KR20190016304A - Phase-changed material used in producing oled - Google Patents

Abstract

The present invention provides a phase change material used for an apparatus and a method to manufacture an organic electroluminescent device (OLED) by using phase change without using deposition or dissolution. According to the present invention, the method to manufacture the OLED using by using phase change comprises a step of phase-changing a solid state phase change material into a liquid state and a step of spraying the liquid state phase change material together with guide gas.

Description

[0001] PHASE-CHANGED MATERIAL USED IN PRODUCING OLED [0002]

The present invention relates to a phase change material that can be used in the production of an organic electroluminescent device.

BACKGROUND ART Conventionally, an organic electroluminescent device (OLED) is mainly manufactured by a vacuum deposition method. This is a method of manufacturing an organic electroluminescent device using a low molecular organic material in the form of a single compound, and it is advantageous in terms of lifetime and luminescent efficiency of the device, but an organic material in powder form must be vacuum deposited, And there is a loss of organic materials, so it is necessary to improve the cost.

Accordingly, a soluble ink jet printing method in which a polymer organic material is dissolved in a solvent and is formed is introduced. Such a solubility ink jet printing method is advantageous in that there is little discarded polymer organic material because the liquid state light emitting material is finely injected through each nozzle. In addition, due to the liquid phase process, it is not necessary to cut the raw glass substrate in a large production line of, for example, eight generations or more, so that the process can be simplified and the investment cost of the equipment can be minimized and the overall process time can be shortened .

However, polymeric co-polymer materials that are predominantly used in Soluble ink jet systems are likely to have a non-uniformly printed layer or a non-polymerized portion within that layer, The performance of the device may be deteriorated or the uniformity of the interface may be deteriorated. In addition, the Solubility ink jet printing method has limitations in using low molecular / monomolecular organic materials.

On the other hand, since Soluble ink jet system is a process of forming an organic material after dissolving it in a solvent, a solvent cost and a purification cost are required for a soluble material, and there is still a need for cost reduction. In addition, since the solubilization process includes the drying time of the solvent, there is a limit in shortening the production time. In addition, when the organic solvent is removed by evaporation, the space between the molecules may not be uniform, so that aggregation may occur. As a result, the performance of the device may be deteriorated, and a large amount of the organic material may be lost during the removal of the organic solvent . Furthermore, when the organic solvent can not be completely removed, the residual solvent may act as a trap, and the impurities contained in the solvent may deteriorate the light emitting property of the device.

Thus, the Solubility ink jet printing method has limitations in using low molecular / monomolecular organic materials, and the uniformity is lower than that of the vacuum evaporation method due to the use of the solvent, and additional devices for evaporating or sublimating the solvent As time is required, there remains a need for time and cost savings in the manufacturing process.

Korean Patent Publication No. 786993 (Dec. 12, 2007) Korean Patent Publication No. 546921 (2006. 1. 26. Announcement) Korean Patent Publication No. 1020240 (published on Mar. 08, 2011) Korean Patent Laid-Open Publication No. 2013-105409 (disclosed on September 25, 2013)

The present invention provides a phase change material that can be used in an apparatus and method for fabricating an organic electroluminescent device using phase change of a material without depending on vapor deposition or dissolution.

As a result of intensive studies in order to solve the above technical problems, the present inventors have found that in an ink jet apparatus or method for manufacturing an organic electroluminescent device using a phase change of a material, the phase change from solid state to liquid state, The present inventors have found that a phase-change material containing a light-emitting compound can achieve the above-mentioned object, thereby completing the present invention.

The phase change material according to the present invention has at least one of the following effects:

The phase change material according to the present invention may be suitable for an ink jet apparatus or method for manufacturing an organic electroluminescent device using a phase change of a material without using a solvent.

Since the phase change material according to the present invention may not include an organic solvent generally used in the Solubility ink jet method, it is possible to reduce the solvent cost and the purification cost of the solvent in the production of the organic electroluminescent device.

Since the evaporation time for removing the solvent is not required in the production of the organic electroluminescent device, the manufacturing process time can be shortened.

The phase change material according to the present invention may be phase-changed during manufacture of the organic electroluminescent device and appropriately sprayed together with the induction gas and / or the carrier gas, so that it can be applied closer to the desired shape.

The phase change material according to the present invention enables the organic electroluminescent device to be manufactured through an ink jet apparatus or a method even by using an existing deposition low molecular weight / monomolecular material.

Since the phase change material according to the present invention can be melted at a relatively low temperature, damage of the organic electroluminescent compound included in the phase change material can be prevented.

Since the phase change material according to the present disclosure can be melted at relatively low temperatures, the energy efficiency can be increased by reducing the use of heating energy.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 schematically shows an ink jet apparatus for manufacturing an organic electroluminescent device by phase-changing a solid phase-change material according to an embodiment of the present invention into a liquid state. FIG.
FIG. 2 illustrates a method of manufacturing an organic electroluminescent device by phase-changing a solid phase-change material according to an embodiment of the present invention into a liquid state.
FIG. 3 shows the structure of an ink jet device for manufacturing an organic electroluminescent device by phase-changing a solid phase-change material according to an embodiment of the present invention into a liquid state.
FIG. 4 illustrates a configuration of an ink jet device for fabricating an organic electroluminescent device by phase-changing a solid phase-change material according to an embodiment of the present invention into a liquid state.
FIG. 5 shows a configuration of an ink jet apparatus for manufacturing an organic electroluminescent device by phase-changing a solid phase-change material according to an embodiment of the present invention into a liquid state.
FIG. 6 schematically illustrates the structure of an organic electroluminescent device manufactured by phase-changing a solid phase-change material according to an embodiment of the present invention into a liquid state.

The present invention will be described in more detail below, which should be construed as illustrative and not limitative of the scope of the invention.

The term "organic electroluminescent compound" means a compound that can be used in an organic electroluminescent device, and includes at least one compound of a polymer, a low molecular weight, a quantum dot (quantum dot), and a monomolecular system, May be included in any layer constituting the device.

The term "organic electroluminescent material" as used herein means a material that can be used in an organic electroluminescent device, and may include at least one compound, and may be included in an arbitrary layer constituting an organic electroluminescent device . For example, the organic electroluminescent material may be a hole injecting material, a hole transporting material, a hole assisting material, a light emitting auxiliary material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, .

