 1,4-dioxane (1000 ml) obtained in the above step 1 were mixed and stirred at 130°C for 12 hours.

[0433] After the reaction was completed, it was extracted with ethyl acetate, and then MgSO4 was used to remove moisture, and purified by column chromatography (Hexane: DCM = 4: 1 (v / v)) to obtain DBF-4 (45.4 g, yield 58%).

[0434] Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0435] Preparation Example 10: Synthesis of DBF-5

[0436] Step 1: 1-(3-chlorophenyl)-9-phenyldibenzo[b,d]furan Synthesis of phenyldibenzo[b,d]furan

[0437]

[0438] Under a nitrogen flow, 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-1-yl)-1,3,2-dioxaborolane (100.0 g, 270.0 mmol), 1-bromo-3-chlorobenzene (62.0 g, 324.1 mmol), Pd(PPh3)4 (15.6 g, 13.5 mmol), K2CO3 (93.3 g, 675.2 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0439] After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO4. Then, the solvent was removed from the resulting organic layer and then purified by column chromatography (Hexane: DCM = 9: 1 (v / v)) to obtain 1-(3-chlorophenyl)-9-phenyldibenzo[b, d]furan (68.0 g, 71% yield).

[0440] Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0441] Step 2: Synthesis of DBF-5

[0442]

[0443] Under nitrogen flow, 1-(3-chlorophenyl)-9-phenyldibenzo[b,d]furan (68.0 g, 191.8 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (53.6 g, 210.9 mmol), Pd(dppf)Cl2 (16.8 g, 19.2 mmol), KOAc (54.2 g, 575.3 mmol) and 1,4-dioxane (1000 ml) obtained in the above step 1 were mixed and stirred at 130°C for 12 hours.

[0444] After the reaction was completed, it was extracted with ethyl acetate, and then MgSO4 was used to remove moisture, and purified by column chromatography (Hexane: DCM = 4: 1 (v / v)) to obtain DBF-5 (41.9 g, yield 49%).

[0445] Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0446] Synthesis Example 29: Synthesis of E-1

[0447]

[0448] Under a nitrogen flow, DBF-1 (10.0 g, 22.4 mmol) obtained in Preparation Example 6, 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (9.6 g, 26.9 mmol), Pd(PPh3)4 (1.3 g, 1.1 mmol), K2CO3 (7.7 g, 56.0 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0449] After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO4. Then, the solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to obtain E-1 (11.8 g, yield 82%) as the target compound.

[0450] Mass (theoretical value: 641.73, measured value: 641 g / mol)

[0451] Synthesis Example 30: Synthesis of E-2

[0452]

[0453] The same process as in Synthesis Example 29 was carried out except that 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.9 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine used in Synthesis Example 29 to obtain E-2 (11.9 g, yield 74%) as the target compound.

[0454] Mass (theoretical value: 717.83, measured value: 717 g / mol)

[0455] Synthesis Example 31: Synthesis of E-3

[0456]

[0457] The same process as in Synthesis Example 29 was carried out except that 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (12.9 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine used in Synthesis Example 29 to obtain E-3 (11.4 g, yield 71%) as the target compound.

[0458] Mass (theoretical value: 717.83, measured value: 717 g / mol)

[0459] Synthesis Example 32: Synthesis of E-4

[0460]

[0461] The same process as in Synthesis Example 29 was carried out except that 2-(4-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.9 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine used in Synthesis Example 29 to obtain the target compound E-4 (12.7 g, yield 79%).

[0462] Mass (theoretical value: 717.83, measured value: 717 g / mol)

[0463] Synthesis Example 33: Synthesis of E-5

[0464]

[0465] The reaction mixture was prepared by mixing the DBF-4 (10.0 g, 22.4 mmol) obtained in Preparation Example 9 instead of DBF-1 (10.0 g, 22.4 mmol) used in Synthesis Example 29 and using 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine. The same process as in Synthesis Example 29 was carried out, except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.9 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine, to obtain the target compound E-5 (9.8 g, yield: 61%).

