Composition for heat transfer fluid, heat transfer fluid, heat transfer device, and heat transfer method

Abstract

Provided is a composition for a heat transfer fluid, the composition containing perfluorotripropylamine and a hexafluoropropene trimer represented by C9F18.

Description

HEAT TRANSFER FLUID COMPOSITION, HEAT TRANSFER FLUID, HEAT TRANSFER DEVICE, AND HEAT TRANSFER METHOD

[0001] FIELD OF THE DISCLOSURE The present disclosure relates to heat transfer fluid compositions, heat transfer fluids, heat transfer devices, and heat transfer methods.

[0002] It is known to use a trimer of hexafluoropropene (HFP) as a heat transfer fluid (Patent Document 1).

[0003] The trimer of HFP has a low global warming potential (GWP) and low toxicity, and is therefore attracting attention as a substitute for chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs).

[0004] Special Publication No. 2020-514420

[0005] Hexafluoropropene trimer has a low GWP, but has a low boiling point, making it difficult to use at high temperatures.

[0006] It is an object of the present invention to provide a heat transfer fluid that is suitable for use at relatively high temperatures.

[0007] The present disclosure includes the following aspects: [1] C ９ F １８ [2] A heat transfer fluid composition comprising a hexafluoropropene trimer represented by the following formulas (I) to (III): and perfluorotripropylamine. [3] The heat transfer fluid composition according to the above [1], which contains at least one hexafluoropropene trimer represented by the formula: ９ F １８The heat transfer fluid composition according to the above [1] or [2], wherein the mass ratio of the hexafluoropropene trimer represented by the formula (I) to perfluorotripropylamine is 0.1:99.9-99.9-0.1. [4] The heat transfer fluid composition according to the above [2] or [3], wherein the compound represented by formula (I) is contained in an amount of less than 85 mass% based on the total amount of the compounds represented by formulas (I) to (III). [5] The heat transfer fluid composition according to the above [2] or [3], wherein the compound represented by formula (I) is contained in an amount of 50 mass% or more but less than 85 mass% based on the total amount of the compounds represented by formulas (I) to (III). [6] The heat transfer fluid composition according to the above [2] or [3], wherein the compound represented by formula (I) is contained in an amount of 85 mass% or more based on the total amount of the hexafluoropropene trimer. [7] The heat transfer fluid composition according to the above [2] or [3], wherein the compound represented by formula (I) is contained in an amount of 85 mass% or more based on the total amount of the hexafluoropropene trimer. ９ F １８and perfluorotripropylamine is 80 mass % or more in the heat transfer fluid composition. [8] The heat transfer fluid composition according to any one of [1] to [7] above, which is a pseudo-azeotropic liquid. [9] The heat transfer fluid composition according to any one of [1] to [8] above, which is used in a semiconductor manufacturing process.

[10] A heat transfer fluid comprising the heat transfer fluid composition according to any one of [1] to [9] above.

[11] The heat transfer fluid according to

[10] above, which further comprises a stabilizer.

[12] The heat transfer fluid according to

[10] or

[11] above, which is used in a semiconductor manufacturing process.

[13] Use of the heat transfer fluid composition according to any one of [1] to [9] above, or the heat transfer fluid according to any one of

[10] to

[12] above, for heat transfer.

[14] A heat transfer apparatus comprising: a device; and a mechanism for transferring heat to or from the device, the mechanism comprising the heat transfer fluid composition according to any one of [1] to [9] above, or the heat transfer fluid according to any one of

[10] to

[12] above.

[15] The heat transfer apparatus according to

[14] above, wherein the device is a wafer used for manufacturing semiconductors.

[16] A semiconductor manufacturing apparatus comprising the heat transfer apparatus according to

[14] or

[15] above.

[17] A heat transfer method comprising: preparing a device; and transferring heat to or from the device using the heat transfer fluid composition according to any one of [1] to [9] above, or the heat transfer fluid according to any one of

[10] to

[12] above.

[18] The heat transfer method according to

[17] above, wherein the device is a wafer used for manufacturing semiconductors.

[0008] The present disclosure provides a heat transfer fluid suitable for use at relatively high temperatures.

[0009] Figure 1 shows the results of a simulation of the vapor-liquid equilibrium of a mixture of the compound represented by formula (I) and perfluorotripropylamine. Figure 2 shows the results of a simulation of the vapor-liquid equilibrium of a mixture of the compound represented by formula (II) and perfluorotripropylamine. Figure 3 shows the results of a simulation of the vapor-liquid equilibrium of a mixture of the compound represented by formula (III) and perfluorotripropylamine.

[0010] When referred to in this specification, the numerical range "A to B" is intended to include the lower and upper limit numerical values ​​themselves. In other words, the numerical range "A to B" means A or more and B or less.

[0011] The heat transfer fluid composition of the present disclosure will now be described.

[0012] (Heat Transfer Fluid Composition) The heat transfer fluid composition of the present disclosure is ９ F １８ and perfluorotripropylamine.

[0013] C ９ F １８ Hexafluoropropene trimer represented by the formula (I) has a low pour point and a low kinematic viscosity at low temperatures, making it suitable for use at low temperatures, but its low boiling point makes it difficult to use at high temperatures. On the other hand, perfluorotripropylamine has a high boiling point and is suitable for use at high temperatures, but its high pour point and high kinematic viscosity at low temperatures make it difficult to use at low temperatures. The heat transfer fluid composition of the present disclosure has a low GWP and an excellent balance between boiling point and kinematic viscosity. In addition, the heat transfer fluid composition of the present disclosure can have excellent stability. Furthermore, the heat transfer fluid composition of the present disclosure exhibits pseudoazeotropy, making it easy to handle and maintain.

