Organic alloy for organic optoelectronic device, organic optoelectronic device, and display device

Abstract

To provide an organic optoelectronic device having high efficiency and a long life.SOLUTION: Disclosed are: an organic alloy for an organic optoelectronic device that is an organic alloy of at least two kinds of organic compounds, the at least two kinds of organic compounds include a first organic compound and a second organic compound, the difference in evaporation temperature between the first organic compound and the second organic compound is less than or equal to 20°C at 10-3 torr or less, and the light emitting wavelength of the organic alloy is different from the light emitting wavelengths of the first organic compound, the second organic compound, and a simple mixture of the first organic compound and the second organic compound; and an organic optoelectronic device and a display device that include the organic alloy.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an organic alloy for an organic optoelectronic device, an organic optoelectronic device, and a display device. [Background technology]

[0002] An organic optoelectric diode is a device that can convert electrical energy and light energy into each other.

[0003] Organic optoelectronic devices can be broadly divided into two types based on their operating principles: one is a photoelectric device in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to generate electrical energy, and the other is a light-emitting device in which voltage or current is supplied to electrodes to generate light energy from electrical energy.

[0004] Examples of organic optoelectronic devices include organic photoelectric devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.

[0005] Among these, organic light emitting diodes (OLEDs) have been attracting much attention in recent years due to the increasing demand for flat panel display devices. Organic light emitting diodes (OLEDs) are devices that convert electrical energy into light by applying current to an organic light emitting material, and typically have a structure in which an organic layer is inserted between an anode and a cathode. Here, the organic layer may include an emitting layer and, optionally, an auxiliary layer. The auxiliary layer may include, for example, at least one layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer, and a hole blocking layer to improve the efficiency and safety of the organic light emitting device.

[0006] The performance of an organic light-emitting device is greatly influenced by the properties of the organic layer, and particularly by the organic material contained in the organic layer.

[0007] In particular, in order for the organic light emitting device to be applied to large flat panel displays, it is necessary to develop an organic material that can enhance the mobility of holes and electrons and at the same time, improve electrochemical stability. Summary of the Invention [Problem to be solved by the invention]

[0008] An object of one embodiment of the present invention is to provide an organic alloy that is applicable to organic optoelectronic devices.

[0009] It is an object of another embodiment of the present invention to provide an organic optoelectronic device comprising said organic alloy.

[0010] Another object of the present invention is to provide a display device including the organic optoelectronic device. [Means for solving the problem]

[0011] According to one embodiment of the present invention, there is provided an organic alloy of at least two organic compounds, the at least two organic compounds being a first organic compound, and a second organic compound, 10 -3 The difference in evaporation temperature between the first organic compound and the second organic compound is 20°C or less at or below torr, and the emission wavelength of the organic alloy is different from the emission wavelengths of the first organic compound, the second organic compound, and a simple mixture of the first organic compound and the second organic compound.

[0012] According to another embodiment of the present invention, there is provided an organic optoelectronic device comprising an anode and a cathode facing each other, and at least one organic layer located between the anode and the cathode, wherein the organic layer comprises the organic alloy.

[0013] According to another embodiment of the present invention, there is provided a display device including the organic optoelectronic device. [Effects of the Invention]

[0014] According to the present invention, an organic alloy having properties different from those of existing single organic compounds and simple mixtures thereof is provided, and by applying this to an organic optoelectronic device, an organic optoelectronic device with high efficiency and long life can be realized. [Brief explanation of the drawings]

[0015] [Figure 1] 1 is a cross-sectional view illustrating an organic light emitting device according to an embodiment of the present invention. [Figure 2] 1 is a cross-sectional view illustrating an organic light emitting device according to an embodiment of the present invention. [Figure 3] 1 is a graph showing the emission characteristics of the organic alloy according to Example 1 and the organic materials according to Comparative Examples 1 to 3 depending on the wavelength. [Figure 4] 1 is a graph showing the emission characteristics of the organic alloy according to Example 2 and the organic materials according to Comparative Examples 1, 4, and 5 depending on the wavelength. DETAILED DESCRIPTION OF THE INVENTION

[0016] DETAILED DESCRIPTION OF THE INVENTION The following detailed description of the present invention is given by way of example only, and the present invention is not limited thereto but is defined only by the scope of the claims.

[0017] Unless otherwise defined, the term "substituted" used herein means that at least one hydrogen atom in a substituent or compound has been replaced with deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1-C30 amine group, a nitro group, a substituted or unsubstituted C1-C40 silyl group, a C1-C30 alkyl group, a C1-C10 alkylsilyl group, a C3-C30 cycloalkyl group, a C2-C30 heterocycloalkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, a C1-C20 alkoxy group, a fluoro group, a C1-C10 trifluoroalkyl group such as a trifluoromethyl group, or a cyano group.

[0018] In addition, two adjacent substituents among the substituted halogen groups, hydroxy groups, amino groups, substituted or unsubstituted C1-C20 amine groups, nitro groups, substituted or unsubstituted C3-C40 silyl groups, C1-C30 alkyl groups, C1-C10 alkylsilyl groups, C3-C30 cycloalkyl groups, C2-C30 heterocycloalkyl groups, C6-C30 aryl groups, C2-C30 heteroaryl groups, C1-C20 alkoxy groups, fluoro groups, C1-C10 trifluoroalkyl groups such as trifluoromethyl groups, or cyano groups may be fused to form a ring. For example, the substituted C6-C30 aryl groups may be fused to adjacent other substituted C6-C30 aryl groups to form a substituted or unsubstituted fluorene ring.

[0019] As used herein, unless otherwise defined, "hetero" means that a functional group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, P, and Si, and the remainder is carbon.

[0020] As used herein, the term "alkyl group" refers to an aliphatic hydrocarbon group unless otherwise defined. The alkyl group may be a "saturated alkyl group" that does not contain any double or triple bonds.

[0021] The alkyl group may be a C1 to C30 alkyl group. More specifically, the alkyl group may be a C1 to C20 alkyl group or a C1 to C10 alkyl group. For example, a C1 to C4 alkyl group means an alkyl group containing 1 to 4 carbon atoms in the alkyl chain, and is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and t-butyl.

[0022] Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, a hexyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0023] As used herein, the term "aryl group" refers to a substituent in which all elements of the cyclic substituent have p-orbitals and these p-orbitals form conjugation, including monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0024] As used herein, the term "heteroaryl group" refers to an aryl group containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, P, and Si, and the remainder being carbon. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 heteroatoms.

