Homogeneous organic composite for organic electroluminescence element, and organic electroluminescence element containing the same

Abstract

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

Description

Technical Field

[0001] The present invention relates to a homogeneous organic complex for an organic electroluminescence device and an organic electroluminescence device including the same. More specifically, the present invention relates to a homogeneous organic complex having a homogeneous composition at the molecular level without suffering from thermal damage, and an organic electroluminescence device having improved low voltage, high efficiency, and long life characteristics by including the same in one or more organic layers.

Background Art

[0002] In an organic electroluminescence device (hereinafter abbreviated as "organic EL device"), when a voltage is applied between two electrodes, holes are injected from the positive electrode and electrons are injected from the negative electrode into the organic layer. The injected holes and electrons meet to form an exciton, and light is emitted when this exciton returns to the ground state. At this time, the organic substances used as the organic layer are classified into a light-emitting substance, a hole injection substance, a hole transport substance, an electron transport substance, an electron injection substance, etc. according to their functions.

[0003] In order to improve the performance of such an organic EL device, particularly its life, efficiency, and driving voltage, an organic layer is formed of a number of organic compounds, for example, one or more host materials in which a dopant is dispersed. The organic layer is formed by evaporating a number of organic compounds respectively, but at this time, it is difficult to accurately control each organic compound at a desired evaporation rate, and there is a relative waste in terms of material utilization. Furthermore, when an organic compound is solidified into a powder form, there is a problem that it becomes charged with static electricity and is difficult to handle during evaporation.

[0004] Conventionally, a pre-mix manufacturing method of mixing a large number of organic substances and applying them to an organic layer, a pre-melting manufacturing method of separately heat-treating the above-mentioned organic substances, etc. have been carried out. However, a desired level of homogeneous composition cannot be obtained by the pre-mix manufacturing method, and thermal damage to the organic material occurs due to the heat treatment during pre-melting, resulting in a problem that the performance of the finally obtained device deteriorates.

Summary of the Invention

Problems to be Solved by the Invention

[0005] The present invention has been devised to solve the above-mentioned problems, and an object of the present invention is to ensure a more homogeneous mixing composition than the conventional pre-mix manufacturing method and to fundamentally prevent thermal damage caused by the conventional pre-melting manufacturing method, and to provide a novel mixed material for an organic layer.

[0006] Another object of the present invention is to provide an organic EL device that exhibits high efficiency, low voltage, and long life characteristics simultaneously by including the above-mentioned novel mixed material for an organic layer.

[0007] Other objects and advantages of the present invention will become more apparent from the following detailed description and claims.

Means for Solving the Problems

[0008] To achieve the above technical problems, the present invention provides a homogeneous organic complex containing at least two organic compounds, the homogeneous organic complex includes 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 wavelengths of the first organic compound, the second organic compound, and a simple organic mixture of the first organic compound and the second organic compound, and provides a homogeneous organic complex for an organic EL device.

[0009] In one embodiment of the present invention, the maximum emission wavelength of the homogeneous organic composite can be shifted to a longer wavelength region than the maximum emission wavelengths of the first organic compound, the second organic compound, and a simple organic mixture of the first organic compound and the second organic compound.

[0010] In one embodiment of the present invention, the homogeneous organic composite is solid at room temperature.

[0011] In one embodiment of the present invention, the homogeneous organic composite is 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 the resulting solution.

[0012] In one embodiment of the present invention, the homogeneous organic composite is formed by pressing and shaping the solidified homogeneous organic composite without performing heat treatment.

[0013] In one embodiment of the present invention, the solidified homogeneous organic composite is in powder form or stick form, and the pressed and shaped homogeneous organic composite is in pellet form selected from the group consisting of polyhedrons, cylinders, and spheres.

[0014] In one embodiment of the present invention, the first organic compound and the second organic compound have a vapor deposition temperature difference of 0 to 30 °C under a pressure of 10 -6 torr.

[0015] In one embodiment of the present invention, the mixing ratio of the first organic compound and the second organic compound is a weight ratio of 1:99 to 99:1.

[0016] In one embodiment of the present invention, the homogeneous organic composite does not contain inorganic substances and dopants.

[0017] In one embodiment of the present invention, the first organic compound and the second organic compound are the same as or different from each other, and each independently is 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.

[0018] In one embodiment of the present invention, the first organic compound and the second organic compound are host materials.

[0019] In one embodiment of the present invention, the first organic compound is a compound having higher hole injection and transport characteristics than the second organic compound, and the second organic compound is a compound having higher electron injection and transport characteristics than the first organic compound.

[0020] Further, the present invention provides an organic EL element including a positive electrode; a negative electrode disposed opposite to the positive electrode; and at least one organic layer disposed between the positive electrode and the negative electrode, wherein the at least one organic layer includes the above-described homogeneous organic composite.

[0021] In one embodiment of the present invention, the at least one organic layer is formed by vapor-depositing a homogeneous organic composite that is solid at room temperature.

[0022] Furthermore, the present invention provides a method for producing a homogeneous organic composite, including: 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 pressing and molding the solidified homogeneous organic composite without performing heat treatment.

Advantages of the Invention

[0023] According to one embodiment of the present invention, by forming a homogeneous organic composite in a predetermined organic solvent using at least two organic compounds that are vaporizable and / or sublimable, a more homogeneous mixing composition can be ensured than in the existing premix manufacturing method.

[0024] Moreover, according to the present invention, a solid homogeneous organic composite having a desired size and shape can be easily obtained without performing a separate heat treatment, thus fundamentally preventing thermal damage to the material by the conventional premelting manufacturing method.

[0025] Furthermore, according to the present invention, an organic EL element having high efficiency and long life can be obtained by simplifying and streamlining the manufacturing process, thereby making it possible to provide a display panel with improved performance and life.

[0026] The effects of the present invention are not limited to the content described above, and more diverse effects are included in this specification.

BEST MODE FOR CARRYING OUT THE INVENTION

[0027] Hereinafter, the present invention will be described in detail. The examples according to the present invention are provided to more fully explain the present invention to those having ordinary knowledge in the technical field. The examples described below can be variously modified and implemented, and the scope of the present invention is not limited by these examples. Throughout this specification, the same reference numerals refer to the same structures.

[0028] Unless otherwise defined, all terms (including technical and scientific terms) used in this specification have the meaning commonly understood by those having ordinary knowledge in the technical field to which the present invention pertains. Also, terms defined in commonly used dictionaries are not ideally or excessively interpreted unless otherwise specified.

[0029] Throughout this specification, unless otherwise specified, when a part "includes" a certain component, it means that it can further include other components, rather than excluding other components. Throughout this specification, "above" or "on" does not necessarily mean located above the target part with respect to the direction of gravity, and includes not only the case where it is located above or below the target part, but also the case where there are other parts in between. Also, in this specification, terms such as "first" and "second" are not used to indicate any order or importance, but are used to distinguish components.

[0030] <Homogeneous organic composite> An example of the present invention relates to a homogeneous organic composite containing at least two or more organic compounds that form an organic layer included in an organic EL element, and these are composed of at least two organic compounds that can be vaporized or sublimated.

