# US 11,999,890 B2 · Surfactants for electronics

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- Number: US 11,999,890 B2
- Document ID: US11999890B2
- Status: Granted
- Kind: B2
- Application number: 17/871,208
- Filed: 2022-07-22
- Published: 2022-12-01
- Granted: 2024-06-04
- Earliest claimed: 2020-02-05
- Assignees: AdvanSix Resins & Chemicals LLC
- Applicants: AdvanSix Resins & Chemicals LLC
- Inventors: Edward Asirvatham
- Web page: https://patentgrep.com/patent/US11999890B2

## CPC

- C09K 13/06: with organic material
- H10F 77/703: {of the semiconductor bodies, e.g. textured active layers}
- C07F 7/0838: {Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21)}
- C09K 13/00: Etching, surface-brightening or pickling compositions (for glass C03C15/00, {C03C25/66; for mortars, concrete, artificial or natural stone or ceramics C04B41/5338}; for metallic material C23F, C23G1/00, C25F1/00; {for semi-conductors H10P52/40})
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10F: INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Pre-texturing agents, etchants, and photoresist stripping agents may be formulated to include one or more surfactants, from one or more surfactant classes, such as siloxane derivatives of amino acids that have surface-active properties.

## Claims

### Claim 1

A formulation for an etchant, comprising:
at least one surfactant of Formula I,
wherein R1 and R2 may be the same or different, and comprise at least one group selected from the group consisting of C1-C6 alkyl, optionally the C1-C6 alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;
n is an integer from 1 to 12;
the terminal nitrogen is optionally further substituted with R3, wherein R3 is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C1-C6 alkyl;
an optional counterion associated with the compound which, if present, is selected from the group consisting of chloride, bromide, and iodide; and
hydrofluoric acid (HF).

### Claim 2 (depends on 1)

The formulation of claim 1, further comprising one or more oxidizing agents.

### Claim 3 (depends on 1)

The formulation of claim 1, further comprising one or more complexing agents.

### Claim 4 (depends on 1)

The formulation of claim 1, wherein n is 5.

### Claim 5 (depends on 1)

The formulation of claim 1, wherein the surfactant is 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexanamide, having the following formula:

### Claim 6 (depends on 1)

The formulation of claim 1, wherein the surfactant is 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexaminium chloride, having the following formula:

### Claim 7 (depends on 1)

The formulation of claim 1, wherein the surfactant is 3 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

### Claim 8 (depends on 1)

The formulation of claim 1, wherein the surfactant is 6-((3-(1,1, 1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexan-1-amine oxide, having the following formula:

### Claim 9 (depends on 1)

The formulation of claim 1, wherein the surfactant is 4-((6-((3-(1,1, 1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

### Claim 10

A formulation for a photoresist stripping formulation, comprising:
at least one surfactant of Formula I,
wherein R1 and R2 may be the same or different, and comprise at least one group selected from the group consisting of C1-C6 alkyl, optionally the C1-C6 alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;
n is an integer from 1 to 12;
the terminal nitrogen is optionally further substituted with R3, wherein R3 is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C1-C6 alkyl;
an optional counterion associated with the compound which, if present, is selected from the group consisting of chloride, bromide, and iodide; and
an alkanolamine.

### Claim 11 (depends on 10)

The formulation of claim 10, further comprising a sulfoxide.

### Claim 12 (depends on 10)

The formulation of claim 10, further comprising a sulfone.

### Claim 13 (depends on 10)

The formulation of claim 10, further comprising a glycol ether.

### Claim 14 (depends on 10)

The formulation of claim 10, wherein n is 5.

### Claim 15 (depends on 10)

The formulation of claim 10, wherein the surfactant is 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexanamide, having the following formula:

### Claim 16 (depends on 10)

The formulation of claim 10, wherein the surfactant is 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexaminium chloride, having the following formula:

### Claim 17 (depends on 10)

The formulation of claim 10, wherein the surfactant is 3 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

### Claim 18 (depends on 10)

The formulation of claim 10, wherein the surfactant is 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexan-1-amine oxide, having the following formula:

### Claim 19 (depends on 10)

The formulation of claim 10, wherein the surfactant is 4-((6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula: