# US 9,434,750 B2 · Branched siloxanes and methods for synthesis

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- Number: US 9,434,750 B2
- Document ID: US9434750B2
- Status: Granted
- Kind: B2
- Application number: 14/681,416
- Filed: 2015-04-08
- Published: 2015-10-01
- Granted: 2016-09-06
- Earliest claimed: 2010-02-19
- Assignees: Board of Regents, The University of Texas System
- Applicants: Board of Regents, The University of Texas System
- Inventors: C. Grant Willson; Tsuyoshi Ogawa; Michael B. Jacobsson
- Web page: https://patentgrep.com/patent/US9434750B2

## CPC

- 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)}
- C07D 301/00: Preparation of oxiranes
- C07D 303/12: with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07F 7/0874: {Reactions involving a bond of the Si-O-Si linkage}
- C07F 7/0878: {Si-C bond}
- C07F 7/0879: {Hydrosilylation reactions}
- C07F 7/0889: {Reactions not involving the Si atom of the Si-O-Si sequence}
- C07F 7/0896: {Compounds with a Si-H linkage}
- C09D 163/00: Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
- G03F 7/0002: {Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping}
- H10P 95/064: {the removal being chemical etching}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10

## Abstract

The present invention describes branched and functionalized siloxanes and methods for making such compounds. The compounds have a variety of uses. One preferred application is as novel planarizing material for lithography, in which case functionalized branched siloxane, such as an epoxy-modified branched siloxane is particularly useful.

## Claims

### Claim 1

A method for synthesizing branched siloxanes, comprising, reacting i) a siloxane which has a silicon-hydrogen bond represented by the formula (a),
wherein n represents a whole number between 1 and 20, with ii) an asymmetric linear siloxane of formula (b),
wherein X represents any halogen and m represents a whole number between 2 to 10, said reacting performed under conditions such that a branched siloxane and byproducts are produced.

### Claim 2 (depends on 1)

The method of claim 1, wherein said siloxane comprising a silicon-hydrogen bond represented by the formula (a) is 3H,5H-octamethyltetrasiloxane.

### Claim 3 (depends on 1)

The method of claim 1, wherein m is either 2 or 3.

### Claim 4 (depends on 2)

The method of claim 2, wherein said 3H,5H-octamethyltetrasiloxane, prior to reacting with said asymmetric linear siloxane, is exposed to a catalyst in the presence of water.

### Claim 5 (depends on 4)

The method of claim 4, wherein said catalyst is removed prior to reacting said 3H,5H-octamethyltetrasiloxane with said asymmetric linear siloxane.

### Claim 6 (depends on 4)

The method of claim 4, wherein said catalyst is a palladium catalyst.

### Claim 7 (depends on 1)

The method of claim 1, wherein the halogen of said asymmetric linear siloxane is chlorine.

### Claim 8 (depends on 1)

The method of claim 1, further comprising the step of purifying the branched siloxane by distillation, so as to remove said byproducts of the synthesis reaction and provide a purified branched siloxane.

### Claim 9 (depends on 8)

The method of claim 8, further comprising the step of fiinctionalizing said purified branched siloxane.

### Claim 10 (depends on 9)

The method of claim 9, wherein said functionalizing comprises attaching photocrosslinkable moieties, said moieties selected from the group consisting of acrylates, methacrylates, vinyls and epoxides.

### Claim 11 (depends on 9)

The method of claim 9, wherein said functionalizing comprises hydrosylilation.