As used herein, the term " phase change material "means a material that can change from one phase (e.g., a solid state, a liquid state or a gaseous state) to another phase according to certain external conditions such as temperature, pressure, For example, it is a substance which can change from a solid state to a liquid state, or from a solid state or a liquid state to a gaseous state. The phase change material includes that the structure and / or performance is not changed before and after the phase change. Even if the phase change material changes structure and / or performance after a phase change, it may retain the original structure and / or performance or may have a new structure and / or performance if it returns to the original phase.

As used herein, the terms "carrier gas" and "induction gas" refer to a gas used for transporting, moving, spreading, blocking, inducing or transporting a predetermined substance. As used herein, the term " inducing gas " means a gas that can be injected with the phase change material in the vicinity of the output or output of the ink jet apparatus in the carrier gas. The carrier gas and the induction gas may each contain at least one of, for example, inert nitrogen at normal temperature, and generally inert argon, and may be the same or different from each other. Since the nitrogen and / or argon has a small reactivity with the phase change material and the air, the rate of causing the chemical reaction is low even when mixed with the phase change material or sprayed into the air. It is also not necessary to provide a separate device for removing nitrogen and / or argon after being sprayed with the phase change material.

As used herein, the term "ink jet apparatus " refers to a device for ejecting or ejecting a substance containing a substance in a liquid state. The ink jet apparatus of the present application can use, for example, at least one of a piezo method, a thermal bubble method, a bubble jet method and an aerosol jet method.

According to a first aspect of the present invention, in an ink jet apparatus or method for manufacturing an organic electroluminescent device using a phase change of a substance, the phase change material is phase-changed into a liquid state or a gaseous state, An electroluminescent compound. The phase change materials herein may be capable of one or more phase changes of melting, sublimation, vaporization, solidification and liquefaction due to temperature, pressure, or the like. The phase-change material of the present invention is a phase-change material which, from a solid state to a liquid state (liquid phase) or a sublimation from a solid state to a gaseous state (gaseous state) does not require much energy, It can be a substance. For example, the phase-change materials herein may be amorphous solids at room temperature, although their melting point is relatively low. The lower the melting point, the lower the probability that the chemical structure or physical properties will change due to the heating during melting.

Further, the phase change temperature or melting point of the phase change material can be lowered by mixing the organic electroluminescent compound with another specific substance or by blending specific organic electroluminescent compounds to form a phase change material. The mixture or blend included in the phase change material may be selected such that the phase change temperature or melting point of the phase change material is below the phase change temperature or melting point of the at least one organic electroluminescent compound included in the phase change material.

The phase change material of the present invention preferably changes phase at a relatively low temperature to prevent damage of the organic electroluminescent compound contained in the phase change material. In particular, the phase change temperature of the phase change material may be a temperature at which the chemical structure or physical properties of the organic electroluminescent compound does not change at the time of the phase change. In addition, the phase change temperature herein may be a temperature at which the phase change material remains in a phase-change state for a long time, but the material properties do not change and are not crystallized during the manufacturing process. According to one aspect of the present disclosure, the phase change temperature of the phase change material herein may be less than about 500 ° C, and in particular, the melting point at which the phase change material in a solid state changes to a liquid state may be less than about 500 ° C. When the phase change material has a melting point of about 500 캜 or less, the probability that the chemical structure or physical properties of the organic electroluminescent compound changes due to the heating during melting becomes low. According to one aspect of the present disclosure, the phase change temperature of the phase change material herein may be at least about 100 캜, preferably at least about 150 캜. When the phase change temperature is less than about 100 ° C, the material may be denatured due to heat generated when the manufactured device is driven, and the characteristics of the device itself may be deteriorated by the denatured material. When the phase change temperature is about 150 ° C or higher, the fabricated device has durability against heat denaturation generated during driving, and a stable device can be manufactured by reducing the phenomenon of crystallization of the material by heat. For example, the phase change temperature of the phase change material herein may be from about 100 DEG C to about 500 DEG C, preferably from about 150 DEG C to about 500 DEG C. However, the value of the phase change temperature may vary depending on the physical properties of the organic electroluminescent compound or other materials included in the phase change material, and the present invention is not limited by the above values.

The viscosity characteristics of the phase change material herein may play an important role in driving the ink jet apparatus for manufacturing the organic electroluminescent device of the present invention. Phase change materials having low viscosity properties can increase the rate of entry when the molten solid state material is transferred through the connection or nozzle of the device, thereby reducing the manufacturing time of the device. In addition, when the molten solid state phase change material is mixed, the mixed material can be made more uniform, and the pixel of the substrate can be made more precise when injected with the carrier gas at the nozzle .

In addition, the crystallization characteristics of the phase change material of the present invention may play an important role in driving an ink jet apparatus for manufacturing an organic electroluminescent device. Highly crystalline materials can cause clogging by forming crystals inside when solid phase phase material in the molten state is transferred through the joints or nozzles. Also, when the phase change material injected from the nozzle is solidified on the substrate, the highly crystalline material may cause an aggregation phenomenon, which may result in an uneven element and cause cracks. It is therefore desirable to make the amorphous form when the molten phase-change material forms a solid back to room temperature.

The phase-change material of the present invention may include a compound ordinarily included in an organic electroluminescent device, and may include materials that do not affect the melting characteristics of the phase-change material. Even when the phase-change material varies depending on the melting state, It can also include returning to the property. In addition, the phase change materials herein may additionally comprise any material capable of affecting the phase change, such as materials capable of promoting or retarding phase changes.

The phase change material herein may be an organic electroluminescent compound itself or may include at least one organic electroluminescent compound. For example, the phase-change material may be an organic electroluminescent compound itself, or may be composed of one kind of organic electroluminescent compound, or two or more kinds of organic electroluminescent compounds may be physically simply mixed without causing a substantial chemical reaction ≪ / RTI >

According to one aspect of the present invention, the organic electroluminescent compound may be a phase-changeable material that is not contained in the phase-change material. The organic electroluminescent compound of the present invention may be capable of at least one phase change of melting, sublimation, vaporization, solidification and liquefaction due to temperature or pressure. In addition, the organic electroluminescent compound can be obtained by melting from a solid state into a liquid state (liquid phase) or sublimation from a solid state or a liquid state to a gaseous state (vapor phase) The change can be a slow-moving substance. For example, the organic electroluminescent compound of the present invention may be an amorphous solid at room temperature even though its melting point is relatively low. The lower the melting point, the lower the probability that the chemical structure or physical properties will change due to the heating during melting. The organic electroluminescent compound of the present invention may be a compound ordinarily included in an organic electroluminescent device, and may return to the original characteristics at the time of film formation even if the phase of the compound changes due to temperature, pressure, or the like.

