KR102382285B1 - Compound for organic electronic element having benzocyclobutene functional group for cross-linked bond, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention is an organic compound for forming an organic thin film disposed between a first electrode and a second electrode of an organic electric device, and comprises at least one benzocyclobutene group at the end thereof.

Description

A compound for an organic electrical device having a cross-linkable benzocyclobutene group, an organic electrical device using the same, and an electronic device thereof THEREOF}

The present invention relates to an organic chemical composition for use in OLED applications, and more particularly, to a compound for an organic electric device having a cross-linkable benzocyclobutene group, an organic electric device using the same, and an electronic device thereof.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic electric device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

A material used as an organic layer in an organic electric device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function.

The term 'organic electronic device' used in the present invention includes an organic integrated circuit (OIC), an organic field-effect transistor (OFET), an organic thin film transistor (OTFT), an organic light emitting transistor (OLET), an organic solar cell (OSC), It is defined to include organic photodetectors, organic photoreceptors, organic electro-quenching devices (OFQDs), organic light emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) and organic electroluminescent devices (OLEDs), and the like.

The present invention is particularly interested in providing novel organic compounds for use in organic electric devices referred to as OLEDs. The general structure of OLEDs and their functional principles are well known to the person skilled in the art and are described in particular in US 4539507, US 5151629, EP 0676461 and WO 1998/27136.

OLED (organic photoelectric device), which is attracting attention as a next-generation display device, forms an organic light emitting layer between a substrate coated with a transparent anode material such as ITO and a cathode. It is a device using the principle that electrons combine in an organic light emitting layer to emit light. OLEDs are receiving increasing attention for their applications in electronic devices such as flat panel displays, lighting and backlighting. OLED technology is described in Geffroy et al., "Organic Light Emitting Diode (OLED) Technology: Materials Devices and Display Technologies," Polym, Int., 55:572-582 (2006), and in US Pat. Nos. 5,844,363, 6,303,238 and 5,707,745, the various OLED materials and configurations described, all of which are incorporated herein by reference.

An organic electroluminescent device (OLED) has a multilayer structure including a charge blocking layer according to the characteristics of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and a light emitting layer in addition to an organic light emitting layer in order to realize industrially applicable level of performance. is made with

In the prior art, each layer constituting an organic electric device (particularly, OLED) is generally formed by a vacuum deposition process. Japanese Patent Laid-Open No. 2006-156847 (Patent Document 1) discloses an organic compound and a technique for manufacturing an organic electric device including an organic film having a single-layer structure by depositing the same on a substrate by vacuum deposition. The vacuum deposition method is a principle of forming a thin film by applying heat to a sample in a high vacuum atmosphere of 10 ^-4 Torr or less to sublimate it, and the sublimated sample is grown as a solid on a substrate at a relatively low temperature. However, in the vacuum deposition method, the deposition apparatus is large and not easy to install, a vacuum must be maintained during the process, the process temperature is high, and in particular, because a mask is used for the pattern, the material consumption rate is high, so the productivity is low and the manufacturing cost is high Therefore, it is difficult to manufacture an organic electric device in a large area.

In order to solve this problem, research to form an organic thin film through a low-cost solution process has been continuously conducted. The solution process has the disadvantage of not having a high resolution compared to the vacuum deposition process, but since it can be manufactured at atmospheric pressure and atmospheric temperature, a separate vacuum device is not required. The advantage is that it can be expanded to a large area.

Such solution processes include spin coating, inkjet coating, screen printing, spray coating, roll-to-roll coating, and blade coating. Specific examples of a method for manufacturing a large-area organic thin film based on a solution process and an apparatus thereof are disclosed in Korean Patent Application Laid-Open No. 2016-0069799, Korean Patent Publication No. 10-1618395, Korean Patent Application Laid-Open No. 2017-0066703, It is detailed in Korean Patent Publication No. 10-1618395, Korean Patent Application Laid-Open No. 2016-0141127, and Korean Patent Publication No. 2016-0138845. In addition, thermal printing techniques and devices that can be used are described, for example, in US Patent Application Publications US 2008/0311307 A1, US 2008/0308037 A1, US2006/0115585 A1, US 2010/0188457 A1, US 2011/0008541 A1, US 2010/ 0171780 A1, and those described in US 2010/0201749 A1, which are incorporated herein by reference in their entirety.

However, when coating the multilayer organic film for an organic electric device using a solution process, there is a problem in that the organic thin film of the lower layer is damaged by the organic solvent contained in the organic compound of the upper layer, so it is difficult to form the multilayer thin film. In order to solve this problem, an organic compound having a cross-linking functional group must be used, and the known cross-linking groups are styrene, acrylate, oxetane, and the like. However, since these crosslinking groups require a high crosslinking temperature for the crosslinking reaction, it is difficult to use a plastic substrate. In addition, in the case of UV crosslinking, there is a disadvantage in that a photoinitiator is used or a byproduct is generated, which causes problems in the lifespan and efficiency of the organic electric device.

On the other hand, a benzocyclobutene (BCB: Benzocyclobutene) group is an example of a moiety that typically undergoes thermally activated dimerization at 200° C. or higher, in this case formed by cleavage of one of the CC bonds of cyclobutene, A dibenzocyclooctadiene ring is formed, followed by irreversible cyclization. It is documented in publications (Dobish, JN; Hamilton, SK; Harth, EPolymer Chemistry 2012, 3, 857-860) that substitution of an oxygen-based donor in these cyclobutene rings has a dramatic effect on the ring opening temperature of the BCB. It is recorded. However, this phenomenon has not yet been exploited in OLED applications.

