JP2018150246A - Organic compound deposition method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a purification method which prevents quality of an ion liquid from being deteriorated with time due to purification for reducing time for exchange operations of the ion liquid or exchange frequency of the ion liquid as much as possible without reducing purification purity of a purified organic compound.SOLUTION: It can be solved by an organic compound deposition method having a gasification process S1 for gasifying an organic compound OC mounted in a gasification chamber 1 by heating with a heating device 2 at a reduced pressure state, a transportation process S2 for transferring the gasified organic compound OC with inert gas to a discharge part 3 projecting from the gasification chamber 1, and a deposition process S3 for depositing the organic compound OC from an ion liquid IL in a deposition container 4 in which the ion liquid IL to which the discharge part 3 is in contact is filled, in which a reductant which reacts with oxygen existing in the gasification chamber 1 or the ion liquid IL exists in the gasification chamber 1 or the ion liquid IL.SELECTED DRAWING: Figure 1

Description

  The present invention relates to a crystal growth method and a purification method of an organic compound such as an organic semiconductor used in an organic EL.

  For organic compounds such as organic semiconductors, various methods for producing crystals such as single crystals with higher purity have been studied in order to greatly reduce performance when a small amount of impurities are used as an electronic device.

  Conventionally, in order to purify organic compounds used in electronic devices as organic semiconductors, etc., the organic compounds are dissolved in a solvent, and the solubility of the organic compound in the solvent is measured using physical changes in the solvent such as temperature difference and solvent evaporation. A method of depositing a desired organic compound as a crystal using the difference has been performed. In recent years, a purification method in which an organic compound is sublimated under reduced pressure using a heat source and then precipitated in an ionic liquid has been performed.

  In Patent Document 1, an organic material used for an organic light-emitting diode is heated and sublimated in a vacuum atmosphere, and the sublimation gas is sent with an inert gas such as nitrogen, and then contacted with the surface of an ionic liquid or A purification method in which recrystallization is performed with an ionic liquid by introducing it into the liquid is disclosed.

JP-T-2006-508977

  However, in the purification method disclosed in Patent Document 1, a sublimation gas of an organic material is transported by an inert gas such as nitrogen, and the inert gas is used as a carrier gas. However, oxygen is contained in the inert gas. In some cases, it is mixed as an impurity at a concentration of several tens to several hundred ppm, and this oxygen may oxidize the organic material and affect the quality of the organic material. In addition, a small amount of oxygen may be mixed in the organic material to be purified, and this oxygen may also oxidize the organic material and affect the quality of the organic material.

  Therefore, the present invention is a method for purifying an organic compound such as an organic semiconductor that is required to have high purity, even if oxygen is mixed with an inert gas that is a carrier gas for transporting the vaporized organic compound. It is an object of the present invention to provide a purification method that prevents deterioration in quality of an organic compound or the like to be purified.

[1] That is, the present invention includes a vaporization step in which an organic compound placed in a vaporization chamber of a purification apparatus is heated and vaporized by a heating apparatus in a reduced pressure state;
A transport step in which the vaporized organic compound is transported from the vaporization chamber by an inert gas;
A precipitation step in which the organic compound conveyed by the conveyance step is precipitated,
In the organic compound deposition method, a reducing agent that reacts with oxygen present in the purification apparatus is present in the flow path of the inert gas.

  [2] A vaporization step in which an organic compound placed in the vaporization chamber is heated and vaporized by a heating device in a reduced pressure state, and a discharge unit in which the vaporized organic compound is protruded from the vaporization chamber In the vaporization chamber or in the ionic liquid, the process includes a transporting process transported by an inert gas, and a deposition process in which the organic compound is deposited from the ionic liquid in a deposition container filled with the ionic liquid that contacts the discharge unit. The organic compound precipitation method is characterized in that a reducing agent that reacts with oxygen present in is present in the vaporization chamber or in the ionic liquid.

  [3] The reducing agent is a gas, mixed with the inert gas, introduced into the vaporizing chamber, or mixed with the inert gas for the first time in the vaporizing chamber. Or it is the organic compound precipitation method as described in said [2].

  [4] The organic compound precipitation method according to [2], wherein the reducing agent is liquid or solid and is mixed in the ionic liquid.

  According to the present invention, even if oxygen is mixed with an inert gas or the like that is a carrier gas for transporting a vaporized organic compound, the quality of the organic compound or the like is deteriorated by reducing the oxygen with a reducing agent. Can be prevented.

