# US 9,753,368 B2 · Photosensitive resin composition, photosensitive resin film using the same and color filter

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- Number: US 9,753,368 B2
- Document ID: US9753368B2
- Status: Granted
- Kind: B2
- Application number: 15/270,044
- Filed: 2016-09-20
- Published: 2017-04-20
- Granted: 2017-09-05
- Earliest claimed: 2015-10-14
- Assignees: Samsung SDI Co., Ltd.
- Applicants: Samsung SDI Co., Ltd.
- Inventors: Sohyun Kim; Jaeyoung Kwon; Sundae Kim; Jieun Kim; Kwangwon Seo; Seungjib Choi; Eunjeong Choi; Gyuseok Han
- Web page: https://patentgrep.com/patent/US9753368B2

## CPC

- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- C09B 11/02: derived from diarylmethanes
- C09B 55/009: {Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image)}
- G03F 7/0007: {Filters, e.g. additive colour filters; Components for display devices}
- G03F 7/0048: {characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents}
- G03F 7/031: Organic compounds not covered by group G03F7/029
- G03F 7/032: with binders
- G03F 7/033: the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
- G03F 7/105: having substances, e.g. indicators, for forming visible images
- G03F 7/16: Coating processes; Apparatus therefor (applying coatings to base materials in general B05; applying photosensitive compositions to base for photographic purposes G03C1/74)
- G03F 7/20: Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00)
- G03F 7/26: Processing photosensitive materials; Apparatus therefor (G03F7/12 - G03F7/24 take 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)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)

## Abstract

A photosensitive resin composition, a photosensitive resin film, and a color filter, the composition including a binder resin; a dye consisting of a cation and an anion; a photopolymerizable compound; a photopolymerization initiator, and a solvent, wherein the dye is included in an amount of about 15 wt % to about 40 wt % based on a total weight of a photosensitive resin composition, and wherein the cation is represented by Chemical Formula 1:

## Claims

### Claim 1

A photosensitive resin composition, comprising
a binder resin;
a dye consisting of a cation and an anion;
a photopolymerizable compound;
a photopolymerization initiator, and
a solvent,
wherein the dye is included in an amount of about 15 wt % to about 40 wt % based on a total weight of a photosensitive resin composition,
wherein the cation is represented by Chemical Formula 1:
wherein, in Chemical Formula 1,
R1 to R6 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group,
R7 is a substituted or unsubstituted C6 to C20 aryl group, and
X is —O—, —S—, or —NR8—, in which R8 is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

### Claim 2 (depends on 1)

The photosensitive resin composition as claimed in claim 1, wherein X is —O— or —S—.

### Claim 3 (depends on 1)

The photosensitive resin composition as claimed in claim 1, wherein R1 to R4 are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

### Claim 4 (depends on 1)

The photosensitive resin composition as claimed in claim 1, wherein the cation represented by Chemical Formula 1 is represented by Chemical Formula 2:
wherein, in Chemical Formula 2,
R9 and R10 are each independently a substituted or unsubstituted C1 to C20 alkyl group,
R11 and R12 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
R13 is a substituted or unsubstituted C6 to C20 aryl group,
R14 to R17 are each independently a halogen atom or a substituted or unsubstituted C1 to C 10 alkyl group,
n1 to n4 are each independently an integer of 0 to 5, such that 0≦n1+n2≦5, and 0≦n3+n4≦5, and
X is —O— or —S—.

