Organic material for an organic electronic element, method for producing an organic material for an organic electronic element, and organic electronic element using the organic material

Abstract

Embodiments of the present invention relate to an organic material for an organic electronic element, which can improve driving voltage, luminous efficiency, and lifespan characteristics of the organic electronic element, a method of producing an organic material for an organic electronic element, and an organic electronic element using the organic material.

Description

TECHNICAL FIELD

[0001] Embodiments of the present application relate to an organic material for an organic electronic element, a method of producing an organic material for an organic electronic element, and an organic electronic element using the organic material. BACKGROUND

[0002] Large-scale displays in the current portable display market require more power than that consumed in conventional portable displays. Accordingly, power consumption becomes a critical factor for portable displays having a limited power source (e.g., a battery), and life span and efficiency problems should be addressed.

[0003] Such displays mainly include an organic electronic element.

[0004] An organic electronic element using an organic light emitting phenomenon typically has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer typically has a multi-layer structure composed of different materials (e.g., a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer) to improve efficiency and stability of the organic electronic element.

[0005] The organic material layer can be deposited by various processes. The power consumption, efficiency, and life span of the organic electronic element can vary depending on the conditions of the deposition process (e.g., the organic material used in the deposition process). SUMMARY

[0006] TECHNICAL PROBLEM

[0007] Embodiments of the present application can provide an organic material for an organic electronic element, a method of producing an organic material for an organic electronic element, and an organic electronic element using the organic material, which can enhance driving voltage, light emitting efficiency, and life span characteristics of the organic electronic element.

[0008] TECHNICAL SOLUTION

[0009] In an aspect, embodiments of the present application can provide a method of preparing an organic material for an organic electronic element, the method including: a first step of preparing a first material including a first raw material and a second raw material; a second step of obtaining a second material by pulverizing the first material; and a third step of selecting a granular organic material from the second material, a partial region or an entire region of a surface of the organic material having a needle shape, and can further provide an organic electronic element using the organic material.

[0010] On the other hand, embodiments of the present application can provide an organic material for an organic electronic element, the organic material including at least one raw material, wherein a partial region or an entire region of a surface of the organic material has a needle shape, and wherein the organic material has a granular form, and can also provide an organic electronic element using the organic material.

[0011] Advantages

[0012] According to embodiments of the present application, an organic material for an organic electronic element, a method of producing an organic material for an organic electronic element, and an organic electronic element using the organic material, which can achieve a reduced driving voltage, high light emission efficiency, and long lifespan of an organic electronic element by forming an organic electronic element using the organic material, can be provided. BRIEF DESCRIPTION OF DRAWINGS

[0013] Figure 1 is a flowchart illustrating a method of producing an organic material according to embodiments of the present application;

[0014] Figure 2 is a diagram illustrating a step of selecting an organic material according to embodiments of the present application;

[0015] Figure 3 is a diagram illustrating a mixture according to embodiments of the present application;

[0016] Figure 4 is an exemplary diagram illustrating an organic light emitting element according to embodiments of the present application;

[0017] Figure 5 is a graph illustrating a degree of gas generation depending on pressure and temperature changes of an organic material according to embodiments;

[0018] Figure 6 is a graph illustrating a degree of gas generation depending on pressure and temperature changes of an organic material according to comparative examples of the present application;

[0019] Figure 7 is a graph illustrating results of qualitative analysis of gases generated from organic materials according to comparative examples and embodiments;

[0020] Figure 8 is an image of a surface of an organic material according to embodiments of the present application; and

[0021] Figure 9 is an image of a surface of an organic material according to comparative examples. DETAILED DESCRIPTION

[0022] Hereinafter, some embodiments of the present application are described in detail with reference to the accompanying drawings. In the entire specification and drawings, the same or substantially similar components are denoted by the same reference numerals throughout the specification. Details of known technology or functions can be omitted when it is determined that the subject matter of the present application is disclosed unnecessarily. The terms "comprise" and / or "include", "have", and / or "contain", "comprising" and / or "including", "have" and / or "contain" are used in the specification to specify the presence of stated features, regions, integers, steps, operations, elements, and / or components, and do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and / or groups thereof. As used herein, the singular forms "a", "an", and "the" also include the plural forms unless the context clearly dictates otherwise.

[0023] "First", "second", "A", "B", "(a)", and "(b)" and the like represent components that can be used to describe the present application. These representations are provided only to distinguish one component from another component, and the essence of the components is not limited by the order or sequence in the representation.