Benzocyclobutene (BCB) chemistry and its use in OLEDs are described in the following publications: US20040004433, US20080315757, US20080309229, US20100133566, US20110095278, US20110065222, US201100198573, US20110042661, JP2010062120, US7893160, US201100189411, US2007007002120, US20110089411, US2007000089411, US200 , WO2012052704, WO2012175975, WO2013007966, international application PCT/CN14/084918 (filed on 8/21/14), US provisional application 62/039935 (filed on 8/21/14)

In particular, Korean Patent Publication No. 2017-0043557 (Patent Document 2) provides a composition comprising a crosslinkable BCB-functionalized material for use in OLED applications. The composition of Patent Document 2 may be used to form a hole-transporting material for use in an electroluminescent device. In particular, Patent Document 2 provides a composition comprising at least one compound selected from the following [Structure A]. That is, the composition including at least one compound selected from the following [Structure A] may be a composition containing carbazole substituted with benzocyclobutene.

[Structure A]

However, there remains a need for new and novel organic electrophoretic compounds for use in OLED applications comprising crosslinkable BCB-functionalized materials. These needs are met by the present invention.

JP 2006-156847 A KR 2017-0043557 A

“Organic Light-Emitting Diode (OLED) Technology: Materials Devices and Display Technologies”, Polym, Int., 55:572-582 (2006) Dobish, JN; Hamilton, SK; Harth, EPolymer Chemistry 2012, 3, 857-860

The technical task to be achieved by the present invention is to provide novel and novel compounds for organic electronic devices comprising crosslinkable BCB-functionalized materials suitable for use in OLED applications.

In addition, the present invention is to provide a novel compound for an organic electric device, which can be cross-linked at a low temperature of 120° C. or less, and has excellent efficiency and lifespan characteristics by not generating a byproduct, and a method for preparing the compound.

In particular, another object of the present invention is to provide an organic thin film for an organic electric device that is cross-linked through heating at a low temperature of about 120° C. and is not soluble in an organic solvent.

In addition, another object of the present invention is to provide an organic electric device including an OLED formed by stacking such an organic thin film in multiple layers, and an electronic device including the organic electric element.

The technical problems to be achieved by the present invention are not limited to the technical problems mentioned above, and other technical problems not mentioned can be clearly understood by those of ordinary skill in the art to which the present invention belongs from the description below. There will be.

A first aspect of the present invention for achieving the above technical problem is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device, The organic compound is, It is characterized in that it comprises at least one compound selected from

[Structure A]

In the [Formula A], x, y, z, w are natural numbers including 0, R ₁ , R ₂ , R ₃ , R ₄ are the same as or different from each other, and each independently hydrogen, an alkyl group (alkyl group) , substituted alkyl group, heterocyclo group (heterocyclic group), substituted heterocyclic group (heterocyclic group), aryl group (aryl group), substituted aryl group (aryl group), amine group (amine group), A pyridine group, a pyrimidine group, a triazole group, a triazine group, a phosphine group, a silole group, an arylamine group ), a carbazole group or a substituted carbazole group; wherein Ar ₁ is an aryl group or a substituted aryl group;

The R ₁ , R ₂ , R ₃ , and at least one selected from R ₄ is directly applied to a benzocyclobutene group of the following [Structural Formula B] or hydrogen, an alkyl group, a substituted alkyl group ), a heterocyclo group, a substituted heterocyclic group, an aryl group, a substituted aryl group, an amine group to the following [Structural Formula B] benzo Derivatives substituted with benzocyclobutene groups are applied;

[Structural Formula B]

In the [Formula B], X ₁ is a bond connecting the [Formula A] and [Formula B], such as -alkyl-, -O-, -alkylene-, etc., or hydrogen, hydrocarbon, halogen, cyano, nitro, alkoxy , hydroxy, and the like, and X ₂ can be independently selected from hydrogen, hydrocarbon, substituted hydrocarbon, halogen, cyano, nitro, alkoxy, hydroxyl, and the like.

Another second aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric device, characterized in that it has the following chemical formula.

(y is a natural number greater than or equal to 2)

Another third aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device, and has the following chemical formula.

(z is a natural number greater than or equal to 2)

Another fourth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric device, characterized in that it has the following chemical formula.

(x is a natural number greater than or equal to 2)

Another fifth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric device, characterized in that it has the following chemical formula.

(x and y are natural numbers greater than or equal to 2)

Another sixth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric device, characterized in that it has the following chemical formula.

(y ₁ , y ₂ are natural numbers greater than or equal to 2)

Another seventh aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric device, characterized in that it has the following chemical formula.

(y and z are natural numbers greater than or equal to 2)

Another eighth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric device, characterized in that it has the following chemical formula.

(x and z are natural numbers greater than or equal to 2)

Another ninth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device, and has the following chemical formula.

(x and y are natural numbers greater than or equal to 2)

Another tenth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of the organic electric device, characterized in that it has the following chemical formula.

(y and z are natural numbers greater than or equal to 2)

Another eleventh aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device, and has the following chemical formula.

(x, y, z are natural numbers greater than or equal to 2)

Another twelfth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device, and has the following chemical formula.

(x, y, z are natural numbers greater than or equal to 2)

Another thirteenth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device, and has the following chemical formula.

(x, z, w are natural numbers greater than or equal to 2)

Another fourteenth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device, and has the following chemical formula.

(y and w are natural numbers greater than or equal to 2)

Another fifteenth aspect of the present invention is an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device, and has the following chemical formula.

(x, y, w are natural numbers greater than or equal to 2)

The organic compound is at least one selected from the group consisting of a light emitting layer material, a hole injection layer material, a hole transport layer material, an electron injection layer material, an electron transport layer material, an electron blocking layer material, and a hole blocking layer material among organic thin film materials for an organic electric device It is characterized in that it is used for the purpose.