In addition, the organic electroluminescent compound of the present invention may be composed of an alkyl-based compound, a cycloalkyl-based compound, an aryl-based compound, a heteroaryl-based compound, an amine-based compound, a metal complex or a combination thereof, but is not limited thereto . According to an embodiment of the present invention, the organic electroluminescent compound may include at least one substituted or unsubstituted (3-30 membered) heteroaryl containing at least one member selected from nitrogen, sulfur and oxygen.

According to another aspect of the present invention, the molecular weight of the organic electroluminescent compound included in the phase change material of the present invention may be 10,000 or less. According to one aspect of the present invention, the organic electroluminescent compound included in the phase change material of the present invention may be at least one polymeric system, a low molecular system, a quantum dot (quantum dot) and / or a monomolecular system compound, Compound or quantum dot (quantum dot). Here, the high molecular weight compound means a compound having a molecular weight of about 10,000 or more, and the low molecular weight compound means a compound having a molecular weight of about 10,000 or less. Quantum Dots (quantum dots) are semiconductor nanoparticles that can utilize a change in electrical / optical properties as small single crystals of 2 to 10 nm in diameter, typically 15 to 150 atomic in size. Quantum dot can emit light of various colors by itself depending on crystal size and voltage. Quantum dot is composed of a core core and a shell. It can emit color differently depending on the size of the core. The core mainly contains cadmium selenide (CdSe), indium phosphide (InP) Silicon (Si) can be used.

According to one aspect of the present disclosure, the phase change material may comprise a phosphorescent dopant material, wherein the phosphorescent dopant material is selected from the group consisting of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) And a complex compound of a metal atom selected from the group consisting of According to another aspect of the invention, the phase change material herein may comprise a metal selected from cadmium (Cd), selenium (Se), zinc (Zn) and indium (In) Quantum dot material can be included.

According to the second aspect of the present invention, in the first aspect, the solvent may not be used in the phase change.

According to a third aspect of the present invention, in the first or second aspect, the ink jet apparatus for manufacturing an organic electroluminescent element includes a melting section for phase-changing a solid phase-change material to a liquid state, and a liquid phase- And an output to be injected with the induction gas and / or the carrier gas. In a solvent-free environment, the solid state phase change material in the melted portion of the ink jet apparatus for manufacturing an organic electroluminescence device can be changed into a liquid state due to temperature and / or pressure. The melted phase change material can be maintained in the melted state until it is continuously heated in the melted portion and discharged by the nozzle.

Here, the melting portion may include a heater capable of heating the phase change material to a desired temperature, and the heater may have a melting point of at least one of the organic electroluminescent compounds of one or more organic electroluminescent compounds contained in the phase change material Or the heat corresponding to the following temperature can be applied to the organic electroluminescent compound, and the heater preferably applies heat corresponding to a temperature lower than the melting point of the organic electroluminescent compound of one or more organic electroluminescent compounds, To a liquid state. The induction gas and / or carrier gas is preferably a gas which is low in reactivity and does not require a removal step. For example, the induction gas and / or carrier gas may comprise at least one of nitrogen and argon, respectively. The induction gas and the carrier gas may be the same material or at least a part of the constituent components may be different from each other.

The induction gas may include at least one of nitrogen and argon. The output unit may inject the induction gas in a form surrounding the liquid phase change material. Further, the output unit may start injecting the phase change material in the liquid state after starting the injection of the induction gas. By injecting a liquid phase phase change material together with an induction gas and / or a carrier gas, the liquid phase phase change material can be applied closer to the desired shape.

According to a fourth aspect of the present invention, in any one of the first to third aspects, the method for manufacturing an organic electroluminescent device includes the steps of phase-changing a solid phase-change material into a liquid state, And injecting the material with an induction gas and / or a carrier gas.

Here, the step of phase-changing the solid phase-change material into a liquid state may include the step of changing the phase of the phase-change material to a liquid phase by adding at least one of the organic electroluminescent compounds of the at least one organic electroluminescent compound The phase change material may be phase-changed into a liquid state. The induction gas may include at least one of nitrogen and argon. The step of injecting the liquid phase-change material together with the induction gas and / or the carrier gas may inject the induction gas in a form surrounding the liquid phase-change material. In addition, the step of injecting the liquid phase material and / or the carrier gas may start the injection of the liquid phase material after starting the injection of the induction gas. By injecting a liquid phase phase change material together with an induction gas and / or a carrier gas, the liquid phase phase change material can be applied closer to the desired shape.

According to a fifth aspect of the present invention, in any one of the first to fourth aspects, the phase-change material comprises a compound represented by the following formula (1), or the organic electroluminescence The compound may include a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

은 치환 또는 비치환된 모노- 또는 디- (C6-C30)아릴아미노, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이고; 상기 치환 또는 비치환된 (3-30원)헤테로아릴은 질소, 황 및 산소로 이루어진 그룹에서 선택되는 하나 이상을 포함할 수 있으며,

Is a substituted or unsubstituted mono- or di- (C6-C30) arylamino, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl; The substituted or unsubstituted (3-30 membered) heteroaryl may include at least one member selected from the group consisting of nitrogen, sulfur and oxygen,

M is substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered heteroaryl, or substituted or unsubstituted (C3-C30) cycloalkyl;

n and m are each an integer of 0 to 3;

는 서로 동일하거나 상이할 수 있고, m이 2 또는 3일 때, 복수의 M은 서로 동일하거나 상이할 수 있다.When n is 2 or 3,

May be the same as or different from each other, and when m is 2 or 3, the plurality of M may be the same or different from each other.

The compound represented by the formula (1) may be represented by the following formula (2) or (3).

(2)             (3)

In Formula 2, X is carbon, nitrogen, oxygen, sulfur, phosphorus, or silicon; Ar ₁ to Ar ₃ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, (C1-C30) alkylsilyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri Substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, C30) arylamino; Ar ₁ , Ar ₂ and Ar ₃ may be connected to form a ring of a substituted or unsubstituted (C3-C30) monocyclic or polycyclic alicyclic group, aromatic group or a combination thereof, and the alicyclic group, Or a combination thereof may contain one or more heteroatoms selected from nitrogen, oxygen and sulfur, and p is an integer from 0 to 2; When p is 2, Ar < ₃ > may be the same or different from each other.

In Formula 3, X ₁ to X ₅ are each independently N or CR ₁ ; R ₁ is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) Substituted or unsubstituted (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkoxy, (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri Substituted or unsubstituted (C1-C30) alkyl (C6-C30) alkylamino, substituted or unsubstituted mono- or di- Amino; Adjacent to the R ₁ connected to each other, a substituted or unsubstituted monocyclic of unsubstituted (C3-C30) or polycyclic aliphatic, aromatic, or may form a ring in combination thereof, the formed alicyclic, aromatic or combinations thereof, The ring may contain one or more heteroatoms selected from nitrogen, oxygen and sulfur.

