Low-toxicity organic tertiary and quaternary amines and their uses

Abstract

To provide compositions that include one or more of compounds that may be useful for electronics processing (e.g., semiconductor processing composition), cleaning, stripping, degreasing, or a combination of two or more thereof.SOLUTION: Provided is a composition comprising a tertiary amine and / or quaternary ammonium compound of Formula I and / or Formula II, or a combination thereof. The compounds of Formula I and / or Formula II may be useful as low-toxicity substitutes for tetramethylammonium hydroxide.SELECTED DRAWING: None

Description

SUMMARY OF THE INVENTION

[0001] In one aspect, the present technology provides a compound of formula I and / or a compound of formula II, TIFF0007866029000001.tif50128 wherein R 1 and R 5 are each, independently, H, hydroxyl, or CH3, R 2 and R 6 are each, independently, H, hydroxyl, CH 3、 N(CH3)2, or + N(CH3)3, Y is OR 3 or N(R 8 ) i where Z is OR 7 or N(R 10 ) j where R 3 and R 7 are each, independently, H or C1-C6 alkyl, each occurrence of R 8 is, independently, C1-C6 alkyl optionally substituted with one or more hydroxyl groups, each occurrence of R 10 is, independently, H, or C1-C6 alkyl optionally substituted with one or more hydroxyl groups, R 4 is H, or a C1-C6 alkyl group optionally substituted with one or more hydroxyl, amine, or ammonium groups, a, b, d, e, f, and h are each, independently, 0 or 1, c and g are each, independently, 0, 1, or 2, i and j are each, independently, 2 or 3, X - is an anion and is present in an amount equal to the cation present in formula I or formula II.

[0002] In any embodiment, the compound of formula I can be a compound of formula IA and / or the compound of formula II can be a compound of formula IIA, TIFF0007866029000002.tif50128 wherein R 1 , R 2 , R 5 , and R 6These are H, hydroxyl, or CH3, respectively, and R 3 and R 7 Each is individually H or C1-C6 alkyl, and R 4 is a C1-C6 alkyl group which may be substituted with H or one or more hydroxyl groups, a, b, d, e, f, and h are individually 0 or 1, and c and g are individually 0, 1, or 2, X - It is an anion.

[0003] In any embodiment, the compound of formula I may be the compound of formula IB, and / or the compound of formula II may be the compound of formula IIB. TIFF0007866029000003.tif50128In formula, R 1 and R 5 These are H, hydroxyl, or CH3, respectively, and R 2 and R 6 These are H and CH individually. 3、 N(CH3)2, or + N(CH3)3, and R in each occurrence 8 Each is a C1-C6 alkyl which may be substituted with one or more hydroxyl groups, and R in each appearance 10 Each of these is a C1-C6 alkyl which may be substituted with H or one or more hydroxyl groups, and R 4 is H, or one or more hydroxyl groups, N(CH3)2, or + A C1-C6 alkyl group which may be substituted with three N(CH3) groups, where a, b, d, e, f, and h are individually 0 or 1, and c and g are individually 0, 1, or 2, X - It is an anion.

[0004] This technology also provides compositions comprising compounds of formula I (or species IA and / or IB), compounds of formula II (or species IIA and / or IIB), or combinations thereof. In any embodiment, the compositions may be useful for electronic equipment processing (e.g., semiconductor processing compositions), cleaning, stripping, degreasing, or two or more combinations thereof. Compounds of formula I (or species IA and / or IB) and / or formula II (or species IIA and / or IIB) may also be useful as catalysts, phase transfer agents, or combinations thereof.

[0005] Compounds of formula I (or species formula IA and / or IB) or formula II (or species formula IIA and / or IIB) may also be useful as substitutes for tetramethylammonium hydroxide ("TMAH"), which is a highly toxic compound. In any embodiment, compounds of formula II (or species formula IIA and / or IIB) may be useful as substitutes for tetramethylammonium hydroxide ("TMAH"), which is a highly toxic compound.

