Heat transfer fluid, method for exchanging heat between object and heat transfer fluid, use of composition, and composition

Abstract

Provided is a heat transfer fluid which exhibits thermal stability in a wide temperature range, is suitable for use, and has a short atmospheric life at a level that lowers the global warming potential. A heat transfer fluid according to the present disclosure contains a compound which is represented by formula (A), and in which the number of Si atoms in formula (A) is one, and the total mass of the compound represented by formula (A) in the heat transfer fluid is 5 mass% or more. (In formula (A), Y5, Y6, Y7, and Y8 each independently represent a substituent group having 1-20 carbon atoms.)

Description

HEAT TRANSFER FLUID, METHOD FOR EXCHANGING HEAT BETWEEN AN OBJECT AND A HEAT TRANSFER FLUID, USE OF THE COMPOSITION, AND COMPOSITION - Patent application

[0001] This disclosure relates to heat transfer fluids, methods for exchanging heat between a body and a heat transfer fluid, uses of the compositions, and compositions. This application claims priority to provisional application US 63 / 641,721 filed in the U.S. Patent and Trademark Office on May 2, 2024, and provisional application US 63 / 645,635 filed in the U.S. Patent and Trademark Office on May 10, 2024, the contents of which are incorporated herein by reference.

[0002] Currently, a variety of fluids are used for heat transfer. The suitability of a heat transfer fluid depends on the process of the application. For example, some electrical applications require a heat transfer fluid that is inert, has high dielectric strength, has low toxicity, has good environmental properties, and has good heat transfer properties over a wide temperature range. Other applications require precise temperature control and therefore require the heat transfer fluid to be single-phase over the entire process temperature range, and require that the heat transfer fluid properties be predictable, i.e., the composition remains relatively constant, viscosity, boiling point, etc. are predictable, precise temperatures can be maintained, and equipment can be appropriately designed.

[0003] Perfluorocarbons and perfluoropolyethers (PFPEs) have been used for heat transfer. Perfluorocarbons (PFCs) can have high dielectric strength and high resistivity. PFCs can be non-flammable, generally mechanically compatible with materials of construction, and exhibit limited solvent activity. In addition, PFCs generally exhibit low toxicity and good ease of use for operators. PFCs can be manufactured in a manner that results in products with narrow molecular weight distributions. However, PFCs and PFPEs may exhibit one significant disadvantage: long-term environmental persistence, which may increase their global warming potential. Materials currently used as heat transfer fluids for cooling electronic components or electrical equipment include PFCs, PFPEs, silicone oils, and hydrocarbon oils. Each of these heat transfer fluids has certain drawbacks. PFCs and PFPEs can be environmentally persistent. Silicone oils and hydrocarbon oils are typically flammable.

[0004] The following patent documents describe compounds used for heat transfer:

[0005] Japan Special Table No. 2023-540030 Publication Japanese Special Table No. 2014-515048

[0006] For example, systems such as systems for cooling wafer chucks in etchers, ashers, steppers, or PECVD equipment, systems for controlling the temperature in a test head for die performance testing, temperature control systems in semiconductor process equipment, thermal shock testing of electronic devices, and systems for maintaining constant temperatures for electronic devices, such as single-phase immersion cooling and two-phase immersion cooling, require heat transfer fluids that are thermally stable over a wide temperature range, suitable for various applications, and have a short atmospheric lifetime sufficient to reduce global warming potential. The heat transfer fluids provided include compounds represented by Formula (1), Formulas (A) to (D), and Formula (D1) below, which are easy to manufacture, function well as heat transfer fluids over a wide temperature range, and produce products that can be manufactured sustainably. Additionally, these compounds can be thermally stable at operating temperatures, typically from −50° C. to 130° C., and in some embodiments, up to about 230° C., and have a relatively short atmospheric lifetime compared to conventional materials. There is also a need for high temperature heat transfer devices and processes that include heat transfer fluids containing compounds represented by formula (1), formulas (A) to (D), and formula (D1).

[0007] In one aspect, an apparatus for heat transfer is provided that includes a device and a mechanism for transferring heat to or from the device, the mechanism including a heat transfer fluid, the heat transfer fluid including at least any of the compounds represented by Formula (1), Formulas (A) to (D), and Formula (D1): The mechanism is capable of transferring heat to or from the device or, in some embodiments, maintaining the device at a selected temperature.

[0008] In another aspect, there is provided a method for transferring heat that includes providing a device and transferring heat to or from the device using a mechanism, the mechanism including a heat transfer fluid, the heat transfer fluid including a compound represented by Formula (1), Formulas (A)-(D), and Formula (D1), below, which may have the same limitations as described in the apparatus summary above.

[0009] The provided compounds may be useful in heat transfer fluids. The provided compounds represented by the following formula (1), formulas (A) to (D), and formula (D1) have surprisingly good thermal stability. Furthermore, these silicon compounds have Si—C bonds with higher bond energy than C—C bonds and Si—O bonds with higher bond energy than C—O bonds, and therefore may also have high dielectric strength, low electrical conductivity, chemical inertness, hydrolytic stability, and good environmental properties. Furthermore, the compounds containing a difluoromethylene group (—CF ２ -) and trifluoromethyl group (-CF ３ ), it is believed that the compounds represented by the following formula (1), formulas (A) to (D), and formula (D1) provided below can also be useful in systems such as systems for cooling wafer chucks in etchers, ashers, steppers, or PECVD equipment, systems for controlling the temperature in a test head for die performance testing, temperature control systems in semiconductor process equipment, thermal shock testing of electronic devices, and systems for maintaining constant temperature of electronic devices, such as single-phase immersion cooling and two-phase immersion cooling.

[0010] The above summary is not intended to describe every disclosed embodiment of every implementation of the present disclosure. The following detailed description more particularly sets forth exemplary embodiments.

[0011] One aspect of the present disclosure is as follows: <1> A heat transfer fluid containing a compound represented by the following formula (A), wherein the number of Si atoms in formula (A) is 1, and the total mass of the compound represented by formula (A) in the heat transfer fluid is 5 mass% or more.

[0012]

[0013] In formula (A), Y ５ , Y ６ , Y ７ , and Y ８each independently represents a group having 1 to 20 carbon atoms, a hydrogen atom, or a halogen. <2> The heat transfer fluid according to <1>, wherein the compound represented by formula (A) is any of compounds represented by the following formulas (Aa) to (Ae):

[0014]

[0015] In formulas (Aa) to (Ae), R Ａ１ ~R Ａ２０ each independently represents a group containing 1 to 10 carbon atoms. Ａ１ ~R Ａ２０ are each independently any one selected from the group consisting of a methyl group, an ethyl group, a propyl group, a vinyl group, a propynyl group, a butyl group, and a phenyl group. Ａ１ ~R Ａ２０ <5> A heat transfer fluid comprising a compound represented by the following formula (C), wherein the number of Si atoms in the formula (C) is 4:

[0016]

[0017] In formula (C), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ each independently represents a group containing 1 to 20 carbon atoms, R ４１ represents a group containing 2 to 20 carbon atoms. ４１ <7> A heat transfer fluid according to <5>, wherein R ４１ is any one selected from the group consisting of an aryl group having 6 to 10 carbon atoms, a substituted aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 10 carbon atoms, and a substituted arylalkyl group having 7 to 10 carbon atoms. １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３<9> The heat transfer fluid according to <5>, wherein the compound represented by formula (C) is any of compounds represented by the following formulas:

[0018]

[0019] <10> The heat transfer fluid according to any one of <5> to <9>, wherein the total mass of the compounds represented by formula (C) in the heat transfer fluid is 51 mass% or more. <11> A heat transfer fluid containing a compound represented by the following formula (D):

[0020]

[0021] In formula (D), n represents an integer of 2 to 5. Each R independently represents a group containing 1 to 20 carbon atoms, provided that at least one of the Rs represents a group containing 2 to 20 carbon atoms. <12> The heat transfer fluid according to <11>, which contains a compound represented by the following formula (D1) as the compound represented by formula (D):

[0022]

[0023] In formula (D1), n ​​represents an integer of 2 to 5. Ｄ１ each independently represents a group containing 1 to 20 carbon atoms; R Ｄ２ each independently represents a group containing 2 to 20 carbon atoms. Ｄ１ is an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R Ｄ２ <14> The heat transfer fluid according to <12>, wherein in formula (D1), R is an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms. Ｄ１ is a methyl group, and R Ｄ２is an alkyl group having 2 or 3 carbon atoms, or an alkenyl group having 2 or 3 carbon atoms. <15> A method for exchanging heat between an object and the heat transfer fluid, comprising using the heat transfer fluid according to any one of <1> to <14>. <16> The method according to <15>, wherein the object is at least one selected from the group consisting of electronic computing equipment, microprocessors, semiconductor wafers used to manufacture semiconductor devices, power control semiconductors, electrochemical batteries (including lithium ion batteries), power distribution switch devices, power transformers, circuit boards, multi-chip modules, packaged or unpackaged semiconductor devices, fuel cells, and lasers. <17> The method according to <15>, wherein the heat transfer fluid is used in a system for cooling a device selected from the group consisting of a system for cooling a wafer chuck in an etcher, asher, stepper, or PECVD apparatus, a system for controlling the temperature in a test head for die performance testing, a temperature control system in semiconductor process equipment, a thermal shock test of an electronic device, and a system for maintaining a constant temperature of an electronic device. <18> The method of <15>, wherein the object is an electronic computing device, the electronic computing device including one or more electronic circuit boards, and the method comprises directly contacting the electronic circuit boards with the heat transfer fluid. <19> The method of <15>, wherein the object is an electronic computing device, the electronic computing device including one or more electronic circuit boards, and the method comprises directly contacting the electronic circuit boards with the heat transfer fluid. <15> The method of <15>, wherein the semiconductor processing device includes one or more semiconductor processing equipment selected from the group consisting of an etcher, an asher, a stepper, and a plasma-enhanced chemical vapor deposition (PECVD) chamber, the semiconductor processing equipment including at least one temperature control unit (TCU) that exchanges heat with the semiconductor device, and the TCU includes a heat transfer fluid. <20> An apparatus including an electronic computing device and a heat transfer fluid, the heat transfer fluid including any of the heat transfer fluids of <1> to <14>. <21> Use of a composition including the compound represented by formula (A) as a heat transfer fluid, wherein the number of Si atoms in formula (A) is 1, and the total mass of the compounds represented by formula (A) in the composition is 5 mass% or more. <22> Use of a composition containing a compound represented by formula (C) as a heat transfer fluid, wherein the number of Si atoms in formula (C) is 4.<23> Use of a composition containing the compound represented by formula (D) as a heat transfer fluid. <24> A composition containing the compound represented by formula (A), wherein the number of Si atoms in formula (A) is 1, the total mass of the compound represented by formula (A) in the composition is 5 mass% or more, and the volume resistivity is 1×10. ４ A composition having a vapor pressure of 10 kPa or less at 25°C and a viscosity of 100 kPa or less at 25°C. <25> A composition containing a compound represented by formula (C), wherein the number of Si atoms in formula (C) is 4, the vapor pressure at 25°C is 10 kPa or less, and the absolute viscosity at -20°C is 100 mPa.s or less. <26> A composition containing a compound represented by formula (D), wherein the vapor pressure at 25°C is 10 kPa or less, and the absolute viscosity at -20°C is 100 mPa.s or less.

[0024] Another aspect of the present disclosure includes the following: [1] A method for exchanging heat between an object and a heat transfer fluid, the method comprising using a heat transfer fluid containing a compound represented by the following formula (1):

[0025]

[0026] In formula (1), Y １ , Y ２ , Y ３ , and Y ４are each independently a hydrogen atom or an arbitrary substituent. [2] The method according to [1], wherein the compound represented by formula (1) contains two or more Si atoms. [3] The method according to [1] or [2], wherein the compound represented by formula (1) contains one or more O atoms. [4] The method according to any one of [1] to [3], wherein the compound represented by formula (1) contains Si—O in at least a part of its structure. [5] The method according to any one of [1] to [4], wherein the compound represented by formula (1) contains Si—O—Si in at least a part of its structure. [6] The method according to any one of [1] to [5], wherein the compound represented by formula (1) contains O—Si—O in at least a part of its structure. [7] The method according to any one of [1] to [6], wherein the compound represented by formula (1) contains an aromatic ring in at least a part of its structure. [8] The method according to any one of [1] to [7], wherein the compound represented by formula (1) contains five or less F atoms in its structure. [9] The method according to any one of [1] to [8], wherein the compound represented by formula (1) does not contain an F atom in its structure.

[10] The method according to any one of [1] to [9], wherein the content of the compound represented by formula (1) is at least 5 wt %, preferably more than 50 wt %, and more preferably more than 90 wt % of the heat transfer fluid.

[11] The method according to any one of [1] to

[10] , wherein the compound represented by formula (1) has a molecular weight of 100 to 2000.

[12] The method according to any one of [1] to

[11] , wherein the compound represented by formula (1) has a dynamic viscosity at 25°C of 0.1 cSt to 100 cSt.

[13] The method according to any one of [1] to

[12] , wherein the compound represented by formula (1) has an absolute viscosity at 25°C of 0.05 mPa·s to 200 mPa·s.

[14] The compound represented by formula (1) has a density at 25°C of 0.5 g / cm ３ ~2 g / cm ３The method according to any one of [1] to

[13] , wherein the compound represented by formula (1) has a heat of vaporization of 30 J / g to 300 J / g.

[15] The method according to any one of [1] to

[14] , wherein the compound represented by formula (1) has a boiling point of 30°C to 500°C.

[16] The method according to any one of [1] to

[15] , wherein the compound represented by formula (1) has a pour point of -180°C to 0°C.

[17] The method according to any one of [1] to

[16] , wherein the compound represented by formula (1) has a pour point of -180°C to 0°C.

[18] The method according to any one of [1] to

[17] , wherein the compound represented by formula (1) has a melting point of -180°C to 0°C.

[19] The method according to any one of [1] to

[18] , wherein the compound represented by formula (1) has a surface tension of 5 mN / m to 50 mN / m.

[20] The method according to any one of [1] to

[19] , wherein the compound represented by formula (1) has a vapor pressure of 0 kPa to 100 kPa.

[21] The method according to any one of [1] to

[20] , wherein the compound represented by formula (1) has a critical temperature of 30°C to 1000°C.

[22] The method according to any one of [1] to

[21] , wherein the compound represented by formula (1) has a critical pressure of 0.5 MPa to 5 MPa.

[23] The method according to any one of [1] to

[22] , wherein the compound represented by formula (1) has an expansion coefficient of 0.01 / K or less.

[24] The method according to any one of [1] to

[23] , wherein the compound represented by formula (1) has a Prandtl number at 40°C of 10 to 100.

[25] The method according to any one of [1] to

[24] , wherein the compound represented by formula (1) has a thermal conductivity of 0.01 W / m K to 1 W / m K.

[26] The method according to any one of [1] to

[25] , wherein the compound represented by formula (1) has a heat capacity of 100 J / kg K to 5000 J / kg K.

[27] The method according to any one of [1] to

[26] , wherein the compound represented by formula (1) has a relative dielectric constant of 1 to 10.

[28] The compound represented by formula (1) has a volume resistivity of 1×10 ６ Ω m to 1 x 10 １８The method according to any one of [1] to

[27] , wherein the dielectric strength of the compound represented by formula (1) is 1 kV to 100 kV.

[30] The method according to any one of [1] to

[29] , wherein the loss of purity of the compound represented by formula (1) when heated at 60°C for 24 hours is less than 5%.

[31] The method according to any one of [1] to

[30] , wherein the water solubility of the compound represented by formula (1) at 25°C is 0 ppm to 1000 ppm.

[32] The method according to any one of [1] to

[30] , wherein the water solubility of the compound represented by formula (1) at 25°C is 0 ppm to 1000 ppm.

[33] The method according to any one of [1] to

[32] , wherein the flash point of the compound represented by formula (1) is 30°C or higher.

[34] The method according to any one of [1] to

[33] , wherein the compound represented by formula (1) has a non-flammability index (NFPA) of 0 to 1.

[35] The method according to any one of [1] to

[34] , wherein the compound represented by formula (1) has a global warming potential (Global Warming Potential) of 10 or less.

[36] The method according to any one of [1] to

[35] , wherein the object is at least one selected from the group consisting of electronic computing equipment, microprocessors, semiconductor wafers used to manufacture semiconductor devices, power control semiconductors, electrochemical cells (including lithium ion batteries), power distribution switchgear, power transformers, circuit boards, multi-chip modules, packaged or unpackaged semiconductor devices, fuel cells, and lasers.

[37] The method according to any one of [1] to

[36] , wherein the object is electronic computing equipment, the electronic computing equipment comprising one or more electronic circuit boards, and the method comprises directly contacting the electronic circuit boards with the heat transfer fluid.

[38] The method according to any one of [1] to

[37] , wherein the method is a single-phase immersion cooling or two-phase immersion cooling method.

[39] The method according to any one of [1] to

[38] , which is used for a system for cooling a device selected from the group consisting of a system for cooling a wafer chuck in an etcher, an asher, a stepper, or a PECVD apparatus, a system for controlling the temperature in a test head for die performance testing, a temperature control system in semiconductor process equipment, a thermal shock test of an electronic device, and a constant temperature maintenance system for an electronic device.

[0027]

[40] The method according to any one of [1] to

[39] , wherein the compound represented by formula (1) is a compound represented by the following formula (2):

[0028] In formula (2), R １ , Y ２ , Y ３ , and Y ４

[41] In the formula (2), R １ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[42] The method according to any one of [1] to

[39] , wherein the compound represented by formula (1) is a compound represented by the following formula (3):

[0029]

[0030] In formula (3), R １ , R ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent.

[43] In the formula (3), R １ and R ２ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[44] The method according to any one of [1] to

[39] , wherein the compound represented by formula (1) is a compound represented by the following formula (4):

[0031]

[0032] In formula (4), R １ , R ２ , R ３ , and Y ３

[45] In the formula (4), R １ ~R ３ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[46] The method according to any one of [1] to

[39] , wherein the compound represented by formula (1) is a compound represented by the following formula (5):

[0033]

[0034] In formula (5), R １ , R ２ , R ３ , and R ４ are each independently a hydrogen atom or an arbitrary substituent. １ is a direct bond, an oxygen atom, or any linking group.

[47] In formula (5), L １

[48] ​​The method according to

[46] , wherein R is a direct bond or an alkylene group having 1 to 5 carbon atoms. １ ~R ４ are each independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.

[49] The method according to any one of [1] to

[39] , wherein the compound represented by formula (1) is a compound represented by the following formula (6):

[0035]

[0036] In formula (6), R １ , R ２ , R ３ , and R ４

[50] The method according to any one of [1] to

[39] , wherein the compound represented by formula (1) is a compound represented by formula (7):

[0037]

[0038] In formula (7), R １ , R ２ , and R ３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[51] The method according to any one of [1] to

[39] , wherein the compound represented by formula (1) is a compound represented by the following formula (8):

[0039]

[0040] In formula (8), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[52] In formula (8), L １

[53] The method according to

[51] , wherein R is a direct bond or an alkylene group having 1 to 5 carbon atoms. １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３

[54] The method according to

[51] or

[52] , wherein R is independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３

[55] The method according to any one of

[51] to

[53] , wherein Ar is independently an alkyl group having 1 to 5 carbon atoms. １

[56] The method according to any one of [1] to

[39] , wherein the compound represented by formula (1) is a compound represented by the following formula (9):

[0041]

[0042] In formula (9), R １１ ~R １３ , R ２１ ~R ２２ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and n represents an integer of 0 to 20.

[57] The method according to any one of [1] to

[39] , wherein the compound represented by formula (1) is a compound represented by the following formula (10):

[0043]

[0044] In formula (10), R １１ ~R １２ , R ２１ ~R ２２ , and R ３１ ~R ３２ are each independently a hydrogen atom or an arbitrary substituent, and Ar ２ , Ar ３ are each independently an aryl group which may be unsubstituted or substituted with one or more optional substituents. n represents an integer of 1 to 20.

[58] The method according to any one of [1] to

[39] , wherein the compound represented by formula (1) is a compound represented by the following formula (11):

[0045]

[0046] In formula (11), R １１ , R ２１ ~R ２２ , and R ３１ are each independently a hydrogen atom or an arbitrary substituent, and Ar ２１ ~Ar ２２ , and Ar ３１ ~Ar ３２are each independently an aryl group which may be unsubstituted or substituted with one or more optional substituents, and n is an integer of 0 to 20.

[0047]

[59] A method for manufacturing a semiconductor device, comprising using one or more semiconductor processing equipment selected from the group consisting of an etcher, an asher, a stepper, and a plasma-enhanced chemical vapor deposition (PECVD) chamber, wherein the semiconductor processing equipment comprises at least one temperature control unit (TCU) exchanging heat with the semiconductor device, the TCU comprising a heat transfer fluid, and the heat transfer fluid comprising a compound represented by the following formula (1):

[0048]

[0049] In formula (1), Y １ , Y ２ , Y ３ , and Y ４are each independently a hydrogen atom or an arbitrary substituent.

[60] The method according to

[59] , wherein the compound represented by formula (1) contains two or more Si atoms.

[61] The method according to

[59] or

[60] , wherein the compound represented by formula (1) contains one or more O atoms.

[62] The method according to any one of

[59] to

[61] , wherein the compound represented by formula (1) contains Si—O in at least a part of its structure.

[63] The method according to any one of

[59] to

[62] , wherein the compound represented by formula (1) contains Si—O—Si in at least a part of its structure.

[64] The method according to any one of

[59] to

[63] , wherein the compound represented by formula (1) contains O—Si—O in at least a part of its structure.

[65] The method according to any one of

[59] to

[64] , wherein the compound represented by formula (1) contains an aromatic ring in at least a part of its structure.

[66] The method according to any one of

[59] to

[65] , wherein the compound represented by formula (1) contains five or less F atoms in its structure.

[67] The method according to any one of

[59] to

[66] , wherein the compound represented by formula (1) does not contain an F atom in its structure.

[68] The method according to any one of

[59] to

[67] , wherein the content of the compound represented by formula (1) is at least 5 wt %, preferably more than 50 wt %, more preferably more than 90 wt % of the heat transfer fluid.

[69] The method according to any one of

[59] to

[68] , wherein the compound represented by formula (1) has a molecular weight of 100 to 2000.

[70] The method according to any one of

[59] to

[69] , wherein the compound represented by formula (1) has a dynamic viscosity at 25°C of 0.1 cSt to 100 cSt.

[71] The method according to any one of

[59] to

[70] , wherein the compound represented by formula (1) has an absolute viscosity at 25°C of 0.05 mPa·s to 200 mPa·s.

[72] The compound represented by formula (1) has a density at 25°C of 0.5 g / cm ３ ~2 g / cm ３The method according to any one of

[59] to

[71] , wherein the compound represented by formula (1) has a heat of vaporization of 30 J / g to 300 J / g.

[73] The method according to any one of

[59] to

[72] , wherein the compound represented by formula (1) has a boiling point of 30°C to 500°C.

[74] The method according to any one of

[59] to

[73] , wherein the compound represented by formula (1) has a pour point of -180°C to 0°C.

[75] The method according to any one of

[59] to

[74] , wherein the compound represented by formula (1) has a pour point of -180°C to 0°C.

[76] The method according to any one of

[59] to

[75] , wherein the compound represented by formula (1) has a melting point of -180°C to 0°C.

[77] The method according to any one of

[59] to

[76] , wherein the compound represented by formula (1) has a surface tension of 5 mN / m to 50 mN / m.

[78] The method according to any one of

[59] to

[77] , wherein the compound represented by formula (1) has a vapor pressure of 0 kPa to 100 kPa.

[79] The method according to any one of

[59] to

[78] , wherein the compound represented by formula (1) has a critical temperature of 30°C to 1000°C.

[80] The method according to any one of

[59] to

[79] , wherein the compound represented by formula (1) has a critical pressure of 0.5 MPa to 5 MPa.

[81] The method according to any one of

[59] to

[80] , wherein the compound represented by formula (1) has an expansion coefficient of 0.01 / K or less.

[82] The method according to any one of

[59] to

[81] , wherein the compound represented by formula (1) has a Prandtl number at 40°C of 10 to 100.

[83] The method according to any one of

[59] to

[82] , wherein the compound represented by formula (1) has a thermal conductivity of 0.01 W / m K to 1 W / m K.

[84] The method according to any one of

[59] to

[83] , wherein the compound represented by formula (1) has a heat capacity of 100 J / kg K to 5000 J / kg K.

[85] The method according to any one of

[59] to

[84] , wherein the compound represented by formula (1) has a relative dielectric constant of 1 to 10.

[86] The compound represented by formula (1) has a volume resistivity of 1 x 10 ６ Ω m to 1 x 10 １８The method according to any one of

[59] to

[85] , wherein the dielectric strength of the compound represented by formula (1) is 1 kV to 100 kV.

[87] The method according to any one of

[59] to

[86] , wherein the compound represented by formula (1) loses less than 5% purity when heated at 60°C for 24 hours.

[89] The method according to any one of

[59] to

[88] , wherein the compound represented by formula (1) has a water solubility of 0 ppm to 1000 ppm at 25°C.

[90] The method according to any one of

[59] to

[89] , wherein the compound represented by formula (1) has a water solubility of 0 ppm to 1000 ppm at 25°C.

[91] The method according to any one of

[59] to

[90] , wherein the compound represented by formula (1) has a flash point of 30°C or higher.

[92] The method according to any one of

[59] to

[91] , wherein the compound represented by formula (1) has a non-flammability (NFPA) of 0 to 1.

[93] The method according to any one of

[59] to

[92] , wherein the compound represented by formula (1) has a global warming potential of 10 or less.

[0050]

[94] The method according to any one of

[59] to

[93] , wherein the compound represented by formula (1) is a compound represented by the following formula (2):

[0051]

[0052] In formula (2), R １ , Y ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent.

[95] In the formula (2), R １ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[96] The method according to any one of

[59] to

[93] , wherein the compound represented by formula (1) is a compound represented by the following formula (3):

[0053]

[0054] In formula (3), R １ , R ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent.

[97] In the formula (3), R １ and R ２ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[98] The method according to any one of

[59] to

[93] , wherein the compound represented by formula (1) is a compound represented by the following formula (4):

[0055]

[0056] In formula (4), R １ , R ２ , R ３ , and Y ３ are each independently a hydrogen atom or an arbitrary substituent.

[99] In the formula (4), R １ ~R ３ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[100] The method according to any one of

[59] to

[93] , wherein the compound represented by formula (1) is a compound represented by the following formula (5):

[0057]

[0058] In formula (5), R １ , R ２ , R ３ , and R ４ are each independently a hydrogen atom or an arbitrary substituent. １ is a direct bond, an oxygen atom, or any linking group.

[101] In formula (5), L １

[102] In formula (5), R is a direct bond or an alkylene group having 1 to 5 carbon atoms. １ ~R ４are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 5 carbon atoms or aryl groups having 6 to 20 carbon atoms.