[0024] When describing the positional relationship between components, when two or more components are described as being "connected", "coupled", or "linked", the two or more components can be directly "connected", "coupled", or "linked", or other components can be interposed therebetween. Here, the other components can be included in one or more of the two or more components that are "connected", "coupled", and "linked" to each other.

[0025] For components, operation methods, or manufacturing methods, when A is referred to as "after", "behind", and "before" B, A and B can not be continuous to each other unless the words "immediately" or "directly" are used.

[0026] When a component is assigned a value or its corresponding information, the value or corresponding information can be interpreted to include a tolerance that can be generated due to various factors (e.g., process factors, internal or external influences, or noise).

[0027] The specific processing order can be different from the described order when the embodiments can be implemented in other ways. For example, two processes described as being consecutive can be performed substantially simultaneously or in reverse order.

[0028] Figure 1 is a flowchart illustrating a method for producing an organic material according to an embodiment of the present application.

[0029] Figure 2 is a diagram illustrating a step of selecting an organic material according to an embodiment of the present application. Figure 3 is a diagram illustrating a formation state of an organic material according to an embodiment of the present application.

[0030] Reference Figure 1 A method for producing an organic material according to an embodiment of the present application includes a first step (S11) of preparing a first material including at least one raw material.

[0031] The first material can be prepared using one raw material.

[0032] The raw material for preparing the first material can include at least one organic material, but the present application is not limited thereto. Here, the raw material for preparing the first material can be in a powder form (or can be referred to as a powder form).

[0033] In the present application, the raw material can be a material including at least one of an amino-containing compound, an azide-containing compound, and a polycyclic-containing compound, but the present application is not limited thereto.

[0034] The first material of the present application can include two or more raw materials.

[0035] For example, the first material can be prepared from a first raw material and a second raw material.

[0036] At least one of the first raw material and the second raw material included in the first material can include at least one organic material, but the present application is not limited thereto.

[0037] In this case, the first step can include melting each of the first raw material and the second raw material, and then physically mixing the solidified first raw material and the first raw material.

[0038] However, the present application is not limited thereto, and as another example, the first material can include a third raw material and a fourth raw material.

[0039] In this case, the first step can include physically mixing the third raw material and the fourth raw material, and then melting the mixed third and fourth raw materials. Here, at least one of the third raw material and the fourth raw material can include at least one organic material, but the present application is not limited thereto.

[0040] Each raw material can be mixed in the atmosphere or can be mixed while being blocked from moisture. In this case, the first raw material and the second raw material can be mixed in a weight ratio of 1:1 to 1:9 or 1:1 to 9:1, and preferably in a ratio of 1:1. In addition, the third raw material and the fourth raw material can also be mixed in a weight ratio of 1:1 to 1:9 or 1:1 to 9:1, but the present application is not limited thereto, and the relative weight ratio of the raw materials can vary.

[0041] When each of the raw materials is melted in an environment exposed to moisture and oxygen, impurities can be included. Accordingly, the melting process can be performed in a vacuum state, but the melting process of the present application is not limited thereto.

[0042] The melting process of the first step can include a step of temperature-treating each of the raw materials.

[0043] The melting process can include heat-treating each of the first raw material and the second raw material, or physically mixing the first raw material and the first raw material, and then heat-treating the mixed materials.

[0044] The temperature during the heat-treating step of the melting process can be selected from a temperature 50°C to 70°C lower than a temperature at which the weight of the raw material is reduced by 0.5% when the pyrolysis temperature (Td) of the raw material is measured (hereinafter referred to as a heat-treating temperature).

[0045] Specifically, when the first step is performed by melting each of the first raw material and the second raw material, solidifying the first raw material and the second raw material, and then physically mixing the first raw material and the second raw material, the first raw material and the second raw material can be heat-treated at different heat-treating temperatures.

[0046] Further, when the first step is performed in the order of physically mixing the third raw material and the fourth raw material, then melting the mixed third and fourth raw materials, and then solidifying them, the heat-treating process can be performed at a higher heating temperature among the heat-treating temperature of the third raw material and the heat-treating temperature of the fourth raw material. In other words, when two or more raw materials are used to form the first material, and the two or more raw materials are physically mixed and then heat-treated at the same time, a higher heat-treating temperature among the respective heat-treating temperatures of the raw materials can be selected, and the heat-treating step of the melting process can be performed.