It is a conceptual diagram which shows the organic compound precipitation apparatus of 1st embodiment of this invention. It is a conceptual diagram which shows the organic compound precipitation apparatus of 2nd embodiment of this invention. It is a conceptual diagram which shows the organic compound precipitation apparatus of 3rd embodiment of this invention.

  DESCRIPTION OF EMBODIMENTS Hereinafter, embodiments relating to an organic compound precipitation method according to the present invention will be described in detail with reference to the accompanying drawings. The embodiments described below are preferable specific examples for carrying out the present invention, and thus various technical limitations are made. However, the present invention is intended to limit the invention particularly in the following description. Unless specifically stated, the present invention is not limited to this form. Further, the vertical vertical direction in the description is the horizontal direction in FIG. In addition, the description showing a numerical range includes an upper limit and a lower limit.

  As shown in FIG. 1, the organic compound deposition apparatus E according to the first embodiment of the present invention is a vaporization that is a space surrounded by an upper lid 6, a lower lid 7, and a connecting member 8 that are heated by a heating device 2. The chamber 1, a discharge portion 3 protruding from the vaporization chamber 1, and a deposition container 4 filled with the ionic liquid IL in contact with the discharge portion 3 are provided.

  The vaporization chamber 1 is a space having a wall surface of a member heated by the heating device 2 and a placement portion 71 on which the organic compound OC is placed. In the first embodiment shown in FIG. 1, the vaporizing chamber 1 is a space formed by interposing an annular connecting member 8 between an upper lid 6 and a lower lid 7 having a cavity in the center. The upper lid 6, the lower lid 7 and the connecting member 8 are members heated by the heating device 2, and the boundary between the upper lid 6, the lower lid 7 and the connecting member 8 with the vaporizing chamber 1 corresponds to the wall surface of the vaporizing chamber 1.

  The upper lid 6, the lower lid 7, and the connecting member 8 are provided so as to be separable. The upper lid 6 is provided with a substantially cylindrical cavity at the center, and a through hole for connecting a gas supply pipe P1 for supplying gas supplied from the gas cylinder GB is provided on the upper surface thereof. The supplied gas can be sent to the central cavity. The lower lid 7 is provided with a cavity at the center thereof, and on the upper surface thereof, a placement portion 71 for placing the organic compound OC as a raw material is provided in an annular shape. In another embodiment, the mounting portion 71 is open to the vaporizing chamber 1 and can be a separate container from the lower lid 7 unless the central cavity leading to the discharge portion 3 is filled. . A hollow discharge part 3 is connected to the cavity at the center of the lower lid 7, and the organic compound OC that is a raw material vaporized in the vaporization chamber 1 can be sent to the discharge part 3 by gas from the gas cylinder GB. . The connecting member 8 is an annular member having a thickness in the vertical direction, and is connected to the upper lid 6 and the lower lid 7 so as to keep a constant distance between the lower surface side of the upper lid 6 and the upper surface side of the lower lid 7. Thus, the vaporizing chamber 1 having a predetermined size is formed. The upper lid 6, the lower lid 7, and the connecting member 8 are preferably made of a material excellent in heat conduction, and specifically, are preferably a metal such as stainless steel or copper, or an inorganic material such as glass. Although not shown, in order to maintain the airtightness of the vaporizing chamber 1, it is preferable that a gasket having heat resistance is provided at a connection portion such as the upper lid 6, the lower lid 7 and the connecting member 8.

  The heating device 2 is a member that heats the vaporization chamber 1 and the deposition container 4. In 1st embodiment, the heating apparatus 2 consists of an electrothermal member etc. by which temperature is separately controlled by the temperature control apparatus which is not shown in figure, and is embed | buried inside the heat retention part 5 which consists of heat insulation materials.