[0466] Mass (theoretical value: 717.83, measured value: 717 g / mol)

[0467] Synthesis Example 34: Synthesis of E-6

[0468]

[0469] The same process as in Synthesis Example 29 was carried out except that 2-([1,1':3',1"-terphenyl]-5'-yl)-4-chloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (2-([1,1':3',1"-terphenyl]-5'-yl)-4-chloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (13.7 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine used in Synthesis Example 29 to obtain the target compound E-6 (9.6 g, yield 54%).

[0470] Mass (theoretical value: 793.93, measured value: 793 g / mol)

[0471] Synthesis Example 35: Synthesis of E-7

[0472]

[0473] The reaction mixture was prepared by mixing the DBF-4 (10.0 g, 22.4 mmol) obtained in Preparation Example 9 instead of DBF-1 (10.0 g, 22.4 mmol) used in Synthesis Example 29 and using 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5 -triazine) (12.5 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine, and the same process as in Synthesis Example 29 was carried out to obtain the target compound E-7 (9.8 g, yield 62%).

[0474] Mass (theoretical value: 703.85, measured value: 703 g / mol)

[0475] Synthesis Example 36: Synthesis of E-8

[0476]

[0477] The reaction mixture was prepared by mixing the DBF-3 (10.0 g, 22.4 mmol) obtained in Preparation Example 8 instead of DBF-1 (10.0 g, 22.4 mmol) used in Synthesis Example 29 and using 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine. The same process as in Synthesis Example 29 was carried out, except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.9 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine, to obtain the target compound E-8 (10.8 g, yield 67%).

[0478] Mass (theoretical value: 717.83, measured value: 717 g / mol)

[0479] Synthesis Example 37: Synthesis of E-9

[0480]

[0481] The reaction mixture was prepared by mixing the DBF-3 (10.0 g, 22.4 mmol) obtained in Preparation Example 8 instead of DBF-1 (10.0 g, 22.4 mmol) used in Synthesis Example 29 and using 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine. The same process as in Synthesis Example 29 was carried out, except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.5 g, 26.9 mmol), to obtain the target compound E-9 (11.4 g, yield: 72%).

[0482] Mass (theoretical value: 703.85, measured value: 703 g / mol)

[0483] Synthesis Example 38: Synthesis of E-10

[0484]

[0485] The reaction mixture was prepared by mixing the DBF-5 (10.0 g, 22.4 mmol) obtained in Preparation Example 10 instead of DBF-1 (10.0 g, 22.4 mmol) used in Synthesis Example 29 and using 2-([1,1'-biphenyl]-3-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (2-([1,1'-biphenyl]-3-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine) as the reaction mixture. The same process as in Synthesis Example 29 was carried out, except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.5 g, 26.9 mmol), to obtain the target compound E-10 (10.4 g, 66% yield).

[0486] Mass (theoretical value: 703.85, measured value: 703 g / mol)

[0487] Example 1: Preparation of green organic EL device

[0488] The compound A-1 with hole characteristics and the compound E-1 with electronic characteristics are uniformly mixed in a weight ratio of 6:4, and then completely dissolved in tetrahydrofuran (THF) and stirred for 1 day. After stirring, the mixed solvent is spray-dried to remove the solvent to obtain a homogeneous organic complex HOC-1, and then a green organic EL device is prepared according to the following process. In this case, the above-mentioned compound A-1 is the first organic compound with hole characteristics synthesized in Synthesis Example 1, and the above-mentioned compound E-1 is the second organic compound with electronic characteristics synthesized in Synthesis Example 29. And, the above-mentioned weight ratio is an example of a weight ratio showing excellent performance, and is not limited thereto.

[0489] First, use distilled water to ultrasonically clean the After washing with distilled water, ultrasonic cleaning with isopropyl alcohol, acetone, methanol and other solvents and drying, the substrate was transferred to a UV-ozone (OZONE) cleaning machine (Power sonic405, HWASHIN TECH), and then the substrate was cleaned with UV for 5 minutes and transferred to a vacuum evaporation machine.

[0490] On the ITO transparent electrode prepared as above, the homogeneous organic complex HOC-1+10% Ir(ppy)3(300nm) / BCP(10nm) / Alq3(30nm) / LiF(1nm) / Al(200nm) was stacked in sequence to prepare an organic EL device.

[0491] The structures of m-MTDATA, TCTA, Ir(ppy)3, CBP and BCP are as follows.