Another sixteenth aspect of the present invention is an ink composition for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device, wherein the ink composition is any one selected from the first to fifteenth aspects It is characterized in that it contains an organic compound of

The ink composition is characterized in that it is a solution or suspension further containing a solvent. In addition, the ink composition may further include a pigment or dye.

The ink composition may further include a phosphorescent dopant or a fluorescent dopant.

Another seventeenth aspect of the present invention is an organic electric device in which an organic thin film layer comprising at least a light emitting layer or a plurality of layers is sandwiched between a cathode and an anode, wherein the organic compound for forming the organic thin film layer comprises the first It is characterized in that it contains any one organic compound selected from the first aspect to the fifteenth aspect.

A crosslink is formed between benzocyclobutene groups at the ends of the organic compound forming the organic thin film layer.

The organic thin film layer is at least one selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer, and an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, It has a structure in which the electron injection layer and the cathode are stacked in this order.

In addition, the organic thin film layer is characterized in that it is prepared by coating the ink composition containing the organic compound by a solution process and drying it to form a film.

Another eighteenth aspect of the present invention relates to an electronic device including the organic electric device according to the seventeenth aspect.

According to an embodiment of the present invention, by providing a BCB-crosslinking substituent in a compound for an organic electric device, the solubility of a low molecular weight organic compound with low solubility can be improved, and as the solubility is improved, it is applied to a solution process with high productivity The first effect is that, when an organic compound has at least two BCB-crosslinking substituents, a stable organic thin film is formed by crosslinking of the BCB-crosslinking substituents at a relatively low temperature (150° C. or less). The second effect that a multi-layered organic film layer can be formed through a solution process, but the third effect that a stable multi-layered device can be manufactured without the phenomenon that adjacent layers are dissolved by the solution, the large area of the organic device and low cost It has the fourth effect that painting is possible.

The organic compound according to the present invention may have improved solubility in various solvents by having a BCB substituent capable of crosslinking. In addition, in the prior art, low molecular weight organic compounds have poor solubility, so organic thin films are mainly formed through a deposition process. The organic compounds according to the present invention can provide properties suitable for various solution processes by improving solubility.

In addition, in the prior art, even if an organic thin film is formed through a solution process, there is a problem in that it must be performed under high temperature conditions in order to form a stable organic thin film. However, the organic compound according to the present invention not only has excellent solubility in solvents, but also can form a heat-stable thin film even at a low temperature process due to crosslinking of the BCB substitution period provided in the compound. and cost reduction.

It should be understood that the effects of the present invention are not limited to the above-described effects, and include all effects that can be inferred from the configuration of the invention described in the detailed description or claims of the present invention.

Hereinafter, embodiments of the present invention will be described in detail. However, the present invention may be embodied in several different forms, and thus is not limited to the embodiments described herein.

Throughout the specification, when a part is said to be “connected (connected, contacted, coupled)” with another part, it is not only “directly connected” but also “indirectly connected” with another member interposed therebetween. "Including cases where In addition, when a part "includes" a certain component, this means that other components may be further provided, rather than excluding other components, unless otherwise stated.

The terminology used herein is used only to describe specific embodiments, and is not intended to limit the present invention. The singular expression includes the plural expression unless the context clearly dictates otherwise. In the present specification, terms such as “comprise” or “have” are intended to designate that a feature, number, step, operation, component, part, or combination thereof described in the specification exists, but one or more other features It should be understood that this does not preclude the existence or addition of numbers, steps, operations, components, parts, or combinations thereof.

The terminology used in the specification is used only to describe a specific embodiment (aspect, aspect, aspect) (or embodiment), and is not intended to limit the present invention. The singular expression includes the plural expression unless the context clearly dictates otherwise. In the present application, terms such as comprises or consists of are intended to designate that the features, numbers, steps, operations, components, parts, or combinations thereof described in the specification exist, but one or more other features It is to be understood that it does not preclude the possibility of the presence or addition of numbers, steps, operations, components, parts, or combinations thereof. Unless defined otherwise, all terms used herein, including technical and scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Terms such as those defined in commonly used dictionaries should be interpreted as having a meaning consistent with the meaning in the context of the related art, and should not be interpreted in an ideal or excessively formal meaning unless explicitly defined in the present application. does not

Hereinafter, embodiments of the present invention will be described in detail with reference to structured chemical formulas and the like.

Crosslinkable BCB-functionalized materials have also been found in conventional OLED applications. In the present invention, by substituting various functional groups (for example, oxygen donor, hydroxyl group, amino group, etc.) on the ring of the benzocyclobutene compound, the temperature of ring opening is 150 ° C. or less, in particular, 120 ° C. or less. It was found that it can be lowered to a low temperature, thereby sufficiently satisfying the solution-processing conditions in OLED applications. In particular, substitution of the oxygen donor can significantly reduce the ring-opening temperature of the benzocyclobutene compound to 100-120° C., which can have significant process advantages.

Specifically, the present invention relates to an organic compound comprising at least two or more benzocyclobutene crosslinking derivatives at the end of a core material forming an organic thin film for OLED application. In particular, the organic compound according to the present invention provides a composition comprising at least one compound selected from the following [Structural Formula 1].