[103] The method according to any one of

[59] to

[93] , wherein the compound represented by formula (1) is a compound represented by the following formula (6):

[0059]

[0060] In formula (6), R １ , R ２ , R ３ , and R ４

[104] The method according to any one of

[59] to

[93] , wherein the compound represented by formula (1) is a compound represented by formula (7):

[0061]

[0062] In formula (7), R １ , R ２ , and R ３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[105] The method according to any one of

[59] to

[93] , wherein the compound represented by formula (1) is a compound represented by formula (8):

[0063]

[0064] In formula (8), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[106] In formula (8), L１

[107] The method according to

[105] , wherein R is a direct bond or an alkylene group having 1 to 5 carbon atoms. １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ The method according to

[105] or

[106] , wherein R is independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３

[109] In formula (8), Ar １

[110] The method according to any one of

[59] to

[93] , wherein the compound represented by formula (1) is a compound represented by the following formula (9):

[0065]

[0066] In formula (9), R １１ ~R １３ , R ２１ ~R ２２ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and n represents an integer of 0 to 20.

[111] The method according to any one of

[59] to

[93] , wherein the compound represented by formula (1) is a compound represented by the following formula (10):

[0067]

[0068] In formula (10), R １１ ~R １２ , R ２１ ~R ２２ , and R ３１ ~R ３２ are each independently a hydrogen atom or an arbitrary substituent, and Ar ２ , Ar３ are each independently an aryl group which may be unsubstituted or substituted with one or more optional substituents. n represents an integer of 1 to 20.

[112] The method according to any one of

[59] to

[93] , wherein the compound represented by formula (1) is a compound represented by the following formula (11):

[0069]

[0070] In formula (11), R １１ , R ２１ ~R ２２ , and R ３１ are each independently a hydrogen atom or an arbitrary substituent, and Ar ２１ ~Ar ２２ , and Ar ３１ ~Ar ３２ are each independently an aryl group which may be unsubstituted or substituted with one or more optional substituents, and n is an integer of 0 to 20.

[0071]

[113] A method for thermal shock testing of a semiconductor device, the method comprising, in any order: i. cooling the semiconductor device to a temperature comprised between −10° C. and −100° C., preferably between −10° C. and −40° C., using a first bath made of a heat transfer fluid; and ii. heating the semiconductor device to a temperature comprised between 60° C. and 250° C., using a second bath made of a heat transfer fluid, wherein one or preferably both of the first and second baths are made of a heat transfer fluid comprising a compound represented by the following formula (1):

[0072]

[0073] In formula (1), Y １ , Y ２ , Y ３ , and Y ４are each independently a hydrogen atom or an arbitrary substituent.

[114] The method according to

[113] , wherein the compound represented by formula (1) contains two or more Si atoms.

[115] The method according to

[113] or

[114] , wherein the compound represented by formula (1) contains one or more O atoms.

[116] The method according to any one of

[113] to

[115] , wherein the compound represented by formula (1) contains Si—O in at least a part of its structure.

[117] The method according to any one of

[113] to

[116] , wherein the compound represented by formula (1) contains Si—O—Si in at least a part of its structure.

[118] The method according to any one of

[113] to

[117] , wherein the compound represented by formula (1) contains O—Si—O in at least a part of its structure.

[119] The method according to any one of

[113] to

[118] , wherein the compound represented by formula (1) contains an aromatic ring in at least a part of its structure.

[120] The method according to any one of

[113] to

[119] , wherein the compound represented by formula (1) contains 5 or less F atoms in its structure.

[121] The method according to any one of

[113] to

[120] , wherein the compound represented by formula (1) does not contain F atoms in its structure.

[122] The method according to any one of

[113] to

[121] , wherein the content of the compound represented by formula (1) is at least 5 wt %, preferably more than 50 wt %, more preferably more than 90 wt %, of the heat transfer fluid.

[123] The method according to any one of

[113] to

[122] , wherein the compound represented by formula (1) has a molecular weight of 100 to 2000.

[124] The method according to any one of

[113] to

[123] , wherein the compound represented by formula (1) has a dynamic viscosity at 25°C of 0.1 cSt to 100 cSt.

[125] The method according to any one of

[113] to

[124] , wherein the compound represented by formula (1) has an absolute viscosity at 25°C of 0.05 mPa s to 200 mPa s.

[126] The compound represented by formula (1) has a density at 25°C of 0.5 g / cm ３ ~2 g / cm ３The method according to any one of

[113] to

[125] , wherein the compound represented by formula (1) has a heat of vaporization of 30 J / g to 300 J / g.

[127] The method according to any one of

[113] to

[126] , wherein the compound represented by formula (1) has a boiling point of 30°C to 500°C.

[128] The method according to any one of

[113] to

[127] , wherein the compound represented by formula (1) has a pour point of -180°C to 0°C.

[130] The method according to any one of

[113] to

[129] , wherein the compound represented by formula (1) has a melting point of -180°C to 0°C.

[131] The method according to any one of

[113] to

[130] , wherein the compound represented by formula (1) has a surface tension of 5 mN / m to 50 mN / m.

[132] The method according to any one of

[113] to

[131] , wherein the compound represented by formula (1) has a vapor pressure of 0 kPa to 100 kPa.

[133] The method according to any one of

[113] to

[132] , wherein the compound represented by formula (1) has a critical temperature of 30°C to 1000°C.

[134] The method according to any one of

[113] to

[133] , wherein the compound represented by formula (1) has a critical pressure of 0.5 MPa to 5 MPa.

[135] The method according to any one of

[113] to

[134] , wherein the compound represented by formula (1) has an expansion coefficient of 0.01 / K or less.

[136] The method according to any one of

[113] to

[135] , wherein the compound represented by formula (1) has a Prandtl number at 40°C of 10 to 100.

[137] The method according to any one of

[113] to

[136] , wherein the compound represented by formula (1) has a thermal conductivity of 0.01 W / m K to 1 W / m K.

[138] The method according to any one of

[113] to

[137] , wherein the compound represented by formula (1) has a heat capacity of 100 J / kg K to 5000 J / kg K.

[139] The method according to any one of

[113] to

[138] , wherein the compound represented by formula (1) has a relative dielectric constant of 1 to 10.

[140] The method according to any one of

[113] to

[138] , wherein the compound represented by formula (1) has a volume resistivity of 1 x 10 ６ Ω m to 1 x 10 １８The method according to any one of

[113] to

[139] , wherein the compound represented by formula (1) has a dielectric strength of 1 kV to 100 kV.

[142] The method according to any one of

[113] to

[141] , wherein the compound represented by formula (1) loses less than 5% purity when heated at 60°C for 24 hours.

[143] The method according to any one of

[113] to

[142] , wherein the compound represented by formula (1) has a water solubility of 0 ppm to 1000 ppm at 25°C.

[144] The method according to any one of

[113] to

[143] , wherein the compound represented by formula (1) has a water solubility of 0 ppm to 1000 ppm at 25°C.

[145] The method according to any one of

[113] to

[144] , wherein the compound represented by formula (1) has a flash point of 30°C or higher.

[146] The method according to any one of

[113] to

[145] , wherein the compound represented by formula (1) has a non-flammability (NFPA) of 0 to 1.

[147] The method according to any one of

[113] to

[146] , wherein the compound represented by formula (1) has a global warming potential of 10 or less.

[148] The method according to any one of

[113] to

[147] , wherein the compound represented by formula (1) is a compound represented by the following formula (2):

[0074]

[0075] In formula (2), R １ , Y ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent.

[149] In the formula (2), R １ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[150] The method according to any one of

[113] to

[147] , wherein the compound represented by formula (1) is a compound represented by the following formula (3):

[0076]

[0077] In formula (3), R １ , R ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent.

[151] In the formula (3), R １ and R ２ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[152] The method according to any one of

[113] to

[147] , wherein the compound represented by formula (1) is a compound represented by the following formula (4):

[0078]

[0079] In formula (4), R １ , R ２ , R ３ , and Y ３ are each independently a hydrogen atom or an arbitrary substituent.

[153] In the formula (4), R １ ~R ３ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[154] The method according to any one of

[113] to

[147] , wherein the compound represented by formula (1) is a compound represented by the following formula (5):

[0080]

[0081] In formula (5), R １ , R ２ , R ３ , and R ４ are each independently a hydrogen atom or an arbitrary substituent. １ is a direct bond, an oxygen atom, or any linking group.

[155] In formula (5), L １

[156] The method according to

[154] , wherein R is a direct bond or an alkylene group having 1 to 5 carbon atoms. １ ~R ４are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 5 carbon atoms or aryl groups having 6 to 20 carbon atoms.

[157] The method according to any one of

[113] to

[147] , wherein the compound represented by formula (1) is a compound represented by the following formula (6):

[0082]

[0083] In formula (6), R １ , R ２ , R ３ , and R ４

[158] The method according to any one of

[113] to

[147] , wherein the compound represented by formula (1) is a compound represented by formula (7):

[0084]

[0085] In formula (7), R １ , R ２ , and R ３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[159] The method according to any one of

[113] to

[147] , wherein the compound represented by formula (1) is a compound represented by the following formula (8):

[0086]

[0087] In formula (8), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[160] In formula (8), L１

[161] The method according to

[159] , wherein R is a direct bond or an alkylene group having 1 to 5 carbon atoms. １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３

[162] The method according to

[159] or

[160] , wherein R is independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３

[163] In formula (8), Ar １

[164] The method according to any one of

[113] to

[147] , wherein the compound represented by formula (1) is a compound represented by the following formula (9):

[0088]

[0089] In formula (9), R １１ ~R １３ , R ２１ ~R ２２ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and n represents an integer of 0 to 20.

[165] The method according to any one of

[113] to

[147] , wherein the compound represented by formula (1) is a compound represented by the following formula (10):

[0090]

[0091] In formula (10), R １１ ~R １２ , R ２１ ~R ２２ , and R ３１ ~R ３２ are each independently a hydrogen atom or an arbitrary substituent, and Ar ２, Ar ３ are each independently an aryl group which may be unsubstituted or substituted with one or more optional substituents. n represents an integer of 1 to 20.

[166] The method according to any one of

[113] to

[147] , wherein the compound represented by formula (1) is a compound represented by the following formula (11):

[0092]

[0093] In formula (11), R １１ , R ２１ ~R ２２ , and R ３１ are each independently a hydrogen atom or an arbitrary substituent, and Ar ２１ ~Ar ２２ , and Ar ３１ ~Ar ３２ are each independently an aryl group which may be unsubstituted or substituted with one or more optional substituents, and n is an integer of 0 to 20.

[0094]

[167] A method for vapor phase soldering of a semiconductor device, comprising: i. providing a semiconductor device containing a soldering paste; ii. providing a sealed chamber containing a heat transfer fluid at its boiling point such that heated vapor of the heat transfer fluid is generated in the sealed chamber; iii. introducing the semiconductor device into the sealed chamber in contact with the vapor of the heat transfer fluid, thereby melting the soldering paste by contact with the heated vapor; wherein the heat transfer fluid contains a compound represented by the following formula (1):

[0095]

[0096] In formula (1), Y １ , Y ２ , Y ３ , and Y ４are each independently a hydrogen atom or an arbitrary substituent.

[168] The method according to

[167] , wherein the compound represented by formula (1) contains two or more Si atoms.

[169] The method according to

[167] or

[168] , wherein the compound represented by formula (1) contains one or more O atoms.

[170] The method according to any one of

[167] to

[169] , wherein the compound represented by formula (1) contains Si—O in at least a part of its structure.

[171] The method according to any one of

[167] to

[170] , wherein the compound represented by formula (1) contains Si—O—Si in at least a part of its structure.

[172] The method according to any one of

[167] to

[171] , wherein the compound represented by formula (1) contains O—Si—O in at least a part of its structure.

[173] The method according to any one of

[167] to

[172] , wherein the compound represented by formula (1) contains an aromatic ring in at least a part of its structure.

[174] The method according to any one of

[167] to

[173] , wherein the compound represented by formula (1) contains 5 or less F atoms in its structure.

[175] The method according to any one of

[167] to

[174] , wherein the compound represented by formula (1) does not contain F atoms in its structure.

[176] The method according to any one of

[167] to

[175] , wherein the content of the compound represented by formula (1) is at least 5 wt %, preferably more than 50 wt %, more preferably more than 90 wt %, of the heat transfer fluid.

[177] The method according to any one of

[167] to

[176] , wherein the compound represented by formula (1) has a molecular weight of 100 to 2000.

[178] The method according to any one of

[167] to

[177] , wherein the compound represented by formula (1) has a dynamic viscosity at 25°C of 0.1 cSt to 100 cSt.

[179] The method according to any one of

[167] to

[178] , wherein the compound represented by formula (1) has an absolute viscosity at 25°C of 0.05 mPa s to 200 mPa s.

[180] The compound represented by formula (1) has a density at 25°C of 0.5 g / cm ３ ~2 g / cm ３The method according to any one of

[167] to

[179] , wherein the compound represented by formula (1) has a heat of vaporization of 30 J / g to 300 J / g.

[181] The method according to any one of

[167] to

[180] , wherein the compound represented by formula (1) has a boiling point of 30°C to 500°C.

[182] The method according to any one of

[167] to

[181] , wherein the compound represented by formula (1) has a pour point of -180°C to 0°C.

[183] ​​The method according to any one of

[167] to

[182] , wherein the compound represented by formula (1) has a pour point of -180°C to 0°C.

[184] The method according to any one of

[167] to

[183] , wherein the compound represented by formula (1) has a melting point of -180°C to 0°C.

[185] The method according to any one of

[167] to

[184] , wherein the compound represented by formula (1) has a surface tension of 5 mN / m to 50 mN / m.

[186] The method according to any one of

[167] to

[185] , wherein the compound represented by formula (1) has a vapor pressure of 0 kPa to 100 kPa.

[187] The method according to any one of

[167] to

[186] , wherein the compound represented by formula (1) has a critical temperature of 30°C to 1000°C.

[188] The method according to any one of

[167] to

[187] , wherein the compound represented by formula (1) has a critical pressure of 0.5 MPa to 5 MPa.

[189] The method according to any one of

[167] to

[188] , wherein the compound represented by formula (1) has an expansion coefficient of 0.01 / K or less.

[190] The method according to any one of

[167] to

[189] , wherein the compound represented by formula (1) has a Prandtl number at 40°C of 10 to 100.

[191] The method according to any one of

[167] to

[190] , wherein the compound represented by formula (1) has a thermal conductivity of 0.01 W / m K to 1 W / m K.

[192] The method according to any one of

[167] to

[191] , wherein the compound represented by formula (1) has a heat capacity of 100 J / kg K to 5000 J / kg K.

[193] The method according to any one of

[167] to

[192] , wherein the compound represented by formula (1) has a relative dielectric constant of 1 to 10.

[194] The method according to any one of

[167] to

[192] , wherein the compound represented by formula (1) has a volume resistivity of 1 x 10 ６ Ω m to 1 x 10 １８The method according to any one of

[167] to

[193] , wherein the compound represented by formula (1) has a dielectric strength of 1 kV to 100 kV.

[196] The method according to any one of

[167] to

[195] , wherein the compound represented by formula (1) loses less than 5% purity when heated at 60°C for 24 hours.

[197] The method according to any one of

[167] to

[196] , wherein the compound represented by formula (1) has a water solubility of 0 ppm to 1000 ppm at 25°C.

[198] The method according to any one of

[167] to

[197] , wherein the compound represented by formula (1) has a water solubility of 0 ppm to 1000 ppm at 25°C.

[199] The method according to any one of

[167] to

[198] , wherein the compound represented by formula (1) has a flash point of 30°C or higher.

[200] The method according to any one of

[167] to

[199] , wherein the compound represented by formula (1) has a non-flammability (NFPA) of 0 to 1.

[201] The method according to any one of

[167] to

[200] , wherein the compound represented by formula (1) has a global warming potential of 10 or less.

[202] The method according to any one of

[167] to

[201] , wherein the compound represented by formula (1) is a compound represented by the following formula (2):

[0097]

[0098] In formula (2), R １ , Y ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent.

[203] In the formula (2), R １ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[204] The method according to any one of

[167] to

[201] , wherein the compound represented by formula (1) is a compound represented by the following formula (3):

[0099]

[0100] In formula (3), R １ , R ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent.

[205] In the formula (3), R １ and R ２ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[206] The method according to any one of

[167] to

[201] , wherein the compound represented by formula (1) is a compound represented by the following formula (4):

[0101]

[0102] In formula (4), R １ , R ２ , R ３ , and Y ３ are each independently a hydrogen atom or an arbitrary substituent.

[207] In the formula (4), R １ ~R ３ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[208] The method according to any one of

[167] to

[201] , wherein the compound represented by formula (1) is a compound represented by the following formula (5):

[0103]

[0104] In formula (5), R １ , R ２ , R ３ , and R ４ are each independently a hydrogen atom or an arbitrary substituent. １ is a direct bond, an oxygen atom, or any linking group.

[209] In formula (5), L １

[210] The method according to

[208] , wherein R is a direct bond or an alkylene group having 1 to 5 carbon atoms. １ ~R ４are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 5 carbon atoms or aryl groups having 6 to 20 carbon atoms.

[211] The method according to any one of

[167] to

[201] , wherein the compound represented by formula (1) is a compound represented by the following formula (6):

[0105]

[0106] In formula (6), R １ , R ２ , R ３ , and R ４

[212] The method according to any one of

[167] to

[201] , wherein the compound represented by formula (1) is a compound represented by formula (7):

[0107]

[0108] In formula (7), R １ , R ２ , and R ３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[213] The method according to any one of

[167] to

[201] , wherein the compound represented by formula (1) is a compound represented by formula (8):

[0109]

[0110] In formula (8), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[214] In formula (8), L１

[215] The method according to

[213] , wherein R is a direct bond or an alkylene group having 1 to 5 carbon atoms. １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３

[216] The method according to

[213] or

[214] , wherein R is independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３

[217] The method according to any one of

[213] to

[215] , wherein Ar is each independently an alkyl group having 1 to 5 carbon atoms. １

[218] The method according to any one of

[167] to

[201] , wherein the compound represented by formula (1) is a compound represented by the following formula (9):

[0111]

[0112] In formula (9), R １１ ~R １３ , R ２１ ~R ２２ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and n represents an integer of 0 to 20.

[219] The method according to any one of

[167] to

[201] , wherein the compound represented by formula (1) is a compound represented by the following formula (10):

[0113]

[0114] In formula (10), R １１ ~R １２ , R ２１ ~R ２２ , and R ３１ ~R ３２ are each independently a hydrogen atom or an arbitrary substituent, and Ar ２, Ar ３ are each independently an aryl group which may be unsubstituted or substituted with one or more optional substituents. n represents an integer of 1 to 20.

[220] The method according to any one of

[167] to

[201] , wherein the compound represented by formula (1) is a compound represented by the following formula (11):

[0115]

[0116] In formula (11), R １１ , R ２１ ~R ２２ , and R ３１ are each independently a hydrogen atom or an arbitrary substituent, and Ar ２１ ~Ar ２２ , and Ar ３１ ~Ar ３２ are each independently an aryl group which may be unsubstituted or substituted with one or more optional substituents, and n is an integer of 0 to 20.

[0117]

[221] An apparatus comprising an electronic computing device and a heat transfer fluid, wherein the heat transfer fluid comprises a compound represented by formula (1):

[0118]

[0119] In formula (1), Y １ , Y ２ , Y ３ , and Y ４are each independently a hydrogen atom or an arbitrary substituent.

[222] The device according to

[221] , wherein the compound represented by formula (1) contains two or more Si atoms.

[223] The device according to

[221] or

[222] , wherein the compound represented by formula (1) contains one or more O atoms.

[224] The device according to any one of

[221] to

[223] , wherein the compound represented by formula (1) contains Si—O in at least a part of its structure.

[225] The device according to any one of

[221] to

[224] , wherein the compound represented by formula (1) contains Si—O—Si in at least a part of its structure.

[226] The device according to any one of

[221] to

[225] , wherein the compound represented by formula (1) contains O—Si—O in at least a part of its structure.

[227] The device according to any one of

[221] to

[226] , wherein the compound represented by formula (1) contains an aromatic ring in at least a part of its structure.

[228] The device according to any one of

[221] to

[227] , wherein the compound represented by formula (1) contains five or fewer F atoms in its structure.

[229] The device according to any one of

[221] to

[228] , wherein the compound represented by formula (1) does not contain F atoms in its structure.

[230] The device according to any one of

[221] to

[229] , wherein the content of the compound represented by formula (1) is at least 5 wt %, preferably more than 50 wt %, and more preferably more than 90 wt %, of the heat transfer fluid.

[231] The device according to any one of

[221] to

[230] , wherein the compound represented by formula (1) has a molecular weight of 100 to 2000.

[232] The device according to any one of

[221] to

[231] , wherein the compound represented by formula (1) has a dynamic viscosity at 25°C of 0.1 cSt to 100 cSt.

[233] The device according to any one of

[221] to

[232] , wherein the compound represented by formula (1) has an absolute viscosity at 25°C of 0.05 mPa s to 200 mPa s.

[234] The compound represented by formula (1) has a density at 25°C of 0.5 g / cm ３ ~2 g / cm ３The device according to any one of

[221] to

[233] , wherein the compound represented by formula (1) has a heat of vaporization of 30 J / g to 300 J / g.

[235] The device according to any one of

[221] to

[234] , wherein the compound represented by formula (1) has a boiling point of 30°C to 500°C.

[236] The device according to any one of

[221] to

[235] , wherein the compound represented by formula (1) has a pour point of -180°C to 0°C.

[237] The device according to any one of

[221] to

[236] , wherein the compound represented by formula (1) has a pour point of -180°C to 0°C.

[238] The device according to any one of

[221] to

[237] , wherein the compound represented by formula (1) has a melting point of -180°C to 0°C.

[239] The device according to any one of

[221] to

[238] , wherein the compound represented by formula (1) has a surface tension of 5 mN / m to 50 mN / m.

[240] The device according to any one of

[221] to

[239] , wherein the compound represented by formula (1) has a vapor pressure of 0 kPa to 100 kPa.

[241] The device according to any one of

[221] to

[240] , wherein the compound represented by formula (1) has a critical temperature of 30°C to 1000°C.

[242] The device according to any one of

[221] to

[241] , wherein the compound represented by formula (1) has a critical pressure of 0.5 MPa to 5 MPa.

[243] The device according to any one of

[221] to

[242] , wherein the compound represented by formula (1) has an expansion coefficient of 0.01 / K or less.

[244] The device according to any one of

[221] to

[243] , wherein the compound represented by formula (1) has a Prandtl number at 40°C of 10 to 100.

[245] The device according to any one of

[221] to

[244] , wherein the compound represented by formula (1) has a thermal conductivity of 0.01 W / m K to 1 W / m K.

[246] The device according to any one of

[221] to

[245] , wherein the compound represented by formula (1) has a heat capacity of 100 J / kg K to 5000 J / kg K.

[247] The device according to any one of

[221] to

[246] , wherein the compound represented by formula (1) has a relative dielectric constant of 1 to 10.

[248] The device according to any one of

[221] to

[246] , wherein the compound represented by formula (1) has a volume resistivity of 1 x 10 ６ Ω m to 1 x 10 １８The device according to any one of

[221] to

[247] , wherein the dielectric strength of the compound represented by formula (1) is 1 kV to 100 kV.

[249] The device according to any one of

[221] to

[248] , wherein the compound represented by formula (1) loses less than 5% purity when heated at 60°C for 24 hours.

[251] The device according to any one of

[221] to

[250] , wherein the compound represented by formula (1) has a water solubility of 0 ppm to 1000 ppm at 25°C.

[252] The device according to any one of

[221] to

[251] , wherein the compound represented by formula (1) has a water solubility of 0 ppm to 1000 ppm at 25°C.

[253] The device according to any one of

[221] to

[252] , wherein the compound represented by formula (1) has a flash point of 30°C or higher.

[254] The device according to any one of

[221] to

[253] , wherein the compound represented by formula (1) has a non-flammability (NFPA) of 0 to 1.

[255] The device according to any one of

[221] to

[254] , wherein the compound represented by formula (1) has a global warming potential of 10 or less.

[256] The device according to any one of

[221] to

[255] , wherein the compound represented by formula (1) is a compound represented by the following formula (2):

[0120]

[0121] In formula (2), R １ , Y ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent.

[257] In the formula (2), R １ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[258] The device according to any one of

[221] to

[255] , wherein the compound represented by formula (1) is a compound represented by the following formula (3):

[0122]

[0123] In formula (3), R １ , R ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent.

[259] In the formula (3), R １ and R ２ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[260] The device according to any one of

[221] to

[255] , wherein the compound represented by formula (1) is a compound represented by the following formula (4):

[0124]

[0125] In formula (4), R １ , R ２ , R ３ , and Y ３ are each independently a hydrogen atom or an arbitrary substituent.

[261] In the formula (4), R １ ~R ３ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[262] The device according to any one of

[221] to

[255] , wherein the compound represented by formula (1) is a compound represented by the following formula (5):

[0126]

[0127] In formula (5), R １ , R ２ , R ３ , and R ４ are each independently a hydrogen atom or an arbitrary substituent. １ is a direct bond, an oxygen atom, or any linking group.

[263] In formula (5), L １ is a direct bond or an alkylene group having 1 to 5 carbon atoms. １ ~R ４are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 5 carbon atoms or aryl groups having 6 to 20 carbon atoms.

[265] The device according to any one of

[221] to

[255] , wherein the compound represented by formula (1) is a compound represented by the following formula (6):

[0128]

[0129] In formula (6), R １ , R ２ , R ３ , and R ４ are each independently a hydrogen atom or an arbitrary substituent.

[266] The device according to any one of

[221] to

[255] , wherein the compound represented by formula (1) is a compound represented by the following formula (7):

[0130]

[0131] In formula (7), R １ , R ２ , and R ３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[267] The device according to any one of

[221] to

[255] , wherein the compound represented by formula (1) is a compound represented by the following formula (8):

[0132]

[0133] In formula (8), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[268] In formula (8), L１

[269] In formula (8), R is a direct bond or an alkylene group having 1 to 5 carbon atoms. １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３

[270] In formula (8), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３

[271] In formula (8), Ar is an alkyl group having 1 to 5 carbon atoms. １

[272] The device according to any one of

[221] to

[255] , wherein the compound represented by formula (1) is a compound represented by the following formula (9):

[0134]

[0135] In formula (9), R １１ ~R １３ , R ２１ ~R ２２ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and n represents an integer of 0 to 20.

[273] The device according to any one of

[221] to

[255] , wherein the compound represented by formula (1) is a compound represented by the following formula (10):

[0136]

[0137] In formula (10), R １１ ~R １２ , R ２１ ~R ２２ , and R ３１ ~R ３２ are each independently a hydrogen atom or an arbitrary substituent, and Ar ２, Ar ３ are each independently an aryl group which may be unsubstituted or substituted with one or more arbitrary substituents. n represents an integer of 1 to 20.

[274] The device according to any one of

[221] to

[255] , wherein the compound represented by formula (1) is a compound represented by the following formula (11):

[0138]

[0139] In formula (11), R １１ , R ２１ ~R ２２ , and R ３１ are each independently a hydrogen atom or an arbitrary substituent, and Ar ２１ ~Ar ２２ , and Ar ３１ ~Ar ３２ are each independently an aryl group which may be unsubstituted or substituted with one or more optional substituents, and n is an integer of 0 to 20.

