Low toxicity organic tertiary and quaternary amines and uses thereof

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, TIFF2025060792000001.tif50128 formula, R 1 and R 5 are individually H, hydroxyl, or CH3, and R 2 and R 6 are individually H, hydroxyl, and 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 is independently H or C1-C6 alkyl; R 8 is, individually, a C1-C6 alkyl optionally substituted with one or more hydroxyl groups; R 10 are individually 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 independently 0 or 1; c and g are independently 0, 1, or 2; i and j are independently 2 or 3; and 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: TIFF2025060792000002.tif50128 in formula, R 1 , R 2 , R 5 , and R 6are individually H, hydroxyl, or CH3, and R 3 and R 7 is independently H or C1-C6 alkyl; R 4 is H or a C1-C6 alkyl group optionally substituted with one or more hydroxyl groups; a, b, d, e, f, and h are each independently 0 or 1; c and g are each independently 0, 1, or 2; X - is an anion.

[0003] In any embodiment, the compound of formula I can be a compound of formula IB and / or the compound of formula II can be a compound of formula IIB, TIFF2025060792000003.tif50128 formula, R 1 and R 5 are individually H, hydroxyl, or CH3, and R 2 and R 6 are individually H, CH 3、 N(CH3)2, or + N(CH3)3, and R in each occurrence 8 is, individually, a C1-C6 alkyl optionally substituted with one or more hydroxyl groups; R 10 are individually H or C1-C6 alkyl optionally substituted with one or more hydroxyl groups; R 4 is H or one or more hydroxyls, N(CH3)2, or + a, b, d, e, f, and h are each independently 0 or 1, c and g are each independently 0, 1, or 2, and X - is an anion.

[0004] The present technology also provides compositions comprising a compound of formula I (or species formula IA and / or IB), a compound of formula II (or species formula IIA and / or IIB), or a combination thereof. In any embodiment, the composition may be useful for electronics processing (e.g., semiconductor processing compositions), cleaning, stripping, degreasing, or a combination of two or more thereof. Compounds of formula I (or species formula IA and / or IB) and / or formula II (or species formula IIA and / or IIB) may also be useful as catalysts, phase transfer agents, or a combination 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 replacements for the highly toxic compound tetramethylammonium hydroxide ("TMAH"). In any embodiment, compounds of formula II (or species formula IIA and / or IIB) may be useful as replacements for the highly toxic compound tetramethylammonium hydroxide ("TMAH").