[0031] Specifically, in the present invention, without performing pre-treatments such as separate heat treatment or mechanical mixing, a homogeneous organic composite having a homogeneous mixing composition at the molecular level is formed using the solubility parameter characteristics of at least two or more organic compounds and a predetermined organic solvent. Such a homogeneous organic composite can obtain a more homogeneous mixing composition than existing premix manufacturing methods, and can fundamentally prevent thermal damage to organic material by existing pre-melting manufacturing methods.

[0032] In particular, conventionally, one or more organic compounds are reacted with another reactant for forming a chemical bond (e.g., covalent bond, ionic bond, coordination bond) with the above compound, such as an ionic compound (e.g., Bronsted acid, halogen bonding substance), a proton donating compound and / or an electron-donating compound, etc. to form a complex. In such a case, since other substances (e.g., inorganic or organic-inorganic) other than the organic compounds contained in the organic EL element are essentially included, it affects the performance and stability of the organic EL element. Further, since it is necessary to perform another reactant for forming a chemical bond and its manufacturing process, there occur complexity in manufacturing, increase in cost, decrease in productivity, etc. On the contrary, in the present invention, after forming a fine and homogeneous composition at the molecular level by using the solubility characteristics of at least two organic compounds and an organic solvent without forming a chemical bond with the third compound, and then removing the organic solvent to form a homogeneous organic complex, substances that may adversely affect the performance of the element are not included in the final product, and simplification of the process, reduction in cost, and ensuring of mass productivity are possible.

[0033] Further, since the blending of the solid homogeneous organic complex having a desired size and shape can be freely performed, an organic EL element having high efficiency and long life can be provided by simplifying and streamlining the manufacturing process.

[0034] The homogeneous organic complex according to the present invention forms an organic complex in which at least two organic compounds have physical interactions, and thus has optical characteristics completely different from those of each single organic compound or a heterogeneous mixture in which these are simply mixed.

[0035] In one specific example, the homogeneous organic complex is at least two organic compounds that can be vaporized or sublimated, including a first organic compound and a second organic compound. The maximum emission wavelength of the homogeneous organic complex has physical properties different from those of 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. Here, a simple organic mixture means a simple mixture in which a plurality of compounds are mixed but do not form a complex.

[0036] Specifically, the homogeneous organic complex according to the present invention forms a complex in which electrical energy is more stable compared to the first organic compound, the second organic compound, and their simple mixture. Therefore, the maximum emission wavelength by photons also shifts to a relatively stable long-wavelength region. Thus, the maximum emission wavelength (λmax) of the homogeneous organic complex can shift to a longer wavelength region than the maximum emission wavelength of the first organic compound, the second organic compound, and a heterogeneous organic mixture in which the first organic compound and the second organic compound are simply mixed. Note that the long-wavelength shift value of the maximum emission wavelength of the homogeneous organic complex is not particularly limited.

[0037] In another specific example, the homogeneous organic complex may be solid at room temperature. For example, it can be a solid obtained by forming a homogeneous composition using the solubility characteristics of at least two organic compounds and an organic solvent and then removing the solvent.

[0038] As an example, the homogeneous organic complex is obtained by completely dissolving a first organic compound and a second organic compound in at least one organic solvent to form a homogeneous phase and then solidifying it. The shape of the homogeneous organic complex solidified in this way is not particularly limited and can be, for example, powdery or stick-shaped. The homogeneous organic complex in the form of a solid such as a lump may be physically pulverized using a mixer or the like as necessary.

[0039] In addition, since the homogeneous organic composite according to the present invention is solidified after molecules are mixed in an appropriate solvent, it is possible to fundamentally prevent the minimum heterogeneous composition caused by mixing solids or molecular groups in the existing premelting method. Further, since it is a mixing using a solvent, it is possible to mix without suffering thermal damage at a temperature much lower than that of the premelting method.

[0040] In order to produce such a homogeneous organic composite, it is useful to use at least one organic solvent having a solubility index similar to that of at least two organic compounds as substances to be mixed. The at least one organic solvent is not particularly limited as long as it can dissolve the first organic compound and the second organic compound to form a homogeneous phase. As an example, a normal organic solvent known in the art may be used alone, or a mixed solvent in which two or more are mixed may be used. Examples of the organic solvent that can be used include, but are not limited to, tetrahydrofuran, methylene chloride, ethyl acetate, acetone, dimethyl ether, benzene, toluene, 1,2-dichlorobenzene, monochlorobenzene, methanol, ethanol, isopropyl alcohol, and the like. The mixing ratio of the two solvents is not particularly limited, and as an example, it may be 1:99 to 99:1. Such a molar ratio may be read as a weight ratio. In addition, an appropriate solvent can also be selected using two or more co-solvents.

[0041] As another example, the homogeneous organic composite is obtained by pressure molding the solidified homogeneous organic composite under conditions where heat treatment is not performed.

[0042] At this time, the pressure molding method is not particularly limited, and it can be carried out by a conventional method in the art. For example, 20,000 to 40,000 kgf / cm 2It may be injection-molded under the pressure. The shape of the homogeneous organic composite thus pressure-molded is not particularly limited and may be, for example, a pellet shape selected from the group consisting of polyhedrons, cylinders, and spheres. Additionally, it can be freely deformed into a solid having a desired shape and / or size.

[0043] There are no particular restrictions on the at least two organic compounds constituting the homogeneous organic composite of the present invention, and any can be used without particular limitation as long as it can be used as an organic layer material for an organic EL element through vaporization and / or sublimation in the art.

[0044] Such a homogeneous organic composite will form a homogeneous thin film of at least one organic layer contained in the organic EL element by a known vapor deposition method in the art. Thus, it is preferable that the first organic compound and the second organic compound constituting the homogeneous organic composite have deposition temperatures that are as similar to each other as possible. As an example, the first organic compound and the second organic compound preferably have a deposition temperature difference of 0 to 30 °C under a pressure of 10 -6 torr.

[0045] Also, the first organic compound and the second organic compound may be the same as or different from each other, and each independently may be 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, and more specifically, may contain at least two organic hosts and do not contain inorganic substances and dopants.

[0046] In the present invention, by mixing at least two organic compounds constituting a homogeneous organic composite, a compound with high electron characteristics and a compound with high hole characteristics, it is possible to improve the mobility of electrons and holes. For example, the first organic compound may be a compound with relatively strong hole characteristics, and the second organic compound may be a compound with relatively strong electron characteristics. Thus, a homogeneous organic composite composed of the first organic compound with relatively strong hole characteristics and the second organic compound with relatively strong electron characteristics has bipolar characteristics, and thereby, compared with the case where the first organic compound or the second organic compound is used alone, the mobility of both electrons and holes is increased, and the luminous efficiency can be significantly improved.

[0047] In an element in which a material having characteristics biased toward either electron characteristics or hole characteristics is introduced into the light-emitting layer, while carrier recombination occurs at the interface between the light-emitting layer and the electron or hole transport layer, relatively many excitons are formed, resulting in a decrease in the efficiency and lifetime characteristics of the light-emitting layer. On the contrary, in the present invention, a homogeneous organic composite composed of the first organic compound and the second organic compound is introduced as an organic layer material in the element, for example, as a light-emitting layer material, to produce an element in which a good carrier balance in the light-emitting layer is obtained, thereby exerting the effect of improving the luminous efficiency and lifetime characteristics.