In the formulas herein, heteroaryl (phen) and heterocycloalkyl may each independently comprise one or more heteroatoms selected from B, N, O, S, Si and P. (C6-C30) aryl, substituted or unsubstituted (5-30 membered) heterocycloalkyl, substituted or unsubstituted (C1-C30) Substituted or unsubstituted (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkoxy, (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri Substituted or unsubstituted (C1-C30) alkyl (C6-C30) alkylamino, substituted or unsubstituted mono- or di- Amino, and the like.

, M, Ar₁ 내지 Ar₃, 및 X₁ 내지 X₅에서, 치환된 (C1-C30)알킬, 치환된 (C6-C30)아릴, 치환된 (3-30원)헤테로아릴, 치환된 (C3-C30)시클로알킬, 치환된 (C1-C30)알콕시, 치환된 트리(C1-C30)알킬실릴, 치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환된 (C1-C30)알킬디(C6-C30)아릴실릴, 치환된 트리(C6-C30)아릴실릴, 치환된 모노- 또는디- (C1-C30)알킬아미노, 치환된 모노- 또는 디- (C6-C30)아릴아미노, 치환된 (C1-C30)알킬(C6-C30)아릴아미노, 및 치환된 (C3-C30)의 단일환 또는 다환의 지환족, 방향족 또는 이들의 조합의 고리의 치환체는 각각 독립적으로 중수소, 할로겐, 시아노, 카르복실, 니트로, 히드록시, (C1-C30)알킬, 할로(C1-C30)알킬, (C2-C30)알케닐, (C2-C30)알키닐, (C1-C30)알콕시, (C1-C30)알킬티오, (C3-C30)시클로알킬, (C3-C30)시클로알케닐, (3-7원)헤테로시클로알킬, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C6-C30)아릴로 치환 또는 비치환된 (5-30 원)헤테로아릴, (5-30원)헤테로아릴로 치환 또는 비치환된 (C6-C30)아릴, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, 아미노, 모노- 또는 디- (C1-C30)알킬아미노, (C1-C30)알킬로 치환 또는 비치환된 모노- 또는 디- (C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, (C1-C30)알킬카보닐, (C1-C30)알콕시카보닐, (C6-C30)아릴카보닐, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬, 및 (C1-C30)알킬(C6-C30)아릴로 이루어진 군으로부터 선택되는 하나 이상일 수 있다."Substituted" in the context of "substituted or unsubstituted" as used herein means that a hydrogen atom in a functional group is replaced by another atom or another functional group (ie, a substituent). In the above formulas (1) to (3)

, M, Ar ₁ to Ar ₃ , and X ₁ To X in _5, substituted (C1-C30) alkyl, substituted (C6-C30) aryl, substituted (3-30 membered) heteroaryl, substituted (C3-C30) cycloalkyl, substituted (C1-C30 (C6-C30) arylsilyl, substituted (C1-C30) alkylsilyl, substituted di (C1-C30) (C6-C30) arylsilyl, substituted mono- or di- (C1-C30) alkylamino, substituted mono- or di- C30) arylamino, and substituted (C3-C30) monocyclic or polycyclic alicyclic, aromatic, or combinations thereof, are each independently selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, (C 1 -C 30) alkyl, halo (C 1 -C 30) alkyl, (C 2 -C 30) alkenyl, (C 2 -C 30) alkynyl, (C6-C30) arylthio, (C6-C30) aryl, (C6-C30) arylthio, (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, unsubstituted (5-30 membered) heteroaryl, (5-30 membered) heteroaryl- (C1-C30) alkylsilyl, amino, mono- or di- (C1-C30) alkylamino, (C1-C30) (C6-C30) arylamino, (C1-C30) alkylcarbonyl, (C1-C30) alkoxy (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, di (C6-C30) arylboronyl, di (C6-C30) aryl (C1-C30) alkyl, and (C1-C30) alkyl (C6-C30) aryl.

According to a sixth aspect of the present invention, in any one of the first to fifth aspects, the organic electroluminescent compound is at least one selected from the group consisting of iridium (Ir), osmium (Os), copper (Cu) A complex compound or a metal selected from cadmium (Cd), selenium (Se), zinc (Zn) and indium (In).

According to a seventh aspect of the present invention, in any one of the first to sixth aspects, the phase-change material includes at least one organic electroluminescent compound, and the phase- At a temperature, the phase change material can be phase-changed from a solid state to a liquid state.

According to one aspect of the present invention, it is possible to lower the phase change temperature or the melting point of the phase change material by mixing the organic electroluminescent compound with another specific material or by blending specific organic electroluminescent compounds to form a phase change material. The phase change temperature or melting point of the phase change material may be below the phase change temperature or melting point of the organic electroluminescent compound contained in the phase change material. This makes it possible to provide an organic electroluminescent compound which maintains the molten state for a long time and does not change the material properties and does not crystallize during the manufacturing process. Specifically, the melting point of the phase-change material comprising at least one organic electroluminescent compound is lower than or equal to the melting point of any one of the at least one organic electroluminescent compound, or the melting point of any one of the at least one organic electroluminescent compound ≪ / RTI > Further, the melting point of the phase-change material containing two or more organic electroluminescent compounds may be lower than the arithmetic average value of the melting point of each of the two or more organic electroluminescent compounds. According to one aspect of the present application, by melting the phase change material of the present invention at a relatively low temperature, damage of the organic electroluminescent compound contained in the phase change material can be prevented, and cost and / or time due to energy saving can be saved have.

According to an eighth aspect of the present invention, there is provided an organic electroluminescent device comprising the phase change material according to any one of the first to seventh aspects. The phase change material may be at least one selected from the group consisting of a light emitting layer, a hole injecting layer, a hole transporting layer, a hole transporting layer, a light emitting auxiliary layer, an electron transporting layer, an electron buffer layer, an electron injecting layer, But the present invention is not limited thereto.