[0492]

[0493] Examples 2 to 280: Preparation of green organic EL devices

[0494] A green organic EL device was prepared in the same manner as in Example 1, except that the homogeneous organic composites HOC-2 to HOC-280 were used instead of the homogeneous organic composite HOC-1 as the light-emitting host substance when forming the light-emitting layer.

[0495] Comparative Example 1: Preparation of green organic EL device

[0496] A green organic EL device was prepared in the same manner as in Example 1 except that comA, which was obtained by grinding and simply mixing Compound A-1 and Compound E-1 with a grinder, was used instead of the homogeneous organic complex HOC-1 as the light-emitting host substance in forming the light-emitting layer.

[0497] Evaluation Example 1: Spectroscopic Physical Properties

[0498] The maximum emission wavelengths of the homogeneous organic composites HOC-1 to HOC-280 prepared in Examples 1 to 280 were measured, respectively, and the results are shown in Table 1. In this case, the maximum emission wavelengths of the compounds A-1 to D-4 and E-1 to E-10 as the respective raw materials were measured, and the maximum emission wavelength of the simple mixture comA of Comparative Example 1 was measured as a control group.

[0499] Table 1

[0500]

[0501]

[0502]

[0503]

[0504]

[0505]

[0506]

[0507]

[0508]

[0509]

[0510]

[0511] As shown in Table 1 above, it was confirmed that the homogeneous organic composite HOC-1 of the present invention prepared in Example 1 exhibited the characteristic of maximum emission wavelength in a relatively long wavelength region compared to compound A-1, compound E-1, and a simple mixture comA of compound A-1 and compound E-1 (Comparative Example 1). This proves that the homogeneous organic composite of the present invention forms an electrically more stable composite. Similarly, it can be seen that the homogeneous organic composites HOC-2 to HOC-280 of Examples 2 to 280 of the present invention also exhibit the characteristic of maximum emission wavelength in a relatively long wavelength region compared to each raw material compound.

[0512] Evaluation Example 2: Evaluation of physical properties of organic EL devices

[0513] The green organic EL devices prepared in Examples 1 to 280 and Comparative Example 1 were measured at 10 mA / cm 2 Driving voltage, current efficiency and life at current density T 97 The results are shown in Table 2 below.

[0514] Table 2

[0515]

[0516]

[0517]

[0518]

[0519]

[0520]

[0521]

[0522]

[0523]

[0524]

[0525]

[0526]

[0527] As shown in Table 2, it can be seen that Examples 1 to 280 using the homogeneous organic composites HOC-1 to HOC-280 of the present invention as the light-emitting layer of the green organic EL device show significantly superior performance in terms of efficiency, driving voltage, and lifespan compared to Comparative Example 1 using the simple mixture comA. In particular, it can be confirmed that the green organic EL device of Example 1 has an effect of reducing the driving voltage by about 50% and an effect of increasing the lifespan of the device by about 40 times or more compared to Comparative Example 1.

[0528] Evaluation Example 3: Thin film formation evaluation

[0529] Each of the green organic EL devices prepared in Examples 1 to 280 and Comparative Example 1 was thin-filmed by a continuous process. In this case, the change in weight ratio (content ratio) between the compounds before and after the thin-film process was measured, and the results are shown in Table 3 below.

[0530] Table 3

[0531]

[0532]

[0533]

[0534]

[0535]

[0536]

[0537]

[0538]

[0539]

[0540]

[0541]

[0542]

[0543]

[0544]

[0545]

[0546]

[0547]

[0548]

[0549]

[0550]

[0551]

[0552]

[0553]

[0554]

[0555]

[0556]

[0557]

[0558]

[0559]

[0560]

[0561]

[0562] As shown in Table 3 above, by forming a thin film on the light-emitting layer of a green organic EL device using the homogeneous organic composites HOC-1 to HOC-280 (Examples 1 to 280) of the present invention through a continuous process and measuring the changes over time, it can be confirmed that a uniform thin film can be reproducibly formed compared to the simple mixture comA (Comparative Example 1).