[0048] The first organic compound that can be used in the present invention is not particularly limited as long as it is a compound having higher hole transport characteristics than the second organic compound, that is, a hole-transporting organic compound. The hole-transporting organic compound may be a hole-transporting host. As an example, the hole-transporting host may be a carbazole-based compound.

[0049] Specifically, examples of the hole-transporting organic compound include, but are not limited to, the compound represented by the following [Chemical Formula 1].

Chemical Formula

[0050] In the compound represented by the above [Chemical Formula 1], a, d, and f are each an integer of 0 to 3, and b, c, and e are each an integer of 0 to 4. Here, when a, b, c, d, e, and f are each 0, it means that hydrogen is not substituted with deuterium (D). On the other hand, when a, d, and f are each an integer of 1 to 3, and when b, c, and e are each an integer of 1 to 4, it means that one or more hydrogens are substituted with deuterium (D). At this time, 13 ≦ a + b + c + d + e + f ≦ 21 can be satisfied. As an example, the number of deuteriums (D) contained in the compound represented by the above [Chemical Formula 1] is at least 13, specifically at least 21. Such a compound represented by [Chemical Formula 1] can enhance the stability of the chemical structure by substitution with deuterium (D), and can simultaneously realize characteristics of the organic EL element, such as low voltage, high efficiency, and long life characteristics of the element.

[0051] Such deuterium may be substituted with other substituents (R). At this time, when there are a plurality of other substituents (R), they may be the same as or different from each other. Examples of the other substituents (R) include a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40an alkynyl group, C3-C 40 a cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, C6-C 60 an aryl group, a heteroaryl group having 5 to 60 ring atoms, C1-C 40 an alkyloxy group, C6-C 60 an aryloxy group, C1-C 40 an alkylsilyl group, C6-C 60 an arylsilyl group, C1-C 40 an alkylboron group, C6-C 60 an arylboron group, a phosphine oxide group, C1-C 40 an alkylphosphine oxide group, C6-C 60 an arylphosphine group, C6-C 60 an arylphosphine oxide group, and C6-C 60 an arylamine group, and may be selected from the group consisting of

[0052] In the compound represented by the above [Chemical Formula 1], Ar1 and Ar2 are the same as or different from each other, and each independently is hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, C1-C 40 an alkyl group, C2-C 40 an alkenyl group, C2-C 40 an alkynyl group, C3-C 40 a cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, C6-C 60 an aryl group, a heteroaryl group having 5 to 60 ring atoms, C1-C 40 an alkyloxy group, C6-C 60 an aryloxy group, C1-C 40 an alkylsilyl group, C6-C 60 an arylsilyl group, C1-C 40 an alkylboron group, C6-C 60 an arylboron group, a phosphine oxide group, C1-C 40 an alkylphosphine oxide group, C6-C 60 an arylphosphine group, C6-C 60 an arylphosphine oxide group, and C6-C 60Selected from arylamine groups, or these may form a condensed ring with adjacent groups. Specifically, Ar1 and Ar2 are the same as or different from each other and are each independently selected from the group consisting of an aryl group having 6 to C 60 and a heteroaryl group having 5 to 60 nuclear atoms.

[0053] As an example, Ar1 and Ar2 described above may be the same as or different from each other and may each independently be a substituent selected from the group consisting of the following substituents S1 to S4.

Chemical formula

[0054] With such Ar1 and Ar2, the compound represented by the above [Chemical formula 1] may be the compound represented by the following [Chemical formula 2], but is not limited thereto.

Chemical formula

[0055] Note that the compound represented by the above [Chemical formula 1] can have various structures depending on the bonding positions of the respective carbazole-based moieties. As an example, the compound represented by the above [Chemical formula 1] may be the compound represented by the following [Chemical formula 3].

Chemical formula

[0056] The compound represented by [Chemical Formula 1] according to the present invention as described above can be embodied in the following compounds, for example, Compounds A-1 to D4, but is not limited to these examples.

Chemical formula

Chemical formula

[0057] As the second organic compound that can be used in the present invention, there is no particular limitation as long as it is a compound having relatively high electron transport characteristics compared to the first organic compound, that is, an electron transporting organic compound.

[0058] The above electron transporting organic compound can be an electron transporting host. As an example, the above electron transporting host can be a compound containing at least one electron withdrawing group (EWG) represented by the following formula.

Chemical formula

[0059] When there are a plurality of the above C(R), the plurality of Rs are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C1 to C 40 alkyl group, a C2 to C 40 alkenyl group, a C2 to C 40 alkynyl group, a C3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1 to C 40 alkyloxy group, a C6 to C 60 aryloxy group, a C1 to C 40 alkylsilyl group, a C6 to C 60 arylsilyl group, a C1 to C40 An alkylboron group, C6-C 60 An arylboron group, C6-C 60 An arylphosphine group, C6-C 60 An arylphosphine oxide group, and C6-C 60 Selected from the group consisting of an arylamine group, or these may form a condensed ring with an adjacent group, The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group of the above R are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1-C 40 An alkyl group of, C2-C 40 An alkenyl group of, C2-C 40 An alkynyl group of, C2-C 40 A cycloalkyl group of, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6-C 60 An aryl group of, a heteroaryl group having 5 to 60 nuclear atoms, C1-C 40 An alkyloxy group of, C6-C 60 An aryloxy group of, C1-C 40 An alkylsilyl group of, C6-C 60 An arylsilyl group of, C1-C 40 An alkylboron group of, C6-C 60 An arylboron group of, C6-C 60 An arylphosphine group of, C6-C 60 An arylphosphine oxide group of, and C6-C 60 Selected from the group consisting of an arylamine group and may be substituted with one or more substituents, and when there are a plurality of the above substituents, these may be the same as or different from each other.

[0060] In one specific example, the second organic compound can be an azine compound containing at least one nitrogen-containing moiety represented by the following formula. As an example, it can be an electron-transporting host containing at least one moiety among triazine, pyrimidine, quinoline, quinazoline, and / or pyridine.

Chemical formula

[0061] Specifically, examples of the electron-transporting organic compound include, but are not limited to, the compound represented by the following [Chemical formula 4].

Chemical formula

[0062] In the compound represented by the above [Chemical Formula 4], Y1 and Y2 are the same as or different from each other, and each independently is N or C(Ar8), provided that at least one of Y1 and Y2 is N.

[0063] With such Y1 and Y2, in the compound represented by the above [Chemical Formula 4],

Chemical Structure

Chemical Structure

[0064] In the compound represented by the above [Chemical Formula 4], n1 is an integer from 1 to 5, and n2 is 0 or 1. As an example, n1 is 1 or 2, and n2 is 0 or 1. However, in the above [Chemical Formula 4], when n2 is 0, j is 1.

[0065] In the compound represented by the above [Chemical Formula 4], X1 may be selected from the group consisting of O, S, Se, N(Ar3), C(Ar4)(Ar5), and Si(Ar6)(Ar7). With such X1, examples of the dibenzo moiety include a monovalent dibenzofuran group, a monovalent dibenzothiophene group, and a monovalent fluorene group.

[0066] Ar3 to Ar8 are the same as or different from each other, and each independently is hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40 alkynyl group, a C3-C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6-C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1-C 40 alkyloxy group, a C6-C 40 aryloxy group, a C1-C 40 alkylsilyl group, a C6-C 60 arylsilyl group, a C1-C 40 alkylboron group, a C6-C 60 arylboron group, a phosphine oxide group, a C1-C 40 alkylphosphine oxide group, a C6-C 60 arylphosphine group, a C6-C 60 arylphosphine oxide group, and a C6-C 60 arylamine group, or these may form a condensed ring with adjacent groups (for example, Ar3-R1, Ar3-R2, Ar4-Ar5, Ar6-Ar7, Ar4-R1, Ar4-R2, Ar6-R1, Ar6-R2, etc.). Specifically, Ar3 to Ar8 are the same as or different from each other, and each independently is a C1-C 40 alkyl group, a C6-C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, or these may form a condensed ring with adjacent groups (for example, Ar3-R1, Ar3-R2, Ar4-Ar5, Ar6-Ar7, Ar4-R1, Ar4-R2, Ar6-R1, Ar6-R2, etc.). Here, the above condensed ring is a C3-C 60 condensed aliphatic ring (specifically, a C3-C 30 condensed aliphatic ring), a C6-C 60 condensed aromatic ring (specifically, a C6-C 30condensed aromatic ring), a 5- to 60-membered condensed heteroaromatic ring (specifically, a 5- to 30-membered condensed heteroaromatic ring), a C3-C 60 spiro ring, and one or more selected from the group consisting of combinations thereof may be used.

[0067] As an example, in the above [Chemical Formula 4],

Chem.

Chem.

Chem.

[0068] In the compound represented by the above [Chemical Formula 4], h is an integer from 0 to 3, g and i are each an integer from 0 to 4, and j and k are each an integer from 0 to 5. Here, when g, h, i, j, and k are each 0, it means that hydrogen is not substituted for R1 to R5 which are substituents. On the other hand, when h is an integer from 1 to 3, when g and i are each an integer from 1 to 4, and when j and k are each an integer from 1 to 5, one or more of R1 to R5 are the same as or different from each other and are each independently deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40 alkynyl group, a C3-C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6-C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1-C 40an alkyloxy group, C6 - C 60 an aryloxy group, C1 - C 40 an alkylsilyl group, C6 - C 60 an arylsilyl group, C1 - C 40 an alkylboron group, C6 - C 60 an arylboron group, a phosphine oxide group, C1 - C 40 an alkylphosphine oxide group, C6 - C 60 an arylphosphine group, C6 - C 60 an arylphosphine oxide group, and C6 - C 60 an arylamine group, and may be selected from the group consisting of, or these may form a condensed ring with adjacent groups. Specifically, one or more of R1 - R5 are the same as or different from each other, and each independently is hydrogen, a halogen group, a cyano group, a nitro group, an amino group, C1 - C 40 an alkyl group, C6 - C 60 an aryl group, and may be selected from the group consisting of a heteroaryl having 5 to 60 nuclear atoms.

[0069] The alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, alkylsilyl groups, arylsilyl groups, alkylboron groups, arylboron groups, alkylphosphine oxide groups, arylphosphine groups, arylphosphine oxide groups, arylamine groups, and condensed rings of the above Ar3 - Ar8 and R1 - R5 are each independently deuterium, a halogen, a cyano group, a nitro group, C2 - C 40 an alkenyl group, C2 - C 40 an alkynyl group, C3 - C 40 a cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C1 - C 40 an alkyl group, C6 - C 60 an aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C1 - C 40 an alkyloxy group, C6 - C 60 an aryloxy group, C1 - C 40 an alkylsilyl group, C6 - C 60 an arylsilyl group, C1 - C40 An alkyl boron group, C6 - C 60 An aryl boron group, C6 - C 60 An aryl phosphine group, C6 - C 60 An aryl phosphine oxide group, and C6 - C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl amine group of C6 - C, and when there are a plurality of the above substituents, they may be the same as or different from each other.

[0070] The compound represented by the above [Chemical Formula 4] can be a compound represented by the following [Chemical Formula 5], but is not limited thereto.

Chemical Structure

[0071] Specifically, the compound represented by the above [Chemical Formula 4] can be a compound represented by the following [Chemical Formula 6] or [Chemical Formula 7], but is not limited thereto.

[0072]

Chemical Structure

Chemical Structure

[0073] More specifically, the compound represented by the above [Chemical Formula 4] can be a compound represented by the following [Chemical Formula 8] or [Chemical Formula 9], but is not limited thereto.

Chemical Structure

Chemical Structure

[0074] The compound represented by [Chemical Formula 2] according to the present invention as described above can be embodied in the following compounds, for example, Compounds E-1 to E10, but is not limited to these examples.

Chemical Structure

[0075] In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

[0076] In the present invention, "alkenyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

[0077] In the present invention, "alkynyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

[0078] In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples thereof include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, etc.

[0079] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 ring atoms, and one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S or Se. Examples thereof include, but are not limited to, morpholine, piperazine, etc.

[0080] In the present invention, "aryl" means a monovalent substituent derived from a monocyclic or aromatic hydrocarbon having 6 to 60 carbon atoms in which two or more rings are combined. Note that two or more rings may be in a pendant or fused form. Examples thereof include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, etc.

[0081] In the present invention, "heteroaryl" means a monovalent substituent derived from a monocyclic or polycyclic heteroaromatic hydrocarbon having 5 to 60 ring atoms. At this time, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S or Se. Note that two or more rings may be in a pendant or fused form, and thus may be in a form of fusion with an aryl group. Examples thereof include, but are not limited to, 6-membered monocyclic rings such as pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, etc.

[0082] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O—, where R' means an alkyl having 1 to 40 carbon atoms. Such alkyloxy may have a linear, branched, or cyclic structure. Examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

[0083] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO—, where R means an aryl having 5 to 40 carbon atoms. Examples thereof include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

[0084] In the present invention, "alkylsilyl" means silyl substituted with an alkyl having 1 to 40 carbon atoms, and includes not only mono-, but also di- and tri-alkylsilyl. Further, "arylsilyl" means silyl substituted with an aryl having 5 to 60 carbon atoms, and includes not only mono-, but also polyarylsilyl such as di- and tri-arylsilyl.

[0085] In the present invention, "alkylboron" means boron substituted with an alkyl having 1 to 40 carbon atoms, and "arylboron" means boron substituted with an aryl having 6 to 60 carbon atoms.

[0086] In the present invention, "alkylphosphinyl group" means a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes not only mono-, but also di-alkylphosphinyl group. Further, in the present invention, "arylphosphinyl group" means a phosphine group substituted with a monoaryl or diaryl having 6 to 60 carbon atoms, and includes not only mono-, but also di-arylphosphinyl group.

[0087] In the present invention, "arylamine" means an amine substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono-, but also di-arylamine.

[0088] In the present invention, "heteroarylamine" means an amine substituted with a heteroaryl having 5 to 60 ring atoms, and includes not only mono-heteroarylamine but also di-heteroarylamine. In the present invention, (aryl)(heteroaryl)amine means an amine substituted with an aryl having 6 to 60 carbon atoms and a heteroaryl having 5 to 60 ring atoms.

[0089] In the present invention, "condensed ring" means a condensed aliphatic ring having 3 to 40 carbon atoms, a condensed aromatic ring having 6 to 60 carbon atoms, a condensed heteroaliphatic ring having 3 to 60 ring atoms, a condensed heteroaromatic ring having 5 to 60 ring atoms, a spiro ring having 3 to 60 carbon atoms, or a combination thereof.