[0047] Further, in the temperature-treating step, the pressure can be selected in the range of 10 -6 to 10 -3 Torr.

[0048] In the heat-treating step, when heat is applied to the raw material, all or a part of the raw material can pass through a liquid state to generate an impurity gas.

[0049] As described above, the raw material that has undergone the heat-treating step can be solidified at a lower temperature than the temperature of the heat-treating step. For example, the raw material that has undergone the melting process can be solidified at room temperature, but the present application is not limited thereto.

[0050] Thereafter, the first material solidified through the melting process to prepare the second material (S12) is pulverized. Next, the organic material (S13) is selected from the pulverized second material.

[0051] The selected organic material can be in the form of particles (fine particles) of which a part of the area or the entire area of the surface is needle-shaped.

[0052] Reference will now be made to Figure 2 The process of selecting the organic material will be discussed in detail.

[0053] Reference will now be made to Figure 2 The pulverized second material 200 can be separated into the organic material 250 and the residue 270 by the separator 210.

[0054] The separator 210 can include a first filter 220 and a second filter 230 disposed on the first filter 220 and spaced apart from the first filter 220. Here, the particle size X of the first filter 220 can be smaller than the particle size Y of the second filter 220. For example, the particle size X of the first filter 220 can be 0.1 mm, and the particle size Y of the second filter 230 can be 0.5 mm or less. First, the pulverized second material 200 can pass through the second filter 230 of the separator 210. For example, when the particle size Y of the second filter 220 is 0.5 mm, only fine particles having a particle size of 0.5 mm or less among the pulverized second material 200 can pass through the second filter 230. Fine particles having a particle size exceeding 0.5 mm among the pulverized second material 200 do not pass through the second filter 230, but are left on the second filter 230.

[0055] Among the fine particles passing through the second filter 230, fine particles having a particle size of 0.1 mm or less can pass through the first filter 220. Fine particles not passing through the first filter 220 are left on the first filter 220.

[0056] The fine particles left on the first filter 220 can be fine particles corresponding to the organic material 250. The fine particles passing through the first filter 220 can be the residue 270.

[0057] The size of the fine particles constituting the organic material 250 can exceed 0.1 mm and be equal to or less than 0.5 mm. The size of the residue 270 can be 0.1 mm or less.

[0058] The organic material 250 including fine particles having a size exceeding 0.1 mm and being equal to or less than 0.5 mm can be formed into a specific shape.

[0059] For example, as shown in FIG. 2, Figure 3 The organic material 250 can be compressed to be formed into a formed body 300 in the shape of a disc or a polygon, but the present application is not limited thereto.

[0060] The formation body 300 of the organic material 250 can be used in a process of forming an organic electronic element.

[0061] The structure of an organic electronic element according to an embodiment of the present application will be discussed below with reference to Figure 4

[0062] Figure 4 is an exemplary diagram illustrating an organic light emitting element according to an embodiment of the present application.

[0063] The organic electronic element 400 according to an embodiment of the present application can include a first electrode 410 formed on a substrate, a second electrode 470, and an organic material layer between the first electrode 410 and the second electrode 470, the organic material layer including a compound according to the present application, and can further include or not include a capping layer 480.

[0064] Figure 1 The first electrode 410 can be an anode, and the second electrode 470 can be a cathode. In a reverse type, the first electrode can be a cathode, and the second electrode can be an anode.

[0065] The organic material layer can include a hole injection layer 420, a hole transport layer 430, a light emitting layer 440, an electron transport layer 450, and an electron injection layer 460. Specifically, the hole injection layer 420, the hole transport layer 430, the light emitting layer 440, the electron transport layer 450, and the electron injection layer 460 can be sequentially disposed on the first electrode 410.

[0066] Meanwhile, although not shown in Figure 1 An electron transport auxiliary layer or a buffer layer can be further disposed between the light emitting layer 440 and the electron transport layer 450.

[0067] The formation body 300 of the organic material 250 of the present application can be used as a material for forming the hole injection layer 420, the hole transport layer 430, the light emitting layer 440, the electron transport layer 450, or the electron injection layer 460. For example, the formation body 300 of the organic material 250 of the present application can be used as a host material of the light emitting layer 440.

[0068] ​The organic electronic element 400 according to an embodiment of the present application can be manufactured by various deposition methods. The organic electronic element 400 can be manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate to form the anode 410 using a deposition method such as physical vapor deposition (PVD) or chemical vapor deposition (CVD), forming an organic material layer including the hole injection layer 420, the hole transport layer 430, the light emitting layer 440, the electron transport layer 450, and the electron injection layer 460 on the anode 410, and then depositing a material that can be used as the cathode 470 on the organic material layer.