[0014] C ９ F １８ The hexafluoropropene trimer represented by the formula (I) is not particularly limited, and examples thereof include C ９ F １８ The compound may have any structure represented by the following formula:

[0015] In a preferred embodiment, the hexafluoropropene trimer is represented by the following formulas (I) to (III): The hexafluoropropene trimer contains at least one hexafluoropropene trimer represented by the formula:

[0016] In this specification, unless otherwise specified, the compound represented by the above formula (I) includes both E and Z diastereomers.

[0017] The hexafluoropropene trimer contained in the heat transfer fluid composition of the present disclosure may contain only one of the compounds represented by formulas (I) to (III), or may be a mixture containing two or three of these compounds.

[0018] In the heat transfer fluid composition of the present disclosure, the compound represented by Formula (I) may be contained in an amount of 99% by mass or less, preferably 90% by mass or less, more preferably 85% by mass or less, even more preferably less than 85% by mass, and even more preferably 80% by mass or less, for example, 75% by mass or less, 70% by mass or less, 65% by mass or less, or 60% by mass or less, based on the total amount of the compounds represented by Formulas (I) to (III). Reducing the content of the compound represented by Formula (I) increases the boiling point of the heat transfer fluid composition. In other words, the vapor pressure of the heat transfer fluid composition decreases. Higher vapor pressure of the heat transfer fluid composition makes it more susceptible to vaporization, which can increase leakage from the equipment, for example, when used in semiconductor manufacturing equipment. The low vapor pressure of the heat transfer fluid composition of the present disclosure reduces leakage from the equipment, providing environmental and economic advantages.

[0019] In the heat transfer fluid composition of the present disclosure, the compound represented by formula (I) may be contained in an amount of preferably 1% by mass or more, preferably 10% by mass or more, more preferably 30% by mass or more, even more preferably 45% by mass or more, particularly preferably 50% by mass or more, for example, 60% by mass or more, 65% by mass or more, 75% by mass or more, or 85% by mass or more, based on the total amount of the compounds represented by formulas (I) to (III). Increasing the content of the compound represented by formula (I) reduces the kinematic viscosity, and when used in, for example, semiconductor manufacturing equipment, the pressure required to circulate the heat transfer fluid composition can be reduced. Reducing the pressure required to circulate the heat transfer fluid composition can reduce pressure loss and leakage from the equipment, thereby lowering operating costs.

[0020] In the heat transfer fluid composition of the present disclosure, the compound represented by formula (I) is contained in an amount of, for example, 1% by mass or more and 99% by mass or less, 10% by mass or more and 90% by mass or less, 30% by mass or more and 90% by mass or less, 10% by mass or more and 85% by mass or less, 35% by mass or more and 85% by mass or less, 10% by mass or more and less than 85% by mass, 20% by mass or more and less than 85% by mass, 30% by mass or more and less than 85% by mass, 40% by mass or more and less than 85% by mass, 50% by mass or more and less than 85% by mass, It may be 40% by mass or more and 80% by mass or less, 55% by mass or more and 80% by mass or less, 60% by mass or more and 75% by mass or less, 65% by mass or more and 70% by mass or less, 35% by mass or more and 60% by mass or less, or 50% by mass or more and 60% by mass or less, preferably 30% by mass or more and 90% by mass or less, preferably 40% by mass or more and less than 85% by mass, more preferably 40% by mass or more and 80% by mass or less, even more preferably 45% by mass or more and 70% by mass or less, and even more preferably 50% by mass or more and 60% by mass or less.

[0021] In the heat transfer fluid composition of the present disclosure, the mass ratio of the compound represented by formula (II) to the compound represented by formula (III) is not particularly limited, and may be, for example, 1:9 to 9:1, 2:8 to 8:2, 3:7 to 7:3, 4:6 to 6:4, or 4.5:5.5 to 5.5:4.5.

[0022] The compounds represented by formulas (I) to (III) can be produced by conventional methods, for example, but not limited to, the method described in WO 2018 / 172919. Alternatively, they can be obtained by trimerization of hexafluoropropene as a raw material by conventional methods.

[0023] In the heat transfer fluid composition of the present disclosure, ９ F １８ The mass ratio of the hexafluoropropene trimer represented by the formula (I) to perfluorotripropylamine is preferably 0.1:99.9 to 99.9:0.1, more preferably 1:99 to 99:1, and even more preferably 5:95 to 95:5, for example, 10:90 to 90:10, 20:80 to 80:20, 30:70 to 70:30, 40:60 to 60:40, or 45:55 to 55:45.

[0024] C ９ F １８ The total amount of the hexafluoropropene trimer represented by the formula C and perfluorotripropylamine in the heat transfer fluid composition may be preferably 80% by mass or more, more preferably 85% by mass or more, and even more preferably 90% by mass or more, for example, 95% by mass or more, 98% by mass or more, 99% by mass or more, or 99.9% by mass or more. ９ F １８ The total amount of the hexafluoropropene trimer represented by the formula (I) and perfluorotripropylamine may be substantially 100% by mass in the heat transfer fluid composition. In other words, the heat transfer fluid of the present disclosure is ９ F １８ and perfluorotripropylamine.

[0025] The heat transfer fluid composition of the present disclosure may be a near-azeotropic liquid. When the heat transfer fluid composition is a near-azeotropic liquid, even when the heat transfer fluid composition vaporizes, the change in composition is small, making the heat transfer fluid composition easy to handle.