[0006] In any embodiment, the present technology provides a composition that includes a compound of formula I (or species formula IA and / or IB) or formula II (or species formula IIA and / or IIB) in place of TMAH. In any embodiment, the present technology provides a composition that includes a compound of formula II (or species formula IIA and / or IIB) in place of TMAH. [The present invention 1001] A composition comprising a compound of formula I, a compound of formula II, or a combination thereof, TIFF2025060792000004.tif50128 formula, R 1 and R 5 are individually H, hydroxyl, or CH; R 2 and R 6 are individually H, hydroxyl, CH3, N(CH3)2, or + 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 is independently H or C1-C6 alkyl; R at each occurrence 8 is, individually, C1-C6 alkyl optionally substituted with one or more hydroxyl groups; R at each occurrence 10 is individually 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 independently 0 or 1; c and g are independently 0, 1, or 2; i and j are 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; composition. [The present invention 1002] said compound of formula I is a compound of formula IA and / or said compound of formula II is a compound of formula IIA; TIFF2025060792000005.tif50128 formula, R 1 , R 2 , R 5 , and R 6 are individually H, hydroxyl, or CH; R 3 and R 7 is independently H or C1-C6 alkyl; R 4 is H or a C1-C6 alkyl group optionally substituted with one or more hydroxyl groups; a, b, d, e, f, and h are independently 0 or 1; c and g are independently 0, 1, or 2; X - is the anion, The composition of the present invention 1001. [The present invention 1003] said compound of formula I is a compound of formula IB and / or said compound of formula II is a compound of formula IIB; TIFF2025060792000006.tif50128 formula, R 1 and R 5 are individually H, hydroxyl, or CH; R 2 and R 6 are individually H, CH3, N(CH3)2, or + N(CH3)3, R at each occurrence 8 is, individually, C1-C6 alkyl optionally substituted with one or more hydroxyl groups; R at each occurrence 10 is individually H or C1-C6 alkyl optionally substituted with one or more hydroxyl groups; R 4 has one or more hydroxyl, N(CH3)2, or + C1-C6 alkyl optionally substituted with a N(CH3)3 group; a, b, d, e, f, and h are independently 0 or 1; c and g are independently 0, 1, or 2; X - is the anion, The composition of the present invention 1001. [The present invention 1004] Any of the compositions of 1001 to 1003 of the present invention, wherein a+b+c+d≧1 and e+f+g+h≧1. [The present invention 1005] Any of the compositions of 1001 to 1004 of the present invention, wherein a+b+c+d≧2 and e+f+g+h≧2. [The present invention 1006] R 1and R 5 Any of compositions 1001 to 1005 of the present invention, wherein is individually hydroxyl or CH3. [The present invention 1007] R 1 and R 5 Any of the compositions according to claims 1001 to 1005, wherein is H or CH3. [The present invention 1008] R 3 and R 7 The composition of any one of claims 1001 to 1007, wherein is H. [The present invention 1009] R 3 and R 7 Any of the compositions of 1001 to 1007, wherein each is individually C1-C6 alkyl. [The present invention 1010] R 3 and R 7 The composition of the present invention 1009, wherein is CH3. [The present invention 1011] R 4 Any of the compositions of 1001 to 1010, wherein is a C1-C4 alkyl optionally substituted with one or more hydroxyl groups. [The present invention 1012] R 4 The composition of claim 1011, wherein is a methyl group optionally substituted with one or more hydroxyl groups. [The present invention 1013] R 4 is terminally substituted with said one or more hydroxyl groups. [The present invention 1014] R 4 The composition of any of claims 1001 to 1013, wherein is substituted with two or more hydroxyl groups. [The present invention 1015] R 4 Any of the compositions of claims 1001 to 1013, wherein is CH2CH(CH3)OH. [The present invention 1016] R 4Any of the compositions of 1001 to 1010, wherein is a C1-C4 alkyl optionally substituted with one or more amine or ammonium groups. [The present invention 1017] R 4 is a methyl group optionally substituted with one or more amine or ammonium groups. [The present invention 1018] R 4 But one or more + The composition of invention 1016 or invention 1017, which is terminally substituted with an N(CH3)3 group. [The present invention 1019] R 4 But CH2C(CH3)2-N(CH3)3 + The composition of any one of 1001 to 1010 or 1016 of the present invention, [The present invention 1020] R 2 and R 6 Any of the compositions of 1001 to 1019 of the present invention, wherein is H. [The present invention 1021] R 2 and R 6 Any of the compositions of 1001 to 1019 of the present invention, wherein is hydroxyl. [The present invention 1022] R 2 and R 6 Any of the compositions of 1001 to 1019 of the present invention, wherein is CH3. [The present invention 1023] R 2 and R 6 But N(CH3)2 or + Any of the compositions of 1001 to 1019 of the present invention, wherein N(CH3)3. [The present invention 1024] R at each occurrence 8 and R 10 Any of the compositions of 1001 to 1023, wherein each is a C1-C6 alkyl optionally substituted with one or more hydroxyl groups. [The present invention 1025] R at each occurrence 8and R 10 Any of the compositions of 1001 to 1024 of the present invention, wherein is CH3. [The present invention 1026] R 8 and R 10 Any of the compositions of claims 1001 to 1024, wherein is selected from the group consisting of CH3 and C(CH3)2CH2OH. [The present invention 1027] X - is a halide, a sulfate ion, a methosulfate, a carbonate ion, a carboxylate ion, a phosphate ion, or a hydroxide ion. [The present invention 1028] X - The composition of any one of Nos. 1001 to 1027, wherein is a hydroxide ion. [The present invention 1029] The compound of formula I is Any of the compositions of 1001 to 1028, which is a compound of formula IA selected from the group consisting of TIFF2025060792000007.tif199162TIFF2025060792000008.tif177135 and combinations of two or more thereof. [The present invention 1030] The composition of the present invention 1029, wherein said compound of formula I is a compound of formula IA selected from the group consisting of DMAMPD, iso-DMAMPD, and combinations thereof. [The present invention 1031] The compound of formula II is Any of the compositions of 1001 to 1030, which is a compound of formula IIA selected from the group consisting of TIFF2025060792000009.tif178132TIFF2025060792000010.tif53137 and combinations of two or more thereof. [The present invention 1032] The composition of the present invention 1031, wherein said compound of formula II is a compound of formula IIA which is DMAMPD-AH. [The present invention 1033] The compound of formula I is Any of the compositions of 1001 to 1032, which is a compound of formula I selected from the group consisting of TIFF2025060792000011.tif154153 and combinations of two or more thereof. [The present invention 1034] The compound of formula II is Any of the compositions of 1001 to 1033 of the present invention, which is a compound of formula IIB selected from the group consisting of TIFF2025060792000012.tif178128 and combinations of two or more thereof. [The present invention 1035] Any of the compositions of claims 1001 to 1034, having from about 0.1% by weight to about 80% by weight of said compound of formula I, said compound of formula II, or a combination thereof, based on the total composition. [The present invention 1036] Any of the compositions of claims 1001 to 1035, having from about 1% by weight to about 50% by weight of said compound of formula I, said compound of formula II, or a combination thereof, based on the total composition. [The present invention 1037] The composition of any of claims 1001-1036, which is an electronics 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. [The present invention 1038] The composition of the present invention 1037, wherein the electronic device 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. [The present invention 1039] Any of the compositions of claims 1001-1038, further comprising a stabilizer (e.g., an antioxidant, oxygen scavenger, or reducing agent, such as dithionite salts, amines, hydroxylamines, sulfites, hydroquinones, hydrides, carboxylic acids, piperazines, formaldehyde, thioureas, borates, butylated hydroxytoluene, butylated hydroxyanisole, ascorbic acid, and the like, and combinations of two or more thereof). [The present invention 1040] The composition of any one of claims 1001 to 1039, further comprising a rust inhibitor. [The present invention 1041] The composition of any one of claims 1001 to 1040, further comprising alcohol, pyrocatechol, glycerin, and / or a glycerin derivative. [The present invention 1042] The composition of any one of claims 1001 to 1041, wherein said compound of formula I and / or said compound of formula II is an etching agent. [The present invention 1043] Any of the compositions of claims 1001 to 1042, further comprising a hydroxylamine (e.g., hydroxylamine, hydroxylamine sulfate, hydroxylamine chloride, hydroxylamine oxalate, N,N-diethylhydroxylamine, isopropylhydroxylamine, dimethylhydroxylamine hydrochloride, and / or hydroxylamine phosphate). [The present invention 1044] The composition of any one of claims 1001 to 1043, further comprising an inorganic alkaline compound. [The present invention 1045] The composition of any one of claims 1001 to 1044, further comprising water. [The present invention 1046] The composition of any one of claims 1001 to 1045, further comprising a hydrotropic component. [The present invention 1047] The composition of any one of claims 1001 to 1046, further comprising a pH adjuster, a buffering agent, or a combination thereof. [The present invention 1048] Any of the compositions of claims 1001 to 1047, further comprising at least one organic solvent or surfactant (e.g., DMSO, alcohol, ethoxylated alcohol, betaine, alkylsulfonic acid, arylsulfonic acid, or a combination of two or more thereof). [The present invention 1049] The composition of any of claims 1001 to 1048, further comprising a rheology modifier (for example, a polymeric rheology modifier such as polyacrylic acid). [The present invention 1050] The composition of any of claims 1001 to 1049, further comprising a chelating agent (e.g., ethylenediaminetetraacetic acid ("EDTA")). [The present invention 1051] Any of the compositions of claims 1001 to 1050, comprising up to 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. [The present invention 1052] Any of the compositions of inventions 1001 to 1051, which have reduced toxicity based on rat skin toxicity compared to a composition containing the same weight percent of tetramethylammonium hydroxide (TMAH). [The present invention 1053] Any of the compositions according to claims 1001 to 1052, which is essentially free of TMAH. [The present invention 1054] The compound of formula I or the compound of formula II of any one of 1001 to 1034 of the present invention. [The present invention 1055] A process for making said compound of formula II of the present invention 1054, comprising: Providing a solution containing a compound of formula I of any one of claims 1001 to 1034 and an organic solvent; Optionally, heating the solution to about 25° C. to about 45° C.; adding a methylating agent to the solution to form a mixture, the methylating agent being optionally added over a period of about 1 hour; mixing the mixture; and Optionally, cooling the mixture to less than about 20° C.; Optionally filtering the mixture. The process includes: DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0007] Detailed Description Various embodiments are described below. Please note that the specific embodiments are not intended as comprehensive descriptions or limitations to the broader aspects discussed herein. An aspect described in relation to a specific embodiment is not necessarily limited to that embodiment and can be implemented in any other embodiment.

[0008] As used herein, "about" is understood by those of ordinary skill in the art and will vary to some extent depending on the context in which it is used. If there are uses of the term that are not clear to persons of ordinary skill in the art, given the context in which it is used, "about" will mean plus or minus 10% of the particular term.

[0009] In the context of describing elements (particularly in the context of the claims that follow), the terms "a" and "an" and "the" and similar referents are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context. The recitation of ranges of values ​​herein is intended only to serve as a shorthand notation for individually referring to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated herein as if it were individually recited herein. All methods described herein can be performed in any suitable order, unless otherwise indicated herein or clearly contradicted by context. The use of any and all examples, or exemplary language (e.g., "etc.") provided herein is intended merely to better clarify the embodiments and does not pose limitations on the scope of the claims, unless otherwise indicated. No language in this specification should be construed as indicating any non-claimed element as essential.

[0010] Unless otherwise stated, numerical ranges are inclusive of the numbers defining the range (eg, 2 and 10), such as, for example, "from 2 to 10."

[0011] Unless otherwise indicated, ratios, percentages, parts, etc. are by weight.