The term "(C 1 -C 30) alkyl" as used herein means straight-chain or branched alkyl having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10 . Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. As used herein, "(C2-C30) alkenyl" means straight or branched chain alkenyl having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, 10. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. As used herein, "(C2-C30) alkynyl" means straight chain or branched chain alkynyl having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, 10. Examples of the alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl and 1-methylpent-2-onyl. The term "(C3-C30) cycloalkyl" as used herein means a single ring or polycyclic hydrocarbon having 3 to 30 ring skeletal carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. Refers to a group consisting of B, N, O, S, Si and P, preferably O (O) , S and N, and includes, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. As used herein, "(C6-C30) aryl" means a single ring or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeletal carbon atoms and may be partially saturated. The number of carbon atoms in the ring skeleton is preferably 6 to 25, more preferably 6 to 18. The aryl includes those having a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, Naphthyl, naphthyl, phenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, crycenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl and the like. As used herein, "(3-30) heteroaryl" means an aryl group having at least one heteroatom selected from the group consisting of B, N, O, S, Si and P having 3 to 30 ring skeletal atoms. The number of heteroatoms is preferably 1 to 4, and may be a single ring system or a fused ring system condensed with at least one benzene ring, and may be partially saturated. In addition, the heteroaryl in the present application includes a heteroaryl group having one or more heteroaryl or aryl groups connected to a heteroaryl group by a single bond, and having a spiro structure. Examples of such heteroaryls include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl , Monocyclic heteroaryl such as triazolyl, tetrazolyl, furanzyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzoimidazolyl, benzothiazolyl, benzothiazolyl, benzoisothiazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, Fused ring heteroaryl such as furanyl, quinazolinyl, quinazolinyl, quinazolinyl, carbazolyl, benzocarbazolyl, phenoxaphyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacrylidinyl and the like. As used herein, "halogen" includes F, Cl, Br, and I atoms.

The dopant material applied to the organic electroluminescent device of the present application may be a fluorescent or phosphorescent dopant material, and is not particularly limited. The fluorescent dopant material may comprise a substituted or unsubstituted mono- or di- (C6-C30) arylamino. The phosphorescent dopant material may be a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and may be iridium (Ir), osmium (Os) (Cu) and platinum (Pt) are preferable, and an orthometallated iridium complex compound is more preferable. The compound used as such a dopant material may be an organic electroluminescent compound included in the phase change material of the present invention.

According to one aspect of the present invention, the complex compound of the metal atom may be a compound represented by the following formula (101).

(101)

In the above formula (101)

L is selected from the following structures 1 or 2;

[Structure 1] [Structure 2]

R ₁₀₀ to R ₁₀₃ are each independently selected from the group consisting of hydrogen, deuterium, halogen, (C 1 -C 30) alkyl substituted or unsubstituted with halogen, substituted or unsubstituted (C 3 -C 30) cycloalkyl, C30) aryl, cyano, substituted or unsubstituted (C3-C30) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; R ₁₀₀ to R ₁₀₃ may form a fused ring in which adjacent substituents are connected to each other to form a substituted or unsubstituted fused ring, and examples thereof include substituted or unsubstituted quinoline, substituted or unsubstituted benzofuro pyridine, substituted or unsubstituted benzo Thienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzopyrroquinoline, substituted or unsubstituted benzothienoquinolines, or substituted or unsubstituted indenoquinolines;

R ₁₀₄ to R ₁₀₇ are each independently selected from the group consisting of hydrogen, deuterium, halogen, (C 1 -C 30) alkyl substituted or unsubstituted with halogen, substituted or unsubstituted (C 3 -C 30) cycloalkyl, C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; R ₁₀₄ to R ₁₀₇ may form a fused ring in which adjacent substituents are connected to each other to form a substituted or unsubstituted fused ring, and examples thereof include substituted or unsubstituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted di Benzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine;

R ₂₀₁ to R ₂₁₁ each independently represents hydrogen, deuterium, halogen, (C 1 -C 30) alkyl substituted or unsubstituted with halogen, substituted or unsubstituted (C 3 -C 30) cycloalkyl, or substituted or unsubstituted -C30) aryl, and adjacent substituents may be connected to each other to form a substituted or unsubstituted fused ring;

n is an integer of 1 to 3;

While the various examples presented herein describe various layers as comprising a single material, a combination of materials such as a mixture of a host and a dopant, or more generally a mixture, may be used. In addition, the layer may have various sublayers. In addition, the OLED can be described as having an "organic layer" disposed between the cathode and the anode. This organic layer may consist of a single layer or may comprise a plurality of layers of different organic materials.

1 schematically shows an ink jet apparatus for manufacturing an organic electroluminescent device by phase-changing a solid phase-change material according to an embodiment of the present invention into a liquid state. Hereinafter, an ink jet apparatus for manufacturing an organic electroluminescent device according to an embodiment of the present invention will be described with reference to FIG.

Referring to FIG. 1, an ink jet apparatus for manufacturing an organic electroluminescent device may include an input unit 110, a first connection unit 120, a melting unit 130, a second connection unit 140, and an output unit 150. The ink jet apparatus for manufacturing an organic electroluminescent device of the present invention is not limited to the embodiment shown in Fig. For example, the ink jet apparatus for manufacturing an organic electroluminescent device may include only the melting unit 130 and the output unit 150. In addition to the units shown in FIG. 1, the apparatus may further include at least one of a display unit, a communication unit, a sensing unit, and a control unit.

One ink jet apparatus for manufacturing an organic electroluminescent device may include one or more input units 110. The input unit 110 may include one or more injection ports. The organic electroluminescent compound or the phase change material containing the organic electroluminescent compound may be injected from the outside into the liquid or solid state through the input unit 110. [ The input unit 110 may be referred to as a loading chamber or an ink loader or the like. When the input unit 110 includes a plurality of injection ports, different materials may be injected through each injection port. The input unit 110 may be omitted or included in the melting unit 130.

The first connection unit 120 may control the phase change material transferred through the input unit 110 to move to the melting unit 130. Under certain conditions, the control unit 120 can retain the phase change material without moving it. The specific condition includes at least one of the volume (mass) of the phase change material held in the input section 110 or the first connection section 120, the user's input, a predetermined pressure range, a predetermined temperature range and a predetermined time .

The first connection unit 120 may receive or convey the phase change material transferred from the input unit 110 in a solid state. When transporting different phase change materials, the first connection portion 120 may be configured to transport the phase change material through a plurality of paths, respectively. According to an embodiment of the present invention, when the phase change material provided from the input unit 110 is not in a solid state, the first connection unit 120 may change the phase change material to a solid state through cooling. The first connection part 120 transfers the phase change material from the input part 110 to the melting part 130 according to whether the condition of the delivered phase change material is satisfied with respect to volume (mass), temperature, pressure, . The first connection part 120 may include a gate valve that can be opened and closed, and may control the transfer of the phase change material through the gate valve.