[0026] Here, the term "quasi-azeotropic liquid" refers to a liquid in which the difference in molar fraction between the vapor phase and the liquid phase of each component contained in the quasi-azeotropic liquid is within 10%.

[0027] The heat transfer fluid composition of the present disclosure can be obtained by mixing hexafluoropropene trimer and perfluorotripropylamine in a predetermined ratio. The heat transfer fluid composition of the present disclosure may be in a form in which the compound represented by hexafluoropropene trimer and perfluorotripropylamine are mixed in advance, or in a form in which the two are mixed immediately before use.

[0028] The heat transfer fluid composition of the present disclosure may further comprise any of the compounds represented by formulas (I) to (III) other than C ９ F １８ The hexafluoropropene may contain a hexafluoropropene trimer represented by the following formula:

[0029] The heat transfer fluid compositions of the present disclosure may include hexafluoropropene dimer.

[0030] The hexafluoropropene dimer may include (E)-1,1,1,2,3,4,5,5,5-nonafluoro-4-(trifluoromethyl)-2-pentene, (Z)-1,1,1,2,3,4,5,5,5-nonafluoro-4-(trifluoromethyl)-2-pentene, or 1,1,3,4,4,5,5-nonafluoro-2-(trifluoromethyl)-2-pentene.

[0031] The heat transfer fluid composition of the present disclosure may include hexafluoropropene tetramer.

[0032] The hexafluoropropene tetramer may include 1,1,1,2,5,6,6,6-octafluoro-2,3,5-tris(trifluoromethyl)-4-(perfluoropropyl-2-yl)-3-hexene.

[0033] The heat transfer fluid composition of the present disclosure contains, in addition to the hexafluoropropene trimer, C ｍ F ２ｍ and / or C ｎ F （２ｎ－２） [wherein m is an integer of 4 or more and 12 or less except 9, and n is an integer of 4 or more and 12 or less].

[0034] m is an integer of 4 or greater, preferably an integer of 5 or greater, and more preferably an integer of 6 or greater. Furthermore, n is an integer of 12 or less, preferably an integer of 11 or less, and more preferably an integer of 10 or less, provided that m does not include 9.

[0035] n is an integer of 4 or greater, preferably an integer of 5 or greater, and more preferably an integer of 6 or greater. Furthermore, n is an integer of 12 or less, preferably an integer of 11 or less, and more preferably an integer of 10 or less. Furthermore, n is particularly preferably 9.

[0036] C ｍ F ２ｍ may be a chain compound or a cyclic compound which may have a substituted structure. The chain compound may be a so-called alkene, and may be linear or branched.

[0037] C ｎ F （２ｎ－２） may be a chain compound or a cyclic compound which may have a substituted structure. The chain compound may be a diene or an alkyne, and may be linear or branched.

[0038] In the heat transfer fluid composition of the present disclosure, ｍ F ２ｍ and / or C ｎ F （２ｎ－２） The coexistence of C with hexafluoropropene trimer improves the function of the heat transfer fluid composition. ｍ F ２ｍ and / or C ｎ F （２ｎ－２） By including the compound (I), the stability of the hexafluoropropene trimer is improved.

[0039] C ｍ F ２ｍ and / or C ｎ F （２ｎ－２） The content of C in the heat transfer fluid composition of the present disclosure may be preferably 10% by mass or less, more preferably 5% by mass or less, and even more preferably 1% by mass or less. ｍ F ２ｍ and / or Cｎ F （２ｎ－２） The content of C in the heat transfer fluid composition of the present disclosure may be preferably 0.0001% by mass or more, more preferably 0.001% by mass or more. ｍ F ２ｍ and / or C ｎ F （２ｎ－２） is not an essential component in the heat transfer fluid composition of the present disclosure and may not be included.

[0040] The heat transfer fluid composition of the present disclosure may further include perfluoropolyether, a methoxytridecafluoroheptene isomer mixture, perfluorotributylamine, and the like.

[0041] The perfluoropolyether preferably has the general formula: RO-Rf １ -R', wherein R and R' are the same or different and are represented by -C ｍ F ２ｍ＋１ where m is an integer of 1 to 8, and Rf １ is a divalent fluoropolyoxyalkylene group containing 2 to 20 repeating units, said repeating units being: (i) -CFXO-, where X is F or CF ３ (ii) -CF ２ CFXO- (wherein X is F or CF ３ (iii) -CFXCF ２ O— (wherein X is F or CF ３ (iv) -CF ２ CF ２ CF ２ O-; or (v) -CF ２ CF ２ CF ２ CF ２ O-, or Rf １ (vi) -(CF ２ ) ｎ -CFY-O- (wherein n is an integer of 0 to 3, and Y is a group represented by the general formula -ORf ２ A monovalent group represented by Z, wherein Rf ２ is -CFXO-, -CF ２ CFXO-, -CF ２CF ２ CF ２ O- or -CF ２ CF ２ CF ２ CF ２ A divalent fluoropolyoxyalkylene group containing 2 to 20 repeating units represented by O—, where each X is the same or different and is F or CF ３ and Z is a monovalent C １－５ is a divalent group represented by the formula (a perfluoroalkyl group).

[0042] Specific examples of perfluoropolyethers include those with the product names GALDEN (registered trademark) "HT135" and GALDEN (registered trademark) "HT110" (both manufactured by Solvay).

[0043] The methoxytridecafluoroheptene isomer mixture is specifically methyl-perfluoroheptene ether (MPHE) (C ７ F １３ OCH ３ ) Specifically, a product name "Opteon SF10" (manufactured by Chemours) can be mentioned.

