KR20220132959A - Photosensitive resin composition comprising the same, photosensitive resin layer, color filter and cmos image sensor - Google Patents

Abstract

The present invention relates to a photosensitive resin composition, a photosensitive resin film manufactured by using the photosensitive resin composition, a color filter including the photosensitive resin film, and a CMOS image sensor including the color filter, wherein the photosensitive resin composition comprises: (A) a binder resin; (B) a photopolymerizable monomer; (C) a photopolymerization initiator; (D) a colorant comprising pigments and dyes; and (E) a solvent, and wherein the dye is composed of a core represented by chemical formula 1 below and a shell surrounding the core and represented by chemical formula 2. [Chemical formula 1]. [Chemical formula 2]. The chemical formula 1 and chemical formula 2 are as defined in the specification.

Description

Photosensitive resin composition, photosensitive resin film, color filter and CMOS image sensor

The present disclosure relates to a photosensitive resin composition, a photosensitive resin film manufactured using the photosensitive resin composition, a color filter including the photosensitive resin film, and a CMOS image sensor including the color filter.

Recently, with the rapid development of advanced information and communication processing technology and the overall electronics industry, there is a need for a next-generation detector capable of rapidly transmitting and receiving a large amount of information, and the development of a new concept element and system is required. In particular, with the rise of video processing in portable terminals, the technology of ultra-miniaturized and ultra-power-saving image sensors is rapidly developing centered on the existing CCD (Charge Coupled Device) and CMOS (Complementary Metal Oxide Semiconductor) trend. to be.

The image sensor is a semiconductor that converts photons into electrons and displays them on a display or stores them in a storage device. It consists of an ASIC part that converts signals to digital and processes image signals, and there are CCD, CMOS, and CIS (Contact Image Sensor) types.

CCD and CMOS image sensors use the same light-receiving element. In the case of CCD image sensors, the charges generated from the light-receiving part move sequentially through the MOS capacitors connected in series, and are converted into voltages in the source follower connected to the final stage. On the other hand, in the CMOS image sensor, the charge is converted into a voltage in the source follower built into each pixel and output to the outside. To be more specific, a CCD image sensor moves electrons generated by light to the output unit using a gate pulse as it is, and converts electrons generated by light into voltage within each pixel and outputs them through various CMOS switches. It is a CMOS image sensor. The field of application of these image sensors is very wide, from household products such as digital cameras and mobile phones to endoscopes used in hospitals and telescopes of artificial satellites orbiting the earth.

As the technology trend related to CMOS image sensor, the number of pixels is increasing and the size is decreasing for realization of high quality and miniaturization of devices. do. However, compared to pigments, dyes have a problem in terms of fairness when manufacturing patterns. In particular, there is a problem in terms of chemical resistance. The reason is that the pigment is fine particles and has poor solubility due to crystallinity, so it cannot be eluted in a solvent such as PGMEA after baking. Because it has the disadvantage of melting. In particular, in the case of a CMOS image sensor, it is difficult to improve the chemical resistance of the dye because the content of the color material is high and the ratio of the binder resin or monomer used together is relatively low.

One embodiment is to provide a photosensitive resin composition comprising a core-shell compound as a dye, constituting a green pixel in a color filter for a CMOS image sensor, and further comprising a pigment.

Another embodiment is to provide a photosensitive resin film prepared using the photosensitive resin composition.

Another embodiment is to provide a color filter including the photosensitive resin film.

Another embodiment is to provide a CMOS image sensor including the color filter.

One embodiment of the present invention is (A) a binder resin; (B) a photopolymerizable monomer; (C) a photoinitiator; (D) colorants including pigments and dyes; and (E) a solvent, wherein the dye includes a core represented by the following formula (1) and a shell represented by the following formula (2), which surrounds the core, and provides a photosensitive resin composition.

[Formula 1]

[Formula 2]

In Formula 1 and Formula 2,

R ¹ to R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group, wherein R ¹ to R ⁸ are not hydrogen atoms at the same time,

R ¹ and R ² may be fused to each other to form a ring, or R ³ and R ⁴ may be fused to each other to form a ring,

At least one of R ¹ , R ² , R ⁵ and R ⁶ includes a siloxane group at the terminal,

At least one of R ³ , R ⁴ , R ⁷ and R ⁸ includes a siloxane group at the terminal,

L ^a and L ^b are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group,

n1, n2, n3 and n4 are each independently an integer of 0 or 1, n1+n2 ≠ 0, n3+n4 ≠ 0,

n is an integer greater than or equal to 2;

The substituent including a siloxane group at the terminal may include an ether linking group (*-O-*).

At least one of R ¹ , R ² , R ⁵ , and R ⁶ , and at least one or more of R ³ , R ⁴ , R ⁷ , and R ⁸ may each be represented by Formula 3 below.

[Formula 3]

In Formula 3,

R ⁹ to R ¹¹ are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C1 to C20 alkoxy group,

L ¹ is a substituted or unsubstituted C1 to C20 alkylene group.

Any one of R ¹ , R ² , R ⁵ and R ⁶ and any one of R ³ , R ⁴ , R ⁷ and R ⁸ may each independently include a siloxane group at the terminal thereof. In this case, Formula 1 may be represented by Formula 1-1 or Formula 1-2.

[Formula 1-1]

In Formula 1-1,

R ¹ to R ⁴ , R ⁶ and R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group, wherein R ¹ to R ⁴ , R ⁶ and R ⁸ is not a hydrogen atom at the same time,

R ¹ and R ² may be fused to each other to form a ring, or R ³ and R ⁴ may be fused to each other to form a ring,

R ¹ To R ⁴ , R ⁶ And R ⁸ All do not include a siloxane group,

R ⁵ and R ⁷ are each independently a C1 to C20 alkyl group including a siloxane group at the terminal or a C1 to C20 alkoxy group including a siloxane group at the terminal,

n5 and n6 are each independently an integer of 0 or 1.

[Formula 1-2]

In Formula 1-2,

R ² , R ⁴ , R ⁶ and R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group, wherein R ² , R ⁴ , R ⁶ and R ⁸ is not a hydrogen atom at the same time,

R ² , R ⁴ , R ⁶ and R ⁸ all do not contain a siloxane group,

R ¹ and R ³ are each independently a C1 to C20 alkyl group including a siloxane group at the terminal or a C1 to C20 alkoxy group including a siloxane group at the terminal,

n5 and n6 are each independently an integer of 0 or 1.

Any two of R ¹ , R ² , R ⁵ and R ⁶ and any two of R ³ , R ⁴ , R ⁷ and R ⁸ may each independently include a siloxane group at the terminal thereof. In this case, Chemical Formula 1 may be represented by Chemical Formula 1-3 below.

[Formula 1-3]

In Formula 2-3,

R ² , R ⁴ , R ⁶ and R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group, wherein R ² , R ⁴ , R ⁶ and R ⁸ is not a hydrogen atom at the same time,

R ² , R ⁴ , R ⁶ and R ⁸ all do not contain a siloxane group,

R ¹ , R ³ , R ⁵ and R ⁷ are each independently a C1 to C20 alkyl group including a siloxane group at the terminal or a C1 to C20 alkoxy group including a siloxane group at the terminal,

n5 and n6 are each independently an integer of 0 or 1.

Any three of R ¹ , R ² , R ⁵ and R ⁶ and any three of R ³ , R ⁴ , R ⁷ and R ⁸ may each independently include a siloxane group at the terminal thereof. In this case, Chemical Formula 1 may be represented by Chemical Formula 1-4 below.

[Formula 1-4]

In Formula 1-4,

R ⁶ and R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group,

R ⁶ and R ⁸ both do not contain a siloxane group,

R ¹ to R ⁵ and R ⁷ are each independently a C1 to C20 alkyl group including a siloxane group at the terminal or a C1 to C20 alkoxy group including a siloxane group at the terminal,

n5 and n6 are each independently an integer of 0 or 1.

The core represented by Formula 1 may have a maximum absorption wavelength in the range of 610 nm to 640 nm.

The shell represented by Formula 2 may be represented by Formula 2-1 below.

[Formula 2-1]

The dye may be represented by any one of the following Chemical Formulas A to K.