[0140]

[275] An apparatus comprising: a battery, preferably a rechargeable battery; and a thermal management system for said battery, said thermal management system comprising a heat transfer fluid that exchanges heat with said battery, wherein said heat transfer fluid comprises one or more compounds having the general formula:

[0141]

[0142] In formula (1), Y １ , Y ２ , Y ３ , and Y ４are each independently a hydrogen atom or an arbitrary substituent.

[276] The device according to

[275] , wherein the compound represented by formula (1) contains two or more Si atoms.

[277] The device according to

[275] or

[276] , wherein the compound represented by formula (1) contains one or more O atoms.

[278] The device according to any one of

[275] to

[277] , wherein the compound represented by formula (1) contains Si—O in at least a part of its structure.

[279] The device according to any one of

[275] to

[278] , wherein the compound represented by formula (1) contains Si—O—Si in at least a part of its structure.

[280] The device according to any one of

[275] to

[279] , wherein the compound represented by formula (1) contains O—Si—O in at least a part of its structure.

[281] The device according to any one of

[275] to

[280] , wherein the compound represented by formula (1) contains O—Si—O in at least a part of its structure.

[282] The device according to any one of

[275] to

[281] , wherein the compound represented by formula (1) contains five or fewer F atoms in its structure.

[283] The device according to any one of

[275] to

[282] , wherein the compound represented by formula (1) does not contain F atoms in its structure.

[284] The device according to any one of

[275] to

[283] , wherein the content of the compound represented by formula (1) is at least 5 wt %, preferably more than 50 wt %, and more preferably more than 90 wt %, of the heat transfer fluid.

[285] The device according to any one of

[275] to

[284] , wherein the compound represented by formula (1) has a molecular weight of 100 to 2000.

[286] The device according to any one of

[275] to

[285] , wherein the compound represented by formula (1) has a dynamic viscosity at 25°C of 0.1 cSt to 100 cSt.

[287] The device according to any one of

[275] to

[286] , wherein the compound represented by formula (1) has an absolute viscosity at 25°C of 0.05 mPa s to 200 mPa s.

[288] The compound represented by formula (1) has a density at 25°C of 0.5 g / cm ３ ~2 g / cm ３The device according to any one of

[275] to

[287] , wherein the compound represented by formula (1) has a heat of vaporization of 30 J / g to 300 J / g.

[289] The device according to any one of

[275] to

[288] , wherein the compound represented by formula (1) has a boiling point of 30°C to 500°C.

[290] The device according to any one of

[275] to

[289] , wherein the compound represented by formula (1) has a pour point of -180°C to 0°C.

[291] The device according to any one of

[275] to

[290] , wherein the compound represented by formula (1) has a pour point of -180°C to 0°C.

[292] The device according to any one of

[275] to

[291] , wherein the compound represented by formula (1) has a melting point of -180°C to 0°C.

[293] The device according to any one of

[275] to

[292] , wherein the compound represented by formula (1) has a surface tension of 5 mN / m to 50 mN / m.

[294] The device according to any one of

[275] to

[293] , wherein the compound represented by formula (1) has a vapor pressure of 0 kPa to 100 kPa.

[295] The device according to any one of

[275] to

[294] , wherein the compound represented by formula (1) has a critical temperature of 30°C to 1000°C.

[296] The device according to any one of

[275] to

[295] , wherein the compound represented by formula (1) has a critical pressure of 0.5 MPa to 5 MPa.

[297] The device according to any one of

[275] to

[296] , wherein the compound represented by formula (1) has an expansion coefficient of 0.01 / K or less.

[298] The device according to any one of

[275] to

[297] , wherein the compound represented by formula (1) has a Prandtl number at 40°C of 10 to 100.

[299] The device according to any one of

[275] to

[298] , wherein the compound represented by formula (1) has a thermal conductivity of 0.01 W / m K to 1 W / m K.

[300] The device according to any one of

[275] to

[299] , wherein the compound represented by formula (1) has a heat capacity of 100 J / kg K to 5000 J / kg K.

[301] The device according to any one of

[275] to

[300] , wherein the compound represented by formula (1) has a relative dielectric constant of 1 to 10.

[302] The device according to any one of

[275] to

[300] , wherein the compound represented by formula (1) has a volume resistivity of 1 x 10 ６ Ω m to 1 x 10 １８The device according to any one of

[275] to

[301] , wherein the dielectric strength of the compound represented by formula (1) is 1 kV to 100 kV.

[304] The device according to any one of

[275] to

[303] , wherein the loss of purity of the compound represented by formula (1) is less than 5% when heated at 60°C for 24 hours.

[305] The device according to any one of

[275] to

[304] , wherein the solubility of the compound represented by formula (1) in water at 25°C is 0 ppm to 1000 ppm.

[306] The device according to any one of

[275] to

[305] , wherein the solubility of the compound represented by formula (1) in water at 25°C is 0 ppm to 1000 ppm.

[307] The device according to any one of

[275] to

[306] , wherein the compound represented by formula (1) has a flash point of 30°C or higher.

[308] The device according to any one of

[275] to

[307] , wherein the compound represented by formula (1) has a non-flammability (NFPA) of 0 to 1.

[309] The device according to any one of

[275] to

[308] , wherein the compound represented by formula (1) has a global warming potential of 10 or less.

[310] The device according to any one of

[275] to

[309] , wherein the compound represented by formula (1) is a compound represented by the following formula (2):

[0143]

[0144] In formula (2), R １ , Y ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent.

[311] In the formula (2), R １ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[312] The device according to any one of

[275] to

[311] , wherein the compound represented by formula (1) is a compound represented by the following formula (3):

[0145]

[0146] In formula (3), R １ , R ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent.

[313] In the formula (3), R １ and R ２ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[314] The device according to any one of

[275] to

[311] , wherein the compound represented by formula (1) is a compound represented by the following formula (4):

[0147]

[0148] In formula (4), R １ , R ２ , R ３ , and Y ３ are each independently a hydrogen atom or an arbitrary substituent.

[315] In the formula (4), R １ ~R ３ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[316] The device according to any one of

[275] to

[311] , wherein the compound represented by formula (1) is a compound represented by the following formula (5):

[0149]

[0150] In formula (5), R １ , R ２ , R ３ , and R ４ are each independently a hydrogen atom or an arbitrary substituent. １ is a direct bond, an oxygen atom, or any linking group.

[317] In formula (5), L １

[318] In formula (5), R is a direct bond or an alkylene group having 1 to 5 carbon atoms. １ ~R ４are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 5 carbon atoms or aryl groups having 6 to 20 carbon atoms.

[319] The device according to any one of

[275] to

[311] , wherein the compound represented by formula (1) is a compound represented by the following formula (6):

[0151]

[0152] In formula (6), R １ , R ２ , R ３ , and R ４ are each independently a hydrogen atom or an arbitrary substituent.

[320] The device according to any one of

[275] to

[311] , wherein the compound represented by formula (1) is a compound represented by the following formula (7):

[0153]

[0154] In formula (7), R １ , R ２ , and R ３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[321] The device according to any one of

[275] to

[311] , wherein the compound represented by formula (1) is a compound represented by the following formula (8):

[0155]

[0156] In formula (8), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[322] In formula (8), L１

[323] In formula (8), R is a direct bond or an alkylene group having 1 to 5 carbon atoms. １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３

[324] In formula (8), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３

[325] In formula (8), Ar is an alkyl group having 1 to 5 carbon atoms. １

[326] The device according to any one of

[275] to

[311] , wherein the compound represented by formula (1) is a compound represented by the following formula (9):

[0157]

[0158] In formula (9), R １１ ~R １３ , R ２１ ~R ２２ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and n represents an integer of 0 to 20.

[327] The device according to any one of

[275] to

[311] , wherein the compound represented by formula (1) is a compound represented by the following formula (10):

[0159]

[0160] In formula (10), R １１ ~R １２ , R ２１ ~R ２２ , and R ３１ ~R ３２ are each independently a hydrogen atom or an arbitrary substituent, and Ar ２, Ar ３ are each independently an aryl group which may be unsubstituted or substituted with one or more arbitrary substituents. n represents an integer of 1 to 20.

[328] The device according to any one of

[275] to

[311] , wherein the compound represented by formula (1) is a compound represented by the following formula (11):

[0161]

[0162] In formula (11), R １１ , R ２１ ~R ２２ , and R ３１ are each independently a hydrogen atom or an arbitrary substituent, and Ar ２１ ~Ar ２２ , and Ar ３１ ~Ar ３２ are each independently an aryl group which may be unsubstituted or substituted with one or more optional substituents, and n is an integer of 0 to 20.

[0163]

[329] A heat transfer fluid for exchanging heat between an object and the heat transfer fluid, comprising a compound represented by the following formula (1):

[0164]

[0165] In formula (1), Y １ , Y ２ , Y ３ , and Y ４are each independently a hydrogen atom or an arbitrary substituent.

[330] The heat transfer fluid according to

[329] , wherein the compound represented by formula (1) contains two or more Si atoms.

[331] The heat transfer fluid according to

[329] or

[330] , wherein the compound represented by formula (1) contains one or more O atoms.

[332] The heat transfer fluid according to any one of

[329] to

[331] , wherein the compound represented by formula (1) contains Si—O in at least a part of its structure.

[333] The heat transfer fluid according to any one of

[329] to

[332] , wherein the compound represented by formula (1) contains Si—O—Si in at least a part of its structure.

[334] The heat transfer fluid according to any one of

[329] to

[333] , wherein the compound represented by formula (1) contains O—Si—O in at least a part of its structure.

[335] The heat transfer fluid according to any one of

[329] to

[334] , wherein the compound represented by formula (1) contains an aromatic ring in at least a part of its structure.

[336] The heat transfer fluid according to any one of

[329] to

[335] , wherein the compound represented by formula (1) contains 5 or less F atoms in its structure.

[337] The heat transfer fluid according to any one of

[329] to

[336] , wherein the compound represented by formula (1) does not contain F atoms in its structure.

[338] The heat transfer fluid according to any one of

[329] to

[337] , wherein the content of the compound represented by formula (1) is at least 5 wt %, preferably more than 50 wt %, and more preferably more than 90 wt %, of the heat transfer fluid.

[339] The heat transfer fluid according to any one of

[329] to

[338] , wherein the compound represented by formula (1) has a molecular weight of 100 to 2000.

[340] The heat transfer fluid according to any one of

[329] to

[339] , wherein the compound represented by formula (1) has a dynamic viscosity at 25°C of 0.1 cSt to 100 cSt.

[341] The heat transfer fluid according to any one of

[329] to

[340] , wherein the compound represented by formula (1) has an absolute viscosity at 25°C of 0.05 mPa s to 200 mPa s.

[342] The compound represented by formula (1) has a density at 25°C of 0.5 g / cm ３ ~2 g / cm ３The heat transfer fluid according to any one of

[329] to

[341] , wherein the compound represented by formula (1) has a heat of vaporization of 30 J / g to 300 J / g.

[344] The heat transfer fluid according to any one of

[329] to

[343] , wherein the compound represented by formula (1) has a boiling point of 30°C to 500°C.

[345] The heat transfer fluid according to any one of

[329] to

[344] , wherein the compound represented by formula (1) has a pour point of -180°C to 0°C.

[346] The heat transfer fluid according to any one of

[329] to

[345] , wherein the compound represented by formula (1) has a melting point of -180°C to 0°C.

[347] The heat transfer fluid according to any one of

[329] to

[346] , wherein the compound represented by formula (1) has a surface tension of 5 mN / m to 50 mN / m.

[348] The heat transfer fluid according to any one of

[329] to

[347] , wherein the compound represented by formula (1) has a vapor pressure of 0 kPa to 100 kPa.

[349] The heat transfer fluid according to any one of

[329] to

[348] , wherein the compound represented by formula (1) has a critical temperature of 30°C to 1000°C.

[350] The heat transfer fluid according to any one of

[329] to

[349] , wherein the compound represented by formula (1) has a critical pressure of 0.5 MPa to 5 MPa.

[351] The heat transfer fluid according to any one of

[329] to

[350] , wherein the compound represented by formula (1) has an expansion coefficient of 0.01 / K or less.

[352] The heat transfer fluid according to any one of

[329] to

[351] , wherein the compound represented by formula (1) has a Prandtl number at 40°C of 10 to 100.

[353] The heat transfer fluid according to any one of

[329] to

[352] , wherein the compound represented by formula (1) has a thermal conductivity of 0.01 W / m K to 1 W / m K.

[354] The heat transfer fluid according to any one of

[329] to

[353] , wherein the compound represented by formula (1) has a heat capacity of 100 J / kg K to 5000 J / kg K.

[355] The heat transfer fluid according to any one of

[329] to

[354] , wherein the compound represented by formula (1) has a relative dielectric constant of 1 to 10.

[356] The compound represented by formula (1) has a volume resistivity of 1 x 10 ６ Ω m to 1 x 10 １８The heat transfer fluid according to any one of

[329] to

[355] , wherein the dielectric strength of the compound represented by formula (1) is 1 kV to 100 kV.

[357] The heat transfer fluid according to any one of

[329] to

[356] , wherein the compound represented by formula (1) has a dielectric strength of 1 kV to 100 kV.

[358] The heat transfer fluid according to any one of

[329] to

[357] , wherein the compound represented by formula (1) loses less than 5% purity when heated at 60°C for 24 hours.

[359] The heat transfer fluid according to any one of

[329] to

[358] , wherein the compound represented by formula (1) has a water solubility of 0 ppm to 1000 ppm at 25°C.

[360] The heat transfer fluid according to any one of

[329] to

[359] , wherein the compound represented by formula (1) has a water solubility of 0 ppm to 1000 ppm at 25°C.

[361] The heat transfer fluid according to any one of

[329] to

[360] , wherein the compound represented by formula (1) has a flash point of 30°C or higher.

[362] The heat transfer fluid according to any one of

[329] to

[361] , wherein the compound represented by formula (1) has a non-flammable property (NFPA) of 0 to 1.

[363] The heat transfer fluid according to any one of

[329] to

[362] , wherein the compound represented by formula (1) has a global warming potential of 10 or less.

[364] The heat transfer fluid according to any one of

[329] to

[363] , wherein the object is at least one selected from the group consisting of electronic computing equipment, microprocessors, semiconductor wafers used to manufacture semiconductor devices, power control semiconductors, electrochemical cells (including lithium ion batteries), power distribution switchgear, power transformers, circuit boards, multi-chip modules, packaged or unpackaged semiconductor devices, fuel cells, and lasers.

[365] The heat transfer fluid of any one of

[329] to

[364] , wherein the object is an electronic computing device, the electronic computing device including one or more electronic circuit boards, and the method comprises directly contacting the electronic circuit boards with the heat transfer fluid.

[366] The heat transfer fluid of any one of

[329] to

[365] , wherein the heat transfer fluid is a method of single-phase immersion cooling or two-phase immersion cooling.

[367] The heat transfer fluid according to any one of

[329] to

[366] , which is used in a system for cooling a device selected from the group consisting of a system for cooling a wafer chuck in an etcher, an asher, a stepper, or a PECVD apparatus, a system for controlling the temperature in a test head for a die performance test, a temperature control system in a semiconductor process facility, a thermal shock test of an electronic device, and a system for maintaining a constant temperature of an electronic device.

[368] The heat transfer fluid according to any one of

[329] to

[367] , wherein the compound represented by formula (1) is a compound represented by the following formula (2):

[0166]

[0167] In formula (2), R １ , Y ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent.

[369] In the formula (2), R １ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[370] The heat transfer fluid according to any one of

[329] to

[367] , wherein the compound represented by formula (1) is a compound represented by the following formula (3):

[0168]

[0169] In formula (3), R １ , R ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent.

[371] In the formula (3), R １ and R ２ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[372] The heat transfer fluid according to any one of

[329] to

[367] , wherein the compound represented by formula (1) is a compound represented by the following formula (4):

[0170]

[0171] In formula (4), R １ , R ２ , R ３ , and Y ３ are each independently a hydrogen atom or an arbitrary substituent.

[373] In the formula (4), R １ ~R ３ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms.

[374] The heat transfer fluid according to any one of

[329] to

[367] , wherein the compound represented by formula (1) is a compound represented by the following formula (5):

[0172]

[0173] In formula (5), R １ , R ２ , R ３ , and R ４ are each independently a hydrogen atom or an arbitrary substituent. １ is a direct bond, an oxygen atom, or any linking group.

[375] In formula (5), L １

[376] In the formula (5), R is a direct bond or an alkylene group having 1 to 5 carbon atoms. １ ~R ４ are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a silyl group optionally substituted with one or more alkyl groups having 1 to 5 carbon atoms or aryl groups having 6 to 20 carbon atoms.

[377] The heat transfer fluid according to any one of

[329] to

[367] , wherein the compound represented by formula (1) is a compound represented by the following formula (6):

[0174]

[0175] In formula (6), R １ , R ２ , R ３ , and R ４

[378] The heat transfer fluid according to any one of

[329] to

[367] , wherein the compound represented by formula (1) is a compound represented by the following formula (7):

[0176]

[0177] In formula (7), R １ , R ２ , and R ３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[379] The heat transfer fluid according to any one of

[329] to

[367] , wherein the compound represented by formula (1) is a compound represented by the following formula (8):

[0178]

[0179] In formula (8), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[380] In formula (8), L １

[381] In the formula (8), R is a direct bond or an alkylene group having 1 to 5 carbon atoms. １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３

[382] In formula (8), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１~R ３３

[383] In the formula (8), Ar is an alkyl group having 1 to 5 carbon atoms. １

[384] The heat transfer fluid according to any one of

[329] to

[367] , wherein the compound represented by formula (1) is a compound represented by the following formula (9):

[0180]

[0181] In formula (9), R １１ ~R １３ , R ２１ ~R ２２ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and n represents an integer of 0 to 20.

[385] The heat transfer fluid according to any one of

[329] to

[367] , wherein the compound represented by formula (1) is a compound represented by the following formula (10):

[0182]

[0183] In formula (10), R １１ ~R １２ , R ２１ ~R ２２ , and R ３１ ~R ３２ are each independently a hydrogen atom or an arbitrary substituent, and Ar ２ , Ar ３ are each independently an aryl group which may be unsubstituted or substituted with one or more arbitrary substituents. n represents an integer of 1 to 20.

[386] The heat transfer fluid according to any one of

[329] to

[367] , wherein the compound represented by formula (1) is a compound represented by the following formula (11):

[0184]

[0185] In formula (11), R １１ , R ２１ ~R ２２ , and R ３１are each independently a hydrogen atom or an arbitrary substituent, and Ar ２１ ~Ar ２２ , and Ar ３１ ~Ar ３２ are each independently an aryl group which may be unsubstituted or substituted with one or more optional substituents, and n is an integer of 0 to 20.

[0186] According to the present disclosure, it is possible to provide a heat transfer fluid that is thermally stable over a wide temperature range, suitable for various uses, and has a short atmospheric lifetime that reduces the global warming potential.

[0187] In the following description, it is to be understood that other embodiments are contemplated and may be made without departing from the scope or spirit of the present disclosure. Accordingly, the following detailed description is not to be taken in a limiting sense.

[0188] Unless otherwise specified, all numbers expressing sizes, quantities, and physical properties of structures used in the specification and appended claims are to be understood as being modified in each instance by the word "about." Thus, unless otherwise indicated, the numerical parameters set forth in the foregoing specification and appended claims are approximations that may vary depending upon the desired properties targeted by one of ordinary skill in the art using the teachings disclosed herein. The use of numerical ranges by endpoints includes all numbers within that range (e.g., 1 to 5 includes 1, 1.5, 2, 2.75, 3, 3.80, 4, and 5) and any range within that range.

[0189] In this disclosure, "device" means an object or apparatus that is heated, cooled, or maintained at a predetermined temperature. "Inert" means a chemical composition that generally does not chemically react under normal conditions of use. "Mechanism" means a piece of system or machinery.

[0190] <Heat Transfer Fluid> One aspect of the present disclosure relates to a heat transfer fluid containing a compound represented by formula (A), wherein the number of Si atoms in formula (A) is 1, and wherein the total mass of the compound represented by formula (A) in the heat transfer fluid is 5 mass%. Another aspect of the present disclosure relates to a heat transfer fluid containing a compound represented by formula (B). Another aspect of the present disclosure relates to a heat transfer fluid containing a compound represented by formula (C), wherein the number of Si atoms in formula (C) is 4. Another aspect of the present disclosure relates to a heat transfer fluid containing a compound represented by formula (D). Another aspect of the present disclosure relates to a heat transfer fluid containing a compound represented by formula (D1). The compounds represented by formulas (A) to (D) and formula (D1) are described in detail below.

[0191] [Compound represented by formula (A)]

[0192]

[0193] In formula (A), Y ５ , Y ６ , Y ７ , and Y ８ each independently represents a group containing 1 to 20 carbon atoms, a hydrogen atom, or a halogen. Since the number of Si atoms in the compound represented by formula (A) is 1, Y ５ , Y ６ , Y ７ , and Y ８ does not contain Si atoms.

[0194] In formula (A), Y ５ , Y ６ , Y ７ , and Y ８each independently represents a group containing 1 to 20 carbon atoms, a hydrogen atom, or a halogen atom, and examples thereof include alkyl groups having 1 to 20 carbon atoms (e.g., a methyl group, an ethyl group, an isopropyl group, etc.), alkenyl groups having 2 to 20 carbon atoms (e.g., an ethenyl group, a 2-propenyl group, a 4-butenyl group, etc.), alkynyl groups having 2 to 20 carbon atoms (e.g., an ethynyl group, a 2-methyl-3-butyn-2-yl group, etc.), cycloalkyl groups having 3 to 20 carbon atoms (e.g., a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc.), cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms (e.g., a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 4-phenylphenyl group, etc.), heteroaryl groups having 3 to 20 carbon atoms (e.g., a 2-furyl group), , 2-thiophenyl group, 2-pyridyl group, 3-imidazolyl group, etc.), alkoxy groups having 1 to 20 carbon atoms (e.g., methoxy group, ethoxy group, isopropoxy group, etc.), cycloalkylalkyl groups having 4 to 20 carbon atoms (e.g., cyclopropylmethyl group, cyclopentylmethyl group, cyclohexylmethyl group, etc.), arylalkyl groups having 7 to 20 carbon atoms (e.g., phenylmethyl group), heteroarylalkyl groups having 4 to 20 carbon atoms, alkoxyalkyl groups having 2 to 20 carbon atoms, hydrogen atoms, or halogens (chlorine, fluorine, bromine, etc.). Among these, alkyl groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, and arylalkyl groups having 7 to 20 carbon atoms are preferred because they are stable to oxygen and moisture. Some of the carbon atoms may be substituted with O, CO, COO, CONH, OCONH, N, N═N, etc. Here, the nitrogen atom may be substituted with a hydrogen atom or any of the above-mentioned substituents. Some of the hydrogen atoms may be substituted with any substituent. Examples of groups in which some of the hydrogen atoms have been substituted include substituted alkyl groups such as a chloromethyl group and a 2,2,2-trichloroethyl group; substituted aryl groups such as a 4-methylphenyl group, a 4-methoxyphenyl group and a 4-chlorophenyl group; and substituted arylalkyl groups such as a 4-methylphenylmethyl group and a 4-methoxyphenylethyl group.

[0195] Y ５ , Y ６ , Y ７ , and Y ８As the alkyl group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a substituted alkyl group having 1 to 20 carbon atoms, a substituted alkoxy group having 1 to 20 carbon atoms, a substituted aryl group having 6 to 20 carbon atoms, a substituted arylalkyl group having 7 to 20 carbon atoms, and a halogen (chlorine, fluorine, bromine, etc.) are preferred, as they are stable against oxygen and moisture, and an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms is more preferred.

[0196] The alkyl group having 1 to 20 carbon atoms is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms, still more preferably an alkyl group having 1 to 4 carbon atoms, and particularly preferably methyl or ethyl. The alkyl group may be a linear alkyl group or a branched alkyl group.

[0197] The alkoxy group having 1 to 20 carbon atoms is preferably an alkoxy group having 1 to 10 carbon atoms, more preferably an alkoxy group having 1 to 8 carbon atoms, still more preferably an alkoxy group having 1 to 4 carbon atoms, and particularly preferably methoxy or ethoxy. The alkoxy group may be a linear alkoxy group or a branched alkoxy group.

[0198] As the aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms is preferable, an aryl group having 6 to 10 carbon atoms is more preferable, and a phenyl group is even more preferable.

[0199] The arylalkyl group having 7 to 20 carbon atoms is preferably an arylalkyl group having 7 to 20 carbon atoms, more preferably an arylalkyl group having 7 to 10 carbon atoms, further preferably benzyl or phenethyl, and particularly preferably phenethyl.

[0200] In order to improve the stability of the compound and reduce its hydrophilicity, Y ５ , Y ６ , Y ７ , and Y ８ is preferably composed of only carbon atoms, hydrogen atoms, and oxygen atoms.

[0201] Y５ , Y ６ , Y ７ , and Y ８ may be the same or different. In order to reduce the crystallinity and become liquid at low temperatures, it is preferable that the number of types is two or more, more preferably three or more, and even more preferably four. On the other hand, from the viewpoint of inexpensive production, it is preferable that the number of types is two or less, and more preferably the same. ５ , Y ６ , Y ７ , and Y ８ may be bonded to each other to form a ring structure. When a ring structure is formed, a hydrogen atom in any of the above-mentioned substituents is substituted with another arbitrary substituent. Here, the ring structure may be a 6-membered ring, an 8-membered ring, or a 10-membered ring consisting of only carbon atoms, or a carbon atom and an oxygen atom.

[0202] The compound represented by the formula (A) has a Si atom, which has a lower electronegativity than a carbon atom, and is therefore thought to have a tendency to have excellent heat resistance, cold resistance, light resistance, and weather resistance, making it suitable as a heat transfer fluid used to exchange heat with an object.

[0203] The total mass of the compounds represented by formula (A) in the heat transfer fluid is 5% by mass or more, may be 10% by mass or more, 15% by mass or more, or 20% by mass or more. It may also be 100% by mass or less, 95% by mass or less, 90% by mass or less, or 85% by mass or more. The above upper and lower limits can be combined arbitrarily. For example, it may be 5 to 100% by mass, 10 to 95% by mass, 15 to 90% by mass, or 20 to 85% by mass.

[0204] The compound represented by formula (A) preferably includes any of the compounds represented by the following formulae (Aa) to (Ae).

[0205]

[0206] In formulas (Aa) to (Ae), R Ａ１ ~R Ａ２０each independently represents a group containing 1 to 10 carbon atoms. The compounds represented by formulas (Aa) to (Ae) have at least one of an Si—C bond, an Si—O bond, and an Si—N bond, which have higher bond energy than a C—C bond, an Si—Si bond, or a C—O bond, and therefore can contribute to improving the heat resistance, cold resistance, light resistance, weather resistance, and fluidity of the heat transfer fluid.