[0025] More specifically, the substituted or unsubstituted C6 to C30 aryl group and / or the substituted or unsubstituted C2 to C30 heteroaryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted chlorine atom ... A lysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted The alkyl group may be, but is not limited to, a naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazole group, or a combination thereof.

[0026] In this specification, the term "hole characteristic" refers to the ability to donate electrons to form holes when an electric field is applied, and refers to the ability to have conduction characteristics depending on the HOMO level, facilitating the injection of holes formed in the anode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the anode, and the movement of holes in the light-emitting layer.

[0027] The electronic properties refer to the ability to receive electrons when an electric field is applied, and refer to the properties of having conduction properties according to the LUMO level, facilitating the injection of electrons formed in the cathode into the light-emitting layer, and the movement of electrons formed in the light-emitting layer to the cathode and within the light-emitting layer.

[0028] Hereinafter, an organic alloy for an organic optoelectronic device according to one embodiment of the present invention will be described.

[0029] The organic alloy is a result of pre-treatment of two or more single organic compounds, which may have chemical interactions between the single organic compounds. The pre-treatment may be, but is not limited to, a heat treatment process such as heating and sublimation followed by cooling.

[0030] When the two or more single organic compounds include a first organic compound and a second organic compound, the first organic compound and the second organic compound may have the same evaporation temperature or an evaporation temperature within a predetermined range for pretreatment. Here, the evaporation temperature is defined as the evaporation temperature at which the first organic compound and the second organic compound are evaporated to about 10°C. -3 This refers to the temperature at which deposition can be performed at a specified rate on a substrate in a high vacuum of less than Torr. For example, -3 It may be the average temperature of the source measured when thermally evaporating to a thickness of about 300 nm to 800 nm at a rate of about 0.5 to 2 Å / sec in a high vacuum of less than Torr.

[0031] For example, about 10 -3 At or below 100 torr, the difference in evaporation temperature between the first organic compound and the second organic compound may be about 20°C or less. Within the above range, the difference in evaporation temperature between the first organic compound and the second organic compound may be about 0°C to 10°C, and may be about 0°C to 5°C.

[0032] As described above, the organic alloy has unique properties that differ from those of the individual organic compounds and simple mixtures in which no chemical interaction exists between the individual organic compounds due to the chemical interactions between the two or more individual organic compounds. Here, a simple mixture refers to a mixture of the individual organic compounds that is simply physically mixed without any pretreatment. That is, when the two or more individual organic compounds include a first organic compound and a second organic compound, a simple mixture of the first organic compound and the second organic compound exhibits the properties of the first organic compound, the second organic compound, or a combination thereof. However, an organic alloy of the first organic compound and the second organic compound may have unique properties that differ from those of the first organic compound, the second organic compound, or a simple mixture thereof.

[0033] As an example, the emission wavelength of the organic alloy may be different from the emission wavelengths of the first organic compound, the second organic compound, and simple mixtures thereof.

[0034] The organic alloy can emit new energy and light due to a new energy bandgap between the high HOMO energy level and the low LUMO energy level of the two materials, which is created by the intermolecular electron transfer system (intermolecular donor-acceptor system) between the first organic compound and the second organic compound. The band gap may be between the LUMO energy level of the first organic compound and the HOMO energy level of the second organic compound, or between the LUMO energy level of the second organic compound and the HOMO energy level of the first organic compound. Conversely, a simple mixture of the first and second organic compounds may have either a band gap between the LUMO energy and HOMO energy of the first organic compound or a band gap between the LUMO energy and HOMO energy of the second organic compound. In this case, the organic alloy may have a band gap smaller or larger than those of the first organic compound, the second organic compound, and the simple mixture thereof. Therefore, the emission wavelength of the organic alloy may be different from those of the first organic compound, the second organic compound, and the simple mixture thereof.

[0035] The maximum emission wavelength (λ max ) can be shifted by about 20 nm or more from the maximum emission wavelength of a simple mixture of the first organic compound and the second organic compound, for example, can be shifted by about 20 nm or more to longer wavelengths.

[0036] Additionally, the color of the organic alloy may be different from the color of the first organic compound, the second organic compound, and the simple mixture thereof.

[0037] The glass transition temperature (Tg) of the organic alloy may be different from the glass transition temperatures (Tg) of the first organic compound, the second organic compound, and the simple mixture thereof. The crystallization temperature (Tc) of the organic alloy may be different from the crystallization temperatures of the first organic compound, the second organic compound, and the simple mixture thereof. The melting temperature (Tm) of the organic alloy may be different from the melting temperatures of the first organic compound, the second organic compound, and the simple mixture thereof. The glass transition temperature (Tg), the crystallization temperature (Tc), and the melting temperature (Tm) indicate thermodynamic properties specific to molecules, and substances with different glass transition temperatures (Tg), crystallization temperatures (Tc), and melting temperatures (Tm) can be considered different substances.

[0038] The thermodynamic values ​​of the organic alloy, such as the glass transition temperature (Tg), crystallization temperature (Tc), and melting temperature (Tm), may be intrinsic values ​​or may be substantially constant within an error range. The error range may vary depending on the measurement conditions, but may be, for example, about ±5°C, or even about ±2°C. This differs from a simple mixture of a first organic compound and a second organic compound, which does not have intrinsic thermodynamic values.

[0039] The organic alloy can be pretreated in various ways, for example, by liquefying or vaporizing a first organic compound and a second organic compound by heat-treating them at a temperature above the evaporation temperature, and then solidifying the heat-treated compounds by cooling them. The first organic compound and the second organic compound may be in a molten liquid phase or a vaporized gas phase at the evaporation temperature, and the pretreated organic alloy may be in a solid mass or powder form. In one example, the organic alloy obtained in a solid mass form may be further subjected to an additional step of physically pulverizing it using a mixer or the like.

[0040] The organic alloy is a result of the pretreatment as described above, and can be supplied using a single source during thin film formation, thereby simplifying the process by eliminating the process control steps required when supplying two or more materials from separate sources.

[0041] In addition, since the organic alloy is a product obtained by pretreatment as described above, two or more kinds of single organic compounds may be supplied from separate supply sources, or two or more kinds of single organic compounds may be supplied from separate supply sources. This ensures uniformity and consistency of the deposited material compared to when a simple mixture of the above is supplied from a single source. Therefore, when forming multiple thin films in successive steps, thin films having substantially the same ratio of components can be continuously produced, thereby improving the reproducibility and reliability of the thin films.