[Formula A]

[Formula B]

[Formula C]

[Formula D]

[Formula E]

[Formula F]

[Formula G]

[Formula H]

[Formula I]

[Formula J]

[Formula K]

The dye may be a green dye.

The photosensitive resin composition may be for a CMOS image sensor.

Another embodiment provides a photosensitive resin film including the photosensitive resin composition.

Another embodiment provides a color filter including the photosensitive resin film.

Another embodiment provides a CMOS image sensor including the color filter.

The specific details of other aspects of the invention are included in the detailed description below.

The core-shell compound according to an embodiment has excellent chemical resistance by itself, and can maintain excellent chemical resistance even after curing and thermal processes. A green color filter for the image sensor can be provided.

Hereinafter, embodiments of the present invention will be described in detail. However, this is provided as an example, and the present invention is not limited thereto, and the present invention is only defined by the scope of the claims to be described later.

Unless otherwise specified herein, "substituted" to "substituted" means that at least one hydrogen atom in the functional group of the present invention is a halogen atom (F, Br, Cl or I), a hydroxyl group, a nitro group, a cyano group, an amino group ( NH ₂ , NH(R ²⁰⁰ ) or N(R ²⁰¹ )(R ²⁰² ), wherein R ²⁰⁰ , R ²⁰¹ and R ²⁰² are the same or different from each other, and each independently a C1 to C10 alkyl group), an amidino group, A hydrazine group, a hydrazone group, a carboxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic organic group, a substituted or unsubstituted aryl group, and It means substituted with one or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group.

Unless otherwise specified herein, "alkyl group" means a C1 to C20 alkyl group, specifically means a C1 to C15 alkyl group, and "cycloalkyl group" means a C3 to C20 cycloalkyl group, specifically C3 to C18 cycloalkyl group, "alkoxy group" means a C1 to C20 alkoxy group, specifically means a C1 to C18 alkoxy group, "aryl group" means a C6 to C20 aryl group, specifically C6 to refers to a C18 aryl group, “alkenyl group” refers to a C2 to C20 alkenyl group, specifically refers to a C2 to C18 alkenyl group, and “alkylene group” refers to a C1 to C20 alkylene group, specifically C1 to C18 alkylene group, and “arylene group” means C6 to C20 arylene group, specifically, C6 to C16 arylene group.

Unless otherwise specified herein, "(meth)acrylate" means that both "acrylate" and "methacrylate" are possible, and "(meth)acrylic acid" is "acrylic acid" and "methacrylic acid" It means both are possible.

Unless otherwise defined herein, "combination" means mixing or copolymerization. Also, "copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymerization or random copolymerization.

In the present specification, the siloxane group refers to any functional group including a Si-O bond, for example, *-Si(OCH ₃ ) ₃ , *-Si(OCH ₃ ) ₂ CH ₃ , *-Si(OCH ₃ )(CH ₃ ) ₂ and the like are all included in the siloxane group as used herein.

Unless otherwise defined in the chemical formulas in the present specification, when a chemical bond is not drawn at a position where a chemical bond is to be drawn, it means that a hydrogen atom is bonded to the position.

In addition, unless otherwise defined in the present specification, "*" means a moiety connected to the same or different atoms or chemical formulas.

One embodiment is (A) a binder resin; (B) a photopolymerizable monomer; (C) a photoinitiator; (D) colorants including pigments and dyes; and (E) a solvent, wherein the dye includes a core represented by the following formula (1) and a shell represented by the following formula (2), which surrounds the core, and provides a photosensitive resin composition.

[Formula 1]

[Formula 2]

In Formula 1 and Formula 2,

R ¹ to R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group, wherein R ¹ to R ⁸ are not hydrogen atoms at the same time,

R ¹ and R ² may be fused to each other to form a ring, or R ³ and R ⁴ may be fused to each other to form a ring,

At least one of R ¹ , R ² , R ⁵ and R ⁶ includes a siloxane group at the terminal,

At least one of R ³ , R ⁴ , R ⁷ and R ⁸ includes a siloxane group at the terminal,

L ^a and L ^b are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group,

n1, n2, n3 and n4 are each independently an integer of 0 or 1, n1+n2 ≠ 0, n3+n4 ≠ 0,

n is an integer greater than or equal to 2;

coloring agent

In a color filter made of a pigment-type photosensitive resin composition, there is a problem of color mixing and thinning of the color filter caused by the size of the pigment particle. In addition, in the case of a color imaging device for an image sensor, a smaller dispersed particle size is required to form a fine pattern. In order to meet this demand, efforts to increase resolution by introducing a non-particle dye instead of a pigment to prepare a photosensitive resin composition suitable for the dye have been ongoing for a long time.

The photosensitive resin composition according to an exemplary embodiment includes a green dye and a pigment that enter a color filter for a CMOS image sensor. As the size of pixels decreases, there is a limit to the manufacture of fine patterns using pigments, and the development of dyes is required to compensate for this. Dyes have a problem in terms of fairness in pattern manufacturing compared to pigments, and are particularly inferior in chemical resistance. After curing and thermal processing, it was very difficult to form a fine pattern. In addition, when only a small amount of the dye, which is a colorant, is included relative to the total amount of the composition, even if the dye itself is slightly inferior in chemical resistance, it is not a big problem. 15% by weight to 30% by weight, such as about 20% to 30% by weight), the need to develop a dye having excellent chemical resistance itself is a very large situation.

The inventors of the present invention, after undergoing numerous trials and errors, introduced a siloxane group to the squarylium-based compound constituting the core under specific conditions, and surrounded the core with a shell to synthesize a single core-shell compound, as described above. The core-shell compound according to one embodiment of the present invention has excellent chemical resistance by itself, and the photosensitive resin composition containing it in excess as a green dye together with a pigment does not show significant deterioration in chemical resistance even after curing and thermal processing, CMOS It is very suitable for use in green color filters for image sensors.

For example, the substituent including a siloxane group at the terminal may include an ether linking group (*-O-*).

For example, at least one of R ¹ , R ² , R ⁵ and R ⁶ and at least one of R ³ , R ⁴ , R ⁷ , and R ⁸ may each independently be represented by Formula 3 below.

[Formula 3]

In Formula 3,

R ⁹ to R ¹¹ are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C1 to C20 alkoxy group,

L ¹ is a substituted or unsubstituted C1 to C20 alkylene group.

For example, any one of R ¹ , R ² , R ⁵ and R ⁶ and any one of R ³ , R ⁴ , R ⁷ and R ⁸ may each independently include a siloxane group at the terminal thereof. That is, the core represented by Formula 1 may include two siloxane groups. In this case, the core represented by Formula 1 may be represented by Formula 1-1 or Formula 1-2, but is not limited thereto.

[Formula 1-1]

In Formula 1-1,

R ¹ to R ⁴ , R ⁶ and R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group, wherein R ¹ to R ⁴ , R ⁶ and R ⁸ is not a hydrogen atom at the same time,

R ¹ and R ² may be fused to each other to form a ring, or R ³ and R ⁴ may be fused to each other to form a ring,

R ¹ To R ⁴ , R ⁶ And R ⁸ All do not include a siloxane group,

R ⁵ and R ⁷ are each independently a C1 to C20 alkyl group including a siloxane group at the terminal or a C1 to C20 alkoxy group including a siloxane group at the terminal,

n5 and n6 are each independently an integer of 0 or 1.

[Formula 1-2]

In Formula 1-2,

R ² , R ⁴ , R ⁶ and R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group, wherein R ² , R ⁴ , R ⁶ and R ⁸ is not a hydrogen atom at the same time,

R ² , R ⁴ , R ⁶ and R ⁸ all do not contain a siloxane group,

R ¹ and R ³ are each independently a C1 to C20 alkyl group including a siloxane group at the terminal or a C1 to C20 alkoxy group including a siloxane group at the terminal,

n5 and n6 are each independently an integer of 0 or 1.

For example, any two of R ¹ , R ² , R ⁵ and R ⁶ and any two of R ³ , R ⁴ , R ⁷ and R ⁸ may each independently include a siloxane group at the terminal thereof. That is, the core represented by Formula 1 may include four siloxane groups. In this case, the core represented by Formula 1 may be represented by Formula 1-3 below, but is not necessarily limited thereto.