[0069] Therefore, in manufacturing the organic electronic element 400, a deposition process is an essential process.

[0070] During the deposition process, the organic material for the organic electronic element is deposited on the substrate by applying a specific temperature at a specific pressure. At this time, a gas can be generated depending on the shape of the organic material for the organic electronic element. The gas can contaminate the inside of the deposition machine (e.g., the inside of a chamber), adversely affect the organic electronic element, and shorten the life of the deposition machine.

[0071] As described above, the method of manufacturing the organic material 250 for the organic electronic element according to the present application includes a step of obtaining the second material through a melting process of the first material. After the melting process, a process of pulverizing the solidified second material is performed.

[0072] Depending on the size of the fine particles, the pulverized second material can be classified into a powder form and a granular form. The organic material manufactured through the organic material manufacturing method according to the present application has a granular form. A compound for an organic electronic element formed of an organic material containing only fine particles in a granular form can offset gas emission, preventing degradation of the performance of the organic electronic element and the deposition machine.

[0073] Here, the granular fine particles refer to fine particles having a size of a particle diameter exceeding 0.1 mm and equal to or less than 0.5 mm.

[0074] The organic material 250 for the organic electronic element according to the present application can be manufactured by an organic material manufacturing method including fine particles in a granular form and having a particle diameter of a size exceeding 0.1 mm and equal to or less than 0.5 mm.

[0075] However, the organic material for an organic electronic element formed of a powder type fine particle having a smaller particle diameter than the granular fine particle (corresponding to the composition of the residue) has a larger volume at the same mass than the organic material for an organic electronic element 250 of the present application prepared from the granular fine particle. This means that the density of the organic material prepared in the form of a powder fine particle is lower than that of the organic material for an organic electronic element 250 of the present application. The low-density organic material has a larger surface area exposed to air than the high-density organic material 250 of the present application.

[0076] The increase in the surface area of the organic material means an increase in the area combined with impurities, and as the number of impurities combined to the surface of the organic material increases, the number of gases generated from the organic material during deposition increases.

[0077] In other words, since the organic material prepared in the form of a powder contains more impurities than the organic material for an organic electronic element 250 of the present application, it can contaminate the inside of a deposition machine and reduce the performance of the organic electronic element and the deposition machine during the deposition process of the organic electronic element.

[0078] The following compares the number of gas emissions between the organic material prepared in the form of a powder fine particle (hereinafter referred to as the organic material according to the comparative example) and the organic material for an organic electronic element of the present application.

[0079] Figure 5 is a graph showing the degree of gas generation depending on the pressure and temperature changes of the organic material according to the embodiment. Figure 6 is a graph showing the degree of gas generation depending on the pressure and temperature changes of the organic material according to the comparative example.

[0080] In Figure 5 and Figure 6 , the x-axis represents the elapsed time, and the y-axis represents the pressure (solid line) and the temperature (dotted line).

[0081] Referring to Figure 5 , in the case of the organic material according to the embodiment, it can be seen that a slight pressure change occurs when 750 seconds elapses. In the experiment, the temperature was set to converge to 375°C as time passes. The convergence temperature is an arbitrary temperature set to identify whether gas is generated depending on the temperature, and the convergence temperature can vary depending on the type of raw material.

[0082] It can be seen that the change in the proportion of the organic material according to the present embodiment occurs at the time of the change in pressure (for example, the elapsed time is between 750 seconds and 900 seconds). In this case, it can be seen that the change in pressure occurs due to the gas generated from the organic material according to the present embodiment. Here, the amplitude of the change in pressure of the organic material according to the present embodiment can correspond to the amount of gas generated from the organic material according to the present embodiment.

[0083] Reference Figure 6 It can be seen that, in the case of the organic material according to the comparative example, a large change in pressure occurs when 1100 seconds elapses. Also, as in the present embodiment, in the experiment, the temperature was set to converge to 375°C over time. The convergence temperature is an arbitrary temperature set to identify whether gas is generated depending on the temperature, and the convergence temperature can change depending on the type of raw material.

[0084] It can be seen that the change in the proportion of the organic material according to the comparative example occurs mainly at the time of the change in pressure (for example, the elapsed time is between 1100 seconds and 1300 seconds). Here, the amplitude of the change in pressure of the organic material according to the comparative example can correspond to the amount of gas generated from the organic material according to the comparative example.