Claims

1. A homogeneous organic composite for an organic electroluminescent device, comprising at least two organic compounds, characterized in that: The homogeneous organic complex comprises a first organic compound and a second organic compound. The maximum emission wavelength of the homogeneous organic composite is different from the maximum emission wavelength of the first organic compound, the second organic compound, and a simple organic mixture of the first organic compound and the second organic compound.

2. The homogeneous organic composite according to claim 1, characterized in that The maximum emission wavelength of the homogeneous organic complex shifts to a wavelength region longer than the maximum emission wavelength of the first organic compound, the second organic compound, and a simple organic mixture of the first organic compound and the second organic compound.

3. The homogeneous organic composite according to claim 1, characterized in that It is solid at room temperature.

4. The homogeneous organic composite according to claim 1, characterized in that The homogeneous organic composite is formed by completely dissolving the first organic compound and the second organic compound in at least one organic solvent to form a homogeneous phase and then solidifying the dissolved organic compound.

5. The homogeneous organic composite according to claim 4, characterized in that The homogeneous organic composite is formed by press-molding the solidified homogeneous organic composite under non-heat treatment conditions.

6. The homogeneous organic composite according to claim 5, characterized in that The solidified homogeneous organic composite is in the form of powder or rod. The pressure-molded homogeneous organic composite is in the form of particles selected from the group consisting of polyhedrons, cylinders and spheres.

7. The homogeneous organic composite according to claim 1, characterized in that The first organic compound and the second organic compound are -6 The deposition temperature difference was between 0°C and 30°C at a pressure of 100 torr.

8. The homogeneous organic composite according to claim 1, characterized in that The mixing ratio of the first organic compound to the second organic compound is 1:99 to 99:1 by weight.

9. The homogeneous organic composite according to claim 1, characterized in that Contains no inorganic substances or dopants.

10. The homogeneous organic composite according to claim 1, characterized in that The first organic compound and the second organic compound are the same as or different from each other, and are independently selected from the group consisting of host materials, electron injection materials, electron transport materials, electron blocking materials, hole injection materials, hole transport materials, hole blocking materials and exciton blocking materials.

11. The homogeneous organic composite according to claim 1, characterized in that The first organic compound and the second organic compound are host materials.

12. The homogeneous organic compound according to claim 1, characterized in that The first organic compound is a compound having a higher hole property than the second organic compound. The second organic compound is a compound containing at least one electron-withdrawing group represented by the following chemical formula: In the above chemical formula, X1 to X8 and Y1 to Y5 are the same or different from each other and are each independently N or C(R), but the above monocyclic or polycyclic moiety contains at least one N, When there are multiple C(R)s, the multiple Rs are the same or different from each other and are independently selected from hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide and C6~C 60 or they can combine with adjacent groups to form a condensed ring, The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamine, alkylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide and arylamine groups of R can be independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide and C6~C 60 The substituents may be substituted with one or more substituents selected from the group consisting of an aromatic amine group and, in this case, when a plurality of the substituents are present, they may be the same as or different from each other.

13. The homogeneous organic compound according to claim 13, characterized in that The second organic compound is a compound containing at least one nitrogen-containing moiety represented by the following chemical formula:

14. An organic electroluminescent device, characterized in that: include: anode; A cathode, arranged opposite to the anode; At least one organic layer is disposed between the anode and the cathode, The at least one organic layer comprises the homogeneous organic composite according to any one of claims 1 to 13.

15. The organic electroluminescent device according to claim 14, characterized in that: The at least one organic layer is formed by depositing a homogeneous organic composite that is solid at room temperature.

16. A method for preparing a homogeneous organic composite according to claim 1, characterized in that: include: The first step is to completely dissolve two or more organic compounds in at least one organic solvent to form a homogeneous phase and then solidify; as well as The second step is to press-form the solidified homogeneous organic composite under non-heat treatment conditions.

17. The method for preparing a homogeneous organic composite according to claim 16, characterized in that: In the second step, at 20000kgf / cm 2 Up to 40000kgf / cm 2 Molded under pressure.

18. The method for preparing a homogeneous organic composite according to claim 16, characterized in that: The solidified homogeneous organic composite prepared in the first step is in the form of powder or rod. The homogeneous organic composite formed in the second step is in the form of particles selected from the group consisting of polyhedrons, cylinders and spheres.

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