### Claim 5 (depends on 1)

The photosensitive resin composition as claimed in claim 1, wherein the cation represented by Formula 1 is represented by one of the following Chemical Formula 3 to Chemical Formula 7:
wherein, in Chemical Formula 3,
R18, R19, and R21 are each independently a substituted or unsubstituted C1 to C20 alkyl group,
R22 is a halogen atom,
R23 to R26 are each independently a halogen atom or a substituted or unsubstituted C1 to C 10 alkyl group,
m is an integer of 0 to 2,
n5 to n8 are each independently 0 or 1, and
X is —O— or —S—,
wherein, in Chemical Formula 4,
R18 to R21 are each independently a substituted or unsubstituted C1 to C20 alkyl group,
R22 is a halogen atom,
R23 to R26 are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
m is an integer of 0 to 2,
n5 to n8 are each independently 0 or 1, and
X is —O— or —S—,
wherein, in Chemical Formula 5,
R18 and R19 are each independently a substituted or unsubstituted C1 to C20 alkyl group,
R22 is a halogen atom,
R23 to R26 are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R27 is a substituted or unsubstituted C6 to C20 aryl group,
m is an integer of 0 to 2,
n5 to n8 are each independently 0 or 1, and
X is —O— or —S—,
wherein, in Chemical Formula 6,
R18 and R19 are each independently a substituted or unsubstituted C1 to C20 alkyl group,
R22 is a halogen atom,
R23 to R26 are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R27 and R28 are each independently a substituted or unsubstituted C6 to C20 aryl group,
m is an integer of 0 to 2,
n5 to n8 are each independently 0 or 1, and
X is —O— or —S—,
wherein, in Chemical Formula 7,
R18, R19, and R21 are each independently a substituted or unsubstituted C1 to C20 alkyl group,
R22 is a halogen atom,
R23 to R26 are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R28 is a substituted or unsubstituted C6 to C20 aryl group,
m is an integer of 0 to 2,
n5 to n8 are each independently 0 or 1, and
X is —O— or —S—.

### Claim 6 (depends on 1)

The photosensitive resin composition as claimed in claim 1, wherein the cation represented by Chemical Formula 1 is represented one of the following Chemical Formula 5-3, Chemical Formula 5-4, Chemical Formula 5-5, Chemical Formula 5-6, Chemical Formula 7-6, Chemical Formula 7-8, Chemical Formula 7-10, Chemical Formula 7-12, Chemical Formula 7-14, and Chemical Formula 7-17:

### Claim 7 (depends on 1)

The photosensitive resin composition as claimed in claim 1, wherein the anion is represented by one of the following Chemical Formula A to Chemical Formula F:

### Claim 8 (depends on 1)

The photosensitive resin composition as claimed in claim 1, wherein the dye is a blue dye.

### Claim 9 (depends on 1)

The photosensitive resin composition as claimed in claim 1, wherein the dye has a maximum absorbance (λmax) in a wavelength of about 600 nm to about 700 nm.

### Claim 10 (depends on 1)

The photosensitive resin composition as claimed in claim 1, wherein the dye has a maximum transmittance (Tmax) in a wavelength of about 400 nm to about 500 nm.

### Claim 11 (depends on 1)

The photosensitive resin composition as claimed in claim 1, further comprising a pigment.

### Claim 12 (depends on 1)

The photosensitive resin composition as claimed in claim 1, wherein the binder resin has an a weight average molecular weight of about 5,000 g/mol to about 15,000 g/mol.

### Claim 13 (depends on 1)

The photosensitive resin composition as claimed in claim 1, wherein the binder resin has an acid value of about 80 mgKOH/g to about 130 mgKOH/g.

### Claim 14 (depends on 1)

The photosensitive resin composition as claimed in claim 1, wherein the binder resin includes an acryl-based binder resin, a cardo-based binder resin, or a combination thereof.

### Claim 15 (depends on 1)

The photosensitive resin composition as claimed in claim 1, wherein the photosensitive resin composition includes:
about 1 wt % to about 30 wt % of the binder resin;
the about 15 wt % to about 40 wt % of the dye;
about 1 wt % to about 15 wt % of the photopolymerizable compound;
about 0.01 wt % to about 10 wt % of the photopolymerization initiator, and
a balance amount of the solvent,
all wt % being based on the total weight of the photosensitive resin composition.

### Claim 16 (depends on 1)

The photosensitive resin composition as claimed in claim 1, further comprising an epoxy compound, malonic acid, 3-amino-1,2-propanediol, a silane-based coupling agent, a leveling agent, a surfactant, a radical polymerization initiator, or a combination thereof.

### Claim 17 (depends on 1)

A photosensitive resin film manufactured using the photosensitive resin composition as claimed in claim 1.

### Claim 18 (depends on 17)

A color filter including the photosensitive resin film as claimed in claim 17.