# US 10,501,580 B2 · Polyimide precursor composition, photosensitive resin composition, cured film, method for producing cured film, a semiconductor device, and method for producing polyimide precursor composition

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- Number: US 10,501,580 B2
- Document ID: US10501580B2
- Status: Granted
- Kind: B2
- Application number: 15/824,360
- Filed: 2017-11-28
- Published: 2018-03-22
- Granted: 2019-12-10
- Earliest claimed: 2015-05-29
- Assignees: FUJIFILM Corporation
- Applicants: FUJIFILM Corporation
- Inventors: Takeshi Kawabata; Takuma Amemiya; Hidekazu Oohashi; Yu Iwai; Akinori Shibuya
- Web page: https://patentgrep.com/patent/US10501580B2

## CPC

- C08G 73/1067: {Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound}
- C08F 290/145: {Polyamides; Polyesteramides; Polyimides}
- C08G 73/10: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- G03F 7/021: Macromolecular diazonium compounds; Macromolecular additives, e.g. binders {(G03F7/0166 takes precedence)}
- G03F 7/0212: {characterised by the polymeric binder or the macromolecular additives other than the diazo resins or the polymeric diazonium compounds}
- G03F 7/0233: {characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides}
- G03F 7/031: Organic compounds not covered by group G03F7/029
- G03F 7/037: the binders being polyamides or polyimides
- G03F 7/0387: {Polyamides or polyimides}
- G03F 7/0388: {with ethylenic or acetylenic bands in the side chains of the photopolymer}
- G03F 7/162: {Coating on a rotating support, e.g. using a whirler or a spinner}
- G03F 7/168: {Finishing the coated layer, e.g. drying, baking, soaking}
- G03F 7/2004: {characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light}
- G03F 7/322: {Aqueous alkaline compositions}
- G03F 7/325: {Non-aqueous compositions}
- G03F 7/40: Treatment after imagewise removal, e.g. baking
- H01L 23/29
- H01L 23/293
- H01L 23/31
- H01L 24/29
- H01L 25/065
- H01L 25/07
- H01L 25/18
- H01L 24/16
- H01L 24/32
- H01L 24/73
- H01L 25/0657
- H01L 2224/131
- H01L 2224/16145
- H01L 2224/16146
- H01L 2224/16227
- H01L 2224/16238
- H01L 2224/2919
- H01L 2224/32145
- H01L 2224/32225
- H01L 2224/73204
- H01L 2225/06513
- H01L 2225/06517
- H01L 2225/06541
- H01L 2225/06548
- H01L 2225/06565
- H01L 2924/07025
- H01L 2924/15174
- H01L 2924/15311
- H01L 2924/014
- H01L 2924/00
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED 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)
- H01L

## Abstract

A photosensitive resin composition using a polyimide precursor composition, a cured film, a method for producing a cured film, a semiconductor device, and a method for producing a polyimide precursor composition are provided. In the polyimide precursor composition, the molar ratio of repeating units represented by General Formula (1-2) among structural isomers of the polyimide precursor is 60% to 90% by mole. In General Formula (1-2), A1 and A2 each independently represents an oxygen atom or NH, R111 and R112 each independently represents a single bond or a divalent organic group, and R113 and R114 each independently represents a hydrogen atom or a monovalent organic group.

## Claims

### Claim 1

A polyimide precursor composition comprising:
a polyimide precursor including repeating units represented by General Formula (1-1),
wherein the molar ratio of repeating units represented by General Formula (1-2) among the structural isomers of the polyimide precursor is 60% to 90% by mole,
in General Formulae (1-1) and (1-2), A1 and A2 each independently represents an oxygen atom or NH, R111 and R112 each independently represents a single bond or a divalent organic group, and R113 and R114 each independently represents a hydrogen atom or a monovalent organic group,
wherein the weight-average molecular weight/number-average molecular weight which is the dispersity of the polyimide precursor is 2.0 to 4.0.

### Claim 2 (depends on 1)

The polyimide precursor composition according to claim 1,
wherein at least one of R113 or R114 contains a polymerizable group.

### Claim 3 (depends on 1)

The polyimide precursor composition according to claim 1,
wherein both of R113 and R114 contain a polymerizable group.