[0012] As used herein, "substituted" generally refers to an alkyl, alkenyl, alkynyl, aryl, or ether group (e.g., an alkyl group) as defined below, in which one or more bonds to a hydrogen atom contained therein are replaced by a bond to a non-hydrogen or non-carbon atom. Substituted groups also include groups in which one or more bonds to a carbon or hydrogen atom are replaced by one or more bonds, including double or triple bonds, to a heteroatom. Thus, unless otherwise specified, a substituent is substituted with one or more substituents. In some embodiments, a substituent is substituted with 1, 2, 3, 4, 5, or 6 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, esters, urethanes, oximes, hydroxylamines, alkoxyamines, aralkoxyamines, thiols, sulfides, sulfoxides, sulfones, sulfonyls, sulfonamides, amines, N-oxides, hydrazines, hydrazides, hydrazones, azides, amides, ureas, amidines, guanidines, enamines, imides, isocyanates, isothiocyanates, cyanates, thiocyanates, imines, nitro groups, nitriles (i.e., CN), and the like.

[0013] An "alkyl" group, as used herein, includes straight-chain and branched alkyl groups having 1 to about 20 carbon atoms, typically 1 to 12 carbons, or in some embodiments, 1 to 8, 1 to 6, or 1 to 4 carbon atoms. As used herein, an "alkyl group" includes cycloalkyl groups, as defined below. An alkyl group can be substituted or unsubstituted. Examples of straight-chain alkyl groups include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl groups. Examples of branched alkyl groups include, but are not limited to, isopropyl, sec-butyl, t-butyl, neopentyl, and isopentyl groups. Representative substituted alkyl groups can be substituted one or more times with, for example, amino, thio, hydroxy, cyano, alkoxy, and / or halo groups, such as F, Cl, Br, and I groups. As used herein, the term haloalkyl is an alkyl group having one or more halo groups. In some embodiments, haloalkyl refers to a perhaloalkyl group. In some embodiments, an alkyl group can 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] The term "carboxyl" or "carboxylate" as used herein refers to the group -C(O)OH or its ionized form, -C(O)O-.

[0015] The term "carbonyl" as used herein refers to a -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") refers to -NR 65 R 66 R refers to the group 65 and R 66are 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 can be a quaternary amine, which as used herein refers to an ammonium group. In some embodiments, the ammonium comprises 1, 2, or 3 alkyl groups. The alkyl groups can independently comprise straight chain and branched alkyl groups having 1 to about 20 carbon atoms, typically 1 to 12 carbons, 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 groups can be methyl groups.

[0018] Groups described herein that have two or more points of attachment (i.e., divalent, trivalent, or polyvalent) within the compounds of the present 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, etc. Substituents that have a single point of attachment to the compounds of the present technology are not referred to using the "ene" designation.

[0019] In one aspect, the present technology provides a compound of formula I and / or a compound of formula II, TIFF2025060792000013.tif50128 formula, R 1 and R 5 are individually H, hydroxyl, or CH3, and R 2 and R 6 are individually H, hydroxyl, and 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(R10 ) j and R 3 and R 7 is independently H or C1-C6 alkyl; R 8 is, individually, a C1-C6 alkyl optionally substituted with one or more hydroxyl groups; R 10 are individually 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 independently 0 or 1; c and g are independently 0, 1, or 2; i and j are independently 2 or 3; and X - is an anion and is present in an amount equal to the cation present in Formula I or Formula II.

[0020] In one 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, TIFF2025060792000014.tif50128 formula, R 1 , R 2 , R 5 , and R 6 are individually H, hydroxyl, or CH3, and R 3 and R 7 is independently H or C1-C6 alkyl; R 4 is H or a C1-C6 alkyl group optionally substituted with one or more hydroxyl groups; a, b, d, e, f, and h are each independently 0 or 1; c and g are each independently 0, 1, or 2; X - is an anion.

[0021] In another embodiment, the compound of formula I can be a compound of formula IB and / or the compound of formula II can be a compound of formula IIB, TIFF2025060792000015.tif50128 formula, R 1 and R 5are individually H, hydroxyl, or CH3, and R 2 and R 6 are individually H, CH 3、 N(CH3)2, or + N(CH3)3, and R in each occurrence 8 is, individually, a C1-C6 alkyl optionally substituted with one or more hydroxyl groups; R 10 are individually H or C1-C6 alkyl optionally substituted with one or more hydroxyl groups; R 4 is H or one or more hydroxyls, N(CH3)2, or + a, b, d, e, f, and h are each independently 0 or 1, c and g are each independently 0, 1, or 2, and X - is an anion.

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

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

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

[0025] In some embodiments, d and h can be 0. In some embodiments, d and h can 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 can 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 can be 0, c and g can be 2, and d and h can be 1.

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

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

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

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

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

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

[0035] In some embodiments, R 1 and R 5 may individually be hydroxyl or CH. In some embodiments, R 1 and R 5can be H or CH. In some embodiments, R 1 and R 5 can be H. In some embodiments, R 1 and R 5 can be CH3.

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

[0037] In some embodiments, R 4 can be H or a C1-C6 alkyl group optionally substituted with one or more hydroxyl groups. In some embodiments, R 4 may be a C1-C6 alkyl group optionally substituted with one or more hydroxyl groups. In some embodiments, R 4 can be a C1-C4 alkyl optionally substituted with one or more hydroxyl groups. In some embodiments, R 4 can be a C1-C3 alkyl optionally substituted with one or more hydroxyl groups. In some embodiments, R 4 can be a C1-C2 alkyl optionally substituted with one or more hydroxyl groups. In some embodiments, R 4 may be a methyl group optionally substituted with one or more hydroxyl groups. In some embodiments, R 4may be substituted with one or more hydroxyl groups. In some embodiments, R 4 may be terminally substituted with one or more hydroxyl groups. In some embodiments, R 4 may be substituted with two or more hydroxyl groups. In some embodiments, R 4 may be terminally substituted with one of two or more hydroxyl groups. In some embodiments, R 4 can be a CHCH(CH)OH group. In some embodiments, R 4 may be substituted with one or more halide groups. In some embodiments, R 4 may be substituted with two or more halide groups. In some embodiments, R 4 may be substituted with one or more hydroxyl groups and one or more halide groups. In some embodiments, R 4 may be substituted with one or more hydroxyl groups rather than any halide groups. In some embodiments, R 4 may be substituted with one or more halide groups rather than any hydroxyl groups. In some embodiments, R 4 can be H or a C1-C6 alkyl group optionally substituted with one or more amine or ammonium groups. In some embodiments, R 4 can be a C1-C6 alkyl group optionally substituted with one or more amine or ammonium groups. In some embodiments, R 4 can be a C1-C4 alkyl optionally substituted with one or more amine or ammonium groups. In some embodiments, R 4 can be a C1-C3 alkyl optionally substituted with one or more amine or ammonium groups. In some embodiments, R 4 can be a C1-C2 alkyl optionally substituted with one or more amine or ammonium groups. In some embodiments, R 4 may be a methyl group optionally substituted with one or more amine or ammonium groups. In some embodiments, R 4 is one or more +In some embodiments, R may be an alkyl group substituted with an N(C-C alkyl) group. 4 is one or more + In some embodiments, R may be an alkyl group substituted with a N(CH) group. 4 is one or more + In some embodiments, R may be an alkyl group substituted with an NH(CH) group. 4 is one or more + In some embodiments, R 4 is one or more + In some embodiments, R 4 is one or more + In some embodiments, R 4 is one + In some embodiments, R 4 is CH2C(CH3)2-N(CH3)3 + It may be a group.