[Formula 1-3]

In Formula 2-3,

R ² , R ⁴ , R ⁶ and R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group, wherein R ² , R ⁴ , R ⁶ and R ⁸ is not a hydrogen atom at the same time,

R ² , R ⁴ , R ⁶ and R ⁸ all do not contain a siloxane group,

R ¹ , R ³ , R ⁵ and R ⁷ are each independently a C1 to C20 alkyl group including a siloxane group at the terminal or a C1 to C20 alkoxy group including a siloxane group at the terminal,

n5 and n6 are each independently an integer of 0 or 1.

For example, any three of R ¹ , R ² , R ⁵ , and R ⁶ and any three of R ³ , R ⁴ , R ⁷ and R ⁸ may each independently include a siloxane group at the terminal thereof. That is, the core represented by Formula 1 may include six siloxane groups. In this case, the core represented by Formula 1 may be represented by Formula 1-4 below, but is not necessarily limited thereto.

[Formula 1-4]

In Formula 1-4,

R ⁶ and R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group,

R ⁶ and R ⁸ both do not contain a siloxane group,

R ¹ to R ⁵ and R ⁷ are each independently a C1 to C20 alkyl group including a siloxane group at the terminal or a C1 to C20 alkoxy group including a siloxane group at the terminal,

n5 and n6 are each independently an integer of 0 or 1.

The core represented by Formula 1 may include 2, 4, or 6 siloxane groups. The core represented by Chemical Formula 1 having one, three, or five siloxane groups is difficult to synthesize (low yield) due to its structure, and even if it is actually synthesized successfully, it is expensive when applied to an actual line, so it is economical. Not desirable.

In addition, the core represented by Formula 1 is superior in chemical resistance in terms of chemical resistance when the number of siloxane groups is 6 compared to when the number of siloxane groups is 4, and is superior in chemical resistance than when the number of siloxane groups is 2 . That is, if only the chemical resistance aspect of the compound is considered, the number of siloxane groups in the core structure represented by Formula 1 is preferably 4 rather than 2, and 6 rather than 4.

On the other hand, in the core represented by Formula 1, when the number of siloxane groups is 2, it is superior in terms of compound solubility than when the number of siloxane groups is 4, and when the number of siloxane groups is 4, when the number of siloxane groups is 6, it is superior in terms of solubility of the compound. great. That is, if only the solubility aspect of the compound is considered, the number of siloxane groups in the core structure represented by Chemical Formula 1 is preferably 4 rather than 6, and preferably 2 rather than 4.

On the other hand, in the core represented by Formula 1, when the number of the siloxane groups is one, synthesis is difficult as described above, and the chemical resistance is rather lower than when the number of the siloxane groups is two, so represented by Formula 1 It is preferred that the core to be formed contains two or more siloxane groups.

That is, the core represented by Formula 1 may most preferably have four siloxane groups in consideration of both chemical resistance and solubility of the compound.

For example, the core represented by Formula 1 may have a maximum absorption wavelength in the range of 610 nm to 640 nm. Even if the dye compound has excellent solubility in organic solvents of 10% or more, if it does not have the maximum absorption wavelength at 610 nm to 640 nm, the transmittance is low, so it may be unsuitable for use as a green photosensitive resin composition for CMOS image sensors. .

The shell represented by Formula 2 may be represented by Formula 2-1 below.

[Formula 2-1]

For example, the dye may be represented by any one of the following Chemical Formulas A to K, but is not necessarily limited thereto.

[Formula A]

[Formula B]

[Formula C]

[Formula D]

[Formula E]

[Formula F]

[Formula G]

[Formula H]

[Formula I]

[Formula J]

[Formula K]

For example, the dye may be a green dye.

According to another embodiment, there is provided a photosensitive resin composition comprising the dye according to the embodiment.

For example, the photosensitive resin composition may have a transmittance of 90% or more at 540 nm, a transmittance of 10% or less at 600 nm to 640 nm, and a transmittance of 5% or less at 450 nm, a green color for high transmission type CIS It may be suitable for filter implementation. That is, the photosensitive resin composition may be for a high-transmission CMOS image sensor.

The photosensitive resin composition may further include the core-shell compound, a binder resin, a photopolymerizable monomer, a photoinitiator, and a solvent.

The dye according to an embodiment may be included in an amount of 15 wt% to 30 wt%, for example 20 wt% to 30 wt%, based on the total amount of the photosensitive resin composition. When the dye according to an embodiment is included in the above range, color gamut and contrast ratio may be excellent, and application to a CMOS image sensor may be possible .

The photosensitive resin composition further includes a pigment, such as a yellow pigment, a green pigment, or a combination thereof.

The yellow pigment has C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150 etc. are mentioned, These can be used individually or in mixture of 2 or more types.

The green pigment has C.I. Pigment Green 36, C.I. Pigment Green 58, C.I. Pigment Green 59 etc. are mentioned, These can be used individually or in mixture of 2 or more types.

The pigment may be included in the photosensitive resin composition in the form of a pigment dispersion.

The pigment dispersion may include a solid pigment, a solvent, and a dispersing agent for uniformly dispersing the pigment in the solvent.

The solid content of the pigment is 1% to 20% by weight, such as 8% to 20% by weight, such as 8% to 15% by weight, such as 10% to 20% by weight, such as 10% to 20% by weight, based on the total amount of the pigment dispersion. It may be included in 15% by weight.

As the dispersant, a nonionic dispersant, an anionic dispersant, a cationic dispersant, and the like may be used. Specific examples of the dispersant include polyalkylene glycol and its esters, polyoxyalkylene, polyalcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylic acid salts, alkylamide alkylene oxide adducts, alkyl amines, and the like, and these may be used alone or in combination of two or more.

Examples of commercially available products of the dispersant include BYK's DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165, DISPERBYK -166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001, etc.; EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, EFKA-450, etc. from EFKA Chemicals; Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse24000GR, Solsperse 27000, Solsperse 28000, etc. from Zeneka; or Ajinomoto's PB711 and PB821.

The dispersant may be included in an amount of 1 wt% to 20 wt% based on the total amount of the pigment dispersion. When the dispersing agent is included within the above range, it is possible to maintain an appropriate viscosity and thus the photosensitive resin composition has excellent dispersibility, thereby maintaining optical, physical and chemical quality during product application.

As a solvent for forming the pigment dispersion, ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, etc. may be used.

The pigment dispersion may be included in an amount of 15 wt% to 60 wt%, for example 30 wt% to 50 wt%, based on the total amount of the photosensitive resin composition. When the pigment dispersion is included within the above range, it is advantageous to secure a process margin, and the color reproducibility and contrast ratio are excellent.

binder resin

The binder resin may be an acrylic binder resin.

The acrylic binder resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin including one or more acrylic repeating units.

The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.

The first ethylenically unsaturated monomer may be included in an amount of 5 wt% to 50 wt%, for example 10 wt% to 40 wt%, based on the total amount of the acrylic binder resin.

The second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene, α-methylstyrene, vinyltoluene or vinylbenzylmethyl ether; Methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, unsaturated carboxylic acid ester compounds such as cyclohexyl (meth) acrylate and phenyl (meth) acrylate; unsaturated carboxylic acid amino alkyl ester compounds such as 2-aminoethyl (meth)acrylate and 2-dimethylaminoethyl (meth)acrylate; Carboxylic acid vinyl ester compounds, such as vinyl acetate and a vinyl benzoate; unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth)acrylate; Vinyl cyanide compounds, such as (meth)acrylonitrile; unsaturated amide compounds such as (meth)acrylamide; and the like, and these may be used alone or in combination of two or more.

Specific examples of the acrylic binder resin include (meth)acrylic acid/benzyl methacrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene copolymer, (meth)acrylic acid/benzyl methacrylate/2-hydroxyethyl meth A acrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymer, etc. may be mentioned, but are not limited thereto, and these may be used alone or in combination of two or more. have.

The weight average molecular weight of the binder resin may be 3,000 g/mol to 150,000 g/mol, such as 5,000 g/mol to 50,000 g/mol, such as 20,000 g/mol to 30,000 g/mol. When the weight average molecular weight of the binder resin is within the above range, the photosensitive resin composition has excellent physical and chemical properties, has an appropriate viscosity, and has excellent adhesion to a substrate when manufacturing a color filter.

The acid value of the binder resin may be 15 mgKOH/g to 60 mgKOH/g, for example, 20 mgKOH/g to 50 mgKOH/g 　. When the acid value of the binder resin is within the above range, the resolution of the pixel pattern is excellent.

The binder resin may be included in an amount of 1 wt% to 30 wt%, for example, 1 wt% to 20 wt%, based on the total amount of the photosensitive resin composition. When the binder resin is included within the above range, excellent developability and improved crosslinking properties can be obtained during the manufacture of a color filter, thereby obtaining excellent surface smoothness.

photopolymerizable monomer

The photopolymerizable monomer may be a monofunctional or polyfunctional ester of (meth)acrylic acid having at least one ethylenically unsaturated double bond.

Since the photopolymerizable monomer has the ethylenically unsaturated double bond, it is possible to form a pattern excellent in heat resistance, light resistance and chemical resistance by causing sufficient polymerization during exposure to light in the pattern forming process.

Specific examples of the photopolymerizable monomer include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, neopentyl glycol Di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A di(meth)acrylate, pentaerythritol di(meth)acrylate , pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (meth) acrylate, dipentaerythritol di (meth) acrylate, dipentaerythritol tri (meth) Acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol monomethyl ether (meth) acrylate, trimethylol propane tri ( and meth)acrylate, tris(meth)acryloyloxyethyl phosphate, and novolac epoxy (meth)acrylate.

Examples of commercially available products of the photopolymerizable monomer are as follows. Examples of the monofunctional ester of (meth)acrylic acid include Aronix M-101 ^® , M-111 ^® , M-114 ^® by Toagosei Chemical Co., Ltd.; Nihon Kayaku Co., Ltd.'s KAYARAD TC-110S ^® , Copper TC-120S ^® , etc.; V-158 ^® and V-2311 ^® of Osaka Yuki Chemical High School Co., Ltd. are mentioned. Examples of the bifunctional ester of (meth)acrylic acid, Toagosei Chemical Co., Ltd. Aronix M-210 ^® , copper M-240 ^® , copper M-6200 ^® and the like; Nihon Kayaku Co., Ltd.'s KAYARAD HDDA ^® , Copper HX-220 ^® , Copper R-604 ^® , etc.; and V-260 ^® , V-312 ^® , V-335 HP ^® of Osaka Yuki Chemical High School Co., Ltd. and the like. Examples of the trifunctional ester of (meth)acrylic acid, Toagosei Chemical Co., Ltd. Aronix M-309 ^® , copper M-400 ^® , copper M-405 ^® , copper M-450 ^® , copper M -710 ^® , copper M-8030 ^® , copper M-8060 ^® etc; Nihon Kayaku Co., Ltd.'s KAYARAD TMPTA ^® , Copper DPCA-20 ^® , Copper-30 ^® , Copper-60 ^® , Copper-120 ^® etc.; V-295 ^® , Dong-300 ^® , Dong-360 ^® , Dong-GPT ^{® , Dong-3PA ® ,} Dong-400 ^® etc. from Osaka Yuki Kayaku High School Co., Ltd. are mentioned. These products may be used alone or in combination of two or more.

The photopolymerizable monomer may be used by treating it with an acid anhydride in order to provide better developability.

The photopolymerizable monomer may be included in an amount of 1 wt% to 15 wt%, for example 1 wt% to 10 wt%, based on the total amount of the photosensitive resin composition. When the photopolymerizable monomer is included within the above range, curing occurs sufficiently during exposure in the pattern forming process, thereby providing excellent reliability and excellent developability in an alkaline developer.

photopolymerization initiator

The photopolymerization initiator is an initiator generally used in the photosensitive resin composition, for example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, an oxime-based compound, or a combination thereof can be used

Examples of the acetophenone-based compound include 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, p-t-butyltrichloroacetophenone, p-t -Butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholino propane-1 -one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, etc. are mentioned.

Examples of the benzophenone-based compound include benzophenone, benzoylbenzoic acid, methylbenzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4 '-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, etc. are mentioned.

Examples of the thioxanthone-based compound include thioxanthone, 2-methylthioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2- Chlorothioxanthone etc. are mentioned.

Examples of the benzoin-based compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyldimethyl ketal.

Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis(trichloromethyl)-s-triazine, 2-(3', 4'- Dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-biphenyl 4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphtho-1-yl)-4, 6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-bis (trichloromethyl)-6-piperonyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine, etc. are mentioned.

Examples of the oxime-based compound include an O-acyloxime-based compound, 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, and 1-(o-acetyloxime). )-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, O-ethoxycarbonyl-α-oxyamino-1-phenylpropan-1-one etc. can be used. Specific examples of the O-acyloxime compound include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butane- 1-one, 1-(4-phenylsulfanylphenyl)-butane-1,2-dione2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione2 -oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1-oneoxime-O-acetate and 1-(4-phenylsulfanylphenyl)-butan-1-oneoxime-O- Acetate etc. are mentioned.

As the photopolymerization initiator, a carbazole-based compound, a diketone-based compound, a sulfonium borate-based compound, a diazo-based compound, an imidazole-based compound, a biimidazole-based compound, or a fluorene-based compound may be used in addition to the above compound.

The photopolymerization initiator may be used together with a photosensitizer that causes a chemical reaction by absorbing light to enter an excited state and then transferring the energy.

Examples of the photosensitizer include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate, and the like. can be heard

The photopolymerization initiator may be included in an amount of 0.01 wt% to 10 wt%, for example, 0.1 wt% to 5 wt%, based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is included within the above range, curing occurs sufficiently during exposure in the pattern forming process to obtain excellent reliability, and the pattern has excellent heat resistance, light resistance and chemical resistance, and also has excellent resolution and adhesion. A decrease in transmittance can be prevented.

menstruum

As the solvent, materials having compatibility with the dye, pigment, binder resin, photopolymerizable monomer, and photoinitiator, but not reacting may be used.

Examples of the solvent include alcohols such as methanol and ethanol; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, and tetrahydrofuran; glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; carbitols such as methylethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and diethylene glycol diethyl ether; propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate; aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, and 2-heptanone ; saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, -n-butyl acetate, and isobutyl acetate; lactic acid esters such as methyl lactate and ethyl lactate; oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate, and butyl oxyacetate; Alkoxy acetate alkyl esters, such as methoxy methyl acetate, methoxy ethyl acetate, methoxy butyl acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-oxypropionic acid alkyl esters, such as 3-oxy methyl propionate and 3-oxy ethyl propionate; 3-alkoxy propionic acid alkyl esters, such as 3-methoxy methyl propionate, 3-methoxy ethyl propionate, 3-ethoxy ethyl propionate, and 3-ethoxy methyl propionate; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate, and propyl 2-oxypropionate; 2-alkoxy propionic acid alkyl esters, such as 2-methoxy methyl propionate, 2-methoxy ethyl propionate, 2-ethoxy ethyl propionate, and 2-ethoxy methyl propionate; 2-oxy-2-methyl propionic acid esters such as 2-oxy-2-methyl methyl propionate and 2-oxy-2-methyl ethyl propionate, 2-methoxy-2-methyl methyl propionate, and 2-ethoxy-2- monooxy monocarboxylic acid alkyl esters of 2-alkoxy-2-methyl propionate alkyls such as ethyl methyl propionate; esters such as 2-hydroxyethyl propionate, 2-hydroxy-2-methyl ethyl propionate, ethyl hydroxyacetate, and 2-hydroxy-3-methyl methyl butanoate; Ketonic acid esters such as ethyl pyruvate, and the like, and N-methylformamide, N,N-dimethylformamide, N-methylformanilad, N-methylacetamide, and N,N-dimethylacetamide. , N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, benzoic acid and high boiling point solvents such as ethyl, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.

Of these, preferably, in consideration of compatibility and reactivity, glycol ethers such as ethylene glycol monoethyl ether; ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; esters such as ethyl 2-hydroxypropionate; carbitols such as diethylene glycol monomethyl ether; propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate; and/or ketones such as cyclohexanone may be used.

The solvent may be included in a balance, for example, 10 wt% to 50 wt%, such as 10 wt% to 40 wt%, based on the total amount of the photosensitive resin composition. When the solvent is included within the above range, since the photosensitive resin composition has an appropriate viscosity, processability in manufacturing the color filter is excellent.

other additives

The photosensitive resin composition according to an exemplary embodiment may further include an epoxy compound to improve adhesion with a substrate and the like.

Examples of the epoxy compound include a phenol novolac epoxy compound, a tetramethyl biphenyl epoxy compound, a bisphenol A-type epoxy compound, an alicyclic epoxy compound, or a combination thereof.

The epoxy compound may be included in an amount of 0.01 parts by weight to 20 parts by weight, for example, 0.1 parts by weight to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the epoxy compound is included within the above range, adhesion and storage properties are excellent.

In addition, the photosensitive resin composition may further include a silane coupling agent having a reactive substituent such as a carboxyl group, a methacryloyl group, an isocyanate group, and an epoxy group in order to improve adhesion to the substrate.

Examples of the silane coupling agent include trimethoxysilyl benzoic acid, γ methacryl oxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, γ isocyanate propyl triethoxysilane, γ glycidoxy propyl tri Methoxysilane, β-epoxycyclohexyl)ethyltrimethoxysilane, etc. are mentioned, and these can be used individually or in mixture of 2 or more types.

The silane coupling agent may be included in an amount of 0.01 parts by weight to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the silane coupling agent is included within the above range, adhesion and storage properties are excellent.

In addition, the photosensitive resin composition may further include a surfactant to improve coating properties and prevent the formation of defects, if necessary.

Examples of the surfactant include BM-1000 ^® , BM-1100 ^® and the like by BM Chemie; Dai Nippon Inky Chemical Co., Ltd.'s Mecha Pack F 142D ^® , F 172 ^® , F 173 ^® , F 183 ^® and the like; Sumitomo 3M Co., Ltd.'s Prorad FC-135 ^® , copper FC-170C ^® , copper FC-430 ^® , copper FC-431 ^® , etc.; Asahi Grass Co., Ltd.'s Saffron S-112 ^® , Copper S-113 ^® , S-131 ^® , S-141 ^® , S-145 ^® and the like; Toray Silicone Co., Ltd. SH-28PA ^® , Copper-190 ^® , Copper-193 ^® , SZ-6032 ^® , SF-8428 ^® and other commercially available fluorine-based surfactants can be used.

The surfactant may be used in an amount of 0.001 parts by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is included within the above range, coating uniformity is secured, staining does not occur, and wettability to a glass substrate is excellent.

In addition, a certain amount of other additives such as antioxidants and stabilizers may be added to the photosensitive resin composition within a range that does not impair physical properties.

According to another embodiment, there is provided a photosensitive resin film prepared by using the photosensitive resin composition according to the embodiment.

According to another embodiment, there is provided a color filter including the photosensitive resin film.

The pattern forming process in the color filter is as follows.

applying the photosensitive resin composition onto a support substrate by spin coating, slit coating, inkjet printing, or the like; drying the applied photosensitive resin composition to form a photosensitive resin composition film; exposing the photosensitive resin composition film; developing the exposed photosensitive resin composition film with an aqueous alkali solution to prepare a photosensitive resin film; and heat-treating the photosensitive resin film. Since the process conditions and the like are well known in the art, detailed descriptions thereof will be omitted herein.

Another embodiment provides a CMOS image sensor including the color filter.

Hereinafter, the present invention will be described in more detail by way of examples, but the following examples are only preferred examples of the present invention, and the present invention is not limited to the following examples.

(synthesis of compounds)

(Synthesis Example 1: Synthesis of the compound represented by Intermediate 1-1)

[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-hexyl)-phenyl-amine (100 mmol) and 3,4-Dihydroxy-cyclobut-3-ene-1,2-dione ( 50 mmol) was added to toluene (300 mL) and butanol (300 mL) and refluxed, and the resulting water was removed by a Dean-stark distillation apparatus. After stirring for 12 hours, the reaction product was distilled under reduced pressure and purified by column chromatography to obtain the compound represented by Intermediate 1-1.

(Synthesis Example 2: Synthesis of the compound represented by Intermediate 1-2)

After dissolving the compound represented by Intermediate 1-1 (5 mmol) in 600 mL of chloroform solvent, Pyridine-2,6-dicarbonyl dichloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL of chloroform, and 5 at room temperature Simultaneously drip over time. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain the compound represented by Intermediate 1-2.

(Synthesis Example 3: Synthesis of the compound represented by Intermediate 1-3)

After dissolving the compound represented by Intermediate 1-2 (5 mmol) in 50 mL of tetrahydrofuran solvent, tetrabutylammonium fluoride (11 mmol) is added at room temperature. After 30 minutes, it was separated by column chromatography to obtain the compound represented by Intermediate 1-3.

Synthesis Example 4: Synthesis of a compound represented by Formula A

The compound represented by Intermediate 1-3 (5 mmol) and sodium hydride (15 mmol) were reacted for 1 hour in 25 mL of N,N-dimethylformamide solvent, and then (3-Iodopropyl)trimethoxysilane (15 mmol) was added and heated to 50 °C. warm up After 8 hours, it is separated by column chromatography to obtain a compound represented by the following formula (A).

[Formula A]

Maldi-tof MS: 1503.9 m/z

(Synthesis Example 5: Synthesis of the compound represented by Intermediate 2-1)

[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-2 instead of [4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-hexyl)-phenyl-amine -propoxy-ethyl)-phenyl-amine was synthesized in the same manner as in Synthesis Example 1, except that the compound represented by Intermediate 2-1 was obtained

(Synthesis Example 6: Synthesis of the compound represented by Intermediate 2-2)

The compound represented by Intermediate 2-2 was obtained by synthesizing in the same manner as in Synthesis Example 2, except that the compound represented by Intermediate 2-1 was used instead of the compound represented by Intermediate 1-1.

(Synthesis Example 7: Synthesis of the compound represented by Intermediate 2-3)

The compound represented by Intermediate 2-3 was obtained by synthesizing in the same manner as in Synthesis Example 3, except that the compound represented by Intermediate 2-2 was used instead of the compound represented by Intermediate 1-2.

Synthesis Example 8: Synthesis of the compound represented by Formula B

The compound represented by the following formula (B) was obtained by synthesizing in the same manner as in Synthesis Example 4, except that the compound represented by Intermediate 2-3 was used instead of the compound represented by Intermediate 1-3.

[Formula B]

Maldi-tof MS: 1507.9 m/z

(Synthesis Example 9: Synthesis of the compound represented by Intermediate 3-1)

Instead of [4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-hexyl)-phenyl-amine, [3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-phenyl]-(1 The compound represented by Intermediate 3-1 was obtained by synthesizing in the same manner as in Synthesis Example 1 except that -methyl-hexyl)-phenyl-amine was used.

(Synthesis Example 9: Synthesis of the compound represented by Intermediate 3-2)

The compound represented by Intermediate 3-2 was obtained by synthesizing in the same manner as in Synthesis Example 2, except that the compound represented by Intermediate 3-1 was used instead of the compound represented by Intermediate 1-1.

(Synthesis Example 10: Synthesis of the compound represented by Intermediate 3-3)

The compound represented by Intermediate 3-3 was obtained by synthesizing in the same manner as in Synthesis Example 3, except that the compound represented by Intermediate 3-2 was used instead of the compound represented by Intermediate 1-2.

Synthesis Example 11: Synthesis of a compound represented by Formula C

중간체 1-3로 표시되는 화합물 대신 중간체 3-3로 표시되는 화합물을 사용한 것을 제외하고는 합성예 4과 동일한 방법으로 합성하여 하기 화학식 C로 표시되는 화합물을 얻는다.