In the present invention, the first connection part 120 may be an optional component and may be omitted to realize the invention. The first connection part 120 may be included in the fused part 130.

The molten portion 130 heats the solid state phase change material containing the organic electroluminescent compound to phase change to a liquid state. The phase change material may be phase-changed into a liquid state at a temperature lower than the melting point of the organic electroluminescent compound by further comprising a suitable separate material that does not act as a solvent for the organic electroluminescent compound. For example, if the phase change material comprises at least one organic electroluminescent compound, the heat applied may correspond to a temperature below the melting point of any one of the at least one organic electroluminescent compound You can configure it. Alternatively, if the phase-change material comprises two or more organic electroluminescent compounds, the applied heat may correspond to a temperature lower than an arithmetic mean value of the melting point of each of the two or more organic electroluminescent compounds. The molten portion 130 may also be referred to as a melting chamber or a heater. The melted portion 130 may transfer the melted phase change material to the output portion 150 through the second connection portion 140 or directly.

The second connection part 140 connects the melted part 130 and the output part 150 and the second connection part 140 controls the phase change material to be maintained in a liquid state in the second connection part 140 . The second connection unit 140 may be formed in a manner such that the phase change material contacts the melted portion 130 depending on the conditions such as volume (mass), temperature, pressure, time or user input of the phase change material transferred to the second connection unit 140, To the output unit 150. The second connection portion 140 may include a gate valve that can be opened and closed, and can control the transfer of the phase change material through the gate valve. The second connection unit 140 and / or the first connection unit 120 may be opened and closed by a separate control unit.

Here, the second connection portion 140 is an optional component and may be omitted to implement the present invention. The second connection part 140 may be included as a part of the melting part 130 or the output part 150.

The output unit 150 may output the melted phase change material in a form of injection or the like in the melted portion 130. The output unit 150 may be referred to as a printer head, a radiation unit, or the like. The output unit 150 can continuously heat the melted phase change material to prevent the melted phase change material from solidifying until output. The output unit 150 may include one or more nozzles for ejecting the phase change material in a molten state onto a substrate or the like. The one or more nozzles may be configured to be attached to the output unit 150, respectively.

The at least one nozzle may mix the molten phase change material in the carrier gas to form an aerosol mist. The carrier gas may also be utilized as a means for applying pressure to move the phase change material into the nozzle within the output section 150.

The one or more nozzles may inject the molten phase change material and the induction gas together. The nozzle may inject the induction gas in a form surrounding the liquid phase change material. The induction gas may also be referred to as a sheath gas, and the injected phase change material may be induced to uniformly coat the substrate.

For sophisticated application, each nozzle may be configured to initiate injection of the liquid phase phase change material after a predetermined time (e.g., 0.5 second) has elapsed since initiating the injection of the induction gas . Alternatively, each nozzle may simultaneously initiate injection of the induction gas and the phase change material in the liquid state.

FIG. 2 illustrates a method of manufacturing an organic electroluminescent device by phase-changing a solid phase-change material according to an embodiment of the present invention into a liquid state. Hereinafter, a method of manufacturing an organic electroluminescent device according to an embodiment of the present invention will be described with reference to FIG.

Step 210 is a step of receiving a phase change material from the outside. For example, the input portion may have one or more injection ports, and the same or different compound may be provided through each injection port. The supplied phase change material may correspond to a solid state or a liquid state. Meanwhile, according to another aspect of the present disclosure, step 220 may be performed immediately for a phase change material at a particular location without step 210. [

Step 220 is a step of heating the phase-change material in a solid state including the organic electroluminescent compound to phase-change into a liquid state. The heating may be performed on the phase change material existing at a specific position without the supply of the step 210. The phase-change material may be phase-changed into a liquid state at a temperature lower than the melting point of the organic electroluminescent compound by further including a separate material that does not act as a solvent for the organic electroluminescent compound. The heat applied may correspond to a temperature below the melting point of any one of the at least one organic electroluminescent compound when the phase change material comprises at least one organic electroluminescent compound. have. Alternatively, the heat applied may correspond to a temperature lower than an arithmetic average value of melting points of the two or more organic electroluminescent compounds when the phase-change material includes two or more organic electroluminescent compounds.

An apparatus for performing an organic electroluminescent device manufacturing method can heat a phase change material when a predetermined condition is satisfied. The predetermined condition includes an environment at a specific location of the apparatus. The environment may include, for example, at least one of the volume (mass), temperature, pressure, time and user input of the phase change material.

Step 230 is a step of injecting the phase-change material in a liquid state together with the induction gas. For example, the phase change material may be injected through a nozzle (aerosol method). The phase change material may be emitted from the nozzle along with the induction gas. The induction gas may be injected in a manner surrounding the phase change material.

The injected phase-change material may be applied to at least one layer of the substrate of the organic electroluminescent device or the organic electroluminescent device to form a film.

Unlike the step 230 in which the phase change material is injected together with the induction gas, the carrier gas may be injected together with the phase change material. In this case, the carrier gas may be mixed with the phase change material and injected. In addition, when the phase change material is injected, both the induction gas and the carrier gas may be injected.

FIG. 3 shows the structure of an ink jet device for manufacturing an organic electroluminescent device by phase-changing a solid phase-change material according to an embodiment of the present invention into a liquid state. Hereinafter, the operation of the ink jet apparatus for fabricating an organic electroluminescent device according to an embodiment of the present invention will be described with reference to FIG.

Referring to FIG. 3, the ink jet apparatus for manufacturing an organic electroluminescent device may include an input unit 310 and a first connection unit 350.

The input unit 310 temporarily stores the phase change materials 320, 330, and 340 supplied through the injection port 360. The cross section of the inner wall of the input unit 310 may have a circular shape, an elliptical shape, a rectangular shape, or a polygonal shape. The phase change materials 320, 330, and 340 supplied to the input unit 310 may have a predetermined shape such as a rectangular parallelepiped, a cylinder, and the like.

Although the input unit 310 has only one injection port in FIG. 3, the input unit may have two or more injection ports. Unlike Fig. 3, the injection port may be open in a direction other than the vertical direction. In FIG. 3, one unit of phase change material remains at the same height, but two or more phase change materials may be stacked at the same height. Meanwhile, the phase change material may be supplied in powder form.