[0207] In formulas (Aa) to (Ae), R Ａ１ ~R Ａ２０ each independently represents a group containing 1 to 10 carbon atoms, such as an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, a cycloalkynyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, a heteroaryl group having 3 to 10 carbon atoms, a cycloalkylalkyl group having 4 to 10 carbon atoms, an arylalkyl group having 7 to 10 carbon atoms, a heteroarylalkyl group having 4 to 10 carbon atoms, and an alkoxyalkyl group having 2 to 10 carbon atoms. Of these, preferred are an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an arylalkyl group having 7 to 10 carbon atoms. Some of the carbon atoms may be substituted with O, CO, COO, CONH, OCONH, N, N═N, or the like. Here, the nitrogen atom may be substituted with a hydrogen atom or any of the above-mentioned substituents. Some of the hydrogen atoms may be substituted with any substituent. Examples of groups in which some of the hydrogen atoms have been substituted include substituted alkyl groups such as a chloromethyl group and a 2,2,2-trichloroethyl group; substituted aryl groups such as a 4-methylphenyl group, a 4-methoxyphenyl group and a 4-chlorophenyl group; and substituted arylalkyl groups such as a 4-methylphenylmethyl group and a 4-methoxyphenylethyl group.

[0208] R Ａ１ ~R Ａ２０ Among these, in formulae (Aa) to (Ae), the group that is not bonded to an oxygen atom is preferably an alkyl group, an aryl group, an arylalkyl group, a substituted alkyl group, a substituted aryl group, or a substituted arylalkyl group, more preferably an alkyl group or an arylalkyl group.

[0209] The alkyl group is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, further preferably methyl or ethyl, and particularly preferably methyl. The alkyl group may be a linear alkyl group or a branched alkyl group.

[0210] The arylalkyl group is preferably benzyl or phenethyl, more preferably phenethyl.

[0211] R Ａ１ ~R Ａ２０ Among these, the group bonded to the oxygen atom in formulae (Aa) to (Ae) is preferably an alkyl group, an aryl group, an arylalkyl group, a substituted alkyl group, a substituted aryl group, or a substituted arylalkyl group, more preferably an alkyl group or a substituted alkyl group, and even more preferably an alkyl group.

[0212] The alkyl group is more preferably an alkyl group having 1 to 8 carbon atoms, still more preferably an alkyl group having 1 to 4 carbon atoms, and particularly preferably methoxy or ethoxy. The alkoxy group may be a linear alkoxy group or a branched alkoxy group.

[0213] R Ａ１ ~R Ａ２０ In another embodiment, each of R may independently represent any group selected from the group consisting of a methyl group, an ethyl group, a propyl group, a vinyl group, a propynyl group, a butyl group, and a phenyl group. Ａ１ ~R Ａ２０ In another embodiment, each of the groups may independently represent any group selected from the group consisting of a methyl group, an ethyl group, and a phenethyl group, or may represent an ethyl group.

[0214] Examples of the compound represented by formula (A) include the following compounds: Ph-(CH ２ ) ２ -Si(OMe) ３ Si(OEt) ４ In the formula, Ph represents phenyl, Me represents methyl, and Et represents ethyl.

[0215] [Compound represented by formula (B)]

[0216]

[0217] In formula (B), n represents an integer of 0 to 2. ６１ ~R ６３ , R ７１ ~R ７２ , and R ８１ ~R ８３ are each independently an optional substituent, provided that R ６１ ~R ６３ , R ７１ ~R ７２ , and R ８１ ~R ８３ At least one of the groups is a group containing 2 to 20 carbon atoms. The compound represented by formula (B) has at least two Si—O bonds, which have higher bond energy than C—C bonds, Si—Si bonds, and C—O bonds, and can therefore contribute to improving the heat resistance, cold resistance, light resistance, weather resistance, and fluidity of the heat transfer fluid.

[0218] In formula (B), R ６１ ~R ６３ , R ７１ ~R ７２ , and R ８１ ~R ８３ Each independently represents an arbitrary substituent. For example, Y ５ , Y ６ , Y ７ , and Y ８ The same groups as those shown in the above can be mentioned. ６１ ~R ６３ , R ７１ ~R ７２ , and R ８１ ~R ８３ At least one of R is a group containing 2 to 20 carbon atoms; ６１ ~R ６３ , R ７１ ~R ７２ , and R ８１ ~R ８３ The group having 2 to 20 carbon atoms represented by at least one of the following is preferably an ethyl group or a phenyl group.

[0219] Since it tends to have both a low melting point and low viscosity, ６１ ~R ６３ , R ７１~R ７２ , and R ８１ ~R ８３ is preferably an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a substituted alkyl group having 1 to 20 carbon atoms, a substituted alkenyl group having 2 to 20 carbon atoms, a substituted alkoxy group having 1 to 20 carbon atoms, a substituted aryl group having 6 to 20 carbon atoms, or a substituted arylalkyl group having 7 to 20 carbon atoms, and more preferably an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

[0220] The alkyl group having 1 to 20 carbon atoms is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms, still more preferably an alkyl group having 1 to 4 carbon atoms, particularly preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group or an ethyl group. The alkyl group may be a linear alkyl group or a branched alkyl group.

[0221] The alkenyl group having 2 to 20 carbon atoms is preferably an alkenyl group having 2 to 10 carbon atoms, more preferably an alkenyl group having 2 to 8 carbon atoms, still more preferably an alkenyl group having 2 to 4 carbon atoms, and particularly preferably a vinyl group or a propenyl group. The alkenyl group may be a linear alkenyl group or a branched alkenyl group.

[0222] The aryl group having 6 to 20 carbon atoms is preferably an aryl group having 6 to 10 carbon atoms, more preferably a phenyl group or a naphthyl group, and even more preferably a phenyl group.

[0223] R ６１ ~R ６３ , R ７１ ~R ７２ , and R ８１ ~R ８３ In another embodiment, each of R may independently represent any group selected from the group consisting of a methyl group, an ethyl group, a propyl group, a vinyl group, a propynyl group, a butyl group, and a phenyl group. ６１ ~R ６３ , R ７１ ~R７２ , and R ８１ ~R ８３ In another embodiment, each of the groups may independently be any group selected from the group consisting of a methyl group, an ethyl group, and a phenyl group, or may be an ethyl group.

[0224] Examples of compounds represented by formula (B) include the following compounds: Ph-Si(Me) ２ —O—Si(Me) ２ -Ph Ph-Si(Me) ２ -(O-Si(Me) ２ ) ２ -Ph Ph-Si(Me) ２ -(O-Si(Me) ２ ) ３ -Ph Ph ２ MeSi-O-Si(Me) ２ -O-SiMePh ２ PhMe ２ Si-O-Si(Ph) ２ —O—SiMe ２ Ph TES-O-TES Oct-Si(Me) ２ -Si(Me) ２ -Oct ClCH ２ -Si(Me) ２ —O—Si(Me) ２ -CH ２ Cl TMS-O-Si(Me) ２ - (CH ２ ) ２ -Si(Me) ３ --O-TMS In the formula, Ph represents phenyl, Me represents methyl, TES represents triethylsilyl, Oct represents n-octyl, and TMS represents trimethylsilyl.

[0225] The total mass of the compounds represented by formula (B) in the heat transfer fluid is 5% by mass or more, may be 10% by mass or more, 15% by mass or more, or 20% by mass or more. It may also be 100% by mass or less, 95% by mass or less, 90% by mass or less, or 85% by mass or more. The above upper and lower limits can be combined arbitrarily. For example, it may be 5 to 100% by mass, 10 to 95% by mass, 15 to 90% by mass, or 20 to 85% by mass.

[0226] [Compound represented by formula (C)]

[0227]

[0228] In formula (C), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ each independently represents a group containing 1 to 20 carbon atoms, R ４１ represents a group containing 2 to 20 carbon atoms. Since the number of Si atoms in the compound represented by formula (C) is 4, R １１ ~R １３ , R ２１ ~R ２３ , R ３１ ~R ３３ , and R ４１ does not contain Si atoms.

[0229] In formula (C), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ Each independently represents a group containing 1 to 20 carbon atoms. For example, Y ５ , Y ６ , Y ７ , and Y ８ In formula (C), R ４１ represents a group containing 2 to 20 carbon atoms. For example, Y in formula (A) ５ , Y ６ , Y ７ , and Y ８The compound represented by formula (C) has six Si—O bonds, which have higher bond energy than C—C bonds, Si—Si bonds, and C—O bonds, and therefore can contribute to improving the heat resistance, cold resistance, light resistance, weather resistance, and flowability of the heat transfer fluid.

[0230] R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ is preferably an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a substituted alkyl group having 1 to 20 carbon atoms, a substituted alkenyl group having 2 to 20 carbon atoms, a substituted aryl group having 6 to 20 carbon atoms, or a substituted arylalkyl group having 7 to 20 carbon atoms, more preferably an alkyl group having 1 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms, and even more preferably an alkyl group having 1 to 20 carbon atoms.

[0231] The alkyl group having 1 to 20 carbon atoms is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms, still more preferably an alkyl group having 1 to 4 carbon atoms, particularly preferably methyl or ethyl, and particularly preferably methyl. The alkyl group may be a linear alkyl group or a branched alkyl group.

[0232] The arylalkyl group having 7 to 20 carbon atoms is preferably an arylalkyl group having 7 to 20 carbon atoms, more preferably an arylalkyl group having 7 to 10 carbon atoms, and further preferably benzyl or phenethyl.

[0233] R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ may be methyl.

[0234] R ４１is preferably an alkyl group having 2 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a substituted alkyl group having 2 to 20 carbon atoms, a substituted alkenyl group having 2 to 20 carbon atoms, a substituted alkoxy group having 2 to 20 carbon atoms, a substituted aryl group having 6 to 20 carbon atoms, or a substituted arylalkyl group having 7 to 20 carbon atoms, more preferably an alkyl group having 2 to 20 carbon atoms, a substituted alkyl group having 2 to 20 carbon atoms, an alkoxy group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a substituted aryl group having 6 to 20 carbon atoms, or a substituted arylalkyl group having 7 to 20 carbon atoms, and even more preferably an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a substituted aryl group having 6 to 20 carbon atoms, or a substituted arylalkyl group having 7 to 20 carbon atoms.

[0235] From the viewpoint of increasing flame retardancy, R ４１ More preferably, R has an aromatic ring. ４１ Examples of such groups include aryl groups having 6 to 20 carbon atoms, substituted aryl groups having 6 to 20 carbon atoms, arylalkyl groups having 7 to 20 carbon atoms, substituted arylalkyl groups having 7 to 20 carbon atoms, substituted alkenyl groups having 7 to 20 carbon atoms and having an aromatic ring as a substituent, and substituted alkoxy groups having 2 to 20 carbon atoms and having an aromatic ring as a substituent. Preferred are aryl groups having 6 to 10 carbon atoms, substituted aryl groups having 6 to 10 carbon atoms, arylalkyl groups having 7 to 10 carbon atoms, and substituted arylalkyl groups having 7 to 10 carbon atoms, because they tend to have low viscosity.

[0236] As the aryl group having 6 to 20 carbon atoms and the substituted aryl group having 6 to 20 carbon atoms, an optionally substituted aryl group having 6 to 10 carbon atoms is preferred, an optionally substituted phenyl or an optionally substituted naphthyl is more preferred, and an optionally substituted phenyl is even more preferred. As the substituents permitted for these groups, an alkyl group having 1 to 20 carbon atoms and an alkoxy group having 1 to 20 carbon atoms are preferred, an alkyl group having 1 to 10 carbon atoms and an alkoxy group having 1 to 10 carbon atoms are more preferred, an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms are even more preferred, and methyl, ethyl, methoxy, and ethoxy are even more preferred, with methyl and methoxy being particularly preferred.

[0237] As the arylalkyl group having 7 to 20 carbon atoms and the substituted arylalkyl group having 7 to 20 carbon atoms, an optionally substituted arylalkyl group having 7 to 14 carbon atoms is more preferred, an optionally substituted arylalkyl group having 7 to 10 carbon atoms is even more preferred, optionally substituted benzyl and optionally substituted phenethyl are particularly preferred, and optionally substituted phenethyl is particularly preferred. As the substituents permitted for these groups, an alkyl group having 1 to 20 carbon atoms and an alkoxy group having 1 to 20 carbon atoms are preferred, an alkyl group having 1 to 10 carbon atoms and an alkoxy group having 1 to 10 carbon atoms are more preferred, an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms are even more preferred, and methyl, ethyl, methoxy, and ethoxy are even more preferred, with methyl and methoxy being particularly preferred.

[0238] As the alkyl group having 2 to 20 carbon atoms and the substituted alkyl group having 2 to 20 carbon atoms, an optionally substituted alkyl group having 2 to 12 carbon atoms is more preferred, an optionally substituted alkyl group having 2 to 8 carbon atoms is even more preferred, and optionally substituted ethyl, propyl, and butyl are particularly preferred. The alkyl group may be a linear alkyl group or a branched alkyl group. Preferred substituents for these groups are an amide group having 1 to 20 carbon atoms, an ester group having 2 to 20 carbon atoms, and an amino group.

[0239] Examples of compounds represented by formula (C) include the following compounds: Ph-Si(OTMS)３ Ph-(CH ２ ) ２ -Si(OTMS) ３ (4-MePh)-Si(OTMS) ３ (4-MeOPh)-Si(OTMS) ３ (4-MePh)-CH ２ -Si(OTMS) ３ In the formula, Ph represents phenyl, OTMS represents trimethylsiloxy, 4-MePh represents 4-methylphenyl, and 4-MeOPh represents 4-methoxyphenyl.

[0240] The structure of the above compound is shown below.

[0241]

[0242] The total mass of the compound represented by formula (C) in the heat transfer fluid may be 51% by mass or more, 55% by mass or more, or 60% by mass or more. It may also be 100% by mass or less, 95% by mass or less, or 90% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, it may be 51 to 100% by mass, 55 to 95% by mass, or 60 to 90% by mass.

[0243] [Compound represented by formula (D)]

[0244]

[0245] In formula (D), n represents an integer of 2 to 5. Each R independently represents a group containing 1 to 20 carbon atoms, provided that at least one R represents a group containing 2 to 20 carbon atoms.

[0246] In formula (D), each R independently represents a group containing 1 to 20 carbon atoms. ５ , Y ６ , Y ７ , and Y ８ In formula (D), R each independently represents a group containing 1 to 20 carbon atoms, and at least one of them represents a group containing 2 to 20 carbon atoms. For example, Y in formula (A) ５ , Y６ , Y ７ , and Y ８ The compound represented by formula (D) has at least four Si—O bonds, which have higher bond energy than C—C bonds, Si—Si bonds, and C—O bonds, and therefore can contribute to improving the heat resistance, cold resistance, light resistance, weather resistance, and flowability of the heat transfer fluid.

[0247] Because they are stable against oxygen and moisture, R is preferably an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, a substituted alkyl group having 1 to 20 carbon atoms, or a substituted alkenyl group having 2 to 20 carbon atoms, and more preferably an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms. For at least one of R representing a group containing 2 to 20 carbon atoms, an alkyl group having 2 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, a substituted alkyl group having 2 to 20 carbon atoms, or a substituted alkenyl group having 2 to 20 carbon atoms is preferred, and an alkyl group having 2 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms is more preferred.

[0248] As an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms is preferred because of its low viscosity, an alkyl group having 1 to 8 carbon atoms is more preferred, an alkyl group having 1 to 5 carbon atoms is even more preferred, a methyl group and an ethyl group are particularly preferred, and a methyl group is particularly preferred. As an alkyl group having 2 to 20 carbon atoms, an alkyl group having 2 to 10 carbon atoms is preferred because of its low viscosity, an alkyl group having 2 to 8 carbon atoms is more preferred, an alkyl group having 2 to 5 carbon atoms is even more preferred, an ethyl group, a propyl group and a butyl group are particularly preferred, and an ethyl group is particularly preferred. The alkyl group may be a linear alkyl group or a branched alkyl group.

[0249] The alkenyl group having 2 to 20 carbon atoms is preferably an alkenyl group having 2 to 10 carbon atoms, more preferably an alkenyl group having 2 to 8 carbon atoms, even more preferably an alkenyl group having 2 to 5 carbon atoms, particularly preferably a vinyl group, a propenyl group, or a butenyl group, and particularly preferably a vinyl group. The alkenyl group may be a linear alkenyl group or a branched alkenyl group.

[0250] In one embodiment, R is an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and at least one of the R is an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms. In another embodiment, at least one R is an alkyl group having 2 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, and the remaining R are methyl groups. In another embodiment, at least one R is a vinyl group, and the remaining R are methyl groups.

[0251] In formula (D), n represents an integer of 2 to 5, preferably 3 or 4, and more preferably 3.

[0252] Examples of the compound represented by formula (D) include the following compounds.

[0253]

[0254] The total mass of the compounds represented by formula (D) in the heat transfer fluid is 5% by mass or more, may be 10% by mass or more, 15% by mass or more, or 20% by mass or more. It may also be 100% by mass or less, 95% by mass or less, 90% by mass or less, or 85% by mass or more. The above upper and lower limits can be combined arbitrarily. For example, it may be 5 to 100% by mass, 10 to 95% by mass, 15 to 90% by mass, or 20 to 85% by mass.

[0255] [Compound Represented by Formula (D1)] The compound represented by formula (D) may contain the following formula (D1).

[0256]

[0257] In formula (D1), n ​​represents an integer of 2 to 5. Ｄ１ each independently represents a group containing 1 to 20 carbon atoms; R Ｄ２ Each independently represents a group containing 2 to 20 carbon atoms. Ｄ１ and / or R Ｄ２ may be different for each unit or may be the same, but from the viewpoint of production, it is preferable that they are the same.

[0258] In formula (D1), R Ｄ１ Each independently represents a group containing 1 to 20 carbon atoms. For example, Y ５ , Y ６ , Y ７ , and Y ８ In formula (D), R Ｄ２ Each independently represents a group containing 2 to 20 carbon atoms. For example, Y in formula (A) ５ , Y ６ , Y ７ , and Y ８ Examples of the groups include those obtained by excluding groups containing only one carbon atom from the groups represented by the formula:

[0259] R Ｄ１ R is preferably an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, a substituted alkyl group having 1 to 20 carbon atoms, or a substituted alkenyl group having 2 to 20 carbon atoms, and more preferably an alkyl group having 1 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms. Ｄ２ is preferably an alkyl group having 2 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, a substituted alkyl group having 2 to 20 carbon atoms, or a substituted alkenyl group having 2 to 20 carbon atoms, and more preferably an alkyl group having 2 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms.

[0260] As the alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms is preferred, an alkyl group having 1 to 8 carbon atoms is more preferred, an alkyl group having 1 to 5 carbon atoms is even more preferred, a methyl group and an ethyl group are particularly preferred, and a methyl group is particularly preferred. As the alkyl group having 2 to 20 carbon atoms, an alkyl group having 2 to 10 carbon atoms is preferred, an alkyl group having 2 to 8 carbon atoms is more preferred, an alkyl group having 2 to 5 carbon atoms is even more preferred, an ethyl group, a propyl group and a butyl group are particularly preferred, and an ethyl group is particularly preferred. The alkyl group may be a linear alkyl group or a branched alkyl group.

[0261] The alkenyl group having 2 to 20 carbon atoms is preferably an alkenyl group having 2 to 10 carbon atoms, more preferably an alkenyl group having 2 to 8 carbon atoms, even more preferably an alkenyl group having 2 to 5 carbon atoms, particularly preferably a vinyl group, a propenyl group, or a butenyl group, and particularly preferably a vinyl group. The alkenyl group may be a linear alkenyl group or a branched alkenyl group.

[0262] In one embodiment, R Ｄ１ is an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R Ｄ２ is an alkyl group having 2 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms. Ｄ１ is a methyl group, and R Ｄ２ is an alkyl group having 2 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms. Ｄ１ is a methyl group, and R Ｄ２ is a vinyl group.

[0263] In formula (D1), n ​​represents an integer of 2 to 5, preferably 3 or 4, and more preferably 3.

[0264] Examples of the compound represented by formula (D1) include the compounds exemplified as the compound represented by formula (D).

[0265] The total mass of the compounds represented by formula (D1) in the heat transfer fluid is 5% by mass or more, may be 10% by mass or more, 15% by mass or more, or 20% by mass or more. It may also be 100% by mass or less, 95% by mass or less, 90% by mass or less, or 85% by mass or more. The above upper and lower limits can be combined arbitrarily. For example, it may be 5 to 100% by mass, 10 to 95% by mass, 15 to 90% by mass, or 20 to 85% by mass.

[0266] The compounds represented by formulas (A) to (D) and (D1), as well as the compounds represented by formula (1) described below, may be commercially available compounds. Furthermore, the compounds represented by formulas (A) to (D) and (D1), as well as the compounds represented by formula (1) described below, may be prepared by known methods. For example, they can be prepared by the methods described in U.S. Patent No. 6,943,264 and Japanese Patent No. 4,475,402.

[0267] The heat transfer fluid may contain typical additives used in heat transfer fluids in addition to the compounds represented by Formulae (A) to (D) and (D1) and the following Formula (1) described below. Examples of additives include acid scavengers, flame retardants, antifoaming agents, performance improvers, and flame suppressants. Examples of these additives include the various additives described in or cited in JP 2024-057060 A. When the heat transfer fluid contains additives, the total mass is 0% by mass or more, 0.1% by mass or more, or 1% by mass or more. It may also be 10% by mass or less, 5% by mass or less, or 3% by mass or less. The above upper and lower limits can be arbitrarily combined, and may be, for example, 0 to 10% by mass.

[0268] The transmission fluid may be substantially free of other compounds in addition to the compounds represented by formulas (A) to (D) and (D1) and the formula (1) described below. When the transmission fluid is substantially free of other compounds, the upper limit of the content of other compounds is preferably 10,000 ppm or less, more preferably 1,000 ppm or less, and particularly preferably 100 ppm or less. The lower limit is not particularly limited, but may be 10 ppm or more, 1 ppm or more, or 0 ppm or more. The above upper and lower limits can be combined arbitrarily, and may be, for example, 1 to 10,000 ppm.

[0269] The heat transfer fluid may be prepared by mixing the compounds represented by formulas (A) to (D) and (D1) and the formula (1) described below, and, if necessary, the additives described above. The performance of the heat transfer fluid can be evaluated by known methods.

[0270] <<Method for exchanging heat between an object and a heat transfer fluid>> One aspect of the present disclosure relates to a method for exchanging heat between an object and a heat transfer fluid, comprising using a heat transfer fluid containing a compound represented by the following formula (1) and the aforementioned formulas (A) to (D) and (D1). Below, methods for exchanging heat between an object and a heat transfer fluid, including using a compound represented by formula (1) and a heat transfer fluid containing a compound represented by formula (1), will be described in detail, representing methods using a heat transfer fluid containing a compound represented by formula (1), formulas (A) to (D), and formula (D1). Regarding some of the methods described below, methods using a compound represented by formula (1) will be described in detail, representing methods using a compound represented by formula (1), formulas (A) to (D), and formula (D1). That is, in the methods described below, the compound represented by formula (1) can be understood by replacing it with a compound represented by formula (A) to (D) or formula (D1), unless there is a contradiction in chemical structure.

[0271]

[0272] In formula (1), Y １ , Y ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent. <Heat Transfer Fluid> The heat transfer fluid is used to exchange heat between an object and the heat transfer fluid. The heat transfer fluid contains a compound represented by the above formula (1). In formula (1), Y １ , Y ２ , Y ３ , and Y ４are each preferably independently an arbitrary substituent. Examples of the arbitrary substituent include an alkyl group having 1 to 20 carbon atoms (e.g., a methyl group, an ethyl group, an isopropyl group, etc.), an alkenyl group having 2 to 20 carbon atoms (e.g., an ethenyl group, a 2-propenyl group, a 4-butenyl group, etc.), an alkynyl group having 2 to 20 carbon atoms (e.g., an ethynyl group, a 2-methyl-3-butyn-2-yl group, etc.), a cycloalkyl group having 3 to 20 carbon atoms (e.g., a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc.), a cycloalkenyl group having 3 to 20 carbon atoms, a cycloalkynyl group having 3 to 20 carbon atoms, an aryl group having 6 ... C1-C20 aryl groups (e.g., phenyl, 1-naphthyl, 2-naphthyl, 4-phenylphenyl, etc.), C3-C20 heteroaryl groups (e.g., 2-furyl, 2-thiophenyl, 2-pyridyl, 3-imidazolyl, etc.), C1-C20 alkoxy groups (e.g., methoxy, ethoxy, isopropoxy, etc.), C4-C40 cycloalkylalkyl groups (e.g., cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, etc.), C7-C40 arylalkyl groups (e.g., phenylmethyl, etc.), a heteroarylalkyl group having 4 to 40 carbon atoms, an alkoxyalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or a silyl group (e.g., trimethylsilyl group, phenyldimethylsilyl group, t-butyldimethylsilyl group, etc.) which may be substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms; an optionally substituted siloxy group (e.g., trimethylsiloxy group, phenyldimethylsiloxy group, t-butyldimethylsiloxy group, etc.); and an optionally substituted siloxysiloxy group. Examples of the alkyl group include (trimethylsiloxy)dimethylsiloxy, (phenyldimethylsiloxy)phenylmethylsiloxy, and (t-butyldimethylsiloxy)dimethylsiloxy groups), and halogen atoms. Of these, alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, and aryl groups having 6 to 20 carbon atoms, which are stable against oxygen and moisture, are preferred, linear alkyl groups having 1 to 20 carbon atoms and aryl groups having 6 to 20 carbon atoms are more preferred, and methyl and phenyl groups are even more preferred.Some of the carbon atoms may be substituted with Si, Si—O, Si—O—Si, O—Si—O, O, CO, COO, CONH, OCONH, N, NN, or the like. Here, Si and N may be substituted with a hydrogen atom or any of the above-mentioned substituents. Among these, preferred are compounds stable to oxygen and moisture in which some of the carbon atoms are substituted with Si, Si—O, Si—O—Si, or O—Si—O, and more preferred are an optionally substituted silyl group, an optionally substituted siloxy group, or an optionally substituted siloxysiloxy group. Some of the hydrogen atoms are alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, alkynyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, F, Cl, Br, I, or NH. ２ , NO ２ , S.O. ３ The hydrogen atoms may be substituted with any substituent such as H, COOH, CHO, OH, or SH. Examples of hydrogen atoms substituted include substituted alkyl groups such as a chloromethyl group and a 2,2,2-trichloroethyl group; substituted aryl groups such as a 4-methylphenyl group, a 4-methoxyphenyl group, and a 4-chlorophenyl group; and substituted arylalkyl groups such as a 4-methylphenylmethyl group and a 4-methoxyphenylethyl group. Of these, substituted aryl groups are preferred. １ , Y ２ , Y ３ , and Y ４ Preferred are alkyl groups, aryl groups, substituted alkyl groups, substituted aryl groups, and compounds in which some of the carbon atoms are substituted with Si, Si—O, Si—O—Si, or O—Si—O, more preferred are alkyl groups, aryl groups, optionally substituted siloxy groups, and optionally substituted siloxysiloxy groups, and even more preferred are methyl groups, phenyl groups, trimethylsiloxy groups, and (trimethylsiloxy)dimethylsiloxy groups. For the purposes of improving the stability of the compound and reducing hydrophilicity, the optional substituents are preferably composed of only four types of atoms: carbon atoms, hydrogen atoms, oxygen atoms, and Si atoms.