The compound represented by the following formula (C) was obtained by synthesizing in the same manner as in Synthesis Example 4, except that the compound represented by Intermediate 3-3 was used instead of the compound represented by Intermediate 1-3.

[Formula C]

Maldi-tof MS: 1532.0 m/z

(Synthesis Example 12: Synthesis of the compound represented by Intermediate 4-1)

[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-hexyl)-phenyl-amine instead of [4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]- The compound represented by Intermediate 4-1 was obtained by synthesizing in the same manner as in Synthesis Example 1 except that (1-methyl-hexyl)-phenyl-amine was used.

(Synthesis Example 13: Synthesis of the compound represented by Intermediate 4-2)

The compound represented by Intermediate 4-2 was obtained by synthesizing in the same manner as in Synthesis Example 2, except that the compound represented by Intermediate 4-1 was used instead of the compound represented by Intermediate 1-1.

(Synthesis Example 14: Synthesis of the compound represented by Intermediate 4-3)

The compound represented by Intermediate 4-3 was obtained by synthesizing in the same manner as in Synthesis Example 3, except that the compound represented by Intermediate 4-2 was used instead of the compound represented by Intermediate 1-2.

Synthesis Example 15: Synthesis of the compound represented by Formula D

The compound represented by the following formula (D) was obtained by synthesizing in the same manner as in Synthesis Example 4, except that the compound represented by Intermediate 4-3 was used instead of the compound represented by Intermediate 1-3.

[Formula D]

Maldi-tof MS: 1561.0 m/z

(Synthesis Example 16: Synthesis of the compound represented by Intermediate 5-1)

[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-hexyl)-phenyl-amine instead of [4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-(1 -methyl-hexyl)-phenyl-amine was synthesized in the same manner as in Synthesis Example 1, except that the compound represented by Intermediate 5-1 was obtained.

(Synthesis Example 17: Synthesis of the compound represented by Intermediate 5-2)

The compound represented by Intermediate 5-2 was obtained by synthesizing in the same manner as in Synthesis Example 2, except that the compound represented by Intermediate 5-1 was used instead of the compound represented by Intermediate 1-1.

(Synthesis Example 18: Synthesis of the compound represented by Intermediate 5-3)

The compound represented by Intermediate 5-3 was obtained by synthesizing in the same manner as in Synthesis Example 3, except that the compound represented by Intermediate 5-2 was used instead of the compound represented by Intermediate 1-2.

Synthesis Example 19: Synthesis of the compound represented by Formula E

The compound represented by the following formula (E) was obtained by synthesizing in the same manner as in Synthesis Example 4, except that the compound represented by Intermediate 5-3 was used instead of the compound represented by Intermediate 1-3.

[Formula E]

Maldi-tof MS: 1531.9 m/z

(Synthesis Example 20: Synthesis of the compound represented by Intermediate 6-1)

[2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-phenyl- instead of [4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-hexyl)-phenyl-amine The compound represented by Intermediate 6-1 was obtained by synthesizing in the same manner as in Synthesis Example 1 except that p-tolyl-amine was used.

(Synthesis Example 21: Synthesis of the compound represented by Intermediate 6-2)

The compound represented by Intermediate 6-2 was obtained by synthesizing in the same manner as in Synthesis Example 2, except that the compound represented by Intermediate 6-1 was used instead of the compound represented by Intermediate 1-1.

(Synthesis Example 22: Synthesis of the compound represented by Intermediate 6-3)

The compound represented by Intermediate 6-3 was obtained by synthesizing in the same manner as in Synthesis Example 3, except that the compound represented by Intermediate 6-2 was used instead of the compound represented by Intermediate 1-2.

Synthesis Example 23: Synthesis of a compound represented by Formula F

The compound represented by the following formula F was obtained by synthesizing in the same manner as in Synthesis Example 4, except that the compound represented by Intermediate 6-3 was used instead of the compound represented by Intermediate 1-3.

[Formula F]

Maldi-tof MS: 1419.7 m/z

(Synthesis Example 24: Synthesis of the compound represented by Intermediate 7-1)

[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-hexyl)-phenyl-amine instead of [4-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-butyl]-phenyl- The compound represented by Intermediate 7-1 was obtained by synthesizing in the same manner as in Synthesis Example 1 except that p-tolyl-amine was used.

(Synthesis Example 25: Synthesis of the compound represented by Intermediate 7-2)

The compound represented by Intermediate 7-2 was obtained by synthesizing in the same manner as in Synthesis Example 2, except that the compound represented by Intermediate 7-1 was used instead of the compound represented by Intermediate 1-1.

(Synthesis Example 26: Synthesis of the compound represented by Intermediate 7-3)

The compound represented by Intermediate 7-3 was obtained by synthesizing in the same manner as in Synthesis Example 3, except that the compound represented by Intermediate 7-2 was used instead of the compound represented by Intermediate 1-2.

Synthesis Example 27: Synthesis of the compound represented by Formula G

The compound represented by the following formula (G) was obtained by synthesizing in the same manner as in Synthesis Example 4, except that the compound represented by Intermediate 7-3 was used instead of the compound represented by Intermediate 1-3.

[Formula G]

Maldi-tof MS: 1475.8 m/z

(Synthesis Example 28: Synthesis of the compound represented by Intermediate 8-1)

[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-hexyl)-phenyl-amine instead of [4-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-butyl]-[4 -(tert-butyl-dimethyl-silanyloxy)-phenyl]-phenyl-amine was synthesized in the same manner as in Synthesis Example 1, except that the compound represented by Intermediate 8-1 was obtained.

(Synthesis Example 29: Synthesis of the compound represented by Intermediate 8-2)

The compound represented by Intermediate 8-2 was obtained by synthesizing in the same manner as in Synthesis Example 2, except that the compound represented by Intermediate 8-1 was used instead of the compound represented by Intermediate 1-1.

(Synthesis Example 30: Synthesis of the compound represented by Intermediate 8-3)

The compound represented by Intermediate 8-2 (5 mmol) is dissolved in 50 mL of tetrahydrofuran solvent, and then tetrabutylammonium fluoride (22 mmol) is added at room temperature. After 30 minutes, it was separated by column chromatography to obtain the compound represented by Intermediate 8-3.

Synthesis Example 31: Synthesis of a compound represented by Formula H

The compound represented by Intermediate 8-3 (5 mmol) and sodium hydride (30 mmol) were reacted in 25 mL of N,N-dimethylformamide solvent for 1 hour, and then (3-Iodopropyl)trimethoxysilane (30 mmol) was added and heated to 50 °C. warm up After 8 hours, it is separated by column chromatography to obtain a compound represented by the following formula (H).

[Formula H]

Maldi-tof MS: 1804.3 m/z

(Synthesis Example 32: Synthesis of the compound represented by Intermediate 9-1)

[2-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-hexyl)-phenyl-amine instead of [2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-[4 -(tert-butyl-dimethyl-silanyloxy)-phenyl]-phenyl-amine was synthesized in the same manner as in Synthesis Example 1, except that the compound represented by Intermediate 9-1 was obtained.

(Synthesis Example 33: Synthesis of the compound represented by Intermediate 9-2)

The compound represented by Intermediate 9-2 was obtained by synthesizing in the same manner as in Synthesis Example 2, except that the compound represented by Intermediate 9-1 was used instead of the compound represented by Intermediate 1-1.

(Synthesis Example 34: Synthesis of the compound represented by Intermediate 9-3)

The compound represented by Intermediate 9-3 was obtained by synthesizing in the same manner as in Synthesis Example 30, except that the compound represented by Intermediate 9-2 was used instead of the compound represented by Intermediate 8-2.

Synthesis Example 35: Synthesis of the compound represented by Formula I

The compound represented by the following formula (I) was obtained by synthesizing in the same manner as in Synthesis Example 31, except that the compound represented by Intermediate 9-3 was used instead of the compound represented by Intermediate 8-3.

[Formula I]

Maldi-tof MS: 1748.2 m/z

(Synthesis Example 36: Synthesis of the compound represented by Intermediate 10-1)

[2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-) instead of [4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-hexyl)-phenyl-amine The compound represented by Intermediate 10-1 was synthesized in the same manner as in Synthesis Example 1 except that silanyloxymethyl)-ethyl]-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-phenyl-amine was used. obtained.