  Since the heating device 2 is provided so as to cover all or part of the upper lid 6, the lower lid 7 and the connecting member 8, the heating device 2 covers the entire vaporizing chamber 1. For this reason, when the organic compound OC which is the raw material in the vaporization chamber 1 is vaporized, it is deposited and fixed on the wall surface of the vaporization chamber 1 so as not to disturb the flow of the vaporized organic compound OC. A decrease in rate can be suppressed. The temperature control device 2 ′ is provided inside the heat retaining portion 5 made of a heat insulating material so as to cover the periphery of the precipitation vessel 4, and the ionic liquid filled in the precipitation vessel 4 through the precipitation vessel 4. Temperature adjustments can be made to heat or cool the IL. By heating or cooling the ionic liquid IL, it is possible to adjust the solubility of the vaporized organic compound OC dissolved in the ionic liquid IL, so that it is possible to control the saturation and precipitation rate of the organic compound OC, Depending on the type of organic compound to be purified, contamination with impurities can be minimized. The temperature adjusting device 2 ′ has only a function of performing only heating and can be provided integrally with the heating device 2.

  The discharge unit 3 is a member that protrudes from the vaporization chamber 1 and through which the vaporized organic compound OC passes. Since the discharge part 3 is hollow, the organic compound OC vaporized in the vaporization chamber 1 can pass through. In the first embodiment, the discharge part 3 has a substantially cylindrical base 32 connected to the lower lid 7 and a substantially cylindrical discharge port 31 on the deposition container 4 side and having a smaller diameter than the base 32. Further, it is provided in a straight line vertically downward from the vaporizing chamber 1. The vaporized organic compound OC is discharged from the discharge port 31 into the ionic liquid IL and dissolved, and then becomes supersaturated and reaches a dissolution equilibrium where dissolution and precipitation are repeated. In this way, the organic compound OC is precipitated as a single crystal or the like, and the amount of precipitation increases inside the precipitation vessel 4. Moreover, in 1st embodiment, although the discharge port 31 is embedded and is contacting ionic liquid IL, in other embodiment, the edge part of the discharge port 31 and the liquid level of ionic liquid IL are the same plane. In addition, a gap may be provided between the discharge port 31 and the liquid surface of the ionic liquid IL so as to be separated by a predetermined distance. When there is a gap between the discharge port 31 and the liquid surface of the ionic liquid IL, the vaporized organic compound OC is crystallized and deposited on the liquid surface of the ionic liquid IL or in the liquid.

  The discharge part 3 is preferably made of a material excellent in heat conduction, and specifically, is preferably a metal such as stainless steel or copper, or an inorganic material such as glass. Moreover, in other embodiment, the edge part which contacts the ionic liquid IL of the discharge port 31 can be made into a member whose heat conduction is lower than the base 32 side. As a result, even if the discharge unit 3 is heated by the heating device 2 via the lower lid 7, the temperature of the ionic liquid IL can be controlled more precisely because the heat is not easily transmitted to the ionic liquid IL.

  The deposition container 4 is a member attached to the lower part of the lower lid 7 and filled with the ionic liquid IL. In the first embodiment, the deposition container 4 is a vertically long container having an opening at the top, is filled with the ionic liquid IL, and the discharge port 31 of the discharge unit 3 is inserted therein. The deposition container 4 is preferably made of a material excellent in heat conduction, and specifically, is preferably a metal such as stainless steel or copper, or an inorganic material such as glass.

  The organic compound OC used in the present invention is an organic compound that sublimes from a solid to a gas, or an organic compound that evaporates from a liquid to a gas, and is an organic compound that can be vaporized by sublimation or evaporation. The organic compound OC is a raw material placed on the placement portion 71 of the vaporization chamber 1 by being vaporized by being heated in the vaporization chamber 1 and being precipitated in the ionic liquid IL filled in the deposition container 4. Impurities contained in the organic compound OC are removed and the purity thereof is increased. Thus, as the organic compound OC used for high purity, organic semiconductors used for organic EL, organic field effect transistors, organic solar cells, and the like are preferable. Specifically, examples of the organic semiconductor include pentacene, anthracene, rubrene, tetracyanoquinodimethane <TCNQ>, oligothiophene compound, phthalocyanine compound, perylene compound, tris (8-quinolinolato) aluminum <Alq3>, tetrathiafulvalene. <TTF>, tetrathiafulvalene compounds, N, N′-diphenyl-N, N′-bis (3-methylphenyl) -1,1′-biphenyl-4,4′-diamine, bis (10-hydroxybenzo) [H] Quinolinato) beryllium complex, 1,3-bis [5- (p-tert-butylphenyl) -3,4-oxadiazol-2-yl] benzene and the like are preferable.