[Structural Formula 1]

In the [Formula 1], x, y, z, w are natural numbers including 0, R ₁ , R ₂ , R ₃ , R ₄ are the same as or different from each other, and each independently hydrogen, an alkyl group (alkyl group) , substituted alkyl group, heterocyclo group (heterocyclic group), substituted heterocyclic group (heterocyclic group), aryl group (aryl group), substituted aryl group (aryl group), amine group (amine group), A pyridine group, a pyrimidine group, a triazole group, a triazine group, a phosphine group, a silole group, an arylamine group ), a carbazole group or a substituted carbazole group; wherein Ar ₁ is an aryl group or a substituted aryl group;

The R ₁ , R ₂ , R ₃ , and at least one selected from R ₄ is directly applied to a benzocyclobutene group of the following [Structural Formula 2] or hydrogen, an alkyl group, a substituted alkyl group ), a heterocyclo group, a substituted heterocyclic group, an aryl group, a substituted aryl group, an amine group to the following [Structural Formula 2] Derivatives substituted with benzocyclobutene groups are applied;

[Structural Formula 2]

In the [Formula 2], X ₁ is a bond connecting [Formula 1] and [Formula 2], such as -alkyl-, -O-, -alkylene-, etc., or hydrogen, hydrocarbon, halogen, cyano, nitro, alkoxy, hydroxy and the like, and X ₂ can be independently selected from hydrogen, hydrocarbon, substituted hydrocarbon, halogen, cyano, nitro, alkoxy, hydroxyl, and the like.

Examples of the heterocyclic group applicable in the present invention include tetrahydrofuran, thiophene, pyridine, pyrimidine, benzothiophene, benzofuran ( benzofuran), dibenzofuran (dibenzofuran), and the like.

In addition, examples of the aryl group applicable in the present invention include phenyl, naphthyl, phenanthryl, pyrenyl, fluorenyl, carbazoyl ( cabazolyl), spirobifluorene, tetraphenylsilane, tetraphenylmethane, and the like.

In addition, examples of the amine group applicable in the present invention include diphenylamine, triphenylamine, and the like.

The organic compound represented by the [Structural Formula 1] according to the present invention is a light emitting layer (EML) material and a hole injection layer (HIL) material for forming various organic thin films disposed between the first electrode and the second electrode of the organic electric device. , a hole transport layer (HTL) material, an electron injection layer (EIL) material, an electron transport layer (ETL) material, an electron blocking layer (EBL) material, a hole blocking layer (HBL) material, and the like.

When the organic compound according to the present invention is heated at a low temperature of about 120° C., cross-linking occurs through a thermal isomerization reaction between the benzocyclobutene groups of [Structural Formula 2].

For this reason, since the organic thin film made of the organic compound according to the present invention does not dissolve in the organic solvent of the adjacent organic thin film layer, the thin film is not damaged even when multi-layered thin films are stacked through a solution process. optimized for making

In one embodiment of the present invention, specific examples of the organic compound of the present invention represented by the [Structural Formula 1] may be selected from the following [Formula 1] to [Formula 14].

Here, y is a natural number of 2 or more.

Here, z is a natural number greater than or equal to 2.

Here, x is a natural number greater than or equal to 2.

Here, x and y are natural numbers greater than or equal to 2.

Here, y ₁ and y ₂ are natural numbers greater than or equal to 2.

Here, y and z are natural numbers of 2 or more.

Here, x and z are natural numbers greater than or equal to 2.

Here, x and y are natural numbers greater than or equal to 2.

Here, y and z are natural numbers of 2 or more.

Here, x, y, and z are natural numbers greater than or equal to 2.

Here, x, y, and z are natural numbers greater than or equal to 2.

Here, x, z, and w are natural numbers of 2 or more.

Here, y and w are natural numbers of 2 or more.

Here, x, y, and w are natural numbers of 2 or more.

In another embodiment of the present invention, there is provided an ink composition comprising the organic compound according to the [Structural Formula 1] according to the present invention, in particular, the organic compound of the [Formula 1] to [Formula 14].

The ink composition may be a solution or suspension containing a solvent, and the solvent is, for example, anisole, dimethyl anisole, xylene, o-xylene, m-xylene, p-xylene, toluene, mesitylene, methyl. Benzoate, dioxane, tetrahydrofuran, methyl tetrahydrofuran, tetrahydropyran, tetralin, veratrol, chlorobenzene, N-methyl pyrrolidone, N,N-dimethylformamide, dimethylsulfoxide and combinations thereof It may include one selected from the group consisting of.

An organic thin film layer may be formed by coating the ink composition and then forming a film by removing the solvent. The ink composition may further include a pigment or dye. The ink composition may further include a phosphorescent dopant or a fluorescent dopant.

In another embodiment of the present invention, in the organic electric device in which an organic thin film layer comprising at least a light emitting layer or a plurality of layers is stacked between the cathode and the anode in a multi-layered manner, at least one of the organic thin film layers is the [Structural formula 1] according to the organic compound, in particular, [Formula 1] to [Formula 14] provides an organic electric device characterized in that it contains the organic compound. In particular, the organic electric device is preferably an organic electroluminescent device (OLED).

The organic thin film layer may be prepared by forming a film through a solution process using the above-described ink composition including the organic compound according to the present invention. This solution process includes any one method selected from the group consisting of spin coating, gravure offset printing, reverse offset printing, screen printing, roll-to-roll printing, slot die coating, dip coating, spray coating, doctor blade coating, and inkjet coating. do.

The organic thin film layer is a layer in which the organic compound includes at least one selected from the group consisting of a light emitting layer material, a hole injection layer material, a hole transport layer material, an electron injection layer material, an electron transport layer material, an electron blocking layer material, and a hole blocking layer material. may include The light emitting layer material may be a phosphorescent or fluorescent host and a phosphorescent dopant or fluorescent dopant material.

In particular, the organic light emitting diode (OLED) may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are stacked in this order. The light emitting layer may include a phosphorescent dopant or a fluorescent dopant including red, green, blue, or white together with the organic compound according to the present invention. For example, the phosphorescent dopant may be an organometallic compound including at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm.

The hole transport layer, the hole injection layer, the hole blocking layer, the electron injection transport layer, the electron transport layer, the electron injection layer and the electron blocking layer may include the organic compound according to the present invention described above.