### Claim 4 (depends on 1)

The polyimide precursor composition according to claim 1,
wherein at least one of A1 or A2 is an oxygen atom.

### Claim 5 (depends on 1)

The polyimide precursor composition according to claim 1,
wherein R112 is a single bond, or a group selected from a hydrocarbon group having 1 to 10 carbon atoms, —O—, —C(═O)—, —S—, —S(═O)2—, —NHCO—, and a combination thereof.

### Claim 6 (depends on 1)

The polyimide precursor composition according to claim 1,
wherein the weight-average molecular weight of the polyimide precursor is 1,000 to 100,000.

### Claim 7 (depends on 1)

A photosensitive resin composition comprising:
the polyimide precursor composition according to claim 1; and
a curable compound.

### Claim 8 (depends on 7)

The photosensitive resin composition according to claim 7,
wherein the curable compound includes a compound having an ethylenically unsaturated bond.

### Claim 9 (depends on 7)

The photosensitive resin composition according to claim 7,
wherein the curable compound includes a compound having two or more ethylenically unsaturated groups.

### Claim 10 (depends on 7)

The photosensitive resin composition according to claim 7,
wherein the curable compound is at least one compound selected from a compound having at least one of a hydroxymethyl group, an alkoxymethyl group, and an acyloxymethyl group, an epoxy compound, an oxetane compound, and a benzoxazine compound.

### Claim 11 (depends on 7)

The photosensitive resin composition according to claim 7, further comprising:
at least one kind of thermal base generator selected from an acidic compound which generates a base upon heating to 40° C. or higher and an ammonium salt having an anion with a pKal of 0 to 4 and an ammonium cation.

### Claim 12 (depends on 11)

The photosensitive resin composition according to claim 11,
wherein the acidic compound is a compound which generates a base upon heating to 120° C. to 200° C.

### Claim 13 (depends on 11)

The photosensitive resin composition according to claim 11,
wherein the acidic compound is an ammonium salt.

### Claim 14 (depends on 11)

The photosensitive resin composition according to claim 11,
wherein the acidic compound is a salt of an ammonium cation and a carboxylate anion.

### Claim 15 (depends on 11)

The photosensitive resin composition according to claim 11,
wherein the ammonium salt having an anion with a pKal of 0 to 4 and an ammonium cation is an acidic compound.

### Claim 16 (depends on 11)

The photosensitive resin composition according to claim 11,
wherein the anion contained in the ammonium salt is a carboxylate anion.

### Claim 17 (depends on 7)

The photosensitive resin composition according to claim 7, further comprising:
a photoradical polymerization initiator.

### Claim 18 (depends on 7)

The photosensitive resin composition according to claim 7, further comprising:
a photo-acid generator.

### Claim 19 (depends on 7)

A cured film formed by curing the photosensitive resin composition according to claim 7.

### Claim 20 (depends on 19)

A semiconductor device comprising:
the cured film according to claim 19.

### Claim 21 (depends on 7)

A method for producing a cured film, comprising:
applying the photosensitive resin composition according to claim 7 onto a substrate; and
curing the photosensitive resin composition applied onto the substrate.

### Claim 22

A method for producing a polyimide precursor composition, comprising:
reacting a compound represented by General Formula (P) with a compound represented by General Formula (Q) to produce a diester or a diamide; and
reacting the diester or the diamide with a compound represented by General Formula (R),
wherein the reaction for producing the diester or the diamide is carried out at 40° C. to 80° C. for 3 to 10 hours,
in General Formula (P), R112 represents a single bond or a divalent organic group;
HA3-R115 General Formula (Q)
in General Formula (Q), A3's each independently represent an oxygen atom or NH, and R115 represents a monovalent organic group; and
H2N—R111—NH2 General Formula (R)
in General Formula (R), R111 represents a divalent organic group,
wherein the polyimide precursor composition comprises a polyimide precursor including repeating units represented by General Formula (1-1), and
the molar ratio of repeating units represented by General Formula (1-2) among the structural isomers of the polyimide precursor is 60% to 90% by mole,
in General Formulae (1-1) and (1-2), A1 and A2 each independently represents an oxygen atom or NH, R111 and R112 each independently represents a single bond or a divalent organic group, and R113 and R114 each independently represents a hydrogen atom or a monovalent organic group.