  The ionic liquid IL used in the present invention is a salt present in a liquid at a room temperature of about 25 to 30 ° C. Since the ionic liquid IL is a nonvolatile organic solvent and does not evaporate even when heated under reduced pressure, the ionic liquid IL is very useful as a solvent for purifying the organic compound OC by recrystallization. Specifically, as the ionic liquid IL, 1-ethyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide <Emin / TFSI>, 1-butyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide < BMIM / TFSI>, 1-ethyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide <EMIM / TFSI>, 1-octyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide <OMIM / TFSI> 3-methyl-1-propylpyridinium bis (trifluoromethylsulfonyl) imide and the like are preferable. If the ionic liquid IL is not sufficiently deaerated prior to use, it is one of the causes for the ionic liquid IL to deteriorate over time due to an oxidation reaction by oxygen contained in the ionic liquid IL.

  The gas cylinder GB is a cylinder filled with an inert gas such as nitrogen or argon, and is supplied to the vaporization chamber 1 through a connected gas supply pipe P1. Then, the inert gas supplied to the vaporization chamber 1 passes through the discharge unit 3 together with the vaporized organic compound OC, and is discharged into the ionic liquid IL filled in the deposition container 4. Then, the inert gas released from the liquid surface of the ionic liquid IL is sucked into the vacuum pump VP through the through hole provided in the lower lid 7 and the gas discharge pipe P2. In this gas cylinder GB, oxygen may be mixed in the inert gas as an impurity at a concentration of several tens to several hundreds ppm. By sending this oxygen into the ionic liquid IL, the ionic liquid IL is oxidized by an oxidation reaction. This is one of the causes of deterioration.

  A hydrogen supply pipe P3 following the hydrogen cylinder HB filled with hydrogen as a reducing agent is connected midway between the gas cylinder GB and the upper surface of the upper lid 6 in the gas supply pipe P1. Hydrogen is supplied from the hydrogen cylinder HB while being adjusted using a flow rate measuring tool such as a flow meter (not shown) so as to be mixed with the inert gas from the gas cylinder GB at a specific flow rate ratio. Thus, since a gas mixture of an inert gas and hydrogen is supplied to the vaporization chamber 1, a small amount of oxygen that may be mixed in the gas cylinder GB or oxygen dissolved in the ionic liquid IL. The water reacts with the heat of the heating device 2 to generate water, and oxygen contained in a trace amount in the vaporizing chamber 1, the discharge unit 3, and the ionic liquid IL is removed. For this reason, since the oxidation reaction due to oxygen does not occur, the yield of the organic compound to be purified can be improved, and the ionic liquid IL is hardly changed over time, and the deterioration of the quality thereof can be prevented. it can. Furthermore, since the gas cylinder GB having a high purity of the inert gas is expensive, an inexpensive gas cylinder GB mixed with a little oxygen can be used, and the cost can be reduced. Further, in order to improve the reaction efficiency between hydrogen and oxygen, a metal such as nickel, copper-chromium oxide, ruthenium, rhodium, palladium, platinum or the like is used as a catalyst at a position in contact with the ionic liquid IL in the vaporizing chamber 1 or the deposition vessel 4. In order to avoid the catalyst from affecting the decomposition of the vaporized organic compound OC or the like, the catalyst is placed on the upper lid 6 side in the vaporization chamber 1 upstream of the vaporized organic compound OC. It is preferable to keep it.

  In this embodiment, gaseous hydrogen is used as a reducing agent for reducing oxygen present in the system such as the vaporization chamber 1, the discharge unit 3, and the ionic liquid IL, but the powder is a solid, powder or particulate. Or a liquid reducing agent that reduces oxygen can be used. When solid iron is used, it reacts with oxygen to become iron oxide to reduce oxygen, and can be separated from the precipitated organic compound OC, and can be easily removed from the system.

  FIG. 2 shows a second embodiment of the present invention. In the first embodiment shown in FIG. 1, the hydrogen that is a gaseous reducing agent is designed to be combined with an inert gas and sent to the vaporizing chamber 1 through the gas supply pipe P <b> 1 connected from the gas cylinder GB to the vaporizing chamber 1. . However, in the first embodiment, when the arrangement of the apparatus E and the hydrogen cylinder HB is restricted, hydrogen as a gaseous reducing agent is sent directly to the vaporization chamber 1 independently of the inert gas from the gas cylinder GB. It is a device.