[0038] In some embodiments, R 2 and R 6 is H, hydroxyl, CH3, N(CH3)2, or + N(CH3)3. In some embodiments, R 2 and R 6 is H. In some embodiments, R 2 and R 6 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 + 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] In some embodiments, R in each occurrence 8 and R 10 is, individually, a C1-C6 alkyl optionally substituted with one or more hydroxyl groups. In some embodiments, R 8 and R 10 is, individually, C1-C4 alkyl optionally substituted with one or more hydroxyl groups. In some embodiments, R 8 and R 10 is individually a C1-C4 alkyl substituted with one hydroxyl group or CH3. In some embodiments, R 8 and R 10 In some embodiments, R in each occurrence is the same. 8 and R 10 In some embodiments, R in two occurrences is CH3. 8 and R 10 are the same. In some embodiments, two R 8 and two R 10 is CH3, R 8 and R 10 The third occurrence of is a C1-C4 alkyl substituted with one hydroxyl group. 8 and two R 10 is CH3, R 8 and R 10 The remaining occurrences of are C1-C4 alkyl substituted with one hydroxyl group. In some embodiments, R 8 and R 10 is selected from the group consisting of CH3 and C(CH3)2CH2OH. In some embodiments, two R 8 and two R 10 is CH3, and the third R 8 and R 10 is a C(CH)CHOH group. In some embodiments, one R 8 and two R 10 is CH3, and the remaining R 8 and R 10is a C(CH)CHOH group. In some embodiments, R 8 are CH3 and C(CH3)2CH2OH, and R 10 is CH3, CH3, and C(CH3)2CH2OH. In some embodiments, R 8 and R 10 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 cations present in Formula I and / or Formula II. In some embodiments, Formula I may not have any cations, and X - is not present as a counter anion. In some embodiments, formula II can have 1, 2, or 3 cations, and X - is present as an anion equal to the amount of cationic charge. - can be a halide, sulfate, methosulfate, carbonate, carboxylate, phosphate, or hydroxide. - may be a halide or hydroxide ion. In some embodiments, X - may 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 TIFF2025060792000016.tif243160TIFF2025060792000017.tif129135 or any combination of two or more thereof.

[0045] In some embodiments, the composition of the compound of formula IA comprises 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 comprises 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 compositions comprise a compound of formula IIA.

[0047] In some embodiments, the compound of formula IIA is TIFF2025060792000018.tif78132TIFF2025060792000019.tif157138 or any combination of two or more thereof.

[0048] In some embodiments, the compound of formula IIA comprises DMTA-AH, DMAPPD-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 comprises DMAMP-AH, iso-DMAEPD-AH, or a combination thereof. In some embodiments, the compound of formula IIA comprises DMAPPD-AH, iso-DMAMPD-AH, or a combination thereof. In some embodiments, the compound of formula IIA comprises DMAPPD-AH.

[0049] In some preferred embodiments, the compositions comprise a compound of formula IB.

[0050] In some embodiments, the compound of formula IB is TIFF2025060792000020.tif136147 or any combination of two or more of them.

[0051] In some preferred embodiments, the compositions comprise a compound of formula IIB.

[0052] In some embodiments, the compound of formula IIB is TIFF2025060792000021.tif180128 or a combination of two or more of them.

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

[0054] In some embodiments, the composition can be an electronics 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 electronics processing composition can be 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.

[0055] In some embodiments, the composition further comprises a stabilizer (e.g., an antioxidant, oxygen scavenger, or reducing agent, such as, for example, dithionite salts, amines, hydroxylamines, sulfites, hydroquinones, hydrides, carboxylic acids, piperazines, formaldehyde, thioureas, borates, butylated hydroxytoluene, butylated hydroxyanisole, ascorbic acid, and the like, and combinations of two or more thereof).

[0056] In some embodiments, the composition further comprises a rust inhibitor. In any embodiment, the rust inhibitor may comprise a sugar, an alcohol sugar, pyrocatechol, and / or butylcatechol. Non-limiting examples of sugars or alcohol 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 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 a hydroxylamine (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 alkaline compound (eg, sodium hydroxide, potassium hydroxide, ammonia, and hydrazine hydrate).

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

[0062] In some embodiments, the composition further comprises a hydrotropic component (e.g., cumene sulfonic acid, tetramethylammonium cumene sulfonate, tetramethylammonium xylene sulfonate, tetramethylammonium phenolsulfonate, tetramethylammonium toluenesulfonate, and / or tetramethylammonium benzenesulfonate).

[0063] In some embodiments, the composition further comprises a pH adjuster, a buffering agent, or a combination thereof (e.g., an amine, an amino alcohol, a hydroxylamine, an amine oxide, an organic hydroxide, a phosphate, a carbonate, and combinations of two or more thereof).

[0064] In some embodiments, the composition further comprises at least one organic solvent or surfactant (e.g., DMSO, alcohol, ethoxylated alcohol, betaine, alkylsulfonic acid, arylsulfonic acid, or a combination of two or more thereof).

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

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

[0067] In some embodiments, the composition comprises up to 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.

[0068] In some embodiments, the compositions have reduced toxicity based on rat skin toxicity compared to a composition comprising the same weight percent tetramethylammonium hydroxide (TMAH).

[0069] In some embodiments, the composition may be essentially free of TMAH. As used herein, "essentially free" refers to 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 no detectable amount of TMAH.

[0070] In another aspect, the present technology provides a process for making 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, the methylating agent being optionally added over a period of about 1 hour, mixing (e.g., stirring) the mixture, optionally cooling the mixture to less than about 20°C (e.g., 10°C), and optionally filtering the mixture (e.g., ion exchange resin filter).

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

[0072] In some embodiments, the compound of formula I is a compound of formula IA or formula IB: TIFF2025060792000022.tif224153TIFF2025060792000023.tif208156 or a combination of two or more thereof. In some embodiments, the compound of formula I comprises DMTA, DMAMPD, DMAEPD, DMMOPA, iso-DMTA, iso-DMAMPD, iso-DMAEPD, iso-DMAMP, PMPDA, TMPDA, HMPTA, HPMAMP, or a combination of two or more thereof. In some embodiments, the compound of formula I comprises DMTA, DMAEPD, DMMOPA, iso-DMTA, iso-DMAMPD, DMAMPD, iso-DMAEPD, iso-DMAMP, PMPDA, TMPDA, HMPTA, HPMAMP, or a combination of two or more thereof. In some embodiments, the compound of formula I comprises DMAMPD, iso-DMAMPD, or a combination thereof. In some embodiments, the compound of formula I comprises DMAMPD.