[0090] In the homogeneous organic composite according to the present invention, the mixing ratio of the first organic compound and the second organic compound is, for example, a weight ratio of 1:99 to 99:1. As an example, the first organic compound and the second organic compound may be included in a weight ratio of 20:80 to 80:20. Within the above-described range, bipolar characteristics can be more effectively realized, and the efficiency and lifetime characteristics of the device can be improved simultaneously. The above-described weight ratio may be read as a molar ratio.

[0091] The homogeneous organic composite can be used as at least one organic material included in an organic EL device, and may be used, for example, as a light-emitting material, a light-absorbing material, a charge-transporting material, a charge-injecting material, a charge-blocking material, or a combination thereof. Specifically, the homogeneous organic composite may be used as a light-emitting material, and more specifically, may be used as a host.

[0092] Note that the homogeneous organic composite according to the present invention can be produced using the solubility characteristics of at least two organic compounds and an organic solvent.

[0093] In one embodiment of manufacturing the above-mentioned homogeneous organic composite, after completely dissolving two or more vaporizable or sublimable organic compounds in at least one organic solvent to form a homogeneous phase, a first step of solidifying is carried out, and the solidified homogeneous organic composite can be manufactured through a second step of pressurizing and molding it under conditions without heat treatment.

[0094] At this time, the molding conditions in the second step are not particularly limited. For example, injection molding may be carried out under a pressure of 20,000 to 40,000 kgf / cm 2 .

[0095] Also, the solidified homogeneous organic composite obtained in the first step is in powder form or stick form, and the homogeneous organic composite molded in the second step is in a pellet shape selected from the group consisting of polyhedrons, cylinders, and spheres, but is not limited thereto.

[0096] In addition, regarding each component constituting the homogeneous organic composite according to the present invention, since it is the same as described above, duplicate explanations are omitted.

[0097] The pellet-shaped homogeneous organic composite manufactured as described above is deposited by a conventional vacuum evaporation method (evaporation), sputtering method, etc. known in the art and will be included as any one of at least one organic layer in an organic EL element.

[0098] <Organic EL element> Another example of the present invention relates to an organic EL element including the homogeneous organic composite of the present invention as described above as at least one organic layer material.

[0099] Specifically, it is an organic EL element including a positive electrode (anode), a negative electrode (cathode), and one or more organic layers interposed between the positive electrode and the negative electrode, and at least one of the one or more organic layers includes a homogeneous thin film formed of a homogeneous organic composite.

[0100] The above-mentioned organic layer(s) of one or more layers is / are any one or more of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a lifetime improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer. Specifically, the organic layer containing the above homogeneous organic composite may be a light-emitting layer.

[0101] At this time, the above first organic compound may be a hole-transporting host, and the above second organic compound may be an electron-transporting host. The mixing ratio of such a first organic compound and a second organic compound is not particularly limited. For example, it is a weight ratio of 1:99 to 99:1, and preferably a weight ratio of 20:80 to 80:20.

[0102] In addition to the above-mentioned first organic compound and second organic compound, the above light-emitting layer may further contain a host and / or a dopant well-known in the art. At this time, the total content of the above first organic compound and second organic compound is 0 to 100% by weight based on the total amount of the host.

[0103] Further, the total amount of the host is about 70 to 99.9% by weight based on the total amount of the light-emitting layer, and the content of the dopant is about 0.1 to 30% by weight based on the total amount of the light-emitting layer.

[0104] The structure of such an organic EL element of the present invention is not particularly limited, but may be a structure in which a substrate, a positive electrode, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and a negative electrode are sequentially laminated. At this time, one or more of the above hole injection layer, hole transport layer, light-emitting auxiliary layer, light-emitting layer, electron transport layer, and electron injection layer contain the above homogeneous organic composite, and it is preferable that the light-emitting layer contains a homogeneous organic mixture. Note that an electron injection layer may be further laminated on the above electron transport layer.

[0105] The structure of the organic EL element according to 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.

[0106] The organic EL element according to the present invention can be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that one or more of the above-described organic material layers contain the above homogeneous organic composite.

[0107] The above organic material layer can be formed by a dry film formation method such as a vacuum evaporation method, a sputtering method, a plasma plating method, an ion plating method, etc., but is not limited thereto.

[0108] The substrate used in the manufacture of the organic EL element according to the present invention is not particularly limited, and examples thereof include a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet.

[0109] Also, as the positive electrode material, a positive electrode substance known in the art can be used without limitation. For example, metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, etc., but are not limited thereto.

[0110] Also, as the negative electrode material, a negative electrode substance known in the art can be used without limitation. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; and multilayer structured substances such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0111] Also, the hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer are not particularly limited, and can be formed using substances known in the art without limitation.

Example

[0112] Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by these examples.

[0113] <Preparation Example 1-1> Synthesis of Cz-D1

Chemical formula

[0114] After completion of the reaction, the mixture was extracted with ethyl acetate, then the water was removed with MgSO4, and purified by column chromatography (hexane:EA = 5:1 (v / v)) to obtain Cz-D1 (125.7 g, yield 72%). Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0115] <Preparation Example 1-2> Synthesis of Cz-D2

Chemical formula

[0116] <Preparation Example 1-3> Synthesis of Cz-D3

Chemical formula

[0117] <Preparation Example 1-4>Synthesis of Cz-D4

Chemical formula

[0118] <Preparation Example 2-1>Synthesis of Cz-D5

Chemical formula

[0119] <Preparation Example 2-2>Synthesis of Cz-D6

Chemical formula

[0120] <Preparation Example 2-3> Synthesis of Cz-D7

Chem.

[0121] <Preparation Example 2-4> Synthesis of Cz-D8

Chem.

[0122] <Preparation Example 3-1> Synthesis of Cz-D9

Chem.

[0123] <Preparation Example 3-2> Synthesis of Cz-D10

Chem.

[0124] <Preparation Example 3-3> Synthesis of Cz-D11

Chemical formula

[0125] <Preparation Example 3-4> Synthesis of Cz-D12

Chemical formula

[0126] <Preparation Example 4-1> Synthesis of Cz-D13

Chemical formula

[0127] <Preparation Example 4-2> Synthesis of Cz-D14

Chemical formula

[0128] <Preparation Example 4-3> Synthesis of Cz-D15

Chemical formula

[0129] <Preparation Example 4-4> Synthesis of Cz-D16

Chemical formula

[0130] <Preparation Example 5-1> Synthesis of BCz-D1 <Step 1> Synthesis of 9-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7

Chemical formula

[0131] After completion of the reaction, the mixture was extracted with ethyl acetate, the moisture was removed with MgSO4, 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 (96.0 g, yield 84%). Mass (Theoretical value: 376.3 g, Measured value: 376 g / mol)

[0132] <Step 2> Synthesis of BCz-D1

Chemical formula

[0133] After completion of the reaction, the mixture was extracted with methylene chloride, and filtered after adding MgSO4. After removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:EA = 7:1 (v / v)) to obtain BCz-D1 (71.1 g, yield 66%). Mass (theoretical value: 422.59 g, measured value: 422 g / mol)