  Specifically, except for the hydrogen cylinder HB and the hydrogen supply pipe P3 following the hydrogen cylinder HB, the configuration is substantially the same as in the first embodiment, and the gas supplied from the gas cylinder GB is provided on the upper surface of the upper lid 6. In addition to the through hole for connecting the gas supply pipe P1 for supplying hydrogen, another through hole for connecting the hydrogen supply pipe P3 connected to the hydrogen cylinder HB is provided and supplied from the gas cylinder GB. Hydrogen gas as well as inert gas can be sent to the cavity at the center of the vaporizing chamber 1. Then, the hydrogen from the hydrogen cylinder HB is adjusted and supplied using a flow rate measuring tool such as a flow meter (not shown) so as to be mixed with the inert gas from the gas cylinder GB at a specific flow rate ratio. Thus, as in the first embodiment, since the gas mixture of the inert gas and hydrogen is supplied to the vaporizing chamber 1, a small amount of oxygen or ions that may be mixed in the gas cylinder GB. Oxygen dissolved in the liquid IL reacts with heat from the heating device 2 to generate water, and oxygen contained in a trace amount in the vaporizing chamber 1, the discharge unit 3 and the ionic liquid IL is removed. For this reason, since the oxidation reaction due to oxygen does not occur, the yield of the organic compound to be purified can be improved, and the ionic liquid IL is hardly changed over time, and the deterioration of the quality thereof can be prevented. it can.

  FIG. 3 shows a third embodiment of the present invention. Unlike the first embodiment shown in FIG. 1 and the second embodiment shown in FIG. 2, it is designed to use a solid reducing agent without using a gaseous reducing agent such as hydrogen gas.

  Specifically, except for the hydrogen cylinder HB and the hydrogen supply pipe P3 following the hydrogen cylinder HB, it has substantially the same configuration as that of the first embodiment, and is in contact with the ionic liquid IL inside the deposition vessel 4 In addition, particulate iron SR, which is a solid reducing agent housed in a mesh-like container that communicates inside and outside, is housed and dissolved in a small amount of oxygen or ionic liquid IL that may be mixed in the gas cylinder GB. The oxygen reacts with the heat of the heating device 2 ′ and iron oxide is generated, and the oxygen contained in a trace amount in the vaporizing chamber 1, the discharge part 3, and the ionic liquid IL is removed. For this reason, since the oxidation reaction due to oxygen does not occur, the yield of the organic compound to be purified can be improved, and the ionic liquid IL is hardly changed over time, and the deterioration of the quality thereof can be prevented. it can.

  And the organic compound precipitation method in embodiment of this invention has vaporization process S1, conveyance process S2, and precipitation process S3, and demonstrates it below.

The vaporization step S <b> 1 is a step in which the organic compound OC placed in the vaporization chamber 1 is heated and vaporized in a reduced pressure state by the heating device 2 that covers the vaporization chamber 1. In the first to third embodiments, the vaporization chamber 1 is decompressed by the vacuum pump VP, and the vaporization chamber 1 is heated by heating the upper lid 6, the lower lid 7 and the connecting member 8 by the heating device 2. The organic compound OC, which is a raw material placed on the placement unit 71, is vaporized by sublimation or evaporation. Since the inert gas appropriately flows into the vaporizing chamber 1 from the gas cylinder GB, the degree of vacuum in the vaporizing chamber 1 is preferably adjusted to 10 ⁻³ to 10 ⁻¹ Torr. Further, in the first embodiment and the second embodiment, the degree of vacuum of the vaporizing chamber 1 is 10 based on hydrogen as a reducing agent that is further introduced into the vaporizing chamber 1 and reduces oxygen in the system from the hydrogen cylinder HB. It is preferably adjusted to ^-3 to 10 ^-1 Torr. When the degree of vacuum of the vaporizing chamber 1 is within this range, the upper lid 6, the lower lid 7, the connecting member 8 and the like can be heated within a range that can be withstood, and a sufficient amount of the vaporized organic compound OC can be conveyed. An inert gas or the like can be introduced into the vaporizing chamber 1. The degree of vacuum in the vaporizing chamber 1 can be measured by connecting a pressure gauge (not shown) to the vaporizing chamber 1 or the like.