[0073] In some embodiments, the compound of formula I (including formulas IA and IB) is Does not include TIFF2025060792000024.tif189164.

[0074] In some embodiments, the compound of formula II is a compound of formula IIA or formula IIB: TIFF2025060792000025.tif94140TIFF2025060792000026.tif234124 or a combination of two or more thereof. In some embodiments, the compound of formula II comprises 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 a combination of two or more thereof. In some embodiments, the compound of formula II comprises DMAMP-AH, iso-DMAEPD-AH, or a combination thereof. In some embodiments, the compound of formula II comprises DMAMPD-AH, iso-DMAMPD-AH, or a combination thereof. In some embodiments, the compound of formula II comprises DMAMPD-AH, iso-DMAMPD-AH, or a combination thereof. In some embodiments, the compound of formula II comprises DMAMPD-AH.

[0075] In some embodiments, the compound of formula II (including formulas IIA and IIB) is Does not include TIFF2025060792000027.tif152156, In the formula, X - is as defined herein.

[0076] The invention having thus been generally described will be more readily understood by reference to the following examples, which are provided by way of illustration and are not intended to be limiting of the invention. EXAMPLES

[0077] Example 1. Synthesis of DMAMP-iodide. To a solution of 147 g (1.00 mol) DMAMP-80 (ANGUS Chemical Company) and 580 g isopropyl alcohol (99%, VWR International), 145 g (1.02 mol) methyl iodide (99%, Aldrich Chemical Company) was added in portions over 60 minutes while maintaining the internal temperature between 25° C. and 45° C. After addition was complete, the mixture was stirred at ambient temperature for 3 hours and then cooled to 10° C. for 1 hour. The mixture was pressure filtered under nitrogen. The filter cake was washed with 500 g isopropyl alcohol and then dried under vacuum to 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 3x60 cm glass column with a bed volume of 350 mL 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 20 mL / min. The resin was activated by pumping 2 bed volumes of 8 wt% aqueous sodium hydroxide at a rate of 2 mL / min. The resin was rinsed with 6 bed volumes of deionized water to produce a neutral eluate. 100 g of DMAMP-iodide was dissolved in 260 g of deionized water and loaded onto the column at 2 mL / min. The eluate was collected when the pH was above 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 give 125 mL of a yellow liquid. The product contained no detectable iodide by peroxide / cellulose test. The product contained 44% solids by weight 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) was added 145 g (1.02 mol) of methyl iodide (99%, Aldrich Chemical Company) in portions over 90 minutes while maintaining the internal temperature between 25° C. and 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 filter cake was washed twice with 200 g of isopropyl alcohol and then dried to constant weight under vacuum to provide 3-methoxy-N,N,N-trimethylpropane-1-ammonium iodide. The 3-methoxy-N,N,N-trimethylpropane-1-ammonium iodide was a colorless solid weighing 250.0 g (96.9% yield). 1 H NMR (D2O) was consistent with the assigned structure.

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

[0081] Example 4. Synthesis of 1,3-dihydroxy-N,N,N,2-tetramethylpropane-2-ammonium hydroxide. 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) was added 490 g (3.45 mol) of methyl iodide (99%, Aldrich Chemical Company) in portions over 70 minutes while maintaining the internal temperature between 25° C. and 45° C. 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 followed by decantation. The solid was dried under vacuum to constant weight to provide 1,3-dihydroxy-N,N,N,2-tetramethylpropane-2-ammonium iodide. The 1,3-dihydroxy-N,N,N,2-tetramethylpropane-2-ammonium iodide was a colorless solid weighing 562 g (75.9% yield). 1 H NMR (D2O) was consistent with the assigned structure.

[0082] 1,3-Dihydroxy-N,N,N,2-tetramethylpropane-2-ammonium iodide was dissolved in a minimum amount of water and converted to 1,3-dihydroxy-N,N,N,2-tetramethylpropane-2-ammonium hydroxide following 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, ANGUS Chemical Company) was added 70 g (1.4 mol) of methyl chloride (99.5+%, Aldrich Chemical Company) in a 1 L Parr reactor. The mixture was heated to 60° C. and the pressure was 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 with 20 psi of nitrogen three times. 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 H NMR (D2O) was consistent with the assigned structure.

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

[0085] Example 6. Synthesis of 2-hydroxy-2-(hydroxymethyl)-N,N,N-trimethylbutan-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 added in portions over 30 minutes while maintaining the internal temperature between 25° C. and 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 solidified under vacuum for 4 hours. The resulting solid was triturated with 100 g of isopropyl alcohol and then filtered under nitrogen. The solid was dried under vacuum to constant weight to provide 2-hydroxy-2-(hydroxymethyl)-N,N,N-trimethylbutane-1-ammonium iodide, a colorless solid weighing 164 g (82% yield). 1 H NMR (D2O) was consistent with the assigned structure.

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

[0087] Exemplary embodiments Item 1. A compound of formula I or formula II, TIFF2025060792000028.tif50128 formula, R 1 and R 5 are individually H, hydroxyl, or CH3, and R 2 and R 6 are 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 is independently H or C-C alkyl; and R 8 is, individually, C1-C6 alkyl optionally substituted with one or more hydroxyl groups; and R 10 is, individually, a 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 independently 0 or 1; c and g are independently 0, 1, or 2; i and j are independently 2 or 3; and X - is an anion and is present in an amount equal to the cation present in formula I or formula II.

[0088] Item 2. The compound of formula I is a compound of formula IA, and / or the compound of formula II is a compound of formula IIA; TIFF2025060792000029.tif50128 formula, R 1 , R 2 , R 5 , and R 6 are individually H, hydroxyl, or CH3, and R 3 and R 7 is independently H or C1-C6 alkyl; R 4 is H or a C1-C6 alkyl group optionally substituted with one or more hydroxyl groups; a, b, d, e, f, and h are each independently 0 or 1; c and g are each independently 0, 1, or 2; and X - The compound of item 1, wherein is an anion.

[0089] Item 3. The compound of formula I is a compound of formula IB, and / or the compound of formula II is a compound of formula IIB; TIFF2025060792000030.tif50128 in formula, R 1 and R 5 are 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 is, individually, C1-C6 alkyl optionally substituted with one or more hydroxyl groups; and R 10 is, individually, a C1-C6 alkyl optionally substituted with one or more hydroxyl groups; R 4 is H, or one or more hydroxyl, N(CH3)2, or + a, b, d, e, f, and h are each independently 0 or 1, c and g are each independently 0, 1, or 2, and X - The compound of item 1, wherein is an anion.

[0090] Item 4. The compound according to any one of items 1 to 3, wherein c and g are 1.

[0091] Item 5. The compound according to any one of items 1 to 3, wherein c and g are 0.

[0092] Item 6. The compound according to any one of items 1 to 5, wherein a and e are 0.

[0093] Item 7. The compound according to any one of items 1 to 5, wherein a and e are 1.

[0094] Item 8. The compound according to any one of items 1 to 7, wherein b and f are 0.

[0095] Item 9. The compound of any one of items 1 to 7, wherein b and f are 1.

[0096] Item 10. The compound according to any one of items 1 to 9, wherein d and h are 0.