The first connection unit 350 transfers the phase change material from the input unit 310 to the melting unit 370 according to whether the conditions such as temperature, pressure, time, or user input are satisfied. The phase change material before being transferred to the melted portion is stored in the input unit 310. The first connection portion 350 of FIG. 3 moves in the horizontal direction, thereby opening / closing the passage to the molten portion. By the movement of the first connection part 350, the phase change material is sequentially transferred from the lowermost phase change material 340 to the melting part 370. In FIG. 3, the first connecting part 350 is shown reciprocally moving in the horizontal direction, but the present invention is not limited thereto. Meanwhile, the first connection part 350 may be implemented as a form including a valve that can be opened and closed. In this case, the phase change material may pass through the first connection portion 350 in a liquid state. Figure 4 shows a first connection comprising a valve.

The ink jet apparatus for manufacturing an organic electroluminescent device of the present application is not limited to the embodiment shown in Fig. 3, the phase change material may be transferred in a direction other than the vertical direction. The input 310 may also include one or more protrusions for securing the phase change material to a specific position when the phase change material is not in motion.

According to another aspect of the present disclosure, the input 310 and / or the first connection 350 may be further simplified or omitted. When both the input unit 310 and the first connection unit 350 are omitted, the ink jet apparatus for fabricating an organic electroluminescent device according to the present invention directly heats the phase change material at a specific position before movement.

Fig. 4 shows the structure of an ink jet device for manufacturing an organic electroluminescent device by phase-changing a solid phase-change material according to an embodiment of the present invention into a liquid state. Hereinafter, an operation of the ink jet apparatus for manufacturing an organic electroluminescent device according to an embodiment of the present invention will be described with reference to FIG.

Referring to FIG. 4, the ink jet apparatus for manufacturing an organic electroluminescent device may include a first connection portion 410, a fused portion 420, and a second connection portion 450. The ink jet apparatus for manufacturing an organic electroluminescent device of the present application is not limited to the embodiment shown in Fig. For example, the first connection part 410 or the second connection part 450 may be simplified or omitted. Unlike Fig. 4, the phase change material may be implemented to be transmitted in a direction other than the vertical direction.

The phase change material 405 transferred from the input unit is transferred to the melting unit 420 through the first connection unit 410. The first connection part 410 may include a valve 415 capable of opening and closing. The first connection part 410 allows the phase change material 405 to be transferred from the input part to the melting part 420 according to whether the conditions such as temperature, pressure, time, or user input are satisfied.

Molten portion 420 includes a heater 425 for melting the phase change material in solid form in liquid form. According to an embodiment, the molten portion 420 includes an agitator 430 for agitating the phase change ink, a hole 435 for escaping the molten ink, an ablation film 440 for allowing the ink to be fixed until the molten ink is melted, And a collector 445 for collecting the phase change material for transfer to the second connection. When a plurality of materials are transferred through the first connection part 410, the plurality of materials may be mixed through the agitator 430 to form a blend. In FIG. 4, the second connection part 450 is a bottleneck type, but is not limited thereto.

The phase change material transferred from the fused portion 420 is transferred to the output portion 420 through the second connection portion 450. The second connection portion 450 may include a valve 455 that can be opened and closed.

The hole 435 may be formed to be opened or closed depending on whether the condition of the volume (mass), temperature, pressure, time, or user input of the melted phase change material in the melted portion 420 is satisfied. The collector 445 and / or the second connection 450 may include equipment to continue heating the molten phase change material to a solid state.

FIG. 5 shows a configuration of an ink jet apparatus for manufacturing an organic electroluminescent device by phase-changing a solid phase-change material according to an embodiment of the present invention into a liquid state. Hereinafter, the operation of the ink jet apparatus for fabricating an organic electroluminescent device according to an embodiment of the present invention will be described with reference to FIG.

5, an ink jet apparatus for manufacturing an organic electroluminescent device may include a second connection unit 510, an output unit 520, and nozzles 545 and 550. The ink jet apparatus for manufacturing an organic electroluminescent device of the present application is not limited to the embodiment shown in Fig. Unlike Fig. 5, the phase change material may be implemented to be transmitted and injected in a direction other than the vertical direction. On the other hand, the nozzles 545 and 550 may be defined as being part of the output section.

The phase change material 505 transferred from the melted portion is transferred to the output unit 520 through the second connection unit 510. The second connection portion 510 may include a valve 515 capable of opening and closing.

According to an aspect, the output unit 520 includes a heater 530 that maintains the temperature of the molten phase change material so that the molten phase change material does not become a solid, a bottom surface 535 that stores the phase change material until the phase change material is discharged through the nozzle, And a first inlet 525 for injecting gas. The carrier gas injected through the first injection port 525 can increase the pressure in the output section 520 so that the phase change material can be injected through the nozzle. In addition, the carrier gas may be mixed with the phase change material and injected with the phase change material through the nozzles 545, 550 in a state that the carrier gas is not dissolved in the phase change material.

The nozzles 545 and 550 may include a nozzle upper end 545 corresponding to a relatively narrow passage and a nozzle lower end 550 corresponding to a relatively wide passage. In FIG. 4, the nozzle is divided into two sections according to the area of the cross section, but the present invention is not limited thereto. For example, the cross section of the nozzle may be equal to or greater than three cross sectional areas in all sections.

The nozzles 545 and 550 may further include a second injection port 540 for injecting the induction gas 555 according to the embodiment. The induction gas 555 injected through the second injection port 540 may be injected together with the phase change material 560 in a liquid state.

Meanwhile, the ink jet apparatus according to an aspect of the present invention may include a plurality of nozzles. In this case, the widths of the cross sections of the respective nozzles may be equal to or different from each other. For example, the ink jet apparatus may include a first nozzle having a relatively large cross section and a middle portion, and a plurality of second nozzles having a relatively narrow cross section and surrounding the cross section. According to another aspect of the present invention, at least one of the first nozzle or the plurality of second nozzles may be configured not to inject the induction gas.

5, the injection angle of the induction gas 555 and the phase change material 560 is the same, but the injecting angles of the induction gas 555 and the phase change material 560 may be different from each other. For example, the phase change material 560 is injected perpendicularly to the substrate while the induction gas 555 injected on both sides of the phase change material 560 is tilted 15 degrees toward the phase change material 560 .

5 shows that the cross section of the nozzle is circular and the induction gas 555 is injected in a form surrounding the phase change material 560. [ According to another aspect of the invention, the cross section of the nozzle may have the shape of an ellipse or a polygon. According to another aspect of the present disclosure, the induction gas 555 may be injected in contact with the phase change material 560 only partially. For example, in a nozzle having a rectangular cross section, the induction gas 555 may be injected while contacting the phase change material only at each vertex of the quadrangle. Alternatively, in the nozzle having the elliptical cross section, the induction gas 555 may be injected while being in contact with the phase change material only in a region where the curvature value of the ellipse is within a certain range.