[0042] As described above, the first organic compound and the second organic compound are not particularly limited as long as they have an evaporation temperature that allows pretreatment at a predetermined temperature. For example, a compound with strong electronic properties and a compound with strong hole properties can be used to improve the mobility of electrons and holes. For example, the first organic compound may be a compound with relatively strong electronic properties, and the second organic compound may be a compound with relatively strong hole properties. An organic alloy of the first organic compound with relatively strong electronic properties and the second organic compound with relatively strong hole properties may have bipolar properties.

[0043] The first organic compound is a compound having relatively strong electronic properties, and may be, for example, a compound represented by the following Chemical Formula 1:

[0044] [ka]

[0045] In the above Chemical Formula 1, Each Z is independently N or CR a and At least one of Z is N; R 1 ~R 10 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof; In the formula 1, the total number of 6-membered rings substituted with triphenylene groups is 6 or less; L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group; n1 to n3 are each independently 0 or 1, and n1+n2+n3≧1.

[0046] Here, the six-membered ring substituted on the triphenylene group refers to all six-membered rings directly or indirectly linked to the triphenylene group, and includes six-membered rings consisting of carbon atoms, nitrogen atoms, or a combination thereof.

[0047] The first organic compound may be represented by, for example, the following Chemical Formula 1-I or Chemical Formula 1-II depending on the bonding position of the triphenylene group.

[0048] [ka]

[0049] In the above chemical formula 1-I or 1-II, Z, R 1 ~R 10 , L and n1 to n3 are defined as above.

[0050] The first organic compound comprises a triphenylene group and at least one nitrogen-containing heteroaryl group.

[0051] The first organic compound may have a structure that is easy to accept electrons when an electric field is applied by including at least one nitrogen-containing ring, thereby reducing the driving voltage of an organic optoelectronic device using the first organic compound.

[0052] In addition, the first organic compound contains both a triphenylene structure that is prone to receiving holes and a nitrogen-containing ring portion that is prone to receiving electrons, thereby forming a bipolar structure and appropriately balancing the flow of holes and electrons, thereby improving the efficiency of an organic optoelectronic device using the first organic compound.

[0053] The first organic compound represented by Chemical Formula 1 has at least one kink structure centered around an arylene group and / or a heteroarylene group.

[0054] The twisted structure refers to a structure in which the connecting portion between two arylene groups and / or heteroarylene groups does not form a linear structure. For example, in the case of phenylene, orthophenylene (o-phenylene) and metaphenylene (m-phenylene), which do not form a linear connecting portion, have the twisted structure, while paraphenylene (p-phenylene), which forms a linear connecting portion, does not have the twisted structure.

[0055] In Chemical Formula 1, the twisted structure may be formed around the linking group (L) and / or the arylene group / heteroarylene group.

[0056] For example, when n1 in the above formula 1 is 0, that is, in a structure without a linking group (L), a twisted structure can be formed around the arylene group / heteroarylene group, and the compound may be, for example, a compound represented by the following formula 1a or 1b.

[0057] [ka]

[0058] In the above chemical formula 1a or 1b, Z, R 1 ~R 10 and L is defined as above.

[0059] For example, when n1 in Formula 1 is 1, a twisted structure can be formed around the linking group (L), and L may be, for example, a substituted or unsubstituted phenylene group having a twisted structure, a substituted or unsubstituted biphenylene group having a twisted structure, or a substituted or unsubstituted terphenylene group having a twisted structure. L may be, for example, one selected from the substituted or unsubstituted groups listed in Group 1 below.

[0060] [ka]

[0061] In Group 1, R 15 ~R 42 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6-C30 arylamine group, a substituted or unsubstituted C6-C30 heteroarylamine group, a substituted or unsubstituted C1-C30 alkoxy group, ha The alkyl group may be a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof.

[0062] The first organic compound preferably has at least two twisted structures, and may have, for example, two to four twisted structures.

[0063] The first organic compound has the twisted structure described above, which allows for appropriate charge localization and effective control of the flow of the conjugated system, thereby improving the lifetime of an organic optoelectronic device to which the composition is applied.

[0064] Also, in chemical formula 1, R 1 ~R 6 That is, by limiting the total number of 6-membered rings contained in the substituents substituted on the triphenylene group to 6 or less, it is possible to reduce the phenomenon of the compound being thermally decomposed due to high temperatures during the deposition process.

[0065] In addition, the first organic compound can effectively prevent stacking of compounds due to the structure, thereby reducing process stability and lowering deposition temperature. This stacking prevention effect can be further enhanced when the first organic compound includes the linking group (L) of Formula 1.

[0066] The first organic compound may be represented by, for example, any one of the following chemical formulas 1c to 1t.

[0067] [ka]

[0068] [ka]

[0069] [ka]

[0070] In the above chemical formulas 1c to 1t, Z and R 1 ~R 10 are as described above, R 60 ~R 77 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6-C30 arylamine group, a substituted or unsubstituted C6-C30 heteroarylamine group, a substituted or unsubstituted C1-C30 alkoxy group, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof.

[0071] The first organic compound may be, for example, a compound listed in Group 2 below, but is not limited thereto.

[0072] [ka]

[0073] [ka]

[0074] [ka]

[0075] [ka]

[0076] [ka]

[0077] [ka]

[0078] The first organic compound may be used alone or in combination of two or more.

[0079] The second organic compound is a compound having relatively strong hole characteristics, and may be, for example, a compound represented by the following Chemical Formula 2:

[0080] [ka]

[0081] In the above Chemical Formula 2, Y 1 and Y 2 each independently represents a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof; Ar 1 and Ar 2is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof; R 11 ~R 13 and R 43 ~R 44 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, or a combination thereof.

[0082] The second organic compound is a compound having bipolar properties with relatively strong hole characteristics, and forms an organic alloy with the first organic compound to enhance charge mobility and safety, thereby significantly improving luminous efficiency and lifespan characteristics.

[0083] Ar of Formula 2 1 and Ar 2 are substituents having hole or electron properties and may each independently be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

[0084] Ar of Formula 2 1 and Ar 2 At least one of the groups may be, for example, a substituent having electronic properties, for example, a substituent represented by the following chemical formula A:

[0085] [ka]

[0086] In the above chemical formula A, Each Z is independently N or CR b and A1 and A2 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof; At least one of Z, A1, and A2 contains N; a and b each independently represent 0 or 1.

[0087] The substituent represented by the chemical formula A may be, for example, one of the functional groups listed in Group 3 below.

[0088] [ka]

[0089] In addition, Ar in the above-mentioned Chemical Formula 2 1 and Ar 2 At least one of the groups may be, for example, a substituent having hole properties, such as a substituent listed in Group 4 below.

[0090] [ka]

[0091] The compound represented by Chemical Formula 2 may be selected from the compounds listed in Group 5 below. may be selected, but is not limited to this.