[0273] Y １ , Y ２ , Y ３ , and Y ４ may be the same or different. It is preferable that the compound contains two or more kinds of compounds because it reduces crystallinity and becomes liquid at low temperatures, more preferably three or more kinds of compounds, and even more preferably four kinds of compounds. On the other hand, from the viewpoint of inexpensive production, it is preferable that the compound contains two or less kinds of compounds, and more preferably the compound contains the same compounds. １ , Y ２ , Y ３ , and Y ４ may be bonded to each other to form a ring structure. When a ring structure is formed, a hydrogen atom in any of the above-mentioned substituents is substituted with another arbitrary substituent. Here, the ring structure may be a 6-membered ring, an 8-membered ring, or a 10-membered ring composed of a Si atom and an O atom.

[0274] The compound represented by the formula (1) has one or more Si atoms, which have lower electronegativity than C atoms, and is thought to have a tendency to have excellent heat resistance, cold resistance, light resistance, and weather resistance, making it suitable as a heat transfer fluid used to exchange heat with an object.

[0275] Specific examples of the compound represented by formula (1) include the following compound groups.

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284] The compound represented by formula (1) may contain two or more Si atoms, three or more Si atoms, or four or more Si atoms. The inclusion of a large number of Si atoms is preferable because it enhances flame retardancy. On the other hand, since too many Si atoms increases viscosity, the number of Si atoms is preferably 10 or less, more preferably 8 or less, and even more preferably 6 or less.

[0285] The compound represented by the formula (1) has a higher flame retardancy and a lower melting point as the proportion of Si atoms increases, and therefore the proportion is usually 5% by weight or more, preferably 10% by weight or more, more preferably 15% by weight or more, even more preferably 20% by weight or more, and particularly preferably 30% by weight or more.

[0286] The compound represented by formula (1) may contain one or more O atoms, may contain two or more O atoms, or may contain three or more O atoms. By containing a large number of O atoms, the ratio of carbon atoms to hydrogen atoms in the compound is relatively reduced, and flame retardancy is enhanced, which is preferable.

[0287] The compound represented by the formula (1) may contain Si—O at least as part of its structure.

[0288] The compound represented by formula (1) may contain Si—O—Si at least as part of its structure. The compound represented by formula (1) may contain O—Si—O at least as part of its structure. Si—O—Si is a structure that is relatively stable to acids and bases, and it is preferable that an O atom bonded to a Si atom is bonded to another Si atom. In other words, it is preferable that the number of Si atoms in the compound is one more than the number of O atoms.

[0289] The compound represented by formula (1) may contain an aromatic ring in at least a part of its structure. By containing one or more aromatic rings, the ratio of hydrogen atoms in the compound is relatively reduced, and flame retardancy is enhanced, which is preferable. On the other hand, since the inclusion of a large number of aromatic rings increases crystallinity and the melting point, the number of aromatic rings is preferably 8 or less, more preferably 6 or less, and even more preferably 4 or less.

[0290] The compound represented by formula (1) may contain an F atom in its structure. Carbon substituted with an F atom is preferred because it improves flame retardancy and stability. On the other hand, there are concerns that carbon substituted with an F atom may have a negative impact on the environment, so the number of F atoms contained in the structure is preferably 5 or less, more preferably 3 or less, even more preferably 1 or less, and particularly preferably no F atom.

[0291] The content of the compound represented by formula (1) is effective when contained in the heat transfer fluid, so when used as a mixture, it is sufficient that the content is 5 wt % or more, preferably greater than 20 wt %, and more preferably greater than 50 wt %, relative to the total mass. Multiple compounds represented by formula (1) may also be mixed and used. Using a mixture can lower the melting point, making it preferable for use at low temperatures. However, the flash point is strongly affected by the lower-weight component in the mixture, so a substantially single component is preferred. When used as a single component, the content is preferably greater than 90 wt %, more preferably greater than 98 wt %, even more preferably greater than 99 wt %, and particularly preferably greater than 99.8 wt %, relative to the total mass. A substantially single component may be a completely single compound or a mixture of isomers with equal molecular weights.

[0292] The molecular weight of the compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1) above) is usually 2000 or less, preferably 1500 or less, more preferably 1000 or less, and even more preferably 800 or less, because if the molecular weight is too small, the flash point will be low. On the other hand, if the molecular weight is too small, the flash point will be low, so the molecular weight is usually 100 or more, preferably 200 or more, more preferably 300 or more, and even more preferably 400 or more. The above upper and lower limits can be combined arbitrarily. For example, it may be 100 to 2000, 200 to 1500, 300 to 1000, or 400 to 800.

[0293] The compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1)) preferably has a dynamic viscosity at 25° C. of 0.1 cSt to 100 cSt, more preferably 0.1 cSt to 80 cSt, and even more preferably 0.1 cSt to 60 cSt. The dynamic viscosity can be measured, for example, according to JIS K 2283.

[0294] The compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1)) preferably has an absolute viscosity at 25°C of 0.05 mPa·s to 200 mPa·s, more preferably 0.1 mPa·s to 50 mPa·s, even more preferably 0.5 mPa·s to 20 mPa·s, and particularly preferably 1 mPa·s to 5 mPa·s. The absolute viscosity can be measured, for example, according to JIS Z 8803.

[0295] When the compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1) above) is used in low-temperature applications such as cooling systems, low-temperature testing equipment, and low-temperature machining equipment, the absolute viscosity of the compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1) above) at −20° C. is usually 0.1 mPa·s to 5000 mPa·s, preferably 0.2 mPa·s to 1000 mPa·s, more preferably 0.5 mPa·s to 200 mPa·s, even more preferably 1 mPa·s to 100 mPa·s, and particularly preferably 2 mPa·s to 10 mPa·s. The absolute viscosity can be measured, for example, according to JIS Z 8803.

[0296] When the compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1) above) is used in cryogenic applications such as cryogenic cooling systems, cryogenic test equipment, and cryogenic machining equipment, the absolute viscosity of the compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1) above) at −20° C. is typically 1 mPa·s to 5000 mPa·s, preferably 2 mPa·s to 1000 mPa·s, more preferably 5 mPa·s to 500 mPa·s, even more preferably 10 mPa·s to 200 mPa·s, and particularly preferably 20 mPa·s to 100 mPa·s. The absolute viscosity can be measured, for example, according to JIS Z 8803.

[0297] When the compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1) above) is used in cryogenic applications such as cryogenic cooling systems, cryogenic test equipment, and cryogenic machining equipment, the absolute viscosity of the compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1) above) at −70° C. is usually 1 mPa·s to 5000 mPa·s, preferably 2 mPa·s to 1000 mPa·s, more preferably 5 mPa·s to 500 mPa·s, even more preferably 10 mPa·s to 200 mPa·s, and particularly preferably 20 mPa·s to 100 mPa·s. The absolute viscosity can be measured, for example, according to JIS Z 8803.

[0298] The compound represented by the formula (1) (the same applies to the compounds represented by the formulas (A) to (D) and (D1)) usually has a density at 25°C of 0.5 g / cm ３ ~2 g / cm ３ The heat capacity per unit volume is calculated by density x specific heat, and the higher the density, the larger the heat capacity. ３ It is preferable that the density is 0.7 g / cm or more. ３ More preferably, it is 0.8 g / cm or more. ３ More preferably, it is 0.85 g / cm or more.３ On the other hand, since a substance with a high density has a low fluidity, it is particularly preferable that the density is 1.8 g / cm or more. ３ It is preferable that the density is 1.6 g / cm or less. ３ More preferably, it is 1.4 g / cm or less. ３ The upper and lower limits can be arbitrarily combined. For example, 0.6 to 1.8 g / cm ３ and 0.7 to 1.8 g / cm ３ and 0.8 to 1.6 g / cm ３ and 0.85 to 1.4 g / cm ３ The density can be measured, for example, according to JIS Z 8807.

[0299] The compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1)) preferably has a heat of vaporization of 30 J / g to 300 J / g, more preferably 40 J / g to 200 J / g, and even more preferably 50 J / g to 150 J / g. The heat of vaporization can be measured, for example, according to JIS Z 0129.

[0300] The compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1)) with a low boiling point will volatilize and be lost during use and may cause contamination, so it is desirable for the boiling point to be high within a range that satisfies other physical properties. The lower limit of the boiling point is usually 30°C or higher, preferably 60°C or higher, more preferably 80°C or higher, even more preferably 100°C or higher, and particularly preferably 120°C or higher. On the other hand, if the boiling point is too high, the viscosity tends to increase and the burden of purification by distillation increases. Therefore, the boiling point is usually 500°C or lower, preferably 400°C or lower, more preferably 300°C or lower, and even more preferably 250°C or lower. The above upper and lower limits can be combined arbitrarily. For example, the boiling point may be 30 to 500°C, 60 to 500°C, 80 to 400°C, 100 to 300°C, or 120 to 250°C. The boiling point can be measured, for example, according to JIS K 2233.

[0301] The compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1)) preferably has a pour point of −180° C. to 0° C., more preferably −150° C. to −30° C., and even more preferably −130° C. to −50° C. The melting point can be measured, for example, according to JIS K 0064.

[0302] The melting point of the heat transfer fluid containing the compound represented by formula (1) (the same applies to the compounds represented by the above formulas (A) to (D) and formula (D1)) is preferably −180° C. to 0° C., more preferably −150° C. to −30° C., and even more preferably −130° C. to −50° C. The melting point can be measured, for example, according to JIS K 0064.

[0303] The compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1)) preferably has a surface tension of 5 mN / m to 50 mN / m, more preferably 8 mN / m to 40 mN / m, and even more preferably 10 mN / m to 30 mN / m. The surface tension can be measured, for example, by the pendant drop method.

[0304] The compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1)) preferably has a vapor pressure of 0 kPa to 100 kPa, more preferably 0.0001 kPa to 90 kPa, and even more preferably 0.0005 kPa to 80 kPa. The vapor pressure can be measured, for example, according to JIS K 2258-2.

[0305] The compound represented by formula (1) (the same applies to the compounds represented by the above formulas (A) to (D) and formula (D1)) preferably has a critical temperature of 30°C to 1000°C, more preferably 40°C to 800°C, and even more preferably 50°C to 600°C.

[0306] The compound represented by formula (1) (the same applies to the compounds represented by the above formulae (A) to (D) and formula (D1)) preferably has a critical pressure of 0.5 MPa to 5 MPa, more preferably 0.8 MPa to 4 MPa, and even more preferably 1.0 MPa to 3 MPa.

[0307] The compound represented by formula (1) (the same applies to the compounds represented by the above formulas (A) to (D) and formula (D1)) preferably has an expansion coefficient of 0.01 / K or less, more preferably 0.008 / K or less, and even more preferably 0.005 / K or less.

[0308] The compound represented by formula (1) (the same applies to the compounds represented by the above formulae (A) to (D) and (D1)) preferably has a Prandtl number at 40°C of 10 to 100, more preferably 15 to 90, and even more preferably 20 to 80.

[0309] The compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1)) typically has a thermal conductivity at 25°C of 0.01 W / m K to 1 W / m K, preferably 0.03 W / m K to 0.7 W / m K, more preferably 0.05 W / m K to 0.5 W / m K, even more preferably 0.08 W / m K to 0.3 W / m K, and particularly preferably 0.10 W / m K to 0.2 W / m K. Thermal conductivity can be measured, for example, according to JIS R 1611.

[0310] The compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1)) typically has a heat capacity at 25°C of 100 J / kg·K to 10,000 J / kg·K, preferably 300 J / kg·K to 5,000 J / kg·K, more preferably 500 J / kg·K to 3,000 J / kg·K, and even more preferably 1,000 J / kg·K to 2,000 J / kg·K. The heat capacity can be measured, for example, according to JIS R 1611.

[0311] The compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1)) preferably has a relative dielectric constant of 1 to 10, more preferably 1.3 to 9, and even more preferably 1.5 to 8. The relative dielectric constant can be measured, for example, according to JIS R 2101.

[0312] The compound represented by the formula (1) (the same applies to the compounds represented by the formulas (A) to (D) and (D1)) has a volume resistivity of 1×10 ６ Ω m to 1 x 10 １８ Preferably, it is Ω·m, and 1×10 ７ Ω m to 1 x 10 １７ More preferably, it is Ω·m, and 1×10 ８ Ω m to 1 x 10 １６ In another embodiment, the volume resistivity is 1×10 ４ Ω m to 1 x 10 １８ Ω·m is preferred, and 1×10 ５ Ω m to 1 x 10 １７ Ω·m is more preferable, and 1×10 ６ Ω m to 1 x 10 １６ The volume resistivity can be measured in accordance with JIS C 2101, for example.

[0313] The compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1)) preferably has a dielectric strength of 1 kV to 100 kV, more preferably 3 kV to 80 kV, and even more preferably 5 kV to 50 kV. The dielectric strength can be measured, for example, according to JIS C 2101.

[0314] The compound represented by formula (1) (the same applies to the compounds represented by the above formulae (A) to (D) and (D1)) preferably loses less than 5%, more preferably less than 3%, and even more preferably less than 2% of purity when heated at 60°C for 24 hours.

[0315] The compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1)) is preferably highly hydrophobic and does not absorb water, in order to prevent condensation and freezing at low temperatures and to prevent corrosion of equipment. The water solubility at 25°C is preferably 10,000 ppm or less, more preferably 5,000 ppm or less, even more preferably 3,000 ppm or less, and particularly preferably 1,000 ppm or less.

[0316] In one or more examples, the higher the hydrophobicity of the heat transfer fluid, and the lower the water absorption, the better in order to prevent condensation and freezing at low temperatures and to prevent corrosion of equipment. The solubility in water at 25°C is preferably 10,000 ppm or less, more preferably 5,000 ppm or less, even more preferably 3,000 ppm or less, and particularly preferably 1,000 ppm or less.

[0317] The compound represented by formula (1) (the same applies to the compounds represented by formulas (A) to (D) and formula (D1)) preferably has a flash point of 30°C or higher, more preferably 50°C or higher, even more preferably 100°C or higher, and particularly preferably 140°C or higher. In another embodiment, it is preferable that the compound does not have a flash point. The flash point can be measured, for example, according to JIS K 2265-2.

[0318] The compound represented by formula (1) (the same applies to the compounds represented by the above formulae (A) to (D) and (D1)) preferably has a non-flammability (NFPA) of 0 to 1, more preferably 0 to 0.5, and even more preferably 0 to 0.01.

[0319] The compound represented by formula (1) (the same applies to the compounds represented by the above formulas (A) to (D) and formula (D1)) preferably has a global warming potential of 10 or less, more preferably 8 or less, and even more preferably 5 or less.

[0320] The compound represented by formula (1) (the same applies to the compounds represented by the above formulae (A) to (D) and (D1)) preferably has a thermal stability (60°C x 24 hr) of 5% (Δwt) or less, more preferably 3% (Δwt) or less, and even more preferably 1% (Δwt) or less.

[0321] The object may be at least one selected from the group consisting of electronic computing equipment, microprocessors, semiconductor wafers used to manufacture semiconductor devices, power control semiconductors, electrochemical batteries (including lithium ion batteries), power distribution switchgear, power transformers, circuit boards, multi-chip modules, packaged or unpackaged semiconductor devices, fuel cells, and lasers.

[0322] The disclosed method may include wherein the object is an electronic computing device, the electronic computing device including one or more electronic circuit boards, and the method includes directly contacting the electronic circuit boards with the heat transfer fluid.

[0323] The process of the present disclosure may be a single-phase immersion cooling process or a two-phase immersion cooling process.

[0324] The methods of the present disclosure may be used in a system for cooling a device selected from the group consisting of a system for cooling a wafer chuck in an etcher, asher, stepper or PECVD apparatus, a system for controlling the temperature in a test head for die performance testing, a temperature control system in semiconductor process equipment, a thermal shock test of an electronic device, and a constant temperature maintenance system for an electronic device.

[0325] The compound represented by the formula (1) may be a compound represented by the following formula (2):

[0326]

[0327] In formula (2), R １ , Y ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent.

[0328] In formula (2), R １ , Y ２ , Y ３ , and Y ４are each preferably independently an arbitrary substituent. Examples of the arbitrary substituent include an alkyl group having 1 to 20 carbon atoms (e.g., a methyl group, an ethyl group, an isopropyl group, etc.), an alkenyl group having 2 to 20 carbon atoms (e.g., an ethenyl group, a 2-propenyl group, a 4-butenyl group, etc.), an alkynyl group having 2 to 20 carbon atoms (e.g., an ethynyl group, a 2-methyl-3-butyn-2-yl group, etc.), a cycloalkyl group having 3 to 20 carbon atoms (e.g., a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc.), a cycloalkenyl group having 3 to 20 carbon atoms, a cycloalkynyl group having 3 to 20 carbon atoms, an aryl group having 6 ... C1-C20 aryl groups (e.g., phenyl, 1-naphthyl, 2-naphthyl, 4-phenylphenyl, etc.), C3-C20 heteroaryl groups (e.g., 2-furyl, 2-thiophenyl, 2-pyridyl, 3-imidazolyl, etc.), C1-C20 alkoxy groups (e.g., methoxy, ethoxy, isopropoxy, etc.), C4-C40 cycloalkylalkyl groups (e.g., cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, etc.), C7-C40 arylalkyl groups (e.g., phenylmethyl, etc.), a heteroarylalkyl group having 4 to 40 carbon atoms, an alkoxyalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or a silyl group (e.g., trimethylsilyl group, phenyldimethylsilyl group, t-butyldimethylsilyl group, etc.) which may be substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms; an optionally substituted siloxy group (e.g., trimethylsiloxy group, phenyldimethylsiloxy group, t-butyldimethylsiloxy group, etc.); and an optionally substituted siloxysiloxy group. Examples of the alkyl group include (trimethylsiloxy)dimethylsiloxy, (phenyldimethylsiloxy)phenylmethylsiloxy, and (t-butyldimethylsiloxy)dimethylsiloxy groups), and halogen atoms. Of these, alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, and aryl groups having 6 to 20 carbon atoms, which are stable against oxygen and moisture, are preferred, linear alkyl groups having 1 to 20 carbon atoms and aryl groups having 6 to 20 carbon atoms are more preferred, and methyl and phenyl groups are even more preferred.Some of the carbon atoms may be substituted with Si, Si—O, Si—O—Si, O—Si—O, O, CO, COO, CONH, OCONH, N, NN, or the like. Here, Si and N may be substituted with a hydrogen atom or any of the above-mentioned substituents. Among these, preferred are compounds stable to oxygen and moisture in which some of the carbon atoms are substituted with Si, Si—O, Si—O—Si, or O—Si—O, and more preferred are an optionally substituted silyl group, an optionally substituted siloxy group, or an optionally substituted siloxysiloxy group. Some of the hydrogen atoms are alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, alkynyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, F, Cl, Br, I, or NH. ２ , NO ２ , S.O. ３ The hydrogen atoms may be substituted with any substituent such as H, COOH, CHO, OH, or SH. Examples of hydrogen atoms substituted include substituted alkyl groups such as a chloromethyl group and a 2,2,2-trichloroethyl group; substituted aryl groups such as a 4-methylphenyl group, a 4-methoxyphenyl group, and a 4-chlorophenyl group; and substituted arylalkyl groups such as a 4-methylphenylmethyl group and a 4-methoxyphenylethyl group. Of these, substituted aryl groups are preferred. ２ , Y ３ , and Y ４ is preferably an alkyl group, an aryl group, a substituted alkyl group, a substituted aryl group, or a compound in which a portion of the carbon atoms is substituted with Si, Si—O, Si—O—Si, or O—Si—O, more preferably an alkyl group, an aryl group, an optionally substituted siloxy group, or an optionally substituted siloxysiloxy group, and even more preferably a methyl group, a phenyl group, a trimethylsiloxy group, or a (trimethylsiloxy)dimethylsiloxy group. １The substituents are preferably alkyl groups, substituted alkyl groups, and compounds in which some of the carbon atoms are substituted with Si, Si—O, Si—O—Si, or O—Si—O, more preferably optionally substituted silyl groups, and even more preferably trimethylsilyl groups. For the purposes of improving the stability of the compound and reducing hydrophilicity, the optional substituents are preferably composed of only four types of atoms: carbon atoms, hydrogen atoms, oxygen atoms, and Si atoms.

[0329] OR １ , Y ２ , Y ３ , and Y ４ may be the same or different. It is preferable that the compound contains two or more kinds of compounds because the crystallinity is reduced and the compound becomes liquid at a low temperature, and it is more preferable that the compound contains three or more kinds of compounds, and it is even more preferable that the compound contains four kinds of compounds. On the other hand, from the viewpoint of inexpensive production, it is preferable that the compound contains two or less kinds of compounds, and it is more preferable that the compound contains the same compounds. １ , Y ２ , Y ３ , and Y ４ may be bonded to each other to form a ring structure. When a ring structure is formed, a hydrogen atom in any of the above-mentioned substituents is substituted with another arbitrary substituent. Here, the ring structure may be a 6-membered ring, an 8-membered ring, or a 10-membered ring composed of a Si atom and an O atom.

[0330] The compound represented by formula (2) has one or more Si—O bonds, which have higher bond energy than C—C bonds, Si—Si bonds, and C—O bonds, and is thought to have a tendency to have excellent heat resistance, cold resistance, light resistance, and weather resistance, making it more suitable as a heat transfer fluid used to exchange heat with an object.

[0331] The compound represented by the formula (1) may be a compound represented by the following formula (3).

[0332]

[0333] In formula (3), R １ , R ２ , Y ３ , and Y ４ are each independently a hydrogen atom or an arbitrary substituent.

[0334] In the formula (3), R １ , R ２ , Y ３ , and Y ４are each preferably independently an arbitrary substituent. Examples of the arbitrary substituent include an alkyl group having 1 to 20 carbon atoms (e.g., a methyl group, an ethyl group, an isopropyl group, etc.), an alkenyl group having 2 to 20 carbon atoms (e.g., an ethenyl group, a 2-propenyl group, a 4-butenyl group, etc.), an alkynyl group having 2 to 20 carbon atoms (e.g., an ethynyl group, a 2-methyl-3-butyn-2-yl group, etc.), a cycloalkyl group having 3 to 20 carbon atoms (e.g., a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc.), a cycloalkenyl group having 3 to 20 carbon atoms, a cycloalkynyl group having 3 to 20 carbon atoms, an aryl group having 6 ... C1-C20 aryl groups (e.g., phenyl, 1-naphthyl, 2-naphthyl, 4-phenylphenyl, etc.), C3-C20 heteroaryl groups (e.g., 2-furyl, 2-thiophenyl, 2-pyridyl, 3-imidazolyl, etc.), C1-C20 alkoxy groups (e.g., methoxy, ethoxy, isopropoxy, etc.), C4-C40 cycloalkylalkyl groups (e.g., cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, etc.), C7-C40 arylalkyl groups (e.g., phenylmethyl, etc.), a heteroarylalkyl group having 4 to 40 carbon atoms, an alkoxyalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or a silyl group (e.g., trimethylsilyl group, phenyldimethylsilyl group, t-butyldimethylsilyl group, etc.) which may be substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms; an optionally substituted siloxy group (e.g., trimethylsiloxy group, phenyldimethylsiloxy group, t-butyldimethylsiloxy group, etc.); and an optionally substituted siloxysiloxy group. Examples of the alkyl group include (trimethylsiloxy)dimethylsiloxy, (phenyldimethylsiloxy)phenylmethylsiloxy, and (t-butyldimethylsiloxy)dimethylsiloxy groups), and halogen atoms. Of these, alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, and aryl groups having 6 to 20 carbon atoms, which are stable against oxygen and moisture, are preferred, linear alkyl groups having 1 to 20 carbon atoms and aryl groups having 6 to 20 carbon atoms are more preferred, and methyl and phenyl groups are even more preferred.Some of the carbon atoms may be substituted with Si, Si—O, Si—O—Si, O—Si—O, O, CO, COO, CONH, OCONH, N, NN, or the like. Here, Si and N may be substituted with a hydrogen atom or any of the above-mentioned substituents. Among these, preferred are compounds stable to oxygen and moisture in which some of the carbon atoms are substituted with Si, Si—O, Si—O—Si, or O—Si—O, and more preferred are an optionally substituted silyl group, an optionally substituted siloxy group, or an optionally substituted siloxysiloxy group. Some of the hydrogen atoms are alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, alkynyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, F, Cl, Br, I, or NH. ２ , NO ２ , S.O. ３ The hydrogen atoms may be substituted with any substituent such as H, COOH, CHO, OH, or SH. Examples of hydrogen atoms substituted include substituted alkyl groups such as a chloromethyl group and a 2,2,2-trichloroethyl group; substituted aryl groups such as a 4-methylphenyl group, a 4-methoxyphenyl group, and a 4-chlorophenyl group; and substituted arylalkyl groups such as a 4-methylphenylmethyl group and a 4-methoxyphenylethyl group. Of these, substituted aryl groups are preferred. ３ , and Y ４ is preferably an alkyl group, an aryl group, a substituted alkyl group, a substituted aryl group, or a compound in which a portion of the carbon atoms is substituted with Si, Si—O, Si—O—Si, or O—Si—O, more preferably an alkyl group, an aryl group, an optionally substituted siloxy group, or an optionally substituted siloxysiloxy group, and even more preferably a methyl group, a phenyl group, a trimethylsiloxy group, or a (trimethylsiloxy)dimethylsiloxy group. １ , and R ２The substituents are preferably alkyl groups, substituted alkyl groups, and compounds in which some of the carbon atoms are substituted with Si, Si—O, Si—O—Si, or O—Si—O, more preferably optionally substituted silyl groups, and even more preferably trimethylsilyl groups. For the purposes of improving the stability of the compound and reducing hydrophilicity, the optional substituents are preferably composed of only four types of atoms: carbon atoms, hydrogen atoms, oxygen atoms, and Si atoms.

[0335] OR １ , OR ２ , Y ３ , and Y ４ may be the same or different. It is preferable that the compound contains two or more kinds of compounds because the crystallinity is reduced and the compound becomes liquid at a low temperature, and it is more preferable that the compound contains three or more kinds of compounds, and it is even more preferable that the compound contains four kinds of compounds. On the other hand, from the viewpoint of inexpensive production, it is preferable that the compound contains two or less kinds of compounds, and it is more preferable that the compound contains the same compounds. １ , R ２ , Y ３ , and Y ４ may be bonded to each other to form a ring structure. When a ring structure is formed, a hydrogen atom in any of the above-mentioned substituents is substituted with another arbitrary substituent. Here, the ring structure may be a 6-membered ring, an 8-membered ring, or a 10-membered ring composed of a Si atom and an O atom.

[0336] The compound represented by formula (3) has at least two Si—O bonds, which have higher bond energy than C—C bonds, Si—Si bonds, and C—O bonds, and is thought to have a tendency to have better heat resistance, cold resistance, light resistance, and weather resistance, making it more suitable as a heat transfer fluid used to exchange heat with an object.

[0337] The compound represented by the formula (1) may be a compound represented by the following formula (4).

[0338]

[0339] In formula (4), R １ , R ２ , R ３ , and Y ３ are each independently a hydrogen atom or an arbitrary substituent.

