# US 7,745,096 B2 · Photosensitive polyimide composition, polyimide film and semiconductor device using the same

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- Number: US 7,745,096 B2
- Document ID: US7745096B2
- Status: Granted
- Kind: B2
- Application number: 11/861,948
- Filed: 2007-09-26
- Published: 2008-08-07
- Granted: 2010-06-29
- Earliest claimed: 2007-02-01
- Assignees: Samsung Electronics Co., Ltd.
- Inventors: Myung Sup Jung; Sang Mock Lee; Jingyu Lee
- Web page: https://patentgrep.com/patent/US7745096B2

## CPC

- C08L 79/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G 73/101: {containing chain terminating or branching agents}
- C08G 73/1014: {in the form of (mono)anhydrid}
- C08G 73/1039: {comprising halogen-containing substituents}
- G03F 7/0392: {the macromolecular compound being present in a chemically amplified positive photoresist composition}
- Y10S 430/107: Polyamide or polyurethane
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

A photosensitive polyimide composition, a polyimide film, and a semiconductor device using the same are disclosed. The photosensitive polyimide composition can be cured by heating. A polyhydroxyimide is used as a base resin and can be mixed with a photoacid generator and a cross-linking agent having two or more vinylether groups. A film of the photosensitive polyimide composition can be developed by treatment with an alkaline aqueous solution. Embodiments of the invention enable improvement in production yield and reliability in a highly-integrated memory semiconductor packaging processes.

## Claims

### Claim 1

A photosensitive polyimide composition comprising polyhydroxyimide, a cross-linking agent comprising two or more vinylether groups, and a photoacid generator.

### Claim 2 (depends on 1)

The photosensitive polyimide composition of claim 1, wherein the polyhydroxyimide is expressed by the following chemical formula 1:
where X is a quadrivalent aromatic group or an aliphatic organic group, Y is the quadrivalent aromatic group or the aliphatic organic group, Z is H or a cross-linkable monovalent organic group, and n is an integer between 1 and 1000.

### Claim 3 (depends on 2)

The photosensitive polyimide composition of claim 2, wherein X in chemical formula 1 is selected from a group consisting of

### Claim 4 (depends on 2)

The photosensitive polyimide composition of claim 2, wherein Y in chemical formula 1 is selected from a group consisting of

### Claim 5 (depends on 2)

The photosensitive polyimide composition of claim 2, wherein Z in chemical formula 1 is selected from a group consisting of H,

### Claim 6 (depends on 1)

The photosensitive polyimide composition of claim 1, wherein the photoacid generator comprises a halide-based compound, a sulfonic compound, an ammonium salt compound, a diazonium salt compound, an iodine salt compound, a sulfonium salt compound, a phosphonium salt compound, an onium salt polymeric compound, a selenium salt compound, or an azonium salt compound, or a combination of at least one of the foregoing compounds.

### Claim 7 (depends on 1)

A polyimide film in which the photosensitive polyimide composition of claim 1 is coated on a wafer, exposed, developed in an alkaline aqueous solution, and cured by heat.

### Claim 8 (depends on 7)

The polyimide film of claim 7, wherein the alkaline aqueous solution comprises a quaternary ammonium hydroxide aqueous solution, an amine-based aqueous solution, or a combination of the foregoing solutions.

### Claim 9 (depends on 8)

The polyimide film of claim 8, wherein the quaternary ammonium hydroxide aqueous solution is a tetramethylammoniumhydroxide or a tetraethylammoniumhydroxide aqueous solution, and the amine-based aqueous solution is an ethanol amine aqueous solution or a propylamine aqueous solution.

### Claim 10 (depends on 7)

A semiconductor device comprising the polyimide film of claim 7.

### Claim 11 (depends on 7)

The polyimide film of claim 7, wherein the film is cured at a temperature of about 150° C. or less.

### Claim 12

A method of integrated circuit redistribution, the method comprising:
providing a wafer; and
forming a redistribution layer on the wafer using photolithographic process with a photosensitive polyimide composition, the photosensitive polyimide composition comprising polyhydroximide, a cross-linking agent comprising two or more vinylether groups, and a photoacid generator.

### Claim 13

A method of chip scale packaging, the method comprising:
providing a wafer; and
forming a redistribution layer on the wafer using photolithographic process with a photosensitive polyimide composition, the photosensitive polyimide composition comprising polyhydroximide, a cross-linking agent comprising two or more vinylether groups, and a photoacid generator;
arranging a solder ball on the redistribution layer; and
soldering the solder ball.

### Claim 14

A polyhydroxyimide described by chemical formula 3:
wherein n is 1 to 1000.

### Claim 15

A photolithographic method comprising:
mixing a polyhydroxyimide, a cross-linking agent comprising two or more vinylether groups, and solvent;
adding a photoacid generator to provide a photosensitive polyimide composition;
coating a wafer with the photosensitive polyimide composition;
baking the coated wafer at a temperature of less than about 150° C.;
exposing the coated wafer to light;
treating the coated wafer at a temperature of less than about 150° C.; and
developing the coated wafer in an aqueous solution to provide a wafer with a patterned film.

### Claim 16 (depends on 15)

The method of claim 15, further comprising wherein the photoacid generator comprises a halide based compound, sulfonic compound, an ammonium salt compound, a diazonium salt compound, an iodine salt compound, a sulfonium salt compound, a phosphonium salt compound, an onium salt polymeric compound, a selenium salt compound, and an azonium salt compound, or a combination of at least one of the foregoing compounds.

### Claim 17 (depends on 15)

The method of claim 15, further comprising wherein the aqueous solution comprises tetramethylammoniumhydroxide.

### Claim 18

A photolithographic method comprising:
mixing a polyhydroxyimide, a cross-linking agent comprising two or more vinylether groups, and solvent;
adding a photoacid generator to provide a photosensitive polyimide composition;
coating a wafer with the photosensitive polyimide composition;
pre-baking the coated wafer at a temperature of less than 100° C.;
baking the coated wafer at a temperature of less than about 150° C.;
exposing the coated wafer to light;
treating the coated wafer at a temperature of less than about 150° C.; and
developing the coated wafer in an alkaline aqueous solution to provide a wafer with a patterned film.