# US 2009/0267239 A1 · Positive photosensitive resin composition

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- Number: US 2009/0267239 A1
- Document ID: US20090267239A1
- Status: Published application
- Kind: A1
- Application number: 12/065,325
- Filed: 2006-09-01
- Published: 2009-10-29
- Earliest claimed: 2005-09-05
- Assignees: Asahi Kasei EMD Corporation; Pi R&D Co., Ltd.
- Inventors: Takayuki Kanada; Hiroyuki Hanahata; Xingzhou Jin; Shuzo Waki
- Web page: https://patentgrep.com/patent/US20090267239A1

## CPC

- G03F 7/0233: {characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides}
- G03F 7/022: Quinonediazides (G03F7/075 takes precedence)
- G03F 7/40: Treatment after imagewise removal, e.g. baking
- 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

A photosensitive resin composition comprising parts by mass of polycondensate (A) having a structure resulting from dehydration condensation between one or two or more tetracarboxylic acid dianhydride and one or two or more armatic diamines having mutually ortho-positioned amino and phenolic hydroxyl groups and 1 to 100 parts by mass of photosensitive diazonaphthoquinone compound (B), wherein the polycondensate (A) has a weight average molecular weight of 3000 to 70,000.

## Claims

### Claim 1

A photosensitive resin composition comprising 1 to 100 parts by mass of a photosensitive diazonaphthoquinone compound (B) based on 100 parts by mass of a polycondensate (A), which has a structure formed from dehydration condensation of one or more tetracarboxylic dianhydrides and one or more aromatic diamines having an amino group and a phenolic hydroxyl group which are located at ortho positions with respect to each other, wherein the polycondensate (A) has a weight average molecular weight of 3,000 to 70,000.

### Claim 2 (depends on 1)

The photosensitive resin composition according to claim 1, wherein the polycondensate (A) has a structure formed from dehydration condensation of a tetracarboxylic dianhydride comprising at least one selected from the group consisting of bicyclo(2,2,2)-oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride and bis(3,4-dicarboxyphenyl)ether dianhydride and an aromatic diamine comprising at least one selected from the group consisting of bis(3-amino-4-hydroxyphenyl)sulfone, 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane and 3,3′-dihydroxy-4,4′-diaminobiphenyl.

### Claim 3 (depends on 2)

The photosensitive resin composition according to claim 2, wherein the polycondensate (A) has a structure formed from dehydration condensation of a tetracarboxylic dianhydride comprising bicyclo(2,2,2)-oct-7-ene-2,3,5,6-tetracarboxylic dianhydride and an aromatic diamine comprising bis(3-amino-4-hydroxyphenyl)sulfone.

### Claim 4 (depends on 3)

The photosensitive resin composition according to claim 3, wherein the polycondensate (A) has a structure formed from dehydration condensation of a tetracarboxylic dianhydride comprising bicyclo(2,2,2)-oct-7-ene-2,3,5,6-tetracarboxylic dianhydride and an aromatic diamine comprising bis(3-amino-4-hydroxyphenyl)sulfone, and wherein the bis(3-amino-4-hydroxyphenyl)sulfone is in a range of 20 to 40 mol % based on all raw material monomers including all of the tetracarboxylic dianhydride and all of the aromatic diamine, a molar ratio between total number of moles of the tetracarboxylic dianhydride and total number of moles of the aromatic diamine is in a range of 1:0.75 to 0.87 or 0.75 to 0.87:1, and the polycondensate (A) has a weight average molecular weight in the range of 5,000 to 17,000.

### Claim 5 (depends on 1)

The photosensitive resin composition according to claim 1, wherein the photosensitive diazonaphthoquinone compound (B) is at least one compound selected from the group consisting of a 1,2-naphthoquinonediazide-4-sulfonate of a polyhydroxy compound represented by one of the following general formulae (1) to (6) and a 1,2-naphthoquinonediazide-5-sulfonate of the polyhydroxy compound,
wherein k, l, m and n each independently represent 1 or 2; R1 to R10 each independently represent at least one monovalent group selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an alkoxy group, an allyl group and an acyl group; and Y1 to Y3 each independently represent at least one divalent group selected from the group consisting of a single bond, —O—, —S—, —SO—, —SO2—, —CO—, —CO2—, cyclopentylidene, cyclohexylidene, phenylene and an organic group represented by the following chemical formulae,
wherein R11 and R12 each independently represent at least one monovalent group selected from the group consisting of a hydrogen atom, an alkyl group, an alkenyl group, an allyl group and a substituted allyl group; R13 to R16 represent a hydrogen atom or an alkyl group which may be the same or different; w represents an integer of 1 to 5; and R17 to R20 represent a hydrogen atom or an alkyl group which may be the same or different;
wherein Z represents at least one tetravalent group selected from the organic groups represented by the following chemical formulae; R21, R22, R23 and R24 each independently represent a monovalent organic group; b represents 0 or 1; a, c, d and e each independently represent an integer of 0 to 3; and f, g, h and i each independently represent an integer of 0 to 2;
wherein k represents an integer of 3 to 8; k×j L's each independently represent a monovalent organic group having one or more carbon atoms; j represents an integer of 1 to 5; and k T's and k S's each independently represent a monovalent group selected from the group consisting of a hydrogen atom and a monovalent organic group;
wherein A represents a divalent organic group containing an aliphatic tertiary or quaternary carbon atom; and M represents at least one divalent group selected from the groups represented by the following chemical formulae;
wherein each R25 represents a monovalent group represented by the following chemical formula, and may be the same or different; and each q independently represents an integer of 0 to 2,
wherein each R26 independently represents at least one monovalent organic group selected from the group consisting of an alkyl group and a cycloalkyl group; and each r independently represents an integer of 0 to 2; and
wherein R27 represents at least one monovalent organic group selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group and a cycloalkyl group.

### Claim 6 (depends on 1)

A method for forming a cured relief pattern, comprising: a coating step for forming the photosensitive resin composition according to claim 1 on a substrate in a form of a layer or a film; an exposure step for exposing the layer or film with actinic rays through a mask or for directly irradiating the layer or film with light rays, an electron beam or an ion beam; a developing step for eluting or removing the exposed portions or irradiated portions with a developing solution; and a heating step for heating an obtained relief pattern.

### Claim 7 (depends on 5)

A method for forming a cured relief pattern, comprising: a coating step for forming the photosensitive resin composition according to claim 5 on a substrate in a form of a layer or a film; an exposure step for exposing the layer or film with actinic rays through a mask or for directly irradiating the layer or film with light rays, an electron beam or an ion beam; a developing step for eluting or removing the exposed portions or irradiated portions with a developing solution; and a heating step for heating an obtained relief pattern.

### Claim 8 (depends on 6)

A semiconductor device comprising the cured relief pattern obtained by the formation method according to claim 6.

### Claim 9 (depends on 7)

A semiconductor device comprising the cured relief pattern obtained by the formation method according to claim 7.