[0340] In the formula (4), R １ , R ２ , R ３ , and Y ４are each preferably independently an arbitrary substituent. Examples of the arbitrary substituent include an alkyl group having 1 to 20 carbon atoms (e.g., a methyl group, an ethyl group, an isopropyl group, etc.), an alkenyl group having 2 to 20 carbon atoms (e.g., an ethenyl group, a 2-propenyl group, a 4-butenyl group, etc.), an alkynyl group having 2 to 20 carbon atoms (e.g., an ethynyl group, a 2-methyl-3-butyn-2-yl group, etc.), a cycloalkyl group having 3 to 20 carbon atoms (e.g., a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc.), a cycloalkenyl group having 3 to 20 carbon atoms, a cycloalkynyl group having 3 to 20 carbon atoms, an aryl group having 6 ... C1-C20 aryl groups (e.g., phenyl, 1-naphthyl, 2-naphthyl, 4-phenylphenyl, etc.), C3-C20 heteroaryl groups (e.g., 2-furyl, 2-thiophenyl, 2-pyridyl, 3-imidazolyl, etc.), C1-C20 alkoxy groups (e.g., methoxy, ethoxy, isopropoxy, etc.), C4-C40 cycloalkylalkyl groups (e.g., cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, etc.), C7-C40 arylalkyl groups (e.g., phenylmethyl, etc.), a heteroarylalkyl group having 4 to 40 carbon atoms, an alkoxyalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or a silyl group (e.g., trimethylsilyl group, phenyldimethylsilyl group, t-butyldimethylsilyl group, etc.) which may be substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms; an optionally substituted siloxy group (e.g., trimethylsiloxy group, phenyldimethylsiloxy group, t-butyldimethylsiloxy group, etc.); and an optionally substituted siloxysiloxy group. Examples of the alkyl group include (trimethylsiloxy)dimethylsiloxy, (phenyldimethylsiloxy)phenylmethylsiloxy, and (t-butyldimethylsiloxy)dimethylsiloxy groups), and halogen atoms. Of these, alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, and aryl groups having 6 to 20 carbon atoms, which are stable against oxygen and moisture, are preferred, linear alkyl groups having 1 to 20 carbon atoms and aryl groups having 6 to 20 carbon atoms are more preferred, and methyl and phenyl groups are even more preferred.Some of the carbon atoms may be substituted with Si, Si—O, Si—O—Si, O—Si—O, O, CO, COO, CONH, OCONH, N, NN, or the like. Here, Si and N may be substituted with a hydrogen atom or any of the above-mentioned substituents. Among these, preferred are compounds stable to oxygen and moisture in which some of the carbon atoms are substituted with Si, Si—O, Si—O—Si, or O—Si—O, and more preferred are an optionally substituted silyl group, an optionally substituted siloxy group, or an optionally substituted siloxysiloxy group. Some of the hydrogen atoms are alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, alkynyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, F, Cl, Br, I, or NH. ２ , NO ２ , S.O. ３ The hydrogen atoms may be substituted with any substituent such as H, COOH, CHO, OH, or SH. Examples of hydrogen atoms substituted include substituted alkyl groups such as a chloromethyl group and a 2,2,2-trichloroethyl group; substituted aryl groups such as a 4-methylphenyl group, a 4-methoxyphenyl group, and a 4-chlorophenyl group; and substituted arylalkyl groups such as a 4-methylphenylmethyl group and a 4-methoxyphenylethyl group. Of these, substituted aryl groups are preferred. ４ is preferably an alkyl group, an aryl group, a substituted alkyl group, a substituted aryl group, or a compound in which a portion of the carbon atoms is substituted with Si, Si—O, Si—O—Si, or O—Si—O, more preferably an alkyl group, an aryl group, an optionally substituted siloxy group, or an optionally substituted siloxysiloxy group, and even more preferably a methyl group, a phenyl group, a trimethylsiloxy group, or a (trimethylsiloxy)dimethylsiloxy group. １ , R ２ , and R ３The substituents are preferably alkyl groups, substituted alkyl groups, and compounds in which some of the carbon atoms are substituted with Si, Si—O, Si—O—Si, or O—Si—O, more preferably optionally substituted silyl groups, and even more preferably trimethylsilyl groups. For the purposes of improving the stability of the compound and reducing hydrophilicity, the optional substituents are preferably composed of only four types of atoms: carbon atoms, hydrogen atoms, oxygen atoms, and Si atoms.

[0341] OR １ , OR ２ , OR ３ , and Y ４ may be the same or different. It is preferable that the compound contains two or more kinds of compounds because the crystallinity is reduced and the compound becomes liquid at a low temperature, and it is more preferable that the compound contains three or more kinds of compounds, and it is even more preferable that the compound contains four kinds of compounds. On the other hand, from the viewpoint of inexpensive production, it is preferable that the compound contains two or less kinds of compounds, and it is more preferable that the compound contains the same compounds. １ , R ２ , R ３ , and Y ４ may be bonded to each other to form a ring structure. When a ring structure is formed, a hydrogen atom in any of the above-mentioned substituents is substituted with another arbitrary substituent. Here, the ring structure may be a 6-membered ring, an 8-membered ring, or a 10-membered ring composed of a Si atom and an O atom.

[0342] The compound represented by formula (4) has at least three Si—O bonds, which have higher bond energy than C—C bonds, Si—Si bonds, and C—O bonds, and is considered to have a tendency to have even better heat resistance, cold resistance, light resistance, and weather resistance, making it more suitable as a heat transfer fluid used to exchange heat with an object.

[0343] The compound represented by the formula (1) may be a compound represented by the following formula (5).

[0344]

[0345] In formula (5), R １ , R ２ , R ３ , and R ４are each independently a hydrogen atom or an arbitrary substituent. １ is a direct bond, an oxygen atom, or any linking group.

[0346] In the formula (5), R １ , R ２ , R ３ , and R ４are each preferably independently an arbitrary substituent. Examples of the arbitrary substituent include an alkyl group having 1 to 20 carbon atoms (e.g., a methyl group, an ethyl group, an isopropyl group, etc.), an alkenyl group having 2 to 20 carbon atoms (e.g., an ethenyl group, a 2-propenyl group, a 4-butenyl group, etc.), an alkynyl group having 2 to 20 carbon atoms (e.g., an ethynyl group, a 2-methyl-3-butyn-2-yl group, etc.), a cycloalkyl group having 3 to 20 carbon atoms (e.g., a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc.), a cycloalkenyl group having 3 to 20 carbon atoms, a cycloalkynyl group having 3 to 20 carbon atoms, an aryl group having 6 ... C1-C20 aryl groups (e.g., phenyl, 1-naphthyl, 2-naphthyl, 4-phenylphenyl, etc.), C3-C20 heteroaryl groups (e.g., 2-furyl, 2-thiophenyl, 2-pyridyl, 3-imidazolyl, etc.), C1-C20 alkoxy groups (e.g., methoxy, ethoxy, isopropoxy, etc.), C4-C40 cycloalkylalkyl groups (e.g., cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, etc.), C7-C40 arylalkyl groups (e.g., phenylmethyl, etc.), a heteroarylalkyl group having 4 to 40 carbon atoms, an alkoxyalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or a silyl group (e.g., trimethylsilyl group, phenyldimethylsilyl group, t-butyldimethylsilyl group, etc.) which may be substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms; an optionally substituted siloxy group (e.g., trimethylsiloxy group, phenyldimethylsiloxy group, t-butyldimethylsiloxy group, etc.); and an optionally substituted siloxysiloxy group. Examples of the alkyl group include (trimethylsiloxy)dimethylsiloxy, (phenyldimethylsiloxy)phenylmethylsiloxy, and (t-butyldimethylsiloxy)dimethylsiloxy groups), and halogen atoms. Of these, alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, and aryl groups having 6 to 20 carbon atoms, which are stable against oxygen and moisture, are preferred, linear alkyl groups having 1 to 20 carbon atoms and aryl groups having 6 to 20 carbon atoms are more preferred, and methyl and phenyl groups are even more preferred.Some of the carbon atoms may be substituted with Si, Si—O, Si—O—Si, O—Si—O, O, CO, COO, CONH, OCONH, N, NN, or the like. Here, Si and N may be substituted with a hydrogen atom or any of the above-mentioned substituents. Among these, preferred are compounds stable to oxygen and moisture in which some of the carbon atoms are substituted with Si, Si—O, Si—O—Si, or O—Si—O, and more preferred are an optionally substituted silyl group, an optionally substituted siloxy group, or an optionally substituted siloxysiloxy group. Some of the hydrogen atoms are alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, alkynyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, F, Cl, Br, I, or NH. ２ , NO ２ , S.O. ３ The hydrogen atoms may be substituted with any substituent such as H, COOH, CHO, OH, or SH. Examples of hydrogen atoms substituted include substituted alkyl groups such as a chloromethyl group and a 2,2,2-trichloroethyl group; substituted aryl groups such as a 4-methylphenyl group, a 4-methoxyphenyl group, and a 4-chlorophenyl group; and substituted arylalkyl groups such as a 4-methylphenylmethyl group and a 4-methoxyphenylethyl group. Of these, substituted aryl groups are preferred. １ , R ２ , R ３ , and R ４ The substituents are preferably alkyl groups, substituted alkyl groups, and compounds in which some of the carbon atoms are substituted with Si, Si—O, Si—O—Si, or O—Si—O, more preferably optionally substituted silyl groups, and even more preferably trimethylsilyl groups. For the purposes of improving the stability of the compound and reducing hydrophilicity, the optional substituents are preferably composed of only four types of atoms: carbon atoms, hydrogen atoms, oxygen atoms, and Si atoms.

[0347] OR １ , OR ２ , OR ３ , and OR４ may be the same or different. It is preferable that the compound contains two or more kinds of compounds because the crystallinity is reduced and the compound becomes liquid at a low temperature, and it is more preferable that the compound contains three or more kinds of compounds, and it is even more preferable that the compound contains four kinds of compounds. On the other hand, from the viewpoint of inexpensive production, it is preferable that the compound contains two or less kinds of compounds, and it is more preferable that the compound contains the same compounds. １ , R ２ , R ３ , and R ４ may be bonded to each other to form a ring structure. When a ring structure is formed, a hydrogen atom in any of the above-mentioned substituents is substituted with another arbitrary substituent. Here, the ring structure may be a 6-membered ring, an 8-membered ring, or a 10-membered ring composed of a Si atom and an O atom.

[0348] In the formula (5), the optional linking group may be an alkylene group having 1 to 20 carbon atoms (e.g., a methylene group, an ethylene group, an isopropylene group, etc.), an alkenylene group having 1 to 20 carbon atoms (e.g., an ethenylene group, a 2-propenylene group, a 4-butenylene group, etc.), an alkynylene group having 1 to 20 carbon atoms (e.g., an ethynylene group, a 2-methyl-3-butyn-2-yl group, etc.), a cycloalkylene group having 3 to 20 carbon atoms, a cycloalkenylene group having 3 to 20 carbon atoms, a cycloalkynylene group having 3 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, a heteroarylene group having 3 to 20 carbon atoms, Examples of the alkylene group include an alkoxy group having 1 to 20 carbon atoms, a cycloalkylalkylene group having 4 to 40 carbon atoms, an arylalkylene group having 7 to 40 carbon atoms, a heteroarylalkylene group having 4 to 40 carbon atoms, and an alkoxyalkylene group having 2 to 40 carbon atoms. Among these, preferred are alkylene groups having 1 to 20 carbon atoms, cycloalkylene groups having 3 to 20 carbon atoms, and arylene groups having 6 to 20 carbon atoms, which are stable against oxygen and moisture. More preferred are linear alkylene groups having 1 to 20 carbon atoms and arylene groups having 6 to 20 carbon atoms, and even more preferred are methylene and ethylene groups. Some of the carbon atoms may be substituted with Si, Si—O, Si—O—Si, O—Si—O, O, CO, COO, CONH, OCONH, NN, or the like. Some of the hydrogen atoms are selected from alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, alkynyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, F, Cl, Br, I, NH ２ , NO ２ , S.O. ３ It may be substituted with any substituent such as H, COOH, CHO, OH, or SH.

[0349] In formula (5), L １ may be a direct bond or any linking group.

[0350] The compound represented by formula (5) has at least three Si—O bonds, which have higher bond energy than C—C bonds, Si—Si bonds, and C—O bonds, and also has a linking group, and is thought to tend to have even better heat resistance, cold resistance, light resistance, and weather resistance, as well as excellent fluidity, making it particularly suitable as a heat transfer fluid used to exchange heat with an object.

[0351] The compound represented by the formula (1) may be a compound represented by the following formula (6).

[0352]

[0353] In formula (6), R １ , R ２ , R ３ , and R ４ are each independently a hydrogen atom or an arbitrary substituent.

[0354] In the formula (6), R １ , R ２ , R ３ , and R ４are each preferably independently an arbitrary substituent. Examples of the arbitrary substituent include an alkyl group having 1 to 20 carbon atoms (e.g., a methyl group, an ethyl group, an isopropyl group, etc.), an alkenyl group having 2 to 20 carbon atoms (e.g., an ethenyl group, a 2-propenyl group, a 4-butenyl group, etc.), an alkynyl group having 2 to 20 carbon atoms (e.g., an ethynyl group, a 2-methyl-3-butyn-2-yl group, etc.), a cycloalkyl group having 3 to 20 carbon atoms (e.g., a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc.), a cycloalkenyl group having 3 to 20 carbon atoms, a cycloalkynyl group having 3 to 20 carbon atoms, an aryl group having 6 ... C1-C20 aryl groups (e.g., phenyl, 1-naphthyl, 2-naphthyl, 4-phenylphenyl, etc.), C3-C20 heteroaryl groups (e.g., 2-furyl, 2-thiophenyl, 2-pyridyl, 3-imidazolyl, etc.), C1-C20 alkoxy groups (e.g., methoxy, ethoxy, isopropoxy, etc.), C4-C40 cycloalkylalkyl groups (e.g., cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, etc.), C7-C40 arylalkyl groups (e.g., phenylmethyl, etc.), a heteroarylalkyl group having 4 to 40 carbon atoms, an alkoxyalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or a silyl group (e.g., trimethylsilyl group, phenyldimethylsilyl group, t-butyldimethylsilyl group, etc.) which may be substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms; an optionally substituted siloxy group (e.g., trimethylsiloxy group, phenyldimethylsiloxy group, t-butyldimethylsiloxy group, etc.); and an optionally substituted siloxysiloxy group. Examples of the alkyl group include (trimethylsiloxy)dimethylsiloxy, (phenyldimethylsiloxy)phenylmethylsiloxy, and (t-butyldimethylsiloxy)dimethylsiloxy groups), and halogen atoms. Of these, alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, and aryl groups having 6 to 20 carbon atoms, which are stable against oxygen and moisture, are preferred, linear alkyl groups having 1 to 20 carbon atoms and aryl groups having 6 to 20 carbon atoms are more preferred, and methyl and phenyl groups are even more preferred.Some of the carbon atoms may be substituted with Si, Si—O, Si—O—Si, O—Si—O, O, CO, COO, CONH, OCONH, N, NN, or the like. Here, Si and N may be substituted with a hydrogen atom or any of the above-mentioned substituents. Among these, preferred are compounds stable to oxygen and moisture in which some of the carbon atoms are substituted with Si, Si—O, Si—O—Si, or O—Si—O, and more preferred are an optionally substituted silyl group, an optionally substituted siloxy group, or an optionally substituted siloxysiloxy group. Some of the hydrogen atoms are alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, alkynyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, F, Cl, Br, I, or NH. ２ , NO ２ , S.O. ３ The hydrogen atoms may be substituted with any substituent such as H, COOH, CHO, OH, or SH. Examples of hydrogen atoms substituted include substituted alkyl groups such as a chloromethyl group and a 2,2,2-trichloroethyl group; substituted aryl groups such as a 4-methylphenyl group, a 4-methoxyphenyl group, and a 4-chlorophenyl group; and substituted arylalkyl groups such as a 4-methylphenylmethyl group and a 4-methoxyphenylethyl group. Of these, substituted aryl groups are preferred. １ , R ２ , R ３ , and R ４ The substituents are preferably alkyl groups, substituted alkyl groups, and compounds in which some of the carbon atoms are substituted with Si, Si—O, Si—O—Si, or O—Si—O, more preferably optionally substituted silyl groups, and even more preferably trimethylsilyl groups. For the purposes of improving the stability of the compound and reducing hydrophilicity, the optional substituents are preferably composed of only four types of atoms: carbon atoms, hydrogen atoms, oxygen atoms, and Si atoms.

[0355] OR １ , OR ２ , OR ３ , and OR４ may be the same or different. It is preferable that the compound contains two or more kinds of compounds because the crystallinity is reduced and the compound becomes liquid at a low temperature, and it is more preferable that the compound contains three or more kinds of compounds, and it is even more preferable that the compound contains four kinds of compounds. On the other hand, from the viewpoint of inexpensive production, it is preferable that the compound contains two or less kinds of compounds, and it is more preferable that the compound contains the same compounds. １ , R ２ , R ３ , and R ４ may be bonded to each other to form a ring structure. When a ring structure is formed, a hydrogen atom in any of the above-mentioned substituents is substituted with another arbitrary substituent. Here, the ring structure may be a 6-membered ring, an 8-membered ring, or a 10-membered ring composed of a Si atom and an O atom.

[0356] The group of compounds represented by the formula (6) has four or more Si—O bonds, which have higher bond energy than C—C bonds, Si—Si bonds, and C—O bonds, and it is believed that such compounds tend to have particularly excellent heat resistance, cold resistance, light resistance, and weather resistance. Therefore, they are suitable as heat transfer fluids used to exchange heat with objects. They are particularly useful as heat transfer fluids used to exchange heat with objects when the operating temperature is high.

[0357] The compound represented by the formula (1) may be a compound represented by the following formula (7):

[0358]

[0359] In formula (7), R １ , R ２ , and R ３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[0360] In the formula (7), R １ , R ２ , and R ３are each preferably independently an arbitrary substituent. Examples of the arbitrary substituent include an alkyl group having 1 to 20 carbon atoms (e.g., a methyl group, an ethyl group, an isopropyl group, etc.), an alkenyl group having 2 to 20 carbon atoms (e.g., an ethenyl group, a 2-propenyl group, a 4-butenyl group, etc.), an alkynyl group having 2 to 20 carbon atoms (e.g., an ethynyl group, a 2-methyl-3-butyn-2-yl group, etc.), a cycloalkyl group having 3 to 20 carbon atoms (e.g., a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc.), a cycloalkenyl group having 3 to 20 carbon atoms, a cycloalkynyl group having 3 to 20 carbon atoms, an aryl group having 6 ... C1-C20 aryl groups (e.g., phenyl, 1-naphthyl, 2-naphthyl, 4-phenylphenyl, etc.), C3-C20 heteroaryl groups (e.g., 2-furyl, 2-thiophenyl, 2-pyridyl, 3-imidazolyl, etc.), C1-C20 alkoxy groups (e.g., methoxy, ethoxy, isopropoxy, etc.), C4-C40 cycloalkylalkyl groups (e.g., cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, etc.), C7-C40 arylalkyl groups (e.g., phenylmethyl, etc.), a heteroarylalkyl group having 4 to 40 carbon atoms, an alkoxyalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or a silyl group (e.g., trimethylsilyl group, phenyldimethylsilyl group, t-butyldimethylsilyl group, etc.) which may be substituted with one or more alkyl groups having 1 to 20 carbon atoms or aryl groups having 1 to 20 carbon atoms; an optionally substituted siloxy group (e.g., trimethylsiloxy group, phenyldimethylsiloxy group, t-butyldimethylsiloxy group, etc.); and an optionally substituted siloxysiloxy group. Examples of the alkyl group include (trimethylsiloxy)dimethylsiloxy, (phenyldimethylsiloxy)phenylmethylsiloxy, and (t-butyldimethylsiloxy)dimethylsiloxy groups), and halogen atoms. Of these, alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, and aryl groups having 6 to 20 carbon atoms, which are stable against oxygen and moisture, are preferred, linear alkyl groups having 1 to 20 carbon atoms and aryl groups having 6 to 20 carbon atoms are more preferred, and methyl and phenyl groups are even more preferred.Some of the carbon atoms may be substituted with Si, Si—O, Si—O—Si, O—Si—O, O, CO, COO, CONH, OCONH, N, NN, or the like. Here, Si and N may be substituted with a hydrogen atom or any of the above-mentioned substituents. Among these, preferred are compounds stable to oxygen and moisture in which some of the carbon atoms are substituted with Si, Si—O, Si—O—Si, or O—Si—O, and more preferred are an optionally substituted silyl group, an optionally substituted siloxy group, or an optionally substituted siloxysiloxy group. Some of the hydrogen atoms are alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, alkynyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, F, Cl, Br, I, or NH. ２ , NO ２ , S.O. ３ The hydrogen atoms may be substituted with any substituent such as H, COOH, CHO, OH, or SH. Examples of hydrogen atoms substituted include substituted alkyl groups such as a chloromethyl group and a 2,2,2-trichloroethyl group; substituted aryl groups such as a 4-methylphenyl group, a 4-methoxyphenyl group, and a 4-chlorophenyl group; and substituted arylalkyl groups such as a 4-methylphenylmethyl group and a 4-methoxyphenylethyl group. Of these, substituted aryl groups are preferred. １ , R ２ , and R ３ The substituents are preferably alkyl groups, substituted alkyl groups, and compounds in which some of the carbon atoms are substituted with Si, Si—O, Si—O—Si, or O—Si—O, more preferably optionally substituted silyl groups, and even more preferably trimethylsilyl groups. For the purposes of improving the stability of the compound and reducing hydrophilicity, the optional substituents are preferably composed of only four types of atoms: carbon atoms, hydrogen atoms, oxygen atoms, and Si atoms.

[0361] OR １ , OR ２ , and OR ３may be the same or different. It is preferable that the compound contains two or more kinds of compounds because the crystallinity is reduced and the compound becomes liquid at a low temperature, and it is more preferable that the compound contains three or more kinds of compounds, and it is even more preferable that the compound contains four kinds of compounds. On the other hand, from the viewpoint of inexpensive production, it is preferable that the compound contains two or less kinds of compounds, and it is more preferable that the compound contains the same compounds. １ , R ２ , and R ３ may be bonded to each other to form a ring structure. When a ring structure is formed, a hydrogen atom in any of the above-mentioned substituents is substituted with another arbitrary substituent. Here, the ring structure may be a 6-membered ring, an 8-membered ring, or a 10-membered ring composed of a Si atom and an O atom.

[0362] In the formula (7), the optional linking group may be an alkylene group having 1 to 20 carbon atoms (e.g., a methylene group, an ethylene group, an isopropylene group, etc.), an alkenylene group having 2 to 20 carbon atoms (e.g., an ethenylene group, a 2-propenylene group, a 4-butenylene group, etc.), an alkynylene group having 2 to 20 carbon atoms (e.g., an ethynylene group, a 2-methyl-3-butyn-2-yl group, etc.), a cycloalkylene group having 3 to 20 carbon atoms, a cycloalkenylene group having 3 to 20 carbon atoms, a cycloalkynylene group having 3 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, a heteroarylene group having 3 to 20 carbon atoms, Examples of the alkylene group include an alkoxy group having 1 to 20 carbon atoms, a cycloalkylalkylene group having 4 to 40 carbon atoms, an arylalkylene group having 7 to 40 carbon atoms, a heteroarylalkylene group having 4 to 40 carbon atoms, and an alkoxyalkylene group having 2 to 40 carbon atoms. Among these, alkylene groups having 1 to 20 carbon atoms, which are stable against oxygen and moisture, cycloalkylene groups having 3 to 20 carbon atoms, and arylene groups having 6 to 20 carbon atoms are preferred, linear alkylene groups having 1 to 20 carbon atoms, and arylene groups having 6 to 20 carbon atoms are more preferred, and methylene and ethylene groups are even more preferred. Some of the carbon atoms may be substituted with Si, Si—O, Si—O—Si, O—Si—O, O, CO, COO, CONH, OCONH, NN, or the like. Some of the hydrogen atoms are selected from alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, alkynyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, F, Cl, Br, I, NH ２ , NO ２ , S.O. ３ It may be substituted with any substituent such as H, COOH, CHO, OH, or SH.

[0363] In formula (7), L １ is preferably a direct bond or any linking group, more preferably a direct bond or an alkylene group having 1 to 20 carbon atoms, and even more preferably a direct bond or an alkylene group having 1 to 5 carbon atoms.

[0364] In formula (7), Ar １is preferably an aryl group having 6 to 20 carbon atoms which may be unsubstituted or substituted with one or more substituents, and particularly preferably a phenyl group which may be unsubstituted or substituted with one or more substituents.

[0365] The compound represented by formula (7) has at least three Si—O bonds, which have higher bond energy than C—C bonds, Si—Si bonds, and C—O bonds, has at least one aryl group with excellent heat resistance, and has a linking group. Such compounds tend to have particularly excellent heat resistance, cold resistance, light resistance, and weather resistance, and also tend to have excellent fluidity. According to the studies of the present inventors, it has been found that when an aryl group is present in the structure, as in the compound represented by formula (7), the flash point of the compound tends to be high. For this reason, the compound is particularly useful as a heat transfer fluid used to exchange heat with an object.

[0366] The compound represented by formula (1) may be a compound represented by formula (8) below.

[0367]

[0368] In formula (8), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and Ar １ is an aryl group which may be unsubstituted or substituted with one or more optional substituents. １ is a direct bond, an oxygen atom, or any linking group.