[0085] According to Figure 5 and Figure 6 The time at which the pressure of the organic material according to the present embodiment and the comparative example changes can change depending on, for example, the amount and type of the organic material used in the experiment.

[0086] In Figure 5 and Figure 6 , the amount of the organic material according to the present embodiment and the amount of the organic material according to the comparative example used in the experiment are the same, and it can be seen that the amplitude of the pressure changed by applying heat to the organic material according to the present embodiment is smaller than the amplitude of the pressure changed by applying heat to the organic material according to the comparative example.

[0087] In other words, it can be seen that the amount of gas generated from the organic material according to the present embodiment is significantly smaller than the amount of gas generated from the organic material according to the comparative example. It can be seen that the organic material according to the comparative example, which includes a powder having a smaller size than the particles of the material included in the organic material according to the present embodiment, emits more gas at a temperature higher than room temperature than the organic material according to the present embodiment.

[0088] Figure 7 is a graph showing the results of a qualitative analysis of the gas generated from the organic materials according to the comparative example and the present embodiment.

[0089] The types of gases generated from the organic material according to the comparative example and the embodiment can be predicted by a residual gas analyzer (RGA).

[0090] In Figure 7 In the graph, the x-axis represents time, and the y-axis represents partial pressure.

[0091] Referring to Figure 7 It can be seen that gases including N, CH2, CH3, C2H3, Al, HCN, N2, CO, C2H4, Si, C3H6, C3H7, and CH3CO were generated from the organic material according to the comparative example (gases generated due to impurities included in the organic material according to the comparative example). On the other hand, it can be seen that gases such as N, CH2, and CH3 were generated from the organic material according to the embodiment (gases generated due to impurities included in the organic material according to the embodiment). In other words, it can be seen that the number of impurities included in the organic material according to the comparative example is greater than the number of impurities included in the organic material according to the embodiment.

[0092] Figure 7 CH2, CH3, C2H3, CO, C2H4, C3H6, C3H7, and CH3CO can be empirical formulas (simply representing the ratio of each element). N and N2 can be gases generated from the organic material or atmospheric gases used in the analysis process using the residual gas analyzer.

[0093] Therefore, as Figure 7 shown in the graph, it can be seen that the types of gases generated from the organic material according to the comparative example are more than the types of gases generated from the organic material according to the embodiment, and the pressure change due to the gases generated from the organic material according to the comparative example is greater than the pressure change due to the gases generated from the organic material according to the embodiment.

[0094] Referring to Figures 5 to 7 It can be seen that even for the same compound, the content of the gases generated at the same temperature and the same pressure differs greatly. Since the number and types of gases generated from the organic material according to the embodiment are significantly smaller than the number and types of gases generated from the organic material according to the comparative example, in the case of preparing an organic electronic element using the organic material according to the embodiment, it is possible to suppress performance degradation due to the organic material according to the embodiment.

[0095] On the contrary, if a high temperature is applied at room temperature, the organic material according to the comparative example generates a large amount of gases including CH2, CH3, C2H3, Al, HCN, CO, C2H4, Si, C3H6, C3H7, and CH3CO, which can affect the properties of the organic electronic element.

[0096] Subsequently, reference is made to Figure 8 and Figure 9 A comparison between surface properties of the organic material according to the present embodiment and the organic material according to the comparative example is described.

[0097] Figure 8 is a surface image of the organic material according to the present embodiment, Figure 9 is a surface image of the organic material according to the comparative example.

[0098] Figure 8 and Figure 9 are scanning electron microscope (SEM) images (magnification 10000x) of respective surfaces of the organic material.

[0099] Reference is made to Figure 8 It can be seen that the surface of the organic material according to the present embodiment has a needle-like surface structure.

[0100] On the other hand, reference is made to Figure 9 It can be seen that the surface of the organic material according to the comparative example has an irregular shape.

[0101] In other words, although prepared from the same raw materials, the organic material according to the present embodiment and the organic material according to the comparative example can have different surface shapes.

[0102] A comparison between properties of an organic electronic element comprising the organic material according to the present embodiment and an organic electronic element comprising the organic material according to the comparative example is made below.

