# US 9,040,213 B2 · Positive photosensitive resin composition, photosensitive resin film prepared by using the same, and semiconductor device including the photosensitive resin film

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- Number: US 9,040,213 B2
- Document ID: US9040213B2
- Status: Granted
- Kind: B2
- Application number: 13/603,522
- Filed: 2012-09-05
- Published: 2013-06-27
- Granted: 2015-05-26
- Earliest claimed: 2011-12-23
- Assignees: Cheil Industries Inc.
- Applicants: Hyun-Yong Cho; Sang-Soo Kim; Eun-Kyung Yoon; Jong-Hwa Lee; Jun-Ho Lee; Eun-Ha Hwang; Ji-Yun Kwon; Jin-Young Lee
- Inventors: Hyun-Yong Cho; Sang-Soo Kim; Eun-Kyung Yoon; Jong-Hwa Lee; Jun-Ho Lee; Eun-Ha Hwang; Ji-Yun Kwon; Jin-Young Lee
- Web page: https://patentgrep.com/patent/US9040213B2

## CPC

- G03F 7/0233: {characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides}
- 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

Disclosed is a positive photosensitive resin composition that includes (A) an alkali soluble resin prepared by a phosphorous-containing diamine represented by the following Chemical Formula 1, (B) a photosensitive diazoquinone compound, and (C) a solvent. A photosensitive resin film prepared using the same and a semiconductor device including the photosensitive resin film are also disclosed. In Chemical Formula 1, each substituent is the same as defined in the detailed description.

## Claims

### Claim 1

A positive photosensitive resin composition, comprising
(A) an alkali soluble resin prepared using a phosphorous-containing diamine represented by the following Chemical Formula 1 and an aromatic diamine,
wherein the phosphorous-containing diamine and the aromatic diamine are mixed at a weight ratio of about 10:90 to about 70:30,
wherein the alkali soluble resin comprises a polybenzoxazole precursor including a repeating unit represented by the following Chemical Formula 4 and a repeating unit represented by the following Chemical Formula 10:
wherein in Chemical Formula 4,
X1 is a residual group derived from a phosphorous-containing diamine represented by the following Chemical Formula 1:
wherein in Chemical Formula 1,
R′ and R″ are the same or different and are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C3 to C20 cycloalkenyl, substituted or unsubstituted C3 to C20 cycloalkynyl, substituted or unsubstituted C2 to C20 heterocycloalkyl, substituted or unsubstituted C2 to C20 heterocycloalkenyl, substituted or unsubstituted C2 to C20 heterocycloalkynyl, or substituted or unsubstituted C6 to C30 aryl,
R is substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C3 to C20 cycloalkenyl, substituted or unsubstituted C3 to C20 cycloalkynyl, substituted or unsubstituted C2 to C20 heterocycloalkyl, substituted or unsubstituted C2 to C20 heterocycloalkenyl, substituted or unsubstituted C2 to C20 heterocycloalkynyl, or substituted or unsubstituted C6 to C30 aryl, and
n′ and n″ are the same or different and are each independently integers ranging from 0 to 3,
and Y1 is a substituted or unsubstituted C6 to C30 aromatic organic group, substituted or unsubstituted divalent to hexavalent C1 to C30 aliphatic organic group, or substituted or unsubstituted divalent to hexavalent C3 to C30 alicyclic organic group:
wherein in Chemical Formula 10,
X2 is a residual group derived from aromatic diamine represented by the following Chemical Formula 8, Chemical Formula 9, or a combination thereof:
wherein in Chemical Formulae 8 and 9,
A is a single bond, —O—, —CO—, —CR4R5—, —SO2—, or —S—, wherein R4 and R5 are the same or different and are each independently hydrogen or substituted or unsubstituted C1 to C30 alkyl,
R1 to R3 are the same or different and are each independently hydrogen, substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 carboxyl group, a hydroxy group, or a thiol group,
n1 is an integer ranging from 0 to 2, and
N2 and n3 are the same or different and are each independently an integer ranging from 0 to 3, and
Y2 is a substituted or unsubstituted C6 to C30 aromatic organic group, substituted or unsubstituted divalent to hexavalent C1 to C30 aliphatic organic group, or substituted or unsubstituted divalent to hexavalent C3 to C30 alicyclic organic group;
(B) a photosensitive diazoquinone compound; and
(C) a solvent.

### Claim 2 (depends on 1)

The positive photosensitive resin composition of claim 1, wherein the phosphorous-containing diamine comprises at least one compound represented by the following Chemical Formulae 2 and 3, or a combination thereof:

### Claim 3 (depends on 1)

The positive photosensitive resin composition of claim 1, wherein the positive photosensitive resin composition further comprises (A′) an alkali soluble resin prepared from aromatic diamine, wherein the aromatic diamine comprises a diamine represented by Chemical Formula 8, Chemical Formula 9, or a combination thereof:
wherein in Chemical Formulae 8 and 9,
A is a single bond, —O—, —CO—, —CR4R5—, —SO2—, or —S—, wherein R4 and R5 are the same or different and are each independently hydrogen or substituted or unsubstituted C1 to C30 alkyl,
R1 to R3 are the same or different and are each independently hydrogen, substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 carboxyl group, a hydroxy group, or a thiol group,
n1 is an integer ranging from 0 to 2, and
n2 and n3 are the same or different are and are each independently an integer ranging from 0 to 3.

### Claim 4 (depends on 3)

The positive photosensitive resin composition of claim 3, wherein the alkali soluble resin prepared from phosphorous-containing diamine (A) and the alkali soluble resin prepared from aromatic diamine (A′) are mixed at a weight ratio of about 5:95 to about 95:5.

### Claim 5 (depends on 1)

The positive photosensitive resin composition of claim 1, wherein the alkali soluble resin has a weight average molecular weight (Mw) of about 3,000 to about 300,000 g/mol.

### Claim 6 (depends on 1)

The positive photosensitive resin composition of claim 1, wherein the positive photosensitive resin composition comprises:
about 5 to about 100 parts by weight of the photosensitive diazoquinone compound (B) and
about 100 to about 900 parts by weight of the solvent (C),
based on about 100 parts by weight of the alkali soluble resin (A).

### Claim 7 (depends on 1)

A photosensitive resin film prepared using the positive photosensitive resin composition of claim 1.

### Claim 8 (depends on 7)

A semiconductor device including the photosensitive resin film according to claim 7.

### Claim 9 (depends on 1)

The positive photosensitive resin composition of claim 1, wherein the phosphorous-containing diamine and the aromatic diamine are mixed at a weight ratio of about 10:90 to about 60:40.

### Claim 10 (depends on 1)

The positive photosensitive resin composition of claim 1, wherein the phosphorous-containing diamine and the aromatic diamine are mixed at a weight ratio of about 10:90 to about 35:65.