[0044] When the heat transfer fluid composition of the present disclosure contains perfluoropolyether and a methoxytridecafluoroheptene isomer mixture, these and C ９ F １８ Since the properties as a heat transfer fluid are similar to those of the compound represented by the formula (I), the properties as a heat transfer fluid of the entire heat transfer fluid composition are basically unchanged regardless of the content ratio of these compounds. ９ F １８ The compound represented by the formula (I) is preferably contained in an amount of 40% by mass to 99.9% by mass, more preferably 60% by mass to 99.9% by mass, and even more preferably 80% by mass to 99.9% by mass.

[0045] The heat transfer fluid composition of the present disclosure may further contain water. The content of water in the heat transfer fluid composition is 1 ppm by mass or more, and preferably 5 ppm by mass or more. By setting the water content to a certain level or more, for example 1 ppm by mass or more, it is possible to suppress charging of the composition due to a decrease in the stability of the heat transfer fluid composition. Furthermore, the content of water in the heat transfer fluid composition is 1000 ppm by mass or less, preferably 500 ppm by mass or less, more preferably 100 ppm by mass or less, and even more preferably 20 ppm by mass or less. By setting the water content to a certain level or less, for example 1000 ppm by mass or less, it is possible to reduce C during heating. ９ F １８ This can suppress the decomposition of the HFP trimer represented by the formula (I), and thus can suppress the increase in fluoride ions and the increase in acidity.

[0046] In one embodiment, the water content is C ９ F １８ The amount is preferably 0.0001 part by mass or more, more preferably 0.0005 part by mass or more, and even more preferably 0.001 part by mass or more, relative to 100 parts by mass of the total of the compounds represented by the formula:

[0047] On the other hand, the water content is ９ F １８ The amount is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and even more preferably 1 part by mass or less, relative to 100 parts by mass of the total of the compounds represented by the formula:

[0048] The heat transfer fluid composition of the present disclosure may further contain fluoride ions. The amount of fluoride ions in the heat transfer fluid composition is preferably 0.000001 mass% or more, and more preferably 0.00001 mass% or more, based on the total mass of the heat transfer fluid composition.

[0049] Furthermore, the amount of fluoride ions contained in the heat transfer fluid composition of the present disclosure is preferably 5 mass % or less, more preferably 1 mass % or less, even more preferably 0.1 mass % or less, particularly preferably 0.01 mass % or less, and even more particularly preferably 0.001 mass % or less, based on the total amount of the heat transfer fluid composition.

[0050] As the fluoride ion, a wide variety of known fluoride ions can be used, and there is no particular limitation.Specific examples include hydrogen fluoride, sodium fluoride, sodium hydrogen fluoride, potassium fluoride, potassium hydrogen fluoride, lithium fluoride, cesium fluoride, calcium fluoride, magnesium fluoride, aluminum fluoride, zinc fluoride, silver fluoride, and iron fluoride.Only one of these may be contained, or multiple types may be contained.

[0051] The kinematic viscosity at −50° C. of the heat transfer fluid composition of the present disclosure may be preferably 20.0 cSt or less, more preferably 16.0 cSt or less, even more preferably 12.0 cSt or less, still more preferably 11.0 cSt or less, and particularly preferably 10.0 cSt. The kinematic viscosity at −50° C. of the heat transfer fluid composition of the present disclosure may be 1.0 cSt or more, for example, 5.0 cSt or more, or 8.0 cSt or more.

[0052] The kinematic viscosity at −50° C. of the heat transfer fluid composition of the present disclosure can be measured using an Ubbelohde viscometer in accordance with JIS K 2283.

[0053] The boiling point of the heat transfer fluid composition of the present disclosure may be preferably above 110° C., more preferably 112° C. or higher, even more preferably 113° C. or higher, still more preferably 115° C. or higher, particularly preferably 118° C. or higher, and especially preferably 120° C. or higher. The boiling point of the heat transfer fluid composition of the present disclosure may be, for example, 125° C. or lower.

[0054] (Heat Transfer Fluid) The heat transfer fluid of the present disclosure may contain other components in addition to the heat transfer fluid composition of the present disclosure. In one embodiment, the heat transfer fluid composition itself may be the heat transfer fluid. In another embodiment, the heat transfer fluid composition includes other components.

[0055] The heat transfer fluid of the present disclosure may contain any components other than the heat transfer fluid composition that do not impair the effects and purposes of the present disclosure. Examples of such components include water, stabilizers, etc.

[0056] The stabilizer functions as a so-called acid acceptor or antioxidant by exhibiting a stabilizing effect, which mainly includes an effect of preventing decomposition of the hexafluoropropene trimer by capturing radicals generated in the system, and an acid-accepting effect of preventing further decomposition of the hexafluoropropene trimer by the acid by capturing the acid generated in the system.

[0057] As the stabilizer, a wide variety of known stabilizers can be used, but among them, it is preferable to use one or more stabilizers selected from the group consisting of unsaturated alcohol-based stabilizers, nitro-based stabilizers, amine-based stabilizers, phenol-based stabilizers, and epoxy-based stabilizers, because they can effectively suppress the occurrence of metal corrosion due to the composition.

[0058] A wide variety of known unsaturated alcohol stabilizers can be used, including, for example, one or more selected from the group consisting of 3-buten-2-ol, 2-buten-1-ol, 4-propen-1-ol, 1-propen-3-ol, 2-methyl-3-buten-2-ol, 3-methyl-3-buten-2-ol, 3-methyl-2-buten-1-ol, 2-hexen-1-ol, 2,4-hexadien-1-ol, and oleyl alcohol.