[0006] In any embodiment, the Art provides a composition comprising a compound of formula I (or species IA and / or IB) or formula II (or species IIA and / or IIB) instead of TMAH. In any embodiment, the Art provides a composition comprising a compound of formula II (or species IIA and / or IIB) instead of TMAH. [Invention 1001] A composition comprising a compound of formula I, a compound of formula II, or a combination thereof, TIFF0007866029000004.tif50128In formula, R 1 and R 5 However, individually, they are H, hydroxyl, or CH3. R 2 and R 6 However, individually, H, hydroxyl, CH3, N(CH3)2, or + It is N(CH3)3, Y is OR 3 or N(R8 ) i And Z is OR 7 or N(R 10 ) j And, R 3 and R 7 However, individually, they are H or C1-C6 alkyl, R in each appearance 8 However, each C1-C6 alkyl group may be individually substituted with one or more hydroxyl groups. R in each appearance 10 However, each of these is a C1-C6 alkyl group which may be substituted with H or one or more hydroxyl groups. R 4 However, it is a C1-C6 alkyl group which may be substituted with H, or one or more hydroxyl, amine, or ammonium groups. a, b, d, e, f, and h are individually either 0 or 1. c and g are 0, 1, or 2, respectively. i and j are 2 or 3 individually. X - However, it is an anion and exists in an amount equal to that of the cation present in formula I or formula II. composition. [Invention 1002] The compound of formula I is the compound of formula IA, and / or the compound of formula II is the compound of formula IIA. TIFF0007866029000005.tif50128In formula, R 1 , R 2 , R 5 , and R 6 However, individually, they are H, hydroxyl, or CH3. R 3 and R 7 However, individually, they are H or C1-C6 alkyl, R 4 However, it is a C1-C6 alkyl group which may be substituted with H or one or more hydroxyl groups. a, b, d, e, f, and h are individually either 0 or 1. c and g are 0, 1, or 2, respectively. X - However, the aforementioned anion, The composition of the present invention 1001. [Invention 1003] The compound of formula I is the compound of formula IB, and / or the compound of formula II is the compound of formula IIB. TIFF0007866029000006.tif50128In formula, R 1 and R 5 However, individually, they are H, hydroxyl, or CH3. R 2 and R 6 However, individually, H, CH3, N(CH3)2, or + It is N(CH3)3, R in each appearance 8 However, each C1-C6 alkyl group may be individually substituted with one or more hydroxyl groups. R in each appearance 10 However, each of these is a C1-C6 alkyl group which may be substituted with H or one or more hydroxyl groups. R 4 However, one or more hydroxyl groups, N(CH3)2, or + It is a C1-C6 alkyl group which may be substituted with an N(CH3)3 group. a, b, d, e, f, and h are individually either 0 or 1. c and g are 0, 1, or 2, respectively. X - However, the aforementioned anion, The composition of the present invention 1001. [Invention 1004] A composition of any of the present inventions 1001 to 1003, wherein a+b+c+d≧1 and e+f+g+h≧1. [Invention 1005] A composition of any of the present inventions 1001 to 1004, wherein a+b+c+d≧2 and e+f+g+h≧2. [Invention 1006] R 1and R 5 However, each of the compositions according to invention 1001 to 1005 is individually hydroxyl or CH3. [Invention 1007] R 1 and R 5 A composition according to any of invention 1001 to 1005, wherein the composition is H or CH3. [Invention 1008] R 3 and R 7 A composition of any of the present invention 1001 to 1007, wherein H is present. [Invention 1009] R 3 and R 7 However, each of the compositions 1001 to 1007 of the present invention is individually a C1-C6 alkyl group. [Invention 1010] R 3 and R 7 However, the composition of the present invention 1009 is CH3. [Invention 1011] R 4 A composition according to any one of the present invention 1001 to 1010, wherein the C1-C4 alkyl group may be substituted with one or more hydroxyl groups. [Invention 1012] R 4 The composition of the present invention 1011, wherein the methyl group may be substituted with one or more hydroxyl groups. [Invention 1013] R 4 The composition of the present invention 1011 or 1012, wherein the terminal substituted with one or more hydroxyl groups. [Invention 1014] R 4 However, any composition according to invention 1001 to 1013, wherein the hydroxyl group is substituted with two or more hydroxyl groups. [Invention 1015] R 4 However, the composition is one of the present inventions 1001 to 1013, wherein the composition is CH2CH(CH3)OH. [Invention 1016] R 4The composition according to any one of 1001 to 1010 of the present invention, wherein it is C1-C4 alkyl optionally substituted with one or more amine or ammonium groups. [The present invention 1017] R 4 The composition of the present invention 1016, wherein R is a methyl group optionally substituted with one or more amine or ammonium groups. [The present invention 1018] R 4 where R is + The composition of the present invention 1016 or the present invention 1017, which is terminally substituted with N(CH3)3 groups. [The present invention 1019] R 4 where R is CH2C(CH3)2-N(CH3)3 + The composition according to any one of 1001 to 1010 or 1016 of the present invention. [The present invention 1020] R 2 and R 6 The composition according to any one of 1001 to 1019 of the present invention, wherein both are H. [The present invention 1021] R 2 and R 6 The composition according to any one of 1001 to 1019 of the present invention, wherein both are hydroxyl. [The present invention 1022] R 2 and R 6 The composition according to any one of 1001 to 1019 of the present invention, wherein both are CH3. [The present invention 1023] R 2 and R 6 where both are N(CH3)2 or + N(CH3)3, and the composition according to any one of 1001 to 1019 of the present invention. [The present invention 1024] R in each occurrence 8 and R 10 The composition according to any one of 1001 to 1023 of the present invention, wherein each is independently C1-C6 alkyl optionally substituted with one or more hydroxyl groups. [The present invention 1025] R in each occurrence 8and R 10 However, the composition is CH3, which is one of the compositions 1001 to 1024 of the present invention. [Invention 1026] R 8 and R 10 However, the composition is one of the present invention 1001 to 1024, selected from the group consisting of CH3 and C(CH3)2CH2OH. [Invention 1027] X - The composition is one of the present invention 1001 to 1026, wherein the ion is a halide, sulfate ion, metosulfate, carbonate ion, carboxylate ion, phosphate ion, or hydroxide ion. [Invention 1028] X - However, the composition is one of the invention 1001 to 1027, which is a hydroxide ion. [Invention 1029] The compound of formula I is A composition according to any of the present invention 1001 to 1028, which is a compound of formula IA selected from the group consisting of TIFF0007866029000007.tif199162TIFF0007866029000008.tif177135 and two or more combinations thereof. [Invention 1030] The composition of the present invention 1029, wherein the compound of formula I is a compound of formula IA selected from the group consisting of DMAMPD, iso-DMAMPD, and combinations thereof. [Invention 1031] The compound of formula II is A composition according to any one of the present invention 1001 to 1030, which is a compound of formula IIA selected from the group consisting of TIFF0007866029000009.tif178132TIFF0007866029000010.tif53137 and two or more combinations thereof. [Invention 1032] The composition of the present invention 1031, wherein the compound of formula II is the compound of formula IIA, which is DMAMPD-AH. [Invention 1033] The compound of formula I is A composition according to any of the present invention 1001 to 1032, which is a compound of formula I selected from the group consisting of TIFF0007866029000011.tif154153 and two or more combinations thereof. [Invention 1034] The compound of formula II is A composition according to any of the present invention 1001 to 1033, which is a compound of formula IIB selected from the group consisting of TIFF0007866029000012.tif178128 and two or more combinations thereof. [Invention 1035] A composition according to any one of the present invention 1001 to 1034, having, based on the whole composition, about 0.1% to about 80% by weight of the compound of formula I, the compound of formula II, or a combination thereof. [Invention 1036] A composition according to any one of the present invention 1001 to 1035, having, based on the whole composition, about 1% to about 50% by weight of the compound of formula I, the compound of formula II, or a combination thereof. [Invention 1037] A composition according to any one of the present invention 1001 to 1036, which is an electronic device processing composition (e.g., a semiconductor processing composition), a cleaning composition, a stripping composition, a degreasing composition, a catalyst, a phase transfer agent, or a combination of two or more thereof. [Invention 1038] The composition of the present invention 1037, wherein the electronic equipment processing composition is a wafer cleaning composition, an anisotropic etching composition, a photolithography composition, a photoresist developing composition, a post-chemical planarization cleaning composition, a printed circuit board cleaning composition, or a combination of two or more thereof. [Invention 1039] A composition according to any one of the present invention 1001 to 1038, further comprising a stabilizer (for example, an antioxidant, oxygen scavenger, or reducing agent, such as dithionite salts, amines, hydroxylamines, sulfites, hydroquinones, hydrides, carboxylic acids, piperazines, formaldehyde, thiourea, borates, butylated hydroxytoluene, butylated hydroxyanisole, ascorbic acid, and combinations of two or more thereof). [Invention 1040] A composition according to any one of the present invention 1001 to 1039, further comprising a rust inhibitor. [Invention 1041] A composition according to any one of the present invention 1001 to 1040, further comprising an alcohol, pyrocatechol, glycerin, and / or a glycerin derivative. [Invention 1042] A composition according to any one of the present invention 1001 to 1041, wherein the compound of formula I and / or the compound of formula II is an etching agent. [Invention 1043] A composition according to any one of the present invention 1001 to 1042, further comprising a hydroxylamine (for example, hydroxylamine, hydroxylamine sulfate, hydroxylamine chloride, hydroxylamine oxalate, N,N-diethylhydroxylamine, isopropylhydroxylamine, dimethylhydroxylamine hydrochloride, and / or hydroxylamine phosphate). [Invention 1044] A composition according to any one of the present invention 1001 to 1043, further comprising an inorganic alkali compound. [Invention 1045] A composition of any of the present invention 1001 to 1044, further comprising water. [Invention 1046] A composition according to any one of the present invention 1001 to 1045, further comprising a hydrotropic component. [Invention 1047] A composition according to any one of the present invention 1001 to 1046, further comprising a pH adjuster, a buffer, or a combination thereof. [Invention 1048] A composition according to any one of the present invention 1001 to 1047, further comprising at least one organic solvent or surfactant (e.g., DMSO, alcohol, ethoxylated alcohol, betaine, alkyl sulfonic acid, aryl sulfonic acid, or a combination of two or more thereof). [Invention 1049] A composition according to any one of the present invention 1001 to 1048, further comprising a rheology modifier (for example, a polymer rheology modifier such as polyacrylic acid). [Invention 1050] A composition according to any one of the present invention 1001 to 1049, further comprising a chelating agent (for example, ethylenediaminetetraacetic acid ("EDTA")). [Invention 1051] A composition according to any one of the present invention 1001 to 1050, comprising a metal selected from the group consisting of Na, Mg, Al, K, Ca, Mn, Fe, Ni, Cu, Zn, Ag, Pd, and Cr, in a maximum of approximately 1000 ppb. [Invention 1052] A composition according to any one of the invention 1001 to 1051, having reduced toxicity compared to a composition containing the same weight percent of tetramethylammonium hydroxide (TMAH), based on rat skin toxicity. [Invention 1053] A composition according to any of invention 1001 to 1052 that is essentially TMAH-free. [Invention 1054] A compound of formula I or a compound of formula II according to any of the inventions 1001 to 1034. [Invention 1055] A process for producing the compound of formula II according to the present invention 1054, To provide a solution containing any compound of formula I from invention 1001 to 1034 and an organic solvent, The solution may be optionally heated to approximately 25°C to approximately 45°C, The process involves adding a methylating agent to the solution to produce a mixture, wherein the methylating agent is added over a period of approximately one hour. Mixing the aforementioned mixture, The mixture may be optionally cooled to below approximately 20°C, The mixture may be optionally filtered. A process that includes this. [Modes for carrying out the invention]

[0007] Detailed explanation Various embodiments are described below. It should be noted that the specific embodiments are not intended as a comprehensive description or as a limitation to a broader set of embodiments considered herein. One embodiment described in relation to a particular embodiment is not necessarily limited to that embodiment and can be implemented in any other embodiment.

[0008] As used herein, "about" is to be understood by those skilled in the art and varies to some extent depending on the context in which it is used. Where there is a use of a term that is not obvious to those skilled in the art, "about" means plus or minus 10% of that particular term, considering the context in which it is used.

[0009] In the context of describing elements, (particularly in the context of the subsequent claims) the terms “a,” “an,” and “the,” as well as similar references, are to be interpreted as encompassing both singular and plural forms unless otherwise indicated herein or unless the context clearly contradicts this. The enumeration of value ranges herein is intended solely as a simplified notation for referring individually to each distinct value that falls within that range, unless otherwise indicated herein, and each distinct value is incorporated herein as if it were individually enumerated herein. All methods described herein may be performed in any preferred order unless otherwise indicated herein or unless the context clearly contradicts this. The use of any and all examples or exemplary linguistic expressions (e.g., “etc.”) provided herein is merely intended to better illustrate embodiments and, unless otherwise stated, does not limit the claims. No language herein should be interpreted as indicating any element not claimed as essential.

[0010] Unless otherwise specified, a numerical range includes the numbers that define the range (e.g., 2 and 10), such as "2 to 10".

[0011] Unless otherwise specified, ratios, percentages, and parts are expressed by weight.

[0012] As used herein, “substituted” generally refers to alkyl, alkenyl, alkynyl, annealed, or ether groups (e.g., alkyl groups) as defined below, in which one or more bonds to hydrogen atoms contained therein are replaced by bonds to non-hydrogen or non-carbon atoms. A substituted group also includes a group in which one or more bonds to carbon or hydrogen atoms are replaced by one or more bonds, including double or triple bonds, to heteroatoms. Thus, unless otherwise specified, substituents are substituted with one or more substituents. In some embodiments, substituents are substituted with one, two, three, four, five, or six substituents. Examples of substituents include halogens (i.e., F, Cl, Br, and I), hydroxyl, alkoxy, alkenoxy, alkynoxy, aryloxy, aralkyloxy, heterocyclyloxy, and heterocyclylalkoxy groups, carbonyl (oxo), carboxyl, ester, urethane, oxime, hydroxylamine, alkoxyamine, aralkoxyamine, thiol, sulfide, sulfoxide, sulfone, sulfonyl, sulfonamide, amine, N-oxide, hydrazine, hydrazide, hydrazone, azide, amide, urea, amidine, guanidine, enamine, imide, isocyanate, isothiocyanate, cyanate, thiocyanate, imine, nitro group, and nitrile (i.e., CN).