Hereinafter, an organic electroluminescent device as an organic electric device according to the present invention will be described as an example. The organic electroluminescent device of the present invention may have a structure in which an anode (hole injection electrode), a hole injection layer (HIL) and/or a hole transport layer (HTL), a light emitting layer (EML) and a cathode (electron injection electrode) are sequentially stacked. and, preferably, an electron blocking layer (EBL) between the anode and the light emitting layer, and an electron transport layer (ETL), an electron injection layer (EIL) or a hole blocking layer (HBL) between the cathode and the light emitting layer. there is.

In the method for manufacturing an organic light emitting diode according to the present invention, an anode is formed by first coating a material for an anode on the surface of a substrate in a conventional manner. In this case, the substrate used is preferably a glass substrate or a transparent plastic substrate excellent in transparency, surface smoothness, handling and waterproofing properties. In addition, as the material for the anode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc. which are transparent and have excellent conductivity may be used.

Next, a hole injection layer (HIL) material is spin coated on the surface of the anode to form a hole injection layer, and a hole transport layer (HTL) material is spin coated on the surface of the hole injection layer to form a hole transport layer, and the hole transport layer An emission layer is formed by spin-coating an EML material on the surface, and an electron transport layer (ETL) material is spin-coated on the surface of the emission layer to form an electron transport layer.

At this time, optionally, by additionally forming a hole blocking layer (HBL) between the light emitting layer and the electron transport layer and using a phosphorescent dopant together in the light emitting layer, it is possible to prevent the phenomenon of triplet excitons or holes from being diffused into the electron transport layer. The hole blocking layer may be formed by spin coating the hole blocking layer material, and in the case of the hole blocking layer material, the organic compound of the present invention may be used.

An electron injection layer is formed by spin coating an electron injection layer (EIL) material on the surface of the electron transport layer. Finally, a cathode is formed by vacuum thermal evaporation of a material for a cathode on the surface of the electron injection layer in a conventional manner. At this time, as the material for the anode used, lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and the like can be used. In addition, in the case of a top light emitting organic light emitting device, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode through which light can pass.

The organic electroluminescent device according to the present invention may be manufactured in the same order as described above, that is, anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode, and vice versa Electron injection layer / electron transport layer / hole blocking layer / light emitting layer / hole transport layer / hole injection layer / anode may be prepared in the order.

In another embodiment of the present invention, an electronic device (or electronic device) including the organic electroluminescent device is provided.

Hereinafter, a method for synthesizing organic compounds according to the present invention will be described below through representative examples. However, the method for synthesizing the organic compounds of the present invention is not limited to the methods exemplified below, and the organic compounds of the present invention may be prepared by the methods illustrated below and methods known in the art.

<Synthesis of intermediates >

Intermediates for preparing the organic compound according to the present invention were synthesized through the following process.

(1) intermediate (a)

Referring to the above reaction scheme, cesium fluoride (11.4 g, 75.0 mmol) was placed in a round flask and dried. After putting 100mL of acetonitrile in a round flask, butyl vinyl ether (4.9mL, 38mmol) and 4-bromo-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (5.70g, 15.7mmol) are slowly added dropwise. After reacting at room temperature for 24 hours, water and DCM were added, and the organic layer was separated. Purification by column chromatography (PE:DCM = 1:8) gives the following intermediate (a).

Intermediate (a)

(2) intermediate (b)

Referring to the reaction scheme, the intermediate (a) (1.3 g, 5 mmol), P(t-Bu) 3 (0.04 g, 0.22 mmol), Pd ₂ (dba) ₃ (0.11 g, 0.12 mmol), bis (4) -bromophenyl)amine (1.6g, 5mmol), and tert-butoxide (1.0g, 10.6mmol) are dissolved in toluene (30mL). The reaction was carried out at 100°C for 20 hours. After completion of the reaction, it is cooled at room temperature. The cooled mixture was extracted with dichloromethane and dried over MgSO ₄ . Purification by column chromatography (ethyl acetate:hexane=1:4) gives the following intermediate (b).

Intermediate (b)

(3) intermediate (c)

Referring to the reaction scheme, the intermediate (b) (1g, 2mmol), Bis(pinacolato)diboron (1g, 4mmol)), Pd(dppf)Cl ₂ (0.7g, 0.06mmol) and Potassium acetate (0.78g) in a flask , 8 mmol), dissolved in 50 mL of DMF, and then, nitrogen was sufficiently flowed. Thereafter, it is refluxed at 90°C. After completion of the reaction, extraction is performed with water and MC. After removing residual moisture with MgSO ₄ , it is purified by column chromatography using methylene chloride:hexane to obtain the following intermediate (c).

Intermediate (c)

(4) intermediate (d)

Referring to the above reaction scheme, cesium fluoride (11.4 g, 75.0 mmol) was placed in a round flask and dried. After putting 100mL of acetonitrile in a round flask, (2-bromoethoxy)ethene (4.1mL, 38mmol) and 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (4.8g, 15.7mmol) are slowly added dropwise. After reacting at room temperature for 24 hours, water and DCM were added, and the organic layer was separated. Purification by column chromatography (PE:DCM = 1:8) gives the following intermediate (d) (yield: 70%).

intermediate (d)

(5) intermediate (e)

Referring to the above reaction scheme, sodium hydride (0.6 g) is placed in a flask, and a solution obtained by dissolving 3,6-dibromocarbazole (3.8 g, 12 mmol) in DMF (50 mL) is slowly added dropwise. After adding the intermediate (d) (4.3 g, 18 mmol) to the mixed solution, the mixture was reacted at room temperature for 6 hours. After completion of the reaction, water is added to complete the reaction. Then, ethyl acetate is added and extracted. After removing the solvent, it is purified by column chromatography (ethyl acetate:hexane = 1:6) to obtain the following intermediate (e).

