# US 7,745,540 B2 · Gap fill materials and bottom anti-reflective coatings comprising hyperbranched polymers

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- Number: US 7,745,540 B2
- Document ID: US7745540B2
- Status: Granted
- Kind: B2
- Application number: 11/852,137
- Filed: 2007-09-07
- Published: 2008-09-04
- Granted: 2010-06-29
- Earliest claimed: 2005-01-11
- Assignees: Brewer Science Inc.
- Inventors: Chelladurai Devadoss; Mandar Bhave; Runhui Huang
- Web page: https://patentgrep.com/patent/US7745540B2

## CPC

- C09D 5/34: Filling pastes (materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12)
- C09D 201/005: {Dendritic macromolecules}
- Y10T 428/2462: with partial filling of valleys on outer surface
- 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)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

New anti-reflective or fill compositions having improved flow properties are provided. The compositions comprise a dendritic polymer dispersed or dissolved in a solvent system, and preferably a light attenuating compound, a crosslinking agent, and a catalyst. The inventive compositions can be used to protect contact or via holes from degradation during subsequent etching in the dual damascene process. The inventive compositions can also be applied to substrates (e.g., silicon wafers) to form anti-reflective coating layers having high etch rates which minimize or prevent reflection during subsequent photoresist exposure and developing.

## Claims

### Claim 1

The combination of a substrate having a surface and a cured protective layer on said surface, said cured protective layer being formed from an anti-reflective coating or fill composition comprising a dendritic polymer, a light attenuating compound, and a crosslinking agent dispersed or dissolved in a solvent system, wherein:
said polymer is a dendritic polymer selected from the group consisting of dendritic polyesters, dendritic polyols, dendritic polyethers, dendritic polyamines, and mixtures thereof;
said crosslinking agent is selected from the group consisting of melamines, glycourils, and mixtures thereof; and
said light attenuating compound is selected from the group consisting of 9-anthracene carboxylic acid, 9-hydroxy methyl anthracene, 3-hydroxy-2-naphthoic acid, 1,4-dihydroxy-2-naphthoic acid, 4-hydroxybenzoic acid, 3,4-hydroxy benzoic acid, and mixtures thereof.

### Claim 2 (depends on 1)

The combination of claim 1, wherein said substrate is a microelectronic substrate.

### Claim 3 (depends on 1)

The combination of claim 1, wherein said substrate comprises a silicon wafer.

### Claim 4 (depends on 1)

The combination of claim 1, wherein said substrate has a hole formed therein, said hole being defined by a bottom wall and sidewalls, and said cured protective layer being in contact with at least a portion of the surfaces of said bottom wall and sidewalls.

### Claim 5 (depends on 4)

The combination of claim 4, wherein the degree of leveling of said cured protective layer in said hole is at least about 85%.

### Claim 6 (depends on 1)

The combination of claim 1, wherein said dendritic polymer is a hyperbranched polymer.

### Claim 7 (depends on 1)

The combination of claim 1, wherein said composition has a viscosity of less than 10 cP.

### Claim 8 (depends on 1)

The combination of claim 1, wherein said composition comprises from about 0.2-10% by weight dendritic polymer, based upon the total weight of the composition taken as 100% by weight.

### Claim 9 (depends on 1)

The combination of claim 1, wherein said composition further comprises a catalyst.

### Claim 10 (depends on 9)

The combination of claim 9, wherein said compound is a catalyst selected from the group consisting of sulfonic acids, carboxylic acids, and mixtures thereof.

### Claim 11 (depends on 1)

The combination of claim 1, wherein said dendritic polymer has an average molecular weight of less than 15,000 g/mole.

### Claim 12 (depends on 1)

The combination of claim 1, wherein said dendritic polymer has a viscosity of less than 150×103 cP.

### Claim 13 (depends on 1)

The combination of claim 1, wherein said dendritic polymer has a hydroxyl number of at least 100 mg KOH/g of dendritic polymer.

### Claim 14 (depends on 1)

The combination of claim 1, wherein said composition comprises from about 90-99% by weight of said solvent system, based upon the total weight of the composition taken as 100% by weight.

### Claim 15 (depends on 1)

The composition of claim 1, wherein said solvent system has a boiling point of from about 100-200° C.