[0013] As used herein, the “alkyl” group includes linear and branched alkyl groups having 1 to about 20 carbon atoms, typically 1 to 12 carbon atoms, or in some embodiments, 1 to 8, 1 to 6, or 1 to 4 carbon atoms. As used herein, “alkyl group” includes cycloalkyl groups as defined below. Alkyl groups may be substituted or unsubstituted. Examples of linear alkyl groups include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl groups. Examples of branched alkyl groups, but not limited to, include isopropyl, sec-butyl, t-butyl, neopentyl, and isopentyl groups. Typical substituted alkyl groups may be substituted one or more times with halo groups such as amino, thio, hydroxy, cyano, alkoxy, and / or F, Cl, Br, and I groups. As used herein, the term haloalkyl group is an alkyl group having one or more halo groups. In some embodiments, haloalkyl group refers to a perhaloalkyl group. In some embodiments, alkyl groups may be substituted. In some embodiments, the alkyl group may be substituted with one or more hydroxyl, amine, or ammonium groups. In other embodiments, the alkyl group may be unsubstituted.

[0014] As used herein, the terms "carboxyl" or "carboxylate" refer to the -C(O)OH group or its ionized form, -C(O)O-.

[0015] As used herein, the term "carbonyl" refers to the -C(O)- group.

[0016] As used herein, the term "hydroxyl" may refer to -OH or its ionized form, -O-.

[0017] As used herein, the term "amine" (or "amino") is defined as -NR 65 R 66 It refers to the base, R 65 and R 66This is independently hydrogen, or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, heterocyclylalkyl, or heterocyclyl group as defined herein. In some embodiments, the amine is an alkylamino, dialkylamino, arylamino, or alkylarylamino. In some embodiments, the amine is an alkylamino or dialkylamino group. In some embodiments, the amine group may be a quaternary amine, referring to an ammonium group as used herein. In some embodiments, the ammonium comprises one, two, or three alkyl groups. The alkyl group may independently comprise linear and branched alkyl groups having 1 to about 20 carbon atoms, typically 1 to 12 carbon atoms, or, in some embodiments, 1 to 8, 1 to 6, 1 to 4, 1 to 3, or 1 to 2 carbon atoms. In some embodiments, the alkyl group may be a methyl group.

[0018] Groups described herein that have two or more bonding sites (i.e., divalent, trivalent, or polyvalent) within the compounds of this technology are indicated by the use of the suffix "ene". For example, a divalent alkyl group is an alkylene group, a divalent aryl group is an arylene group, a divalent heteroaryl group is a divalent heteroarylene group, and so on. Substituents having a single bonding site to the compounds of this technology are not referred to using the designation "ene".

[0019] In one embodiment, the present technology provides compounds of formula I and / or formula II, TIFF0007866029000013.tif50128In formula, R 1 and R 5 These are H, hydroxyl, or CH3, respectively, and R 2 and R 6 These are H, hydroxyl, and CH individually. 3、 N(CH3)2, or + N(CH3)3, and Y is OR 3 or N(R 8 ) i And Z is OR 7 or N(R10 ) j And R 3 and R 7 Each is individually H or C1-C6 alkyl, and R in each appearance 8 Each is a C1-C6 alkyl which may be substituted with one or more hydroxyl groups, and R in each appearance 10 Each of these is a C1-C6 alkyl which may be substituted with H or one or more hydroxyl groups, and R 4 is H, or a C1-C6 alkyl group which may be substituted with one or more hydroxyl, amine, or ammonium groups, a, b, d, e, f, and h are individually 0 or 1, c and g are individually 0, 1, or 2, i and j are individually 2 or 3, X - It is an anion and exists in equal amounts to the cation present in formula I or formula II.

[0020] In one embodiment, the compound of formula I may be the compound of formula IA, and / or the compound of formula II may be the compound of formula IIA. TIFF0007866029000014.tif50128In formula, R 1 , R 2 , R 5 , and R 6 These are H, hydroxyl, or CH3, respectively, and R 3 and R 7 Each is individually H or C1-C6 alkyl, and R 4 is a C1-C6 alkyl group which may be substituted with H or one or more hydroxyl groups, a, b, d, e, f, and h are individually 0 or 1, and c and g are individually 0, 1, or 2, X - It is an anion.

[0021] In another embodiment, the compound of formula I may be the compound of formula IB, and / or the compound of formula II may be the compound of formula IIB. TIFF0007866029000015.tif50128In formula, R 1 and R 5These are H, hydroxyl, or CH3, respectively, and R 2 and R 6 These are H and CH individually. 3、 N(CH3)2, or + N(CH3)3, and R in each occurrence 8 Each is a C1-C6 alkyl which may be substituted with one or more hydroxyl groups, and R in each appearance 10 Each of these is a C1-C6 alkyl which may be substituted with H or one or more hydroxyl groups, and R 4 is H, or one or more hydroxyl groups, N(CH3)2, or + A C1-C6 alkyl group which may be substituted with three N(CH3) groups, where a, b, d, e, f, and h are individually 0 or 1, and c and g are individually 0, 1, or 2, X - It is an anion.

[0022] In some embodiments, c and g may be 1. In some embodiments, c and g may be 0.

[0023] In some embodiments, a and e may be 0. In some embodiments, a and e may be 1.

[0024] In some embodiments, b and f may be 0. In some embodiments, b and f may be 1.

[0025] In some embodiments, d and h may be 0. In some embodiments, d and h may be 1.

[0026] In some embodiments, a, b, c, e, f, and g are 1. In some embodiments, a, b, c, e, f, and g may be 0.

[0027] In some preferred embodiments, a+b+c≧1. In some preferred embodiments, e+f+g≧1. In some preferred embodiments, a+b+c+d≧1. In some preferred embodiments, e+f+g+h≧1. In some preferred embodiments, a+b+c+d≧2. In some preferred embodiments, e+f+g+h≧2. In some preferred embodiments, a+b+c+d≧3. In some preferred embodiments, e+f+g+h≧3.

[0028] In some embodiments, a, b, e, and f may be 0, c and g may be 2, and d and h may be 1.

[0029] In some embodiments, a, b, e, and f may be 0, and c, d, g, and h may be 1.

[0030] In some embodiments, a, b, d, e, f, and h may be 1, and c and g may be 0.

[0031] In some embodiments, a, b, d, e, f, and h may be 0, and c and g may be 1.

[0032] In some embodiments, a, b, c, e, f, and g may be 0, and d and h may be 1.

[0033] In some embodiments, a, d, e, and h may be 0, and b, c, f, and g may be 1.

[0034] In some embodiments, a, b, d, e, f, and h may be 0, and c and g may be 1.

[0035] In some embodiments, R 1 and R 5 R can be hydroxyl or CH3, respectively. In some embodiments, 1 and R 5This can be H or CH3. In some embodiments, R 1 and R 5 This can be H. In some embodiments, R 1 and R 5 This could be CH3.

[0036] In some embodiments, R 3 and R 7 This can be H. In some embodiments, R 3 and R 7 These can be C1-C6 alkyl groups individually. In some embodiments, R 3 and R 7 These can be C1-C4 alkyl groups individually. In some embodiments, R 3 and R 7 These can be C1-C3 alkyl groups individually. In some embodiments, R 3 and R 7 These can be C1-C2 alkyl groups individually. In some embodiments, R 3 and R 7 This could be CH3.