[0103] Evaluation of the preparation of the organic electronic element

[0104] [Example 1] Red organic light-emitting element (light-emitting auxiliary layer)

[0105] According to a typical method, an organic electronic element was prepared using the organic material of the present application obtained by the above-described method as a light-emitting auxiliary layer material. First, a film of N1-(naphthalene-2-yl)-N4,N4-bis(4-(naphthalene-2-(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) was vacuum-deposited to a thickness of 60 nm on an ITO layer (anode) formed on a glass substrate as a hole injection layer. Subsequently, N,N'-bis(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter referred to as NPB) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. Subsequently, the organic material 1 in the form of particles according to an embodiment of the present application (hereinafter referred to as the organic material according to the present embodiment) was vacuum-deposited to a thickness of 20 nm as a light-emitting auxiliary layer material to form a light-emitting auxiliary layer material. After the light-emitting auxiliary layer was formed, a 30-nm-thick light-emitting layer was deposited on the light-emitting auxiliary layer using CBP [4,4'-N,N'-dicarbazolebiphenyl] as a host and (piq)2Ir(acac) [bis-(1-phenylisoquinolyl)iridium(2ate] doped as a dopant in a weight ratio of 95:5. (1,1'-Biphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter referred to as BAIq) was vacuum-deposited to a thickness of 10 nm as a hole blocking layer, and a film of tris(8-quinolinato)aluminum (hereinafter referred to as AIq3) was formed to a thickness of 40 nm as an electron transport layer. Then, an alkali metal halide LiF was deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as a cathode to prepare an organic light-emitting element.

[0106] [Organic material 1 according to the present embodiment]

[0107]

[0108] [Examples 2 to 5]

[0109] An organic electronic element was prepared by the same method as in Example 1, except that the organic materials 2 to 5 according to embodiments of the present application described below were used instead of the organic material 1 according to an embodiment of the present application as a light-emitting auxiliary layer material.

[0110]

[0111] [Comparative Examples 1 to 5]

[0112] An organic electronic element was prepared by the same method as in Example 1, except that a powdery compound was used instead of a particulate organic material as a light-emitting auxiliary layer material.

[0113] A forward bias DC voltage was applied to the organic electronic devices prepared according to Examples 1 to 5 and Comparative Examples 1 to 5 of the present invention, and the electroluminescence (EL) characteristics were measured using a PR-650 from Photo Research Inc., and the lifetime was measured at 2500 cd / m² using a lifetime meter manufactured by Mcscience Inc. 2 The T95 lifetime was measured at a reference brightness. The measurement results are shown in Table 1 below. In Table 1, the numbers marked after the organic material powder and particles are used to distinguish the types of powders and particles applied to the various comparative examples and embodiments.

[0114] [Table 1]

[0115]

[0116] [Example 6] Red organic light-emitting element (phosphorescent host)

[0117] According to a typical method, organic electronic components are fabricated using synthesized organic materials as the host material for light emission. First, a 60 nm thick hole injection layer is formed by vacuum deposition of N1-(naphthyl-2-yl)-N4,N4-bis(4-(naphthyl-2-(phenyl)amino)phenyl)-N1-phenylphenyl-1,4-diamine (abbreviated as 2-TNATA) films on an ITO layer (anode) formed on a glass substrate. Then, a 60 nm thick hole transport layer is formed by depositing 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as -NPD) as the hole transport compound on the hole injection layer. On the hole transport layer, an organic material 6 is used as the host material and doped with (piq)2Ir(acac)[bis-(1-phenylisoquinolinyl)acetylacetoneiridium(III)] at a weight ratio of 95:5 to form a 30 nm thick light emission layer. Subsequently, a 10 nm thick layer of (1,1'-diphenyl)-4-oleic acid bis(2-methyl-8-quinolineoleic acid) aluminum (hereinafter referred to as BAlq) was deposited under vacuum as a hole-blocking layer, and a 40 nm thick layer of tri(8-quinolineol) aluminum (hereinafter referred to as Alq3) film was formed as an electron transport layer. Then, an alkali metal halide LiF was deposited as an electron injection layer to a thickness of 0.2 nm, and finally, Al was deposited to a thickness of 150 nm and used as a cathode to fabricate organic electronic components.

[0118] [Organic material 6 according to this embodiment]

[0119]

[0120] [Examples 7 to 9]

[0121] An organic electronic element was produced by the same method as in Example 6, except that the compound of the present application described below was used instead of the organic material 6 according to the embodiment of the present application as the host material of the light-emitting layer.