[0369] In the formula (8), examples of the optional substituent include an alkyl group having 1 to 20 carbon atoms (e.g., a methyl group, an ethyl group, an isopropyl group, etc.), an alkenyl group having 2 to 20 carbon atoms (e.g., an ethenyl group, a 2-propenyl group, a 4-butenyl group, etc.), an alkynyl group having 2 to 20 carbon atoms (e.g., an ethynyl group, a 2-methyl-3-butyn-2-yl group, etc.), a cycloalkyl group having 3 to 20 carbon atoms (e.g., a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc.), a cycloalkenyl group having 3 to 20 carbon atoms, a cycloalkynyl group having 3 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms (e.g., a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc.), a cycloalkenyl group having 3 to 20 carbon atoms, a cycloalkynyl group having 6 ..., a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a aryl groups having 20 carbon atoms (e.g., phenyl, 1-naphthyl, 2-naphthyl, 4-phenylphenyl, etc.), heteroaryl groups having 3 to 20 carbon atoms (e.g., 2-furyl, 2-thiophenyl, 2-pyridyl, 3-imidazolyl, etc.), alkoxy groups having 1 to 20 carbon atoms (e.g., methoxy, ethoxy, isopropoxy, etc.), cycloalkylalkyl groups having 4 to 40 carbon atoms (e.g., cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl), arylalkyl groups having 7 to 40 carbon atoms (e.g., phenylmethyl, a silyl group (e.g., a trimethylsilyl group, a phenyldimethylsilyl group, a t-butyldimethylsilyl group, etc.) which may be substituted with a heteroarylalkyl group having 4 to 40 carbon atoms, an alkoxyalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or one or more alkyl groups having 1 to 20 carbon atoms or an aryl group having 1 to 20 carbon atoms; a siloxy group (e.g., a trimethylsilyl group, a phenyldimethylsiloxy group, a t-butyldimethylsiloxy group, etc.) which may be substituted; Examples of the alkyl group include a siloxy group (e.g., a (trimethylsiloxy)dimethylsiloxy group, a (phenyldimethylsiloxy)phenylmethylsiloxy group, a (t-butyldimethylsiloxy)dimethylsiloxy group, etc.), and a halogen atom. Among these, preferred are alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, and aryl groups having 6 to 20 carbon atoms, which are stable against oxygen and moisture. More preferred are linear alkyl groups having 1 to 20 carbon atoms and aryl groups having 6 to 20 carbon atoms, and even more preferred are methyl and phenyl groups. Some of the carbon atoms may be substituted with Si, Si—O, Si—O—Si, O—Si—O, O, CO, COO, CONH, OCONH, N, NN, etc.Here, Si and N may be substituted with hydrogen atoms or any of the above-mentioned substituents. Among these, preferred are compounds in which a portion of the carbon atoms is substituted with Si, Si—O, Si—O—Si, or O—Si—O, which are stable to oxygen and moisture, and more preferred are optionally substituted silyl groups, optionally substituted siloxy groups, and optionally substituted siloxysiloxy groups. Some of the hydrogen atoms may be alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, alkynyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, F, Cl, Br, I, or NH. ２ , NO ２ , S.O. ３ The hydrogen atoms may be substituted with any substituent such as H, COOH, CHO, OH, or SH. Examples of hydrogen atoms substituted include substituted alkyl groups such as a chloromethyl group and a 2,2,2-trichloroethyl group; substituted aryl groups such as a 4-methylphenyl group, a 4-methoxyphenyl group, and a 4-chlorophenyl group; and substituted arylalkyl groups such as a 4-methylphenylmethyl group and a 4-methoxyphenylethyl group. Of these, substituted aryl groups are preferred. １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ is preferably an alkyl group, an aryl group, a substituted alkyl group, or a substituted aryl group, more preferably an alkyl group or an aryl group, still more preferably a methyl group or a phenyl group, and particularly preferably a methyl group. For the purpose of improving the stability of the compound and reducing hydrophilicity, the optional substituent is preferably composed of only four types of atoms: carbon atom, hydrogen atom, oxygen atom, and Si atom.

[0370] In the formula (8), the optional linking group may be an alkylene group having 1 to 20 carbon atoms (e.g., a methylene group, an ethylene group, an isopropylene group, etc.), an alkenylene group having 2 to 20 carbon atoms (e.g., an ethenylene group, a 2-propenylene group, a 4-butenylene group, etc.), an alkynylene group having 2 to 20 carbon atoms (e.g., an ethynylene group, a 2-methyl-3-butyn-2-yl group, etc.), a cycloalkylene group having 3 to 20 carbon atoms, a cycloalkenylene group having 3 to 20 carbon atoms, a cycloalkynylene group having 3 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, a heteroarylene group having 3 to 20 carbon atoms, Examples of the alkylene group include an alkoxy group having 1 to 20 carbon atoms, a cycloalkylalkylene group having 4 to 40 carbon atoms, an arylalkylene group having 7 to 40 carbon atoms, a heteroarylalkylene group having 4 to 40 carbon atoms, and an alkoxyalkylene group having 2 to 40 carbon atoms. Among these, alkylene groups having 1 to 20 carbon atoms, which are stable against oxygen and moisture, cycloalkylene groups having 3 to 20 carbon atoms, and arylene groups having 6 to 20 carbon atoms are preferred, linear alkylene groups having 1 to 20 carbon atoms, and arylene groups having 6 to 20 carbon atoms are more preferred, and methylene and ethylene groups are even more preferred. Some of the carbon atoms may be substituted with Si, Si—O, Si—O—Si, O—Si—O, O, CO, COO, CONH, OCONH, NN, or the like. Some of the hydrogen atoms are selected from alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, alkynyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, F, Cl, Br, I, NH ２ , NO ２ , S.O. ３ It may be substituted with any substituent such as H, COOH, CHO, OH, or SH.

[0371] In formula (8), L １ is preferably a direct bond or any linking group, more preferably a direct bond or an alkylene group having 1 to 20 carbon atoms, and even more preferably a direct bond or an alkylene group having 1 to 5 carbon atoms.

[0372] In formula (8), Ar １is preferably an aryl group having 6 to 20 carbon atoms which may be unsubstituted or substituted with one or more substituents, and particularly preferably a phenyl group which may be unsubstituted or substituted with one or more substituents.

[0373] The compound represented by formula (8) has at least six Si—O bonds, which have higher bond energy than C—C bonds, Si—Si bonds, and C—O bonds, has at least one aryl group with excellent heat resistance, and has a linking group. Such compounds tend to have excellent heat resistance, cold resistance, light resistance, and weather resistance, and are thought to tend to have excellent fluidity. For this reason, they are suitable as heat transfer fluids used to exchange heat with objects. According to the inventors' studies, it has been found that when an aryl group is present in the structure, as in the compound represented by formula (8), the flash point of the compound tends to be high. For this reason, they are particularly useful as heat transfer fluids used to exchange heat with objects. Furthermore, according to the inventors' studies, when a compound has a tris(siloxy)silyl structure, as in the compound represented by formula (8), the boiling point of the compound tends to be high, making them particularly suitable as heat transfer fluids used for heat exchange methods operating in high-temperature ranges. For example, a tris(trimethylsiloxy)silyl structure, a tris(triethylsiloxy)silyl structure, and the like are preferred examples.

[0374] The compound represented by the formula (1) may be a compound represented by the following formula (9).

[0375] In formula (9), R １１ ~R １３ , R ２１ ~R ２２ , and R ３１ ~R ３３ are each independently a hydrogen atom or an arbitrary substituent, and n represents an integer of 0 to 20.

[0376] In the formula (9), examples of the optional substituent include an alkyl group having 1 to 20 carbon atoms (e.g., a methyl group, an ethyl group, an isopropyl group, etc.), an alkenyl group having 2 to 20 carbon atoms (e.g., an ethenyl group, a 2-propenyl group, a 4-butenyl group, etc.), an alkynyl group having 2 to 20 carbon atoms (e.g., an ethynyl group, a 2-methyl-3-butyn-2-yl group, etc.), a cycloalkyl group having 3 to 20 carbon atoms (e.g., a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc.), a cycloalkenyl group having 3 to 20 carbon atoms, a cycloalkynyl group having 3 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms (e.g., a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc.), a cycloalkenyl group having 3 to 20 carbon atoms, a cycloalkynyl group having 6 ..., a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a aryl groups having 20 carbon atoms (e.g., phenyl, 1-naphthyl, 2-naphthyl, 4-phenylphenyl, etc.), heteroaryl groups having 3 to 20 carbon atoms (e.g., 2-furyl, 2-thiophenyl, 2-pyridyl, 3-imidazolyl, etc.), alkoxy groups having 1 to 20 carbon atoms (e.g., methoxy, ethoxy, isopropoxy, etc.), cycloalkylalkyl groups having 4 to 40 carbon atoms (e.g., cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl), arylalkyl groups having 7 to 40 carbon atoms (e.g., phenylmethyl, a silyl group (e.g., a trimethylsilyl group, a phenyldimethylsilyl group, a t-butyldimethylsilyl group, etc.) which may be substituted with a heteroarylalkyl group having 4 to 40 carbon atoms, an alkoxyalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or one or more alkyl groups having 1 to 20 carbon atoms or an aryl group having 1 to 20 carbon atoms; a siloxy group (e.g., a trimethylsilyl group, a phenyldimethylsiloxy group, a t-butyldimethylsiloxy group, etc.) which may be substituted; Examples of the alkyl group include a siloxy group (e.g., a (trimethylsiloxy)dimethylsiloxy group, a (phenyldimethylsiloxy)phenylmethylsiloxy group, a (t-butyldimethylsiloxy)dimethylsiloxy group, etc.), and a halogen atom. Among these, preferred are alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, and aryl groups having 6 to 20 carbon atoms, which are stable against oxygen and moisture. More preferred are linear alkyl groups having 1 to 20 carbon atoms and aryl groups having 6 to 20 carbon atoms, and even more preferred are methyl and phenyl groups. Some of the carbon atoms may be substituted with Si, Si—O, Si—O—Si, O—Si—O, O, CO, COO, CONH, OCONH, N, NN, etc.Here, Si and N may be substituted with hydrogen atoms or any of the above-mentioned substituents. Among these, preferred are compounds in which a portion of the carbon atoms is substituted with Si, Si—O, Si—O—Si, or O—Si—O, which are stable to oxygen and moisture, and more preferred are optionally substituted silyl groups, optionally substituted siloxy groups, and optionally substituted siloxysiloxy groups. Some of the hydrogen atoms may be alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, alkynyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, F, Cl, Br, I, or NH. ２ , NO ２ , S.O. ３ The hydrogen atoms may be substituted with any substituent such as H, COOH, CHO, OH, or SH. Examples of hydrogen atoms substituted include substituted alkyl groups such as a chloromethyl group and a 2,2,2-trichloroethyl group; substituted aryl groups such as a 4-methylphenyl group, a 4-methoxyphenyl group, and a 4-chlorophenyl group; and substituted arylalkyl groups such as a 4-methylphenylmethyl group and a 4-methoxyphenylethyl group. Of these, substituted aryl groups are preferred. １１ ~R １３ , R ２１ ~R ２２ , and R ３１ ~R ３３ is preferably an alkyl group, an aryl group, a substituted alkyl group, or a substituted aryl group, more preferably an alkyl group or an aryl group, still more preferably a methyl group or a phenyl group, and particularly preferably a methyl group. For the purpose of improving the stability of the compound and reducing hydrophilicity, the optional substituent is preferably composed of only four types of atoms: carbon atom, hydrogen atom, oxygen atom, and Si atom.

[0377] The compound represented by the formula (1) may be a compound represented by the following formula (10).

[0378]

[0379] In formula (10), R １１～ R １２ , R ２１ ~R ２２ , and R ３１～ R ３２ are each independently a hydrogen atom or an arbitrary substituent, and Ar ２ ~Ar ３ are each independently an aryl group which may be unsubstituted or substituted with one or more optional substituents, and n is an integer of 0 to 20.

[0380] In the formula (10), the optional substituents include alkyl groups having 1 to 20 carbon atoms (e.g., methyl group, ethyl group, isopropyl group, etc.), alkenyl groups having 2 to 20 carbon atoms (e.g., ethenyl group, 2-propenyl group, 4-butenyl group, etc.), alkynyl groups having 2 to 20 carbon atoms (e.g., ethynyl group, 2-methyl-3-butyn-2-yl group, etc.), cycloalkyl groups having 3 to 20 carbon atoms (e.g., cyclopropyl group, cyclopentyl group, cyclohexyl group, etc.), cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, cycloalkyl groups having 6 to 20 carbon atoms (e.g., cyclopropyl group, cyclopentyl group, cyclohexyl group, etc.), cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 6 to 20 carbon atoms, cycloalkyl groups having 6 ... aryl groups having from 1 to 20 carbon atoms (e.g., phenyl, 1-naphthyl, 2-naphthyl, 4-phenylphenyl, etc.), heteroaryl groups having from 3 to 20 carbon atoms (e.g., 2-furyl, 2-thiophenyl, 2-pyridyl, 3-imidazolyl, etc.), alkoxy groups having from 1 to 20 carbon atoms (e.g., methoxy, ethoxy, isopropoxy, etc.), cycloalkylalkyl groups having from 4 to 40 carbon atoms (e.g., cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl), arylalkyl groups having from 7 to 40 carbon atoms (e.g., phenylmethyl, a silyl group (e.g., a trimethylsilyl group, a phenyldimethylsilyl group, a t-butyldimethylsilyl group, etc.) which may be substituted with a heteroarylalkyl group having 4 to 40 carbon atoms, an alkoxyalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or one or more alkyl groups having 1 to 20 carbon atoms or an aryl group having 1 to 20 carbon atoms; a siloxy group (e.g., a trimethylsilyl group, a phenyldimethylsiloxy group, a t-butyldimethylsiloxy group, etc.) which may be substituted; Examples of the alkyl group include a siloxy group (e.g., a (trimethylsiloxy)dimethylsiloxy group, a (phenyldimethylsiloxy)phenylmethylsiloxy group, a (t-butyldimethylsiloxy)dimethylsiloxy group, etc.), and a halogen atom. Among these, preferred are alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, and aryl groups having 6 to 20 carbon atoms, which are stable against oxygen and moisture. More preferred are linear alkyl groups having 1 to 20 carbon atoms and aryl groups having 6 to 20 carbon atoms, and even more preferred are methyl and phenyl groups. Some of the carbon atoms may be substituted with Si, Si—O, Si—O—Si, O—Si—O, O, CO, COO, CONH, OCONH, N, NN, etc.Here, Si and N may be substituted with hydrogen atoms or any of the above-mentioned substituents. Among these, preferred are compounds in which a portion of the carbon atoms is substituted with Si, Si—O, Si—O—Si, or O—Si—O, which are stable to oxygen and moisture, and more preferred are optionally substituted silyl groups, optionally substituted siloxy groups, and optionally substituted siloxysiloxy groups. Some of the hydrogen atoms may be alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, alkynyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, F, Cl, Br, I, or NH. ２ , NO ２ , S.O. ３ The hydrogen atoms may be substituted with any substituent such as H, COOH, CHO, OH, or SH. Examples of hydrogen atoms substituted include substituted alkyl groups such as a chloromethyl group and a 2,2,2-trichloroethyl group; substituted aryl groups such as a 4-methylphenyl group, a 4-methoxyphenyl group, and a 4-chlorophenyl group; and substituted arylalkyl groups such as a 4-methylphenylmethyl group and a 4-methoxyphenylethyl group. Of these, substituted aryl groups are preferred. １１ ~R １２ , R ２１ ~R ２２ , and R ３１ ~R ３２ is preferably an alkyl group, an aryl group, a substituted alkyl group, or a substituted aryl group, more preferably an alkyl group or an aryl group, still more preferably a methyl group or a phenyl group, and particularly preferably a methyl group. For the purpose of improving the stability of the compound and reducing hydrophilicity, the optional substituent is preferably composed of only four types of atoms: carbon atom, hydrogen atom, oxygen atom, and Si atom.

[0381] The group of compounds represented by formula (10) has multiple Si—O bonds with higher bond energy than C—C bonds, Si—Si bonds, and C—O bonds, and at least two aryl groups with excellent heat resistance. Such compounds tend to have excellent heat resistance, cold resistance, light resistance, and weather resistance, and are thought to tend to have excellent fluidity. Therefore, they are useful as heat transfer fluids used to exchange heat with objects. Furthermore, according to the inventors' studies, it has been found that compounds with many aryl groups tend to have a higher flash point. Therefore, compounds represented by formula (10) with at least two aryl groups are particularly suitable as heat transfer fluids used for heat exchange methods operating in a high-temperature range.

[0382] The compound represented by the formula (1) may be a compound represented by the following formula (11).

[0383]

[0384] In formula (11), R １１ , R ２１ ~R ２２ , and R ３１ are each independently a hydrogen atom or an arbitrary substituent, and Ar ２１ ~Ar ２２ , and Ar ３１ ~Ar ３２ are each independently an aryl group which may be unsubstituted or substituted with one or more optional substituents, and n is an integer of 0 to 20.

[0385] In the formula (11), the optional substituents include alkyl groups having 1 to 20 carbon atoms (e.g., methyl, ethyl, isopropyl, etc.), alkenyl groups having 2 to 20 carbon atoms (e.g., ethenyl, 2-propenyl, 4-butenyl, etc.), alkynyl groups having 2 to 20 carbon atoms (e.g., ethynyl, 2-methyl-3-butyn-2-yl, etc.), cycloalkyl groups having 3 to 20 carbon atoms (e.g., cyclopropyl, cyclopentyl, cyclohexyl, etc.), cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, cycloalkyl groups having 6 to 20 carbon atoms (e.g., cyclopropyl, cyclopentyl, cyclohexyl, etc.), cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 6 to 20 carbon atoms, cycloalkyl groups having 6 ... aryl groups having from 1 to 20 carbon atoms (e.g., phenyl, 1-naphthyl, 2-naphthyl, 4-phenylphenyl, etc.), heteroaryl groups having from 3 to 20 carbon atoms (e.g., 2-furyl, 2-thiophenyl, 2-pyridyl, 3-imidazolyl, etc.), alkoxy groups having from 1 to 20 carbon atoms (e.g., methoxy, ethoxy, isopropoxy, etc.), cycloalkylalkyl groups having from 4 to 40 carbon atoms (e.g., cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl), arylalkyl groups having from 7 to 40 carbon atoms (e.g., phenylmethyl, a silyl group (e.g., a trimethylsilyl group, a phenyldimethylsilyl group, a t-butyldimethylsilyl group, etc.) which may be substituted with a heteroarylalkyl group having 4 to 40 carbon atoms, an alkoxyalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or one or more alkyl groups having 1 to 20 carbon atoms or an aryl group having 1 to 20 carbon atoms; a siloxy group (e.g., a trimethylsilyl group, a phenyldimethylsiloxy group, a t-butyldimethylsiloxy group, etc.) which may be substituted; Examples of the alkyl group include a siloxy group (e.g., a (trimethylsiloxy)dimethylsiloxy group, a (phenyldimethylsiloxy)phenylmethylsiloxy group, a (t-butyldimethylsiloxy)dimethylsiloxy group, etc.), and a halogen atom. Among these, preferred are alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, and aryl groups having 6 to 20 carbon atoms, which are stable against oxygen and moisture. More preferred are linear alkyl groups having 1 to 20 carbon atoms and aryl groups having 6 to 20 carbon atoms, and even more preferred are methyl and phenyl groups. Some of the carbon atoms may be substituted with Si, Si—O, Si—O—Si, O—Si—O, O, CO, COO, CONH, OCONH, N, NN, etc.Here, Si and N may be substituted with hydrogen atoms or any of the above-mentioned substituents. Among these, preferred are compounds in which a portion of the carbon atoms is substituted with Si, Si—O, Si—O—Si, or O—Si—O, which are stable to oxygen and moisture, and more preferred are optionally substituted silyl groups, optionally substituted siloxy groups, and optionally substituted siloxysiloxy groups. Some of the hydrogen atoms may be alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, alkynyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, F, Cl, Br, I, or NH. ２ , NO ２ , S.O. ３ The hydrogen atoms may be substituted with any substituent such as H, COOH, CHO, OH, or SH. Examples of hydrogen atoms substituted include substituted alkyl groups such as a chloromethyl group and a 2,2,2-trichloroethyl group; substituted aryl groups such as a 4-methylphenyl group, a 4-methoxyphenyl group, and a 4-chlorophenyl group; and substituted arylalkyl groups such as a 4-methylphenylmethyl group and a 4-methoxyphenylethyl group. Of these, substituted aryl groups are preferred. １１ , R ２１ ~R ２２ , and R ３１ is preferably an alkyl group, an aryl group, a substituted alkyl group, or a substituted aryl group, more preferably an alkyl group or an aryl group, still more preferably a methyl group or a phenyl group, and particularly preferably a methyl group. For the purpose of improving the stability of the compound and reducing hydrophilicity, the optional substituent is preferably composed of only four types of atoms: carbon atom, hydrogen atom, oxygen atom, and Si atom.

[0386] The compound represented by formula (11) has a plurality of Si—O bonds, which have higher bond energy than C—C bonds, Si—Si bonds, and C—O bonds, and at least four aryl groups, which have excellent heat resistance. Such compounds tend to have even more excellent heat resistance, cold resistance, light resistance, and weather resistance, and also tend to have excellent fluidity. Therefore, they are particularly useful as heat transfer fluids used to exchange heat with objects. Furthermore, according to the inventors' studies, it has been found that compounds containing many aryl groups tend to have higher flash points. Therefore, compounds represented by formula (11) having at least four aryl groups are particularly suitable as heat transfer fluids used for heat exchange methods operating in high-temperature ranges.

[0387] <Composition> The present disclosure includes a composition containing any of the compounds represented by the above formula (1), or the above formulas (A) to (D), and (D1). The composition of the present disclosure can be suitably used as a heat transfer fluid. The compounds represented by the above formula (1), or the above formulas (A) to (D), and (D1) used in the composition of the present disclosure may have the same limitations as those described for the above formula (1), or the above formulas (A) to (D), and (D1).

[0388] The composition containing any of the compounds represented by the formula (1) or the formulas (A) to (D) and (D1) preferably has a dynamic viscosity at 25° C. of 0.1 cSt to 100 cSt, more preferably 0.1 cSt to 80 cSt, and even more preferably 0.1 cSt to 60 cSt. The dynamic viscosity can be measured, for example, according to JIS K 2283.

[0389] The composition containing any of the compounds represented by the formula (1) or the formulae (A) to (D) and (D1) preferably has an absolute viscosity at 25°C of 0.05 mPa·s to 200 mPa·s, more preferably 0.1 mPa·s to 50 mPa·s, even more preferably 0.5 mPa·s to 20 mPa·s, and particularly preferably 1 mPa·s to 5 mPa·s. The absolute viscosity can be measured, for example, according to JIS Z 8803.

[0390] When a composition containing any of the compounds represented by the formula (1) or the formulas (A) to (D) and (D1) is used in low-temperature applications such as cooling systems, low-temperature testing equipment, and low-temperature machining equipment, the absolute viscosity at −20° C. of the composition containing any of the compounds represented by the formula (1) or the formulas (A) to (D) and (D1) is typically 0.1 mPa·s to 5000 mPa·s, preferably 0.2 mPa·s to 1000 mPa·s, more preferably 0.5 mPa·s to 200 mPa·s, even more preferably 1 mPa·s to 100 mPa·s, and particularly preferably 2 mPa·s to 10 mPa·s. The absolute viscosity can be measured, for example, according to JIS Z 8803.

[0391] When a composition containing any of the compounds represented by the formula (1) or the formulas (A) to (D) and (D1) is used in cryogenic applications such as cryogenic cooling systems, cryogenic test equipment, and cryogenic machining equipment, the absolute viscosity at −20° C. of the composition containing any of the compounds represented by the formula (1) or the formulas (A) to (D) and (D1) is typically 1 mPa·s to 5000 mPa·s, preferably 2 mPa·s to 1000 mPa·s, more preferably 5 mPa·s to 500 mPa·s, even more preferably 10 mPa·s to 200 mPa·s, and particularly preferably 20 mPa·s to 100 mPa·s. The absolute viscosity can be measured, for example, according to JIS Z 8803.

[0392] When a composition containing any of the compounds represented by the formula (1) or the formulas (A) to (D) and (D1) is used in cryogenic applications such as cryogenic cooling systems, cryogenic test equipment, and cryogenic machining equipment, the absolute viscosity at −70° C. of the composition containing any of the compounds represented by the formula (1) or the formulas (A) to (D) and (D1) is typically 1 mPa·s to 5000 mPa·s, preferably 2 mPa·s to 1000 mPa·s, more preferably 5 mPa·s to 500 mPa·s, even more preferably 10 mPa·s to 200 mPa·s, and particularly preferably 20 mPa·s to 100 mPa·s. The absolute viscosity can be measured, for example, according to JIS Z 8803.

[0393] The composition containing any of the compounds represented by the formula (1) and the formulas (A) to (D) and (D1) has a density at 25°C of typically 0.5 g / cm ３ ~2 g / cm ３ The heat capacity per unit volume is calculated by density x specific heat, and the higher the density, the larger the heat capacity. ３ It is preferable that the density is 0.7 g / cm or more. ３ More preferably, it is 0.8 g / cm or more. ３ More preferably, it is 0.85 g / cm or more. ３ On the other hand, since a substance with a high density has a low fluidity, it is particularly preferable that the density is 1.8 g / cm or more. ３ It is preferable that the density is 1.6 g / cm or less. ３ More preferably, it is 1.4 g / cm or less. ３ The upper and lower limits can be arbitrarily combined. For example, 0.6 to 1.8 g / cm ３ and 0.7 to 1.8 g / cm ３ and 0.8 to 1.6 g / cm ３ and 0.85 to 1.4 g / cm ３ The density can be measured, for example, according to JIS Z 8807.

[0394] The composition containing any of the compounds represented by the formula (1) or the formulas (A) to (D) and (D1) preferably has a heat of vaporization of 30 J / g to 300 J / g, more preferably 40 J / g to 200 J / g, and even more preferably 50 J / g to 150 J / g. The heat of vaporization can be measured, for example, according to JIS Z 0129.

[0395] A composition containing any of the compounds represented by the aforementioned formula (1) or the aforementioned formulas (A) to (D) and (D1) has a low boiling point, which can volatilize and be lost during use and cause contamination. Therefore, it is desirable for the boiling point to be high within a range that satisfies other physical properties. The lower limit of the boiling point is usually 30°C or higher, preferably 60°C or higher, more preferably 80°C or higher, even more preferably 100°C or higher, and particularly preferably 120°C or higher. On the other hand, if the boiling point is too high, the viscosity tends to increase and the burden of purification by distillation increases. Therefore, the boiling point is usually 500°C or lower, preferably 400°C or lower, more preferably 300°C or lower, and even more preferably 250°C or lower. The above upper and lower limits can be combined arbitrarily. For example, the boiling point may be 30 to 500°C, 60 to 500°C, 80 to 400°C, 100 to 300°C, or 120 to 250°C. The boiling point can be measured, for example, according to JIS K 2233.

[0396] The composition containing any of the compounds represented by the above formula (1) or the above formulas (A) to (D) and (D1) preferably has a pour point of −180° C. to 0° C., more preferably −150° C. to −30° C., and even more preferably −130° C. to −50° C. The melting point can be measured, for example, according to JIS K 0064.

[0397] The composition containing any of the compounds represented by the formula (1) or the formulas (A) to (D) and (D1) preferably has a surface tension of 5 mN / m to 50 mN / m, more preferably 8 mN / m to 40 mN / m, and even more preferably 10 mN / m to 30 mN / m. The surface tension can be measured, for example, by the pendant drop method.

[0398] The composition containing any of the compounds represented by the formula (1) or the formulas (A) to (D) and (D1) preferably has a vapor pressure of 0 kPa to 10 kPa, more preferably 0.0001 kPa to 1 kPa, and even more preferably 0.0005 kPa to 0.1 kPa. The vapor pressure can be measured, for example, according to JIS K 2258-2.

[0399] The composition containing any of the compounds represented by the above formula (1) or the above formulas (A) to (D) and (D1) preferably has a critical temperature of 30°C to 1000°C, more preferably 40°C to 800°C, and even more preferably 50°C to 600°C.

[0400] The composition containing any of the compounds represented by the above formula (1), or the above formulas (A) to (D), and (D1) preferably has a critical pressure of 0.5 MPa to 5 MPa, more preferably 0.8 MPa to 4 MPa, and even more preferably 1.0 MPa to 3 MPa.

[0401] The composition containing any of the compounds represented by the above formula (1) or the above formulas (A) to (D) and (D1) preferably has an expansion coefficient of 0.01 / K or less, more preferably 0.008 / K or less, and even more preferably 0.005 / K or less.