Intermediate (e)

(6) intermediate (f)

Referring to the reaction scheme, the intermediate (e) (1g, 2mmol), Bis(pinacolato)diboron (1g, 4mmol)), Pd(dppf)Cl ₂ (0.7g, 0.06mmol) and Potassium acetate (0.78g) in a flask , 8 mmol), dissolved in 50 mL of DMF, and then, nitrogen was sufficiently flowed. Thereafter, it is refluxed at 90°C. After completion of the reaction, extraction is performed with water and MC. After removing the residual moisture with MgSO ₄ , it is purified by column chromatography using methylene chloride:hexane to obtain the following intermediate (f).

Intermediate (f)

(7) intermediate (g)

Referring to the above reaction scheme, 2,7-dibromofluorene (3.0 g, 9.26 mmol), tetrabutyl ammonium bromide (0.3 g, 0.9 mmol), 50% aqueous NaOH (15.0 mL), and toluene (20 mL) were placed in a flask. After the mixture is thoroughly mixed, the above intermediate (d) (4.2 g, 23 mmol) is added. The reaction is stirred at 60° C. for 8 hours. After completion of the reaction, extraction was performed with water and ethyl acetate. After removing the residual moisture with MgSO ₄ , it is purified by chromatography using ethyl acetate:hexane to obtain the following intermediate (g).

Intermediate (g)

(8) intermediate (h)

Referring to the reaction scheme, the intermediate (g) (1g, 2mmol), Bis(pinacolato)diboron (1g, 4mmol)), Pd(dppf)Cl ₂ (0.7g, 0.06mmol) and Potassium acetate (0.78g) in a flask , 8 mmol) and dissolved in 50 mL of DMF, and then nitrogen is sufficiently flowed. Thereafter, it is refluxed at 90°C. After completion of the reaction, extraction is performed with water and MC. After removing residual moisture with MgSO ₄ , it is purified by column chromatography using methylene chloride:hexane to obtain the following intermediate (h).

intermediate (h)

(9) intermediate (i)

Referring to the above reaction scheme, sodium hydride (0.6 g) is placed in a flask, and a solution obtained by dissolving bis(4-bromophenyl)amine (3.9 g, 12 mmol) in DMF (50 mL) is slowly added dropwise. 7-(4-bromophenethoxy)bicyclo[4.2.0]octa-1,3,5-triene (4.5g, 15mmol) was added to the mixed solution, and then reacted at room temperature for 6 hours. After completion of the reaction, water is added to complete the reaction. Then, ethyl acetate is added and extracted. After removing the solvent, it is purified by column chromatography (ethyl acetate:hexane = 1:6) to obtain the following intermediate (i).

Intermediate (i)

<Example 1>

The organic compound of [Formula 1] was synthesized through the following reaction scheme.

Put the intermediate (b) (0.5 g, 1.0 mmol) and the intermediate (c) (0.59 g, 1.0 mmol) in a 50 mL flask. Add tetrakis(triphenylphosphine)palladium to the mixed solution and add toluene. The reaction solution is refluxed for 72 hours. After completion of the reaction, it was put into methanol and precipitated. After filtering the product, it is washed with methanol to obtain an organic compound of the following [Formula 1].

[Formula 1]

Here, y is a natural number greater than or equal to 2.

<Example 2>

The organic compound of [Formula 2] was synthesized through the following reaction scheme.

Intermediate (e) (0.5 g, 1.0 mmol) and intermediate (f) (0.59 g, 1.0 mmol) were placed in a 50 mL flask. Add tetrakis(triphenylphosphine)palladium to the mixed solution and add toluene. The reaction solution is refluxed for 72 hours. After completion of the reaction, it was put into methanol and precipitated. After filtering the product, it is washed with methanol to obtain an organic compound of the following [Formula 2].

[Formula 2]

Here, z is a natural number greater than or equal to 2.

<Example 3>

The organic compound of [Formula 3] was synthesized through the following reaction scheme.

The intermediate (g) (0.5 g, 1.0 mmol) and the intermediate (h) (0.59 g, 1.0 mmol) were placed in a 50 mL flask. Add tetrakis(triphenylphosphine)palladium to the mixed solution and add toluene. The reaction solution is refluxed for 72 hours. After completion of the reaction, it was put into methanol and precipitated. After filtering the product, it is washed with methanol to obtain an organic compound of the following [Formula 3].

[Formula 3]

Here, x is a natural number greater than or equal to 2.

<Example 4>

The organic compound of [Formula 4] was synthesized through the following reaction scheme.

Intermediate (i) (0.3 g, 0.6 mmol), 2,2'-(9,9-dihexyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1) in a 50 mL flask ,3,2-dioxaborolane) (0.3g, 0.63mmol) is added. Add tetrakis(triphenylphosphine)palladium to the mixed solution and add toluene. The reaction solution is refluxed for 72 hours. After completion of the reaction, it was put into methanol and precipitated. After filtering the product, it is washed with methanol and dried to obtain an organic compound of the following [Formula 4].

[Formula 4]

Here, x and y are natural numbers greater than or equal to 2.

<Example 5>

The organic compound of [Formula 5] was synthesized through the following reaction scheme.

Intermediate (b) (0.3 g, 0.6 mmol), 4-butyl-N,N-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) in a 50 mL flask Add phenyl)aniline (0.3g, 0.63mmol). Add tetrakis(triphenylphosphine)palladium to the mixed solution and add toluene. The reaction solution is refluxed for 72 hours. After completion of the reaction, it was put into methanol and precipitated. After filtering the product, it is washed with methanol and dried to obtain an organic compound of the following [Formula 5].

[Formula 5]

Here, y ₁ and y ₂ are natural numbers greater than or equal to 2.