[0097] Item 11. The compound according to any one of items 1 to 9, wherein d and h are 1.

[0098] Item 12. The compound of any one of items 1 to 3, wherein a, b, c, e, f, and g are 1.

[0099] Item 13. The compound according to any one of items 1 to 3, wherein a, b, c, e, f, and g are 0.

[0100] Item 14. The compound according to any one of items 1 to 13, wherein a+b+c+d≧1.

[0101] Item 15. The compound according to any one of items 1 to 14, wherein a+b+c+d≧2.

[0102] Item 16. The compound according to any one of items 1 to 15, wherein e+f+g+h≧1.

[0103] Item 17. The compound according to any one of items 1 to 16, wherein e+f+g+h≧2.

[0104] Item 18. The compound of any one of items 1 to 3, wherein a, b, e, and f are 0, and c, d, g, and h are 1.

[0105] Item 19. The compound according to any one of items 1 to 3, wherein a, b, d, e, f, and h are 1, c and g are 0, or a, b, d, e, f, and h are 0, c and g are 1.

[0106] Item 20. The compound of any one of items 1 to 3, wherein a, b, c, e, f, and g are 0, and d and h are 1.

[0107] Item 21. The compound of any one of items 1 to 3, wherein a, d, e, and h are 0, and b, c, f, and g are 1.

[0108] Item 22. The compound according to any one of items 1 to 3, wherein a, b, d, e, f, and h are 0, and c and g are 1.

[0109] Item 23. The compound according to any one of items 1 to 3, wherein 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 The compound of any one of paragraphs 1 to 23, wherein each is individually hydroxyl or CH3.

[0111] Section 25.R 1 and R 5 The compound according to any one of items 1 to 23, wherein is H or CH3.

[0112] Section 26.R 1 and R 5 The compound according to any one of items 1 to 25, wherein is CH3.

[0113] Section 27.R 3 and R 7 The compound according to any one of paragraphs 1 to 26, wherein

[0114] Section 28.R 3 and R 7 is, individually, C1-C6 alkyl.

[0115] Section 29.R 3 and R 7 is, individually, C1-C4 alkyl.

[0116] Section 30.R 3 and R 7 is independently C1-C3 alkyl.

[0117] Section 31.R 3 and R 7 is individually C1-C2 alkyl.

[0118] Section 32.R 3 and R 7 The compound according to any one of items 28 to 31, wherein is CH3.

[0119] Section 33.R 4 is a C1-C4 alkyl group optionally substituted with one or more hydroxyl groups.

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

[0121] Section 35.R 4 is a C1-C2 alkyl group optionally substituted with one or more hydroxyl groups.

[0122] Section 36.R 4 is a methyl group optionally substituted with one or more hydroxyl groups.

[0123] Section 37.R 4 is substituted with one or more hydroxyl groups.

[0124] Section 38.R 4 is terminally substituted with one or more hydroxyl groups.

[0125] Section 39.R 4 is substituted with two or more hydroxyl groups.

[0126] Section 40.R 4 is terminally substituted with one of two or more hydroxyl groups.

[0127] Section 41.R 4The compound according to any one of items 1 to 34, wherein is CH2CH(CH3)OH.

[0128] Section 42.R 4 is a C1-C4 alkyl group optionally substituted with one or more amine or ammonium groups.

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

[0130] Section 44.R 4 is a C1-C2 alkyl group optionally substituted with one or more amine or ammonium groups.

[0131] Section 45.R 4 is a methyl group optionally substituted with one or more amine or ammonium groups.

[0132] Section 46.R 4 is substituted with one or more amine or ammonium groups.

[0133] Section 47.R 4 But one or more + The compound of item 46 which is terminally substituted with a N(CH3)3 group.

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

[0135] Section 49.R 2 and R 6 The compound according to any one of paragraphs 1 to 48, wherein

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

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

[0138] Section 52.R 2 and R 6 But N(CH3)2 or + The compound according to any one of items 1 to 48, wherein 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 is, individually, a C1-C4 alkyl optionally substituted with one or more hydroxyl groups.

[0143] Item 57. R in each occurrence 8 and R 10 is, individually, a 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

[0145] Item 59.2 occurrences of R 8 and R 10 The compound according to any one of items 1 to 58, wherein

[0146] Item 60. R in each occurrence 8 and R 10 The compound according to any one of items 1 to 59, wherein is CH3.

[0147] 61.2 occurrences of R 8 and R 10 is CH3, and R at the third occurrence 8 and R 10 The compound of item 59, wherein R is a C(CH3)2CH2OH group. 8 and R 10 59. The compound of claim 59, wherein R is selected from the group consisting of CH3 and C(CH3)2CH2OH. 8 are CH3 and C(CH3)2CH2OH, and R 10 The compound of claim 59, wherein is CH3, CH3, and C(CH3)2CH2OH.

[0148] Section 62.X - is a halide, sulfate ion, methosulfate, carbonate ion, carboxylate ion, phosphate ion, or hydroxide ion.

[0149] Section 63.X - The compound according to any one of items 1 to 62, wherein is a halide or hydroxide ion.

[0150] Section 64.X - The compound according to any one of items 1 to 63, wherein is a hydroxide ion.

[0151] Item 65. The compound of formula I, TIFF2025060792000031.tif135169TIFF2025060792000032.tif252150 and combinations of two or more thereof.

[0152] Item 66. The 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 combinations of two or more thereof. The compound of item 66, wherein the compound of formula I is a compound of formula IA, which is DMAMPD.

[0153] Item 67. The compound of formula II, TIFF2025060792000033.tif179132TIFF2025060792000034.tif53138 and combinations of two or more thereof.

[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 a combination of two or more thereof. The composition of item 68, wherein the compound of formula IIA is DMAMPD-AH.

[0155] Item 69. The compound of formula I, TIFF2025060792000035.tif150157 and combinations of two or more thereof.

[0156] Item 70. The compound of formula II, TIFF2025060792000036.tif125128 and combinations of two or more thereof.

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

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

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

[0160] Item 74. The composition of any one of items 71 to 73, 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.

[0161] Item 75. The composition of item 74, wherein the electronic device 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. The composition of any one of items 71 to 75, further comprising a stabilizer (e.g., an antioxidant, an oxygen scavenger, or a reducing agent, such as a dithionite salt, an amine, a hydroxylamine, a sulfite, a hydroquinone, a hydride, a carboxylic acid, a piperazine, a formaldehyde, a thiourea, a borate, a butylated hydroxytoluene, a butylated hydroxyanisole, an ascorbic acid, or the like, and combinations of two or more thereof).

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

[0164] Item 78. The composition of any one of items 71 to 77, further comprising alcohol, pyrocatechol, glycerin, and / or a glycerin derivative.

[0165] Item 79. The composition of 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. The composition of any one of items 71 to 79, further comprising a hydroxylamine (e.g., hydroxylamine, hydroxylamine sulfate, hydroxylamine chloride, hydroxylamine oxalate, N,N-diethylhydroxylamine, isopropylhydroxylamine, dimethylhydroxylamine hydrochloride, and / or hydroxylamine phosphate).