[0059] A wide variety of known nitro stabilizers can be used. Examples of aliphatic nitro compounds include nitromethane, nitroethane, 1-nitropropane, and 2-nitropropane. Examples of aromatic nitro compounds that can be used include one or more selected from the group consisting of nitrobenzene, o-, m-, or p-dinitrobenzene, o-, m-, or p-nitrotoluene, dimethylnitrobenzene, m-nitroacetophenone, o-, m-, or p-nitrophenol, o-nitroanisole, m-nitroanisole, and p-nitroanisole.

[0060] A wide variety of known amine stabilizers can be used as the amine stabilizer. For example, one or more selected from the group consisting of pentylamine, hexylamine, diisopropylamine, diisobutylamine, di-n-propylamine, diallylamine, triethylamine, N-methylaniline, pyridine, morpholine, N-methylmorpholine, triallylamine, allylamine, α-methylbenzylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, propylamine, isopropylamine, dipropylamine, tripropylamine, butylamine, isobutylamine, dibutylamine, tributylamine, dipentylamine, tribenzylamine, 2-ethylhexylamine, aniline, N,N-dimethylaniline, N,N-diethylaniline, ethylenediamine, propylenediamine, diethylenetriamine, tetraethylenepentamine, benzylamine, dibenzylamine, diphenylamine, and diethylhydroxylamine can be used.

[0061] A wide variety of known phenolic stabilizers can be used, including, for example, one or more selected from the group consisting of 2,6-ditertiarybutyl-4-methylphenol, 3-cresol, phenol, 1,2-benzenediol, 2-isopropyl-5-methylphenol, and 2-methoxyphenol.

[0062] A wide variety of known epoxy stabilizers can be used, including, for example, one or more selected from the group consisting of butylene oxide, 1,2-propylene oxide, 1,2-butylene oxide, butyl glycidyl ether, diethylene glycol diglycidyl ether, and 1,2-epoxy-3-phenoxypropane.

[0063] The combination of stabilizers having different stabilizing effects more effectively prevents decomposition of the hexafluoropropene trimer, which may occur for various reasons. For this reason, the stabilizer is preferably one or more selected from the group consisting of the above-mentioned epoxy-based stabilizer, as well as unsaturated alcohol-based stabilizers, nitro-based stabilizers, and phenol-based stabilizers.

[0064] From the viewpoint of effectively suppressing acid liberation from the hexafluoropropene trimer and suppressing metal corrosion by the liquid composition, the content of the stabilizer in the entire heat transfer fluid is preferably 0.0001% by mass or more, more preferably 0.01% by mass or more. On the other hand, in consideration of avoiding undesirable changes in the physical properties of the heat transfer fluid due to excessive addition of the stabilizer, the content of the stabilizer in the entire heat transfer fluid is preferably 10% by mass or less, more preferably 5% by mass or less.

[0065] (Use of Heat Transfer Fluid Composition or Heat Transfer Fluid) The heat transfer fluid composition and heat transfer fluid of the present disclosure are used to remove heat from or supply heat to various heat-transfer-receiving objects. Heat-transfer-receiving objects in the present disclosure include articles, devices, and atmospheres that are cooled, heated, or maintained at a controlled temperature. Examples of such heat-transfer-receiving objects include electrical components, mechanical components, and optical components, as well as processed products and assemblies thereof. Specific examples of heat-transfer-receiving objects in the present disclosure include, but are not limited to, wafers used in manufacturing semiconductor devices, microprocessors, power control semiconductors, electrical branch switches, power transformers, circuit boards, multi-chip modules, mounted and unmounted semiconductor devices, chemical reactors, nuclear reactors, fuel cells, lasers, and missile components.

[0066] The heat transfer fluid composition or heat transfer fluid of the present disclosure has low pressure loss during circulation during use, and is therefore suitable for use in applications requiring large amounts of heat transfer. In a preferred embodiment, the heat transfer fluid composition or heat transfer fluid of the present disclosure is used in a semiconductor manufacturing process. The object to which heat is transferred in the semiconductor manufacturing process is a wafer used to manufacture a semiconductor device.

[0067] The heat transfer fluid composition or heat transfer fluid of the present disclosure can also be used as a two-phase immersion cooling, chiller fluid, or Rankine cycle working fluid.

[0068] The heat transfer fluid composition or heat transfer fluid of the present disclosure can be used in place of the heat transfer fluid currently used in equipment designed to use them to transfer heat.

[0069] The heat transfer fluid composition or heat transfer fluid of the present disclosure can be a drop-in replacement, a near drop-in replacement, or a retrofit replacement for heat transfer fluids currently in use. Note that "drop-in replacement" means that it can be replaced without requiring any changes to the equipment. "Near drop-in replacement" means that it can be replaced with almost no changes to the equipment. "Retrofit replacement" means that it can be replaced with minimal changes (no major changes) to the equipment. The heat transfer fluid composition or heat transfer fluid of the present disclosure is preferably a drop-in replacement or a near drop-in replacement for the above-mentioned heat transfer fluids.