(Synthesis Example 37: Synthesis of the compound represented by Intermediate 10-2)

The compound represented by Intermediate 10-2 was obtained by synthesizing in the same manner as in Synthesis Example 2, except that the compound represented by Intermediate 10-1 was used instead of the compound represented by Intermediate 1-1.

(Synthesis Example 38: Synthesis of the compound represented by Intermediate 10-3)

After dissolving the compound represented by Intermediate 10-2 (5 mmol) in 50 mL of tetrahydrofuran solvent, tetrabutylammonium fluoride (44 mmol) is added at room temperature. After 30 minutes, it was separated by column chromatography to obtain the compound represented by Intermediate 10-3.

Synthesis Example 39: Synthesis of the compound represented by Formula J

The compound represented by Intermediate 10-3 (5 mmol) and sodium hydride (45 mmol) were reacted for 1 hour in 25 mL of N,N-dimethylformamide solvent, and then (3-Iodopropyl)trimethoxysilane (45 mmol) was added and heated to 50 °C. warm up After 8 hours, it is separated by column chromatography to obtain a compound represented by the following formula (J).

[Formula J]

Maldi-tof MS: 2105.1 m/z

(Synthesis Example 40: Synthesis of the compound represented by Intermediate 11-1)

{4-(tert-Butyl-dimethyl-silanyloxy)-1-[3-(tert-butyl) instead of [4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-hexyl)-phenyl-amine -dimethyl-silanyloxy)-propyl]-butyl}-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-phenyl-amine was synthesized in the same manner as in Synthesis Example 1, except that the intermediate 11- The compound represented by 1 was obtained.

(Synthesis Example 41: Synthesis of the compound represented by Intermediate 11-2)

The compound represented by Intermediate 11-2 was obtained by synthesizing in the same manner as in Synthesis Example 2, except that the compound represented by Intermediate 11-1 was used instead of the compound represented by Intermediate 1-1.

(Synthesis Example 42: Synthesis of the compound represented by Intermediate 11-3)

The compound represented by Intermediate 11-3 was obtained by synthesizing in the same manner as in Synthesis Example 38, except that the compound represented by Intermediate 11-2 was used instead of the compound represented by Intermediate 10-2.

Synthesis Example 43: Synthesis of a compound represented by Formula K

It was synthesized in the same manner as in Synthesis Example 39 except that the compound represented by Intermediate 11-3 was used instead of the compound represented by Intermediate 10-3 to obtain a compound represented by the following formula (K).

[Formula K]

Maldi-tof MS: 2217.0 m/z

Comparative Synthesis Example 1: Synthesis of a compound represented by Formula C-1

(1-Methyl-hexyl)-phenyl-p-tolyl-amine (100 mmol) and 3,4-Dihydroxy-cyclobut-3-ene-1,2-dione (50 mmol) were mixed with toluene (300 mL) and butanol ( 300 mL), reflux, and remove the resulting water with a Dean-stark distillation apparatus. After stirring for 12 hours, the reaction product was distilled under reduced pressure and purified by column chromatography to obtain a squaylium-based compound. After dissolving this compound (5 mmol) in 600 mL of chloroform solvent, pyridine-2,6-dicarbonyl dichloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL of chloroform, and then added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a compound represented by the following Chemical Formula C-1.

[Formula C-1]

Maldi-tof MS: 1175.5 m/z

Comparative Synthesis Example 2: Synthesis of a compound represented by Formula C-2

Propionic acid 2-{(2-cyano-ethyl)-[4-(2-hydroxy-3,4-dioxo-cyclobut-1-enyl)-phenyl]-amino}-ethyl ester (60 mmol), 1-( 2-Ethyl-hexyl)-1H-indole (60 mmol) is added to toluene (200 mL) and butanol (200 mL), refluxed, and the resulting water is removed using a Dean-stark distillation apparatus. After stirring for 12 hours, the green reactant was distilled under reduced pressure and purified by column chromatography to obtain an asymmetric squarylium compound. After dissolving this compound (5 mmol) in 600 mL of chloroform solvent, Pyridine-2,6-dicarbonyl dichloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL of chloroform, and then added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a compound represented by the following Chemical Formula C-2.

[Formula C-2]

Maldi-tof MS: 1088.48 m/z

Comparative Synthesis Example 3: Synthesis of a compound represented by Formula C-3

(1) 2,4-dimethyldiphenylamine (10 mol), 1,2-epoxycyclohexane (12 mol), sodium hydride (12 mol) were put in N,N-dimethylformamide and heated to 90°C to 24 stirred for hours. Ethyl acetate was added to this solution, washed twice with water, and the organic layer was extracted. The extracted organic layer was distilled under reduced pressure and separated by column chromatography to obtain Intermediate 1.

(2) Intermediate B-4 (10 mmol), iodomethane (15 mmol), and sodium hydride (15 mmol) were added to N,N-dimethylformamide and stirred at room temperature for 24 hours. Ethyl acetate was added to this solution, washed twice with water, and the organic layer was extracted. The extracted organic layer was distilled under reduced pressure and separated by column chromatography to obtain Intermediate 2.

(3) Intermediate C-7 (60 mmol) and 3,4-dihydroxy-3-cyclobutyne-1,2-dione (30 mmol) were added to toluene (200 mL) and butanol (200 mL) and refluxed. The resulting water is removed with a Dean-stark distillation apparatus. After stirring for 12 hours, the green reactant was distilled under reduced pressure and purified by column chromatography to obtain a core compound represented by the following formula.

(4) After dissolving the core compound (5 mmol) in 600 mL of chloroform solvent, triethylamine (50 mmol) is added. Dissolve 2,6-pyridinedicarbonyl dichloride (20 mmol) and p-xylylenediamine (20 mmol) in 60 mL of chloroform and drop them simultaneously at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a compound represented by Formula C-3.

[Formula C-3]

Maldi-tof MS: 1230.59 m/z

(Synthesis of photosensitive resin composition)

Example 1

A photosensitive resin composition according to Example 1 was prepared by mixing the components mentioned below in the composition shown in Table 1 below.

Specifically, a photopolymerization initiator was dissolved in a solvent and stirred at room temperature for 2 hours, and then a binder resin and a photopolymerizable monomer were added thereto and stirred at room temperature for 2 hours. Then, the compound prepared in Synthesis Example 4 (compound represented by Formula A) as a colorant was added to the obtained reactant and stirred at room temperature for 1 hour. Then, the product was filtered three times to remove impurities, thereby preparing a photosensitive resin composition.

(Unit: % by weight) Ingredients content coloring agent dyes Compound of Synthesis Example 4 28 pigment Green pigment dispersion 15 yellow pigment dispersion 35 binder resin (A)/(B)=15/85(w/w),
Molecular Weight (Mw) = 22,000 g/mol
(A): methacrylic acid
(B): benzyl methacrylate 3 photopolymerizable monomer Dipentaerythritol Hexaacrylate (DPHA) 2.5 photopolymerization initiator 1,2-octanedione 0.3 menstruum PGMEA (Propylene Glycol Monomethyl Ether Acetate) 16 other additives γ-Glycidoxy propyl trimethoxysilane 0.2 Total 100

Example 2

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 8 (compound represented by Formula B) was used instead of the compound of Synthesis Example 4 (compound represented by Formula A).

Example 3

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 11 (compound represented by Formula C) was used instead of the compound of Synthesis Example 4 (compound represented by Formula A).

Example 4

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 15 (compound represented by Formula D) was used instead of the compound of Synthesis Example 4 (compound represented by Formula A).

Example 5

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 19 (compound represented by Formula E) was used instead of the compound of Synthesis Example 4 (compound represented by Formula A).

Example 6

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 23 (compound represented by Formula F) was used instead of the compound of Synthesis Example 4 (compound represented by Formula A).

Example 7

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 27 (compound represented by Formula G) was used instead of the compound of Synthesis Example 4 (compound represented by Formula A).

Example 8

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 31 (compound represented by Formula H) was used instead of the compound of Synthesis Example 4 (compound represented by Formula A).