[0134] <Preparation Example 5-2> Synthesis of BCz-D2

Chemical formula

[0135] <Preparation Example 5-3> Synthesis of BCz-D3

Chemical formula

[0136] <Preparation Example 5-4> Synthesis of BCz-D4

Chemical Formula

[0137] [Synthesis Example 1] Synthesis of A-1

Chemical Formula

[0138] [Synthesis Example 2] Synthesis of A-2

Chemical Formula

[0139] [Synthesis Example 3] Synthesis of A-3 [Chemical formula] Compound A-3 (13.2 g, yield 75%) was obtained in the same manner as in Synthesis Example 1, except that Cz-D3 (10.0 g, 23.6 mmol) obtained in Preparation Examples 1-3 was used instead of Cz-D1 used in Synthesis Example 1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0140] [Synthesis Example 4] Synthesis of A-4 [Chemical formula] Compound A-4 (12.2 g, yield 69%) was obtained in the same manner as in Synthesis Example 1, except that Cz-D4 (10.0 g, 23.6 mmol) obtained in Preparation Examples 1-4 was used instead of Cz-D1 used in Synthesis Example 1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0141] [Synthesis Example 5] Synthesis of A-5 [Chemical formula] Compound A-5 (8.73 g, yield 55%) was obtained in the same manner as in Synthesis Example 1, 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. Mass (theoretical value: 670.93, measured value: 670 g / mol)

[0142] [Synthesis Example 6] Synthesis of A-6 [Chemical formula] Compound A-6 (7.42 g, yield 42%) was obtained in the same manner as in Synthesis Example 1, 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. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0143] [Synthesis Example 7] Synthesis of A-7 [Chemical formula] Except for using Cz-D7 (10.0 g, 23.6 mmol) obtained in Preparation Example 2-3 instead of Cz-D1 used in Synthesis Example 1, the target compound A-7 (8.83 g, yield 50%) was obtained in the same manner as in Synthesis Example 1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0144] [Synthesis Example 8] Synthesis of A-8 [Chemical formula] Except for using Cz-D8 (10.0 g, 23.6 mmol) obtained in Preparation Example 2-4 instead of Cz-D1 used in Synthesis Example 1, the target compound A-8 (9.89 g, yield 56%) was obtained in the same manner as in Synthesis Example 1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0145] [Synthesis Example 9] Synthesis of A-9 [Chemical formula] Except for using Cz-D9 (9.3 g, 23.6 mmol) obtained in Preparation Example 3-1 instead of Cz-D1 used in Synthesis Example 1, the target compound A-9 (8.41 g, yield 53%) was obtained in the same manner as in Synthesis Example 1. Mass (theoretical value: 670.93, measured value: 670 g / mol)

[0146] [Synthesis Example 10] Synthesis of A-10 [Chemical formula] Instead of Cz-D1 used in Synthesis Example 1, A-10 (8.66 g, yield 49%), the target compound, was obtained in the same manner as in Synthesis Example 1, except that Cz-D10 (10.0 g, 23.6 mmol) obtained in Preparation Example 3-2 was used. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0147] [Synthesis Example 11] Synthesis of A-11

Chemical formula

[0148] [Synthesis Example 12] Synthesis of A-12

Chemical formula

[0149] [Synthesis Example 13] Synthesis of A-13

Chemical formula

[0150] [Synthesis Example 14] Synthesis of A-14 [Chemical formula] Instead of Cz-D1 used in Synthesis Example 1, Cz-D14 (10.0 g, 23.6 mmol) obtained in Preparation Example 4-2 was used, and in the same manner as in Synthesis Example 1, the target compound A-14 (10.78 g, yield 61%) was obtained. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0151] [Synthesis Example 15] Synthesis of A-15 [Chemical formula] Instead of Cz-D1 used in Synthesis Example 1, Cz-D15 (10.0 g, 23.6 mmol) obtained in Preparation Example 4-3 was used, and in the same manner as in Synthesis Example 1, the target compound A-15 (11.13 g, yield 63%) was obtained. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0152] [Synthesis Example 16] Synthesis of A-16 [Chemical formula] Instead of Cz-D1 used in Synthesis Example 1, Cz-D16 (10.0 g, 23.6 mmol) obtained in Preparation Example 4-4 was used, and in the same manner as in Synthesis Example 1, the target compound A-16 (9.02 g, yield 51%) was obtained. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0153] [Synthesis Example 17] Synthesis of B-1 [Chemical formula] Under a nitrogen stream, 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 completion of the reaction, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the target compound B-1 (10.2 g, yield 62%). Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0154] [Synthesis Example 18] Synthesis of B-2

Chemical formula

[0155] [Synthesis Example 19] Synthesis of B-3

Chemical formula

[0156] [Synthesis Example 20] Synthesis of B-4

Chemical formula

[0157] [Synthesis Example 21] Synthesis of C-1

Chemical formula

[0158] [Synthesis Example 22] Synthesis of C-2

Chemical formula

[0159] [Synthesis Example 23] Synthesis of C-3

Chemical formula

[0160] [Synthesis Example 24] Synthesis of C-4

Chemical Structure

[0161] [Synthesis Example 25] Synthesis of D-1

Chemical Structure

[0162] [Synthesis Example 26] Synthesis of D-2

Chemical Structure

[0163] [Synthesis Example 27] Synthesis of D-3

Chemical Structure

[0164] [Synthesis Example 28] Synthesis of D-4

Chemical Structure

[0165] [Preparation Example 6] Synthesis of DBF-1 [Step 1] Synthesis of 4-(3-chlorophenyl)-6-phenyldibenzothiophene

Chemical Structure

[0166] After completion of the reaction, the mixture was extracted with methylene chloride, filtered after adding MgSO4. Next, after removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:DCM = 9:1 (v / v)) to obtain 4-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan (48.9 g, yield 51%). Mass (theoretical value: 354.83 g, measured value: 354 g / mol)

[0167] <Step 2> Synthesis of DBF-1

Chemical formula

[0168] After completion of the reaction, the mixture was extracted with ethyl acetate, the water was removed with MgSO4, and it was purified by column chromatography (hexane:DCM = 4:1 (v / v)) to obtain DBF-1 (26.4 g, yield 43%). Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0169] [Preparation Example 7] Synthesis of DBF-2 <Step 1> Synthesis of 4-(4-chlorophenyl)-6-phenyldibenzothiophene

Chemical formula

[0170] After completion of the reaction, the mixture was extracted with methylene chloride, filtered after adding MgSO4. Next, after removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:DCM = 9:1 (v / v)) to obtain 4-(4-chlorophenyl)-6-phenyldibenzothiophene (60.4 g, yield 63%). Mass (theoretical value: 354.83 g, measured value: 354 g / mol)

[0171] <Step 2> Synthesis of DBF-2

Chemical formula

[0172] After the reaction was completed, the mixture was extracted with ethyl acetate, dried over MgSO4 to remove water, and purified by column chromatography (hexane:DCM = 4:1 (v / v)) to obtain DBF-2 (36.5 g, yield 48%). Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0173] [Preparation Example 8] Synthesis of DBF-3 [Step 1] Synthesis of 3-(3-chlorophenyl)-6-phenyldibenzothiophene [Chemical formula] Under a nitrogen stream, 4,4,5,5-tetramethyl-2-(6-phenyldibenzothiophen-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.