[0092] [ka]

[0093] [ka]

[0094] [ka]

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] The second organic compound may be used alone or in combination of two or more.

[0100] The first organic compound and the second organic compound can be combined in various ways to prepare various organic alloys. For example, the first organic compound may be any of the compounds listed in Group A below. The second organic compound may be at least one of the compounds listed in Group B below, but is not limited thereto.

[0101] [ka]

[0102] As described above, the first organic compound is a compound with relatively strong electronic properties, and the second organic compound is a compound with relatively strong hole properties. By pre-treating these to form an organic alloy, the mobility of electrons and holes can be increased, and the luminous efficiency can be significantly improved, compared to when the first compound or the second compound is used alone.

[0103] In devices incorporating a material with biased electron or hole characteristics into the light-emitting layer, carrier recombination occurs at the interface between the light-emitting layer and the electron or hole transport layer, resulting in relatively frequent exciton formation. As a result, the interaction between molecular excitons in the light-emitting layer and charges at the transport layer interface causes a rapid drop in efficiency (roll-off), which also leads to a rapid drop in luminescence lifetime. To solve this problem, an organic alloy of a first organic compound and a second organic compound can be introduced to create a device that balances the carriers in the light-emitting layer so that the light-emitting region is not biased toward either the electron or hole transport layer. This can significantly improve roll-off and lifetime.

[0104] The organic alloy can be obtained by using the first organic compound and the second organic compound in a molar ratio of, for example, about 1:10 to 10:1. In one example, the organic alloy can be obtained by using the first organic compound and the second organic compound in a molar ratio of about 1:4 to 4:1. It can be obtained by using about a 1:1 molar ratio.

[0105] By falling within this range, bipolar characteristics can be more effectively realized, and efficiency and lifespan can be improved at the same time.

[0106] The organic alloy may be obtained by pretreating the first organic compound and the second organic compound described above, or may be pretreated by further including one or more organic compounds other than the first organic compound and the second organic compound described above.

[0107] The organic alloy can be used as an organic material for an organic optoelectronic device, 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.

[0108] For example, the organic alloy can be used as a light-emitting material for an organic optoelectronic device. In this case, the light-emitting material can use the organic alloy as a host and further include at least one dopant. The dopant can be a red, green, or blue dopant, such as a phosphorescent dopant.

[0109] The dopant is a material that emits light when mixed in a small amount into the organic alloy, and may generally be a material such as a metal complex that emits light by multiple excitation, which excites the dopant to a triplet state or higher. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may contain one or more dopants.

[0110] Examples of the phosphorescent dopant include organometallic compounds containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the following chemical formula Z, but is not limited thereto.

[0111] [ka]

[0112] In the chemical formula Z, M is a metal, and L and X are the same or different and are ligands that form a complex compound with M.

[0113] The M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and the L and X may be, for example, a bidentate ligand.

[0114] The organic materials can be formed by dry deposition methods such as chemical vapor deposition or solution processes.

[0115] An organic optoelectronic device using the above-mentioned organic materials will now be described.

[0116] The organic optoelectronic device is not particularly limited as long as it is a device capable of converting electrical energy and light energy into each other, and examples thereof include organic photoelectric devices, organic light-emitting devices, organic solar cells, and organic photoreceptor drums.

[0117] The organic optoelectronic device includes an anode and a cathode facing each other, and a conductive layer between the anode and the cathode. and at least one organic layer located on the substrate, the organic layer may include the organic material described above.

[0118] Here, an organic light-emitting element, which is an example of an organic optoelectronic element, will be described with reference to the drawings.

[0119] 1 and 2 are cross-sectional views showing an organic light-emitting device according to one embodiment of the present invention.

[0120] Referring to FIG. 1, an organic optoelectronic device 100 according to one embodiment of the present invention includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 located between the anode 120 and the cathode 110 .

[0121] The anode 120 may be made of a conductor with a high work function to facilitate hole injection, such as a metal, metal oxide, and / or conductive polymer. Examples of the anode 120 include, but are not limited to, metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO and Al or SnO and Sb; and conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDT), polypyrrole, and polyaniline.

[0122] The cathode 110 may be made of a conductor with a low work function, for example, a metal, a metal oxide, and / or a conductive polymer, to facilitate electron injection. Examples of the cathode 110 include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, and barium, or alloys thereof, including, but not limited to, multilayer structures such as LiF / Al, LiO / Al, LiF / Ca, LiF / Al, and BaF / Ca.

[0123] The organic layer 105 includes a light-emitting layer 130 that includes the organic materials described above.

[0124] Light-emitting layer 130 can include, for example, the organic materials described above.

[0125] 2, the organic light emitting device 200 further includes a hole assisting layer 140 in addition to the light emitting layer 130. The hole assisting layer 140 can further enhance hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and can block electrons. The hole assisting layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer.

[0126] In addition, in one embodiment of the present invention, the organic light emitting device may further include an electron transport layer, an electron injection layer, a hole injection layer, etc. in addition to the organic thin film layer 105 in FIG. 1 or FIG.

[0127] The organic light emitting device 100, 200 can be manufactured by forming an anode or cathode on a substrate, forming an organic layer using a dry deposition method such as vacuum evaporation, sputtering, plasma plating, or ion plating, and then forming a cathode or anode thereon.

[0128] The above-described organic light emitting device can be applied to an organic light emitting display device. [Example]

[0129] Specific examples of the present invention will be presented below. However, the examples described below are merely for the purpose of specifically illustrating and explaining the present invention, and the present invention should not be limited thereby.

[0130] (Preparation of single organic compounds) Synthesis of the first organic compound: Compound A-33 Synthesis Example 1: Synthesis of Intermediate I-2

[0131] [ka]

[0132] Under a nitrogen atmosphere, 32.7 g (107 mmol) of 2-bromotriphenylene was dissolved in 0.3 L of tetrahydrofuran (THF). Then, 20 g (128 mmol) of 3-chlorophenylboronic acid and 1.23 g (1.07 mmol) of tetrakis(triphenylphosphine)palladium were added and stirred. 36.8 g (267 mmol) of potassium carbonate saturated with water was added and heated to reflux at 80°C for 24 hours. After the reaction was completed, the reaction mixture was added with water and extracted with dichloromethane (DCM). The water was removed with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography to yield 22.6 g (63%) of compound I-2.