5, the carrier gas introduced through the first injection port 525 can be used to apply pressure to inject the phase change material through the nozzle, and the induction gas introduced through the second injection port 540 Can be used for finely applying a phase change material to a substrate.

FIG. 6 schematically shows the structure of an organic electroluminescent device manufactured by phase-changing a solid phase-change material according to an embodiment of the present invention into a liquid state. Hereinafter, an organic electroluminescent device according to one aspect of the present invention will be described with reference to FIG.

6, an organic electroluminescent device 600 includes a substrate 610, a first electrode 620 formed on the substrate 610, an organic layer 630 formed on the first electrode 620, and an organic layer 630 And a second electrode 640 facing the first electrode 620 with a gap therebetween.

The organic layer 630 includes a hole injecting layer 631, a hole transporting layer 632 formed on the hole injecting layer 631, a light emitting layer 633 formed on the hole transporting layer 632, A buffer layer 634 and an electron transfer zone 637 formed on the electron buffer layer 634 and the electron transfer zone 637 may include an electron transfer layer 635 formed on the electron buffer layer 634 and an electron transfer layer 637 formed on the electron transfer layer 634. [ And an electron injection layer 636 formed on the layer 635.

Hereinafter, an organic electroluminescent device is manufactured using the phase change material of the present invention for a detailed understanding of the present invention. However, the present invention is not limited to the following examples.

[device Manufacturing example  1 to 3]

First, a compound Plexcore AQ 1200 was coated on the anode of a transparent electrode ITO thin film having a thickness of 1500 ANGSTROM by spin coating to a thickness of 400 ANGSTROM to form a hole injection layer. Subsequently, the mixture of the host and the dopant described in Table 1 below was melted using the ink jet apparatus of the present invention, and the mixture was sprayed on the hole injection layer to form a light emitting layer with a thickness of about 800 nm. Thereafter, Compound ET-1 and Compound EI-1 were evaporated at a rate of 4: 6 to deposit an electron transport layer having a thickness of 350 ANGSTROM on the light emitting layer. Subsequently, Compound EI-1 was deposited on the electron transport layer to a thickness of 20 ANGSTROM as an electron injection layer, and then an Al cathode was deposited on the electron injection layer to a thickness of 800 ANGSTROM to prepare an OLED device.

[Table 1]

The compounds used in the device preparation examples are as follows.

It was confirmed from the above device manufacturing examples that an organic electroluminescent device can be manufactured without using a solvent by phase-changing the solid phase-change material into a liquid state and injecting it.

Claims (9)

A phase change material that is phase-changed from a solid state to a liquid state and comprises at least one organic electroluminescent compound in an ink jet apparatus or method for producing an organic electroluminescent device using a phase change of a material. The phase change material of claim 1, wherein no solvent is used in the phase change. 2. The phase change material of claim 1, wherein the ink jet apparatus comprises a melt section for phase-changing the solid phase-change material to a liquid phase, and an output section for jetting the liquid phase phase-change material along with the induction gas. The method of claim 1, wherein the method of fabricating the organic electroluminescent device comprises: phase-changing a solid phase-change material to a liquid phase; and injecting a liquid phase phase- Phase change material. The phase change material according to claim 1, wherein the organic electroluminescent compound comprises a compound represented by the following formula (1).
[Chemical Formula 1]

In Formula 1,

Is a substituted or unsubstituted mono- or di- (C6-C30) arylamino, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl;
M is substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered heteroaryl, or substituted or unsubstituted (C3-C30) cycloalkyl;
n and m are each an integer of 0 to 3;
When n is 2 or 3,

May be the same as or different from each other, and when m is 2 or 3, a plurality of Ms may be the same or different from each other.
The phase change material according to claim 5, wherein the compound represented by the formula (1) is represented by the following formula (2) or (3).
[Chemical Formula 2] < EMI ID =

In Formula 2,
X is carbon, nitrogen, oxygen, sulfur, phosphorus or silicon,
Ar ₁ to Ar ₃ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, (C1-C30) alkylsilyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri Substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, C30) arylamino; Ar ₁ , Ar ₂ and Ar ₃ may be connected to form a ring of a substituted or unsubstituted (C3-C30) monocyclic or polycyclic alicyclic group, aromatic group or a combination thereof, and the alicyclic group, Or a combination thereof may contain one or more heteroatoms selected from nitrogen, oxygen and sulfur,
p is an integer of 0 to 2,
when p is 2, Ar < ₃ > may be the same or different from each other;
In Formula 3,
X ₁ to X ₅ are each independently N or CR ₁ ,
R ₁ is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) Substituted or unsubstituted (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkoxy, (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri Substituted or unsubstituted (C1-C30) alkyl (C6-C30) alkylamino, substituted or unsubstituted mono- or di- Amino; Adjacent to the R ₁ connected to each other, a substituted or unsubstituted monocyclic of unsubstituted (C3-C30) or polycyclic aliphatic, aromatic, or may form a ring in combination thereof, the formed alicyclic, aromatic or combinations thereof, The ring may contain one or more heteroatoms selected from nitrogen, oxygen and sulfur. 7. Compounds according to claim 5 or 6, wherein said substituted (C1-C30) alkyl, substituted (C6-C30) aryl, substituted (3-30 membered heteroaryl, (C6-C30) alkylsilyl, substituted di (C1-C30) alkylsilyl, substituted di (C1- (C6-C30) arylsilyl, substituted mono- or di- (C1-C30) alkylamino, substituted mono- or di- (C6-C30) arylamino, and substituted (C3-C30) monocyclic or polycyclic alicyclic, aromatic, or combinations thereof, are each independently selected from the group consisting of deuterium, halogen, cyano, (C1-C30) alkyl, (C1-C30) alkyl, (C2-C30) alkenyl, (C6-C30) arylthio, (C6-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3-7 membered) heterocycloalkyl, (C6-C30) aryl, tri (C1-C30) alkylsilyl, tri (C6-C30) heteroaryl which is substituted or unsubstituted with (C1-C30) alkylsilyl, amino, mono- or di- (C1-C30) alkylamino (C6-C30) arylamino, (C1-C30) alkylcarbonyl, (C1-C30) (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, di (C6-C30) arylboronyl, di (C6-C30) aryl (C1-C30) alkyl, and (C1-C30) alkyl (C6-C30) aryl. The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound is a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), or a complex compound of cadmium (Cd), selenium (Se) , Zinc (Zn), and indium (In). An organic electroluminescent device comprising the phase change material according to claim 1.

Images