[0070] Whether a new heat transfer fluid can be used as a drop-in replacement, near drop-in replacement, or retrofit replacement can be determined by whether all of the following conditions are met: (i) The boiling point of the heat transfer fluid is at least about 80% or more, preferably at least about 85% or more, of the boiling point of the heat transfer fluid before replacement. (ii) The pour point of the heat transfer fluid is equal to or lower than the pour point of the heat transfer fluid before replacement. (iii) The kinematic viscosity of the heat transfer fluid is at least about 200% or less, preferably at least about 150% or less, of the kinematic viscosity of the heat transfer fluid before replacement. (iv) The heat transfer fluid is compatible with the heat transfer fluid before replacement in any proportion.

[0071] By setting the boiling point of the heat transfer fluid composition or heat transfer fluid of the present disclosure to at least about 80% or more, preferably at least about 85% or more, of the boiling point of the heat transfer fluid before replacement, the occurrence of cavitation and leakage from the device can be suppressed. The upper limit of the boiling point of the heat transfer fluid is not particularly limited, but it may be, for example, at least about 130% or less of the boiling point of the heat transfer fluid before replacement.

[0072] By setting the pour point of the heat transfer fluid composition or heat transfer fluid of the present disclosure to be equal to or lower than the pour point of the heat transfer fluid before replacement, it becomes possible to use the composition at temperatures lower than the conventional use temperature, thereby widening the use temperature range. The upper limit of the pour point of the heat transfer fluid is not particularly limited, but may be, for example, a temperature 30°C higher than the pour point of the heat transfer fluid before replacement.

[0073] By adjusting the kinematic viscosity of the heat transfer fluid composition or heat transfer fluid of the present disclosure to at least about 200% or less, preferably at least about 150% or less, of the kinematic viscosity of the heat transfer fluid before replacement, it is possible to suppress an increase in power consumption or reduce power consumption. The kinematic viscosity is preferably compared at the operating temperature, but is not limited thereto, and can be compared at any temperature between −20° C. and −40° C., specifically at −20° C.

[0074] The heat transfer fluid composition or heat transfer fluid of the present disclosure is compatible with the heat transfer fluid before replacement in any proportion, making replacement easy.

[0075] Furthermore, the heat transfer fluid composition or heat transfer fluid of the present disclosure is more suitable as a drop-in replacement, near drop-in replacement, or retrofit replacement if it satisfies the following conditions: (v) The heat transfer fluid composition or heat transfer fluid of the present disclosure has a dielectric constant of 120% or less of the heat transfer fluid before replacement. (vi) The heat transfer fluid composition or heat transfer fluid of the present disclosure has a dielectric strength of 90% or more of the heat transfer fluid before replacement. (vii) The heat transfer fluid composition or heat transfer fluid of the present disclosure has a specific heat of 90% or more of the heat transfer fluid before replacement. (viii) The heat transfer fluid composition or heat transfer fluid of the present disclosure has a thermal conductivity of 90% or more of the heat transfer fluid before replacement.

[0076] The dielectric constant of the heat transfer fluid composition or heat transfer fluid of the present disclosure can be set to 120% or less of the dielectric constant of the heat transfer fluid before replacement, so that the composition or heat transfer fluid can be suitably used as a replacement composition. The lower limit of the dielectric constant of the heat transfer fluid is not particularly limited, but may be, for example, 80% or more of the dielectric constant of the heat transfer fluid before replacement.

[0077] The heat transfer fluid composition or heat transfer fluid of the present disclosure can be suitably used as a replacement composition by adjusting the dielectric strength of the heat transfer fluid to 90% or more of the dielectric strength of the heat transfer fluid before replacement. The upper limit of the dielectric strength of the heat transfer fluid is not particularly limited, but it may be, for example, 120% or less of the dielectric strength of the heat transfer fluid before replacement.

[0078] The heat transfer fluid composition or heat transfer fluid of the present disclosure can be suitably used as a replacement composition by adjusting the specific heat thereof to 90% or more of the specific heat of the heat transfer fluid before replacement. The upper limit of the specific heat of the heat transfer fluid is not particularly limited, but it may be, for example, 120% or less of the specific heat of the heat transfer fluid before replacement.

[0079] The heat transfer fluid composition or heat transfer fluid of the present disclosure can be suitably used as a replacement composition by setting the thermal conductivity of the heat transfer fluid to 90% or more of the thermal conductivity of the heat transfer fluid before replacement. The upper limit of the thermal conductivity of the heat transfer fluid is not particularly limited, but it may be, for example, 120% or less of the thermal conductivity of the heat transfer fluid before replacement.

[0080] The boiling point of the heat transfer fluid composition or heat transfer fluid of the present disclosure is the temperature at which a peak resulting from endothermic heat is observed when the temperature is increased from 25°C at a rate of 5°C / min using DSC (differential scanning calorimetry).

[0081] The pour point of the heat transfer fluid composition or heat transfer fluid of the present disclosure is the temperature at which an endothermic peak is observed when the composition is cooled to below the freezing point with liquid nitrogen and then heated at a rate of 5°C / min using DSC.

[0082] The dielectric constant of the heat transfer fluid composition or heat transfer fluid of the present disclosure is a value observed at a frequency of 1 kHz in an environment of a temperature of 25° C. and a humidity of 60% using a capacitance method.

[0083] The kinematic viscosity and density of the heat transfer fluid composition or heat transfer fluid of the present disclosure can be measured using a kinematic viscometer SVM3001 manufactured by Anton Paar.