[0037] In some embodiments, R 4 R can be H, or a C1-C6 alkyl group which may be substituted with one or more hydroxyl groups. In some embodiments, R 4 R may be a C1-C6 alkyl group which may be substituted with one or more hydroxyl groups. In some embodiments, R 4 R may be a C1-C4 alkyl group which may be substituted with one or more hydroxyl groups. In some embodiments, R 4 R may be a C1-C3 alkyl group which may be substituted with one or more hydroxyl groups. In some embodiments, R 4 R may be a C1-C2 alkyl group which may be substituted with one or more hydroxyl groups. In some embodiments, R 4 R may be a methyl group which may be substituted with one or more hydroxyl groups. In some embodiments, R 4R can be substituted with one or more hydroxyl groups. In some embodiments, R 4 R can be terminally substituted with one or more hydroxyl groups. In some embodiments, R 4 R can be substituted with two or more hydroxyl groups. In some embodiments, R 4 R can be terminally substituted with one of two or more hydroxyl groups. In some embodiments, R 4 This can be a CH2CH(CH3)OH group. In some embodiments, R 4 R can be substituted with one or more halide groups. In some embodiments, R 4 R can be substituted with two or more halide groups. In some embodiments, R 4 R can be substituted with one or more hydroxyl groups and one or more halide groups. In some embodiments, R 4 R can be substituted with one or more hydroxyl groups instead of any halide group. In some embodiments, R 4 R can be substituted with one or more halide groups instead of any hydroxyl group. In some embodiments, R 4 R may be H, or a C1-C6 alkyl group which may be substituted with one or more amine or ammonium groups. In some embodiments, 4 R may be a C1-C6 alkyl group which may be substituted with one or more amine or ammonium groups. In some embodiments, 4 R may be a C1-C4 alkyl group which may be substituted with one or more amine or ammonium groups. In some embodiments, R 4 R may be a C1-C3 alkyl group which may be substituted with one or more amine or ammonium groups. In some embodiments, R 4 R may be a C1-C2 alkyl group which may be substituted with one or more amine or ammonium groups. In some embodiments, R 4 R may be a methyl group which may be substituted with one or more amine or ammonium groups. In some embodiments, R 4 is one or more +It may be an alkyl group substituted with three N(C1-C2 alkyl) groups. In some embodiments, R 4 is one or more + It may be an alkyl group substituted with an N(CH3)3 group. In some embodiments, R 4 is one or more + It may be an alkyl group substituted with two NH(CH3) groups. In some embodiments, R 4 is one or more + It may be an alkyl group substituted with an NH2(CH3) group. In some embodiments, R 4 is one or more + It may be an alkyl group substituted with an NH3 group. In some embodiments, R 4 is one or more + In some embodiments, R 4 is 1 + It can be substituted with N(CH3)3 groups. In some embodiments, R 4 CH2C(CH3)2-N(CH3)3 + It could be the basis.

[0038] In some embodiments, R 2 and R 6 is H, hydroxyl, CH3, N(CH3)2, or + In some embodiments, R 2 and R 6 H is H. In some embodiments, R 2 and R 6 R is hydroxyl. In some embodiments, R 2 and R 6 is CH3. In some embodiments, R 2 and R 6 is N(CH3)2 or + It is N(CH3)3.

[0039] In some embodiments, i is 2. In some embodiments, j is 2 or 3. In some embodiments, j is 3.

[0040] Several embodiments, R in each occurrence 8 and R 10 These are C1-C6 alkyl groups, which may be individually substituted with one or more hydroxyl groups. In some embodiments, R in each occurrence 8 and R 10 These are C1-C4 alkyl groups which may be individually substituted with one or more hydroxyl groups. In some embodiments, R in each occurrence 8 and R 10 These are, individually, a C1-C4 alkyl group substituted with one hydroxyl group or CH3. In some embodiments, R in each occurrence 8 and R 10 They are the same. In some embodiments, R in each occurrence 8 and R 10 This is CH3. In some embodiments, R appears twice. 8 and R 10 They are the same. In some embodiments, two R 8 and two R 10 It is CH3, and R 8 and R 10 The third appearance of is a C1-C4 alkyl substituted with one hydroxyl group. In some embodiments, one R 8 and two R 10 It is CH3, and R 8 and R 10 The remaining appearances are C1-C4 alkyl groups substituted with one hydroxyl group. In some embodiments, R 8 and R 10 The R is selected from the group consisting of CH3 and C(CH3)2CH2OH. In some embodiments, two R 8 and two R 10 This is CH3, and the third R 8 and R 10 This is a C(CH3)2CH2OH group. In some embodiments, one R 8 and two R 10 It is CH3, and the remaining R 8 and R 10This is a C(CH3)2CH2OH group. In some embodiments, R 8 These are CH3 and C(CH3)2CH2OH, and R 10 These are CH3, CH3, and C(CH3)2CH2OH. In some embodiments, R in each occurrence 8 and R 10 This is CH3.

[0041] In some embodiments, i is 2. In some embodiments, j is 2 or 3. In some embodiments, j is 3.

[0042] X - is an anion and is present in an amount equal to the cation present in formula I and / or formula II. In some embodiments, formula I may not have any cation, and X - It does not exist as a counter anion. In some embodiments, formula II may have 1, 2, or 3 cations, X - It exists as an anion with an amount equal to the amount of cation charge. In some embodiments, X - X may be a halide, sulfate ion, metosulfate, carbonate ion, carboxylate ion, phosphate ion, or hydroxide ion. In some embodiments, X - X can be a halide or a hydroxide ion. In some embodiments, X - This could be a hydroxide ion.

[0043] In some embodiments, the composition comprises a compound of formula IA.

[0044] In some embodiments, the compound of formula IA is Includes TIFF0007866029000016.tif243160TIFF0007866029000017.tif129135 or any combination of two or more of them.

[0045] In some embodiments, the composition of the compound of formula IA includes DMTA, DMAMPD, DMAEPD, DMMOPA, iso-DMTA, iso-DMAMPD, iso-DMAEPD, iso-DMAMP, or a combination of two or more thereof. In some embodiments, the composition of the compound of formula IA includes DMAMPD, iso-DMAMPD, or a combination thereof. In some embodiments, the composition of the compound of formula IA is DMAMPD.

[0046] In some preferred embodiments, the composition comprises a compound of formula IIA.

[0047] In some embodiments, the compound of formula IIA is Includes TIFF0007866029000018.tif78132, TIFF0007866029000019.tif157138, or any combination of two or more of these.

[0048] In some embodiments, the compound of formula IIA includes DMTA-AH, DMAMPD-AH, DMAEPD-AH, DMMOPA-AH, iso-DMTA-AH, iso-DMAMPD-AH, iso-DMAEPD-AH, iso-DMAMP-AH, or a combination of two or more thereof. In some embodiments, the compound of formula II includes DMAMP-AH, iso-DMAEPD-AH, or a combination thereof. In some embodiments, the compound of formula IIA includes DMAMPD-AH, iso-DMAMPD-AH, or a combination thereof. In some embodiments, the compound of formula IIA includes DMAMPD-AH.

[0049] In some preferred embodiments, the composition comprises a compound of formula IB.

[0050] In some embodiments, the compound of formula IB is Includes TIFF0007866029000020.tif136147 or two or more combinations thereof.

[0051] In some preferred embodiments, the composition comprises a compound of formula IIB.

[0052] In some embodiments, the compound of formula IIB is Includes TIFF0007866029000021.tif180128 or two or more combinations thereof.

[0053] In some embodiments, the composition has about 0.1% to about 80% by weight of a compound of formula I and / or formula II (including formulas IA, IIA, IB, and / or IIB) based on the total composition. In some embodiments, the composition has about 1% to about 50% by weight of a compound of formula I and / or formula II (including formulas IA, IIA, IB, and / or IIB) based on the total composition. In some embodiments, the composition has about 0.1% to about 80% by weight of a compound of formula II (including formulas IIA and / or IIB) based on the total composition. In some embodiments, the composition has about 1% to about 50% by weight of a compound of formula II (including formulas IIA and / or IIB) based on the total composition.

[0054] In some embodiments, the composition may be an electronic equipment processing composition (e.g., a semiconductor processing composition), a cleaning composition, a stripping composition, a degreasing composition, a catalyst, a phase transfer agent, or a combination of two or more thereof. In some embodiments, the electronic equipment processing composition may be a wafer cleaning composition, an anisotropic etching composition, a photolithography composition, a photoresist developing composition, a post-chemoplanarization cleaning composition, a printed circuit board cleaning composition, or a combination of two or more thereof.

[0055] In some embodiments, the composition further comprises stabilizers (e.g., antioxidants, oxygen scavengers, or reducing agents, such as dithionite salts, amines, hydroxylamines, sulfites, hydroquinones, hydrides, carboxylic acids, piperazines, formaldehyde, thiourea, borates, butylated hydroxytoluene, butylated hydroxyanisole, ascorbic acid, and two or more combinations thereof).

[0056] In some embodiments, the composition further comprises a rust inhibitor. In any embodiment, the rust inhibitor may include sugars, alcoholic sugars, pyrocatechol, and / or butylcatechol. Non-limiting examples of sugars or alcoholic sugars include arabinose, galactose, xylitol, sorbitol, mannitol, mannose, glucose, lactose, maltol, maltose, inositol, xylose, ribose, trehalose, sucrose, fructose, and polydextrose.

[0057] In some embodiments, the composition further comprises an alcohol, pyrocatechol, glycerin, and / or a glycerin derivative.

[0058] In some embodiments, the compound of formula I and / or the compound of formula II (including formulas IA, IIA, IB, and / or IIB) is an etching agent. In some embodiments, the compound of formula II is an etching agent.

[0059] In some embodiments, the composition further comprises hydroxylamines (e.g., hydroxylamine, hydroxylamine sulfate, hydroxylamine chloride, hydroxylamine oxalate, N,N-diethylhydroxylamine, isopropylhydroxylamine, dimethylhydroxylamine hydrochloride, and / or hydroxylamine phosphate).