[0133] HRMS(70eV,EI+):m / z calcd for C 24 H 15 Cl:338.0862,found:338. Elemental Analysis: C, 85%; H, 5% Synthesis Example 2: Synthesis of Intermediate I-3

[0134] [ka]

[0135] In a nitrogen atmosphere, 22.6 g (66.7 mmol) of compound I-2 was dissolved in 0.3 L of dimethylformamide (DMF), and then 25.4 g (100 mmol) of bis(pinacolato)diboron, 0.54 g (0.67 mmol) of (1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium(II), and 16.4 g (167 mmol) of potassium acetate were added and heated to reflux at 150°C for 48 hours. After the reaction was completed, the reaction solution was Water was added, the mixture was filtered, and then dried in a vacuum oven. The resulting residue was purified by flash column chromatography to obtain 18.6 g (65%) of compound I-3.

[0136] HRMS(70eV,EI+):m / z calcd for C 30 H 27 BO2:430.2104,found:430. Elemental Analysis: C, 84%; H, 6% Synthesis Example 3: Synthesis of Intermediate I-6

[0137] [ka]

[0138] Under a nitrogen atmosphere, 50 g (116 mmol) of compound I-3 was dissolved in 0.5 L of tetrahydrofuran (THF), followed by the addition of 39.4 g (139 mmol) of 1-bromo-3-iodobenzene and 1.34 g (1.16 mmol) of tetrakis(triphenylphosphine)palladium and stirring. 40.1 g (290 mmol) of potassium carbonate saturated with water was added and heated to reflux at 80°C for 12 hours. After the reaction was completed, the reaction solution was added with water and extracted with dichloromethane (DCM). The water was removed with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography to yield 42.6 g (80%) of compound I-6.

[0139] HRMS(70eV,EI+):m / z calcd for C 30 H 19 Br:458.0670,found:458. Elemental Analysis: C, 78%; H, 4% Synthesis Example 4: Synthesis of Intermediate I-7

[0140] [ka]

[0141] Under a nitrogen atmosphere, 40 g (87.1 mmol) of compound I-6 was dissolved in 0.3 L of dimethylformamide (DMF), followed by the addition of 26.5 g (104 mmol) of bis(pinacolato)diboron, 0.71 g (0.87 mmol) of (1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium(II), and 21.4 g (218 mmol) of potassium acetate. The mixture was heated to reflux at 150 °C for 26 hours. After the reaction was completed, water was added to the reaction solution, and the mixture was filtered and dried in a vacuum oven. The resulting residue was purified by flash column chromatography to yield 34 g (77%) of compound I-7.

[0142] HRMS(70eV,EI+):m / z calcd for C36 H 31 BO2:506.2417,found:506. Elemental Analysis: C, 85%; H, 6% Synthesis Example 5: Synthesis of Compound A-33

[0143] [ka]

[0144] Under a nitrogen atmosphere, 20 g (39.5 mmol) of compound 1-7 was dissolved in 0.2 L of tetrahydrofuran (THF). Then, 10.6 g (39.5 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.46 g (0.4 mmol) of tetrakis(triphenylphosphine)palladium were added and stirred. 13.6 g (98.8 mmol) of potassium carbonate saturated with water was added and heated to reflux at 80°C for 23 hours. After the reaction was completed, the reaction mixture was added with water and extracted with dichloromethane (DCM). The water was removed with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography to obtain compound A-33 (17.9 g, 74%).

[0145] HRMS(70eV,EI+):m / z calcd for C 45 H 29 N3:611.2361,found:611. Elemental Analysis: C, 88%; H, 5% The evaporation temperature of the compound A-33 is 10 -3 Torr and below, it is approximately 226±10°C.

[0146] Synthesis Example 1 of the Second Organic Compound: Compound B-10

[0147] [ka]

[0148] Step 1: Synthesis of Compound J 26.96 g (81.4 mmol) of N-phenylcarbazole-3-boronic acid pinacolatoate, 23.96 g (97.36 mmol) of 3-bromocarbazole, 230 mL of tetrahydrofuran, and 100 mL of 2 M potassium carbonate aqueous solution were mixed and heated under reflux for 12 hours under a nitrogen atmosphere. After the reaction was completed, methanol was poured into the reaction mixture and the resulting solid was filtered. The solid was then redissolved in chlorobenzene and stirred with activated carbon and anhydrous magnesium sulfate. The solution was filtered and recrystallized using chlorobenzene and methanol to obtain 22.6 g of compound J (yield: 68%).

[0149] HRMS(70eV,EI+):m / z calcd for C 30 H 20 N2:408.16,found:408 Elemental Analysis: C, 88%; H, 5% Step 2: Synthesis of compound B-10 22.42 g (54.88 mmol) of compound J, 20.43 g (65.85 mmol) of 2-bromo-4,6-diphenylpyridine, and 7.92 g (82.32 mmol) of sodium tert-butoxide were dissolved in 400 mL of toluene, followed by dropwise addition of 1.65 g (1.65 mmol) of palladium dibenzylideneamine and 1.78 g (4.39 mmol) of tert-butylphosphine (P(t-Bu)3). The reaction solution was heated and stirred at 110°C for 12 hours under a nitrogen stream. After the reaction was completed, methanol was poured into the reaction mixture and the resulting solid was filtered. The solid was then redissolved in chlorobenzene, added with activated carbon and anhydrous magnesium sulfate, and stirred. The solution was filtered and recrystallized using chlorobenzene and methanol to obtain 28.10 g (80% yield) of compound B-10.

[0150] HRMS(70eV,EI+):m / z calcd for C 47 H 31 N3:637.25,found:637 Elemental Analysis: C, 89%; H, 5% The evaporation temperature of the compound B-10 is 10 -3 Torr and below, approximately 225±10°C.

[0151] Synthesis Example 2 of the Second Organic Compound: Compound B-43

[0152] [ka]

[0153] 12.33 g (30.95 mmol) of biphenylcarbazolyl bromide, 12.37 g (34.05 mmol) of biphenylcarbazolyl boronic acid, 12.83 g (92.86 mmol) of potassium carbonate, and 1.07 g (0.93 mmol) of tetrakis-(triphenylphosphine)palladium(0) were suspended in 120 ml of toluene and 50 ml of distilled water and refluxed for 12 hours. The mixture was then extracted with dichloromethane and distilled water, and the organic layer was filtered through a silica gel filter. The organic solution was then removed, and the solid product was recrystallized from dichloromethane and n-hexane to obtain 18.7 g (92% yield) of compound B-43.

[0154] HRMS(70eV,EI+):m / z calcd for C48H 32 N2:636.26,found:636 Elemental Analysis: C, 91%; H, 5% The evaporation temperature of the compound B-43 is 10 -3 Torr and below, it is approximately 232±10°C.