[0167] Item 81. The composition of any one of items 71 to 80, further comprising an inorganic alkaline compound (e.g., sodium hydroxide, potassium hydroxide, ammonia, and hydrazine hydrate).

[0168] Item 82. The composition of any one of items 71 to 81, further comprising water.

[0169] Item 83. The composition of any one of items 71 to 82, further comprising a hydrotropic component (e.g., cumene sulfonic acid, tetramethylammonium cumene sulfonate, tetramethylammonium xylene sulfonate, tetramethylammonium phenolsulfonate, tetramethylammonium toluenesulfonate, and / or tetramethylammonium benzenesulfonate).

[0170] Item 84. The composition of any one of items 71 to 83, further comprising a pH adjuster, a buffer, or a combination thereof (e.g., an amine, an amino alcohol, a hydroxylamine, an amine oxide, an organic hydroxide, a phosphate, a carbonate, and combinations of two or more thereof).

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

[0172] Item 86. The composition of any one of items 71 to 85, further comprising a rheology modifier (e.g., a polymeric rheology modifier such as polyacrylic acid).

[0173] Item 87. The composition of any one of items 71 to 86, further comprising a chelating agent (e.g., ethylenediaminetetraacetic acid ("EDTA")).

[0174] Item 88. The composition of any one of items 71 to 87, comprising up to 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.

[0175] Item 89. The composition of any one of items 71 to 88, having reduced toxicity compared to a composition containing the same weight percent of tetramethylammonium hydroxide (TMAH) based on rat skin toxicity.

[0176] Item 90. The composition of any one of items 71 to 89, which is essentially free of TMAH.

[0177] Item 91. A process for making a compound of formula II according to any one of items 1 to 70, comprising: providing a solution comprising a compound of formula I according to any one 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, the methylating agent being 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., ion exchange resin filter).

[0178] While particular embodiments have been illustrated and described, it is to be understood that changes and modifications can be made thereto, in accordance with ordinary skill in the art, without departing from the technology in its broader aspects as defined in the appended claims.

[0179] The embodiments illustratively described herein may suitably be practiced in the absence of any element(s), limitation(s) not specifically disclosed herein. Thus, for example, terms such as "comprising," "including," "containing," and the like, are to be read broadly and without limitation. Furthermore, the terms and expressions employed herein are used as terms of description and not as terms of limitation, and in the use of such terms and expressions, there is no intention to exclude any equivalents of the features shown and described or portions thereof, recognizing that various modifications are possible within the scope of the claimed technology. Furthermore, the phrase "consisting essentially of" is to be understood to include the elements specifically recited, as well as additional elements that do not materially affect the basic and novel characteristics of the claimed technology. The phrase "consisting of" excludes any elements not specified.

[0180] The present disclosure is not limited with respect to the specific embodiments described in this application. Many modifications and variations can be made without departing from the spirit and scope thereof, as will be apparent to those skilled in the art. Functionally equivalent methods and compositions within the scope of the present disclosure will be apparent to those skilled in the art from the above description, in addition to those recited herein. Such modifications and variations are intended to be included within the scope of the appended claims. The present disclosure should be limited only by the appended claims, and the full scope of equivalents to which such claims are entitled. It is to be understood that the present disclosure is not limited to specific methods, reagents, compound compositions, or biological systems, which may of course vary. It is also to be understood that the terminology used herein is for the purpose of describing specific embodiments only, and is not intended to be limiting.

[0181] Furthermore, when features or aspects of the disclosure are described in terms of a Markush group, those skilled in the art will recognize that the disclosure is also described in terms of any individual members or subgroups of members of the Markush group.

[0182] As will be understood by those skilled in the art, for any and all purposes, particularly in terms of providing a written description, all ranges disclosed herein include any and all possible subranges and combinations of subranges. Any recited range can be easily recognized as fully describing and allowing the same range to be broken down into at least equal halves, 1 / 3, 1 / 4, 1 / 5, 1 / 10, etc. As a non-limiting example, each range discussed herein can be easily broken down into a lower 1 / 3, a middle 1 / 3, an upper 1 / 3, etc. Also, as will be understood by those skilled in the art, words such as "up to," "at least," "greater than," "less than," and the like all refer to ranges that are inclusive of the recited numbers and can be subsequently broken down into the subranges discussed above. Finally, as will be understood by those skilled in the art, a range includes each individual member.

[0183] All publications, patent applications, issued patents, and other documents referred to herein are incorporated by reference herein to the same extent as if each individual publication, patent application, issued patent, or other document was specifically and individually indicated to be incorporated by reference in its entirety. Definitions contained in the text incorporated by reference are excluded to the extent they conflict with definitions in this disclosure.

[0184] Other embodiments are set forth in the following claims.

Claims

1. A composition comprising a compound of formula I, a compound of formula II, or a combination thereof, During the ceremony, R １ and R ５ are individually H, hydroxyl, or CH ３ and R ２ and R ６ are individually H, hydroxyl, CH ３ , N(CH ３ ) ２ ,or ＋ N (CH ３ ) 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 is individually H or C １ -C ６ is alkyl, R at each occurrence ８ C may be individually substituted with one or more hydroxyl groups １ -C ６ is alkyl, R at each occurrence １０ are each independently H or C optionally substituted with one or more hydroxyl groups; １ -C ６ is alkyl, R ４ is H or C optionally substituted with one or more hydroxyl, amine, or ammonium groups; １ -C ６ is an alkyl group, a, b, d, e, f, and h are independently 0 or 1; c and g are independently 0, 1, or 2; i and j are 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; composition.

2. said compound of formula I is a compound of formula IA and / or said compound of formula II is a compound of formula IIA; During the ceremony, R １ , R ２ , R ５ , and R ６ are individually H, hydroxyl, or CH ３ and R ３ and R ７ is individually H or C １ -C ６ is alkyl, R ４ is H or C optionally substituted with one or more hydroxyl groups; １ -C ６ is an alkyl group, a, b, d, e, f, and h are independently 0 or 1; c and g are independently 0, 1, or 2; X － is the anion, The composition of claim 1.

3. said compound of formula I is a compound of formula IB and / or said compound of formula II is a compound of formula IIB; During the ceremony, R １ and R ５ are individually H, hydroxyl, or CH ３ and R ２ and R ６ However, individually, H, CH ３ , N(CH ３ ) ２ ,or ＋ N (CH ３ ) ３ and R at each occurrence ８ C may be individually substituted with one or more hydroxyl groups １ -C ６ is alkyl, R at each occurrence １０ are each independently H or C optionally substituted with one or more hydroxyl groups; １ -C ６ is alkyl, R ４ has one or more hydroxyl, N(CH ３ ) ２ ,or ＋ N (CH ３ ) ３ C optionally substituted with a group １ -C ６ is alkyl, a, b, d, e, f, and h are independently 0 or 1; c and g are independently 0, 1, or 2; X － is the anion, The composition of claim 1.