[0402] The composition containing any of the compounds represented by the above formula (1) or the above formulas (A) to (D) and (D1) preferably has a Prandtl number at 40°C of 10 to 100, more preferably 15 to 90, and even more preferably 20 to 80.

[0403] A composition containing any of the compounds represented by the above formula (1), or the above formulas (A) to (D), and (D1) typically has a thermal conductivity at 25°C of 0.01 W / m K to 1 W / m K, preferably 0.03 W / m K to 0.7 W / m K, more preferably 0.05 W / m K to 0.5 W / m K, even more preferably 0.08 W / m K to 0.3 W / m K, and particularly preferably 0.10 W / m K to 0.2 W / m K. Thermal conductivity can be measured, for example, according to JIS R 1611.

[0404] A composition containing any of the compounds represented by the above formula (1) or the above formulas (A) to (D) and (D1) typically has a heat capacity at 25°C of 100 J / kg K to 10,000 J / kg K, preferably 300 J / kg K to 5,000 J / kg K, more preferably 500 J / kg K to 3,000 J / kg K, and even more preferably 1,000 J / kg K to 2,000 J / kg K. The heat capacity can be measured, for example, according to JIS R 1611.

[0405] The composition containing any of the compounds represented by the above formula (1) or the above formulas (A) to (D) and (D1) preferably has a relative dielectric constant of 1 to 10, more preferably 1.3 to 9, and even more preferably 1.5 to 8. The relative dielectric constant can be measured, for example, according to JIS R 2101.

[0406] The composition containing any of the compounds represented by the formula (1) and the formulas (A) to (D) and (D1) has a volume resistivity of 1×10 ６ Ω m to 1 x 10 １８ Preferably, it is Ω·m, and 1×10 ７ Ω m to 1 x 10 １７ More preferably, it is Ω·m, and 1×10 ８ Ω m to 1 x 10 １６ In another embodiment, the volume resistivity is 1×10 ４ Ω m to 1 x 10 １８ Ω·m is preferred, and 1×10 ５ Ω m to 1 x 10 １７ Ω·m is more preferable, and 1×10６ Ω m to 1 x 10 １６ The volume resistivity can be measured in accordance with JIS C 2101, for example.

[0407] The composition containing any of the compounds represented by the formula (1) or the formulas (A) to (D) and (D1) preferably has a dielectric strength of 1 kV to 100 kV, more preferably 3 kV to 80 kV, and even more preferably 5 kV to 50 kV. The dielectric strength can be measured, for example, according to JIS C 2101.

[0408] A composition containing any of the compounds represented by the above formula (1) or the above formulas (A) to (D) and (D1) preferably loses less than 5%, more preferably less than 3%, and even more preferably less than 2% of purity when heated at 60°C for 24 hours.

[0409] A composition containing any of the compounds represented by the formula (1) or the formulas (A) to (D) and (D1) is preferably highly hydrophobic and does not absorb water, in order to prevent condensation and freezing at low temperatures and to prevent corrosion of equipment. The water solubility at 25°C is preferably 10,000 ppm or less, more preferably 5,000 ppm or less, even more preferably 3,000 ppm or less, and particularly preferably 1,000 ppm or less.

[0410] In one or more examples, the higher the hydrophobicity of the composition and the lower the water absorption, the better in order to prevent condensation and freezing at low temperatures and to prevent corrosion of equipment. The solubility in water at 25°C is preferably 10,000 ppm or less, more preferably 5,000 ppm or less, even more preferably 3,000 ppm or less, and particularly preferably 1,000 ppm or less.

[0411] The composition containing any of the compounds represented by the above formula (1) or the above formulas (A) to (D) and (D1) preferably has a flash point of 30°C or higher, more preferably 50°C or higher, even more preferably 100°C or higher, and particularly preferably 140°C or higher. In another embodiment, it is preferable that the composition does not have a flash point. The flash point can be measured, for example, according to JIS K 2265-2.

[0412] The composition containing any of the compounds represented by the above formula (1) or the above formulas (A) to (D) and (D1) preferably has a non-flammability (NFPA) of 0 to 1, more preferably 0 to 0.5, and even more preferably 0 to 0.01.

[0413] A composition containing any of the compounds represented by the above formula (1) or the above formulas (A) to (D) and (D1) preferably has a global warming potential of 10 or less, more preferably 8 or less, and even more preferably 5 or less.

[0414] The composition containing any of the compounds represented by the above formula (1) or the above formulas (A) to (D) and (D1) preferably has a thermal stability (60°C x 24 hr) of 5% (Δwt) or less, more preferably 3% (Δwt) or less, and even more preferably 1% (Δwt) or less.

[0415] In one or several examples, the composition of the present disclosure is preferably compatible with materials such as metals such as aluminum, magnesium, stainless steel, copper, beryllium, beryllium-copper alloy (98% beryllium), brass, iron, nickel, and bronze; elastomers such as fluororubber, silicone rubber, fluorosilicone rubber, NBR, chloroprene rubber, butyl rubber, urethane rubber, EPDM, and natural rubber; and plastics such as PTFE, PFA, nylon, polyester, polyurethane, low-density PE, polypropylene, polycarbonate, ABS copolymer, polyphenyl oxide, PET, POM, PVC, and PMMA. In other words, the composition does not corrode, swell, or deteriorate the above materials, and the composition does not react with the above materials.

[0416] One aspect of the present disclosure is a composition containing a compound represented by formula (A), wherein the total mass of the compound represented by formula (A) in the composition is 5 mass% or more, and the volume resistivity is 1×10 ４ The composition includes a composition having a viscosity of Ω·m or more and a vapor pressure at 25°C of 10 kPa or less.

[0417] One aspect of the present disclosure includes a composition containing the compound represented by formula (C), wherein the composition has a vapor pressure at 25°C of 10 kPa or less and an absolute viscosity at -20°C of 100 mPa s or less.

[0418] One aspect of the present disclosure includes a composition containing a compound represented by the following formula (D), wherein the composition has a vapor pressure at 25°C of 10 kPa or less and an absolute viscosity at -20°C of 100 mPa s or less:

[0419] <Method for Manufacturing a Semiconductor Device> The present disclosure relates to a method for manufacturing a semiconductor device, comprising using one or more semiconductor processing apparatus selected from the group consisting of an etcher, an asher, a stepper, and a plasma-enhanced chemical vapor deposition (PECVD) chamber, wherein the semiconductor processing apparatus includes at least one temperature control unit (TCU) that exchanges heat with the semiconductor device, the TCU including a heat transfer fluid, and the heat transfer fluid including one or more compounds represented by the aforementioned formula (1), or any of the aforementioned formulas (A) to (D), and (D1).

[0420] The compounds represented by the aforementioned formula (1), the aforementioned formulas (A) to (D), and (D1) used in the method of the present disclosure may have the same limitations as those described for the aforementioned formula (1), the aforementioned formulas (A) to (D), and (D1).

[0421] <<Thermal Shock Test Method for Semiconductor Devices>> The present disclosure relates to a thermal shock test method for semiconductor devices, the method comprising, in any order: i. cooling the semiconductor device using a first bath made of a heat transfer fluid to a temperature comprised between −10° C. and −100° C., preferably between −10° C. and −40° C., and ii. heating the semiconductor using a second bath made of a heat transfer fluid to a temperature comprised between 60° C. and 250° C., wherein one or preferably both of the first and second baths are made of a heat transfer fluid comprising one or more compounds represented by any of the aforementioned formulas (1), (A) to (D), and (D1).

[0422] The compounds represented by the aforementioned formula (1), the aforementioned formulas (A) to (D), and (D1) used in the method of the present disclosure may have the same limitations as those described for the aforementioned formula (1), the aforementioned formulas (A) to (D), and (D1).

[0423] <<Method for Vapor Phase Soldering of Semiconductor Devices>> The present disclosure relates to a method for vapor phase soldering of semiconductor devices, comprising: i. providing a semiconductor device containing a soldering paste; ii. providing a sealed chamber containing a heat transfer fluid at its boiling point such that heated vapor of the heat transfer fluid is generated in the sealed chamber; iii. introducing the semiconductor device into the sealed chamber in contact with the vapor of the heat transfer fluid, thereby melting the soldering paste by contact with the heated vapor; wherein the heat transfer fluid contains one or more of the compounds represented by the aforementioned formula (1), or any of the aforementioned formulas (A) to (D), and (D1).

[0424] The compounds represented by the aforementioned formula (1), the aforementioned formulas (A) to (D), and (D1) used in the method of the present disclosure may have the same limitations as those described for the aforementioned formula (1), the aforementioned formulas (A) to (D), and (D1).

[0425] <Substrate Treatment Method> The present disclosure relates to a substrate treatment method for vapor phase soldering of semiconductor devices, comprising: maintaining a substrate at a constant temperature with a heat transfer fluid; and treating the substrate with a reactive gas, wherein the heat transfer fluid contains one or more compounds represented by the aforementioned formula (1), or any of the aforementioned formulas (A) to (D), and (D1).

[0426] Here, the substrate processing includes etching, film formation, cleaning, etc. Film formation processing further includes thermal CVD, plasma CVD, and ALD. The reactive gas may be plasma gas. The temperature to be maintained is not particularly limited, but may usually be in the range of -80°C to 500°C, for example, 45°C to 55°C.

[0427] The compounds represented by the aforementioned formula (1), the aforementioned formulas (A) to (D), and (D1) used in the method of the present disclosure may have the same limitations as those described for the aforementioned formula (1), the aforementioned formulas (A) to (D), and (D1).

[0428] <Device> The present disclosure relates to a device comprising an electronic computing device and a heat transfer fluid, wherein the heat transfer fluid comprises one or more compounds represented by formula (1) above, or any of formulas (A) to (D) and (D1) above.

[0429] The compounds represented by the aforementioned formula (1), the aforementioned formulas (A) to (D), and (D1) used in the device of the present disclosure may have the same limiting conditions as those described for the aforementioned formula (1), the aforementioned formulas (A) to (D), and (D1).

[0430] Apparatus The present disclosure relates to an apparatus comprising a battery, preferably a rechargeable battery, and a thermal management system for the battery, the thermal management system comprising a heat transfer fluid that exchanges heat with the battery, wherein the heat transfer fluid comprises one or more of the compounds represented by Formula (1) above, Formulas (A)-(D) and (D1) above.

[0431] The compounds represented by the aforementioned formula (1), the aforementioned formulas (A) to (D), and (D1) used in the device of the present disclosure may have the same limiting conditions as those described for the aforementioned formula (1), the aforementioned formulas (A) to (D), and (D1).

[0432] <Heat Transfer Fluid> The present disclosure relates to a heat transfer fluid for exchanging heat between an object and the heat transfer fluid, which includes one or more compounds represented by the aforementioned formula (1), or any of the aforementioned formulas (A) to (D), and (D1).

[0433] The compounds represented by the aforementioned formula (1), the aforementioned formulas (A) to (D), and (D1) used in the heat transfer fluid of the present disclosure may have the same limitations as those described for the aforementioned formula (1), the aforementioned formulas (A) to (D), and (D1).

[0434] In some embodiments, an apparatus requiring heat transfer is provided. The apparatus includes a device and a mechanism for transferring heat to or from the device using a heat-transfer fluid. The heat-transfer fluid can be a compound represented by Formula (1) above, or Formulas (A)-(D), and (D1) above. Exemplary apparatus include air conditioning systems, refrigeration systems, test equipment, and machining equipment. Other examples include test heads used in automated test equipment for verifying the performance of semiconductor dies, wafer chucks used to hold silicon wafers in ashers, steppers, and etchers, thermostatic chambers, and thermal shock test chambers. In still other embodiments, the apparatus provided can include refrigerated transport vehicles, heat pumps, supermarket food coolers, commercial display cases, storage warehouse cooling systems, geothermal heating systems, solar heating systems, organic Rankine cycle devices, and combinations thereof.

[0435] The provided apparatus includes devices. A device is defined herein as a component, workpiece, assembly, etc., that is cooled, heated, or maintained at a selected temperature. Such devices include electrical, mechanical, and optical components. Examples of devices of the present disclosure include, but are not limited to, microprocessors, wafers used in semiconductor device fabrication, power control semiconductors, power distribution switchgear, power transformers, circuit boards, multi-chip modules, packaged and unpackaged semiconductor devices, lasers, chemical reactors, fuel cells, and electrochemical cells. In some embodiments, the device can include a cooling device, a heating device, or a combination thereof. In other embodiments, the device can include electronic components and solder that are to be soldered. Typically, the heat required for soldering can be provided by a vapor phase having a temperature above 170°C, above 200°C, above 230°C, or even higher.

[0436] In one embodiment, the device can include equipment used to test the performance of semiconductor die. Dies are individual "chips" cut from a wafer of semiconductor substrate. Dies are obtained from a semiconductor foundry and must be inspected to ensure they meet performance and processor speed requirements. Testing is used to separate "Known Good Die" (KGD) from die that do not meet performance requirements. This testing is typically performed at temperatures ranging from about -80°C to about 100°C.

[0437] In some cases, dies are tested one at a time, and each die is held in a chuck. This chuck provides cooling for the die as part of its design. In other cases, multiple dies are held in a chuck and tested either serially or in parallel. In this situation, the chuck provides cooling for the multiple dies during the test procedure. It may be advantageous to test the die at high temperatures to characterize the die's performance under high-temperature conditions. In this case, a heat transfer fluid with good cooling capabilities well above room temperature is advantageous. In some cases, the die are tested at very low temperatures. For example, complementary metal-oxide semiconductor ("CMOS") devices function particularly quickly at low temperatures. When automated test equipment (ATE) employs CMOS devices "on board" as part of its permanent logic hardware, it may be advantageous to maintain the logic hardware at low temperatures.

[0438] Therefore, to provide maximum versatility for ATE, heat transfer fluids typically perform well at both low and high temperatures (i.e., typically have good heat transfer properties over a wide temperature range), are inert (i.e., are non-flammable, have low toxicity, and are non-chemically reactive), have high dielectric strength, have low environmental impact, and have predictable heat transfer properties over the entire operating temperature range.

[0439] In another embodiment, the apparatus can include an etcher. The etcher can operate at a temperature ranging from about 70° C. to about 150° C. Typically, during etching, a reactive plasma is used to anisotropically etch structures into the semiconductor. The semiconductor can include a silicon wafer, or can include a II-VI or III-V semiconductor. In some embodiments, the semiconductor material can include, for example, a III-V semiconductor material, such as GaAs, InP, AlGaAs, GaInAsP, or GaInNAs. In other embodiments, the provided process can be useful for etching II-VI semiconductor materials (e.g., materials that can include cadmium, magnesium, zinc, selenium, tellurium, and combinations thereof). An exemplary II-VI semiconductor material can include a CdMgZnSe alloy. Other II-VI semiconductor materials, such as CdZnSe, ZnSSe, ZnMgSSe, ZnSe, ZnTe, ZnSeTe, HgCdSe, and HgCdTe, can also be etched using the provided process. The semiconductor to be processed is typically held at a constant temperature. Therefore, a heat transfer fluid that can have a single phase over the entire temperature range is typically used. In addition, the heat transfer fluid typically has predictable performance over the entire range, so that the temperature can be precisely maintained.

[0440] In another embodiment, the device can include an asher operating at a temperature ranging from about 40° C. to about 150° C. An asher is a device capable of removing photosensitive organic masks made from positive or negative photoresists. These masks are used during etching to provide a pattern on the semiconductor being etched.

[0441] In some embodiments, the device can include a stepper capable of operating at temperatures ranging from about 40°C to about 80°C. Steppers are an essential part of photolithography used in semiconductor manufacturing to produce the reticles required for production. The reticle is a tool containing the pattern image that must be stepped and repeated using the stepper to expose the entire wafer or mask. The reticle is used to create the pattern of light and shadow needed to expose a photosensitive mask. Films used in steppers are typically maintained within a temperature range of ±0.2°C to maintain good performance of the finished reticle.

[0442] In yet another embodiment, the device can include a plasma-enhanced chemical vapor deposition (PECVD) chamber capable of operating at temperatures ranging from about 50° C. to about 150° C. In the PECVD process, silicon oxide, silicon nitride, and silicon carbide films can be grown on a wafer by chemical reactions initiated in a reagent gas containing silicon and either 1) oxygen, 2) nitrogen, or 3) carbon. The chuck on which the wafer rests is maintained at a uniform, constant temperature at each selected temperature.

[0443] In yet other embodiments, the device may comprise an electronic device, such as a processor, such as a microprocessor. As these electronic devices become more powerful, the amount of heat they generate per unit time also increases. Therefore, the mechanism of heat transfer plays an important role in processor performance. Heat transfer fluids typically have good heat transfer performance, good electrical compatibility (even when used in "indirect contact" applications such as those employing cold plates), as well as low toxicity, low (or non-flammability), and low environmental impact. Good electrical compatibility requires that a candidate heat transfer fluid exhibit high dielectric strength, high volume resistivity, and poor solubility for polar materials. In addition, the heat transfer fluid must exhibit good mechanical compatibility, i.e., it must not adversely affect typical materials of construction.

[0444] The present disclosure includes a mechanism for conducting heat. The mechanism includes a heat transfer fluid provided. The heat transfer fluid includes one or more compounds represented by formula (1) above, or any of formulas (A)-(D), and (D1) above. Heat is transferred by placing the heat transfer mechanism in thermal contact with a device. When placed in thermal contact with the device, the heat transfer mechanism removes heat from the device, provides heat to the device, or maintains the device at a selected temperature. The direction of heat flow (from or to the device) is determined by the relative temperature difference between the device and the heat transfer mechanism.

[0445] Heat transfer mechanisms can include equipment for managing heat transfer fluids, including, but not limited to, pumps, valves, fluid containment systems, pressure control systems, condensers, heat exchangers, heat sources, heat sinks, cooling systems, active temperature control systems, and passive temperature control systems. Examples of suitable heat transfer mechanisms include, but are not limited to, temperature-controlled wafer chucks in plasma-enhanced chemical vapor deposition (PECVD) tools, temperature-controlled test heads for die performance testing, temperature-controlled work areas in semiconductor processing equipment, thermal shock test chambers, liquid reservoirs, and thermostatic baths. In some systems, such as etchers, ashers, PECVD chambers, and vapor-phase soldering devices, the upper desired operating temperature can be up to 170°C, up to 200°C, or even up to 230°C.

[0446] Heat can be transferred by placing a heat transfer mechanism in thermal contact with the device. When placed in thermal contact with the device, the heat transfer mechanism removes heat from the device, provides heat to the device, or maintains the device at a selected temperature. The direction of heat flow (from or to the device) is determined by the relative temperature difference between the device and the heat transfer mechanism. The provided apparatus can also include refrigeration systems, cooling systems, test equipment, and processing equipment. In some embodiments, the provided apparatus can be a constant temperature chamber or a thermal shock test chamber.

[0447] In another aspect, a heat transfer method is provided that includes providing a device and conducting heat to or from the device using a mechanism. The mechanism can include one or more heat transfer fluids of compounds represented by formula (1) above, or any of formulas (A)-(D), and (D1) above, as disclosed herein. The provided method can include vapor phase soldering, where the device is an electronic component to be soldered.

[0448] The objects and advantages of the present disclosure are further illustrated by the following examples, although the particular materials and amounts thereof recited in these examples, as well as other conditions and details, should not be construed to unduly limit the present disclosure.

[0449] The physical properties of each compound used as a heat transfer fluid are shown in Tables 1 and 2. In Table 1, values ​​marked with an * are estimated values. In the tables below, blank spaces indicate that the physical property value is unknown.

[0450]

[0451]

[0452] <Compounds> Each compound used in the examples has the following structure.

[0453]

[0454] Table 3 shows the physical properties of each compound represented by formula (A) that may be included in the heat transfer fluid of the present disclosure.

[0455]

[0456] <Compounds> Each compound shown in Table 3 has the following structure.

[0457]

[0458] Table 4 shows the physical properties of each compound represented by formula (C) that may be included in the heat transfer fluid of the present disclosure.

[0459]

[0460] <Compounds> Each compound shown in Table 4 has the following structure.

[0461]

[0462] Table 5 shows the physical properties of each compound represented by formula (D) that may be included in the heat transfer fluid of the present disclosure.

[0463]

[0464] <Compounds> Each compound shown in Table 5 has the following structure.

[0465]

[0466] Table 6 shows the physical properties of each compound represented by formula (1) that may be included in the heat transfer fluid of the present disclosure.

[0467]

[0468] <Compounds> Each compound shown in Table 6 has the following structure.

[0469]

[0470] According to the present disclosure, it is possible to provide a heat transfer fluid that is thermally stable over a wide temperature range, suitable for various uses, and has a short atmospheric lifetime that reduces the global warming potential.

Claims

A heat transfer fluid comprising a compound represented by the following formula (A): The number of Si atoms in the formula (A) is 1, A heat transfer fluid, wherein the total mass of the compounds represented by formula (A) in the heat transfer fluid is 5 mass % or more. (In formula (A), Y ５ , Y ６ , Y ７ , and Y ８ each independently represents a group containing 1 to 20 carbon atoms, a hydrogen atom, or a halogen. 　 The heat transfer fluid according to claim 1, wherein the compound represented by formula (A) comprises any one of compounds represented by the following formulas (Aa) to (Ae): (In formulas (Aa) to (Ae), R Ａ１ ~R Ａ２０ each independently represents a group containing 1 to 10 carbon atoms. R Ａ１ ~R Ａ２０ 3. The heat transfer fluid according to claim 2, wherein each of the groups independently is any one selected from the group consisting of a methyl group, an ethyl group, a propyl group, a vinyl group, a propynyl group, a butyl group, and a phenyl group. R Ａ１ ~R Ａ２０ The heat transfer fluid of claim 2 , wherein is an ethyl group. 　 A heat transfer fluid comprising a compound represented by the following formula (C): A heat transfer fluid in which the number of Si atoms in the formula (C) is 4. (In formula (C), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ each independently represents a group containing 1 to 20 carbon atoms, R ４１ represents a group containing 2 to 20 carbon atoms. In formula (C), R ４１ The heat transfer fluid of claim 5 , wherein the aryl group has at least one aromatic ring. In formula (C), R ４１ is any one selected from the group consisting of an aryl group having 6 to 10 carbon atoms, a substituted aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 10 carbon atoms, and a substituted arylalkyl group having 7 to 10 carbon atoms. In formula (C), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ The heat transfer fluid of claim 5 , wherein is a methyl group. 　 The heat transfer fluid according to claim 5 , comprising, as the compound represented by formula (C), any one of compounds represented by the following formula: The heat transfer fluid according to claim 5 , wherein the total mass of the compounds represented by formula (C) in the heat transfer fluid is 51 mass % or more. 　 A heat transfer fluid comprising a compound represented by the following formula (D): (In formula (D), n represents an integer of 2 to 5. Each R independently represents a group containing 1 to 20 carbon atoms, provided that at least one R represents a group containing 2 to 20 carbon atoms.) 　 The heat transfer fluid according to claim 11 , wherein the compound represented by formula (D) comprises a compound represented by the following formula (D1): (In formula (D1), n ​​represents an integer of 2 to 5. R Ｄ１ each independently represents a group containing 1 to 20 carbon atoms; R Ｄ２ each independently represents a group containing 2 to 20 carbon atoms. In formula (D1), R Ｄ１ is an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R Ｄ２ The heat transfer fluid according to claim 12, wherein is an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms. In formula (D1), R Ｄ１ is a methyl group, and R Ｄ２ The heat transfer fluid of claim 12 , wherein is an alkyl group having 2 or 3 carbon atoms or an alkenyl group having 2 or 3 carbon atoms. 　 A method for exchanging heat between a body and a heat transfer fluid, comprising using a heat transfer fluid according to any one of claims 1 to 14.

16. The method of claim 15, wherein the object is at least one selected from the group consisting of electronic computing equipment, microprocessors, semiconductor wafers used to manufacture semiconductor devices, power control semiconductors, electrochemical batteries (including lithium ion batteries), power distribution switchgear, power transformers, circuit boards, multi-chip modules, packaged or unpackaged semiconductor devices, fuel cells, and lasers.

16. The method of claim 15, used in a system for cooling a device selected from the group consisting of a system for cooling a wafer chuck in an etcher, asher, stepper or PECVD apparatus, a system for controlling the temperature in a test head for die performance testing, a temperature control system in a semiconductor process facility, a thermal shock test of an electronic device, and a constant temperature maintenance system for an electronic device.

16. The method of claim 15, wherein the object is an electronic computing device, the electronic computing device including one or more electronic circuit boards, and the method comprises directly contacting the electronic circuit boards with the heat transfer fluid.

1. A method for manufacturing a semiconductor device, comprising using one or more semiconductor processing equipment selected from the group consisting of an etcher, an asher, a stepper, and a plasma-enhanced chemical vapor deposition (PECVD) chamber, the semiconductor processing equipment includes at least one temperature control unit (TCU) in heat exchange with the semiconductor device; The method of claim 15 , wherein the TCU comprises a heat transfer fluid. 　 An apparatus comprising an electronic computing device and a heat transfer fluid, said heat transfer fluid comprising the heat transfer fluid of any one of claims 1 to 14. 　 Use of a composition containing a compound represented by the following formula (A) as a heat transfer fluid, The number of Si atoms in the formula (A) is 1, The composition according to claim 1, wherein the total mass of the compound represented by formula (A) in the composition is 5 mass % or more. (In formula (A), Y ５ , Y ６ , Y ７ , and Y ８ each independently represents a substituent containing 1 to 20 carbon atoms. 　 Use of a composition containing a compound represented by the following formula (C) as a heat transfer fluid, Use as a heat transfer fluid, wherein the number of Si atoms in the formula (C) is 4. (In formula (C), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ each independently represents a group containing 1 to 20 carbon atoms, R ４１ represents a group containing 2 to 20 carbon atoms. 　 Use of a composition containing a compound represented by the following formula (D) as a heat transfer fluid: (In formula (D), n represents an integer of 2 to 5. Each R independently represents a group containing 1 to 20 carbon atoms, provided that at least one R represents a group containing 2 to 20 carbon atoms.) 　 A composition comprising a compound represented by the following formula (A): The number of Si atoms in the formula (A) is 1, the total mass of the compound represented by formula (A) in the composition is 5 mass% or more, Volume resistance is 1 x 10 ４ Ω m or more, A composition having a vapor pressure of 10 kPa or less at 25°C. (In formula (A), Y ５ , Y ６ , Y ７ , and Y ８ each independently represents a substituent containing 1 to 20 carbon atoms. 　 A composition comprising a compound represented by the following formula (C): the number of Si atoms in the formula (C) is 4, The vapor pressure at 25°C is 10 kPa or less, A composition having an absolute viscosity at -20°C of 100 mPa·s or less. (In formula (C), R １１ ~R １３ , R ２１ ~R ２３ , and R ３１ ~R ３３ each independently represents a group containing 1 to 20 carbon atoms, R ４１ represents a group containing 2 to 20 carbon atoms. 　 A composition comprising a compound represented by the following formula (D): The vapor pressure at 25°C is 10 kPa or less, A composition having an absolute viscosity at -20°C of 100 mPa·s or less. (In formula (D), n represents an integer of 2 to 5. Each R independently represents a group containing 1 to 20 carbon atoms, provided that at least one R represents a group containing 2 to 20 carbon atoms.)

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