# US 7,745,077 B2 · Composition for coating over a photoresist pattern

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- Number: US 7,745,077 B2
- Document ID: US7745077B2
- Status: Granted
- Kind: B2
- Application number: 12/141,307
- Filed: 2008-06-18
- Published: 2009-12-24
- Granted: 2010-06-29
- Earliest claimed: 2008-06-18
- Assignees: AZ Electronic Materials USA Corp.
- Inventors: Muthiah Thiyagarajan; Yi Cao; Sung Eun Hong; Ralph R. Dammel
- Web page: https://patentgrep.com/patent/US7745077B2

## CPC

- C09D 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09D 133/066: {containing -OH groups}
- C09D 139/00: Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers
- G03F 7/40: Treatment after imagewise removal, e.g. baking
- 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)

## Abstract

The present invention relates to an aqueous coating composition for coating a photoresist pattern, comprising a polymer comprising at least one unit with an alkylamino group, where the unit has a structure (1), where, R1 to R5 are independently selected from hydrogen and C1 to C6 alkyl, and W is C1 to C6 alkyl. The invention also relates to a process for imaging a photoresist layer using the present composition.

## Claims

### Claim 1

An aqueous coating composition for coating a photoresist pattern, comprising a polymer soluble in water and comprising at least one unit with an alkylamino group, where the unit has a structure (1),
where, R1 to R5 are independently selected from hydrogen and C1 to C6 alkyl, and W is C1 to C6 alkylene, further where the composition is free of carboxylic acid group.

### Claim 2 (depends on 1)

The coating composition of claim 1, where the polymer further comprises a monomeric unit of structure 2,
where, R6 to R8 are independently selected from hydrogen and C1 to C6 alkyl, A is selected from a single bond, O, C(O), (C═O)O, C1 to C4 alkyl;
X, Y, Z and N form a cyclic structure, further where, X is selected from C1 to C6 alkylene, unsaturated C1 to C6 alkylene, direct bond, and mixtures thereof, Y is selected from C1 to C6 alkylene, unsaturated C1 to C6 alkylene, direct bond, and mixtures thereof, Z is selected from O, C(O), and N, and N is nitrogen.

### Claim 3 (depends on 2)

The coating composition of claim 2, where the monomeric unit of structure (2)is selected from,
where, R6 to R8 are independently selected from hydrogen and C1 to C6 alkyl, X, Y, Z and N form a cyclic structure, further where, X is selected from C1 to C6 alkylene, unsaturated C1 to C6 alkylene, direct bond, and mixtures thereof, Y is selected from C1 to C6 alkylene, unsaturated C1 to C6 alkylene, direct bond, and mixtures thereof, Z is selected from O, C(O), N and N is nitrogen.

### Claim 4 (depends on 2)

The coating composition of claim 2, where the monomeric unit of structure (2) is selected from,

### Claim 5 (depends on 1)

The coating composition of claim 1, where W is ethylene.

### Claim 6 (depends on 1)

The coating composition of claim 1, where the composition is free of amido group.

### Claim 7 (depends on 1)

The coating composition of claim 1, where the polymer is free of amido group.

### Claim 8 (depends on 1)

The coating composition of claim 1, where the polymer further comprises a monomeric unit of structure (3),
where B is C1 to C6 alkylene, R9 is H or C1 to C6 alkyl.

### Claim 9 (depends on 1)

The composition of claim 1, where the composition further contains a water miscible solvent.

### Claim 10 (depends on 1)

The composition of claim 1, where the composition further contains a water miscible solvent selected from (C1-C8)alcohols, diols, triols, ketones, esters, lactates, amides, ethylene glycol monoalkyl ethers, ethylene glycol monoalkyl ether acetate, N-methyl pyrrolidone, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether acetate.

### Claim 11 (depends on 1)

The composition of claim 1, where the composition further comprises additives selected from surfactant, aminoalcohol, amine, C1-C8alcohol, photoacid generator, crosslinking compound, thermal acid generator, and free acid.

### Claim 12 (depends on 1)

The composition of claim 1, where the composition is free of a crosslinking compound.

### Claim 13 (depends on 1)

The composition of claim 1, where the composition is free of a photoacid generator.

### Claim 14

A process for manufacturing a microelectronic device, comprising;
a) providing a substrate with a photoresist pattern;
b) coating the photoresist pattern with an aqueous coating composition for coating a photoresist pattern, comprising a polymer comprising at least one unit with an alkylamino group, where the unit has a structure (1),
where, R1 to R5 are independently selected from hydrogen and C1 to C6 alkyl, and W is C1 to C6 alkylene, further where the composition is free of carboxylic acid goup;
c) reacting a portion of the coating material in contact with the photoresist pattern;
d) removing a portion of the coating material which is not reacted with a removal solution.

### Claim 15 (depends on 14)

The process according to claim 14, where the substrate is heated, thereby causing a reaction of the coating material with the photoresist.

### Claim 16 (depends on 14)

The process according to claim 14, where the removal solution is an aqueous solution comprising a hydroxide base.

### Claim 17 (depends on 14)

The process according to claim 14, where the removal solution further comprises a water-miscible solvent.

### Claim 18 (depends on 14)

The process of claim 14, where the photoresist comprises a polymer and a photoacid generator.

### Claim 19

An aqueous coating composition for coating a photoresist pattern, comprising a single polymer, where the polymer comprises at least one unit with an alkylamino group of structure (1) and at least one monomeric unit selected from,
and where structure (1) is,
where, R1 to R5 are independently selected from hydrogen and C1 to C6 alkyl, and W is C1 to C6 alkylene, further where the composition is free of carboxylic acid group.