[0084] The dielectric strength of the heat transfer fluid composition or heat transfer fluid of the present disclosure is the breakdown voltage when a liquid sample is immersed between spherical electrodes adjusted to a predetermined distance and the voltage is increased at a constant rate. The measurement conditions are as follows: Electrode shape: spherical (φ12.5 mm) Electrode spacing: 2.5 mm Voltage increase rate: 2 kV / sec Measurement atmosphere: air (22°C, 57% RH)

[0085] The specific heat of the heat transfer fluid composition or heat transfer fluid of the present disclosure is a value obtained using DSC under the following conditions: Measuring device: Perkin-Elmer DSC8500 differential scanning calorimeter Heating rate: 10°C / min Standard sample: sapphire (-Al2O3) Atmosphere: in a dry nitrogen stream Sample container: aluminum sealed container

[0086] The thermal conductivity of the heat transfer fluid composition or heat transfer fluid of the present disclosure is a value that can be obtained by the transient thin wire method.

[0087] The compatibility of the heat transfer fluid composition or heat transfer fluid of the present disclosure is determined by whether or not it is compatible with the target solvent when mixed. Here, compatibility means that the two become homogeneous when mixed, i.e., the phase separation does not occur.

[0088] (Heat Transfer Apparatus) The present disclosure further provides a heat transfer apparatus comprising a device and a mechanism for transferring heat to or from the device, the mechanism comprising the heat transfer fluid composition or heat transfer fluid described above.

[0089] A device may be a component, work piece, assembly, etc. that is cooled, heated, or maintained at a predetermined temperature or temperature range. Devices include electrical, mechanical, and optical components, such as wafers used to manufacture semiconductors, semiconductor devices, computers, server computers, servers including blade servers; disk arrays / storage systems; storage area networks; network attached storage; storage communication systems; workstations; routers; telecommunications infrastructure / switches; wired, optical, and wireless communication devices; cell processing equipment; printers; power supplies; displays; optical devices; measurement systems including handheld systems; military electronics; chemical reactors; fuel cells; heat exchangers; electrochemical cells; microprocessors; power control semiconductors; power distribution switchgear; power transformers; circuit boards; multi-chip modules; packaged or unpackaged semiconductor devices; lasers, etc., preferably wafers used to manufacture semiconductors.

[0090] A semiconductor element is a heat-generating element mounted on a device, such as a CPU, a GPU, or an SSD. The semiconductor element is made of, for example, a single element such as silicon or germanium, or a compound semiconductor such as gallium arsenide (GaAs), gallium phosphide (GaP), indium phosphide (InP), gallium nitride (GaN), or silicon carbide (SiC).

[0091] When the device is a server computer, one or more logic boards are disposed within the interior space. The logic boards include a number of heat-generating electronic components, including at least one processor, such as a CPU, a GPU, etc. In addition, other heat-generating computer components may be used, such as a chipset; memory, graphics chips, network chips, RAM, power supplies, daughter cards; and storage drives, such as solid-state drives and mechanical hard disks.

[0092] The heat transfer device is a heat transfer device for transferring heat between the heat transfer object and the heat transfer target object using the heat transfer fluid, and transfers heat by thermal contact with the heat transfer target object. For example, when removing heat from the heat transfer target object, it is called cooling, and when supplying heat, it is called heating. Different mechanisms may be used depending on the case, but one heat transfer device may perform both cooling and heating.

[0093] Examples of heat transfer devices include, but are not limited to, pumps, valves, fluid containment systems, pressure control systems, coolers, heat exchangers, heat sources, heat sinks, refrigeration systems, active temperature control systems, and passive temperature control systems.

[0094] More specifically, the heat transfer apparatus includes a temperature-controlled wafer chuck in a plasma-enhanced chemical vapor deposition (PECVD) tool, a temperature-controlled test head for die performance testing, a temperature-controlled work area in semiconductor processing equipment, a thermal shock test bath liquid reservoir, a thermostatic chamber, and the like, preferably a temperature-controlled work area in semiconductor processing equipment.

[0095] The object to which heat is transferred, which is brought into thermal contact with the heat transfer device, is the same as described above.

[0096] The present disclosure also provides a semiconductor manufacturing apparatus including the heat transfer apparatus of the present disclosure.

[0097] The present disclosure discloses a method of heat transfer comprising providing a device and transferring heat to or from the device using the heat transfer fluid composition or heat transfer fluid described above. Here, heat can be transferred by placing a heat transfer apparatus in thermal contact with the device. When placed in thermal contact with the device, the heat transfer apparatus removes heat from the device, supplies heat to the device, or maintains the device at a selected temperature or temperature range. The direction of heat flow (from or to the device) is determined by the relative temperature difference between the device and the heat transfer apparatus.

[0098] Although the present invention has been described above, the present invention is not limited to the above and can be embodied in various forms without departing from the gist of the present invention.

[0099] The present disclosure will be described below with reference to examples, but the present disclosure is not limited to the following examples.

[0100] (Production of Hexafluoropropene Trimer) (Production Example 1) Hexafluoropropene trimer was obtained according to the method described in Chem Ber (1973), Vol. 106, pp. 2950-2959. The obtained HFP trimer was purified by distillation to remove impurities such as hexafluoropropene dimers and tetramers. Furthermore, the purified HFP trimer was separated by distillation into the compounds represented by formulas (I), (II), and (III).

[0101] The compounds represented by formulas (I), (II), and (III) obtained above were mixed so that the ratios of the compounds represented by formulas (I), (II), and (III) were as shown in the table below, thereby obtaining trimer mixtures 1 to 5.

[0102]

[0103] (Perfluorotripropylamine) FC-3283 manufactured by 3M Company was prepared as perfluorotripropylamine.

[0104] Example 1 A heat transfer fluid composition of Example 1 was obtained by mixing trimer mixture 1 and perfluorotripropylamine in a mass ratio of 50:50.