4. The composition according to any one of claims 1 to 3, wherein a+b+c+d≧1 and e+f+g+h≧1.

5. The composition according to any one of claims 1 to 4, wherein a+b+c+d≧2 and e+f+g+h≧2.

6. R １ and R ５ are individually hydroxyl or CH ３ The composition according to any one of claims 1 to 5,

7. R １ and R ５ is H or CH ３ The composition according to any one of claims 1 to 5,

8. R ３ and R ７ The composition of any one of claims 1 to 7, wherein is H.

9. R ３ and R ７ However, individually, C １ -C ６ The composition of any one of claims 1 to 7, wherein the alkyl group is alkyl.

10. R ３ and R ７ But, CH ３ 10. The composition of claim 9, wherein

11. R ４ C may be substituted with one or more hydroxyl groups １ -C ４ The composition of any one of claims 1 to 10, wherein the alkyl group is alkyl.

12. R ４ The composition of claim 11, wherein is a methyl group optionally substituted with one or more hydroxyl groups.

13. R ４ is terminally substituted with said one or more hydroxyl groups.

14. R ４ The composition of any one of claims 1 to 13, wherein is substituted with two or more hydroxyl groups.

15. R ４ But, CH ２ CH (CH ３ 14. The composition according to claim 1, wherein R is 0 or 1.

16. R ４ C, which may be substituted with one or more amine or ammonium groups; １ -C ４ The composition of any one of claims 1 to 10, wherein the alkyl group is alkyl.

17. R ４ The composition of claim 16, wherein is a methyl group optionally substituted with one or more amine or ammonium groups.

18. R ４ But one or more ＋ N (CH ３ ) ３ 18. The composition of claim 16 or claim 17, which is terminally substituted with a group.

19. R ４ But, CH ２ C (CH ３ ) ２ -N(CH ３ ) ３ ＋ The composition according to any one of claims 1 to 10 or 16,

20. R ２ and R ６ The composition of any one of claims 1 to 19, wherein is H.

21. R ２ and R ６ The composition of any one of claims 1 to 19, wherein is hydroxyl.

22. R ２ and R ６ But, CH ３ The composition according to any one of claims 1 to 19,

23. R ２ and R ６ But N(CH ３ ) ２ or ＋ N (CH ３ ) ３ The composition according to any one of claims 1 to 19,

24. R at each occurrence ８ and R １０ C may be individually substituted with one or more hydroxyl groups １ -C ６ The composition of any one of claims 1 to 23, wherein the alkyl group is alkyl.

25. R at each occurrence ８ and R １０ But, CH ３ The composition according to any one of claims 1 to 24,

26. R ８ and R １０ But, CH ３ and C(CH ３ ) ２ CH ２ The composition of any one of claims 1 to 24, wherein the alkyl group is selected from the group consisting of OH.

27. X － The composition of any one of claims 1 to 26, wherein is a halide, sulfate, methosulfate, carbonate, carboxylate, phosphate, or hydroxide.

28. X － The composition of any one of claims 1 to 27, wherein is a hydroxide.

29. The compound of formula I is The composition of any one of claims 1 to 28, which is a compound of formula IA selected from the group consisting of: and combinations of two or more thereof.

30. 30. The composition of claim 29, wherein said compound of formula I is a compound of formula IA selected from the group consisting of DMAMPD, iso-DMAMPD, and combinations thereof.

31. The compound of formula II is The composition of any one of claims 1 to 30, which is a compound of formula IIA selected from the group consisting of:

32. 32. The composition of claim 31, wherein said compound of formula II is a compound of formula IIA which is DMAMPD-AH.

33. The compound of formula I is The composition of any one of claims 1 to 32, which is a compound of formula I selected from the group consisting of: and combinations of two or more thereof.

34. The compound of formula II is and combinations of two or more thereof.

35. 35. The composition of any one of claims 1 to 34, having from about 0.1% to about 80% by weight of said compound of formula I, said compound of formula II, or a combination thereof, based on the total composition.

36. 36. The composition of any one of claims 1 to 35, having from about 1% to about 50% by weight of said compound of formula I, said compound of formula II, or a combination thereof, based on the total composition.

37. 37. The composition of any one of claims 1 to 36, which is an electronics 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.

38. 38. The composition of claim 37, wherein the electronic device processing composition is a wafer cleaning composition, anisotropic etching composition, photolithography composition, photoresist developing composition, post chemical mechanical planarization cleaning composition, printed circuit board cleaning composition, or a combination of two or more thereof.

39. 39. The composition of any one of claims 1 to 38, further comprising a stabilizer (e.g., an antioxidant, oxygen scavenger, or reducing agent, such as dithionite salts, amines, hydroxylamines, sulfites, hydroquinones, hydrides, carboxylic acids, piperazines, formaldehyde, thioureas, borates, butylated hydroxytoluene, butylated hydroxyanisole, ascorbic acid, and the like, and combinations of two or more thereof).

40. The composition of any one of claims 1 to 39, further comprising a rust inhibitor.

41. The composition of any one of claims 1 to 40, further comprising alcohol, pyrocatechol, glycerin, and / or a glycerin derivative.

42. The composition of any one of claims 1 to 41, wherein the compound of formula I and / or the compound of formula II is an etching agent.

43. 43. The composition of any one of claims 1 to 42, further comprising a hydroxylamine (e.g., hydroxylamine, hydroxylamine sulfate, hydroxylamine chloride, hydroxylamine oxalate, N,N-diethylhydroxylamine, isopropylhydroxylamine, dimethylhydroxylamine hydrochloride, and / or hydroxylamine phosphate).

44. The composition of any one of claims 1 to 43, further comprising an inorganic alkaline compound.

45. The composition of any one of claims 1 to 44, further comprising water.

46. The composition of any one of claims 1 to 45, further comprising a hydrotropic component.

47. The composition of any one of claims 1 to 46, further comprising a pH adjusting agent, a buffering agent, or a combination thereof.

48. 48. The composition of any one of claims 1 to 47, further comprising at least one organic solvent or surfactant (e.g., DMSO, alcohol, ethoxylated alcohol, betaine, alkylsulfonic acid, arylsulfonic acid, or a combination of two or more thereof).

49. The composition of any one of claims 1 to 48, further comprising a rheology modifier (e.g. a polymeric rheology modifier such as polyacrylic acid).

50. The composition of any one of claims 1 to 49, further comprising a chelating agent (e.g., ethylenediaminetetraacetic acid ("EDTA")).

51. 51. The composition of any one of the preceding claims, comprising up to 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.

52. 52. The composition of any one of claims 1 to 51, having reduced toxicity based on rat skin toxicity compared to a composition containing the same weight percent of tetramethylammonium hydroxide (TMAH).

53. The composition of any one of claims 1 to 52, which is essentially free of TMAH.

54. A compound of formula I or a compound of formula II according to any one of claims 1 to 34.

55. 55. A process for making the compound of formula II according to claim 54, comprising: Providing a solution comprising a compound of formula I according to any one of claims 1 to 34 and an organic solvent; Optionally, heating the solution to about 25° C. to about 45° C.; adding a methylating agent to the solution to form a mixture, the methylating agent being optionally added over a period of about one hour; mixing the mixture; and Optionally, cooling the mixture to less than about 20° C.; Optionally filtering the mixture. The process includes:

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