# US 5,707,776 A · Positive resin composition sensitive to ultraviolet rays

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- Number: US 5,707,776 A
- Document ID: US5707776A
- Status: Granted
- Kind: A
- Application number: 08/438,481
- Filed: 1995-05-10
- Granted: 1998-01-13
- Earliest claimed: 1994-05-12
- Assignees: Fuji Photo Film Co., Ltd.
- Inventors: Yasumasa Kawabe; Tsukasa Yamanaka; Toshiaki Aoai
- Web page: https://patentgrep.com/patent/US5707776A

## CPC

- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- G03F 7/039: Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023)
- Y10S 430/106: Binder containing
- Y10S 430/121: Nitrogen in heterocyclic ring
- Y10S 430/122: Sulfur compound containing
- 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

Disclosed is a positive radiation-sensitive resist composition comprising polymer(s) of the following general formula (1) and a radiation-sensitive agent. ##STR1## Ra, Rb, Rc and Rd each are independently a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an aralkyl group, an alkoxycarbonyl group, an arylcarbonyl group, an acyloxy group, an acyl group, or a cycloalkyl group; k is an integer of from 1 to 30; (1+n) is an integer of from 1 to 100; m is an integer of from 1 to 50; p1, p2 and p3 each are an integer of from 1 to 3; q1 is an integer of from 1 to 4. The resist composition has high resolution to give resist patterns with good profiles and has high heat resistance and good storage stability.

## Claims

### Claim 1

A positive radiation-sensitive resin composition comprising a polymer(s) of formula (1) as a binder and a radiation-sensitive agent: ##STR27## wherein R.sup.a, R.sup.b, R.sup.c and R.sup.d are the same or different and each represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an aralkyl group, an alkoxycarbonyl group, an arylcarbonyl group, an acyloxy group, an acyl group, or a cycloalkyl group;
k represents an integer of from 1 to 30;
(1+n) is an integer of from 1 to 100;
m represents an integer of from 1 to 50;
p1, p2 and p3 each represent an integer of from 1 to 3; and
q1 represents an integer of from 1 to 4.

### Claim 2 (depends on 1)

The positive radiation-sensitive resin composition of claim 1, wherein R.sup.a, R.sup.b, R.sup.c and R.sup.d each is selected from the group consisting of a chlorine atom, a bromine atom, an iodine atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, an alkenyl group having from 2 to 4 carbon atoms, a phenyl group, a xylyl group, a toluyl group, a cumenyl group, a benzyl group, a phenethyl group, a cumyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a benzoyloxy group, a butyryloxy group, an acetoxy group, a formyl group, an acetyl group, a butyryl group, a benzoyl group, a cyanamoyl group, a valeryl group, a cyclopentyl group, and a cyclohexyl group.

### Claim 3 (depends on 1)

The positive radiation-sensitive resin composition of claim 1, wherein the composition contains the polymer of formula (1) in an amount of 10 to 50% by weight.

### Claim 4 (depends on 1)

The positive radiation-sensitive resin composition of claim 1, wherein the polymer of formula (1) has a number average molecular weight of from 300 to 10,000.

### Claim 5 (depends on 1)

The positive radiation-sensitive resin composition of claim 1, wherein the binder further comprises an alkali-soluble polymer.

### Claim 6 (depends on 5)

The positive radiation-sensitive resin composition of claim 5, wherein the amount of the alkali-soluble polymer is 0.1 to 100 parts by weight per 100 parts by weight of the polymer of formula (1).

### Claim 7 (depends on 1)

The positive radiation-sensitive resin composition of claim 1, wherein the amount of the radiation-sensitive agent is 0.1 to 100 parts by weight per 100 parts by weight of the binder.

### Claim 8 (depends on 1)

The positive radiation-sensitive resin composition of claim 1, wherein the radiation-sensitive agent is selected from the group consisting of:
an oxazole derivative of formula (4) and a s-triazine derivative of formula (5): ##STR28## wherein R.sup.1 represents a substituted or unsubstituted aryl or alkenyl group; R.sup.2 represents a substituted or unsubstituted aryl, alkenyl or alkyl group, or --CX.sub.3 where X represents a chlorine atom or a bromine atom; and a plurality of X may be the same or different,
an iodonium salt of formula (6) and a sulfonium salt of formula (7): ##STR29## wherein Ar.sup.1 and Ar.sup.2 each independently represent a substituted or unsubstituted aryl group; R.sup.3, R.sup.4 and R.sup.5 each independently represent a substituted or unsubstituted alkyl or aryl group; Z.sup.- represents a pair anion; and two of R.sup.3, R.sup.4 and R.sup.5, as well as Ar.sup.1 and Ar.sup.2 may be bonded to each other either directly or via a linking group,
a disulfone derivative of formula (8) and an iminosulfonate derivative of formula (9): ##STR30## wherein Ar.sup.3 and Ar.sup.4 each independently represent a substituted or unsubstituted aryl group; R.sup.6 represents a substituted or unsubstituted alkyl or aryl group; and A represents a substituted or unsubstituted alkylene, alkenylene or arylene group, and
a diazo compound of formula (10): ##STR31## wherein Y represents --CO-- or --SO.sub.2 --; R.sup.7 represents a linear, branched or cyclic alkyl group having from 1 to 12 carbon atoms, or a substituted or unsubstituted aryl or aralkyl group.

### Claim 9 (depends on 8)

The positive radiation-sensitive resin composition of claim 8, wherein at least one of Ar.sup.1 and Ar.sup.2 represents a substituted aryl group and the substituent is selected from the group consisting of an alkyl group having from 1 to 6 carbon atoms, a haloalkyl group having from 1 to 6 carbon atoms, a cycloalkyl group, an aryl group, an alkoxy group having from 1 to 6 carbon atoms, a nitro group, a carboxyl group, an alkoxycarbonyl group, a hydroxyl group, a mercapto group, and a halogen atom.

### Claim 10 (depends on 8)

The positive radiation-sensitive resin composition of claim 8, wherein at least one of R.sup.3, R.sup.4 and R.sup.5 represents a substituted aryl group and the substituent is selected from the group consisting of an alkoxy group having from 1 to 8 carbon atoms, an alkyl group having from 1 to 8 carbon atoms, a nitro group, a carboxyl group, a hydroxyl group, and a halogen atom, or at least one of R.sup.3, R.sup.4 and R.sup.5 represents a substituted alkyl group and the substituted is selected from the group consisting of an alkoxy group having from 1 to 8 carbon atoms, a carboxyl group, and an alkoxycarbonyl group having from 2 to 9 carbon atoms.

### Claim 11 (depends on 8)

The positive radiation-sensitive resin composition of claim 8, wherein at least one of Ar.sup.3 and Ar.sup.4 represents a substituted aryl group and the substituent does not contain more than 13 carbon atoms.

### Claim 12 (depends on 8)

The positive radiation-sensitive resin composition of claim 8, wherein R.sup.6 represents a substituted aryl group and the substituent does not contain.

### Claim 13 (depends on 8)

The positive radiation-sensitive resin composition of claim 8, wherein R.sup.7 represents a substituted aryl group or a substituted aralkyl group and the substituent does not contain more than 10 carbon atoms.