[0155] Example: Preparation of Organic Alloys Example 1: Organic alloy of compound A-33 and compound B-10 10 -3Compound A-33 and compound B-10 were placed in a vacuum chamber at a pressure of less than Torr in a molar ratio of 1:1, and the temperature of the vacuum chamber was raised to melt compound A-33 and compound B-10. The melted compound was then cooled to room temperature (25°C) to solidify, and the resulting product was pulverized in a mixer to obtain a powdered organic alloy.

[0156] Example 2: Organic alloy of Compound A-33 and Compound B-43 10 -3 Compound A-33 and compound B-43 were placed in a vacuum chamber at a pressure of less than Torr in a molar ratio of 1:1, and the temperature of the vacuum chamber was raised to melt compound A-33 and compound B-43. The melted compound was then cooled to room temperature (25°C) to solidify, and the resulting product was pulverized in a mixer to obtain a powdered organic alloy.

[0157] Comparative Example: Preparation of Single Compounds and Simple Mixtures Comparative Example 1: Single Compound A-33 Compound A-33 prepared in Synthesis Example 5 was pulverized in a mixer at room temperature (25° C.) to prepare a powder of compound A-33.

[0158] Comparative Example 2: Single Compound B-10 Compound B-10 prepared in Synthesis Example 1 of the Second Organic Compound was mixed in a mixer at room temperature (25°C) to form a powder. Compound B-10 was prepared in powder form by crushing.

[0159] Comparative Example 3: Simple mixture of Compound A-33 and Compound B-10 Compound A-33 prepared in Synthesis Example 5 and compound B-10 prepared in Synthesis Example 1 of the second organic compound were mixed in a 1:1 molar ratio and physically ground in a mixer to prepare a simple mixture.

[0160] Comparative Example 4: Single Compound B-43 Compound B-43 prepared in Synthesis Example 2 of the Second Organic Compound was pulverized in a mixer at room temperature (25° C.) to prepare a powder of compound B-43.

[0161] Comparative Example 5: Simple mixture of Compound A-33 and Compound B-43 Compound A-33 prepared in Synthesis Example 5 and compound B-43 prepared in Synthesis Example 1 of the second organic compound were mixed at room temperature (25°C) in a 1:1 molar ratio and physically ground in a mixer to prepare a simple mixture.

[0162] (evaluation) Rating 1 The optical properties of the organic alloys of Examples 1 and 2 and the organic materials of Comparative Examples 1 to 5 were evaluated. The optical properties were measured by measuring the photoluminescence (PL) spectra of the powders of the organic alloys of Examples 1 and 2 and the organic materials of Comparative Examples 1 to 5 using a fluorescence spectrophotometer (F-4500, manufactured by Hitachi). The powder PL holder used was a solid sample holder 650-0161 (manufactured by Hitachi), and the samples were in a powder state.

[0163] The results are explained with reference to FIGS. 3 and 4 and Tables 1 and 2 below.

[0164] FIG. 3 is a graph showing the emission characteristics according to wavelength of the organic alloy of Example 1 and the organic materials of Comparative Examples 1 to 3, and FIG. 4 is a graph showing the emission characteristics according to wavelength of the organic alloy of Example 2 and the organic materials of Comparative Examples 1, 4, and 5.

[0165] [Table 1]

[0166] [Table 2]

[0167] 3 and 4 and Tables 1 and 2 below, the organic alloy according to Example 1 was It can be seen that the organic alloy of Example 2 exhibits optical properties different from those of the organic materials of Comparative Examples 1, 4, and 5.

[0168] In particular, the organic material according to Comparative Example 3, i.e., a simple mixture of the first organic compound (A-33) and the second organic compound (B-10), exhibits the optical properties of the first organic compound (A-33), the second organic compound (B-10), or a combination thereof, whereas the organic alloy according to Example 1 exhibits unique optical properties different from those of the first organic compound (A-33) and the second organic compound (B-10). For example, it can be confirmed that the maximum emission wavelength shifts to the longer wavelength side by approximately 20 nm or more.

[0169] Similarly, the organic material according to Comparative Example 5, i.e., a simple mixture of the first organic compound (A-33) and the second organic compound (B-43), exhibits the optical properties of the first organic compound (A-33), the second organic compound (B-43), or a combination thereof, whereas the organic alloy according to Example 2 exhibits unique optical properties different from those of the first organic compound (A-33) and the second organic compound (B-43). For example, it can be confirmed that the maximum emission wavelength shifts to the longer wavelength side by approximately 20 nm or more.

[0170] Furthermore, it can be seen that the organic material according to Comparative Example 3, i.e., a simple mixture of the first organic compound (A-33) and the second organic compound (B-10), has an energy level substantially similar to that of the first organic compound (A-33) or the second organic compound (B-10), whereas the organic alloy according to Example 1 has a unique energy level different from that of the first organic compound (A-33) and the second organic compound (B-10).

[0171] Similarly, it can be seen that the organic material according to Comparative Example 5, i.e., a simple mixture of the first organic compound (A-33) and the second organic compound (B-43), has an energy level substantially similar to that of the first organic compound (A-33) or the second organic compound (B-43), but the organic alloy according to Example 2 has a unique energy level different from that of the first organic compound (A-33) and the second organic compound (B-43).

[0172] Rating 2 The thermodynamic properties of the organic alloys according to Examples 1 and 2 and the organic materials according to Comparative Examples 1 to 5 were evaluated. The thermodynamic properties of the organic alloys according to Examples 1 and 2 and the organic materials according to Comparative Examples 1 to 5 were confirmed through differential scanning calorimetry, using a DSC1 (manufactured by Mettler-Toledo).

[0173] The results are shown in Tables 3 and 4.

[0174] [Table 3]

[0175] [Table 4]

[0176] Referring to Tables 3 and 4, it can be seen that the organic alloy according to Example 1 exhibits different thermodynamic properties from the organic materials according to Comparative Examples 1 to 3, and the organic alloy according to Example 2 exhibits different thermodynamic properties from the organic materials according to Comparative Examples 1, 4, and 5.

[0177] In particular, it can be seen that the organic material of Comparative Example 3, i.e., a simple mixture of the first organic compound (A-33) and the second organic compound (B-10), exhibits thermodynamic properties almost similar to those of the organic material of Comparative Example 2, i.e., the second organic compound (B-10), while the organic alloy of Example 1 exhibits thermodynamic properties different from those of the first organic compound (A-33), the second organic compound (B-10), and the simple mixture of the first organic compound (A-33) and the second organic compound (B-10).