[0060] In some embodiments, the composition further comprises an inorganic alkali compound (e.g., sodium hydroxide, potassium hydroxide, ammonia, and hydrated hydrazine).

[0061] In some embodiments, the composition further includes water.

[0062] In some embodiments, the composition further comprises a hydrotropic component (e.g., cumenesulfonic acid, tetramethylammonium cumenesulfonate, tetramethylammonium xylenesulfonate, tetramethylammonium phenolsulfonate, tetramethylammonium toluenesulfonate, and / or tetramethylammonium benzenesulfonate).

[0063] In some embodiments, the composition further comprises pH adjusters, buffers, or combinations thereof (e.g., amines, amino alcohols, hydroxylamines, amine oxides, organic hydroxides, phosphates, carbonates, and two or more combinations thereof).

[0064] In some embodiments, the composition further comprises at least one organic solvent or surfactant (e.g., DMSO, alcohol, ethoxylated alcohol, betaine, alkyl sulfonic acid, aryl sulfonic acid, or two or more combinations thereof).

[0065] In some embodiments, the composition further comprises a rheology modifier (e.g., a polymer rheology modifier such as polyacrylic acid).

[0066] In some embodiments, the composition further comprises a chelating agent (e.g., ethylenediaminetetraacetic acid ("EDTA")).

[0067] In some embodiments, the composition contains a metal selected from the group consisting of Na, Mg, Al, K, Ca, Mn, Fe, Ni, Cu, Zn, Ag, Pd, and Cr, in a maximum of about 1000 ppb.

[0068] In some embodiments, the composition has reduced toxicity compared to a composition containing the same wt% tetramethylammonium hydroxide (TMAH), based on rat skin toxicity.

[0069] In some embodiments, the composition may not contain TMAH in any way. As used herein, “in any way” means not containing TMAH in amounts less than about 5% by weight, less than about 4% by weight, less than about 3% by weight, less than about 2% by weight, less than about 1% by weight, less than about 0.5% by weight, less than about 0.1% by weight, less than about 0.05% by weight, less than about 0.01% by weight, or any detectable amount.

[0070] In another embodiment, the Art provides a process for preparing a composition comprising a compound of Formula II provided herein. The process may include providing a solution comprising a compound of Formula I according to any one of claims 1 to 35 and an organic solvent (e.g., isopropyl alcohol); optionally heating the solution to about 25°C to about 45°C; adding a methylating agent (e.g., methyl iodide) to the solution to produce a mixture, wherein the methylating agent is optionally added over a period of about 1 hour; mixing the mixture (e.g., stirring); optionally cooling the mixture to below about 20°C (e.g., 10°C); and optionally filtering the mixture (e.g., using an ion exchange resin filter).

[0071] In another embodiment, the Art provides compounds of formula I or formula II (including formulas IA, IIA, IB, and / or IIB) as provided herein.

[0072] In some embodiments, the compound of formula I is a compound of formula IA or formula IB: TIFF0007866029000022.tif224153TIFF0007866029000023.tif208156 or two or more combinations thereof. In some embodiments, the compound of formula I includes DMTA, DMAMPD, DMAEPD, DMMOPA, iso-DMTA, iso-DMAMPD, iso-DMAEPD, iso-DMAMP, PMPDA, TMPDA, HMPTA, HPMAMP, or two or more combinations thereof. In some embodiments, the compound of formula I includes DMTA, DMAEPD, DMMOPA, iso-DMTA, iso-DMAMPD, DMAMPD, iso-DMAEPD, iso-DMAMP, PMPDA, TMPDA, HMPTA, HPMAMP, or two or more combinations thereof. In some embodiments, the compound of formula I includes DMAMPD, iso-DMAMPD, or a combination thereof. In some embodiments, the compound of formula I includes DMAMPD.

[0073] In some embodiments, compounds of formula I (including formulas IA and IB) Does not include TIFF0007866029000024.tif189164.

[0074] In some embodiments, the compound of formula II is the compound of formula IIA or formula IIB: TIFF0007866029000025.tif94140TIFF0007866029000026.tif234124 or two or more combinations thereof. In some embodiments, the compound of formula II includes DMTA-AH, DMAMPD-AH, DMAEPD-AH, DMMOPA-AH, iso-DMTA-AH, iso-DMAMPD-AH, iso-DMAEPD-AH, iso-DMAMP-AH, PMPDA-AH, TMPDA-AH, HMPTA-AH, HPMAMP-AH, or two or more combinations thereof. In some embodiments, the compound of formula II includes DMAMP-AH, iso-DMAEPD-AH, or combinations thereof. In some embodiments, the compound of formula II includes DMAMPD-AH, iso-DMAMPD-AH, or combinations thereof. In some embodiments, the compound of formula II includes DMAMPD-AH.

[0075] In some embodiments, the compound of formula II (including formulas IIA and IIB) Excluding TIFF0007866029000027.tif152156, In the formula, X - This is as defined herein.

[0076] Therefore, the generally described invention will be more readily understood by referring to the following embodiments, which are provided for illustrative purposes and are not intended to limit the invention. [Examples]

[0077] Example 1. Synthesis of DMAMP-iodide. To a solution of 147 g (1.00 mol) of DMAMP-80 (ANGUS Chemical Company) and 580 g of isopropyl alcohol (99%, VWR International), 145 g (1.02 mol) of methyl iodide (99%, Aldrich Chemical Company) was gradually added over 60 minutes while maintaining the internal temperature at 25°C to 45°C. After the addition was complete, the mixture was stirred at ambient temperature for 3 hours, and then cooled at 10°C for 1 hour. The mixture was pressure filtered under nitrogen. The filtered cake was washed with 500 g of isopropyl alcohol and then dried under vacuum to a constant weight. The product was a white solid weighing 242 g (94% yield).

[0078] Example 2. Synthesis of DMAMP-AH. DMAMP-iodide from Example 1 was subjected to ion-exchange chromatography. A 3x60cm glass column with a bed volume of 350mL was used. The column was packed with AMBERLITE® IRA410 Cl (Fisher Scientific) and deionized water. The column was prepared by rinsing the resin with 2 bed volumes of deionized water at a rate of 20mL / min. The resin was activated by pumping 2 bed volumes of 8 wt% aqueous sodium hydroxide at a rate of 2mL / min. The resin was rinsed with 6 bed volumes of deionized water to produce a neutral eluate. 100g of DMAMP-iodide was dissolved in 260g of deionized water and packed into the column at a rate of 2mL / min. The eluate was collected when the pH exceeded 10 (determined using ColorpHast pH strips, EMD / Merck). Approximately 3 bed volumes were collected. The product was concentrated at less than 20 mmHg and less than 35°C to obtain 125 mL of a yellow liquid. The product did not contain iodide detectable by the peroxide / cellulose test. The product contained 44% by weight of solid by HCl titration with bromocresol purple indicator.

[0079] Example 3. Synthesis of 3-methoxy-N,N,N-trimethylpropane-1-ammonium hydroxide. To a solution of 117.2 g (1.00 mol) of N,N-dimethyl-3-methoxypropylamine (DMMOPA) (99%, ANGUS Chemical Company) and 520 g of isopropyl alcohol (99%, VWR International), 145 g (1.02 mol) of methyl iodide (99%, Aldrich Chemical Company) was gradually added over 90 minutes while maintaining the internal temperature at 25°C to 45°C. After the addition was complete, the mixture was stirred at ambient temperature for 4 hours. The mixture was pressure filtered under nitrogen. The filtered cake was washed twice with 200 g of isopropyl alcohol and then dried under vacuum to a constant weight to provide 3-methoxy-N,N,N-trimethylpropane-1-ammonium iodide. 3-Methoxy-N,N,N-trimethylpropane-1-ammonium iodide was a colorless solid weighing 250.0 g (96.9% yield). 1 The 1H NMR (D2O) was consistent with the assigned structure.

[0080] 3-methoxy-N,N,N-trimethylpropane-1-ammonium iodide was dissolved in a minimal amount of water and converted to 3-methoxy-N,N,N-trimethylpropane-1-ammonium hydroxide according to the procedure in Example 2.

[0081] Example 4. Synthesis of 1,3-dihydroxy-N,N,N,2-tetramethylpropane-2-ammonium hydroxide. 490 g (3.45 mol) of methyl iodide (99%, Aldrich Chemical Company) was gradually added over 70 minutes while maintaining an internal temperature of 25°C to 45°C to a solution of 600 g (2.70 mol) of 2-(dimethylamino)-2-methylpropane-1,3-diol (DMAMPD) (60% aqueous, ANGUS Chemical Company) and 1000 g of isopropyl alcohol (99%, VWR International). After the addition was complete, the mixture was stirred at ambient temperature for 4 hours. The mixture was cooled at 5°C for 16 hours. The liquid layer was decanted under nitrogen. The solid was washed with 600 g of isopropyl alcohol and subsequently decanted. The solid was dried under vacuum to a constant weight to provide 1,3-dihydroxy-N,N,N,2-tetramethylpropane-2-ammonium iodide. 1,3-dihydroxy-N,N,N,2-tetramethylpropane-2-ammonium iodide was a colorless solid weighing 562 g (75.9% yield). 1 The 1H NMR (D2O) was consistent with the assigned structure.