<Example 6>

The organic compound of [Formula 6] was synthesized through the following reaction scheme.

Intermediate (i) (0.3 g, 0.6 mmol), 9-butyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H- in a 50 mL flask Add carbazole (0.3 g, 0.63 mmol). Add tetrakis(triphenylphosphine)palladium to the mixed solution and add toluene. The reaction solution is refluxed for 72 hours. After completion of the reaction, it was put into methanol and precipitated. After filtering the product, it is washed with methanol and dried to obtain an organic compound of the following [Formula 6].

[Formula 6]

Here, y and z are natural numbers greater than or equal to 2.

<Example 7>

The organic compound of [Formula 7] was synthesized through the following reaction scheme.

Intermediate (e) (0.3 g, 0.6 mmol), 2,2'-(9,9-dihexyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1) in a 50 mL flask ,3,2-dioxaborolane) (0.3g, 0.63mmol) is added. Add tetrakis(triphenylphosphine)palladium to the mixed solution and add toluene. The reaction solution is refluxed for 72 hours. After completion of the reaction, it was put into methanol and precipitated. After filtering the product, it is washed with methanol and dried to obtain an organic compound of the following [Formula 7].

[Formula 7]

Here, x and z are natural numbers greater than or equal to 2.

<Example 8>

The organic compound of [Formula 8] was synthesized through the following reaction scheme.

Intermediate (g) (0.37 g, 0.6 mmol), 4-butyl-N,N-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) in a 50 mL flask Add phenyl)aniline (0.3g, 0.63mmol). Add tetrakis(triphenylphosphine)palladium to the mixed solution and add toluene. The reaction solution is refluxed for 72 hours. After completion of the reaction, it was put into methanol and precipitated. After filtering the product, it is washed with methanol and dried to obtain an organic compound of the following [Formula 8].

[Formula 8]

Here, x and y are natural numbers greater than or equal to 2.

<Example 9>

The organic compound of [Formula 9] was synthesized through the following reaction scheme.

Intermediate (e) (0.5 g, 1.0 mmol) and intermediate (c) (0.59 g, 1.0 mmol) were placed in a 50 mL flask. Add tetrakis(triphenylphosphine)palladium to the mixed solution and add toluene. The reaction solution is refluxed for 72 hours. After completion of the reaction, it was put into methanol and precipitated. After filtering the product, it is washed with methanol to obtain an organic compound of the following [Formula 9].

[Formula 9]

Here, y and z are natural numbers greater than or equal to 2.

<Example 10>

The organic compound of [Formula 10] was synthesized through the following reaction scheme.

Intermediate (e)(0.25g, 0.6mmol), Intermediate (c)(0.3g, 0.6mmol), 2,2'-(9,9-dihexyl-9H-fluorene-2,7-diyl)bis in a 50 mL flask (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (0.70 g, 1.2 mmol) is added. Add tetrakis(triphenylphosphine)palladium to the mixed solution and add toluene. The reaction solution is refluxed for 72 hours. After completion of the reaction, it was put into methanol and precipitated. After filtering the product, it is washed with methanol and dried to obtain an organic compound of the following [Formula 10].

[Formula 10]

Here, x, y, and z are natural numbers greater than or equal to 2.

<Example 11>

The organic compound of [Formula 11] was synthesized through the following reaction scheme.

Intermediate (b) (0.25 g, 0.6 mmol), intermediate (g) (0.37 g, 0.6 mmol), 9-(nonan-3-yl)-3,6-bis(4,4,5,5) in a 50 mL flask -tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (0.65 g, 1.2 mmol) is added. Add tetrakis(triphenylphosphine)palladium to the mixed solution and add toluene. The reaction solution is refluxed for 72 hours. After completion of the reaction, it was put into methanol and precipitated. After filtering the product, it is washed with methanol and dried to obtain an organic compound of the following [Formula 11].

[Formula 11]

Here, x, y, and z are natural numbers greater than or equal to 2.

<Example 12>

The organic compound of [Formula 12] was synthesized through the following reaction scheme.

2,7-dibromo-9,9-dihexyl-9H-fluorene (0.2 g, 0.4 mmol), intermediate (c) (0.2 g, 0.4 mmol), 3-(2,5-dimethyl-4-( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,5-dimethyl-2,4-dioxa-3-borabicyclo[3.1.0]hexane (0.13 g, 0.42 mmol) is added. Add tetrakis(triphenylphosphine)palladium to the mixed solution and add toluene. The reaction solution is refluxed for 72 hours. After completion of the reaction, it was put into methanol and precipitated. After filtering the product, it is washed with methanol and dried to obtain an organic compound of the following [Formula 12] (yield: 54%).

[Formula 12]

Here, x, z, and w are natural numbers greater than or equal to 2.

<Example 13>

The organic compound of [Formula 13] was synthesized through the following reaction scheme.

Intermediate (i) (0.3 g, 0.6 mmol), 9,10-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) anthracene (0.3 g, 0.63 mmol) in a 50 mL flask ) is put in Add tetrakis(triphenylphosphine)palladium to the mixed solution and add toluene. The reaction solution is refluxed for 72 hours. After completion of the reaction, it was put into methanol and precipitated. After filtering the product, it is washed with methanol and dried to obtain an organic compound of the following [Formula 13].

[Formula 13]

Here, y and w are natural numbers greater than or equal to 2.

<Example 14>

The organic compound of [Formula 14] was synthesized through the following reaction scheme.