[0178] Similarly, it can be confirmed that the organic material of Comparative Example 5, i.e., a simple mixture of the first organic compound (A-33) and the second organic compound (B-43), exhibits thermodynamic properties substantially similar to those of the organic material of Comparative Example 4, i.e., the second organic compound (B-43), while the organic alloy of Example 2 exhibits thermodynamic properties different from those of the first organic compound (A-33), the second organic compound (B-43), and the simple mixture of the first organic compound (A-33) and the second organic compound (B-43).

[0179] Rating 3 The consistency of thermodynamic properties was evaluated for the organic alloys according to Examples 1 and 2 and the organic materials according to Comparative Examples 3 and 5. The consistency of thermodynamic properties was evaluated as the constancy of the results obtained by measuring the thermodynamic properties according to Evaluation 2 multiple times.

[0180] The results are explained with reference to Tables 5 and 6.

[0181] [Table 5]

[0182] [Table 6]

[0183] Referring to Tables 5 and 6, it can be seen that the melting temperatures of the organic alloys according to Examples 1 and 2 are almost constant within the error range of ±5°C, especially ±2°C, during multiple measurements, whereas the melting temperatures of the organic materials according to Comparative Examples 3 and 5 vary significantly with each measurement, for example, by about 20°C. This indicates that the organic alloys according to Examples 1 and 2 have more consistent thermodynamic properties than a single organic compound or a simple mixture. can be confirmed.

[0184] Rating 4 The organic alloys of Examples 1 and 2 were evaluated for changes over time in the continuous process.

[0185] The change over time in the continuous process was confirmed by sequentially depositing the organic alloys of Examples 1 and 2 and the organic materials of Comparative Examples 3 and 5 on a glass substrate to form multiple thin films, and then determining whether the ratio of the single organic compound in each thin film remained constant. This was analyzed by high performance liquid chromatography (HPLC). The change over time in the continuous process can be evaluated by determining how consistently the ratio of components constituting the thin film remained constant in the continuous process.

[0186] The results are shown in Tables 7 and 8.

[0187] In Table 7 below, three samples of the organic alloy according to Example 1 were prepared, and then thin films were formed in three consecutive processes for each sample, as indicated by Examples 1-1, 1-2, and 1-3. In Table 8 below, two samples of the organic alloy according to Example 2 were prepared, and then thin films were formed in three and five consecutive processes for each sample, as indicated by Examples 2-1 and 2-2.

[0188] [Table 7]

[0189] [Table 8]

[0190] Referring to Tables 7 and 8, it can be seen that the ratio of the single organic compounds, i.e., A-33 / B-10 or A-33 / B-43, is maintained almost constant in the thin films made of the organic alloys according to Examples 1 and 2 compared to the thin films made of the organic materials according to Comparative Examples 3 and 5. This indicates that thin films made using organic alloys can be formed more reproducibly during continuous processing than thin films made using simple mixtures.

[0191] (Fabrication of organic light-emitting devices) Example 3 A glass substrate coated with a 1500Å thick ITO (indium tin oxide) thin film was ultrasonically cleaned with distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned using oxygen plasma for 10 minutes and then transferred to a vacuum deposition machine. Using the ITO transparent electrode prepared as above as an anode, N4,N4-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)biphenyl-4,4'-diamine (Compound A) was vacuum-deposited on the ITO substrate to form a hole injection layer with a thickness of 700 Å. Then, 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (1,4,5,8,9,11- A hole transport layer was formed by depositing N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine (Compound C) to a thickness of 1020 Å. A 400 Å thick light-emitting layer was formed on the hole transport layer by vacuum deposition using the organic alloy prepared in Example 1 as a host and doping it with 10 wt% tris(4-methyl-2,5-diphenylpyridine)iridium(III) (Compound D) as a dopant.

[0192] Next, 8-(4-(4-(naphthalen-2-yl)-6-(naphthalen-3-yl)-1,3,5-triazin-2-yl)phenyl)quinoline (compound Substance E) and 8-hydroxyquinolinolate lithium (Liq) were simultaneously vacuum-deposited in a 1:1 ratio to form an electron transport layer with a thickness of 300 Å. On top of the electron transport layer, 15 Å of Liq and 1200 Å of Al were sequentially vacuum-deposited to form a cathode, thereby fabricating an organic light-emitting device.

[0193] The organic light-emitting element has a structure having five organic thin film layers, and was specifically fabricated with the following structure.

[0194] ITO / A(700Å) / B(50Å) / C(1020Å) / EML[organic alloy:D=X:10%](400Å) / E:Liq(300Å) / Liq(15Å) / Al(1200Å) (X=weight ratio) Example 4 An organic light-emitting device was fabricated in the same manner as in Example 3, except that the organic alloy of Example 2 was used instead of the organic alloy of Example 1.

[0195] Comparative Example 6 An organic light emitting device was fabricated in the same manner as in Example 3, except that the organic alloy of Example 1 was replaced with the organic material of Comparative Example 1, ie, Compound A-33 as a sole host.

[0196] Comparative Example 7 An organic light emitting device was fabricated in the same manner as in Example 3, except that the organic alloy of Example 1 was replaced with the organic material of Comparative Example 2, ie, Compound B-10 as a sole host.

[0197] Comparative Example 8 An organic light-emitting device was fabricated in the same manner as in Example 3, except that the organic alloy of Example 1 was replaced with the organic material of Comparative Example 3, that is, a simple mixture of Compound A-33 and Compound B-10.

[0198] Comparative Example 9 An organic light emitting device was fabricated in the same manner as in Example 3, except that the organic alloy of Example 1 was replaced with the organic material of Comparative Example 4, ie, Compound B-43 as a sole host.

[0199] Comparative Example 10 An organic light-emitting device was fabricated in the same manner as in Example 3, except that the organic alloy of Example 1 was replaced with the organic material of Comparative Example 5, that is, a simple mixture of Compound A-33 and Compound B-43.

[0200] Rating 4 The luminous efficiency and life characteristics of the organic light-emitting devices according to Examples 3 and 4 and Comparative Examples 6 to 10 were evaluated.

[0201] The specific measurement methods are as follows, and the results are shown in Tables 9 and 10.

[0202] (1) Measurement of changes in current density in response to voltage changes The voltage of the fabricated organic light emitting device was increased from 0 V to 10 V, and the current flowing through the unit element was measured using a current-voltage meter (Keithley 2400). The measured current was divided by the area to obtain the results.

[0203] (2) Measurement of changes in brightness in response to voltage changes The voltage of the fabricated organic light emitting device was increased from 0V to 10V, and the luminance at that time was measured using a luminance meter (Minolta Cs-1000A) to obtain the results.