[0105] Example 2 A heat transfer fluid composition of Example 2 was obtained by mixing trimer mixture 2 and perfluorotripropylamine in a mass ratio of 50:50.

[0106] Example 3 A heat transfer fluid composition of Example 3 was obtained by mixing trimer mixture 2 and perfluorotripropylamine in a mass ratio of 75:25.

[0107] Example 4 A heat transfer fluid composition of Example 4 was obtained by mixing trimer mixture 3 and perfluorotripropylamine in a mass ratio of 50:50.

[0108] Example 5 A heat transfer fluid composition of Example 5 was obtained by mixing trimer mixture 3 and perfluorotripropylamine in a mass ratio of 75:25.

[0109] Example 6 A heat transfer fluid composition of Example 6 was obtained by mixing trimer mixture 4 and perfluorotripropylamine in a mass ratio of 50:50.

[0110] Example 7 A heat transfer fluid composition of Example 7 was obtained by mixing trimer mixture 4 and perfluorotripropylamine in a mass ratio of 75:25.

[0111] Example 8 A heat transfer fluid composition of Example 8 was obtained by mixing trimer mixture 5 and perfluorotripropylamine in a mass ratio of 50:50.

[0112] Example 9 A heat transfer fluid composition of Example 9 was obtained by mixing trimer mixture 5 and perfluorotripropylamine in a mass ratio of 75:25.

[0113] (Vapor-Liquid Equilibrium Simulation) A vapor-liquid equilibrium simulation was performed under atmospheric pressure using COSMOOther for mixtures of each of the compounds represented by formulas (I) to (III) of the present disclosure with perfluorotripropylamine. The results are shown in Figures 1 to 3 for the liquid phase molar fraction and vapor phase molar fraction of the compounds represented by formulas (I) to (III), respectively. The results confirmed that each compound has a pseudoazeotropic relationship with perfluorotripropylamine.

[0114] (Measurement of boiling point, kinematic viscosity, and dielectric constant) The boiling point was determined using DSC, and was taken as the temperature at which an endothermic peak was observed when the temperature was raised from 25°C at 5°C / min. The kinematic viscosity was measured at -50°C using an Ubbelohde viscometer in accordance with JIS K 2283. The dielectric constant was measured at a frequency of 1 kHz by the capacitance method in an environment of a temperature of 25°C and a humidity of 60%. The measured values ​​obtained were as shown in Table 1 below.

[0115]

[0116] From the above results, it was confirmed that Examples 1 to 9 had higher boiling points and lower kinematic viscosities compared to the weighted averages according to the mixing ratio.

[0117] The heat transfer fluid composition and heat transfer fluid of the present disclosure can be suitably used in various applications requiring heat transfer, particularly in semiconductor manufacturing processes.

Claims

1. C ９ F １８ A heat transfer fluid composition comprising a hexafluoropropene trimer represented by the formula:

2. The hexafluoropropene trimer is represented by the following formulas (I) to (III):

2. The heat transfer fluid composition of claim 1, comprising at least one hexafluoropropene trimer represented by the formula:

3. C ９ F １８ 3. The heat transfer fluid composition according to claim 1, wherein the mass ratio of the hexafluoropropene trimer represented by the formula (I) to the perfluorotripropylamine is 0.1:99.9 to 99.9 to 0.

1.

4. A heat transfer fluid composition according to claim 2 or 3, wherein the compound represented by formula (I) is contained in an amount of less than 85 mass% based on the total amount of the compounds represented by formulas (I) to (III).

5. A heat transfer fluid composition according to any one of claims 2 to 4, wherein the compound represented by formula (I) is contained in an amount of 50 mass % or more and less than 85 mass % based on the total amount of the compounds represented by formulas (I) to (III).

6. A heat transfer fluid composition according to any one of claims 2 to 5, wherein the compound represented by formula (I) is present in an amount of 85 mass% or more based on the total amount of the hexafluoropropene trimer.

7. Above C ９ F １８ The heat transfer fluid composition according to any one of claims 1 to 6, wherein the total amount of the hexafluoropropene trimer represented by the formula (I) and perfluorotripropylamine is 80 mass% or more in the heat transfer fluid composition.

8. The heat transfer fluid composition according to any one of claims 1 to 7, which is a pseudoazeotropic liquid.

9. The heat transfer fluid composition according to any one of claims 1 to 8, which is used in a semiconductor manufacturing process.

10. A heat transfer fluid comprising the heat transfer fluid composition according to any one of claims 1 to 9.

11. The heat transfer fluid of claim 10 further comprising a stabilizer.

12. The heat transfer fluid according to claim 10 or 11, used in a semiconductor manufacturing process.

13. Use of a heat transfer fluid composition according to any one of claims 1 to 9 or a heat transfer fluid according to any one of claims 10 to 12 for heat transfer.

14. A heat transfer apparatus comprising: a device; and a mechanism for transferring heat to or from the device, the mechanism comprising the heat transfer fluid composition according to any one of claims 1 to 9, or the heat transfer fluid according to any one of claims 10 to 12.

15. The heat transfer apparatus of claim 14, wherein the device is a wafer used to manufacture semiconductors.

16. A semiconductor manufacturing device comprising the heat transfer device according to claim 14 or 15.

17. A method for heat transfer comprising the steps of: preparing a device; and transferring heat to or from the device using a heat transfer fluid composition according to any one of claims 1 to 9, or a heat transfer fluid according to any one of claims 10 to 12.

18. The heat transfer method of claim 17, wherein the device is a wafer used to manufacture semiconductors.

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