Intermediate (c) (0.25 g, 0.6 mmol), 2,4-dibromo-6-phenyl-1,3,5-triazine (0.19 g, 0.6 mmol), 2,2'-(9,9-) in a 50 mL flask Add dihexyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (0.3 g, 0.63 mmol). Add tetrakis(triphenylphosphine)palladium to the mixed solution and add toluene. The reaction solution is refluxed for 72 hours. After completion of the reaction, it was put into methanol and precipitated. After filtering the product, it is washed with methanol and filtered to obtain an organic compound of the following [Formula 14].

[Formula 14]

Here, x, y, and w are natural numbers greater than or equal to 2.

Claims (26)

As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device,
The organic compound is an organic compound, characterized in that it comprises at least one compound selected from the following [Structural Formula A].
[Structure A]

In the [Formula A], x, y, z, w are natural numbers including 0, R ₁ , R ₂ , R ₃ , R ₄ are the same as or different from each other, and each independently hydrogen, an alkyl group (alkyl group) , substituted alkyl group, heterocyclo group (heterocyclic group), substituted heterocyclic group (heterocyclic group), aryl group (aryl group), substituted aryl group (aryl group), amine group (amine group), A pyridine group, a pyrimidine group, a triazole group, a triazine group, a phosphine group, a silole group, an arylamine group ), a carbazole group or a substituted carbazole group; wherein Ar ₁ is an aryl group or a substituted aryl group;
The R ₁ , R ₂ , R ₃ , R ₄ At least one selected from among the benzocyclobutene group (benzocyclobutene) of the following [Structural Formula B] is directly applied or hydrogen, an alkyl group (alkyl group), a substituted alkyl group (alkyl group) ), a heterocyclo group, a substituted heterocyclic group, an aryl group, a substituted aryl group, an amine group to the following [Structural Formula B] benzo Derivatives substituted with benzocyclobutene groups are applied;
[Structural Formula B]

In the [Formula B], X ₁ is a bond connecting the [Formula A] and [Formula B], such as -alkyl-, -O-, -alkylene-, etc., or hydrogen, hydrocarbon, halogen, cyano, nitro, alkoxy , hydroxy, and the like, and X ₂ may be independently selected from hydrogen, hydrocarbon, substituted hydrocarbon, halogen, cyano, nitro, alkoxy, hydroxyl, and the like. As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device,
The organic compound is an organic compound, characterized in that it has the following chemical formula.

(y is a natural number greater than or equal to 2) As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device,
The organic compound is an organic compound, characterized in that it has the following chemical formula.

(z is a natural number greater than or equal to 2) As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device,
The organic compound is an organic compound, characterized in that it has the following chemical formula.

(x is a natural number greater than or equal to 2) As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device,
The organic compound is an organic compound, characterized in that it has the following chemical formula.

(x and y are natural numbers greater than or equal to 2) As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device,
The organic compound is an organic compound, characterized in that it has the following chemical formula.

(y ₁ , y ₂ are natural numbers greater than or equal to 2) As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device,
The organic compound is an organic compound, characterized in that it has the following chemical formula.

(y and z are natural numbers greater than or equal to 2) As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device,
The organic compound is an organic compound, characterized in that it has the following chemical formula.

(x and z are natural numbers greater than or equal to 2) As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device,
The organic compound is an organic compound, characterized in that it has the following chemical formula.

(x and y are natural numbers greater than or equal to 2) As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device,
The organic compound is an organic compound, characterized in that it has the following chemical formula.

(y and z are natural numbers greater than or equal to 2) As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device,
The organic compound is an organic compound, characterized in that it has the following chemical formula.

(x, y, z are natural numbers greater than or equal to 2) As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device,
The organic compound is an organic compound, characterized in that it has the following chemical formula.

(x, y, z are natural numbers greater than or equal to 2) As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device,
The organic compound is an organic compound, characterized in that it has the following chemical formula.

(x, z, w are natural numbers greater than or equal to 2) As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device,
The organic compound is an organic compound, characterized in that it has the following chemical formula.

(y and w are natural numbers greater than or equal to 2) As an organic compound for forming an organic thin film disposed between the first electrode and the second electrode of an organic electric device,
The organic compound is an organic compound, characterized in that it has the following chemical formula.

(x, y, w are natural numbers greater than or equal to 2) 16. The method according to any one of claims 1 to 15,
The organic compound is at least one selected from the group consisting of a light emitting layer material, a hole injection layer material, a hole transport layer material, an electron injection layer material, an electron transport layer material, an electron blocking layer material, and a hole blocking layer material among organic thin film materials for an organic electric device Organic compounds, characterized in that used for the purpose. An ink composition for forming an organic thin film disposed between a first electrode and a second electrode of an organic electric device, the ink composition comprising:
The ink composition comprises an organic compound of any one of claims 1 to 15, characterized in that the ink composition. 18. The method of claim 17,
The ink composition is an ink composition, characterized in that the solution or suspension further comprising a solvent. 19. The method of claim 18,
The ink composition is an ink composition, characterized in that it further comprises a pigment or dye. 19. The method of claim 18,
The ink composition further comprises a phosphorescent dopant or a fluorescent dopant. In an organic electric device in which an organic thin film layer comprising at least a light emitting layer or a plurality of layers is sandwiched between a cathode and an anode,
An organic electric device, characterized in that the organic compound for forming the organic thin film layer comprises any one of the organic compound selected from claim 1 to claim 15. 22. The method of claim 21,
An organic electric device, characterized in that a crosslink is formed between benzocyclobutene groups at the ends of the organic compound forming the organic thin film layer. 23. The method of claim 22,
The organic thin film layer is an organic electric device, characterized in that at least one selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer. 24. The method of claim 23,
An organic electric device, characterized in that it has a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode are stacked in this order. 25. The method of claim 24,
The organic thin film layer is an organic electric device, characterized in that it is manufactured by coating the ink composition containing the organic compound by a solution process and drying it to form a film. An electronic device comprising the organic electric device according to claim 21.