[0122]

[0123] [Organic material 9 according to the present embodiment]

[0124]

[0125] [Examples 10 to 17]

[0126] An organic electronic element was produced by the same method as in Example 6, by simply mixing (physically mixing) one of the organic materials 6 to 9 according to the embodiments and another material (or a heterogeneous compound) in a weight ratio of 5:5 as the host material of the light-emitting layer. The heterogeneous mixture is shown in Table 2.

[0127] [Examples 18 to 25]

[0128] An organic electronic element was produced by the same method as in Example 6, by mixing a raw material having the same structural formula as each of the organic materials 6 to 9 according to the embodiments of the present application and a heterogeneous compound in a weight ratio of 5:5 to form an organic material as the host material of the light-emitting layer, and subjecting them to heat treatment (sublimation refining, physically mixing the materials, and then melting) to form an organic material, and then by the same method as in Example 6. The other material (or a heterogeneous compound) is shown in Table 2.

[0129] [Comparative Examples 6 to 25]

[0130] An organic electronic element was produced by the same method as in Example 6, except that a powdery organic material was used instead of a granular organic material as the light-emitting layer material.

[0131] [Comparative Examples 26 to 29]

[0132] An organic electronic element was produced by the same method as in Example 6, except that the state of the heterogeneous compound of the present application as the light-emitting layer material was applied only to one of a granular compound or a powdery compound and used.

[0133] A forward bias DC voltage was applied to the organic electronic elements produced according to Examples 6 to 26 and Comparative Examples 6 to 26, electroluminescence (EL) characteristics were measured using PR-650 by Photo Research Inc., and the lifetime was measured at 2500 cd / m2by a lifetime meter manufactured by Mcscience Inc. 2T95 lifetime was measured for the measurement results under a reference luminance of 1000 cd / m2. Table 2 below shows the results of the element preparation and evaluation. In Table 2, the numbers marked after the powder and particles of the first and second materials are used to distinguish the types of powder and particles applied to each of the comparative examples and embodiments.

[0134] [Table 2]

[0135]

[0136]

[0137]

[0138] [Example 26] Green Organic Light Emitting Element (Electron Transporting Layer)

[0139] An organic electronic element was prepared by a typical method using the organic material according to the embodiment of the present application as an electron transporting layer material. First, 4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter referred to as 2-TNATA) was vacuum-deposited to a thickness of 60 nm on an ITO layer (anode) formed on a glass substrate to form a hole injecting layer, and 4,4-bis[N-(l-naphthyl)-N-phenylamino]biphenyl (hereinafter referred to as NPD) was vacuum-deposited to a thickness of 60 nm on the hole injecting layer to form a hole transporting layer. Subsequently, 4,4'-N,N'-dicarbazole biphenyl (hereinafter referred to as CBP) as a host material and tris(2-phenylpyridine)iridium (hereinafter referred to as Ir(ppy)3) as a dopant were doped in a weight ratio of 95:5 on the hole transporting layer to deposit a 30-nm-thick light emitting layer. Thereafter, (l,l'-diphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter referred to as BAIq) was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and the organic material according to the embodiment was vacuum-deposited to a thickness of 40 nm on the hole blocking layer to form an electron transporting layer. After that, an alkali metal halide LiF was deposited to a thickness of 0.2 nm on the electron transporting layer to form an electron injecting layer, and Al was deposited to a thickness of 150 nm to form a cathode, thereby preparing an organic electronic element.

[0140] [Organic Material 10 According to the Embodiment]

[0141]

[0142] [Examples 27 to 28]

[0143] An organic electronic element was prepared by the same method as in Example 26, except that the following organic materials 11 and 12 according to the embodiments of the present application were used instead of the organic material 10 according to the embodiment of the present application as an electron transporting layer material.

[0144]

[0145] [Comparative Examples 30-32]

[0146] An organic electronic element was prepared by the same method as in Example 26, except that a powdery organic material was used instead of a granular organic material as the electron transport layer material.

[0147] A forward-biased DC voltage was applied to the organic electronic elements prepared according to Examples 26 to 28 and Comparative Examples 30 to 32, electroluminescence (EL) characteristics were measured using a PR-650 by Photo Research Inc., and T95 lifetimes were measured for the measurement results at a reference luminance of 5000 cd / m2by a lifetime meter manufactured by Mcscience Inc. Table 3 below shows the measurement results. In Table 3, the numbers marked after the powders and granules of the organic materials are used to distinguish the types of powders and granules applied to each of the comparative examples and examples. 2

[0148] [Table 3]

[0149]

[0150] As can be seen from the results of the elements, depending on the granular organic material according to the examples of the present application and the powdery organic material according to the comparative examples, that is, depending on the form of the organic material, different results of the driving, efficiency, and lifetime of the organic electronic element can be obtained.

