# US 7,612,146 B2 · Polymeric compositions and uses therefor

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 7,612,146 B2
- Document ID: US7612146B2
- Status: Granted
- Kind: B2
- Application number: 11/220,814
- Filed: 2005-09-07
- Published: 2006-02-02
- Granted: 2009-11-03
- Earliest claimed: 2001-12-12
- Assignees: Sumitomo Bakelite Co., Ltd.
- Inventors: Larry F. Rhodes; Richard Vicari; Leah J. Langsdorf; Andrew A. Sobek; Edwin P. Boyd; Brian Bennett
- Web page: https://patentgrep.com/patent/US7612146B2

## CPC

- C08G 61/06: prepared by ring-opening of carbocyclic compounds
- G03F 7/0046: {with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence)}
- G03F 7/0395: {the macromolecular compound having a backbone with alicyclic moieties}
- G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain}
- 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)

## Abstract

The present invention relates to polycyclic polymers, methods for producing polycyclic polymers, and methods for their use as photoresists in the manufacture of integrated circuits. In one embodiment, the present invention relates to photoresist compositions formed from the polymerization of at least one halogenated polycyclic monomer or hydrohalogenated polycyclic monomer. In another embodiment, the present invention relates to photoresist compositions formed from the co-polymerization of at least one halogenated polycyclic monomer or hydrohalogenated polycyclic monomer with at least one non-halogenated polycyclic monomer.

## Claims

### Claim 1

A polycyclic addition polymer comprising a hydrogenated olefinic end group, a hydrosilated olefinic end group or a hydroformylated olefinic end group on one or both terminal ends thereof.

### Claim 2 (depends on 1)

The polymer of claim 1 comprising repeating units selected from one or more types of repeating units represented by formula I′ or II′:
wherein R1 to R4 independently represent hydrogen, linear or branched (C1 to C30) alkyl, linear and branched (C1 to C24) halohydrocarbyl, linear or branched (C2 to C30) olefin; —(CH2)n—C(O)OR*, —(CH2)n—C(O)OR, —(CH2)n—OR, —(CH2)n—OC(O)R, —(CH2)n—C(O)R, —(CH2)n—OC(O)OR, —(CH2)n—C(R)2—CH(R)(C(O)OR**), —(CH2)n—(CR2)n—CH(R)(C(O)OR**), —(CH2)n—C(OR***)—(CF3)2, —(CR′2)n—O—R— and —(CH2)n—C(R)2—CH(C(O)OR**)2; where R represents hydrogen, linear and branched (C1 to C10) alkyl, and —(CH2)s—OH; R′ represents hydrogen or a halogen; R* represents an acid labile moiety; R** independently represents R or R*; R*** represents —CH2OR, —C(O)OR or —C(O)R; n is an integer from 0 to 10; m is an integer from 0 to 5, s is an integer from 1 to 10; and Z represents oxygen, sulfur, —NH—, or —(CH2)p—, where R″ is hydrogen and p is equal to 1 or 2; and
wherein R5 to R8 independently represent hydrogen, linear or branched (C1 to C30) alkyl, linear or branched (C2 to C30) olefin; —(CH2)n—C(O)OR*, —(CH2)n—C(O)OR, —CH(R)(C(O)OR**), —(CH2)n—(CR2)n—CH(R)(C(O)OR**), —(CR′2)n—O—R— and —(CH2)n—C(R)2—CH(C(O)OR**)2; where Z including p, R′, R*, R**, n and m are as defined above and R represents hydrogen, linear and branched (C1 to C10) alkyl.

### Claim 3 (depends on 2)

The polymer of claim 2 wherein Z is methylene.

### Claim 4 (depends on 3)

The polymer of claim 3 comprising a type of repeating unit having a pendent halohydrocarbyl represented by the formula CrX″2r+1 wherein X″ is independently selected from fluorine, chlorine, bromine and iodine, and r is an integer from 1 to 20.

### Claim 5 (depends on 3)

The polymer of claim 3 comprising a type of repeating unit represented by the formula:
wherein n is an integer from 0 to 10 and R*** is as previously defined.

### Claim 6 (depends on 1)

The polymer of claim 1 where one type of repeating units comprises a pendant acid labile group.

### Claim 7 (depends on 6)

The polymer of claim 6, comprising repeating units selected from one or more types of repeating units represented by formula I′ or II′:
wherein R1, to R4 independently represent hydrogen, linear or branched (C1 to C30) alkyl, linear and branched (C1 to C24) halohydrocarbyl, linear or branched (C2 to C30) olefin; —(CH2)n—C(O)OR*, —(CH2)n—C(O)OR, —(CH2)n—OR, —(CH2)n—OC(O)R, —(CH2)n—C(O)R, —(CH2)n—OC(O)OR, —(CH2)n—C(R)2—CH(R)(C(O)OR**), —(CH2)n—(CR2)n—CH(R)(C(O)OR**), —(CH2)n—C(OR***)—CF3)2, —(CR′2)n—O—R— and —(CH2)n—C(R)2—CH(C(O)OR**)2; where R represents hydrogen, linear and branched (C1 to C10) alkyl; R′ represents hydrogen or a halogen; R* represents an acid labile moiety; R** independently represents R or R*; R*** represents —CH2OR, —C(O)OR or —C(O)R; n is an integer from 0 to 10; m is an integer from 0 to 5; and Z represents oxygen, sulfur, —NH—, or —(CH2)p—, and p is equal to 1 or 2;
wherein R5 to R8 independently represent hydrogen, linear or branched (C1 to C30) alkyl, linear or branched (C2 to C30) olefin; —(CH2)n—C(O)OR*, —(CH2)n—C(O)OR, —(CH2)n—OR, —(CH2)n—OC(O)R, —(CH2)n—C(O)R, —(CH2)n—OC(O)OR, —(CH2)n—C(R)2—CH(R)(C(O)OR**), —(CH2)n—(CR2)n—CH(R)(C(O)OR**), —(CR′2)n—O—R— and —(CH2)n—C(R)2—CH(C(O)OR**)2; where R represents hydrogen, linear and branched (C1 to C10) alkyl, —(CH2)s—OH where s is an integer from 1 to 10; Z including p, R′, R*, R**, n and m are as defined above.

### Claim 8 (depends on 7)

The polymer of claim 7 wherein Z is methylene.

### Claim 9 (depends on 8)

The polymer of claim 8 wherein at least one of R5 to R8 is selected from the group represented by the formula —(CH2)n—C(O)OR*.

### Claim 10 (depends on 9)

The polymer of claim 9, wherein at least one of R′ to R4 is a halohydrocarbyl represented by the formula CrX″2r+1 wherein X″ is independently selected from fluorine, chlorine, bromine and iodine, and r is an integer from 1 to 20.

### Claim 11 (depends on 8)

The polymer of claim 8 comprising a type of repeating unit represented by the formula:
wherein n is an integer from 0 to 10 and R*** is as previously defined.