Example 9

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 35 (compound represented by Formula I) was used instead of the compound of Synthesis Example 4 (compound represented by Formula A).

Example 10

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 39 (compound represented by Formula J) was used instead of the compound of Synthesis Example 4 (compound represented by Formula A).

Example 11

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 43 (compound represented by Formula K) was used instead of the compound of Synthesis Example 4 (compound represented by Formula A).

Comparative Example 1

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Comparative Synthesis Example 1 (compound represented by Formula C-1) was used instead of the compound of Synthesis Example 4 (compound represented by Formula A) .

Comparative Example 2

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Comparative Synthesis Example 2 (compound represented by Formula C-2) was used instead of the compound of Synthesis Example 4 (compound represented by Formula A). .

Comparative Example 3

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Comparative Synthesis Example 3 (compound represented by Formula C-3) was used instead of the compound of Synthesis Example 4 (compound represented by Formula A) .

Evaluation: Determination of the chemical resistance of the composition

The photosensitive resin composition prepared in Examples 1 to 11 and Comparative Examples 1 to 3 was applied to a transparent square glass substrate (bare glass) using a spin-coater (K-Spin8 manufactured by KDNS). Each was applied to a thickness of 0.5 μm. After that, baking is performed at 80°C for 120 seconds using a hot-plate, and exposure is performed at a power of 1000mJ using an exposure machine (Ushio), followed by a hot-air circulation oven at 230°C. Specimens were prepared by baking in a convection oven for 5 minutes.

Thereafter, the prepared color filter specimen was immersed in PGMEA solution at room temperature for 5 minutes, and chemical resistance was evaluated as follows based on the rate of change in absorbance intensity at 650 nm before and after solution immersion, and the results are shown in Table 2 below. It was.

chemical resistance = {

(unit: %) chemical resistance Example 1 3.0 Example 2 3.4 Example 3 3.1 Example 4 3.2 Example 5 3.3 Example 6 3.4 Example 7 2.3 Example 8 2.0 Example 9 2.3 Example 10 2.0 Example 11 1.7 Comparative Example 1 90 Comparative Example 2 92 Comparative Example 3 30

From Table 2, it can be seen that the photosensitive resin compositions (Examples 1 to 11) according to the exemplary embodiment have excellent chemical resistance, and thus are very suitable for use in CMOS image sensors.

Although preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims, the detailed description of the invention, and the accompanying drawings, and this also It goes without saying that it falls within the scope of the invention.

Claims (17)

(A) binder resin;
(B) a photopolymerizable monomer;
(C) a photoinitiator;
(D) colorants including pigments and dyes; and
(E) solvent
including,
The dye surrounds the core and the core represented by the following formula (1), consisting of a shell represented by the following formula (2), a photosensitive resin composition:
[Formula 1]

[Formula 2]

In Formula 1 and Formula 2,
R ¹ to R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group, wherein R ¹ to R ⁸ are not hydrogen atoms at the same time,
R ¹ and R ² may be fused to each other to form a ring, or R ³ and R ⁴ may be fused to each other to form a ring,
At least one of R ¹ , R ² , R ⁵ and R ⁶ includes a siloxane group at the terminal,
At least one of R ³ , R ⁴ , R ⁷ and R ⁸ includes a siloxane group at the terminal,
L ^a and L ^b are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group,
n1, n2, n3 and n4 are each independently an integer of 0 or 1, n1+n2 ≠ 0, n3+n4 ≠ 0,
n is an integer greater than or equal to 2;
According to claim 1,
The photosensitive resin composition comprising an ether linking group (*-O-*) to the substituent containing a siloxane group at the terminal.
3. The method of claim 2,
At least one of R ¹ , R ² , R ⁵ and R ⁶ and at least one of R ³ , R ⁴ , R ⁷ and R ⁸ are each represented by the following Chemical Formula 3 photosensitive resin composition:
[Formula 3]

In Formula 3,
R ⁹ to R ¹¹ are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C1 to C20 alkoxy group,
L ¹ is a substituted or unsubstituted C1 to C20 alkylene group.
According to claim 1,
Any one of R ¹ , R ² , R ⁵ and R ⁶ and any one of R ³ , R ⁴ , R ⁷ and R ⁸ is each independently a photosensitive resin composition comprising a siloxane group at the terminal.
According to claim 1,
Any two of R ¹ , R ² , R ⁵ and R ⁶ and any two of R ³ , R ⁴ , R ⁷ and R ⁸ are each independently a photosensitive resin composition comprising a siloxane group at the terminal.
According to claim 1,
Any three of R ¹ , R ² , R ⁵ and R ⁶ and any three of R ³ , R ⁴ , R ⁷ and R ⁸ are each independently a photosensitive resin composition comprising a siloxane group at the terminal thereof.
5. The method of claim 4,
Formula 1 is a photosensitive resin composition represented by the following Formula 1-1:
[Formula 1-1]

In Formula 1-1,
R ¹ to R ⁴ , R ⁶ and R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group, wherein R ¹ to R ⁴ , R ⁶ and R ⁸ is not a hydrogen atom at the same time,
R ¹ and R ² may be fused to each other to form a ring, or R ³ and R ⁴ may be fused to each other to form a ring,
R ¹ To R ⁴ , R ⁶ And R ⁸ All do not include a siloxane group,
R ⁵ and R ⁷ are each independently a C1 to C20 alkyl group including a siloxane group at the terminal or a C1 to C20 alkoxy group including a siloxane group at the terminal,
n5 and n6 are each independently an integer of 0 or 1.
5. The method of claim 4,
Formula 1 is a photosensitive resin composition represented by Formula 1-2 below:
[Formula 1-2]

In Formula 1-2,
R ² , R ⁴ , R ⁶ and R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group, wherein R ² , R ⁴ , R ⁶ and R ⁸ is not a hydrogen atom at the same time,
R ² , R ⁴ , R ⁶ and R ⁸ all do not contain a siloxane group,
R ¹ and R ³ are each independently a C1 to C20 alkyl group including a siloxane group at the terminal or a C1 to C20 alkoxy group including a siloxane group at the terminal,
n5 and n6 are each independently an integer of 0 or 1.
6. The method of claim 5,
Formula 1 is a photosensitive resin composition represented by the following Formula 1-3:
[Formula 1-3]

In Formula 2-3,
R ² , R ⁴ , R ⁶ and R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group, wherein R ² , R ⁴ , R ⁶ and R ⁸ is not a hydrogen atom at the same time,
R ² , R ⁴ , R ⁶ and R ⁸ all do not contain a siloxane group,
R ¹ , R ³ , R ⁵ and R ⁷ are each independently a C1 to C20 alkyl group including a siloxane group at the terminal or a C1 to C20 alkoxy group including a siloxane group at the terminal,
n5 and n6 are each independently an integer of 0 or 1.
7. The method of claim 6,
Chemical Formula 1 is a photosensitive resin composition represented by the following Chemical Formula 1-4:
[Formula 1-4]

In Formula 1-4,
R ⁶ and R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group,
R ⁶ and R ⁸ both do not contain a siloxane group,
R ¹ to R ⁵ and R ⁷ are each independently a C1 to C20 alkyl group including a siloxane group at the terminal or a C1 to C20 alkoxy group including a siloxane group at the terminal,
n5 and n6 are each independently an integer of 0 or 1.
According to claim 1,
The core represented by Formula 1 is a photosensitive resin composition having a maximum absorption wavelength at 610 nm to 640 nm.
According to claim 1,
The shell represented by Formula 2 is a photosensitive resin composition represented by Formula 2-1 below.
[Formula 2-1]

According to claim 1,
The dye is a photosensitive resin composition represented by any one of the following Chemical Formulas A to K.
[Formula A]

[Formula B]

[Formula C]

[Formula D]

[Formula E]

[Formula F]

[Formula G]

[Formula H]

[Formula I]

[Formula J]

[Formula K]

According to claim 1,
The dye is a green dye photosensitive resin composition.
The photosensitive resin film containing the photosensitive resin composition of any one of Claims 1-14.
A color filter comprising the photosensitive resin film of claim 15 .
A CMOS image sensor comprising the color filter of claim 16 .