[0174] After the reaction was completed, the mixture was extracted with methylene chloride, filtered through MgSO4. Next, the solvent was removed from the obtained organic layer and purified by column chromatography (hexane:DCM = 9:1 (v / v)) to obtain 3-(3-chlorophenyl)-6-phenyldibenzothiophene (68.0 g, yield 71%). Mass (theoretical value: 354.83 g, measured value: 354 g / mol)

[0175] [Step 2] Synthesis of DBF-3 [Chemical formula] Under a nitrogen stream, 3-(3-chlorophenyl)-6-phenyldibenzothiophene (68.0 g, 191.8 mmol) obtained in the above <Step 1>, 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) were mixed and stirred at 130 °C for 12 hours.

[0176] After completion of the reaction, the mixture was extracted with ethyl acetate, the moisture was removed with MgSO4, and the residue was purified by column chromatography (hexane:DCM = 4:1 (v / v)) to obtain DBF-3 (54.8 g, yield 64%). Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0177] [Preparation Example 9] Synthesis of DBF-4 <Step 1> Synthesis of 1-(3-chlorophenyl)-6-phenyldibenzothiophene [Chemical formula] Under a nitrogen stream, 4,4,5,5-tetramethyl-2-(6-phenyldibenzothiophene-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.

[0178] After completion of the reaction, the mixture was extracted with methylene chloride, filtered after adding MgSO4. Next, the solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (hexane:DCM = 9:1 (v / v)) to obtain 1-(3-chlorophenyl)-6-phenyldibenzothiophene (62.3 g, yield 65%). Mass (theoretical value: 354.83 g, measured value: 354 g / mol)

[0179] <Step 2> Synthesis of DBF-4

Chem.

[0180] After completion of the reaction, the mixture was extracted with ethyl acetate, the moisture was removed with MgSO4, and purified by column chromatography (hexane:DCM = 4:1 (v / v)) to obtain DBF-4 (45.4 g, yield 58%). Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0181] [Preparation Example 10] Synthesis of DBF-5 <Step 1> Synthesis of 1-(3-chlorophenyl)-9-phenyldibenzothiophene

Chem.

[0182] After completion of the reaction, the mixture was extracted with methylene chloride, filtered after adding MgSO4. Next, after removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:DCM = 9:1 (v / v)) to obtain 1-(3-chlorophenyl)-9-phenyldibenzothiophene (68.0 g, yield 71%). Mass (theoretical value: 354.83 g, measured value: 354 g / mol)

[0183] <Step 2> Synthesis of DBF-5

Chemical formula

[0184] After completion of the reaction, the mixture was extracted with ethyl acetate, the moisture was removed with MgSO4, and it was purified by column chromatography (hexane:DCM = 4:1 (v / v)) to obtain DBF-5 (41.9 g, yield 49%). Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0185] [Preparation Example 29] Synthesis of E-1

Chemical formula

[0186] After completion of the reaction, extraction was performed with methylene chloride, and filtration was carried out after adding MgSO4. Next, after removing the solvent from the obtained organic layer, purification was performed by column chromatography (hexane:EA = 4:1 (v / v)) to obtain the target compound E-1 (11.8 g, yield 82%). Mass (theoretical value: 641.73, measured value: 641 g / mol)

[0187] [Synthesis Example 30] Synthesis of E-2

Chemical formula

[0188] [Synthesis Example 31] Synthesis of E-3

Chemical formula

[0189] [Synthesis Example 32] Synthesis of E-4

Chemical formula

[0190] [Synthesis Example 33] Synthesis of E-5

Chemical formula

[0191] [Synthesis Example 34] Synthesis of E-6

Chemical formula

[0192] [Synthesis Example 35] Synthesis of E-7

Chemical formula

[0193] [Synthesis Example 36] Synthesis of E-8

Chemical formula

[0194] [Synthesis Example 37] Synthesis of E-9

Chemical formula

[0195] [Synthesis Example 38] Synthesis of E-10

Chemical formula

[0196] [Example 1] Fabrication of Green Organic EL Device Compound A-1 having hole properties and compound E-1 having electron properties were uniformly mixed at a weight ratio of 6:4, completely dissolved in tetrahydrofuran (THF), and then stirred for 1 day. After completion of stirring, the mixed solvent was removed by a spray drying method to obtain a homogeneous organic composite HOC-1, and then a green organic EL device was fabricated according to the following procedure. At this time, the above compound A-1 is the first organic compound having hole properties synthesized in Synthesis Example 1, and the above compound E-1 is the second organic compound having electron properties synthesized in Synthesis Example 29. Also, the above weight ratio is an example of the weight ratio for obtaining excellent performance and is not limited thereto.

[0197] First, a glass substrate with a thin film coating of ITO (Indium Tin Oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After completion of washing with distilled water, ultrasonic washing was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a UV ozone washer (Power sonic 405, manufactured by Facsyntec Co., Ltd.), and then the substrate was washed with UV for 5 minutes and transferred to a vacuum evaporator.

[0198] On the thus-prepared ITO transparent electrode, an organic EL element was fabricated by laminating in the order of m-MTDATA (60 nm) / TCTA (80 nm) / homogeneous organic composite HOC-1 + 10% Ir(ppy)3 (300 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm).

[0199] The structures of m-MTDATA, TCTA, Ir(ppy)3, CBP, and BCP are as follows. [Chemical formula] [Chemical formula]

[0200] [Examples 2 to 280] Fabrication of green organic EL elements When forming the light-emitting layer, green organic EL elements were fabricated in the same manner as in Example 1 above, except that HOC-2 to HOC-280 were used instead of the homogeneous organic composite HOC-1 as the light-emitting host material.

[0201] [Comparative Example 1] Fabrication of green organic EL elements When forming the light-emitting layer, green organic EL elements were fabricated in the same manner as in Example 1 above, except that comA, which was simply mixed by grinding compound A-1 and compound E-1 with a grinder, was used instead of the homogeneous organic composite HOC-1 as the light-emitting host material.

[0202] [Evaluation Example 1: Spectroscopic physical properties] For the homogeneous organic composites HOC-1 to HOC-280 fabricated in Examples 1 to 280, the maximum emission wavelengths were measured respectively, and the results are shown in Table 1. At this time, the maximum emission wavelengths of compounds A-1 to D4 and compounds E-1 to E-10, which are the respective raw materials, were measured, and as a control group, the maximum emission wavelength of comA, which is a mixture simply mixed in Comparative Example 1, was measured.

[0203] [Table 1] JPEG2025518921000093.jpg 228170 JPEG2025518921000094.jpg 223170 JPEG2025518921000095.jpg 226170 JPEG2025518921000096.jpg 225170 JPEG2025518921000097.jpg 224170 JPEG2025518921000098.jpg 225170 JPEG2025518921000099.jpg 88170 As shown in Table 1 above, the homogeneous organic composite HOC-1 of the present invention produced in Example 1 shows the characteristics of the maximum emission wavelength in the relatively long wavelength region compared to comA (Comparative Example 1), which is a simple mixture of Compound A-1 and Compound E-1. It was confirmed that this proves that the homogeneous organic composite according to the present invention forms a more electrically stable composite. Similarly to the above, it was found that the homogeneous organic composites HOC-2 to HOC-280 according to Examples 2 to 280 of the present invention show the characteristics of the maximum emission wavelength in the relatively long wavelength region compared to the compounds of each raw material.