[0082] 1,3-dihydroxy-N,N,N,2-tetramethylpropane-2-ammonium iodide was dissolved in a minimal amount of water and converted to 1,3-dihydroxy-N,N,N,2-tetramethylpropane-2-ammonium hydroxide according to the procedure in Example 2.

[0083] Example 5. Synthesis of 1,3-dihydroxy-N,N,N,2-tetramethylpropane-2-ammonium hydroxide. To a solution of 212 g (0.955 mol) of 2-(dimethylamino)-2-methylpropane-1,3-diol (DMAMPD) (60% aqueous solution, ANGUS Chemical Company), 70 g (1.4 mol) of methyl chloride (99.5+%, Aldrich Chemical Company) was added in a 1 L Parr reactor. The mixture was heated to 60°C at a pressure of 114 psi. The mixture was stirred at 60°C for 4 hours, after which the amine was completely consumed as determined by colorimetric titration with hydrochloric acid. The reactor was evacuated to atmospheric pressure and then pressure-purged three times with nitrogen at 20 psi. The mixture was cooled to room temperature to provide 1,3-dihydroxy-N,N,N,2-tetramethylpropane-2-ammonium chloride as a pale yellow liquid. 1 The 1H NMR (D2O) was consistent with the assigned structure.

[0084] 1,3-dihydroxy-N,N,N,2-tetramethylpropane-2-ammonium chloride was dissolved in a minimal amount of water and converted to 1,3-dihydroxy-N,N,N,2-tetramethylpropane-2-ammonium hydroxide according to the procedure in Example 2.

[0085] Example 6. Synthesis of 2-hydroxy-2-(hydroxymethyl)-N,N,N-trimethylbutane-1-ammonium hydroxide. To a solution of 100 g (0.68 mol) of 2-((dimethylamino)methyl)butane-1,2-diol (iso-DMAEPD) (ANGUS Chemical Company) and 100 g of isopropyl alcohol (99%, VWR International), 100 g (0.70 mol) of methyl iodide (99%, Aldrich Chemical Company) was gradually added over 30 minutes while maintaining the internal temperature at 25°C to 45°C. After the addition was complete, the mixture was stirred at ambient temperature for 2 hours. The mixture was concentrated to dryness under vacuum at 40°C. The resulting oil was solidified under vacuum for 4 hours. The resulting solid was pulverized with 100 g of isopropyl alcohol and then filtered under nitrogen. The solid was dried under vacuum to a certain weight to provide 2-hydroxy-2-(hydroxymethyl)-N,N,N-trimethylbutane-1-ammonium iodide. 2-hydroxy-2-(hydroxymethyl)-N,N,N-trimethylbutane-1-ammonium iodide was a colorless solid weighing 164 g (82% yield). 1 The 1H NMR (D2O) was consistent with the assigned structure.

[0086] 2-hydroxy-2-(hydroxymethyl)-N,N,N-trimethylbutane-1-ammonium iodide was dissolved in a minimal amount of water and converted to 2-hydroxy-2-(hydroxymethyl)-N,N,N-trimethylbutane-1-ammonium hydroxide according to the procedure in Example 2.

[0087] Exemplary Embodiments Item 1. A compound of formula I or formula II, TIFF0007866029000028.tif50128In formula, R 1 and R 5 However, individually, H, hydroxyl, or CH3, and R 2 and R 6 However, individually, H, hydroxyl, CH 3、 N(CH3)2, or +N(CH3)3, and Y is OR 3 or N(R 8 ) i And Z is OR 7 or N(R 10 ) j And R 3 and R 7 However, individually, they are H or C1-C6 alkyl, and R in each appearance 8 However, each C1-C6 alkyl group may be individually substituted with one or more hydroxyl groups, and R in each appearance 10 However, each C1-C6 alkyl group may be individually substituted with one or more hydroxyl groups, and R 4 is a C1-C6 alkyl group which may be substituted with H or one or more hydroxyl, amine, or ammonium groups, and a, b, d, e, f, and h are individually 0 or 1, c and g are individually 0, 1, or 2, and i and j are individually 2 or 3, X - A compound in which the anion is present in an equal amount to the cation present in formula I or formula II.

[0088] Item 2. The compound of formula I is the compound of formula IA, and / or the compound of formula II is the compound of formula IIA. TIFF0007866029000029.tif50128In formula, R 1 , R 2 , R 5 , and R 6 However, individually, H, hydroxyl, or CH3, and R 3 and R 7 However, individually, they are H or C1-C6 alkyl, and R 4 is a C1-C6 alkyl group which may be substituted with H or one or more hydroxyl groups, and a, b, d, e, f, and h are individually 0 or 1, and c and g are individually 0, 1, or 2, X - However, it is an anion, the compound of item 1.

[0089] Item 3. The compound of formula I is the compound of formula IB, and / or the compound of formula II is the compound of formula IIB. TIFF0007866029000030.tif50128In formula, R 1 and R 5 However, individually, H, hydroxyl, or CH3, and R 2 and R 6 However, individually, H, CH 3、 N(CH3)2, or + N(CH3)3, and R in each occurrence 8 However, each C1-C6 alkyl group may be individually substituted with one or more hydroxyl groups, and R in each appearance 10 However, each C1-C6 alkyl group may be individually substituted with one or more hydroxyl groups, and R 4 However, H, or one or more hydroxyl groups, N(CH3)2, or + A C1-C6 alkyl group which may be substituted with three N(CH3) groups, where a, b, d, e, f, and h are individually 0 or 1, and c and g are individually 0, 1, or 2, X - However, it is an anion, the compound of item 1.

[0090] One of the compounds from items 1-3, wherein c and g are 1.

[0091] One of the compounds from items 1-3, where item 5.c and g are 0.

[0092] One of the compounds from items 1 to 5, where items 6.a and e are 0.

[0093] One compound from any of items 1-5, wherein items 7.a and e are 1.

[0094] One of the compounds from items 1-7, where items 8.b and f are 0.

[0095] One compound from items 1-7, wherein items 9.b and f are 1.

[0096] Item 10. One of the compounds from items 1 to 9, where d and h are 0.

[0097] Item 11. One of the compounds from items 1 to 9, where d and h are 1.

[0098] Item 12. One compound from any of items 1-3, where a, b, c, e, f, and g are 1.

[0099] Item 13. Any one of the compounds from items 1-3, where a, b, c, e, f, and g are 0.

[0100] Item 14. One of the compounds from items 1 to 13, where a + b + c + d ≥ 1.

[0101] Item 15. One of the compounds from items 1 to 14, where a+b+c+d≧2.

[0102] Item 16. One of the compounds from items 1 to 15, where e + f + g + h ≥ 1.

[0103] Item 17. One of the compounds from items 1 to 16, where e + f + g + h ≥ 2.

[0104] Item 18. One compound from any of items 1-3, where a, b, e, and f are 0 and c, d, g, and h are 1.

[0105] Item 19. Any one of the compounds from items 1 to 3, where a, b, d, e, f, and h are 1 and c and g are 0, or a, b, d, e, f, and h are 0 and c and g are 1.

[0106] Item 20. Any one of the compounds from items 1-3, where a, b, c, e, f, and g are 0, and d and h are 1.

[0107] Item 21. Any one of the compounds from items 1 to 3, where a, d, e, and h are 0 and b, c, f, and g are 1.

[0108] Item 22. Any one of the compounds from items 1 to 3, where a, b, d, e, f, and h are 0, and c and g are 1.

[0109] Item 23. One of the compounds from items 1-3, where a, b, e, and f are 0, c and g are 2, and d and h are 1.

[0110] Section 24.R 1 and R 5 However, individually, one of the compounds from items 1 to 23, which is either hydroxyl or CH3.

[0111] Section 25.R 1 and R 5 A compound from any one of items 1-23, wherein the compound is either H or CH3.

[0112] Section 26.R 1 and R 5 However, it is one of the compounds listed in items 1 to 25, which is CH3.

[0113] Section 27.R 3 and R 7 A compound that is H, one of the compounds listed in items 1 to 26.

[0114] Section 28.R 3 and R 7 However, individually, one of the compounds from items 1 to 26, which is a C1-C6 alkyl group.

[0115] Section 29.R 3 and R 7 However, individually, the compounds in item 28 are C1-C4 alkyl.

[0116] Section 30.R 3 and R 7 However, individually, the compounds of item 28 or item 29 are C1-C3 alkyl.

[0117] Section 31.R 3 and R 7 However, individually, one of the compounds from items 28-30, which is a C1-C2 alkyl group.

[0118] Item 32. R 3 and R 7 is CH3, a compound of any one of Items 28 to 31.