[0204] (3) Luminous efficiency measurement Using the luminance, current density, and voltage measured from (1) and (2), the same current density (10 mA / cm 2 The current efficiency (cd / A) of the

[0205] (4) Measurement of lifespan Luminance (cd / m 2 ) to 6000cd / m 2 The time it took for the current efficiency (cd / A) to decrease to 97% was measured and the results were obtained.

[0206] [Table 9]

[0207] [Table 10]

[0208] Referring to Tables 9 and 10, it can be seen that the organic light emitting device according to Example 3 has equivalent or improved luminous efficiency and lifetime characteristics compared to the organic light emitting devices according to Comparative Examples 6 to 8, and that the organic light emitting device according to Example 4 has equivalent or improved luminous efficiency and lifetime characteristics compared to the organic light emitting devices according to Comparative Examples 6, 9, and 10. This confirms that the organic light emitting device using an organic alloy has equivalent or improved performance compared to the organic light emitting device using a single organic compound or a simple mixture thereof.

[0209] The present invention is not limited to the above-described embodiments, and can be manufactured in various different forms, and a person skilled in the art to which the present invention pertains should understand that the present invention can be embodied in other specific forms without changing the technical concept or essential features of the present invention. Therefore, it should be understood that the above-described embodiments are illustrative in all respects and are not limiting. [Explanation of symbols]

[0210] 100, 200: Organic light-emitting element 105:Organic layer 110: Cathode 120: Anode 130: Light-emitting layer 140: Hole assist layer

Claims

1. An organic alloy of at least two organic compounds, the at least two organic compounds include a first organic compound and a second organic compound; 10 －３ torr or less, the difference in evaporation temperature between the first organic compound and the second organic compound is 20°C or less, An organic alloy for an organic optoelectronic device, wherein the organic alloy has an emission wavelength different from the emission wavelengths of the first organic compound, the second organic compound, and a simple mixture of the first organic compound and the second organic compound.

2. 10 －３ 2. The organic alloy for an organic optoelectronic device according to claim 1, wherein the difference in evaporation temperature between the first organic compound and the second compound is 0 to 10° C. at or below 100 Torr.

3. 2. The organic alloy for organic optoelectronic devices according to claim 1, wherein the maximum emission wavelength of the organic alloy is shifted by 20 nm or more from the maximum emission wavelength of a simple mixture of the first organic compound and the second organic compound.

4. The organic alloy for organic optoelectronic devices according to claim 1, wherein the color of the organic alloy has a color in a longer wavelength region than the colors of the first organic compound, the second organic compound, and a simple mixture of the first organic compound and the second organic compound.

5. 2. The organic alloy of claim 1, wherein the melting temperature (Tm) of the organic alloy is different from the melting temperature of the first organic compound, the melting temperature of the second organic compound, and the melting temperature of a simple mixture of the first organic compound and the second organic compound.

6. 10. The organic alloy of claim 1, wherein the organic alloy has a constant melting temperature (Tm).

7. The organic alloy for an organic optoelectronic device according to claim 1 , wherein the first organic compound and the second organic compound are in a liquid phase or a gas phase at an evaporation temperature.

8. 2. The organic alloy for an organic optoelectronic device according to claim 1, wherein the organic alloy is obtained by a step of liquefying or vaporizing the first organic compound and the second organic compound by heat treatment at a temperature equal to or higher than the evaporation temperature of the first organic compound and the second organic compound, and then solidifying the first organic compound and the second organic compound by cooling.

9. The organic alloy for an organic optoelectronic device according to claim 1, wherein the organic alloy is in a solid or powder form at room temperature.

10. 2. The organic alloy for an organic optoelectronic device according to claim 1, wherein the first organic compound and the second organic compound are contained in a molar ratio of 1:10 to 10:

1.

11. The organic alloy for an organic optoelectronic device according to claim 1 , wherein the first organic compound and the second organic compound are contained in a molar ratio of 1:

1.

12. 2. The organic alloy for an organic optoelectronic device according to claim 1, wherein the first organic compound is a compound having strong electronic properties, and the second organic compound is a compound having strong hole properties.

13. The first organic compound includes at least one compound represented by the following Chemical Formula 1: The second organic compound according to claim 1 includes at least one compound represented by the following chemical formula 2: The organic alloy for an organic optoelectronic device according to the present invention. 【Chemical 1】 (In the above Chemical Formula 1, Each Z is independently N or CR ａ and At least one of Z is N; R １ ~R １０ and R ａ are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C12 aryl group, or a combination thereof; In Formula 1, the total number of 6-membered rings substituted with triphenylene groups is 6 or less; L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group; n1 to n3 each independently represent 0 or 1; n1+n2+n3≧1.) 【Chemistry 2】 (In the above chemical formula 2, Y １ and Y ２ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof; Ar １ and Ar ２ are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof; R １１ ~R １３ and R ４３ ~R ４４ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, or a combination thereof.

14. The organic alloy for an organic optoelectronic device according to claim 13, wherein the first organic compound is represented by the following chemical formula 1-I or 1-II: 【Chemistry 3】 (In the above chemical formula 1-I or 1-II, Each Z is independently N or CR ａ and At least one of Z is N; R １ ~R １０ and R ａ are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C12 aryl group, or a combination thereof; In Formula 1-I and Formula 1-II, the total number of 6-membered rings substituted with triphenylene groups is 6 or less; L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group; n1 to n3 each independently represent 0 or 1; n1+n2+n3≧1.)

15. 14. The organic alloy for an organic optoelectronic device according to claim 13, wherein L in Chemical Formula 1 is a single bond, a substituted or unsubstituted phenylene group with a kink structure, a substituted or unsubstituted biphenylene group with a kink structure, or a substituted or unsubstituted terphenylene group with a kink structure.

16. 14. The organic alloy for an organic optoelectronic device according to claim 13, wherein L in Formula 1 is a single bond or one selected from the substituted or unsubstituted groups listed in Group 1 below. 【Chemistry 4】 (In the above Group 1, R １５ ~R ４２ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroarylamine group, a substituted or unsubstituted C1 to C30 alkoxy group, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof.

17. Ar in Formula 2 １ and Ar ２ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

18. The first organic compound is at least one of the compounds listed in Group A below, The organic alloy for an organic optoelectronic device according to claim 13, wherein the second organic compound is at least one of the compounds listed in the following Group B: 【Chemistry 5】

19. an anode and a cathode facing each other; at least one organic layer located between the anode and the cathode; Including, An organic optoelectronic device, wherein the organic layer comprises the organic alloy according to any one of claims 1 to 18.

20. 20. A display device comprising the organic optoelectronic device of claim 19.

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