[0151] As can be seen, the element characteristics are different because the organic material contains different impurity contents depending on its form. Referring back to Figure 7 , it can be seen that the content of impurities contained in the organic material according to the comparative examples, which is in a powder form, is greater than the content of impurities contained in the organic material according to the present examples, which is in a granular form, so that the types and amounts of gases generated from the organic material according to the comparative examples are greater than those generated from the organic material according to the present examples.

[0152] Referring to Figure 7 and the results of the elements according to the above examples and comparative examples, it can be determined that the results of the elements are affected more by the form of the applied organic material than by the degree of influence of the type of the organic material and the applied layer. Specifically, by comparing the results of applying the organic material according to the examples of the present application and the organic material according to the comparative examples to the light-emitting layer, it can be recognized that as the content of the granular organic material as the organic material applied to the light-emitting layer increases, the results of the elements are improved (the driving voltage is reduced).

[0153] ​In other words, it can be determined that as the content of impurities of the organic material used to form the light-emitting layer decreases, the characteristics of the organic electronic element are enhanced.

[0154] The above-described embodiments are merely examples, and those of ordinary skill in the art will understand that various changes can be made thereto without departing from the scope of the present application. Accordingly, the embodiments set forth herein are presented for the purpose of illustration and are not restrictive of the scope of the present application, and it should be understood that the scope of the present application is not limited by the embodiments. The scope of the present application should be interpreted by the following claims, and all technical spirits within equivalents thereof should be interpreted as belonging to the scope of the present application.

[0155] [Reference Number Legend]

[0156] 200: second material

[0157] 210: separator

[0158] 220: first filter

[0159] 230: second filter

[0160] 250: organic material

[0161] 270: residue

[0162] Cross Reference to Related Applications

[0163] This patent application claims priority under 35 U.S.C. 119(a) to Korean Patent Application No. 10-2020-0086374, filed on July 13, 2020, in the Korean Intellectual Property Office, the disclosure of which is incorporated herein by reference. This patent application claims priority to other applications filed in other countries, the disclosures of which are also incorporated herein by reference.

Claims

1. A method of producing an organic material for an organic electronic element, the method comprising: a first step of producing a first material including at least one raw material; a second step of obtaining a second material by pulverizing the first material; and a third step of selecting a granular organic material from the second material, a part of an area or an entire area of a surface of the organic material having a needle shape, wherein the first material includes a first raw material and a second raw material, and wherein the first step includes: melting each of the first raw material and the second raw material; solidifying the melted first raw material and the melted second raw material; and mixing the first raw material and the second raw material. The particle diameter of the organic material is greater than 0.1 mm and equal to or less than 0.5 mm.

2. The method of claim 1, wherein, The third step includes passing the second material through a separator having a first filter and a second filter disposed on the first filter and spaced apart from the first filter, the particle diameter of the second filter being greater than the particle diameter of the first filter.

3. The method of claim 1, wherein, The organic material corresponds to a material remaining on the first filter.

4. The method of claim 3, wherein, The particle diameter of the first filter is 0.1 mm or less, and the particle diameter of the second filter is 0.5 mm or less.

5. The method of claim 3, wherein, 6. The method according to claim 1, further comprising a step of shaping the organic material.

7. A method of producing an organic material for an organic electronic element, the method comprising: a first step of producing a first material including at least one raw material; a second step of obtaining a second material by pulverizing the first material; and a third step of selecting a granular organic material from the second material, a part of an area or an entire area of a surface of the organic material having a needle shape, wherein the first material includes a third raw material and a fourth raw material, and wherein the first step includes: mixing the third raw material and the fourth raw material; and melting and subsequently solidifying the mixed third raw material and fourth raw material. The third step includes passing the second material through a separator having a first filter and a second filter disposed on the first filter and spaced apart from the first filter, the particle diameter of the second filter being greater than the particle diameter of the first filter. The organic material corresponds to a material remaining on the first filter.

8. The method of claim 7, wherein, The particle diameter of the first filter is 0.1 mm or less, and the particle diameter of the second filter is 0.5 mm or less.

9. The method of claim 8, wherein, 11. The method according to claim 7, further comprising a step of shaping the organic material.

10. The method of claim 8, wherein, ​ ​

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