[0119] Item 33. R 4 is a C1-C4 alkyl group optionally substituted with one or more hydroxyl groups, a compound of any one of Items 1 to 32.

[0120] Item 34. R 4 is a C1-C3 alkyl group optionally substituted with one or more hydroxyl groups, the compound of Item 33.

[0121] Item 35. R 4 is a C1-C2 alkyl group optionally substituted with one or more hydroxyl groups, the compound of Item 33 or Item 34.

[0122] Item 36. R 4 is a methyl group optionally substituted with one or more hydroxyl groups, a compound of any one of Items 33 to 35.

[0123] Item 37. R 4 is substituted with one or more hydroxyl groups, a compound of any one of Items 1 to 36.

[0124] Item 38. R 4 is terminally substituted with one or more hydroxyl groups, the compound of Item 37.

[0125] Item 39. R 4 is substituted with two or more hydroxyl groups, a compound of any one of Items 1 to 38.

[0126] Item 40. R 4 is terminally substituted with one of two or more hydroxyl groups, the compound of Item 39.

[0127] Item 41. R 4However, it is one of the compounds listed in items 1 to 34, which is CH2CH(CH3)OH.

[0128] Section 42.R 4 A compound from any one of items 1 to 32, wherein the C1-C4 alkyl group may be substituted with one or more amine or ammonium groups.

[0129] Section 43.R 4 The compound of item 42, wherein the C1-C3 alkyl group is substituted with one or more amine or ammonium groups.

[0130] Section 44.R 4 The compound of item 42 or item 43, wherein the C1-C2 alkyl group is substituted with one or more amine or ammonium groups.

[0131] Section 45.R 4 A compound from any one of items 42 to 44, wherein the methyl group is substituted with one or more amine or ammonium groups.

[0132] Section 46.R 4 However, one of the compounds from items 1 to 45, which is substituted with one or more amine or ammonium groups.

[0133] Section 47.R 4 However, one or more + The compound described in item 46, which is terminally substituted with an N(CH3)3 group.

[0134] Section 48.R 4 However, CH2C(CH3)2-N(CH3)3 + The compound of item 46 or item 47.

[0135] Section 49.R 2 and R 6 A compound that is H, one of the compounds listed in items 1 to 48.

[0136] Section 50.R 2 and R 6The compound according to any one of items 1 to 48, wherein it is hydroxyl.

[0137] Item 51. R 2 and R 6 The compound according to any one of items 1 to 48, wherein it is CH3.

[0138] Item 52. R 2 and R 6 The compound according to any one of items 1 to 48, wherein it is N(CH3)2 or + N(CH3)3.

[0139] Item 53. The compound according to any one of items 1 to 52, wherein i is 2.

[0140] Item 54. The compound according to any one of items 1 to 53, wherein j is 2 or 3.

[0141] Item 55. The compound according to any one of items 1 to 54, wherein j is 3.

[0142] Item 56. R in each occurrence 8 and R 10 The compound according to any one of items 1 to 55, wherein each is C1-C4 alkyl optionally substituted with one or more hydroxyl groups.

[0143] Item 57. R in each occurrence 8 and R 10 The compound according to any one of items 1 to 55, wherein each is C1-C4 alkyl substituted with one hydroxyl group or CH3.

[0144] Item 58. R in each occurrence 8 and R 10 The compound according to any one of items 1 to 57, wherein they are the same.

[0145] Item 59. R in two occurrences 8 and R 10 The compound according to any one of items 1 to 58, wherein they are the same.

[0146] Item 60. R in each occurrence 8 and R 10 However, it is one of the compounds listed in items 1 to 59, which is CH3.

[0147] 61.2 occurrences of R 8 and R 10 However, it is CH3, and R appears for the third time. 8 and R 10 However, it is a compound of item 59, which has a C(CH3)2CH2OH group. 8 and R 10 However, the compound of item 59 is selected from the group consisting of CH3 and C(CH3)2CH2OH. 8 However, these are CH3 and C(CH3)2CH2OH, and R 10 The compound of item 59, which is CH3, CH3, and C(CH3)2CH2OH.

[0148] Section 62.X - The compound is one of the compounds listed in items 1 to 61, which is a halide, sulfate ion, metosulfate, carbonate ion, carboxylate ion, phosphate ion, or hydroxide ion.

[0149] Section 63.X - A compound from any one of items 1 to 62, which is a halide or a hydroxide ion.

[0150] Section 64.X - However, one of the compounds listed in items 1 to 63, which is a hydroxide ion.

[0151] Section 65. The compound of formula I, One compound of formula IA selected from the group consisting of TIFF0007866029000031.tif135169TIFF0007866029000032.tif252150 and two or more combinations thereof, which is one compound from any of items 1 to 64.

[0152] Item 66. A compound of Item 66, wherein the compound of Formula I is a compound of Formula IA selected from the group consisting of DMTA, DMAMPD, DMAEPD, DMMOPA, iso-DMTA, iso-DMAMPD, iso-DMAEPD, iso-DMAMP, and two or more combinations thereof. A compound of Item 66, wherein the compound of Formula I is a compound of Formula IA, which is DMAMPD.

[0153] Section 67. The compound of formula II, One compound of formula IIA selected from the group consisting of TIFF0007866029000033.tif179132TIFF0007866029000034.tif53138 and two or more combinations thereof, which is one of the compounds from items 1 to 66.

[0154] Item 68. The compound of Item 67, wherein the compound of Formula IIA is selected from the group consisting of DMTA-AH, DMAMPD-AH, DMAEPD-AH, DMMOPA-AH, iso-DMTA-AH, iso-DMAMPD-AH, iso-DMAEPD-AH, iso-DMAMP-AH, or two or more combinations thereof. The composition of Item 68, wherein the compound of Formula IIA is DMAMPD-AH.

[0155] Section 69. The compound of formula I, One compound from any of items 1 to 68, which is a compound of formula IB selected from the group consisting of TIFF0007866029000035.tif150157 and two or more combinations thereof.

[0156] Section 70. The compound of formula II, One compound from items 1 to 69, which is a compound of formula IIB selected from the group consisting of TIFF0007866029000036.tif125128 and two or more combinations thereof.

[0157] Item 71. A composition comprising a compound of formula I (including formula IA and / or IB) as described in any one of items 1 to 70, a compound of formula II (including formula IIA and / or IIB), or a combination thereof.

[0158] Item 72. The composition of Item 71, having, based on the whole composition, about 0.1% to about 80% by weight of a compound of Formula I, a compound of Formula II, or a combination thereof.

[0159] Item 73. The composition of item 71 or 72, having, based on the whole composition, about 1% to about 50% by weight of a compound of formula I, a compound of formula II, or a combination thereof.

[0160] Item 74. Any one of the compositions in items 71 to 73, which is an electronic equipment processing composition (e.g., a semiconductor processing composition), a cleaning composition, a stripping composition, a degreasing composition, a catalyst, a phase transfer agent, or a combination of two or more thereof.

[0161] Item 75. The composition of 74 wherein the electronic equipment processing composition is a wafer cleaning composition, an anisotropic etching composition, a photolithography composition, a photoresist developing composition, a post-chemical mechanical planarization cleaning composition, a printed circuit board cleaning composition, or a combination of two or more thereof.

[0162] Item 76. Any one composition of items 71 to 75, further comprising a stabilizer (e.g., antioxidant, oxygen scavenger, or reducing agent, e.g., dithionite salt, amine, hydroxylamine, sulfite, hydroquinone, hydride, carboxylic acid, piperazine, formaldehyde, thiourea, borate, butylated hydroxytoluene, butylated hydroxyanisole, ascorbic acid, etc., and two or more combinations thereof).

[0163] Item 77. A composition from any one of items 71 to 76, further comprising a rust inhibitor.

[0164] Item 78. Any one composition from items 71 to 77, further comprising an alcohol, pyrocatechol, glycerin, and / or a glycerin derivative.

[0165] Item 79. A composition according to any one of items 71 to 78, wherein the compound of formula I and / or the compound of formula II is an etching agent.

[0166] Item 80. Any one composition from items 71 to 79, further comprising hydroxylamine (e.g., hydroxylamine, hydroxylamine sulfate, hydroxylamine chloride, hydroxylamine oxalate, N,N-diethylhydroxylamine, isopropylhydroxylamine, dimethylhydroxylamine hydrochloride, and / or hydroxylamine phosphate).

[0167] Item 81. Any one of the compositions from items 71 to 80, further comprising an inorganic alkali compound (e.g., sodium hydroxide, potassium hydroxide, ammonia, and hydrated hydrazine).

[0168] Item 82. Any one of the compositions from items 71 to 81, further comprising water.

[0169] Item 83. Any one of items 71 to 82, further comprising a hydrophobic component (e.g., cumenesulfonic acid, tetramethylammonium cumenesulfonate, tetramethylammonium xylenesulfonate, tetramethylammonium phenolsulfonate, tetramethylammonium toluenesulfonate, and / or tetramethylammonium benzenesulfonate).