[0204] [Evaluation Example 2: Physical Property Evaluation of Organic EL Element] Regarding the green organic EL elements fabricated in Examples 1 to 280 and Comparative Example 1, the driving voltage, current efficiency, and lifetime T 2 at a current density of 10 mA / cm 97 were measured, and the results are shown in Table 2 below.

[0205]

Table 2

[0206] [Evaluation Example 3: Thin Film Formation Evaluation] For each of the green organic EL elements fabricated in Examples 1 to 280 and Comparative Example 1, a thin film was formed by a continuous process. At this time, the change in the weight ratio (content ratio) of each compound before and after the thin film process was measured, and the results are shown in Table 3 below.

[0207] [Table 3] JPEG2025518921000109.jpg220170JPEG2025518921000110.jpg213170JPEG2025518921000111.jpg209170JPEG2025518921000112.jpg219170JPEG2025518921000113.jpg213170JPEG2025518921000114.jpg220170JPEG2025518921000115.jpg221170JPEG2025518921000116.jpg219170JPEG2025518921000117.jpg217170JPEG2025518921000118.jpg215170JPEG2025518921000119.jpg216170JPEG2025518921000120.jpg217170JPEG2025518921000121.jpg211170JPEG2025518921000122.jpg210170JPEG2025518921000123.jpg215170JPEG2025518921000124.jpg211170JPEG2025518921000125.jpg214170JPEG2025518921000126.jpg215170JPEG2025518921000127.jpg214170JPEG2025518921000128.jpg212170JPEG2025518921000129.jpg212170JPEG2025518921000130.jpg210170JPEG2025518921000131.jpg113170

[0208] As shown in Table 3 above, by using the homogeneous organic composites HOC-1 to HOC-280 (Examples 1 to 280) according to the present invention as the light-emitting layer of the green organic EL element and performing a continuous process to form a thin film, and measuring the change over time, it was confirmed that a homogeneous thin film with good reproducibility can be formed as compared with comA (Comparative Example 1) which is a simple mixture.

Claims

1. A homogeneous organic composite containing at least two kinds of organic compounds, The homogeneous organic composite contains a first organic compound and a second organic compound, The maximum emission wavelength of the homogeneous organic composite is different from the maximum emission wavelengths of the first organic compound, the second organic compound, and a simple organic mixture of the first organic compound and the second organic compound, and is a homogeneous organic composite for an organic EL element.

2. The maximum emission wavelength of the homogeneous organic composite shifts to a longer wavelength region than the maximum emission wavelengths 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 homogeneous organic composite according to Claim 1.

3. The homogeneous organic composite according to Claim 1, which is solid at room temperature.

4. The homogeneous organic composite is 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 it. The homogeneous organic composite according to Claim 1.

5. The homogeneous organic composite is obtained by pressure molding the solidified homogeneous organic composite without performing heat treatment. The homogeneous organic composite according to Claim 4.

6. The solidified homogeneous organic composite is in powder form or stick form, The pressure-molded homogeneous organic composite is in a pellet shape selected from the group consisting of polyhedrons, cylinders, and spheres. The homogeneous organic composite according to Claim 5.

7. The first organic compound and the second organic compound have a vapor deposition temperature difference of 0 to 30 °C under a pressure of 10 －６ torr. The homogeneous organic composite according to Claim 1.

8. The mixing ratio of the above-mentioned first organic compound and the above-mentioned second organic compound is a weight ratio of 1:99 to 99:

1. The homogeneous organic composite according to claim 1.

9. The homogeneous organic composite according to claim 1, which does not contain an inorganic substance and a dopant.

10. The above-mentioned first organic compound and the above-mentioned second organic compound are the same as or different from each other, and each independently is 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. The homogeneous organic composite according to claim 1.

11. The above-mentioned first organic compound and the above-mentioned second organic compound are host materials. The homogeneous organic composite according to claim 1.

12. The above-mentioned first organic compound is a compound having higher hole characteristics than the above-mentioned second organic compound. The above-mentioned second organic compound is a compound containing at least one electron-withdrawing group (EWG) represented by the following formula. The homogeneous organic compound according to claim 1. 【Chemical Formula 1】 In the formula, X １ ~ X ８ and Y １ ~ Y ５ are the same as or different from each other, and each independently is N or C(R), provided that the above-mentioned monocyclic or polycyclic moiety contains at least one N. When there are a plurality of the above-mentioned C(R), the plurality of Rs are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, C １ ~ C ４０ alkyl group, C ２ ~ C ４０ alkenyl group, C ２ ~ C ４０ alkynyl group, C ３ ~ C ４０a cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, C ６ to C ６０ an aryl group, a heteroaryl group having 5 to 60 ring atoms, C １ to C ４０ an alkyloxy group, C ６ to C ６０ an aryloxy group, C １ to C ４０ an alkylsilyl group, C ６ to C ６０ an arylsilyl group, C １ to C ４０ an alkylboron group, C ６ to C ６０ an arylboron group, C ６ to C ６０ an arylphosphine group, C ６ to C ６０ an arylphosphine oxide group, and C ６ to C ６０ an arylamine group, or these may combine with adjacent groups to form a condensed ring, The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group of the above R are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C １ to C ４０ an alkyl group, C ２ to C ４０ an alkenyl group, C ２ to C ４０ an alkynyl group, C ３ to C ４０ a cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, C ６ to C ６０ an aryl group, a heteroaryl group having 5 to 60 ring atoms, C １ to C ４０ an alkyloxy group, C ６ to C ６０ an aryloxy group, C １ to C ４０ alkylsilyl group, C ６ to C ６０ arylsilyl group, C １ to C ４０ alkylboron group, C ６ to C ６０ arylboron group, C ６ to C ６０ arylphosphine group, C ６ to C ６０ arylphosphine oxide group, and C ６ to C ６０ aryl amine group, and may be substituted with one or more substituents selected from the group consisting of, and when there are a plurality of the substituents, they may be the same as or different from each other. )

13. The second organic compound is a homogeneous organic compound according to claim 13, which is a compound containing at least one nitrogen-containing moiety represented by the following formula. 【Chemical formula 2】

14. Anode; A cathode disposed opposite to the anode; At least one organic layer disposed between the anode and the cathode; comprising The at least one organic layer contains the homogeneous organic composite according to any one of claims 1 to 13, and the organic EL element.

15. The at least one organic layer is formed by vapor-depositing a homogeneous organic composite that is solid at room temperature, and the organic EL element according to claim 14.

16. A first step of completely dissolving two or more organic compounds in at least one organic solvent to form a homogeneous phase and then solidifying; and A second step of pressing and molding the solidified homogeneous organic composite under conditions without performing heat treatment; The method for producing a homogeneous organic composite according to claim 1, comprising.

17. In the second stage, the forming is carried out under a pressure of 20,000 to 40,000 kgf / cm ２ The manufacturing method according to claim 16.

18. The solidified homogeneous organic composite obtained in the first stage is in powder form or stick form, The homogeneous organic composite formed in the second stage is in pellet form selected from the group consisting of polyhedrons, cylinders, and spheres. The manufacturing method according to claim 16.

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