  The transport process S2 is a process in which the vaporized organic compound OC is transported by an inert gas from the vaporization chamber 1 to the discharge unit 3 protruding. In the first embodiment and the second embodiment, the hydrogen supplied from the hydrogen cylinder HB is also confused with the inert gas and transports the vaporized organic compound OC. In the present embodiment, the inert gas or the like that has flowed into the vaporization chamber 1 from the upper part of the vaporization chamber 1 entrains the vaporized organic compound OC toward the discharge port 31 of the discharge unit 3 attached to the lower lid 7. The vaporized organic compound OC is conveyed to the discharge port 31 of the discharge unit 3 by flowing in a straight line from the upper side to the lower side in the vertical direction. In the first embodiment and the second embodiment, in particular, the inert gas and the hydrogen gas flow in a straight line from the vaporization chamber 1 to the ionic liquid IL. It is possible to transport the organic compound OC vaporized in the surroundings to the ionic liquid IL without stagnation in the discharge unit 3 while entraining the organic compound OC evenly.

  The deposition step S3 is a step in which the organic compound OC is deposited from the ionic liquid IL in the deposition container 4 that is filled with the ionic liquid IL that the discharge unit 3 contacts. That is, the vaporized organic compound OC is dissolved in the ionic liquid IL, and is in a supersaturated state, reaching a dissolution equilibrium where repeated dissolution and precipitation occur. In this way, the organic compound OC is precipitated as a single crystal or the like, and the amount of precipitation increases inside the precipitation vessel 4. Thereby, it is easy to grow a single crystal and the degree of purification can be improved. The vaporized organic compound OC transported into the ionic liquid IL through the discharge unit 3 by an inert gas or the like is initially dissolved in the ionic liquid IL, but the vaporized organic compound OC is continuously in the ionic liquid IL. Therefore, the organic compound OC that cannot be completely dissolved in the ionic liquid IL when the dissolution reaches saturation is deposited in the deposition container 4 in the form of a single crystal or the like. In addition, the organic compound OC can be preliminarily dissolved in the ionic liquid IL to a saturated or nearly saturated state, and the organic compound OC can be deposited as soon as the vaporized organic compound OC is transported into the ionic liquid IL. . It should be noted that by adjusting the temperature by heating or cooling the ionic liquid IL by the temperature adjusting device 2 ′ around the precipitation container 4, the solubility of the organic compound OC, the precipitation rate, etc. are controlled to minimize impurities. Crystals can be precipitated.

DESCRIPTION OF SYMBOLS 1 ... Vaporization chamber 2 ... Heating device 2 '... Temperature control device 3 ... Discharge part 31 ... Discharge port 32 ... Base part 4 ... Deposition container 5 ... Insulation part 6 ... Upper lid 7 ··· Lower lid 71 ··· Placement portion 8 ··· Connection member E ··· Organic compound precipitation device (purification device)
OC ・ ・ Organic compound IL ・ ・ Ion liquid VP ・ ・ Vacuum pump GB ・ ・ Gas cylinder HB ・ ・ Hydrogen cylinder P1 ・ ・ Gas supply pipe P2 ・ ・ Gas discharge pipe

Claims (4)

A vaporization step in which the organic compound placed in the vaporization chamber of the purification apparatus is heated and vaporized in a reduced pressure state by a heating apparatus;
A transport step in which the vaporized organic compound is transported from the vaporization chamber by an inert gas;
A precipitation step in which the organic compound conveyed by the conveyance step is precipitated,
An organic compound deposition method, wherein a reducing agent that reacts with oxygen present in the purification apparatus is present in the flow path of the inert gas. A vaporization step in which the organic compound placed in the vaporization chamber is heated and vaporized in a reduced pressure state by a heating device;
A transporting process in which the vaporized organic compound is transported by an inert gas to a discharge portion protruding from the vaporizing chamber;
A precipitation step in which the organic compound is precipitated from the ionic liquid in a precipitation container filled with the ionic liquid in contact with the discharge part,
An organic compound precipitation method, wherein a reducing agent that reacts with oxygen present in the vaporization chamber or the ionic liquid is present in the vaporization chamber or the ionic liquid.   The said reducing agent is gas, is mixed with the said inert gas, is introduced into the said vaporization chamber, or is mixed with an inert gas for the first time in the said vaporization chamber, The Claim 1 or Claim 2 characterized by the above-mentioned. The organic compound precipitation method.   The organic compound precipitation method according to claim 2, wherein the reducing agent is liquid or solid and is mixed in the ionic liquid.

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