[0170] Item 84. Any one composition from items 71 to 83, further comprising a pH adjuster, a buffer, or a combination thereof (e.g., amines, amino alcohols, hydroxylamines, amine oxides, organic hydroxides, phosphates, carbonates, and combinations of two or more thereof).

[0171] Item 85. Any one composition from items 71 to 84, further comprising at least one organic solvent or surfactant (e.g., DMSO, alcohol, ethoxylated alcohol, betaine, alkyl sulfonic acid, aryl sulfonic acid, or a combination of two or more thereof).

[0172] Item 86. Any one of the compositions from items 71 to 85, further comprising a rheological modifier (e.g., a polymer rheological modifier such as polyacrylic acid).

[0173] Item 87. Any one of the compositions from items 71 to 86, further comprising a chelating agent (e.g., ethylenediaminetetraacetic acid ("EDTA")).

[0174] Item 88. Any one of the compositions from items 71 to 87, comprising a metal selected from the group consisting of Na, Mg, Al, K, Ca, Mn, Fe, Ni, Cu, Zn, Ag, Pd, and Cr, with a maximum concentration of about 1000 ppb.

[0175] Item 89. Any one of the compositions from items 71 to 88 having reduced toxicity compared to a composition containing the same wt% tetramethylammonium hydroxide (TMAH) based on rat skin toxicity.

[0176] Item 90. Any one composition from items 71 to 89 that is essentially TMAH-free.

[0177] Item 91. A process for producing a compound of formula II as described in any of items 1 to 70, comprising: providing a solution comprising a compound of formula I as described in any of items 1 to 70 and an organic solvent (e.g., isopropyl alcohol); optionally heating the solution to about 25°C to about 45°C; adding a methylating agent (e.g., methyl iodide) to the solution to produce a mixture, wherein the methylating agent is optionally added over a period of about 1 hour; mixing the mixture; optionally cooling the mixture to less than about 20°C (e.g., 10°C); and optionally filtering the mixture (e.g., using an ion exchange resin filter).

[0178] While specific embodiments have been described and explained, it should be understood that modifications and alterations can be made to them in accordance with the ordinary art in the art, without departing from the broader aspects of the art as defined in the attached claims.

[0179] The embodiments described herein by example can be suitably implemented in the absence of any elements or limitations not specifically disclosed herein. Therefore, terms such as “comprising,” “including,” and “containing” are to be read broadly and without limitation. Furthermore, the terms and expressions used herein are for illustrative purposes only, not limitation, and the use of such terms and expressions is not intended to exclude any equivalents of the exhibited and described features or parts thereof, and it is recognized that various modifications are possible within the scope of the claimed technology. Furthermore, the phrase “essentially consisting of” is to be understood to include several elements specifically cited, and additional elements that do not substantially affect the fundamental and novel features of the claimed technology. The phrase “consisting of” excludes any elements not specified.

[0180] This disclosure is not limited to the specific embodiments described in this application. Many modifications and variations can be made without departing from the spirit and scope, as will be apparent to those skilled in the art. Functionally equivalent methods and compositions within the scope of this disclosure, in addition to those enumerated herein, will be apparent to those skilled in the art from the foregoing description. Such modifications and variations are intended to be included in the appended claims. This disclosure should be limited only by the appended claims and the entire scope of the equivalents to which such claims are granted. It should be understood that this disclosure is not limited to any particular methods, reagents, compound compositions, or biological systems, which may, of course, vary. It should also be understood that the terms used herein are for the purpose of describing only specific embodiments and are not intended to limit them.

[0181] Furthermore, where any feature or aspect of this disclosure is described in relation to the Markush Group, a person skilled in the art will recognize that this disclosure is also described in relation to any individual member or subgroup of the members of the Markush Group.

[0182] As will be understood by those skilled in the art, for any and all purposes, and particularly in terms of providing written explanations, all scopes disclosed herein also encompass any and all possible subscopes and combinations thereof. Any enumerated scope can be readily recognized as fully describing and enabling the same scope to be broken down into at least equal halves, thirds, quarters, fifths, tenths, and so on. As a non-limiting example, each scope considered herein can be readily broken down into a lower third, an intermediate third, and an upper third, and so on. Also, as will be understood by those skilled in the art, all terms such as “highest,” “at least,” “greater,” “smaller,” and similar terms include the enumerated numbers and refer to scopes that can be subsequently broken down into the subscopes considered above. Finally, as will be understood by those skilled in the art, a scope includes each individual member.

[0183] All publications, patent applications, issued patents, and other documents referenced herein are incorporated herein by reference in such a way that each individual publication, patent application, issued patent, or other document is specifically and individually indicated so as to be incorporated herein by reference in whole. Definitions contained in the texts incorporated by reference are excluded to the extent that they conflict with the definitions in this disclosure.

[0184] Other embodiments are described in the subsequent claims.

Claims

1. (i) Formula II: (In the formula, R ５ However, hydroxyl, or CH ３ And, R ６ However, it is H, Z is OR ７ And, R ７ However, H or C １ -C ６ It is alkyl, R ４ but, (a) A methyl group which may be substituted with one or more hydroxyl groups, or (b) C substituted with two or more hydroxyl groups １ -C ４ is an alkyl group, or (c) CH ２ CH (CH ３ ) OH, e is 1, and f and h are individually 0 or 1. g is 1, X － However, the compound is an anion selected from carbonate ions or hydroxide ions, and is present in an amount equal to the cation present in formula II. Furthermore, (ii) A stabilizer selected from antioxidants, oxygen absorbers, or reducing agents, and / or (iii) Rust inhibitors, and / or (iv) Alcohols, pyrocatechol, glycerin, and / or glycerin derivatives including, composition.

2. R ７ but, (a) Is it H? (b) C １ -C ６ It is alkyl, or (c) CH ３ That is, The composition according to claim 1.

3. R ４ The composition according to claim 1, wherein the group is a methyl group.

4. X － The composition according to claim 1, wherein the ion is a hydroxide ion.

5. The compound of formula II is, The composition according to claim 1, selected from the group consisting of and combinations thereof.

6. (a) The whole composition contains about 0.1% to about 80% by weight of the compound of formula II, or (b) The total composition having about 1% to about 50% by weight of the compound of formula II The composition according to claim 1.

7. The composition according to claim 1, wherein the compound of formula II is an etching agent.

8. (a) Hydroxylamine, and / or (b) Inorganic alkali compounds, and / or (c) Water, and / or (d) A hydrotropic component selected from the group consisting of cumenesulfonic acid, tetramethylammonium cumenesulfonate, tetramethylammonium xylenesulfonate, tetramethylammonium phenolsulfonate, tetramethylammonium toluenesulfonate, and tetramethylammonium benzenesulfonate, and / or (e) pH adjusters, buffers, or combinations thereof, and / or (f) at least one organic solvent or surfactant, and / or (g) Rheological modifiers, and / or (h) Chelating agents The composition according to claim 1, further comprising:

9. The composition according to claim 1, comprising a maximum of about 1000 ppb of a metal selected from the group consisting of Na, Mg, Al, K, Ca, Mn, Fe, Ni, Cu, Zn, Ag, Pd, and Cr.

10. The composition according to claim 1, which is essentially free of tetramethylammonium hydroxide (TMAH).

11. The composition according to claim 1, wherein the stabilizer selected from the antioxidant, oxygen scavenger, or reducing agent is selected from dithionite salts, amines, hydroxylamines, sulfites, hydroquinones, hydrides, formaldehyde, thiourea, butylated hydroxytoluene, butylated hydroxyanisole, ascorbic acid, or a combination of two or more thereof.

12. The composition according to claim 8, wherein the hydroxylamine is selected from hydroxylamine, hydroxylamine sulfate, hydroxylamine chloride, hydroxylamine oxalate, N,N-diethylhydroxylamine, isopropylhydroxylamine, dimethylhydroxylamine hydrochloride, and / or hydroxylamine phosphate.

13. The composition according to claim 8, wherein the organic solvent or surfactant is selected from DMSO, alcohol, ethoxylated alcohol, betaine, alkyl sulfonic acid, aryl sulfonic acid, or a combination of two or more thereof.

14. The composition according to claim 8, wherein the rheology modifier is a polymer rheology modifier.

15. The composition according to claim 14, wherein the polymer rheology modifier is polyacrylic acid.

16. The composition according to claim 8, wherein the chelating agent is ethylenediaminetetraacetic acid.

17. Use of the composition according to any one of claims 1 to 16 as an electronic equipment processing composition, a cleaning composition, a stripping composition, a degreasing composition, a phase transfer agent, or a combination of two or more thereof.

18. The use according to claim 17, wherein the use as an electronic equipment processing composition is selected from use as a wafer cleaning composition, an anisotropic etching composition, a photolithography composition, a photoresist developing composition, a post-chemical planarization cleaning composition, a printed circuit board cleaning composition, or a combination of two or more thereof.

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